Stop Choosing Between Options. Start Choosing Between Futures.
You’re not picking between offers. You’re choosing who you’ll become next.
I was standing in my living room in Northern Ontario, staring at a job offer that made absolutely no sense to take.
On paper, it was a bad deal.
The pay for the government role in Ottawa was low. It would mean selling our house, leaving a small community where we had friends, roots, and a life we’d built. My wife at the time had a successful business there. We belonged.
Moving to Ottawa? We knew almost no one. She’d have to start from scratch. And all of it for a job that didn’t even pay particularly well. And housing cost way more.
Most people thought I was crazy to even consider it.
(Maybe I was!)
But I wasn’t comparing job offers. I was choosing between two futures.
You’re Comparing The Wrong Things
Most people make decisions by stacking options side-by-side:
- Job A salary vs. Job B salary
- Job A location vs. Job B location
- Job A security vs. Job B risk
They analyze every variable they can measure — and completely miss what they’re actually choosing.
You’re not picking between two jobs. You’re picking between two different people you’ll become.
The comfortable choice — the one that looked smarter on paper — would’ve kept me exactly where I was. Safe. Predictable. Stable.
The Ottawa job? That was a bet on a completely different future.
New skills. New exposure. New opportunities. A different version of who I could become.
I wasn’t comparing salaries or commutes. I was asking:
“Which path leads to the person I actually want to be?”
That’s the question most people never ask.
The Hidden Question Behind Every Decision
When people get stuck between options, it’s usually because they’re comparing snapshots instead of trajectories.
Take the entrepreneur debating going back to corporate. They compare salary (corporate wins), stability (corporate wins), benefits (corporate wins). So they go back.
But they didn’t compare who they’ll become.
Corporate life slowly makes you more risk-averse. It rewards politics over initiative. Three years later, you’re “safer” but you’ve lost the muscle for building things from scratch.
Or the person choosing between a promotion with brutal hours and a lateral move with better balance. They compare titles and money (promotion wins). So they take it.
But that path optimizes for achievement over aliveness. Three years later, they’re “successful” — but too tired to be present, too drained to enjoy what they worked for.
I could’ve stayed in Northern Ontario. The safe move.
That would’ve meant becoming more of what I already was — comfortable, rooted, stable.
But also… limited. Remaining in a small pond, with predictable outcomes.
Moving to Ottawa meant stepping into uncertainty. More challenge. More risk. But also more possibility. A bigger game.
I chose growth over comfort. And it changed everything for me.
How To Decide Between Futures
Forget the pro/con lists.
Instead, project yourself into each future and look around.
Ask yourself:
- Who am I becoming if I choose this?
- What skills am I building? What’s atrophying?
- Am I expanding or contracting as a person?
- How do I feel — energized, alive, or drained, dull?
- What stories am I telling myself about who I am?
- Am I becoming more of who I want to be, or just more comfortable?
Don’t think about the job. Think about the person.
When I imagined staying, I saw comfort and stability — but also regret.
When I imagined going, I saw possibility. Growth. Exposure. A self that bet on himself instead of playing safe.
The “smart” choice would’ve been to stay.
But I wasn’t optimizing for smart — I was optimizing for becoming.
What Makes This Hard
Every decision is a small act of self-definition.
Each one reinforces a story about who you are — or rewrites it.
Staying in the comfortable job? You’re voting for safety, for predictability, for more of the same.
Taking the scary leap? You’re voting for courage, adaptability, aliveness.
There’s no single right answer — only the one that leads toward who you want to become.
Most people never ask what they’re really optimizing for.
Safety or growth.
Comfort or aliveness.
The person they are — or the person they could be.
Your Move
When I took that government job, we sold our house, my wife closed her business, and we started over in a city where we barely knew anyone.
That bet changed everything.
New skills. New network. New opportunities that only existed because I put myself on a different trajectory.
I became someone different. Someone I actually wanted to be.
Stop comparing the perks, salaries, and titles.
Start comparing who you’ll become.
Get brutally honest about what you’re optimizing for — because whether you choose to stay or go, you’re shaping your future self with every decision.
Most people optimize for comfort and wonder why they feel stuck.
You don’t need a better option — you need a braver vision for what your life could be.
Quotation I’ve Been Pondering
“The future enters into us, in order to transform itself in us, long before it happens.”
— Rainer Maria Rilke
Journal Prompt
“If every choice is shaping who I’m becoming, what future am I unconsciously building through my current habits and decisions?”
Until next week!!
Work and live well.
Tim
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