Picture a diner at lunch hour with only one server. She’s seating the customer, taking the order, pouring water and drinks, cooking the food, plating the food, serving the food, refilling drinks, giving out checks, and taking payment at the register. Every table is full. Patrons are flagging her down wanting a refill, wanting their check, complaining the burger was undercooked, asking for more ketchup for the fries.

That was my workday for the first stretch of the COVID remote era. All of it happening in my guest bedroom with a work computer, monitor, webcam, and microphone.

When I was the IT manager for one of the colleges, back in the days of the Aces, the chaos was grim. Everyone in the college occupied one building, and it was incredibly convenient for faculty and staff to take an elevator up to my office or walk down a flight to stop in for help. Multiple interruptions a day. I battled a growing resentment inside me as I stopped what I was working on to take care of them in the moment. That building frustration came from my focus getting disrupted while working on technical issues from a demanding client who went through appropriate channels to request my time, and was in line waiting for their issue to be resolved. In those brief moments where I didn’t have an in-person client and completed an update to one of my department servers, I dreamed about a workday where I could work on my work in peace.

I got that wish when I moved to the Canvas Admin position. But the chaos followed me, just in a different form. As the sole Canvas administrator for the university, the volume of requests during those early remote months of COVID was staggering. Faculty were elbowing and clawing their way to me to get their course issues resolved. I found myself spread way too thin, trying to serve everyone all day with no structure. No schedule. No boundaries. Just an open door with messy tables that haven’t been cleaned, and a growing crowd of people in the doorway wanting to be served.

My wife saw the toll Spring 2020 took on me. I’d stagger down the stairs after the workday ended, lie down on the sofa, put my forearm over my eyes, and try to forget everything that had just happened. But it was now after-work time, relating time, evening activity time, and I had no energy left in my tank for family life. The job was consuming everything, and the person I loved the most was getting my least.

Something had to change. So I redesigned the diner.

First, I locked the front door. Only I would decide when a customer came in to eat. One hungry person at a time. I could see the line of people outside on the sidewalk, stretching down the street, but for this new experiment I had to allow the line to exist, had to allow the disappointment at not providing immediate service to all, and had to focus on one person at a time. I ripped out most of the tables and booths, keeping one table in the center of the diner with plenty of room around it for elbow room and enough space to just sit and enjoy the experience. I threw out the chipped standard white plates so many ate off of in the past and invested in quality stone dishware. I bought new cloth napkins and introduced new silverware; utensils that looked nice and signaled to the customer this was a quality establishment they were in. I limited the menu to only a few entrees that previous customers raved about, thus eliminating decision fatigue for the eater, and less for me to keep track of in the kitchen since I was still preparing every meal myself.

I could hear the complaints from outside. “I’m hungry! Let me in! It’s time to eat! Why isn’t your door open?” I genuinely felt bad about it. It went against my Prime Directive, my core ethos, to serve everyone who needed help. The Council of Wraiths assembled and began deliberating on my decision to renovate.

Here’s what the redesigned diner looked like in practice. Four hour-long consults each workday: 9 a.m., 10 a.m., 2 p.m., and 3 p.m. Not 30-minute slots, because I’d learned that limited amount of time wasn’t long enough to address every question. Once I helped resolve a client’s Canvas course issue effectively and efficiently, they had other questions pop up. When a customer receives knowledgeable service, they want more of it. Also, with a 30-minute timeframe, one consult would bleed into the next reserved time slot, like a doctor running behind because they gave their patient the attention the situation required, making the next patient wait as a consequence. And I felt bad about cutting a consultation short for a client because someone else was next in line. It was the state of affairs at that time, but as a customer I never liked being told time was up when I was enjoying my experience. Sixty minutes proved to be a luxurious amount of time for full attention to the client’s issue, plenty of room for follow-up questions, and if we ended early, both of us got some precious minutes back in our workday to, you know, go to the bathroom. Or refill a water bottle. Instead of back-to-back-to-back-to-back meetings with no room to think or process what just happened.

The time slots were reservable via my online calendar scheduler, the link embedded in my email signature (which reached many, many clients every day) and posted on the Canvas support webpage. First come, first served. That’s the new standard.

My workday started at 7:30 am. Before the first consult, I spent the early morning triaging emails that came in overnight and working on big-ticket projects. My lunch hour was mine, sacrosanct, without interruption. After lunch, more email triage. And I planned time at the end of the workday to reflect on what had been done and make mental notes about what would be awaiting me the next morning. I had to wash the dishes and silverware, clean the table surface, mop the floor, and clean the kitchen to put everything back in its place. My workday ended at 4:30. I would not be accommodating a 4:27 pm drop-in consultation because it happened to be convenient for a faculty’s schedule. I was nervously trying to allow waiting in line to be part of Canvas support, because there was only one of me to serve my clientele. And my mental landscape mattered to me.

I never asked management for permission to set this up. They were so busy with their own projects and meetings that my Canvas Admin role operated in a kind of benign neglect with very little oversight and direction. I was given the autonomy to modify my workday, and I took it. Since no faculty were complaining up the chain, and all the requests for help were taken care of in a quick timeframe, nobody questioned it. The initiative worked because I trusted my own instincts of what the workday required, and the institution’s inattention gave me the room to act on it.

During the consult itself, I quit my email application. I quit Microsoft Teams. Only Zoom and my web browser was open with one tab: the client’s Canvas account. They had my full, undivided attention for that hour, even though my mind was quietly dreading everything piling up during the consult.

But in the diner, none of that showed. I opened the door, greeted the one customer, escorted them to their table where a cool glass of ice water was poured and ready. Utensils were polished. An attractively clean, minimalist, classy menu awaited them on the table. I took their order, provided a free appetizer while I chatted with them from the kitchen as I cooked their meal, learning about their day, commiserating with the stress going on in their life. As I prepped the plates, I told them how glad I was that we were able to meet in the diner today. I watched them feel welcome as the conversation was focused on them. I served their meal without tripping over other customers’ backpacks on the floor, without dodging people moving all around me, without dropping plates and having to redo the dish. I then sat down at the table with them and continued chatting while they ate. When I saw they’d finished, I quietly removed their plates while talking about their next visit to the diner, set a shiny, crisp apple down on the table for them to take as a parting gift, set the bill on the table with a $0 balance, and thanked them for coming in.

They were always appreciative. And I mean always.

After they left to move on with their day, I cleaned the table, set up fresh utensils, napkin, and a new menu, and greeted the next customer. Same process. Same attention. Same one table.

Eventually the din of complaints outside faded in volume. The pile of requests after the consult decreased as the remote era slowly morphed into masked in-person society and work resumed in a new normal. My four consults a day experiment was working well. The one-table diner experience let me reclaim energy internally, and it proved that limiting access didn’t mean limiting care. This success made the Council of Wraiths adjourn and disband. No guilty verdict was needed.

If you’re reading this and recognizing your own workday in that opening paragraph, I want to tell you something. The open door isn’t generosity, even though it feels like it and looks like it. Your institution will praise you for it. But unstructured availability isn’t sustainable. I believe the quality of your service degrades in direct proportion to the number of tables you’re trying to serve at once. Your clients deserve your full attention, and they can’t get it when you’re mentally cooking three other meals while taking their order. If you’re the only server in a diner full of customers, you don’t need more tables. You need fewer. Here’s a secret...nobody is going to give you permission to remove them. You’re going to have to do it yourself, and you’re going to feel guilty about it, but the guilt will fade as you see the improvement in your output as well as your internal happy tank.

The diner is still successful years later. Four reservation slots, same times. Same boundaries established. Same one table.

I didn’t learn this from a management seminar or a productivity book, though Jason Fried would probably nod knowingly if they saw it. I learned it from burning out in a guest bedroom while my wife watched the person she married disappear into a sofa cushion every evening, then psyche up to do it all over again the next day. The redesign was the right decision that happened at the right time to make me better at my job.

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There’s a product some of my clients use that makes me want to vomit in my mouth.

I won’t name it, but you might be able to guess what it is. And I’m not alone. Every technology professional has some product that they detest. A software application or an operating system or a cloud-based subscription service that they can’t stand. Years of accumulated evidence about a flawed, overpriced product, actively hostile to the person paying for it in some cases. We techs have read about the vulnerabilities. We’ve watched the subscription quietly creep up in price. We’ve been made aware of the telemetry collecting data our clients didn’t agree to sharing. We’ve watched a multi-billion dollar company ship a product that requires weekly updates to fix errors that existed the moment it was installed, and we’ve thought to ourselves: who would buy a car that needs to go to the repair shop the minute they drive it off the lot? Who would plug a new television into their living room wall, press the power button on the remote control, and have to navigate six menus just to watch a show?

I would. Because that flawed product paid my mortgage. It paid for my car. It enabled me to have a successful 30-year career in technology support, because I was paid to apply fixes to known problems for my clients. I find the irony to be sadly laughable. The product I have disdain for is the same product that fed my family.

My clients still use the product, and they have no intention of stopping. They’re willingly paying an annual subscription for it because they choose not to learn an alternative way of composing a letter or managing their email. That subscription is the cost of comfortable computing. It’s what they know, and when something goes wrong with it, they call me.

This is where the technology consigliere demonstrates their worth.

In the 1972 movie The Godfather, Tom Hagen never yelled at his boss, Vito Corleone. When the boss’ son Sonny was blustering about going to war with other crime families in New York, Hagen raised his voice to meet the volume in the room, but never with the Don, he counseled. He advised. He explained the risks, the costs, and the alternatives. When Don Corleone made a decision Hagen would not have made himself, Hagen served the decision. That was his job. The consigliere doesn’t run the family. The consigliere serves the family, and the family chooses.

I sit at a client’s computer desk, watching them struggle with a misleading subscription page with funny math and dark patterns. Something inside me is screaming. I want to explain to my client why this company doesn’t deserve their money. I want to walk them through the telemetry settings they’ve never seen and show them what’s being collected. I want to recommend alternatives I’ve personally tested that would cost them less and respect their privacy and data sovereignty more. I have a Lewis Black rant building in my gut, and it would feel cathartic to let it rip.

But the client didn’t invite me into their home to hear my full-throated opinions about the technology industry. They want me in their home because something isn’t working, and they need help. They need a calming presence. They need technical competence. They need the consigliere, not the critic.

So I quietly breathe in through my nostrils, and I quietly exhale through parted lips. I toss my judgmental jacket outside on the front porch where they won’t see it. And I help them with the software application they chose, the operating system they’re comfortable with, or the annual subscription they paid for. I confirm it’s updated. I ensure their subscription will not expire unexpectedly, and is the appropriate tier for what they actually use. I make sure their settings protect their privacy as much as the product allows. And if they directly ask me whether there’s something better out there, I tell them the truth. I lay out the options, I explain the trade-offs, and I give them my honest opinion with their best interests in mind.

Then I let them choose.

Most of the time they stay with what they know, and that’s totally fine. Because the moment I start making my clients feel judged for their technology choices is the moment I stop being a consigliere and start being the gatekeeper I recently wrote about. The tech geek who made people feel small for not knowing what he knew? I left that era behind. I don’t breathe life back into that stereotype just because my opinions are better informed now.

The hardest part of my work isn’t the technology. It’s the restraint my work requires. It’s sitting with someone I care about, watching them use something I’d never install on my own machine, and knowing that my asking them to relearn decades of muscle memory for my peace of mind isn’t a call I get to make. The consigliere advises. The client decides. The consigliere serves the decision.

I think about this as I have gradually been building a practice where I’ll be sitting in people’s homes, helping families with their digital lives. There will be products in those homes that I would never buy myself. The software subscription charge on their credit card statement will make my neck twitch. And I will set my judgmental jacket outside on the front porch, smile, and ask them to show me what’s going on.

