Client #1, Part 2 — The Ace Up His Sleeve
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...

