Career change

I used to be able to play the piano.

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Unused piano with sheet music gathering dust

Your Skills Are a Snapshot, Not a Ceiling A skill I once had, gathering dust. || Prompted by me, generated by AI. We think of our skills as though they’re an inventory. And in some ways, they are. I’m good at this. I know how to do that. I’ve never been good at this other thing. Then we use that inventory to decide what seems possible for us. The problem is that your skill set isn’t fixed. It’s a snapshot of what you know how to do right now. Your skill set is fluid. Skills develop through…

My Body Still Thinks I Have a Job

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Hand reaching for a phone out of habit after the job has ended

Retiring the idea of retirement The reflex outlasts the reason for it. A few days ago, I retired. The pension paperwork is filed. My government job is over. The employment contract, the paycheque, and the schedule that belonged to someone else all ended at once. My body still thinks I have a job. A couple of times a day, I catch myself reaching for my phone to see if there’s something I need to handle. There isn’t. Nobody is waiting for an answer. I don’t even have a work phone anymore….

I had an amazing life. So why wasn’t I happy?

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Clothes that used to fit, hanging unused beside a life that still looks good on paper

You’re Allowed to Outgrow What You Once Wanted Better is always possible, but better doesn’t always mean more. It used to fit. You’re allowed to want something that now fits better. A few years ago, I was sitting in my favourite room of our house, drinking coffee and looking through a wall-to-wall window facing the Ottawa River. It’s a ridiculous view. Water stretching out in front of me, trees on both sides, ducks paddling around. It’s the kind of place people rent for a week or two to…

You were never paid for your effort

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Open exit doorway framed as the point of the path, not a failure

Markets Don’t Reward Hard Work — They Reward Value Turns out the exit was the point. For 27 years, I thought I was being paid for my effort. I stayed late. I took on the ugly projects that many steered clear of. When something caught fire, I was the one they called, and I enjoyed being the one they called. I was wrong. The reward was real. The effort got me better performance ratings, bigger files, a name for being the guy that got shit done. Now that I’m on my way out the door, I’m seeing…

You’re Not Lost. You’re Camping.

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Compass held on a wooded trail with no map in sight

You’re Not Lost. You’re Camping. “Job hugging” feels like safety. It’s not. No map needed; just a bearing. I’m a hiker, and have spent my share of time in the bush. I like to venture off the well-beaten paths, the kind of terrain where your phone loses signal around hour two. Every hiker learns the same rule early: if you get lost, stop moving. Stay exactly where you are. Make yourself loud, make yourself visible, and wait. The moment you start wandering to “find your own way out,” you cover…

You’d get fired for running a project this way

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Brass compass resting on architectural plans in a dark office

The Most Important Project You Keep Ignoring A heading, not a prophecy. You’ll invest heavily in planning a major project at work without blinking. Then leave your own life to chance. I’ve run complex programs for the government for years. Scope documents. Milestones. Risk registers. Budgets tracked to the dollar. When something threatened to go sideways, I usually saw it early enough to do something about it. It took me into my mid-40s to notice I’d never once pointed any of those skills at…

You’re telling the wrong person your story

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Person at a desk writing their own pages under a lamp

You’re Telling the Wrong Person Your Story The org’s draft is always ready. Yours needs to be too. Recently I gave a talk to 38 cybersecurity professionals about how to communicate so their work actually lands. Not just reports, dashboards, briefings, and risk registers, but meaning. The whole talk hinged on one idea: there’s always a story being told about your work, and if you don’t tell it, someone tells it for you. Be the storyteller, or be a character in someone else’s story. I didn’t…

Four AI Strategies. One Clear Winner.

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Person on a rocky shore facing a huge incoming wave

Four AI Strategies. One Clear Winner. The wave is coming. The only choice is how you choose to meet it. Your company just announced yet another AI initiative. Your LinkedIn feed is full of think pieces about the jobs it’s going to kill. Your colleagues are either panicking or pretending it isn’t happening. You’re not sure which is worse. Fear is useful when it alerts you to danger. It becomes a problem when it becomes your entire strategy. See the data from a recent Angus Reid poll: 57% of…

The Company Was Never Loyal to You

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Person with a box walking the aisle of an empty office

The Company Will Always Keep Its Options Open. So Should You. The math changed. And the office keeps going without you. Last week, Avishai Abrahami — CEO of Wix — sent a letter to his entire company. It was warm. It was honest. He talked about saying goodbye to friends, people he’d worked alongside for years, people he trusted and respected. Then he laid off 1,000 of them. Twenty percent of the company. Gone. And he wasn’t wrong to do it. The math was no longer working. Currency pressures, AI…

Nobody’s Stopping You. That’s the Problem.

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Person sitting inside an open cage while a key hangs in the doorway

Nobody’s Stopping You. That’s the Problem. The door was never locked. If I asked you what problem you’re solving at work, you’d give me a masterclass. Risks. Tradeoffs. Dependencies. Stakeholders. All the things. You can think your way through chaos with impressive precision. But if I asked what you really want from your work? Suddenly, you’ve got nothing. Not because the answer isn’t there. But because the moment the true answer showed up, your analytical brain stepped in and immediately…

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