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.

More later...

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.

More later...

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.

More later...

Most people enter into a technology support interaction carrying luggage. Not the good kind with roller wheels and telescoping handles. The kind of luggage acquired from years of being put on hold, of being read to from a script, having their problem recited back verbatim as though parroting the problem was a substitute for resolution, and then having the ticket closed before anything actually worked. This sort of luggage makes a person’s neck muscles tense the moment they have to contact IT for anything.

I understand this part of life intimately. I’ve had many jaw-clenching, teeth-grinding frustrations of dealing with a support person speaking at one volume with the boiler room support much louder in the phone call. I’ve closed my eyes and drooped my head in dismay as the script-reader told me they cared about my problem in exactly the way the training manual told them to care. I immediately pick off the hollow professionalism of someone performing helpfulness without delivering it.

So when a new faculty member sends me their first support request and the tone is guarded, or terse, or sounds like someone bracing for disappointment, I don’t take it personally, I view it as an opportunity. I don’t view them as being disrespectful. I am assuming they are protecting themselves from someone like me, a subject matter expert in an institutional IT role. The poster child for every unsatisfactory experience they’ve ever had with tech support has made a lasting impression.

Their email message can have a condescending explanation or steps they tried that didn’t quite solve the problem to avoid me starting from the eye-rolling, “did you turn it off and on again?” first troubleshooting step.

My response to a wary first communique is the same every time. Good morning. Here’s what happened and here’s what I did about it. Please reach out if anything else comes up with your courses. Have a good afternoon.

Clean. Warm. Resolved in one exchange.

I’m not performing kindness. I’m extending respect before it’s been earned because everyone deserves a clean slate, and I know exactly what it cost them to ask for help in the first place. The first interaction isn’t just about solving the problem. It’s about being the exception that starts rewriting a pattern that someone else built.

Sometimes it works. The exterior crust of frustration gets a crack in it. The next email arrives a little warmer. Eventually the relationship finds its footing and the full relational methodology comes online, the follow-up question, the conversational explanation, the shiny fresh juicy apples in the bag alongside everything they asked for.

But sometimes it doesn’t go this way. Not every guarded client is carrying old luggage. Some of them have established a pattern that has nothing to do with prior bad experiences and everything to do with how they move through institutional hierarchies. I spot the difference quickly. The name in my inbox tells me most of what I need to know before I’ve read a single word.

There’s the faculty member who can’t seem to take me out of a mental compartment labeled “the help.” The professor who peppers their support requests with subtle jabs, prefacing questions with, “You probably don’t know the answer to this” while asking someone with thirty years of immersion in the technology they’re inquiring about. The person who arrives twelve minutes late to a scheduled video consultation with no acknowledgment or apology. The person who, after getting issues resolved year after year, continues to bypass me entirely with emails to upper management because the big boss being CC’d on the request might get their assignment settings fixed faster. (Spoiler alert: It won’t.) The director ain’t gonna touch that email. We both know this. But the maneuver communicates something, and I received it loud and clear.

This sort of client gets professional courtesy, a timely resolution, and a standard professional reply. They get exactly what they asked for.

No apples.

They will never know what they’re missing because they never considered the possibility it could exist. The follow-up email doesn’t arrive two weeks later asking if the fix held. The “How are we lookin’? :-)” reply never appears in their inbox. The relationship stays exactly as transactional as they’ve decided it should be. I completely honor their decision to keep it at arm’s length.

Despite what you may be thinking, I’m not petty nor do I hold a grudge. I genuinely wish my clients well. When I see an email from them I’m not dreading the interaction. I’m simply redirecting my mind to what the working relationship actually consists of rather than what it could have been. Some clients get the consigliere. Some clients get the help desk. The difference isn’t my willingness. It’s theirs.

On rare occasions, someone shifts from one category to the other. How this occurs is actually simpler than you might think. I don’t require a gift card to a fancy restaurant. I don’t need a plane skywriting “Chris Is Amazing” over the campus. All I need, heck...all anyone needs, is a genuine acknowledgment of appreciation for the help. A kindness in the request learned way back in kindergarten. A thank you that sounds like a person rather than a formality. That’s the door re-opening, and I walk through it every time without hesitation because I was never the one who closed it.

Every client gets my professional best on day one. What they do with it determines what day two looks like.

More later...

The email arrived with no course name, no section number, no identifying information of any kind. Just a faculty member’s expectation that I would somehow know which of the thousands of Canvas courses in our system they were referring to based on a description that would have challenged a psychic.

I replied professionally. “I’m having a tough time locating your course. Would you please provide me with some specific information about it so I can troubleshoot on your behalf?”

The reply was more of the same. Cryptic. Informal. Opaque.

I replied again. “I still don’t know what course you are referring to.”

The tone in their emails was escalating toward adversarial. They wanted me to assume I knew what was inside their head. This was the early days of my journey as a relational technologist. I was kind and empathetic and conversational, but I required specifics. Neither of us was getting what we needed, and then a one-sentence reply arrived in all caps that I won’t reproduce here, so I made a decision.

I immediately replied in the eighth email of the thread that I was coming over to their office. In person. In ten minutes.

I grabbed my notebook portfolio, slammed the door to my office, and started walking.

It’s a quarter-mile walk across campus to their office. The large technologist in mostly black, taking up more sidewalk than strictly necessary, with a visual expression on his face so angry it made young undergrad students part ways, was having a very loud internal conversation with himself that nobody else could hear. The frustration basketball was fully inflated and I was holding it underwater with both hands, determined not to let it launch up and splash everyone in the vicinity.

The mantra started somewhere around the halfway point.

You will not get upset. You will maintain patience. You will not let things escalate. You will not win a pissing match with a tenured professor.

Over and over. Loud enough inside my head to drown out the part of me that wanted to walk in and explain, calmly and professionally, exactly how a person should communicate with a Canvas administrator when they need assistance. Which would have been the end of any possibility of a functional relationship and the beginning of a very uncomfortable conversation with my supervisor. And my supervisor’s supervisor.

So I overrode it. And somewhere in the last hundred yards, the mantra shifted from a restraint into an intention. Don’t escalate. Learn their way.

I darkened their door, filling up nearly the entire frame. They looked up from a book they were reading at their desk. I smiled and said, “Good afternoon [first name.] Please show me the course you are referring to?”

The hyperfocus activated the moment I looked over their shoulder at the screen. I learned they were using their own informal course name, not the official title in the system. The one I see in Canvas when I search for courses. Keywords I hadn’t seen in any support request before. I filed that in my mind immediately. Then they started describing what they needed. The vocabulary was entirely their own. Roll over instead of import content. Add into instead of cross-list. A private language built up over years of using Canvas the way they understood it rather than the way the documentation described it.

Most people would have corrected the terminology. I made mental notes.

The course issue got resolved. But the more important thing that happened in that office was the construction of a translation subroutine I’ve been running ever since. A unique support method for one client. Their informal title keywords map to the official course name. Their verb choices map to standard Canvas functions. What looks like opacity in an email is actually a consistent internal logic once you have the decoder.

I built the decoder that afternoon. I’ve been updating it ever since.

Subsequent emails from this professor arrived with the usual unconventional diction and I met them where they were. Not my standard brief, professional, just-the-facts response. Conversational. Reassuring. Sideways smileys. :-) Their claws retracted gradually. The tone warmed. A couple more in-person consults brought more familiarity with my particular Sam the Eagle energy and their particular Janice from Electric Mayhem energy, and something that started as friction began to function.

Then one afternoon an email arrived. Subject line in all caps. Urgent. A non-standard course descriptor I wouldn’t have recognized two years earlier. Graded curriculum got deleted by accident. The kind of message that would have sent me down three wrong paths before my translation subroutine existed.

I keyed in on their code words. I quickly located the right course in their dashboard. I restored the deleted quiz and the student scores popped back into the gradebook. I replied: “How are we lookin’? :-)” with a clickable link to their gradebook.

The response came back in all caps.

“YOU ARE A GODSEND.”