The honor I have with being invited into someone’s home to help with their technology doesn’t give me carte blanche to impose my preferences. Their invitation is a gift of trust. And that trust requires me to serve the person in front of me, not the version of their technology landscape I wish they had.

Tom Hagen served the Corleone family for decades. He didn’t always agree with the decisions, but he served to the best of his ability.

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In 1997, if your computer broke, you called a tech geek because you had to. The fixes couldn’t be found anywhere else. There was no YouTube tutorial, no Reddit thread, no AI agent that could spit out steps to reinstall a printer driver. Google barely existed. Computer technologists held the keys to specialized knowledge, and that gatekeeping provided them with an awkwardly-displayed authority. You needed us nerds despite our dorky appearances in the office and our inabilities to fit in socially. We knew we would never measure up in the cool competition. And since we were the unpopular ones growing up, we made the popular, cool people pay for it by guarding the information close to our pocket protectors.

That era is over.

Today, anyone with a phone can troubleshoot their own problems. A faculty member struggling with a Canvas gradebook can find a three-minute walkthrough without ever contacting me. A client with a frozen laptop can ask an AI assistant, on another device, for a bulleted list procedure to resolve the issue in minutes. The information embargo that defined technology support for decades has morphed into an equal playing field. Every answer is available to everyone, all the time.

So if the information isn’t scarce anymore, what can a technology professional actually offer someone?

Consider Hawkeye Pierce.

For anyone who didn’t grow up watching the TV show M*A*S*H, Captain Benjamin Franklin “Hawkeye” Pierce was a surgeon in a Korean War field hospital who wore a bathrobe to the mess tent, cracked jokes during briefings, and treated military protocol like a rash. To anyone entering the 4077th for the first time, he looked like the most undisciplined doctor in the war. He never dressed like a soldier. He never acted maturely. And he never performed the role of an officer the way the army expected.

But when the choppers came in and the wounded arrived, Hawkeye was the best surgeon in the operating room, without question. His choice to wear a bathrobe was a refusal to let the clothing define the competence.

That resonates with me. A lot.

I’ve never been a stereotypical technologist, but I know what it’s like to be unpopular growing up, and I am a total insecure nerd on the inside who has worked hard to avoid being a dork in public. I don’t dress in khaki pants and a light blue long-sleeve buttondown shirt. I don’t rattle off jargon to demonstrate expertise. I don’t project the aura of superiority that some tech professionals still cling to, a cringey reminder of an era when knowing things other people didn’t was the appeal to many tech geeks. That era rewarded gatekeeping. It rewarded making the client feel small enough to need you.

Yuck.

Now, the Hawkeye comparison only goes so far. Hawkeye was a womanizer. He fooled around with so many nurses at the 4077th, it’s a wonder he never got himself blacklisted among every woman on the base. He also spent half his off-duty hours drinking homemade gin from a still in his tent. I’m not Hawkeye in either department. I rarely drink, I’ve been happily married for 16 years, and while I’m a charming gentleman who treats any woman with courtesy, dignity, and kindness, I don’t confuse charm with inappropriate flirtation. The bathrobe philosophy applies to my work, not my personal conduct.

In 30 years of being a professional tech, I’ve learned when information stops being scarce, observation becomes a rare skill. Relation becomes a sought-after trait. Attention to nuance becomes a competitive advantage. I’m fully aware that ChatGPT can give my client a list of steps to fix their Canvas issue. Sometimes that list will solve the problem, but it won’t notice the tension in their voice. It won’t recognize that this is the third time this quarter they’ve contacted support and are starting to feel dumb. It won’t read the body language that says “I’m confused and overwhelmed by everything going on in my life, and this Canvas course error was the last straw.”

I see that. CoPilot doesn’t. And because I can see it, I can respond to the whole person, not just a work ticket.

The world got dramatically better at grabbing information in the past three decades. Unfortunately, it only took two years to torpedo society’s ability to interact with other humans, and modern tech support in 2026 rarely has face-to-face interactions at all. People communicate through screens, not passing in the hallway. They’ve lost practice with the in-person skills that used to be second nature. The information flowed freely while the social muscles atrophied.

My point is this: the technology professional who can still do both, solve the problem and see the person, is more valuable now than at any point in my career. Sort of ironic that the more soft skills became essential the more the tech support profession decided to make that trait obsolete.

Every surgeon in the O.R. went to medical school. They all had the knowledge. Hawkeye was the best because of how he served at the 4077th: never genuflecting to the bureaucracy but providing total presence with the patient on the table. The bathrobe was sloppy, but it was a declaration that the uniform didn’t matter. The soldier on the table mattered.

My clients don’t need me for the answers anymore. They can find the answers. They need me because when they’re stressed and frustrated and their technology has failed them at the worst possible moment, I’m the person who makes them feel seen, heard, and known. That’s what the relational technologist offers in a world drowning in information and starving for attention.

Can’t get that with Gemini.

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In my mid-20s, I was trying to learn how to be a better man in the dating world. I read a book whose title I’d rather not disclose, but one line from it has never left me: “Success is preparation meeting opportunity.” If I’m dressed well, if I smell decent, if I don’t have boogers hanging out my nose or atrociously bad breath, and if I’m a kind and entertaining date, some women will say yes to a second date.

I applied that line to everything.

If I can learn everything about a topic before the moment arrives, I will be successful when that moment comes. In my explanation, in my problem solving, in my confidence walking into a room. The preparation isn’t optional, it’s mandatory for me. I don’t fly by the seat of my pants with technology support. I study, I rehearse in my head, I visualize the scenario, and when it’s time, I deliver.

There’s a scene in the first Men in Black movie that has turned into professional ethos for me. Will Smith’s character is in a recruitment competition with a room full of military and law enforcement candidates. In the weapons portion of the evaluation, targets pop up like a shooting gallery, aliens and civilians, and every candidate immediately opens fire, riddling the alien targets with bullets. Smith just watches. Doesn’t raise his gun. After everyone empties their clips, he fires two shots at one unexpected target and calmly explains why. His explanation was observational, it was assessing, it was measured, and it was bang-on correct, no pun intended.

That’s me at work, in my professional environment.

An email arrives, management and tech colleagues are CC’d. A faculty client is at their wit’s end. Something in Canvas isn’t working. They want answers now. Some managers feel the immediate need to respond, sometimes directing me to act even though I’m already on the original thread. Some colleagues fire off a reply within minutes, asking the client to submit a ticket.

I don’t respond to the client. I think about the client’s issue. I visualize the issue. I log into the client’s Canvas account and see exactly what they see. And then I see what they don’t see. I see the solution, often a user error, and I see the path to explain it without making anyone feel dumb.

About an hour later, I fire. One email to the group. Informed, articulated, containing exactly what the client needs. If you have follow-up questions, I’m here. Otherwise, I think we’re in a better space.

Even though I gave myself permission years ago to say “I don’t know,” I still grit my teeth every time. I wrote an essay about the power of those three words, and I stand by what I wrote. But I still experience a flash of something close to shame when I have to say those three words. I view it as a weakness, even knowing it isn’t. Preparation is I don’t know’s kryptonite.

Here’s where it shows up with clients. When someone calls me stressed about their technology, I feel their stress. My first impulse is to breathe in short bursts, talk fast, interrupt them with solutions. But something inside me says, “Hold.” And I hold. I say nothing. I listen to their every word.

Stressed people don’t like silence. So they keep talking. And because they keep talking, I often get the one critical nugget of information that tells me what’s actually happening, what changed, and what needs to change to get things fixed for them. If I’d interrupted with my first instinct, I’d have missed it.

The calculus of a consigliere places a mandate on me: the client gets the spotlight. All of it. I’m not performing on stage. I’m identifying what changed about their technology, determining what needs to happen for them to return to normalcy, and doing what I need to do to get them back to regular breathing. That’s the job. Getting them breathing again. Get their shoulders to relax. Get them to happy hour sooner. That’s my credo.

This calculus has served me well. Extraordinarily well, not gonna lie. Thirty years of preparation meeting opportunity. Rarely embarrassed. Rarely caught without an answer. Rarely exposed.

But there’s a darker side to this.

In Spring 2020, the world shut down. My university, like every university, scrambled to move instruction online for the upcoming quarter. Roughly 2,000 faculty members needed to learn how to teach through Canvas and Zoom and Teams within weeks. Faculty who had built successful careers standing in classrooms and delivering lectures were now facing their students in a computer monitor with a bunch of students in little square windows, some of whom might not even turn their cameras on.

Two of my colleagues stepped up to run live training webinars, multiple sessions every workday, walking scores of anxious faculty through the tools and concepts they’d need. It was heroic work. Those two stood in front of the chaos, fielded the fear, absorbed the frustration, and delivered. I have deep respect for what they did during that stretch.

I wasn’t one of the presenters.

I saw the webinar plan forming and I knew, with a certainty I felt in my chest, that I wasn’t going to be effective in that modality. I know what happens to me in live training when an attendee derails the flow. Someone doesn’t grasp a concept, raises their hand, interrupts with a question, and the whole room follows. I lose focus. My brain glitches. I can’t recover the thread. I’m the university’s Canvas administrator. I know the platform better than anyone in that room. So I volunteered for the background roles instead: moderating the chat Q&A, monitoring the shared inbox, responding to the avalanche of individual faculty requests pouring in.

Those contributions mattered. The inbox alone was a firehose, and someone had to catch it. But if I’m honest with myself, I chose those roles because they weren’t public-facing. I chose the background because the foreground carried a risk I wasn’t willing to take: the risk of looking less than completely knowledgeable in front of hundreds of stressed faculty during the most high-stakes Canvas training moment in the university’s history.

The sharpshooter picked his position carefully. But this time, I’m not sure the calculus was purely strategic. I think some of it was fear.

I think about that sometimes, now that I’m preparing to stand at a podium myself in October. The methodology that made me effective, the preparation, the restraint, the refusal to fire until I’m certain, is the same methodology that kept me offstage when the stage needed me most. The same instinct. Doing two different jobs depending on whether I call it caution or fear.

I don’t have a logical explanation for that. The sharpshooter doesn’t always know, in the moment, whether he’s waiting for the right shot or just afraid to pull the trigger. All I know is that my preparation continues. And the next time the moment arrives, I intend to be standing in front of the room.

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I want to tell you about the most beautiful workflow I’ve ever built, so you can appreciate how badly I broke it.

Early in my career I managed 600 PC workstations across 12 computer labs. Four different hardware types meant four separate disk images, and I maintained all of them using Symantec Ghost, the industry standard for cloning workstations at the time. My process was glorious. I’d run Windows Updates on a prototype workstation, update every software application to the latest version, clean up unnecessary files, and configure a folder of desktop shortcuts so students wouldn’t have to wrestle with the Start Menu. Then I’d upload that prototype image to my Ghost server, which was actually just a workstation in my office dedicated to blasting images to lab computers across the campus network.

During break weeks, when students weren’t using the labs for academic work, I’d lock a lab’s door, remotely connect to my Ghost server, and send a command to the 30+ workstations in the room. I’d watch them all automatically reboot, connect to the reimaging session, and receive a 30 GB image chunk by chunk. It normally took 90 minutes to complete. I’d read a magazine while everything got transmitted; there was nothing I needed to do but watch the process. When the imaging finished, every workstation rebooted at the same time, received its specific computer name to be recognized on the campus network, rebooted again, and came back up to the login screen with custom background wallpaper. Different wallpaper every term, on purpose, so I could spot at a glance which workstations might not have received a successful update. I’d log into a random workstation with a guest account, verify printing and internet access, reboot, open the lab, and move on to the next one.

Those were the good ol’ days.

As part of my workstation customizations, I always set a specific homepage URL on every lab workstation so the browser would launch directly to the university portal. Students expected it. It was the front door of their campus experience on any lab computer. For some reason, and I have no one to blame but myself, I fat-fingered one additional character in the URL address before uploading the prototype image.

