Black and white drawing of a man’s head with a maze inside, representing introspective decision-making and thoughtful failure.

The Stupidity of Failing Fast: Why Better Leaders Fail Thoughtfully

The Illusion of “Failing Fast”

The startup world often glorifies the mantra “fail fast,” suggesting that rapid experimentation leads to extraordinary feats of innovation. Swift pivots are as intuitive as breathing and founders boast about it like they just won the big game. 

Sure, this approach may accelerate learning, but it often overlooks the very human and shockingly under-appreciated organizational costs associated with hasty decisions. Simply put, failing fast is stupid and it's time for a reckoning. 

The Fallout of Failing Fast

For just a moment, consider the actions of Elon Musk and DOGE. In an attempt to streamline federal operations, nearly 250,000 federal employees were abruptly dismissed, including critical roles in public health and safety.

The consequences were immediate and severe: disrupted services, eroded trust, and a workforce left reeling.

This isn’t just about numbers; it’s about people, dedicated professionals who found themselves collateral damage in a high-speed experiment.

When I initially posted about this, I received countless comments applauding the move, often citing efficiency as justification. "Let's blow it up," one person said, like we're at a gunfight at the O.K. Corral.

But  I can’t help but wonder: how many of them have been on the receiving end of an ‘efficiency consultant’ coming for their job? The cognitive dissonance is palpable. 

It’s easy to champion ‘failing fast’ when you’re not the one falling. But for those who are, the impact is profound. There's a strong sense of disposability that lingers long after the headlines fade

A Personal Reflection on Failing Fast

I get it. In my early days as an entrepreneur, I embraced the “fail fast” mentality, making swift decisions in the name of progress.

But I soon realized that speed without strategy is just chaos. Who the fuck wants to work with this guy? I saw talented team members burn out, projects derail, and trust implode, all because I prioritized haste over thoughtfulness.

Failing fast may sound efficient, but without intentionality, it's mostly reckless.

Embracing Thoughtful Failure

Failing thoughtfully isn’t about avoiding failure; it’s about approaching failure with a strategy, rather than throwing up a hail Mary.

It’s about being discerning, an approach that values deliberate decision-making, assessing risks, and understanding the potential impacts before acting.

It’s about recognizing that inclusive processes and gathering diverse perspectives aren’t just buzzwords or frivolous DEI initiatives; they’re essential because our stakeholders are our lifeblood.

Reflective practices aren’t optional; they’re our only way to control future outcomes. 

Sure, Musk glorifies speed and efficiency but taking time to reflect, include, and deliberate is what separates monkey from man; or Musk from man.

It's what separates real leaders from those who act hastily and deal with the fallout later.

The Path Forward: Failing Thoughtfully

In high-stakes environments, the impulse to act swiftly is strong. I feel that impulse too. It's coded and embedded in me.

But I'm no monkey. I get to choose how to be and I choose a mindset of failing thoughtfully.

I'm up to serious things and serious people make informed decisions and maintain the morale of the people they need most around them.

If intentionality is the highest form of intelligence, we should all move beyond the allure of speed. It's easy and unremarkable.

An Invitation

When you're ready to explore this topic with me, reach out.

There's no rush. Be intentional with your time. 😉

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Stephen Belenky

For over 15 years, Stephen has worked as a strategist, advisor, and coach to leaders tackling the challenges of high-stakes change. His career spans big business, scrappy tech startups, and global nonprofits, where he has helped clients resolve conflict, set bold directions, and build resilient teams.

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