I smiled at my screen for a moment longer than I usually allow myself. And then I left my office to go for a quick walk to my happy place on the university campus. A location where you can view the city and the bay. I reflected on where things were with that client and where things are now. I turned an adversary into an ally because I tried to get to know them.

Months later, something happened that I couldn’t have predicted. This faculty member nominated me for a university President’s Exceptional Effort Award. Official recognition. My name on a list of people who had done something worth acknowledging, submitted by someone who two years earlier had been sending me adversarial all-caps demands and expecting me to read their mind across the campus network.

Being known isn’t where relationships start. It’s where they arrive after enough time, enough contact, enough deliberate attention to how a specific person moves through the world. It doesn’t begin with warmth. It begins with friction and opacity and a quarter-mile walk and a mantra you repeat until it becomes an intention.

The pivot isn’t the award. The pivot isn’t “YOU ARE A GODSEND.” The pivot is the moment on the sidewalk when you stop rehearsing what you want to say and start asking yourself what you need to learn.

Being seen takes ninety seconds. Being heard takes a conversation. Being known takes as long as it takes, and it starts with the decision to learn someone’s language instead of correcting theirs.

More later...

Watch any lively conversation and you’ll see it happen within minutes. Someone is four words from finishing their thought and the person across from them is already talking. Not responding. Talking. The talking sock gets grabbed before the speaker is done, and nobody seems to notice, or care, because everybody in the conversation is waiting for their turn rather than listening for what comes next.

My parents drilled the opposite into me when I was a little shaver. You don’t interrupt, young man. You wait. You let the person finish. It wasn’t a suggestion. It was a family standard enforced with consequences that eventually morphed into a big part of my character. Or a character flaw to some.

Thirty years of technology support turned that parental order into a professional methodology.

Here’s what actually happens when a client starts describing their problem. Within two sentences, experience has usually handed me the answer. Something clicks, a pattern from a dozen previous consultations surfaces, and I know where this is going before they do. There’s a quiet relief in that moment, not arrogance, the relief of someone who has been afraid of not knowing the answer and just found out they do. I hold unreasonably high standards for myself as a professional. Knowing the answer after sentence two means I haven’t let anyone down today.

And then I do something that runs completely against instinct.

I keep listening.

Not performatively. Not with the glazed patience of someone waiting for their turn to speak. Fully, alertly, with the specific intention of finding out what question to ask next. Because the thing I’ve learned across thousands of consultations is that the client’s third and fourth sentences are where the real information lives. The first two sentences describe the symptom. What comes after describes the patient.

Most people listen to respond. I listen to find out what question to ask next.

The mental red-lining, the urgent internal pressure to solve the problem, slows the moment I have the answer. What replaces it isn’t relaxation and disconnection from the person speaking to me. It’s a different kind of attention, a consistent alertness scanning for secondary and tertiary information, anything adjacent to the original problem that experience tells me might matter. I’m not targeting one malady. I’m scanning the whole body.

A faculty member contacts me. Something isn’t working in their Canvas course, but it worked before. I ask a few questions about their technology landscape, what device they’re using, what browser, what operating system. They tell me they’re on a MacBook with Safari and their OS is up to date. I take that at face value and keep troubleshooting. But experience has shown me something about faculty devices at universities: some of them are old. Not the person, mind you, their equipment.

So I ask one more question. How old is the laptop? When did they get it from the university?

They don’t remember.

I ask them to click the Apple icon in the upper left corner of their screen and select “About This Mac.”

They read me a macOS version number that is six generations behind current.

Bazinga.

Canvas unfortunately doesn’t work with a Safari browser on a six-year-old macOS device. Now we’re having a completely different conversation than the one we started with. This is not going to be a quick fix, and I need to gently prepare my client for an unexpected diagnosis. I need to initiate a discussion about upgrading the operating system to the latest version the hardware can support, or replacing a device that has quietly aged past its useful life. This discussion means I may have to recommend involving their department IT support person, who has their own work style and professional agenda and timeline in the solution, and the faculty member’s afternoon just got significantly more complicated than they expected when they initially contacted me.

That conversation only happened because I kept listening past the point where the first answer appeared.

My faculty client wasn’t lying when they told me the laptop’s OS was up to date. But “up to date” meant something different to them than it means to me, and the gap between those two definitions only surfaces if you ask one more question. A conversational card nobody knew was in the deck.

I think about this every time I’m in a consultation. The client came with a shopping list of needed fixes. My job isn’t just to fill a bag with the items they put on the conveyor belt. It’s to fill the bag and throw a couple of fresh juicy apples on top for the drive home. Something they didn’t know to ask for. Something experience told me they needed before they knew they needed it.

Being heard is a gift given from someone who cares about the person beyond simply nodding along while minutes float by. It’s a choice someone on the other side of the screen or the table makes to pay close enough attention to catch what the client didn’t know they were saying.

Most people listen to respond. The client who gets heard gets something better than a fast answer.

They get the right one.

More later...

Where I live, I rarely take the highway.

Two lanes going each direction can develop a two-mile backup in the time it takes to finish a cup of coffee, all because someone’s radiator decided this was the morning. I’ll gladly tack on an extra five minutes on the side streets every time. I know five different ways to reach my parking lot, and I’ve driven all of them depending on my mood, the season, and whether I need to make a stop.

One of the five routes takes me past a gas station convenience store. And before I started seriously paying attention to what I was eating, my guilty pleasure was Hostess Zingers. Vanilla. Three to a pack. Breakfast of champions. Don’t judge.

There was always a kind older man behind the counter. Big voice, warm presence, and the same greeting every single morning: “Good morning, my man.” I’d reply with “Good morning, Sir,” grab my Zingers, and approach the counter with a five-dollar bill. The total was always $3.72. And every time, without variation, he’d look at the register and deadpan: “That’ll be 372 dollars.”

And I’d place my five on the counter and say, “There’s 500. I’ll take $128 in change, please.”

We did this for months. A Vaudeville routine neither of us rehearsed, performed for an audience of nobody, perfected through pure repetition. It was one of the better parts of my morning.

One day, with no one else in the store and no particular reason except that it felt like time, I said: “By the way, my name’s Chris.”

He stuck out his hand.

“I’m Sammy.”

From that morning forward I greeted him as Mr. Sammy. He still calls me “my man,” and I suspect he always will. He encounters hundreds of people a day. I’m the big guy who used to buy Zingers and now buys Diamond smokehouse almonds. He carries the warmth. I carry the name. Nobody’s keeping score, and the arrangement suits us both perfectly.

I think about that handshake more than you’d expect because in my professional life, I always have the name. It’s in the From: field when the first email arrives. It’s already there in my Canvas search for people. I know who I’m talking to when they need help with their course. Their name exists. What doesn’t always exist is the recognition, and that is a much different story.

For the past six years of fully-remote work, most of my clients have only ever seen me as a face wearing slim glasses and a white goatee in a two-inch by three-inch rectangle on a Zoom or Teams call. What they haven’t seen is the rest of me: 6’3”, wearing black, taking up considerably more hallway than the little window suggests. When I’m on campus for an in-person consult and I spot a client I remember from a previous video interaction, I understand completely why they might not place me. I’m not the Canvas guy from the small window anymore. I’m a person walking toward them, and for a half-second that reads as ambiguous.

So I make it easy.

I’ll modify my path slightly so I’m walking directly toward them. If I’m wearing a hat, it comes off. Even though I am soft-spoken by nature, I’ll use my projecting voice and say their name, their full name, and if students are nearby I’ll lead with the title because dignity matters in front of an audience. And then I watch their face do the thing.

The bewildered look. The half-second of trying to place me. Their face has an expression of concern since they’re being approached by a large stranger on a Tuesday afternoon who looks like they’re about to hand them a court summons. Instead I help them remember me, “I’m Chris Powell. I’m your Canvas Admin?” And everything changes. Their face immediately switches from apprehension to a big smile. And they greet me with a big “Hi! It’s so nice to see you out of a Zoom window!”

I often ask how the quarter is progressing for them. It’s open enough to invite honesty and not the usual question that elicits an ambiguous “Fine” for a response.