That particular prototype served four computer labs, about 120 workstations. After I reimaged these four labs I merrily went on my way to the next labs, not knowing the spike in stress I was about to encounter.

An email came in from the help desk. Internet’s down in a computer lab. Students can log in, but they’re getting an error message in the browser. No university portal. Multiple labs reporting the same thing. Then I got a phone call from the help desk. Voicemails. In-person visits from student help desk employees. I was in a different lab across campus, not checking my email or voicemail. Once I got back to my office, I saw the sticky note on my desk, the blinking light on my office phone signaling a voicemail, and the numerous emails with the subject “lab internet down.”

I headed to one of the affected labs, sat down at a workstation in the back of the room so I could watch students’ screens without drawing attention, and saw every single one of them log in and land on a browser error page. I logged in myself, saw the error, looked at the URL in the browser settings, and noticed the extra letter in the .edu address.

I groaned.

The internet was working fine. The startup browser was delivering a dead location. 120 workstations, all showing the same wrong URL, all creating confusion for a growing number of students.

I closed my eyes. My mind raced through options. Close the labs, update the prototype image, upload it to my server, reimage every lab again. That would work, but it would mean kicking students out. I avoided that whenever possible. Disrupting their academic work because of my mistake felt like compounding the error.

Then I saw the solution in my mind.

In Windows Explorer, using my admin credentials, I could type a UNC path into the address bar, something like \LabComputerName\C$\All Users\Startup (it’s been over 20 years and my mind is fuzzy on the exact pathname), and I could remotely access another workstation’s startup folder from the one I was sitting at. I could right-click on the browser shortcut, select Properties, delete the incorrect character in the URL, click OK, and things would work correctly for the next person logging in.

I had 119 workstations to fix across four labs. So on the 27-inch monitor in front of me, I set up four Windows Explorer windows, one in each corner, and started hyperclicking and typing like a maniac. Workstation by workstation, folder by folder, right-click, Properties, delete one character, OK, next. Four at a time.

Ninety minutes later, every workstation in all four labs was fixed. I emailed the help desk from the lab workstation: user error, my bad, and here’s how I resolved it.

I made it back to my office, collapsed into my chair, put my head down on my desk, and quietly admonished myself for doing such a stupid thing. The whole mess started because I didn’t verify my work before uploading the prototype image. One keystroke. One character I didn’t catch cost me ninety minutes of frantic repair. This was something the Council of Wraiths cast a guilty verdict on me. This was something I imagined all the other IT professionals at the university, if they found out, would sneer at me. I didn’t report this to my manager because I was afraid of a loss of confidence in me due to human error. I didn’t tell my co-workers. I kept this goof, emphasis on oof, inside me.

I think about that foul up sometimes. The systems we build are only as reliable as the person operating them. Great bumpersticker slogan. You can automate 90 minutes of reimaging and feel like a wizard, and then one wrong keystroke reminds you that the wizard is still just a person who types things incorrectly at the worst possible time.

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After spending 30 years in IT, I love trying new technology. When I read about a unique software application or a self-hosted alternative to some subscription service, I feel an immediate urge to set it up. I want to see how it works. So I install it, configure it, get it running, and for a few days or weeks, I feel the satisfaction of a new tool doing something well.

Then the friction starts.

A new update introduces a feature I don’t need. A pop-up notification appears to inform me of a premium subscription and its features. The tool still technically works, but it’s asking me for something now. Time, attention, troubleshooting. A quiet cognitive tax of knowing there’s something needs to be messed with. Recently I’ve started asking myself a question: is this software tool serving me, or am I serving it?

I’m betting most people never ask this question. We’re conditioned to hoard software, but never curate. Every conference talk, every blog post, every vendor pitch is about what to adopt next. A new platform. An app that will streamline something you’re currently doing and cook you breakfast in the morning. More software applications on the computer, more capability to do things better than the old way of getting things done.

But nobody talks about what all that software cost you.

Every app you install is an agreement for performing maintenance in the future. Every subscription is a recurring hit to your checking account, even if the amount is small. The accumulated friction of keeping your installed software running begins to reach a point where the list grows unmanageable, pruning and uninstalling becomes important, but the overwhelm of that process either leads to denial or deferment to “someday.”

I have a slim personal technology landscape. At home I run a headless server that does a few specific things. Less than five. I don’t need an App Store full of tools running in the background. I have a smartphone with 17 apps installed. I own a mid-range laptop with a clean bookmark bar. Every Sunday afternoon or evening I audit what I’m running, what I’m paying for, and what I’m maintaining. With some quiet music playing in the background, I ask the same question every time: is this still essential to have in my life?

When the answer is no, I uninstall. Gone are the days of keeping an app on my device “in case I need it later.” All that software is a low latency form of friction. It sets up shop in my mind as I’m visualizing my financial account balance decreasing $5 a month...and $60 a year. For a software application not launched, not fiddled with, not giving me any results.

When the answer is no, and I uninstall, eight times out of 10 I don’t miss it. Those other two times, the app is easily reinstalled to resume development and use.

Here’s where my fight with friction gets counterintuitive, perhaps hypocritical. I’ve written in past essays about friction as something valuable. I enjoy an iPod classic music player that requires more effort to operate than a streaming service. My reading workflow has more steps to it than simply touching an app. That is a deliberate form of friction to separate deliberate focused enjoyment from mindless consumption. I go through this form of friction on purpose because it slows me down and forces me to choose.

The difference in friction categories: when a software tool that’s supposed to work in the background starts demanding my attention, that sort of friction isn’t adding value for me. It’s just one more brick in the backpack. Eventually I notice the weariness from carrying around too many bricks.

I am a curious nerd. I gladly dedicate an hour on a Saturday afternoon meant for rest and recreation and immerse myself in the ins and outs of a new software application. I like going through the process, the deliberate knowledge dive where I emerge with my own mental list of pitfalls to avoid with this software, and benefits of use once it’s set up. This is also valuable when my clients ask me about wanting to do something with their tech, or eliminate something from their own tech landscape. More and more I’m encountering people wanting to distance from the big tech companies. What can I recommend that might be of use to them? I’ve already got three or four candidates in mind based on past installations and trial periods. But what my clients don’t know is that I have a ruthless discipline in pruning software. And most importantly, what applies to me and my tech life does not necessarily apply to others.

Sadly I watch software hoarding happen in the educational technology realm often. A department adopts a tool to solve a specific problem. The problem gets solved, and the tool stays. Three years later, someone new is maintaining it, nobody remembers the original problem, and the tool has become part of the landscape. No one questions if the tool is still relevant because, “we’ve always done it this way.” Technology professionals are especially bad at this, and I’m just as much to blame. We’re wired to be problem solvers. We see a need and we reach for a tool. But my technology house isn’t built by filling every room with furniture. It’s built by knowing which rooms stay empty.

More later...

I’d landed my first management position, IT manager for one of seven colleges at Western Washington University, and the learning curve was steep. Four servers, three computer labs, network shares on Active Directory, and over 120 faculty and staff clients. All by myself. No staff. The two people who could have helped, my predecessor and a peer IT manager, weren’t in a charitable mood to assist someone new to the role. So I had to figure it out alone. Budget landscape, infrastructure, the daily avalanche of “my computer won’t” from faculty who didn’t know my name yet and didn’t care to learn it.

I asked the Dean’s Office for staffing. They told me there was no budget for FTE or part-time employees, but I could hire work study students. The federal student aid program would cover the compensation. Not much more guidance than that. I cold-called Financial Aid, the Registrar’s Office, anyone who might point me toward the right person. Eventually someone emailed me a link to post a job description. I’d never written one, so I found other postings on the site and borrowed the professional language until it sounded like I knew what I was doing. Basically, I needed students to handle tier one computer issues while I focused on the more complex work.

I posted the description. And waited.

Two days later, an applicant. An undergrad in a non-technology major. I scheduled the interview and spent most of it asking who he was as a person. His professional demeanor struck me immediately. Quiet, kind, mature beyond his years. I believed then, and I believe now, that I could train almost anyone to troubleshoot a computer issue. What I couldn’t train was character. I needed someone with solid people skills, someone who was teachable, and someone I’d actually enjoy sharing a small, one-room IT office with for a couple of hours a day. He checked every box. I hired him on the spot, starting the following week. I needed a couple of days to figure out the paperwork to process a work study hire, but I kept that part to myself.

Two weeks later, another applicant. Another non-tech major. She was outstanding. Completely sparkly in demeanor, eager to learn, and exactly the person I’d want greeting a faculty member who just came storming in because their classroom podium computer stopped working. I hired her on the spot, starting the following week.

A third applicant followed soon after. Computer science major, quieter in personality, but I could see the technical depth immediately. I thought he’d make a great peer teacher to the first two, someone who could explain the why behind the fix. I hired him on the spot, starting the following week.

A few weeks later, a fourth applicant. Another technology major, funny, a bit brash without being eyebrow-raising in a professional environment, strong technical instincts, and someone I could tell would be a good fit for the work. I hired him on the spot, starting the following week.

I had assembled my four Aces.

I built a rotation schedule. Each Ace worked a two-hour block when they weren’t in class, which gave me nearly half a day of student support coverage every workday. I set clear expectations: show up for your shifts, dress professionally, and if you have a quiz or a final that conflicts with a work shift, tell me ahead of time. Their academics came first. I would not let my IT support needs supersede their classwork. That was a non-negotiable.

In those early weeks, I walked them through the tier one landscape. Here’s what you’ll encounter. Here’s how a non-technical faculty member might describe the problem. Here’s how you resolve it, often in their office, on their turf. My Aces learned it the first time. I didn’t have to repeat myself. One of them created a guidebook documenting the steps for future student staff without being asked. Very enterprising, indeed.

I held monthly staff meetings with all four, closed door, no drop-in clients. I asked how the work was going, what concerns they had, what issues they were seeing from their perspective, how I could be a better manager to them, and how their classes were going. I got to know their personalities, the way they interacted when two of them overlapped in the office at the same time. It was the kind of team I didn’t know I could build because I’d never been given the chance in the past.

Then the moment arrived.

A tenured professor wandered into the office, walked right past my student staffer’s greeting, ambled up to my desk, and announced they had a computer problem. I asked my Ace to accompany the professor back to their office to take a look. I knew they had the skills.

The professor looked at my student and said, “Oh, I see you have minions helping with tech support now.”

I didn’t look at my Ace. I stood up from my desk. Slowly. I looked down at the professor, who was considerably shorter than me, and I enunciated every word with deliberate calm.

My student staff will not be referred to as minions. They are my employees, and I am proud of them. They are students of Western Washington University, and they will be referred to with dignity and respect. You are obviously unaware of how talented my student support staff are. They are my Aces. I have full confidence that they will be able to assist you with your computer need.

I held the professor’s gaze. Lingering silence. On purpose.

The professor was rattled. They hadn’t expected a public rebuke. But they had no recourse. They told my Ace to follow them, trying to regain some control over their situation, and left the office.

Five minutes later, my Ace came back, smiling. Issue resolved. I asked them to close the door.

“I apologize on behalf of that professor for the insensitive way they referred to you. You, and your fellow support staff, are very talented, and I am very proud of the work you do for this college. Don’t ever forget that.”

They thanked me. I changed the subject and moved on to a tech issue that had landed in my inbox. We had work to do.

After two or three months on the job, my Aces were handling the front line. They’d ask me clarifying questions when the nuances of a situation were unfamiliar, and I gladly walked them through it. I tested the waters with hour-long meetings away from the office. No crises when I came back. They wrote down the details of drop-in visits while I was gone, and we took care of them together afterward. I tested again with doctor’s appointments that took me off campus for two or three hours. My Aces were piloting the ship.

