The Poison of Perhaps
How hedging your bets leads to self-sabotage
You’re standing at the crossroads between comfort and uncertainty: one path brightly lit, predictable, and safe; the other shrouded in shadows, ambiguous but filled with possibility.
Today, we deceive ourselves by attempting to walk both paths at once.
We launch multiple projects to “see which one takes off”.
We keep one foot in our stable day job while dipping a toe in a startup idea.
We diversify every decision: financial investments, career moves, product strategies and even partners.
We do this in the hope that if one fails we’ll have a fallback to save us.
In short, we hedge our bets on almost everything.
But damnit. We’re trading Courage.
Today this is the dangerous default state for both individuals and organizations.
Teams spread focus across multiple features instead of betting big on a single bold idea.
Many career minded folks hesitate to specialize, preferring to keep broad skillset “just incase” the right career pivot worthy opportunity comes along. They fail to master their craft.
Leaders speak in cautious tones, couching opinions with “on the other hand” or “to be safe” so there is never too much skin in the game.
Look — I get it — confronted with rapid change and volatility its a rational response. Who doesn’t want insurance against failure?
The irony is that by never fully committing we still guarantee a kind of failure.
Sure, it’s not the dramatic spectacular “loss porn” on r/wallstreetbets when someone makes the wrong call on 0DTE options.
Rather a slow, subtle fizzle.
Projects that receive partial attention yield mediocre results. Careers that never venture far enough in one direction level of in the safe middle. Leaders who cloak every decision in “carefully calculated maybes” poison their teams’ abilities to achieve the extraordinary.
This is the hidden opportunity cost to perpetual hedging.
You and I seldom talk about it. Because on the surface everything looks fine.
Nothing’s on fire.
Nobody is bankrupt.
But something vital is missing.
Think about the times you’ve made a wholehearted decision. Maybe it was learning a new language in depth rather dabbling in three. Maybe it was choosing one book to read and then re-read deeply instead of opening five and getting through none.
Such all-in moments are when the real growth happens.
It’s easy to delude ourselves by exclaiming “we’re busy”. Yes, we’re busy going in circles: refining contingencies instead of forging ahead.
“It is not death that a man should fear, but he should fear never beginning to live.” — XII. 1
In a professional sense, never beginning to live is akin to never fully committing to our most important work.
It’s the risk of reaching the end of a project (or career) and realizing we never gave it our all.
We might have avoided the pain of a big failure, but we also missed the glory of that big success.
See, courage isn’t the absence of that fear; it’s proceeding in spite of it, guided by a conviction that the potential reward or learning is worth the risk. Where the water is so over our head we might (just maybe) learn to swim stronger.
What Courage Really Means Now
Courage today doesn’t mean charging blindly into danger.
It often just looks like focus.
I admit I wasn’t always courageous.
In fact, I spent years hedging myself. I’ve had many insights and ideas for products but settled for coordinating others to maybe build something I thought was valuable. Instead of getting my hands dirty.
I felt my development skills grow rusty, so I rationalized that my strength was in “managing” and “strategizing” — a convenient hedge that kept me from learning the new tools that excited me.
It took a friendly nudge and the power of AI applied in the IDE to jolt me out of that complacency. It was:
In a matter of months, I went from delegating every technical task to building something new almost every day.
The flood of progress and creativity in that period was staggering. And still is.
The only thing that has really changed is my mindset: I stopped hedging and started doing.
The courage to dive in fully — to be a beginner again, publicly and unabashedly — reignited my growth. Playing it safe never could.
Courage is a willingness to look foolish in the short term because you see a possibility that others don’t. Its doubling down on a passion and trusting the journey will be worth it.
Paradoxically this kind of courage can create its own safety: being deeply committed to a vision increases the probability of a breakthrough (and security).
For Those Who Dare
A few guiding practices to break that temptation to hedge:
Identify your crutches. Be brutally honest: in what areas are you keeping a Plan B always at hand? It could be a project you haven’t killed or a job opportunity you keep “just in case.”
Commit to your core idea (at least for a while). Don’t go burning all your bridge but pick a single important goal and go all in it on for a set period of time. Remove the escape routes to force yourself to persist.
Reframe failure as feedback. The courageous mindset treats failure as data — a step closer to getting it right.
Take ownership. True courage means accepting the risk and it’s on you. If it fails it’s on you. If you succeed: well then! This helps to build pride and accountability that hedging never will.
Say to yourself: “This is the path I’ll take” even with clouds of uncertainty hanging overhead.
But please just don’t attempt both at once.
It’s great to be daring together!