I also know they’re in transit. They have somewhere to be. So I wrap it up deliberately: “Well, I’m off to a consult in Haggard Hall.” A slight bow, because I’m usually looking down at them and the bow closes the distance without being strange about it. “I’m glad I got to run into you in person. Have a good afternoon.”

And we part ways.

The whole thing takes maybe ninety seconds. But something happened in those ninety seconds that six months of Zoom calls didn’t accomplish. I saw them. Not the ticket. Not the little video window. Not the subject line. I saw the person.

And now they see me. The person, not just the Canvas guru.

Mr. Sammy probably couldn’t pick me out of a lineup, but he’d recognize the energy the moment I walked through the door, the guy who takes $128 in change and means it. That’s not nothing. That’s actually quite a lot.

Being seen doesn’t require being remembered. It requires being met where you’re at. And in the 30 seconds it takes to remove a hat, say a person’s name, and ask one honest question based on genuine interest, you can meet someone in a way that outlasts every transaction that came before it.

That’s the whole methodology, right there in the hallway.

More later...

Sometime in the early days of my career, I was having beverages with tech colleagues. With an ego approaching obnoxious at the height of my early-30s lack of filter in public, I blared the following declaration to the table:

When I stage a coup and take over my university, one of my first acts as Imperial Wazoo is to ban ‘urgent’ from all communications.

The table laughed. I didn’t smile, I meant every word.

That was then. I’ve grown as a professional since, and I’ve grown to understand the client’s perspective in ways my younger, invincible self hadn’t learned yet. I understand that when something breaks at the wrong moment, it feels urgent. The adrenaline spike is real. The frustration is real. The quiz you scheduled for your students starting in eleven minutes has somehow disappeared, and there isn’t time for a thoughtful, focused troubleshooting process to self-resolve the crisis.

Urgent means something specific. It means the situation cannot wait. It means delay causes irreversible harm. It means the building is, in some meaningful sense, on fire. Someone’s hair might be on fire too. I’ll grant that.

A Canvas gradebook is not on fire. Nor is graded curriculum.

Urgent often showed up in the subject line of email support requests early in my career. I noticed something about those ALL CAPS messages: it almost never described the situation accurately. It described the feeling. There’s a difference. “I am anxious and I need help” is honest and I can work with that. “This is urgent” is a demand wearing a descriptor as an armor-plated costume, and it loudly asks me to absorb someone else’s anxiety and let it reorganize my entire morning.

The external response was always calm, prompt, and professional. I didn’t lecture a tenured professor about word choice. I just didn’t let Urgent crack the whip on the work I was doing on their behalf. But make no mistake: my priority queue runs on relationships, context, and a few decades of pattern recognition. It does not run on adjectives.

Here’s what the math looks like from inside the machine. I process roughly 9,000 emails a working year. I’ve been at my university for 28 years. That’s over a quarter-million emails coming into my inbox. Give clients the benefit of the doubt: two percent carry genuine urgency. That’s approximately 5,000 instances of anxiety landing in my inbox over a career, a Costco shopping cart on a busy Saturday, jumping the queue, knocking everything away at the front of the line so they can get their cart checked out before everyone else waiting in line.

If you haven’t learned by now, I’m a people pleaser by nature and I’m a professional burden-bearer. When a client’s anxiety arrives in my inbox, I absorb it and carry it until the problem is resolved. That means I’ve incurred 5,000 adrenaline spikes in my career at the university. Three a week, on average, for 28 years.

In my line of work, I can’t resolve issues any faster when there is Urgent in the email, like a sped-up timelapse of video footage. The other 245,000 emails got the same promptly-delivered response as the urgent ones. The word Urgent didn’t change my output. It just sent my adrenal system into overdrive.

Up until now, I’m confident most clients have no idea that’s happened to a technologist like me. I’m less confident it would change their behavior if they knew.

Supervisors aren’t in the business of tracking the toll elevated anxiety customer support takes on their subordinates. A manager’s mission is for consistent reliable work performance with no complaints reaching the level above them. My colleagues in the trenches understand it completely, but can’t change anything about it. So the pressure stays where it lands, on the person reading the all-caps subject line at 9:00 am and choosing, again, to respond with calm and competence instead of what the moment might otherwise deserve.

There is exactly one legitimate use of the word Urgent in my professional universe, and it peaked commercially in 1981. Foreigner released it as a single from their fourth album. It hit number four on the Billboard Hot 100. It has a saxophone solo. It’s my only use case.

I’ve waited tables. I’ve faced someone treating me like furniture with a notepad. I know what it costs to refill the water glass and bring a replacement cup of soup while smiling and saying, “of course” when the internal monologue is something considerably less gracious. I couldn’t call the rude table out on their behavior without getting fired. Neither can the tech on the other end of your urgent email.

More later...

None of them know my name. Not one of them has ever sat across from me, shaken my hand, or offered me advice over coffee. Four out of five I have not met in person, though I got the chance to speak with one on the phone over a decade ago. One of them spoke to a room full of high school boys in 1990 and has almost certainly never thought about it since. And yet between the five of them, they are more responsible for who I am professionally than any manager, colleague, or formal mentor I’ve ever had.

I’m not sure whether to thank them or warn them.

The first one is C.G. “Coke” Roberts. Evergreen Boys State in 1990. I was seventeen years old sitting in an auditorium at Evergreen State College when he delivered a keynote built around a single thesis: “I will do what I say I will do when I say I will do it.” Eleven words. He said it like it was obvious, like everyone in the room should already know this and he was just reminding us.

I memorized it. I’ve never forgotten it.

At age 17 it felt inspiring in the way things feel inspiring at Boys State, which is to say genuinely but temporarily. Then I went back to my senior year, took a restaurant job, and discovered that the motto had teeth. Showing up on time. Finishing my side work. Not quitting when a Friday night went sideways with dropped plates of food and impatient customers. The philosophy didn’t wait for a meaningful career moment to prove itself. It went to work in a burger joint first.

Years later I signed a mortgage. I was twenty-four, barely keeping an apartment clean, suddenly owing a very large sum of money to a bank that would take my house if I stopped paying. Exciting and terrifying in equal measure. And somewhere in the back of my head, Coke Roberts was still talking. I will do what I say I will do when I say I will do it. The mortgage made it survival. Survival made it identity. Identity made it the foundation everything else got built on.

Coke Roberts has no idea.

The second one is Will Guidara. I came to Unreasonable Hospitality the way most people come to books that change them: I wasn’t looking for it to change me. I was nodding along, recognizing scenes and principles I thought were specific to fine dining, and about a third of the way through the book I realized I wasn’t reading about restaurants at all. I was reading about every Canvas consult I’d ever run with a new faculty member three days before their first term began.

Those consults are the ones I care about most. New faculty arrive at a university with their heads already spinning: policies, handbooks, HR forms, curriculum decisions, and then the department chair assigns them three Canvas courses and tells them they’re teaching in seventy-two hours. They’re not frazzled, they’re drowning. I don’t put a white tablecloth on the table for those conversations, but I meet them exactly where they are. I find out what they already know about Canvas and what gives them anxiety. I build the session around their specific situation, not a standard onboarding. I encourage them to email me a week after classes start, because I’ve learned from experience that’s when the real questions surface. I send them a recording of our consult so they can replay the parts that mattered at two in the morning when they need them.

I was doing all of that before I read a word Guidara wrote. What he gave me was the language to understand what I was doing and why it worked. “Service is black and white. Hospitality is color.” I paused my reading and put the book down when I read that sentence. I stared at the ceiling for a while. Yahtzee.

Will Guidara has no idea.

The third one is Simon Sinek. I found him through his TED talk on leadership, which reframed something I’d been quietly confused about for years. I’m not a leader on any org chart. I have no direct reports, no budget authority, no title that signals leadership to anyone above me. But I lead the people I serve every single day, and I lead some of the people I work alongside, too. Sinek gave me the language to stop apologizing for that and start owning it.

Then he closed the talk with a framework that stopped me completely: start with a personal statement, build toward your professional purpose, strip out the jargon, and end with “wanna hire me?” I dove into Start With Why, then Find Your Why, then The Infinite Game. And I went to work on my own Why until I found it.