Eventually, I saw a day on the schedule where eight hours of Aces coverage lined up across the workday. I sent an email to all college personnel letting them know I would be taking a Thursday off, and my four student employees would be providing IT support for the college in my absence. By then, my clients recognized the faces in my office. They were used to these students visiting their offices to troubleshoot problems. It was a normal Thursday for my Aces.

For me, it was something bigger. I was letting go of the reins on a support standard I had built for myself as the sole IT employee for the college. A standard nobody asked me to maintain at that level. A standard that existed because I couldn’t imagine anyone else caring about my clients the way I did. My four Aces proved me wrong, and I was happy to see this.

Naturally, my students didn’t stay forever. Two Aces graduated, and I took all of them to lunch to celebrate the graduate and thank them for their work. One Ace found a work study position in the Computer Science department that better aligned with where his career was heading. I took him and the remaining Ace to lunch, too. And after two and a quarter years as the college IT manager, I got hired into my current role as the university’s Canvas LMS Administrator. I let my final Ace know I wouldn’t be their manager anymore and gave them the option to stay on under the Dean’s Office until my successor was hired, or pursue other work study positions with the university.

No reunion scene. No final team huddle. Just enjoyable lunches off campus, quiet but meaningful thank-yous, and five people heading in five different directions.

I’ve managed projects since then, but I’ve never managed people. I think about that sometimes. Four students who weren’t looking for careers in technology support taught me that the methodology I’d been practicing with clients worked just as well with a team. Read the person. Hire for character. Teach the rest. Protect them fiercely. And when they’re ready, get out of the way.

More later...

My Muppet spirit animal is Sam the Eagle. The stern one. Arms folded, brow furrowed, categorically disappointed in whatever just happened. Reserved, rule-following, allergic to nonsense, quietly certain the room would run better if everyone would settle down and maintain mature decorum. That’s me. At home I married a Janice, all peace-sign serenity and go-with-the-flow, because apparently an eagle only relaxes in the company of someone who has never once been tense. And at work, in Canvas-land, I have a long-time colleague whose spirit animal is Fozzie Bear crossed with Gonzo.

He’s a decade younger than me, so his pop-culture references live in the ‘90s and mine never left the ‘80s. He also knows more about technology than I do, which I have no problem admitting because I left the I-know-more-than-you competition among IT professionals a number of years ago. The high school bench press contest about knowing more about computers than your peer got too performative for me. He’s an instructional designer at the university. Where I am a yellow belt in content accessibility, he is a black belt. He is a Zoom czar, a Panopto ninja, and an entertainer who has never met a room he couldn’t warm up in a minute. Where I observe, he radiates. Put us in front of a group and we are a dynamic duo.

We meet most of our new faculty the same way, at the university’s annual New Faculty Orientation. Every year WWU hires 20-some new professors, and every fall season a fresh batch files into a room, some brand new to Bellingham, most brand new to Canvas, and nearly all of them quietly apprehensive. They’ve lectured brilliantly for years in fields that have nothing to do with a learning management system, someone has just told them to move an entire course online, and they’ve arrived braced for the version of this meeting where a boring, condescending IT guy makes them feel stupid.

They don’t get that. They get the act.

It opens gently. We introduce ourselves as the starting point for anything technology at the university, not just Canvas. As my partner likes to put it, “Chances are we know who’s who at the zoo who can help you with your computer issue.” Beat. “Hey. That rhymed.” Small laugh. Then somewhere in the first 30 seconds one of us promises to get their course all fixed up so we can get them to happy hour sooner, and there’s the first real crack in the ice.

From there it snowballs, because my partner is a hype man, and a hype man is exactly what a Sam the Eagle like me needs.

Here’s the thing about me: I will not sell myself. I find self-promotion incredibly uncomfortable, the verbal equivalent of wearing someone else’s shoes in the gym. Telling professors about how much I know about Canvas feels like boasting, and boasting is against eagle policy. This is a genuine professional problem for me. Nobody hires the quiet guy...they don’t know he’s not only competent, but is an absolute Ace with computers.

So I outsourced it. My partner gladly extols my virtues to anyone who is within earshot with his projecting voice, and I return the favor for him with a more focused, quieter tone. Between us we solved the boasting problem by never boasting about ourselves, only about each other.

It sounds like this. Someone asks about Panopto, the video platform we have available in Canvas, and I’ll say in my best Doc Holliday from Tombstone voice, “When it comes to technical issues in your Canvas course, I’m yer Huckleberry.” Then I hand over the praise. “Now, with Panopto, I’m a yellow belt. I’ll throw spaghetti at the wall and might eventually get your videos showing up for your students.” Then I point at my partner. “Him? He’s a black belt. He’ll hand you a proper plate of pasta in half the time. With tasty marinara sauce!” And he’ll immediately chime in that I’ve rescued more courses at 7:30 a.m. during finals week than he can count. Now the professors are looking at two people who clearly like each other, clearly know what they’re doing, and are, contrary to initial expectations, fun! The anxiety drains out of the room. By the time we stop riffing, the new faculty know exactly who to call for what, and they learned it with a giggle.

Then a break comes in the orientation retreat, and the real work starts. This is the part nobody expects.

During the break, one professor peels off from the group and approaches us. The unassuming one. The one who’s been quiet because they’re the most nervous person in the room. And they get a front-row seat to what happens with the act. My partner stays exactly himself, warm, upbeat, chitty-chatting, active listening at full wattage. It’s perfect, because an anxious person needs to feel welcomed and safe before they can feel helped. But I remain quiet. My posture sits back and I read them. Outgoing or introverted, like me. Braced or thawing. And when he tosses the technical question my way, I skip the huckleberry routine. I say a few sentences, quietly, aimed at that one human being, something true and encouraging and calibrated exactly to the person in front of me.

A new professor once told us they were convinced that moving years of lectures online was a mountain she couldn’t climb. My partner lit up and rattled off five things Canvas would do that were going to save her minutes or hours of time. And because he’s him, he concluded with, “...do this, this, this, then this. And Chuck Norris is your uncle.” She laughed. Then it was my turn to continue quietly. “Please don’t think this is a one-and-done consult,” I told her. “Think of us like a chiropractor. The first visit is the big adjustment. We crack everything into place and you walk out feeling better. Then we do a few follow-ups a couple weeks later, when you have the time in your schedule, to fine-tune the other aches and pains. We’ll walk with you through the whole first quarter. The midterm spike in grading, the week before finals when everything feels like it’s on fire. You’re not alone with this.” She didn’t need another reason to contact us, she needed to know we weren’t going to vanish like most techs. That’s what the quiet part is for.

The act isn’t the point. The act is the door which opens into a comfortable room where a person can actually ask for help. The jokes and the happy-hour one-liner and the black belt bit exist to lower the defenses of an uncertain room just enough that one person feels safe enough to walk up during a break. Then the volume drops and the real thing happens, quiet, one-on-one, calibrated, human. My partner gets them in the door. I meet them once they’re through it. Loud reaches the crowd. Quiet reaches the person. Neither of us could do the whole job by ourselves. A relational technologist doesn’t flourish as a lone wolf. This unique work requires other people in your arsenal, someone whose strengths cover your blind spots, someone who’ll say the good thing about you that you would never say about yourself. Together we cover the entire gamut from a cautious, defensive room to a professor who knows they’re in good hands.

The faculty leave orientation knowing our names, our faces, and our two very different personalities. The enthusiastic one and the quiet one. The black belt and the yellow belt. The Gonzo and the Sam the Eagle. Most of all, they leave knowing that whatever goes sideways in their course hours before their final exam, somebody who already made them laugh is going to be there. And an eagle, it turns out, can be very good company, as long as he brings his hype man.

More later...

There’s a council that meets in my head. It’s been in session for 30 years.

I picture them as hooded figures in black robes, seated in a half-circle, arms folded, faces I can’t quite make out. They don’t speak so much as radiate. They convene whenever I’ve done something, and they hand down their verdict before I prepare my defense. The council never adjourns. They’ve been in session since I was in my 20s, and they are very, very good at their job.

I wonder if others have some version of what goes on in my mind. A jury they never asked for, made up of their own worst moments. I gave mine a name and created a visual image of them, because it turns out I can’t fight something I can’t picture in my mind.

Here’s what I’ve learned about my ominous council. Every wraith on it is a failure from a single decade, my 20s, the years I did most of my falling. I lost my father when I was 21, and all the guidance and mentorship I needed as I entered adulthood went with him. I spent the rest of that decade adrift, making the kind of mistakes a person makes when nobody ever taught him the things you’re assumed to already know. The council assembled in those years. They’ve been in their seats, evaluating me ever since.

I have had many verdicts given to me by this council. Three in particular are tough for me to put in the rearview mirror.

The first verdict is about money. By the time I was 28 I was sitting in a house I had no idea how to maintain, holding a five-figure hole of debt I’d dug without ever lifting up and out of a pursuit of things. Credit cards. A line of credit against a home. A budget never balanced because no one ever told me a budget was a thing you balanced. Exactly one other person on earth has ever known the size of the hole I dug.

So now, every single paycheck, my wife and I move money into savings before we do anything else with it. The council takes credit for that verdict, pointing bony fingers at me and reminding me to never dig that hole again. That financial mistake turned into a discipline, and I’m quietly serving a life sentence for it. Ironically, the council of wraiths provided wisdom on me which they always take credit for.

The second verdict is the one I’m gradually overruling, but it’s taken a lot of time to do so.

At the turn of the millennium, tech jobs were everywhere in Washington state, particularly Redmond, Bellevue, and Seattle. I’d look at the postings, ones that would have changed the whole trajectory of my career, and I’d tell myself something I can still hear decades later: “I’ve got a comfortable life in Bellingham doing desktop support for the university.” And then I’d close the browser tab. I never applied for any of those positions.

You might have missed the impact of that last sentence. I didn’t apply and get rejected. I rejected myself, in advance, so that no hiring manager down south ever got the chance to. The council reframed my inaction as contentment. The wraiths did what they do best, not protect me from failure, but prevent me from finding out the “what if.” That’s the verdict I can’t quite forgive myself for. I eventually paid off the financial debt, but this one I’ll never get to know the answer to. I might have had a whole different career awaiting me on the other side of an application I was too afraid to submit, and that not-knowing is permanent.

The third verdict is still under appeal.

There’s a kind of room I don’t walk into anymore. Live hard rock music that is ear-shatteringly loud. It’s the sort of show I actually love to be in. A packed bar or club with the wrong energy running through it. I had to hit the brakes on attending rock shows after one particular night in my 20s when someone got under my skin. I discovered in real time exactly how much physical power I had. It scared me. So the council handed down a life sentence. Never again, never that room. I defied their verdict a few times in my 30s and 40s, but I never felt that excitement and internal joy from my 20s again. I could never fully immerse myself with the joy of a rock show because that council was in my mind the whole time shaking their heads noticeably in the hooded robes, fingers tapping on their folded arms. It’s like I could hear their “tsk, tsk, tsk” over the crunchy guitars and thunderous drums.

I’ve been wondering whether a man in his 50s is really the same man who lost his grip that night. The council of wraiths insist he is. They always insist, there is no possibility of the contrary. In my quieter contemplative moments I am noticing they don’t always get the last word on who I am now based on the worst thing I did back then. That case is still pending. I haven’t ruled on it. The big difference between now and then is that I’m the one holding the gavel. Not the wraiths.

There are other cases on my docket that will never be entered into the public record. A few verdicts I keep serving quietly, without complaint, that sit between me and one other person. Not everything the council holds is for you. A man’s allowed a sealed file or two.

