You’d never put your whole portfolio in one stock. So why are you doing it with your life?
A couple of weeks ago, I got a letter telling me my “services may no longer be required”. I wrote about it — about why that letter didn’t break me, and why it likely would have destroyed me a decade ago.
But here’s what I didn’t write about: what that letter revealed about the bet I’d been making for twenty years. And the one you’re probably making right now.
Because the letter wasn’t the risk. The letter was just the audit. The risk had been sitting on my books the entire time — I just hadn’t been reading the statement.
You’d never put your entire investment portfolio into a single stock. You’d call it reckless. Maybe even stupid. But right now, you’re probably betting everything — your time, your identity, your best waking hours, your sense of who you are — on a single position you don’t even control.
And yet you call that “playing it safe.”
The Bet You Don’t Know You’re Making
Your paycheque shows up every two weeks. Your benefits are solid. Your pension is growing. From the outside, it looks like the most conservative play available. It feels safe.
But flip the ledger over and look at what’s on the other side, and you’ll find losses that aren’t nearly as obvious. You might not be aware of them, but they’re compounding daily.
- Your health is deteriorating — not dramatically, just slowly enough that you can pretend it’s “aging” instead of what it actually is.
- Your relationships are getting the exhausted, distracted, leftover version of you.
- Your curiosity — that thing that used to make you interesting — is flickering out because you haven’t fed it anything real in years.
And the gap between who you are at work and who you actually are keeps getting wider, until you’re not sure which one is real anymore.
That’s not stability. That’s concentration risk with a pension plan.
How I Know
I spent more than twenty-five years making this exact bet. Government executive. Cybersecurity. An interesting and in-demand field. Stable, respected, well-compensated. By every rational metric, it was the safest bet available.
But it nearly killed me.
I don’t mean that as a figure of speech, but literally. I burned out so severely I ended up in the hospital. And the root cause wasn’t the workload or the bureaucracy or the bad bosses (though all of those existed). The root cause was that I had fused my entire identity to my job. When the job went sideways, I went sideways. There was no separation between Tim-the-person and Tim-the-cybersecurity-executive. So when one collapsed, so did the other.
That crisis damn near destroyed my life. But it also saved it — because it forced me to confront something I’d been avoiding: my job and my Work were not the same thing, and I’d been pouring everything into the wrong one.
The Risk You’re Actually Avoiding
Here’s where I’m going to push you, because this is the part nobody wants to hear.
You already know what your Work is.
Maybe not the specifics. Maybe you can’t articulate it in a neat elevator pitch. But you know. There’s something pulling at you — a direction, a contribution, a version of your life that feels more true than the one you’re currently living. You’ve felt it in the quiet moments before you reach for your phone. You’ve sensed it when something lights you up and you immediately dismiss it as “impractical.”
You know.
And you’re not facing it because it’s uncomfortable. Because it’s uncertain. Because it doesn’t come with a job title, a benefits package or even a clear path to monetization. And because pursuing it means admitting that the life you’ve spent years building might not be the one you were supposed to build.
So you tell yourself you “don’t know what you want” — which is the most expensive lie you’ll ever tell. Because while you’re pretending you haven’t heard the signal, the meter is running. Every month you spend ignoring it is compound interest working against you — not in your bank account, but in the gap between the life you’re living and the one you’re meant to live.
Avoiding your Work isn’t playing it safe. It’s playing with fire. You’re just hoping the house doesn’t burn down before you retire.
The Transition Nobody Tells You About
I’m writing this from the middle of my own transition, not from the other side. I want to be honest about that.
I’m still in the government job. I’m also building something called Soulwork — helping people untangle their identity from their job title and figure out what they’re actually here to do. Trading “Cybersecurity Executive” for “Soulwork Strategist” feels, some days, like showing up to a poker game with Monopoly money. One title is understood immediately. The other requires a five-minute explanation and usually ends with the person nodding politely while clearly trying to figure out what I actually do. That’s the cost of building something new. I’d rather be hard to explain than easy to replace.
There’s a part of me that says I’m throwing away two decades of credibility. That I’m walking away from a sure thing for something unproven. That voice is loud, and it sounds a lot like reason. But I’ve learned to recognize it for what it actually is: cowardice with a spreadsheet.
I didn’t start building this new identity when the letter arrived a couple of weeks ago. I started years ago, after the burnout, after the hospital, after I realized I needed a version of myself that didn’t collapse when the job did. So when that letter showed up, it landed differently. Not because I didn’t care, but because my identity wasn’t riding on the answer.
That’s not luck. That’s what happens when you stop making a single bet and start diversifying the only portfolio that actually matters — who you are.
Three Ways to Rebalance
There’s no single right move here. But there are three legitimate strategies, and the right one depends on where you are, not where some motivational poster tells you to be.
1. Hedge the position.
Keep the job. Change your relationship to it. Stop asking your employer to give you meaning and start treating the role for what it is — a funding mechanism for the Work you’re here to do. Use the stability to build something on the side. Write. Create. Explore. Test.
But here’s the catch: you actually have to do the Work. If you’re collecting the paycheque and numbing out every evening, you’re not hedging. You’re just holding a losing position and calling it strategy.
2. Rebalance the portfolio.
Make a move. Take on a new role, join a new company, maybe build something of your own. But do it with a plan, not a tantrum. It’s fine to swim in the ocean — if you know how to swim, or at least have a life jacket on. What you don’t do is wade in over your head just because you’re sick of the shore.
Prerequisites: financial runway, a clear picture of what you’re moving toward (not just what you’re running from), and enough self-awareness to know the difference between courage and recklessness.
3. Reduce your exposure.
You decide the climb was a race you don’t want to win anymore. Not out of defeat — out of clarity. You know what “enough” looks like, and you stop chasing more for the sake of more. You downshift to free up bandwidth for the things that actually matter to you.
This one takes the most honesty, because it’s the easiest to disguise as wisdom when it’s actually fear. If you’re “simplifying” because you’ve genuinely recalibrated what matters — good. If you’re simplifying because the real Work scares you and a comfortable plateau feels safer than growth — that’s not a strategy. That’s hiding.
Run the Real Audit
I got that letter a couple of weeks ago, and I was okay. Not because nothing matters, but because I’d spent years quietly building a version of myself that wasn’t dependent on a single institution’s opinion of my value.
Most people don’t do that work. They wait for the letter — or the layoff, or the health scare, or the retirement party — and then realize they have no idea who they are without the job title.
Don’t be most people.
Run the real audit. Not the one on your bank statement — the one on your life. Look at where you’ve placed your bets. Ask yourself what your “safe” position is actually costing you. And be honest about whether you’re managing risk or just avoiding the Work you already know you’re supposed to be doing.
The most dangerous bet isn’t making a move.
It’s convincing yourself that standing still is a strategy.