“I am fueled by sharing information with people. My area of specialty is sharing information about technology. Through focused attention on their unique issue, and with a customized resolution that is both informative and entertaining, I help people de-stress their relationship with technology and get them to happy hour sooner. Wanna hire me?”

Whether or not someone drinks in a bar, everyone understands happy hour. Nobody hears that phrase and pictures a long painful tech support session. The expectation is set before I’ve touched a keyboard. That’s the Why doing its job.

Simon Sinek has no idea.

The fourth one is Patrick Rhone. I found him on minimalmac.com sometime in 2010, a Tumblr blog about living deliberately with technology before that was a category anyone had named. Before Rhone, I was chasing the new shiny. The latest device, the freshest app, the upgraded version of everything I already owned. It cost a lot of money and burned hours on learning curves that reset every product cycle. Rhone showed me it was okay to stop.

He wrote about his Hobonichi Techo journal. He developed a dash-plus system for analog note-taking years before Ryder Carroll turned Bullet Journal into a publishing phenomenon. He posted about his Red Wing Iron Ranger boots with the same quiet devotion he brought to his iPhone, which he used as his primary writing and publishing tool. Buy the right thing once. Learn it completely. Use it until it becomes part of you.

I took that technology philosophy and made it my own. A modded iPod Classic with a 1TB internal drive and a custom Rockbox OS, a diminutive XTEINK x4 eReader, a burly Casio G-Shock on my wrist. None of those choices happened by accident. Rhone planted something in me about intimate knowledge and deep use of a few things you own that produces more satisfaction than any upgrade cycle ever could. I’ve been living that ever since.

Patrick Rhone has no idea.

The fifth one is Seth Godin. A friend recommended I read Linchpin after noticing something about my approach to tech support that I’d been quietly second-guessing for years. The honest version of that internal narrative went something like this: nobody else here is caring for clients the way I do. Some techs prefer to sit behind a monitor screen rather than in front of an actual person. I’m doing something different, and it feels wrong when you’re the only one doing it.

Linchpin quieted that voice. Not by telling me the contrast wasn’t real, it was real and visible every day, but by telling me the contrast was valuable. Being the one who does it differently isn’t a liability. It’s a strength, almost a competitive advantage. Then Tribes extended the argument: find the community of people who believe what you believe, because they exist, and internalize within yourself that you’re not a freak for believing it.

I’ve spent the years since building exactly that. This essay series, a Substack blog, a LinkedIn presence, the conversations that keep happening with people who recognize something in the writing because they’ve felt it themselves. Godin told me the tribe existed before I’d written a word for them. Turns out he was right.

Seth Godin has no idea.

Here’s what I’ve come to understand about these mentors, these men who never knew my name. They didn’t build me, they revealed me. Each one arrived at exactly the moment I was ready to receive what they were offering, and the reception was always the same: not discovery but recognition. Not learning something new but finding the language for something already running.

Coke Roberts gave me my IntegrityOS. Guidara connected the fine dining experience with relational tech support. Sinek gave me a framework to articulate my Why. Rhone gave me permission to stop chasing and start committing. Godin told me I wasn’t a freak.

I’m still the monster they made. I’m still carrying all five of them into every consult, every essay, every conversation with a new faculty member three days before their first semester starts.

They have no idea. And I’m grateful every day that they did the work anyway.

More later...

Early in my career I discovered something that felt radical at the time: saying “I don’t know” out loud to a client. It didn’t get me fired, and it didn’t even end the conversation. What it did was buy me something more valuable than a quick answer I wasn’t sure about. It bought me trust.

Genuine transparency was the foundation. What I’ve built on top of it over thirty years is something a little different.

Here’s the scenario. A faculty member contacts me with a Canvas issue. I prepare ahead of time, think through the likely cause, queue up the solution, and schedule a live consult. I’m ready. They arrive into the Zoom meeting, I have already shared my browser window while masquerading as their account, I navigate to the problem area in their course, and execute the fix I’ve been carrying in my head since I read their email.

It doesn’t work.

What I’ve overlooked, not for the first time and probably not for the last, is that I’m navigating around their course with their teacher-level rights, but I’m still carrying administrator-level permissions they don’t have. The fix works for me. It won’t work for them. The demo has failed in the specific way that only becomes obvious when you’re already in the middle of it with someone watching.

The easier response in that moment is deflection. Blame the web browser. Blame the client’s network. Blame a recent system update nobody asked for. Blame it on the rain, anything but pointing the blame on themself. Most clients won’t push back, and the tech walks away with their composure and dignity intact while the client remains confused about what actually went wrong. I understand that choice of response. The profession produces it. But deflection is a slow leak in the trust balloon that takes years to fill, and I’ve spent thirty years breathing into mine carefully without getting light-headed.

In that moment when I see things aren’t working, something happens in my head that most clients would never fully understand. I flash to a memory of Bill Gates introducing Windows 98 at COMDEX, standing in front of a massive audience, and watching his demo machine produce a Blue Screen of Death on a projection screen visible to everyone in the room. The CEO of Microsoft. Global stage. Complete system failure. His response was a slight smile and a dry acknowledgment that this was why they hadn’t shipped the product yet.

Most of my clients aren’t familiar with that reference. But I am.

So instead of the internal spiral, I look up from the screen, and I say: “Well. That was a C-minus for a demo.”

They chuckle. Most of them have genuine grace for me in that moment. And here’s why: they’ve stood at the front of a lecture hall with a hundred students watching and felt technology fail underneath them in real time, with nowhere to go and no way to pretend it isn’t happening. They know exactly what this feels like. When I acknowledge the demo failure with a teacher’s grading scale, I’m not just defusing the moment with humor. I’m speaking their language. I’m meeting them where they live.

As I am recalibrating my path toward issue resolution using their teacher rights I will say to them as I’m clicking around the screen at 80 mph, “I appreciate your patience while I do all these nerdy things to get to the solution. Once I get to where we need to be, I’ll walk through the steps again in a more deliberate way so you aren’t getting dizzy from the quick scrolling and all the clicky-clicky I’m doing now.” That’s the other phrase that comes out in those moments. It’s an invitation rather than an apology. Come with me while I figure this out. You’re not waiting for me to perform competence. You’re watching competence actually work, which sometimes includes hitting a wall and finding a way around it.

The best baseball players don’t get to first base six out of ten times. A .400 batting average is one of the rarest achievements in the history of the sport. Michael Jordan missed game-winning shots. He talked about it openly, not as confession but as context. The misses were part of the methodology. You can’t take the shots that matter without accepting that some of them won’t go in.

I think about that when the demo doesn’t work. Not as consolation, but as permission given to myself to mess up.

What’s changed over thirty years is the internal experience of the moment. There was a version of me, younger and less certain, who would smile at the client and say something graceful and laugh nervously while running a Chris Farley internal monologue disparaging himself in a Saturday Night Live skit from the ‘90s where he asked lame interview questions. Stupid. Stupid. Stupid. Admonishing myself in real time for the error while projecting something that looked like professional composure. The gap between the external grace and the internal spiral was exhausting to maintain.

That gap has closed. Not because I’ve stopped caring about doing good work, but because I’ve done enough good work to trust the aggregate. The C-minus demo is one data point. The career is the dataset. I know what the dataset shows.

The “darn it” feeling that arrives now when the demo goes sideways isn’t indifference. It’s proportion. Something didn’t work. I’ll find what did. I know what I am capable of. My client is still in the video meeting, still patient, still rooting for the solution to arrive. Rarely will any of them kick me when I’m down for acknowledging an error. They’re too busy recognizing something they’ve felt themselves.

The gentle failure isn’t a lesser version of competence. It’s what competence actually looks like when it’s honest about being human.

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In December 2019, my wife asked for one thing for Christmas.

She wanted me to read Jan Karon’s “At Home in Mitford” to her. One chapter a night, starting December 1, in the evening after everything was done for the day, as we approached bedtime. Karon’s book is a heartwarming story about an Episcopal priest in a small mountain town in North Carolina, surrounded by lovable quirky characters. My wife’s co-worker had recommended it.