Here’s why I’m writing any of this down at all. For over 30 years I permitted the council to meet unchallenged in the dark to deliberate on my life actions and cast judgment on my shortcomings. Sometime after I turned 50, a switch flipped inside me. I started forgiving myself for what was done in the past. I gained momentum publishing my own words under my own name, where anyone can read them and think whatever they think. I stopped caring what people thought of me. Every one of those choices to rule in favor of myself is a case the wraiths would have thrown out before it reached trial. I’ve chosen to overrule some, but not all of them. Some of their verdicts were appropriate, as I mentioned earlier.

There’s one more thing this council handed me, and it took all these years to see it as a gift instead of a wound. Because I know exactly what it costs to sit in that defendant’s chair, I’ve spent my entire career making sure I never become a hooded figure in a client’s head. Every time I choose not to make someone feel dumb, every time I catch the error before it can embarrass them, that’s me refusing to seat a wraith in somebody else’s council. The beautiful work I try to do for the people I serve grew straight out of the ugly frame in my own mind.

The council of wraiths still convenes in my mind. I don’t think they will ever fully disband. I just don’t let them meet in the dark now. I keep them in the light, hoods back, arms folded, where I can see their faces and they can see mine.

More later...

You’ve been with me a long time. Longer than most of the people I work with, longer than any job title I’ve held. Through all the tech support years you rode along quietly, low in the mix, a hum I could mostly ignore while I answered the phone and fixed faulty printer connections and told people it wasn’t their fault. I could live with you like that. You were a passenger. You didn’t grab the wheel.

Then came the season you grew teeth.

About a decade ago I took a two-year detour out of my usual work and into a manager’s chair, running a one-person IT department for a college across campus. That’s when you emerged. Not a hum anymore. You started yelling to the point where it drowned out other voices in my ears. You sank your fangs into my shoulders, right where I carry my power, right where a man holds the weight of the thing he’s trying to build. I’ve carried you there ever since, like a backpack I never take off. Most days you stay zipped in the compartment, wriggling to break free. I know you’re back there. I choose not to reach in.

I remember the day you tried your hardest to damage me. I know you remember it well.

Two months into the job, the college held its fall retreat. It was my first real introduction to my new clients, a full room of faculty just back from summer break, contracts freshly renewed for the year ahead. I got asked to stand up and walk everyone through a system I’d inherited, something the college needed for a review coming down the line, built in-house by someone long gone. My first time in front of these people, and the thing I was there to defend wasn’t even mine. It was a product with my name on it now.

I saw you in the back of the room the whole time. Smirking at me. I watched you lean toward strangers and whisper the words you knew would find my soft spots, because you always knew exactly where those were. The room turned rough on me. When a stranger stands up and starts selling you a tool you never asked for, you push back. Heck, I’d have pushed back too. But it didn’t feel fair from where I stood, taking arrows for something I didn’t make, in front of the people I’d been hired to serve.

You wanted me to return fire. I could feel it coming off you. Lash out, put the room in its place, show these people who they were dealing with. I didn’t give you that. What I gave the room instead was a sentence: “You raise some very important questions. Let me meet with you after the retreat, somewhere quieter, and we’ll talk through every concern you’ve got.” Even humiliated, even with your teeth in me, I reached for the relational move. I was doing this work before I had a name for it. You hated that.

My presentation was scheduled right before lunch. I couldn’t eat afterwards. I couldn’t stand in the buffet line making small talk with people who’d just lit me up. I couldn’t look at my new clients and see anything but unsafe adversaries. So I walked out of the conference facility to the parking lot and sat in my car with the door locked, the windows rolled up, and my eyes closed. I almost started crying, but I didn’t. I had never experienced this amount of embarrassment, Anger. I blame you for it. In the silence of my car, I asked myself if I should quit. It was a lot of negativity to swim against, two months in. I stayed in my car for half an hour, engine off, just breathing. Somewhere in that half hour I made a decision. I pictured putting on armor, actually visualized it, plate over the soft spots, because those soft spots were real and you knew every one of them. A people pleaser takes a room like that straight to the chest. I opened my eyes, and they narrowed with a new attitude. I got out of the car, and I marched back in for a plate of food.

You know what greeted me at the buffet, Anger. Not “welcome aboard, Chris.” I’m standing there with the salad tongs in my hand and the first words from the first person to reach me are, “Hey, I have a problem with my computer.”

That’s the moment I threw you into the back seat.

Something inside me went still. “I’d be happy to help with that. Send me an email and I’ll come by your office during your hours and take a look.” Courteous, and behind a sheet of hurricane-proof glass. The friendly professional voice that says yes while keeping one hand on the door. More of those computer needs came trickling in that afternoon between sessions, and I gave them the same answer. I walked back into the fall retreat wanting a getting-to-know-you response, but instead I faced a difficult job of surviving the rest of the week.

Here’s what that cost me, though, and I’ve never said it out loud. I came to that college wanting to be known by these people. That’s the only way I know how to work. And you taught me to meet my own clients from behind glass. To lead with the wall instead of the handshake. The wall worked. It got me through a brutal fall quarter. But a people pleaser doesn’t raise a wall for free. You cost me months I can’t get back, months I could have spent knowing them, because you talked me into seeing them as transactions, not people to meet and develop a rapport with.

After that retreat I stopped waiting for the college to feel like home and started immersing myself in the job. I double-timed my learning, mapped the tangle of servers, deactivated software nobody needed that kept firing pop-up notifications at people, and found solid paths through the friction. Then, a week or two later, fall quarter started and the real flood arrived. A four-month backlog from the vacancy before me, every request that piled up while the seat sat empty, slammed straight into the busiest weeks of the academic year. No budget to hire help of any kind. Just me, a backlog I didn’t create, and a calendar with no mercy in it.

So I went hunting. I read about the work-study program, cornered some office staff who didn’t much care for me until they coughed up how to fund students through another line, and I hired four of them. I trained them my way. I tried to be the boss I’d have wanted when I was 19 and broke and standing in someone’s office asking for a shot. I called them my Aces, never minions, whatever a certain kind of faculty preferred. Nine months of hard, consistent, unglamorous work later, I took a day off. I could actually not be chained to my email for a workday, and the Aces would manage the store.

Anger, I built that department while carrying you. I didn’t set you aside to build it. I built it with your fangs in my shoulders the whole time, and I aimed you at the work instead of at the people. I fought you, not my clients. Every faculty member who roughed me up that day, I’ve gone on to build something better, years later, in a different corner of the university. The room that lit me up is full of people I’d now call allies from my seat as their Canvas Admin. You don’t get to keep them as my enemies. And there was one man in that tough season whom you could never turn into a foe, the one I answered to, who looked past the kind of IT manager he’d grown used to and gave me room to be a different kind. We’re friends now. I bet you didn’t see that coming either.

I won’t pretend the years since were sunshine, rainbows, lollipops, and waterfalls. There’s been a long stretch of management that never quite saw me, that filed me under one narrow skill and forgot the rest, that standardized and neglected in the same breath, and you fed on all of it. For a long time you ate well.

Lately, though, you’re fading. Like the photograph in Marty McFly’s pocket, the people in it going lighter at the edges, harder to make out, until one by one they’re gone. The landscape’s been clearing. The people who handed you the most to work with are moving along, and I’ve turned toward something better, toward the clients who send the genuine thank-you notes, toward the work I choose because I know in my heart it’s right and get to watch land with people. You’re still in the car with me. I hear you back there, shouting and flailing, telling me to remember, telling me to stay mad.

Instead of giving you my attention, I turn the stereo up. The client-praise channel, loud enough to drink my seltzer to. And I keep driving. You’re still in the backpack, zipped in, riding on the shoulders where you first bit down. Some days now I go a good long while without remembering you’re back there at all.

More later...

Right now, as I write this, an iPod is playing.

Not through Bluetooth, not casting to a TV, not waiting on a technological “handshake” between two sources that fails twice before it connects. A headphone cable runs out of the jack and straight into a Tivoli Audio Model Two, and the music fills my home office because two physical objects are touching. That’s the whole signal chain. Nothing in the cloud gets to inject an opinion about it.

The iPod is a sixth generation “classic”, gutted and rebuilt. A terabyte of storage on a microSD card where the spinning drive used to be. A logic board that runs Rockbox instead of anything Apple ever shipped. A battery that lasts for days. A dark charcoal felt sleeve some kind soul made to order on Etsy. All in, it ran me about $350, and yes, I know exactly how many months of streaming that buys. I did the math so you don’t have to. I’d ask Star-Lord for a second opinion, but he seems happy with his Walkman, a similar setup.

There’s no rock in Rockbox, by the way. Blues? Plenty. But no rock songs. The name is an inside joke about what I use it for. My inner nerd smirks every time I see the logo flash during its four-second bootup.

Here’s the part that makes people twitch. To play a specific song, I have to work for it. I want Jonn Serrie’s “Gentle: The Night,” so I put my thumb on the wheel and start spinning, clockwise and counter, drilling down through the library until I land on it. Thirty seconds, maybe. Building an actual playlist means holding buttons in sequences that reactivate a trauma I first suffered typing text messages on a numeric keypad, back when the letter C cost you three presses of the 2 button. In 2026 I could summon any song on earth in under a second by talking to a piece of glass. Instead I spin a wheel like it’s 2006. I dig it.

Thirty seconds of thumbing the wheel toward Jonn Serrie is thirty seconds of choosing Jonn Serrie on purpose with intent. The effort-of-thumbs is a small price to pay for my music listening experience. My thumb on that wheel is me voting for exactly what I meant to hear. Every time. The device rewards me as I sit with a whole album the way it was originally sequenced. It punishes impulsive playlist-hopping, which suits me fine, because I never liked playlists anyway.

The effort-of-thumbs comes with a tax, and I begrudgingly pay it with a laptop I’m embarrassed to own. Getting my high-quality FLAC music files onto the iPod means I have to boot a barebones Windows machine that exists for this one job and nothing else. I plug the iPod in by USB so I can copy an album over from my home file server, a Synology Network Attached Storage device. It takes time. I grumble the whole way through. That little laptop is the necessary friction for living off-cloud, and I pay it without complaint, although my teeth grit when several silly popup notifications slide out from the right side of the Windows desktop. The alternative is handing my music listening keys over to someone else.

This is where the skeptics come in, and there are many. My wife is a skeptic. My coworkers are skeptics. People who’ve never met me but subscribe to my newsletter are skeptics. Everyone has an opinion about how I should listen to music, and most of them would like me to hold their opinion for a while, the way you’d hand someone your plate to carry.

I understand the case against me. Any song, immediately. A nominal monthly fee for more music than I could finish in a lifetime. I get it. I just don’t want it, and it took me most of my life to be able to say that confidently. There was a decade where I would have cared what the room thought of my choices. The freedom to not care lives on the other side of that decade, and I earned the right to do my own thing.

So here’s the actual reason I continue to use my modded iPod, the one underneath the price and the friction and the wheel.

My musical tastes make no sense. I’ll play Vangelis into The KLF into Patrick O’Hearn, then swing straight into Five Finger Death Punch and Black Label Society without even thinking about it. There is no rudder an algorithm could ever deploy for my musical preferences at a given minute of the day. And that is the point. A recommendation engine needs me to be predictable. It needs to stick me into a hexagonal-shaped box it can sell against, and my listening life is an Icosagon. (Look it up, kids.) The iPod can hold the unpredictability because it doesn’t care who I am. It just plays the next thing my thumb found. The algorithm can’t deal, because taste that complex won’t resolve into a pattern.

So no, I don’t want the big company knowing what I like. But that’s the polite reason for my offline music device. The more important reason, the one I get loud and obnoxious about, is that the machine stopped watching and started steering, deciding what I should want next and calling it a service. Lately it’s injecting AI-generated tracks into the mix nobody asked for, just to keep the party going. That ain’t curation where I came from. That’s someone subversively taking control of the rudder while telling me I’m still sailing where I want to go.

