When I first launched BlockPR, it often felt like I was sitting at a poker table with everything on the line. Do I go all-in or play it safe?
Every founder knows that feeling: the tension between ambition and self-preservation. You’re constantly weighing outcomes you can’t fully control. The stakes are high because every decision could shift your company’s path.
That pressure used to overwhelm me until I learned this: growth doesn’t come from blind courage; it comes from calculated risk.
Risk isn’t reckless
There’s a myth in entrepreneurship that risk-taking equals bravery. But most successful founders aren’t gamblers. They’re navigators. They map the terrain before moving, then commit when the odds align with their conviction.
Like Ben Horowitz wrote in The Hard Thing About Hard Things, some decisions test your courage more than your intelligence. You already know what to do: the real challenge is managing fear.
Over time, I built a rhythm for decision-making. It’s not a perfect system, but it keeps me from freezing when uncertainty hits.
Define the opportunity. What exactly could this unlock if it works?
List the risks. Name them clearly — vague fear clouds judgment.
Play out the worst-case scenario. Could I recover from it? If yes, it’s worth considering.
Ask for trusted input. Not for validation, but perspective.
Check your gut. Logic is a map; instinct is the compass.
This process turned what used to be panic into pattern recognition. I could see risks for what they were: not threats, but levers.
The “premortem” mindset
Robert Sutton’s book Scaling Up Excellence introduced me to a method that changed how I plan: the “premortem.”
Instead of waiting for a postmortem after failure, you imagine the project already failed, then ask why. That mental rehearsal forces you to surface blind spots early.
It’s humbling work. You confront uncomfortable truths: weak assumptions, overconfidence, poor timing. But that discomfort is what strengthens judgment.
For founders, this mindset builds resilience. You stop chasing perfect outcomes and start designing for survival.
Of course, reflection has its limits. Spend too long analyzing, and you’ll miss the moment.
This is where many founders stall, trapped in what I call “decision purgatory.” Every new data point adds another reason to wait. But clarity rarely appears before movement.
Jeff Bezos approached this through what he called the “regret minimization framework.” When deciding whether to leave Wall Street to build Amazon, he imagined himself at 80, looking back. Would he regret not taking the shot?
That mental trick simplifies everything. The pain of temporary failure fades faster than the sting of lifelong hesitation.
I’ve learned the same lesson. My biggest regrets aren’t the bets that failed, they’re the ones I never placed.
Starting BlockPR was one of those bets. I had no guarantee it would work. The market was saturated, the Web3 sector volatile, and the PR industry full of noise. But the opportunity felt real.
That leap taught me that most growth comes from discomfort, not chaos, but controlled risk. Expanding services, entering new markets, even hiring ahead of revenue, each move scared me at first. Yet each became a catalyst for the next stage.
Calculated risks compound. You learn faster. You attract better people. And when setbacks hit, and they always do, you’ve already built the muscle to handle them.
Building a culture of smart risk-taking
Once you lead a team, the equation changes. You’re no longer gambling just your own comfort; you’re holding everyone’s livelihood in your hands.
That’s why culture matters. A team that’s afraid to make mistakes won’t innovate. But a team that takes risks without accountability burns out fast.
Here’s what I’ve found works:
Celebrate bold attempts, not just results. A failed experiment that teaches something is still progress.
Treat errors as data. Frame postmortems around learning, not blame.
Create safety nets. Encourage initiative but make sure the fallout from failure is manageable.
Model the behavior. If you never take risks, no one else will.
A healthy risk culture isn’t about constant action. It’s about discernment, knowing when to move and when to pause.
There’s a sweet spot between impulsiveness and paralysis. You reach it when you trust both your preparation and your ability to adapt.
In startup life, risk never disappears; it just changes form. In the early days, the risk is survival. Later, it’s stagnation. The same instinct that once told you to play it safe might later be what holds you back.
That’s why “smart risk” isn’t a one-time strategy, it’s a practice. It evolves as you do.
Every major leap I’ve taken followed the same pattern: clarity, calculation, then courage. Not the other way around.
When you strip away the noise, risk-taking isn’t about fortune or failure. It’s about self-trust, the quiet belief that you can handle what comes next.
And if you can do that, you’re already playing the long game.
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