So I said yes.

That was seven years ago. We finished the entire Mitford series, all 15 books. We then went through Jacqueline Winspear’s 18-volume Maisie Dobbs series after that. We’re presently on book 19 of Louise Penny’s 20-volume series about Quebec chief of homicide detective Armand Gamache. One chapter a night, sometimes two if they’re short. It morphed from a gift to a nightly practice. It’s what we do after brushing our teeth and swishing Listerine.

My wife likes my baritone voice. It puts her to sleep sometimes. My voice is not a bug, it’s a feature.

Here’s where the technology problem enters.

As we approach bedtime, bright overhead lights keep the brain awake which defeats the purpose of everything we’re doing, so the bedroom lights dim. I don’t like battery-powered clip-on book lights; they aren’t stable enough for shifting around in a chair, and the engineering is always slightly wrong in a way that irritates me more than the darkness does. So from the beginning, a backlit eReader was the obvious answer. I could see the words in a dimmed room, my wife could drift off to Armand Gamache solving murders in Three Pines, and the ritual would be protected.

Simple enough. Except finding the right device took six years and four attempts.

I started with a Kobo Libra. My reason for not choosing a Kindle was straightforward: I didn’t want to live inside Amazon’s walled garden of digital rights management, where the books I purchase aren’t quite mine and the device reports back to a mothership I didn’t invite into my bedroom. The Kobo was a reasonable first choice. It worked. But I grew tired of it in the way I grow tired of most devices once I’ve fully explored what they offer and mapped where they fall short. I sold it and kept looking.

The Onyx Boox Note Air 2 came next. It’s essentially a ten-inch black and white Android tablet, and it looked impressive on paper. Backlit screen, large display, plenty of real estate for a page of text. What I discovered in practice was that Onyx built their operating system primarily for note-taking with a stylus. Reading digital books felt like an afterthought, something the device tolerated rather than embraced. The OS was clunky in the specific way Android gets clunky when a manufacturer layers their own skin over it and calls it done. I flipped it on Ebay.

I downsized to the Onyx Boox Palma, which is roughly the size and shape of a mobile phone with a six-inch e-ink screen. Easier to hold, easier to navigate, more honest about what it was trying to be. The Android OS was still clunky, still carrying the Onyx note-taking DNA underneath everything, still not quite right. Better, but not it.

And then I heard whispers on the internet.

An overseas company called XTEINK was marketing a stripped-down eReader called the x4. Four-inch screen. No digital rights management. No unnecessary apps cluttering up the home screen. No app store. Load your books onto it via microSDHC card. Price: $80. The online community around it was small and enthusiastic in the way communities form around devices that do something specific very well and nothing else at all.

I bought one. The stock firmware was, as advertised by the community, not good. I followed the steps to flash a modded firmware developed and shared by people who cared about the device enough to fix what the manufacturer hadn’t. The new UI was clean and intuitive. The reading experience was exactly what I’d been looking for.

There was one problem. No backlight.

So now I read in the dimmed bedroom with a small LED flashlight to illuminate the page. Additional friction, yes. An irony not lost on me after six years of searching for the frictionless solution. But here’s the thing about the friction you choose versus the friction imposed on you: they feel completely different. The LED flashlight is my decision. The clunky Android OS was not something I chose. I tolerated it until I didn’t have to anymore.

When I hold the XTEINK x4 in the dimmed bedroom and click on the night’s chapter, I have an internal smile I can’t fully explain to anyone who hasn’t spent years caring about this particular problem. There is no telemetry uploading my reading habits to a datacenter somewhere. There is no mothership receiving a signal that I am currently on chapter 14 of “A World of Curiosities” at 10:47 on a Tuesday evening. There is no bookstore waiting to suggest my next purchase based on my reading history. There are no persistent software updates. And there is no AI guide recommending other books based on my reading history.

It reads books. That’s all, folks. It reads books.

Naturally, I’m aware of the built-in eReader book apps on Apple and Android phones. But I’ve learned that a separate, slim, stripped-down device allows a focus that can’t be had on a 2026 phone or tablet, no matter how much you modify settings to prevent distractions. This is what I’ve come to call Monastic Technology: not the rejection of tools, but the deliberate choice of tools that serve a single purpose and ask nothing in return. The phone that does everything is the ugly frame. The $80 device that just shows a book is the beautiful work happening inside it.

I spent six years and four devices looking for a tool that would disappear into a ritual my wife asked me to start on a December night in 2019. What I found was an $80 device with no backlight that I read by flashlight in a dimmed bedroom while my wife drifts off to the sound of my voice somewhere in the Quebec countryside with Armand Gamache.

My wife asked for one thing for her Christmas gift. I’m still giving it to her.

More later...

In April 2024, the United States Department of Justice issued a mandate. Online content for public-facing websites, including course content inside learning management systems like Canvas, had to be made accessible for all learners. Every faculty member at my institution needed to know this was coming, what it meant for their courses, and what they were expected to do about it.

Simple enough problem. Except the communication channels available to me were all broken.

Email gets deleted before it gets read, especially email that arrives with the faint bureaucratic odor of compliance. There’s no single webpage every employee visits regularly enough to post a message that actually lands. Announcements inside Canvas get scrolled past. I needed every faculty member who teaches a Canvas course to see this information, understand it, and acknowledge it. I can’t speak to thousands of personnel to make them aware of the situation; there just aren’t enough hours in the day.

So I thought about where they were already going.

Every term, teachers import their course content from a prior term into their new course shell. It’s a ritual as reliable as the academic calendar itself. To do it, they have to navigate to a specific location inside their course. That location, that specific moment of navigation, was my intercept point.

I sat down with an AI agent and started a conversation in plain English. I’m a Canvas administrator. Here’s my situation. Here’s what I’m envisioning. Is this possible? What followed was an iterative dialogue, part problem-solving session, part debugging exercise, part aesthetic negotiation. I guided the agent back out of the weeds more than once when it provided JavaScript and Cascading Style Sheets that wasn’t applicable to what I needed. I fed it error messages from my test environment and asked it to help me understand what went wrong. I made requests that had nothing to do with syntax: I only want this popup to appear one time per browser session for teachers. I want it prettified, modern sans-serif font, clean background. I know my clients.

What came out the other side was a customized JS and CSS modification to my Canvas UI theme. When a teacher navigated to that specific course location, a popup appeared explaining the accessibility mandate, a clickable link to official resources, and a close button they had to click to dismiss it. Not a checkbox. Not a scroll-past. A required interaction. Nobody could claim they hadn’t been made aware.

I tested it the way I test everything: by putting myself in my clients’ shoes. As a Canvas administrator I can masquerade as any account in my institution for support purposes. I picked a handful of faculty I know well, the ones who would tell me immediately if something felt off about their Canvas experience, masqueraded as their accounts, navigated to the course import location, and watched the popup appear exactly as designed. Clean workflow. Easy dismissal. Every time. Management tested it independently and found no issues.

The popup worked because it didn’t ask faculty to come find the information. It put the information exactly where they were already going, at the moment they were already paying attention, with no way to not see it. I was able to solve a human attention problem with a little behavioral architecture and a conversation with an AI agent.

Around the same time, a different friction problem arrived from a different corner of the university.

The Provost’s office handles cases of academic integrity, the situations that arise when students find academic shortcuts through non-traditional means in submitting assignments or completing assessments. When a case is referred, the student is required to complete a Canvas training course on academic integrity. The staff in the Provost’s office were responsible for enrolling those students. For a while, that meant emailing me.

I had a concern with that arrangement from a privacy standpoint. Being handed student names in an email meant I knew things about people I might recognize through other channels. I didn’t want that information. Nobody had designed the workflow to protect either of us from it.

So I elevated the Provost’s office staff’s permissions in Canvas, moved the academic integrity course into an area they could access directly, and then sat down with an AI agent to solve the friction problem they were about to inherit.