Every time I press play on the iPod, I hear my music. Not a DJ in the cloud, not a model that claims to know me better than I know myself, not a synthetic song wearing a real one’s clothes. Just the album I chose, playing into a radio, on a device that asks nothing of me but a charge on Saturday night before I go to sleep.

More later...

Think about what lands in a typical IT professional’s inbox on a typical Tuesday.

Complaints. Requests. Escalations. The passive-aggressive “per my last email.” The ticket that got reopened for the third time. The reply-all that should have been a direct message. The URGENT subject line from someone who has never once had an actual urgent situation but treats every situation like one.

Now think about the last time something positive arrived. Unsolicited. From an unexpected direction. About work you didn’t think anyone noticed or cared about.

For a lot of IT professionals, that’s a once-in-a-decade Tuesday.

A few times a year, an institution-wide issue surfaces that impacts my LMS due to another system. The cause is somewhere in the overlap and resolving it requires genuine collaboration. I bring what I know from my side. Someone in another department brings what they know from theirs. They do in-depth research in their own system, run it down, and apply the fix.

The transactional version of this story ends there. Trouble ticket routed. Problem solved. Ticket closed. Everyone moves on. “This is your area. It is affecting my area. Fix this.” No acknowledgment, no relationship, no memory of the collaboration by the following Monday.

I don’t end the story there.

When someone does heroic work on short notice, work that prevented hundreds of my clients from having a very bad day, I find out who their supervisor is. And I send an email.

Not a reply-all. Not a forwarded thread with a quick “great work!” bolted onto the top. A direct, discreet email to that person’s supervisor. Just the two of us. No CC line full of people who will generate a reply-all-fest. I say what the person did, what would have happened if they hadn’t, and how much I appreciated their responsiveness. I let the supervisor decide what to do with that information. My job is to make sure it exists.

The tone of the email depends on who’s receiving it.

If the supervisor is by-the-book, formal, no-nonsense, the email sounds like this: “I wanted to make mention of so-and-so going above and beyond their task list to help me resolve an issue that would have affected hundreds of students and faculty. I am very appreciative of their responsive results, and wanted to share my appreciation with you, their supervisor.”

If the supervisor is a down-to-earth human being with a functioning sense of humor, the email sounds like this: “So-and-so saved my bacon last week on short notice and I cannot overstate how much chaos they prevented. I believe they should get the employee-of-the-week parking spot for their heroic efforts!”

The parking spot, of course, is entirely fictional. At my institution, reserved parking is the exclusive territory of senior leadership. The people actually saving bacon park in the lot with everyone else. That’s the joke. It’s also, if you look at it sideways, my point.

I want to be honest about what I’m trying to do with these emails.

The default communication culture in most institutions flows in one direction: top down. You communicate with your supervisor. Your supervisor communicates with their supervisor. You don’t reach across departmental lines to praise someone else’s employee. That’s not your lane, that’s not your chain of command, that’s not how it’s done.

I think that culture is exactly why so many IT professionals spend entire careers waiting for a Tuesday that never comes.

One discreet email at a time. I’m trying to change that. Not from a position of authority…I don’t have any. Not with fanfare…that’s not my style. Just a professional in one corner of the institution telling a supervisor in another corner that their person mattered last week, and that someone noticed.

That’s not a transactional culture. That’s the beginning of a relational one.

I don’t know what happens after I send those emails. Maybe the supervisor forwards the praise. Maybe they mention it in a one-on-one. Maybe it sits in their inbox and informs how they think about that employee at review time. Maybe the employee never hears a word of it.

But somewhere out there is an IT professional who opened their email on a random Tuesday and found something they didn’t know they were waiting for. Something that didn’t come from their own supervisor, didn’t arrive through official channels, and wasn’t required by any process or protocol.

Just one person, from a completely different department, who thought their work was worth a two-paragraph email to their boss.

I hope it made their Tuesday.

More later...

The realization surfaced a couple of years ago, and I wrestled with the lack of affirmation quietly in the car after a podcast episode ended or during the last set of incline bench press in the gym, compartmentalizing everything the workday threw at me. I mulled it over in the comfortable silences with my wife while we walked the dog after dinner. I was working out how to convince inner Chris that it was okay for work to withhold the trust I wanted.

In previous essays I’ve used the word Consigliere. It entered my mind before I understood it in my internal operating system. I picked it up the way you pick up any good Italian word, more sound than meaning, a little cool on the tongue, always inviting you to wave your hands and land heavy accents on SIG and ERE when you imitate someone speaking Italian. And just for the record, I’m half Italian, half Welsh. The four syllables sat in the recesses of my mind for years. Then I started paying attention to why I’d kept it, and took the word out for a test drive.

I’ve watched Francis Ford Coppola’s The Godfather most of my adult life, and for most of that time I was watching the wrong people. Sonny Corleone, a son of the Godfather, running his mouth in every strategy meeting, emotions out ahead of his judgment. Vito Corleone, the boss at the head of the table, the man everyone came to. It took me six or seven viewings to notice the guy who barely spoke. Tom Hagen, not a blood relative but familia just the same, sat slightly back from the table, present in every scene that mattered, reading the room while everyone else performed in it. He said the least and knew the most. His quiet was never timid. He was cocked and loaded, the most dangerous mind in the room precisely because he spent nothing on being seen.

It’s funny to look back on now. My 20s had their share of dangerous rooms. Bar fights that almost happened, loud rock concerts packed with aggressive guys in black t-shirts and piercings looking to do anything but sit and watch the band. I learned the demonstrative loud one was never the threat. He was a yapping chihuahua. I scanned for the quiet one, the guy watching everything with narrowed eyes, staying out of the conversational melee, the one who would land a huge impact when he finally moved. Little did I know that I was the quiet one in many cases.

Speaking of rock concerts, I play bass guitar, so of course I watched the Consigliere role play out on stage too. Every band tells you the same story about attention. The lead guitarist is Sonny, prancing all over the stage, squirting notes into every gap, impossible to ignore. Vito is the lead singer, out front, the voice everyone came to hear. And Tom Hagen? He’s in the backline on bass, locked in with the drummer, holding the groove, walking the whole song up to the chorus so the big moment lands. Nobody claps for the bass player, but the bass player is also the reason the song succeeds. Take him out and the whole thing goes thin and wobbly and nobody can say quite why. I know this because I used to wear a black t-shirt while playing live that said, in simple white letters, “You would notice if I stopped playing.” Todd Snider nailed the dynamic in Joe’s Blues back in the ‘90s, the way a crowd fixes its eyes on the star up front while its hips answer to whatever the bass is doing.

That’s the role I wanted. Not the frontman. Never the frontman! The one at the back who makes the thing work for the people counting on him.

Back to that recent realization. The trust that fuels me doesn’t come down through the org chart. It comes laterally, one client at a time. The one who slides the credit card across the table after I recommend a device upgrade, no questions about the cost. The widow who gives me permission to back up six years of her late husband’s tangled accounts and trusts me not to lose a single photograph. The professor who started out sure I was useless and ended up nominating me for an award. None of that has anything to do with my job title, my education level, or what any manager wrote in an annual review. People handed me that trust across a table, one room at a time, and it turned out to be the only kind of professional food that ever fed me.

I think I finally understand why trust means this much to me. You don’t hunger for what you already have plenty of. If the institution had trusted me the way those clients do, their trust might feel pleasant instead of essential. It feels essential because it’s filling a space the frame left empty for three decades. I could have let that space turn into a wall. For a while, I did. What I built instead was a role designed to receive exactly the kind of trust the frame was never going to offer.

So Consigliere became the word I use for the work. After 29 years under the common title of tech support, I’ve got a name for the guy in the corner who reads the room, holds the groove, and makes things happen for the people who trust him. It’s the role I’ll be doing on purpose when the institution and I eventually part ways, and it’s the one I was quietly doing the whole time.

More later...

A dollar a minute. That’s where I started in 2011.

I landed on it mostly because the math was easy and I needed a number, any number, to put on that first invoice to Client #1. I wasn’t thinking about my competition and what they were charging, I was thinking about not embarrassing myself on the first try.

That starting rate held for a while. Then my freelance work started expanding, and the pricing expanded right along with it.

Small nonprofits started finding me, mostly through word of mouth. These were worthy organizations that needed IT support but rarely had a line item in their budget for it. I charged them less than my standard rate. Small businesses came next. Real offices with a few employees with overhead were a different category of operation than Client #1 working solo out of his home. I charged those clients a higher rate than my baseline.

Three different numbers. Three different mental calculations running every time a new client appeared in my inbox. Which category is this? What should I charge them? Is this fair to them, fair to me, fair relative to the last client I quoted? It was unsettling to me in a way that never quite showed up on the invoice itself. It showed up in the mental gymnastics, trying to be generous and sustainable at the same time, and never being entirely sure I’d landed in the right place for any given client.

Client #1’s voice was still in my head through all of this. When you charge more, you eliminate the punters. Don’t blink. But his advice assumed one number. I had three, and blinking three different amounts of confidence depending on who was sitting across from me wasn’t the system he’d been describing.

In 2020, in the middle of the masked, uncertain early days of COVID, I decided to lift the needle off the first record I was playing...and put on a new groove.

For what I do, for the service I offer, for the way I treat my clients, I told myself, I am worth significantly more than I’d been charging. Professional services like counseling charge more than that. There are people I might give a discount to for their circumstances, but I found that most clients contacting me have the money. I came up with one number. Across the board. Still no blinking or grimacing when I said it.

I tested it on a new client, someone who’d found me through a word-of-mouth referral with no history of my old rates to compare against. I said the number. They didn’t flinch. It was almost expected, like a real consultant simply charges real money and anything less would have been the surprising outcome.

Well, that was easy enough.

I’ve held that standard rate ever since, and things have been much more relaxed for all involved, particularly due to much less friction with my process. There is only one exception, and it’s not about the client’s category. It’s about the nature of the work itself. If someone calls because they’ve been hacked and need to get their online life back to stability, the work for full immersion in their privacy and security remediation, that work commands a meaningfully higher rate. Not because I’m taking advantage of someone in a vulnerable moment, but because crisis work carries higher stakes, higher complexity, and a higher cost if I get it wrong. The price reflects what’s actually on the line, not who’s asking.

If anyone asks me today what I charge, I look them in the eye with my business face and say it calmly. Just the number, held with the same steadiness Client #1 told me to hold fifteen years ago.

Somewhere in my journey as a technology consulting business owner, I observed something important about the kind of work I actually wanted. The small business contracts, with their multiple stakeholders and shifting priorities and committee-style decision making, never quite fit the way working directly with individuals and solopreneurs did. My introvert self does better one to one. One person, one relationship, one conversation at a time, rather than navigating an office’s worth of competing opinions about what their technology should do.

The invoice evolved because I evolved. Not toward charging more for its own sake, but toward charging fairly, consistently, and without apology, for work I’d already proven I could do well for fifteen straight years.

I’m no longer unsettled about saying so.

More later...

I was nervous walking into that stranger’s home office. It was after my day job ended, no moonlighting on university time, and I was about to invoice an actual human being for my expertise for the first time in my life. I didn’t know what to charge. I landed on a dollar a minute, which worked out to sixty dollars an hour, mostly because the math was easy and I needed to start somewhere. The full evolution of figuring out what I was, and presently am, actually worth is its own story for another day.

What mattered more than the number was the fit. Client #1 and I got along immediately. I admired his former service in the military. He liked my plain English explanations. I understood his sense of humor. He appreciated that I crafted solutions customized to him rather than handing him whatever product the big box tech store was trying to move to clear out inventory for the latest models.

I spent the first 15 years of my career near the bottom of my university’s IT organizational chart. Some upper management and faculty referred to me as, “the help.” But as Client #1 and I discussed options for improving his technology issues, I felt as if I was on the same level with him. And he treated me as a valued expert.