The existing process involved a fairly complex series of steps and an Excel spreadsheet manipulation. What I built through iteration and plain English conversation was a clean web application launched via a Python script. The staff’s new workflow looked like this: double-click a desktop shortcut icon to launch a command prompt window, open a bookmark in their browser that I had customized for them, enter a unique student ID into a form field, click a button labeled “Enroll this Student,” confirm the green box showing “student added into course,” close the browser tab, close the command prompt window, move on with their day.

That double-click is the whole philosophy. A high-ranking university office, handling sensitive student conduct cases, accomplishing a formerly cumbersome workflow through a single gesture I built for them in a conversation with an AI agent. They didn’t need to know what was running under the hood. They needed it to work cleanly, every time. And it did. They told me so.

A few months after deploying the accessibility popup, I found myself at an educational technology conference. I wasn’t on the agenda. But they had an hour blocked for lightning rounds, five-minute presentations from attendees who had something worth sharing. I had been reading the room all conference. Accessible content and AI were the two topics consuming every hallway conversation. I knew what I had. I put my name on the list. It turns out I was the first lightning rounder.

In five minutes I introduced myself, described the mandate, explained the situation every Canvas administrator in that room was navigating, and walked through what I had built. I was direct about one thing from the start: this was not my original coding creation. I had help. An AI agent wrote the syntax. I supplied the problem, the constraints, the client knowledge, and the judgment about when we’d gone sideways and needed to redirect.

Here is my email address, I told them. If you want the code, it contains no sensitive or classified information, and I’m happy to send it. If you want to walk through the implementation together, we can meet via Zoom.

A few institutions took me up on it. It felt good to share something useful without an invoice attached, without an agenda beyond the sharing itself.

Here’s what I want to be clear about, because I think it matters in a moment when everyone is trying to figure out what AI is actually for. I didn’t learn JavaScript. I didn’t learn Python. I didn’t need to. What I brought to those conversations was thirty years of knowing my clients, knowing what friction looks like from the inside, knowing what “one time per browser session” means in human terms before it means anything in code. The AI knew the syntax. I knew the people.

That combination, domain expertise plus plain English plus the judgment to know when you’ve gone off course, is something that accumulates slowly, over decades, through ten thousand small interactions with humans who needed something and trusted you to help them find it.

The popup told faculty what they needed to know. The double-click gave the Provost’s office their time back. The conference room got code they could use the next week.

Nobody paid me for any of it. That was never the point.

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There’s a scene in the movie Idiocracy that I’m reflecting on, and quoting, more and more. The president of the United States and his cabinet are meeting with the smartest person alive, a time traveler from 2005, to discuss why the nation’s crops are dying. The answer is simple: they’ve been irrigating with Brawndo, a sports drink like Gatorade, instead of water. When the smartest person in the room asks why they don’t just use water, the cabinet can only stare back and say, “But Brawndo has electrolytes. It’s got what plants crave.”

The president’s cabinet aren’t evil or lazy. The ad’s tagline replaced the thinking so completely that the thinking stopped happening. Nobody noticed.

I think about that scene every time I call a support line and hear, “Your call is very important to us.”

No, it isn’t. If my call was important to you, a human being would pick up within a minute of me dialing. Instead I wait, and when the human finally arrives, I’m greeted through a low-tech headset with ambient call center noise bleeding through, by a voice drenched in melancholy and ambivalence: “Thank you for calling [company name] where it is my job to ensure you have a pleasant experience today.”

The person on the other end of the line isn’t bad at their job. They were handed a script during their onboarding and was told it was how to provide outstanding customer service. My explanation of needing help is probably transcribed on their computer monitor already, which means they don’t have to listen closely enough to hear the nuances of my voice, to pick up on how I’m actually feeling about the problem, to notice that I’m frustrated or confused or just tired. The script handles that. The script has electrolytes. It’s got what clients crave.

Except it doesn’t. And both people in this phone call know it.

I’ve been lucky. In nearly thirty years of having roles in desktop support, computer lab coordination, IT management, and Canvas LMS administration, nobody ever handed me a laminated card. No approved language, no required phrasing, no “I’m sorry to hear you are having troubles with your computer. I am here to provide outstanding customer service for your needs.” I was given the agency to bring my personality, my wit, my humor, and most importantly my empathy into every interaction, and I am genuinely grateful for that. The absence of a script is part of why I still care about the work.

But I wasn’t always good at filling that space.

In my younger years, I made the mistake most new technical professionals make: I spoke in jargon. I was explaining a system failure to a senior faculty member and I watched their eyes glaze somewhere around the second acronym. They interrupted me, in the way longtime employees often do, and asked me to explain it again, but this time in a way that someone who didn’t live in technology would understand.

I paused, collected myself, and then I did something I hadn’t been taught to do: I thought through how I would explain this to my mother. Not a simplified version, not a dumbed-down version, a translated version. The right words for this specific human sitting in front of me. I found a metaphor. I used a cultural reference. I was deliberate in my communication.

The head that had been shaking slowly started nodding. Follow-up questions came, real ones, and I answered those the same way. By the end of the conversation, the faculty member understood not just what had happened but why it mattered. That’s not something a script could have produced, because a script can’t think and adapt. It can only deliver the next line.

I’ve watched support professionals in meetings, in hallways, and at conferences. The thing that always strikes me is how funny they are. How animated. How eager to speak and be heard. And then I’ve watched some of those same people sit down at a support desk or pick up a phone and the mask goes on. The personality doesn’t disappear exactly, but it retreats behind something cautious and rehearsed. They start talking like they’re narrating a technical manual in a deadpan voice that would make Steven Wright sound animated.

I don’t blame them. I blame the system that taught them the mask was professionalism.

I want to be careful here, because the student workers staffing university help desks are not the villains of this story. Their hearts are in exactly the right place. They respond quickly, they want to help, and they’re doing their best with what they were given. What they were given is a troubleshooting document, a list of if/then responses, a set of approved answers to the most common questions. Clear your browser cache. Restart your computer. Look at this knowledge base article. Submit a ticket if the issue persists.

What they weren’t given is the years of pattern recognition that lets an experienced technologist hear something in a client’s voice and know that restart your computer isn’t the answer. They weren’t taught ELI5, explain it like I’m five without being condescending. They weren’t shown how to translate complexity into something a person can grasp. That’s not a criticism of the students. That’s a description of what we’ve failed to teach them.

Here’s where I have to be honest about something, though, because this essay would be incomplete without it.

There are moments when my unique conversational voice isn’t the right tool. When a system-wide disruption affects hundreds of people and a communication has to go out under the university’s name, my instinct toward warmth and informality can create problems I didn’t intend. Management reviews those communications for a reason. They know how to speak bureaucratic in the way that survives legal interpretation and administrative scrutiny and the inbox of someone three levels above my pay grade who is looking for liability language, not a friendly tone.

Sometimes the approved language is the right language. And I’ve had to make peace with that. The best I can do is protect the spaces where the relational voice still works, use it deliberately and without apology in every individual interaction, and trust that the nodding head is worth more than the approved phrasing.

Brawndo has electrolytes. But water is still what the plants actually need. The message is what clients crave.

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In 1998, I was in my second year as a professional technologist, I was 25 years old, high-energy, and carrying considerably more hubris than caution.

A faculty member needed help with accessing their email. Back then, this was Microsoft Mail, a now-archaic desktop application that brought down emails from the university’s email server to the employee’s local computer. In those days the only cloud in the late ‘90s was a fluffy one in the sky that looked like a ducky or a horsie.

I arrived at their office, sat down at their computer, and started clicking around their desktop with the confidence of someone who hadn’t yet learned what overconfidence results in. Less than a minute later, I realized I accidentally deleted their email archive folder...not a server copy, not something recoverable. The original. Seven years of emails, gone.

The faculty member was angry. They eventually forgave me. My supervisor was angry. They got over it.

I never got over it.

That was seven years of communications that vanished before I could right-click to undo. That folder contained professional correspondence and maybe personal letters from family and friends back when we referred to it as electronic mail. I didn’t ask the faculty what the contents of that folder contained, I was swallowing too much water drowning in the shame pool.

That moment is still with me every time I sit down at someone else’s computer. It’s the reason I state it audibly, before I touch anything: “There will not be any loss of data.” It’s the reason I tell clients, specifically and deliberately, as they watch me move folders around in their file explorer, “Your photos are snapshots in time of your family’s life. I will never put these in jeopardy.” It’s the reason I triple-check, out loud, that every file has successfully arrived in its new location before I touch the delete button. Make no mistake, I’m a quirky technologist, but the clients who sit next to me watching me do my work and hearing my running commentary of every path I take on their computer know beyond a shadow of a doubt I take their files seriously.

What started as a wound became a protocol. What became a protocol became an oath. What became an oath eventually became the thing I’m known for.

She found me through a family connection. A retired widow, warm and friendly, who knew I was a kind tech and wanted help untangling her late husband’s online accounts not long after he passed away. That was six years ago. Since then she’s contacted me every couple of years when it’s time to untangle some more. A new layer of the digital life he left behind, another account that needed attention, another subscription quietly renewing in the background without her awareness until there was a noticeable charge on the credit card bill.

This visit was the most complex yet.

Modern tech companies are not designed with a retired widow in mind. They’re designed to move personal customers into a proprietary silo and keep them there, making it as difficult as possible to leave, consolidate, or simply understand what they’re paying for and why. Her late husband’s files and photos lived in Microsoft’s silo. Her own photos lived in Apple’s silo. Neither company designed their product to make consolidation easy. Neither company likes talking to the other. And somewhere in the middle of both of them was a woman who just wanted to know where her files were.

I spent five or 10 minutes reacquainting myself with her tech landscape after a couple of years away. Accounts, subscriptions, usernames, passwords, access. Mapping in my mind what existed, what was active, what was dormant, what was hers versus his. As I worked through it she said, at least three times: “I would have no idea where any of this is located.” And: “I would never have been able to do this by myself.”

I smiled and said gently, “I’m glad I can sidetrack some unnecessary speed bumps in getting access to your files.”

What I found as I mapped the landscape: two Microsoft 365 subscriptions. One had expired five months ago, which was why Word and Excel on her desktop computer had stopped working. She had the modern version of Word and Excel, which is a subscription-based model for use. If Microsoft doesn’t get their money from the subscription fee, you don’t get to compose a document. The bouncer in front of the club ain’t letting you in.

Pop quiz: when your credit card expiration date is soon expiring, and you automatically receive a new credit card in the mail, do you immediately go to your online accounts to update your credit card info with the new expiration date and CVV code? Me neither. I have to be reminded in an email from the company that my card has expired on their account, then I take action to update.

My client didn’t see the tiny yellow triangle with an exclamation mark in it in the account box at the top of her Word and Excel windows. I saw it, and learned that account was attached to her late husband’s email. The card used for the late husband’s subscription expired without her awareness, two or three weeks before she contacted me. Two or three weeks without being able to update a spreadsheet.

The other Microsoft 365 account had auto-renewed four months ago for an annual $130 fee, quietly, automatically, because that’s what subscriptions do when nobody is watching them.

She didn’t need everything in Microsoft 365. She just needed Word and Excel.

I remembered that a techie website called StackSocial periodically offers lifetime software licenses for tools like this. I checked. Sure enough: a lifetime license for Office 2019, $18. Everything she actually needed, one payment, no annual renewal, no silo pulling her back every twelve months. No immediate checking with the mothership to confirm an active licensed account.

She had her credit card out before I finished the sentence. The license code arrived in her personal email within a minute. I pasted the long code into the account setting and blammo, Word and Excel both immediately opened. We then had confidence to cancel the $130 per year subscription.

A flash of inspiration that saves $112 per year for a retired widow is pretty satisfying.

Then I addressed the OneDrive situation.

Her late husband’s files, documents accumulated over a lifetime, 80GB of photos that represented decades of family history, holidays and ordinary Tuesdays and moments that exist nowhere else, were living in Microsoft’s cloud silo, connected to an account she rarely used, behind a password stored in a browser. That’s not a stable home for irreplaceable things.

I moved everything to an external hard drive. All 80GB of photos. All 10GB of documents. Every file transferred, verified, confirmed present and accounted for before anything else happened. The 25-year-old who lost seven years of emails in 45 seconds was standing right behind me the entire time, looking over my shoulder, making absolutely certain nothing bad was going to happen. I could even smell the Axe deodorant scent I wore back then.

When every file had safely arrived, I signed her out of OneDrive and uninstalled the program from her Windows 11 computer. No more Microsoft silo. No more competing save locations. No more notifications sliding in from the right edge of the screen asking her to sign back in to a service she no longer needed. Her files are on a physical drive she can hold in her hands and put in a drawer and know exactly where it is. We agreed to make plans when her schedule permits, and she is up for tackling more nerdy work, to upload those photos into her Apple silo for reminiscing on her mobile device.

Even though it had nothing to do with files or account subscriptions, I installed uBlock Origin Lite on her Chrome browser. The ads I noticed on the columns flanking her personal email webpage disappeared. Clutter vanished. Pages loaded the way they used to load, without the commercial noise that technology companies have decided their customers deserve. She didn’t ask for this. I did it as I was wrapping up the home consultation because I could and because she deserved it.

Before I left, she said it again: “I would never have been able to do this by myself.”

She’s right. Not because she isn’t intelligent or capable, but because the technology industry spent decades building systems that require a professional guide to navigate, charged her annually for the privilege of being confused by them, and never once asked whether what they built actually served her.

Driving home, I thought about the invincible, bulletproof 25-year-old who deleted seven years of emails in 45 seconds. I thought about what it cost the faculty member who trusted him, and what thirty years of carrying that moment quietly produced in a person who decided to never let it happen again.

Her photos are on a drive she can hold in her hands. Every one of them.

That’s the mission.

More later...

The rule of three is a writing technique in storytelling, speeches, and advertising. Evidently groups of three are effective for people to memorize, and it has a certain rhythmic flow to it. I developed my own rule of three in my tech work.

One is an anomaly. Two is a curiosity. Three is a trend.

The first time something unusual arrives in my inbox, I raise an eyebrow and internally say, “hmmmm...” The second time a similar report comes in, my internal radar activates. The third time, I come out guns blazing. Tech support with pew-pew-pew sound effects.

My nervous system is wired to know the difference between a coincidence and an alarm. Three decades of alarms going off programmed my wiring this way.

Last year, a teacher emailed me about their gradebook. A block of seven to ten students had no scores showing for an automatically-graded quiz, even though the quiz had been completed. That’s unusual. I looked at it, confirmed what they were seeing, and started poking around the course doing some troubleshooting.

Then a second teacher emailed me about the same thing. Different course, different students, similar block of missing scores. Ba-doop. The radar activated in my mind.

Then a third teacher.

I didn’t wait for the fourth. I contacted Instructure Tier II support, the administrative escalation channel, sort of like a red phone hotline for Canvas Admins to speak with the mothership. I reported what I was seeing across multiple courses. The Tier II team confirmed other institutions had reported similar issues. Their engineers were working on it.

I briefed my supervisor chain. Got permission to post a global Canvas announcement to all teachers: here is what is happening, here is what the symptoms look like, and Instructure engineers are working on it. Two hours after the first email arrived in my inbox, Instructure’s online status page flipped from investigating to resolved.

Two hours. From first signal to institution-wide communication to vendor resolution. Because I was counting.

Here is what those two hours actually feel like from the inside, because it doesn’t show on my exterior.

There is a small, brief satisfaction in being on my game in spotting the pattern before the status page alerts show up, before management hears about it through the grapevine, before the inbox fills with confused and frustrated teachers. That satisfaction lasts about thirty seconds. Then the dread arrives.

When a Canvas glitch touches hundreds of gradebooks at my university simultaneously, my clients don’t think “Instructure’s engineers pushed a bad update overnight and it will be taken care of in a while.” They think “something is wrong with my course” and they contact the person whose name they know. That’s me. My name is in bold neon letters on the door. The expectation embedded in every support relationship is that the platform works flawlessly. When it doesn’t, the frustration lands on the person responsible for supporting it.