Most of all, he really liked my business card.

On one side, it said: “Sometimes in life you need an Ace up your sleeve.” On the other side, it looked like an Ace of Spades you’d see in a poker deck. My name in bold letters. The job title underneath read “Technology Ace.”

From then on, Client #1 never called me Chris. He called me Ace.

After less than a year into the working relationship, following a few successful victories wrangling his complex technology landscape into something that gave him better control, he did something I wasn’t prepared for. He ordered me, and I mean ordered like a superior officer would in the Navy, to raise my rates.

“When you charge more,” he said, “you eliminate the punters who are looking for a freebie, or who will try to negotiate you down. You stick to the amount you’re charging and don’t blink when you tell them. You’ll attract enough clients. They’re out there, and they’re looking for someone like you to help them.”

He wasn’t just a client anymore. He’d become a mentor on the freelance business mindset I didn’t know I needed, recalibrating my sense of my own worth before I’d had the chance to undervalue myself for another decade while quietly battling impostor syndrome.

There’s a recurring moment in our consultations that always brings a smile to my face. I arrive at Client #1’s home, we sit down at his desk with two chairs, I’m always in the chair for the keyboard and mouse, and we go through a list of items giving him angst, technology problems he’s been quietly stewing over. We go through the list one at a time, and when I fix a particularly onerous one, he’ll lean back and say, “I like it! You’re hired!” Fifteen years into being his consultant, and he still says I’m hired. I like the irony of it. He’s not forgetting we already have an arrangement. He’s re-confirming it, one resolved item at a time, like he’s choosing me all over again instead of just continuing a habit.

The relationship grew the way real trust grows: sideways, into areas not originally discussed. Over the years I helped with his family’s living room technology, televisions, home music systems, digital assistants, car and phone integration, all the accumulated technical bits and bobs of an actual household rather than a single business desktop with a single business software problem.

A few years ago, as Client #1 was contending with some health issues, we had a conversation about what would happen with his technology, more importantly his spouse’s ability to manage it, if something happened to him.

I would be Tom Hagen to his Vito Corleone. Minus the illegal mob boss activity, obviously.

Clients have emerged and clients have drifted over my fifteen years of freelance work. Client #1 is still with me, and is proof that a technology consigliere provides more than solutions to devices.

They’re the Ace up their sleeve.

More later...

In 2011, after fifteen years as a professional technologist at Western Washington University, I’d gotten pretty good at my job providing desktop support to a couple hundred clients spread across numerous departments. I established a solid rapport with many of my clients way before I developed the concept of being a “relational technologist.” I was just an earnest, funny, eager to help young man who wasn’t arrogant or snooty about how I shared my expertise with tech. The rapport I established had many clients viewing me as their go-to guy, saying hi to me outside of work on evenings and weekends. All from recognizing a face that had helped them in a kind way.

I ran into one of those clients on the way back to my office from an unrelated tech support visit. They needed a new phone and asked me what to get.

I didn’t tell them what phone I had and why they should follow my lead. After all, I am an IT professional, right? I am an expert. Everyone should do what I do and do what I say. That’s what most techs believe. Not me. Instead, I asked my client some questions. What phone did they currently have? What did they primarily use it for? What did they enjoy about it? How much were they hoping to spend? Six minutes of a friendly interview, and at the end of it I suggested a phone that actually fit what they’d told me, not what I happened to be carrying in my own pocket. They thanked me for the recommendation, and said something that altered the next fifteen years of my life.

You know, you should really charge money for this advice. People would be happy to pay you for it.

I downplayed it. Graciously, I hope. I’m just happy to help, I said, happy to share nerdy information with people who want it. But the comment stuck with me after work. I thought about it on the drive home. I mentioned it to my wife that evening almost as an aside as I was munching on my dinner salad, and she mentioned that a colleague of hers was a freelance business coach. I knew whom she was referring to because he’d actually asked me Mac questions before. Evidently his own IT support person “only worked on Windows machines.”

I made an appointment to see the freelance business coach in his office. Even though I told him what I was cautiously thinking about, he already knew my strengths. He gave me three pieces of homework: a Washington State business license, a .com domain for a basic business website, and business cards with my name, title, phone number, and email. Back then that cost me about $70 including tax and took about four hours of my time, mostly fiddling with website configuration settings to make it look just the way I like it.

He also had a client of his own already lined up for me. Someone who needed technology support for their business executive consulting practice and was ready to meet with me the moment my homework was completed.

I made a brief phone call to confirm the introduction, verify we had a mutual professional contact in common, and schedule a time to meet at his home office to go over his computer issues.

Did you catch what I just stated? His home office. Keep in mind this was 2011, nine full years before a pandemic would make the phrase “working from home” a universal experience shared by half the planet. Walking into someone’s home office in 2011 wasn’t a normal thing. It was a little odd, if I may be candid. It was a glimpse into a way of working that hadn’t yet become the normal day-to-day that I’ve had for the past six years with the University.

I didn’t know it at the time, but I was beginning something very important in my life as I approached his front door. With fifteen years of being a regular ol’ university employee; predictable, institutional, entirely within someone else’s org chart, I was preparing to enter a stranger’s home office, email an invoice I hadn’t written yet, and hand him a business card that was unlike any other business card anyone had ever seen.

That client became Client #1.

More later...

Nobody is born a monk.

The hooded robe and the Gregorian chant come later in life, not the beginning. There’s a person who lived a life in the world the monk eventually walks away from. There are decades of wanting things, chasing things, believing things would solve problems that things were never built to solve. The vow of simplicity isn’t a starting point. It’s an arrival, and it takes a long road to get there.

Mine started with a different vow entirely.

In 1997, I was twenty-four years old and freshly hired by a university in Bellingham, Washington. I made myself a promise: work five years here, then get a bigger job with better pay somewhere around Seattle. The plan had a deadline and the deadline had a purpose. Bellingham was the launching pad. It was never supposed to be my destination.

When I was twenty-nine, I’d torn my ACL and meniscus playing rec league softball. I told myself it was from over two years of barefoot umping, spinning, and leaping in Tae Kwon Do training that wore the joint down until, after getting my black belt, a quick twist on the softball field finally popped it. With my 30s decade coming up soon, I found myself with a mortgage on a home, active in two or three softball teams on weekends, a decent social life, and a stable job with a twelve-minute commute through a town with water and mountains a quick drive in either direction. I was, by every measure that mattered to me at the time, doing well.

That five-year deadline came and went, and I didn’t even notice.

Nobody asked me to stay in Bellingham. There was no dramatic lightning-bolt event or a single moment of clarity. I just realized what I had, mountains, water, a job I’d gotten good at, a town small enough to know and big enough to live in, and asked myself a question I didn’t know I’d been avoiding: was this enough? The answer turned out to be yes. I spent the rest of that decade and the next confirming it. Medium-size town. Medium-paced life. Visit the big city when you want it. I didn’t need to live there.

But the elusive “enough” wasn’t the only thing I was chasing in my twenties and thirties, and the other thing took a lot longer to figure out.

I spent my bachelor years convinced that things would make me wanted by the single ladies. Wanted, specifically, in the way that leads to a second date. I bought technology I told myself I needed for professional competence, research, staying sharp, staying current, while my credit card balance loudly argued with my story. I socialized with friends who often said, “most toys wins,” and they had the disposable income to win every time. I tried to compete on a budget that didn’t support my friendly competition, because some part of me believed that having enough stuff would eventually translate into being enough as a person, including to the women I hoped might find that version of me worth dating.

I eventually learned that it was never about the stuff. It was about me, whatever I actually brought to a table in a restaurant or a seat at the bar, that made someone want to stay and learn more. The gadgets weren’t doing any of the work to get a woman interested in me. They were just expensive evidence that I hadn’t figured out how to introduce “me” yet.

Somewhere in my thirties, I started figuring it out. The acquisitions of the “new shiny” slowed, and I gained the confidence to stop entering the competition. The devices that remained started getting appreciated on their actual usage benefits instead of on what they might communicate about me to someone else.

That should have been the end of the story. But it wasn’t.

I didn’t notice the shift in where technology was going for a long time. What used to attract me to open my wallet for a new device was the appeal of a tool that could do something nobody had been able to do before. That justified the enormous payment and was worth the credit card balance in my thirties. But somewhere over the following two decades, the bargain quietly flipped. The wonder didn’t disappear, but it got buried under something else: every new device, every operating system update, every account I created required something of me. Telemetry. Access to my exact location when and where I used it. A permanent thread connecting my daily life to someone else’s advertising algorithm.

I kept buying anyway, because the wonder was still technically present, and because by then “staying current” had become its own justification, the same way “research” once was.

It wasn’t until my fifties decade, which started two or three years ago, for the actual cost to become apparent. Not the financial cost, the cognitive one. Every device I owned had become a small ongoing tax on my attention: updates to track, settings to manage, operating system nuances to keep straight across half a dozen pieces of hardware that were each quietly trying to learn more about me than I wanted them to know. None of it was buying back the thing I actually wanted, which was mindspace, room to think, and time for contemplation instead of maintenance.

That’s when the word monastic came into my life.

Where I lived taught me what enough looked like in 2002. The bachelor years taught me, slowly and sometimes painfully, that it was never about the things at all. And technology, last of the three, taught me that wonder morphs into dread if you’re not paying close attention. The cost of not noticing isn’t measured in dollars, it’s measured in the lost moments of quiet you’ll never get back.

I didn’t arrive at Monastic Technology because I read about minimalism and found it appealing. I arrived at it because I spent three decades accumulating, in three different arenas, for three different reasons, and eventually noticed that none of the accumulation had ever once produced the thing I actually wanted. The drive for more went down. The happiness went up.

The monk wasn’t born in a hooded robe. He was a twenty-three-year-old with a five-year plan, a twenty-nine-year-old who noticed the view of the bay at sunset was already enough, a thirty-something who finally understood it was never about the stuff, and a fifty-something who realized his devices had quietly started taking more than they gave.

All four of those versions of me are still present within. But the 23-year-old, the 29-year-old, and the 30-something have gotten out of the way to make the 50-something’s quiet whisper affirmingly loud.

More later...

Two or three times a year, an email arrives that takes over my workday.

A faculty member has suspicions about a student’s quiz performance. The language is careful but the meaning is clear: they think the student cheated. They want evidence. They want their Canvas administrator to arm them with the data that confirms what they already believe, so they can walk into the Provost’s office with a bulletpoint argument that says the Canvas admin said so.

After I read through that email, I’ll re-read it. Then I will get up from the desk in my home office, go refill my water bottle, sit down on my living room sofa, and look out the front window to think for a few minutes. Visualize my steps, remind myself what data I will be acquiring in the next hour. I go back upstairs, sit back down in my office chair, and close every open browser tab. Exit every open software application. The rest of my morning’s tasklist moves to the afternoon.

I’m in CSI mode now.

What follows is an hour, sometimes more, of forensic work that most faculty never see and don’t know to imagine. Canvas page view logs exported to Excel. Hundreds, sometimes thousands of rows of student activity data spanning multiple academic courses. Breaking news: students are on Canvas a LOT during an academic term. I filter everything except the teacher’s course, plus or minus one day from the quiz attempt. I sort by time to build a chronological sequence of activity. I highlight the relevant rows, the ones that tell the story of what the data actually shows during the quiz window, because sending an unfiltered spreadsheet to a teacher and asking them to interpret it is a guaranteed way to cause grey matter to spill out of ears.

There’s a lot in those logs beyond a simple click record. IP addresses. User agent strings identifying the browser, the device, the operating system. Whether the student was on a desktop or laptop browser, a mobile phone browser, the dedicated Canvas Student App. Each data point means something specific. Some log entries carry weight I’m not permitted to deploy without authorization.