I didn’t write the code. I didn’t push the update. But I answer for it anyway.

So the satisfaction of spotting the trend gets immediately replaced by the calculus of what’s coming: seven teachers emailing in the first hour, each one describing the same symptoms in different words, some terse, some elaborate, all of them radiating low-level alarm. Management emailing simultaneously on a separate channel: “I’ve heard from some that there is something wrong with Canvas. What’s the status?” They need a full briefing, enough information to eliminate the need for follow-up questions, enough context to answer those contacting them. That’s a second communication job running in parallel while the first one is still active.

Picture a large shiny silver griddle in a busy restaurant kitchen. Pancakes. Bacon. Sausage links. Scrambled eggs. Every item on the griddle has a different cook time, a different heat requirement, a different consequence for inattention. The bacon burns faster than the eggs. The sausage links need to be rolled, not flipped. And the pancakes need exactly the right moment or they come off raw in the middle.

Now imagine you’re the only person at the stove. And it’s Saturday morning around 10 am, and there’s a lot of tables with families wanting their breakfast.

That’s what the three-is-a-trend moment feels like in real time. It’s not heroic like Captain America holding onto a building and a helicopter to prevent it from escaping in The Avengers. It’s not even like Neo stopping a machine gun clip of bullets in The Matrix. Just a lot of items on a hot griddle that need attention all at once, and the understanding that if one thing burns, everyone notices.

I describe my observations of uh-oh issues as Trendspotting, a nod to the famous movie from 1996, Trainspotting. I’m not doing what the characters in that film do. Instead I have an instinct of noticing, cataloging, and connecting dots before anyone else. I find gradebook anomalies at a university in Bellingham, Washington, and I take action. Considerably less cinematic, but the pattern recognition is the same.

One is an anomaly. Two is a curiosity. Three is a trend, and I’m already in motion.

The best part is the pancakes didn’t burn. That’s the mission.

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Back when I was a little shaver in fourth grade, I got pushed around and beat up by a few boys in my class, and I didn’t fight back. It’s a long story as to the why, but to this day I still chalk that up to being a failure. I’ve replayed so many times the image has gone soft, but I still remember the names — Sean, Matt, and Damian. The colors of their t-shirts are faded, their young faces blurred, and the emotional impact has worn thin from decades of life. I couldn’t tell you anymore whether the details are accurate or whether I’ve edited them so many times in my mind’s editing bay that what remains is more mythology than memory.

The VHS tape is wearing thin on that one. But I still have it.

The post-COVID era failures are a different story. Those are 4K. Crisp, high-contrast, every word preserved in full resolution. The moment someone above my paygrade challenges my expertise in front of colleagues in an in-person staff meeting. The email from a client on the rampage about an issue with their Canvas course while CC’ing all my supervisors that hit me like an unexpected snowball. The trolling comment an IT peer made in a Microsoft Teams channel. It catches you off-guard, it creates a blitzkrieg of confusion in my mind as to why they launched that salvo. And it leaves streaks of low-level shame streaming down my face.

Nobody notices, of course. That’s the other thing.

I’ll tell you what the replay of those moments feel like. There’s dread in it, the reluctant awareness that I’m about to put myself through something again that I’ve already survived once. There’s cringe, the specific, wincing discomfort of reliving a moment where I didn’t say the appropriate thing, didn’t establish the boundary, didn’t counter the dismissive remark with a perfectly calibrated response that eventually arrived two hours later when I was in the car or sitting slouched at the dinner table chomping on my salad. There’s frustration, directed entirely inward, expressed externally as furrowed brows that make me look angry at something or someone in the room. I’m not angry at anything except myself. I’m in a courtroom in my own mind, arguing a case that already closed, handing myself a verdict I can’t appeal.

Picture a basketball. Now picture me in a swimming pool forcing it underwater with both hands. See in your mind the effort required to keep it submerged. It’s enormous and exhausting and invisible to anyone standing at the edge.

I grew up in the ‘80s, where conflict between boys on the playground had options that aren’t available in a professional setting in 2026. Despite my exterior (I am a large man, shaved head with goatee, the kind of person who automatically gets placed in the threatening box in certain kinds of rooms), I am always, always fighting (not literally) to maintain a reputation worthy of respect. Which is double-hard when your position on the org chart carries no authority over anyone. No direct reports. No title that commands deference. Just the work, and the reputation the work builds, and a hope that the work is enough.

It isn’t always enough for everyone.

There are people in every workplace who use hierarchical status as a paintball gun. The shots aren’t lethal. They don’t end careers or break bones. But they hurt when they land, they leave a mark, and they take a while for the bruise to fade. And the person firing those shots knows exactly what they’re doing. They can’t come at me physically. So they engage with the hubris and self-importance that comes with a job title higher than mine, in public settings where a response would cost me more than silence.

They see a thin-lipped horizontal smile. Narrowed eyes. A brief, loaded silence while my mind runs scenarios of responses and outcomes in rapid-fire fashion. The mature high road of a dignified response of tacit Teflon. Or I let my hurt emotions let my mouth get the better of me and start wrestling a pig in the pen.

The pig enjoys it. I know this. I begrudgingly choose the Teflon.

The button is pressed, and the videotape starts recording.

When someone safe asks me about the impact of negative treatment, I look at them with a fairly straight deadpan face and say quietly: “I’m like a Chiquita banana. I bruise easily.” It’s the tragic comic attempting to provide humor while cautiously creating the possibility that I’m actually getting hurt. Which I am. The imposing exterior is not impact-resistant. It just looks that way from the outside.

Here is what I’ve learned to do instead of playing the tape over and over until it wears thin.

I pause a moment and look directly at the person. I say calmly: “Before I respond, I want to be clear about what you just said. My inner narrative is telling me that you...” and I name it, plainly, without accusation, without theater. Then I drop my voice slightly, and ask slowly: “Was that your intention?”

That question does more work than any comeback I’ve ever constructed on the VHS tape. It separates what was said from what was meant. It puts the basketball back in the other person’s hands without launching it out of the pool. It forces a moment of honest accounting for both of us. Before I say the appropriate thing, establish the boundary, or state a perspective to “manage up.” And I eject the VHS tape and put it back on the shelf.

I didn’t learn this in professional development training at work. I learned it in my marriage. In the unglamorous, humbling, necessary work of learning how to stay in relationship with the woman who means the most to me in the world, the person I chose. The communication skills I built at home to prevent ruptures in the most important relationship in my life turned out to be exactly the skills the professional setting needed and never thought to teach.

I brought them to work the way I bring everything to work: quietly, without announcing it, as a gift nobody asked for and nobody knew they were receiving.

I won’t pretend the “Was that your intention” subroutine has patched all the bugs in my SelfOS. The VHS tape still records sometimes. But I’ve learned not to make vows, because vows set things in motion that I don’t want to contend with. What I do instead is get to a place, after sitting through enough replays, where my inner narrative says: when the warning signs for this occur again, you will take this route. A subroutine, not a promise. A patch, not a pledge.

Interestingly, the gym helps with my SelfOS. Blaring loud music in my earbuds comprised of double-kick drums, chugging electric guitars, and shrieking vocals demanding full attention. Some may think that would be an audio paintball, but it gives my brain permission to stop processing what the silence and solitude of working remotely from home couldn’t interrupt. It takes a sonic blast to quit the review loop that quiet couldn’t. The same person who needs soft acoustic guitar albums on Saturday morning needs something completely opposite to forcibly reboot the system after a bad Wednesday. Both are medicine. Opposite prescriptions for opposite conditions.

If you recognize this videotape, you’re not broken. You’re someone who cares enough about the work, the relationships, and the standard to keep reviewing the footage. The cost of that caring is real. It lands on you in private, in places nobody thinks to check, and it fades away eventually without much fanfare.

My bruise from the professional paintball eventually fades. My subroutines get smarter. And somewhere in the gap between the paintball going thwack and the videotape finally switching to a static screen, I become more of the person I’m trying to be.

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