The IP address is Personally Identifiable Information for someone using Canvas. I don’t reveal it. Not to the teacher, not in an email, not in a live consultation, not even when the teacher makes a compelling argument that university-owned network data isn’t personal information. It is. I hold the line. Quietly, with a smile, because I understand where they’re coming from, but I hold it.

“I understand your disappointment with the lack of information I am providing about your student’s quiz attempt. However, I will be happy to share this information with the Provost’s Office when my upper management approves it. It’s the best I can offer you for these...unique...circumstances.”

Before any finding goes anywhere, I alert my upper management. I document the faculty request, the nature of the allegations, the data I’ve found. I wait for the green light. I am not a lone gunslinger shooting my mouth off about what the logs infer. I require institutional backing before this moves forward, because if this case escalates to an Academic Dishonesty proceeding, I will have to answer for my findings, and I will not be caught having disclosed protected information or overstated what the data actually shows.

Here is what I will never say, in writing or verbally, under any circumstances: the student cheated.

What I will say, with upper management clearance and only with upper management clearance, is this: “The data in Canvas is showing that the student may have accessed the quiz from a location or device not associated with a dedicated university computer lab, as your quiz settings required.”

May have accessed. From a location or device. That language is doing enormous work in a very small number of words. It’s precise. It’s bounded. It delivers the truth the teacher needs without delivering more truth than the evidence permits or the system authorizes. If the teacher pushes for more, I broken-record back to it. “The Canvas data is showing that...” The sentence doesn’t change. The finding doesn’t expand beyond what the data actually supports. No ad-libbing or conversational riffing for this interaction.

Some teachers accept this. Some push back. Some are frustrated that their Canvas administrator won’t simply confirm the accusation and hand them the smoking gun they came for. Again, I understand the frustration. A teacher who suspects a student of dishonesty is carrying something heavy, a betrayal of the academic contract, a student who may have gamed a system the teacher trusted. Their anger is real and it deserves acknowledgment.

But the student on the other side of those log files doesn’t know I exist. They have no idea that someone is triple-checking Excel rows right now, verifying findings before they go anywhere, making sure the timeline is right, the interpretation is sound, and the language is precise. They’re going about their day, unaware that a finding about their quiz attempt is being handled with the same care a surgeon brings to a procedure: methodical, documented, checked, and checked again.

Because here is what I bring into every investigation request: the weight of what a wrong finding costs. The student’s future degree. A job offer waiting on a clean academic record. An entire future running on a trajectory that one incorrect data interpretation could knock sideways permanently.

I never want to be the person responsible for knocking someone’s life asteroid into a different trajectory.

So I triple-check. I get the clearance. I say “may have accessed” instead of “cheated.” I hold the line on PII even when it costs me goodwill in the professional relationship. I take the high road, not because the policy requires it, but because the student at the other end of the data deserves someone in that process who is taking the whole thing seriously.

Being leveled with means getting the truth. The whole truth the evidence supports, delivered as precisely and completely as the situation permits, no more and no less. It means the person across from you isn’t telling you what you want to hear. It means they’re telling you what they can actually stand behind. And sometimes suspicions and gut instincts are shown to be incorrect.

This is the seventh thing every client deserves. It’s the hardest one to give.

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People can only know what they’ve been given.

I’m a private person outside of my work and my public hobbies. The inner workings of me aren’t on display by default. I don’t have bobbleheads or other posters of sports teams in my Zoom/Teams background, nor do I wear attire with labels or companies. So when someone I know from a social setting sees me and asks if I’m still playing softball, which was a hobby from two decades ago, I don’t take it as a slight. That’s what’s in their mental rolodex. Softball. Brown hair. A younger version of me diving for a blooper in left field on a Friday evening. I smile and tell them that was a fun season of my life, but my body now can’t survive what I used to put it through on the field. We laugh. Small talk ensues.

Or someone who knows me from seeing me on stage at church will ask if I’m still playing bass. And I’ll tell them yes, about one Sunday a month, I always enjoy that opportunity. And then I’ll ask what’s keeping them busy nowadays, an open-ended question designed to avoid the “fine” response, and we’re off and running with another relational technology interaction.

But here’s what I notice: most people stop at what they were given. They file away the one thing and that’s their index card about me. Softball. Bass guitar. Computer guy. We’re all carrying thousands of cards of the people in our lives and the filing system in our brains has limits. But stopping at the first entry means the relationship stays exactly as thin as the day it started, no matter how many years pass.

I can’t seem to stop at the first entry.

In social settings I ask the follow-up. In professional settings I do something that probably has a clinical name but I’ve never looked it up: I keep a mental rolodex on my clients. Not the technical stuff that lives in the ticket history. Other stuff. The sabbatical they mentioned in passing in a previous consult. The peer review assignment they’d never set up before and were clearly unsure about. The comment dropped mid-consultation about a difficult semester with academic integrity issues that was weighing on them while we were fixing their gradebook.

I file it in my mind. And I carry it.

This makes me something adjacent to an unlicensed quasi-counselor, which is not a credential that appears on my email signature but is an accurate description of what happens in the course of sustained technical support work. When you sit with someone repeatedly in moments of low-grade crisis, when their technology isn’t working and the stakes feel higher than they probably are and they’re talking while you’re troubleshooting, they tell you things. Not always intentionally. Often just as the pressure valve releases while the problem gets fixed. And you learn interesting things about people that way, if you’re paying attention.

I’m always paying attention.

So when my calendar shows a consultation with a client I’ve worked with before, my mind does a quick recall. Not of the ticket history, of the person. What do I know about them beyond their Canvas issue? What did they mention last time that I tucked away?

The client enters the video meeting. I greet them, ask how their week is progressing, and then I stop things.

“First things first, how did your sabbatical go? Didn’t you take fall term off?”

There’s a pause. I can see it on their face even through the small rectangle of a video window. They’re asking themselves a question: did I tell Chris about that?

They did. In passing. Last academic year, maybe, mentioned almost as an aside while we were proactively optimizing announcement publish dates. It wasn’t a significant disclosure on the conversational marquee or something they’d expect a tech to retain.

“Thanks for asking. It was great.”

And then they tell me about it. I listen without interrupting, ceding the floor completely, supportive and encouraging and genuinely interested. A minute or two of their recap. Some time away from teaching, whatever it gave them. And then I ease us back toward the reason for the meeting.

“That sounds like a really recharging experience. I’m living vicariously through you! All right, let’s talk about your Canvas courses. I see in the calendar invite you wanted to discuss your gradebook settings.”

Or I’ll remember that our last consultation covered peer review assignments, something they’d never configured before, and I’ll open with: “I remember from our previous visit that we talked through peer review assignments. How has that been working for you?” And the answer tells me whether the learning held, whether there are follow-up questions they didn’t know to ask yet, whether the guidance I tried to offer last time actually landed.

The pause is the thing I think about most. That half-second where the client asks themselves whether they told me. Because what that pause is really saying is: I didn’t expect you to remember.

And the fact that they didn’t expect it tells me everything about how rare it is.

Being remembered is a decision to treat the incidental details of someone’s life as worth keeping. It’s an acknowledgment that the consultation doesn’t end when the screen share closes. It’s an understanding that a client isn’t a ticket with a face attached. They’re a person coming off a sabbatical, or having a difficult semester, or nervous about a peer review assignment they’d never configured before, and they mentioned those things to you, and you were there actively listening with genuine interest.

The mental rolodex only holds what gets filed in it.

File more.

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I am an Enneagram 1. The improver. The optimizer. The person who cannot be in the vicinity of a system not running at its best without having a compulsion to fix it.

This is an excellent trait for a technology consigliere. It is a less welcome trait at home, for my wife’s iPhone. She often has to assure me it is working just fine and does not require reorganization, optimization, or an unsolicited audit. I must confess she’s had to tell me this more than once. My wiring doesn’t always distinguish between a client’s Canvas course and a spouse’s home screen, and it has taken diligent work to unleash the optimizer only when invited.

Fortunately, I’ve had thirty years of invitations from clients to improve their technology.

Here’s how my mind works during a support consultation: My client arrives with one issue. A broken gradebook. A missing assignment. A quiz with settings that can’t be set. That issue is the hub. But the moment I’m inside their course, the optimizer in me activates and spokes start radiating outward simultaneously. Assignment group percentages that don’t align with what is stated in the syllabus. A final exam still hidden from students four days before it’s due. A course with a start date but no end date, sitting in students’ dashboards like a ghost that doesn’t know it’s supposed to have moved on.

My client doesn’t see any of this. Their mind is a single line originating from the original problem. Mine is a hub with a dozen spokes, each one representing something that is either wrong now or about to be wrong later.

The easier path is to fix the gradebook, confirm it’s working, close the meeting, and move on. Most technologists take that path. They’re not wrong to take it; the job description doesn’t require noticing the end date. Nobody assigned them that task. The ticket didn’t mention it. Scope is the ticket, and everything outside the ticket is someone else’s problem or the client’s problem to discover on their own later in the term, probably at the worst possible moment, probably while students are emailing them about it.

But once you notice it, you have a choice. I’ve arrived at a place where I know when to deploy the optimizer in me. But it wasn’t always like that.

Early in my career I made the mistake of mentioning everything I noticed the moment I noticed it. The response was rarely gratitude. More often it was the glazed expression of someone whose brain had already reached its technology capacity for the afternoon and was now being handed a second invoice when they’d only budgeted for one. I learned quickly that a client contending with one active problem has exactly zero bandwidth for a second problem, even a future one, even one I can fix in twenty seconds.

So I made a rule for myself. Fix the primary issue first. Everything else gets a mental bookmark.

The consultation proceeds. We work through the original problem together. I keep the bookmarked spokes in peripheral vision but I don’t mention them or let them distract from the single line my client is following. When we arrive at the fix, when the gradebook scores are aligned with the syllabus percentages or the assignment is visible or the quiz is publishing correctly, I ask: “I think we’re lookin’ good now. How are you doing?”

They respond with a relieved or pleased tone. Everything looks good. Thank you so much. I really appreciate your help.

I can hear them mentally wrapping up. And that’s my cue.

“May I make an observation about your course?”

Almost always I’ll get a yes unless they are running late for a meeting. The primary crisis is resolved, they’re relaxed and feeling good. What else you got for me, Mr. Fix-it?

“When we were in the course settings page earlier, I noticed something that might create some unwanted confusion down the road. May I show you what I’m referring to?”

Another yes. I navigate to the course settings and wiggle my mouse around the start date with no corresponding end date.

“I noticed there’s an earlier date set for when students can access the course, which is totally fine. But without an end date, your course won’t auto-conclude at the end of the term. It’ll stay in your students’ dashboards indefinitely.”

I pause a bit to let it sink in, then I continue with the normalization.

“I usually get a handful of emails at the start of each new term from students asking why an old course is still showing up in their dashboard. In every case, once I add the end date from the previous term, the course immediately disappears from all enrolled students’ dashboards. And I never hear about it again.” A small smile here. “Takes about twenty seconds.”

I look up the end-of-term date. I fill it in. Done.

“Now I think we’re doing better than before.”

The response is always positive. Not always effusive, because the client is processing something that didn’t feel like a problem thirty seconds ago and now feels like a near miss. But positive. Grateful. Slightly relieved in a new way.

What I just gave them wasn’t part of the appointment. They didn’t ask for it, nor did they know it wasn’t even a problem. But somewhere in the next few weeks, when that end date quietly does its job and no confused students email their teacher, or me, asking why an old course is haunting their dashboard, a small thing will go right that they’ll never know almost went wrong.

That’s what being protected looks like. It’s observing ways to improve the client’s situation and doing the quiet work to prevent additional stress. It’s having your clients’ best interests in mind. It’s not letting them learn the hard way.

That’s the difference between a help desk and a consigliere. One fixes what’s broken. The other finds what’s about to break before you do.

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