The Hypocrisy of 'It's Ok to Fail': A Luxury Only for the Top?

When Failure Is Safe for Some but Costly for Most

“It’s ok to fail.”

It’s the phrase of the century, a mantra touted by high-flying founders and leadership coaches alike. We see it in motivational talks, startup off-sites, and LinkedIn posts by everyone from CEOs to HR managers. But is this rallying cry really accessible to everyone, or is it an empty platitude—something reserved for those with the security to take a fall? For most on the ground, failure comes with higher stakes and consequences than those slogans would suggest.

This is the story of how “It’s ok to fail” became both a corporate buzzword and, for many, an unattainable ideal.

The Product Launch Debacle

Meet Rohan, a mid-level product manager at an edgy, fast-growing tech startup. Like many young professionals in the tech industry, he’s bought into the “fail fast, fail forward” mindset—or at least he thought he had. That is until a recent project turned into a fiasco. Rohan had spearheaded a new product launch, one hyped to add value to the company’s brand. But within two months, it was clear the feature wasn’t gaining traction.

So, Rohan goes to his boss, expecting a failure-friendly response, hoping for constructive feedback that aligns with the company’s “fail forward” philosophy. But the review isn’t friendly, or constructive. “Maybe we need to re-evaluate your focus here,” his boss says, nonchalantly. A quarterly review is suddenly on hold. For Rohan, it’s as if the whole "failure-friendly" mantra was just a fairy tale.

What Rohan experiences is not unique. In fact, it’s a striking example of the double standards pervasive in startup culture: at the top, failure is spun as a stepping stone to growth, while for the rest, it’s a career-limiting mistake.

The Double Standard

This dissonance only sharpens in Mira’s story. She’s a junior developer at a similar startup, and last week, she watched her CEO passionately advocate for the “It’s ok to fail” mindset at an all-hands meeting. She felt empowered. But a week later, a small coding error triggered an email chain from the same founder, cc’d to her entire team, emphasizing that “there’s no room for these kinds of mistakes in client-facing projects.” When Mira tried to explain herself, her manager’s response was curt: “We don’t have the luxury of failure here.”

Mira’s story is yet another example of how the philosophy of embracing failure rarely permeates down the ranks. Leaders may preach resilience, but when that ethos isn’t reinforced at every level, it becomes a hollow echo. For employees like Mira, the gap between the message and the practice leaves them grappling with the very real fear that even small slip-ups could jeopardize their standing.

A Mentor’s Confession

For those at the top, embracing failure wasn’t always part of the playbook. Take Rajesh, a well-respected startup mentor who now advises his mentees on resilience. He preaches about “celebrating mistakes” and encourages others to “try and fail.” But Rajesh himself didn’t start his career with this mindset.

In a rare moment of honesty, he recalls his own startup’s early days, when failure was out of the question. “Back then, any mistake could have meant losing investors,” he admits. “We couldn’t afford a single misstep.” His view on failure evolved only after the company stabilized—once he had achieved enough success that a few mistakes wouldn’t threaten his entire career. This confession illustrates a harsh reality: even those who now preach failure only embraced it after they were out of the woods.

The Internal Memo

Sometimes, the stakes are high enough to override any pretense of a “fail-safe” culture. In one fast-scaling startup, employees rallied behind the company’s “failure is growth” philosophy. Then, a memo leaked. The board was furious with the startup’s performance, warning that, “This is the last quarter we’re on thin ice.” The “failure-friendly” mantra quickly vanished as managers clamped down on mistakes, putting pressure on teams to perform without error. For ground-level employees, the pressure was real, and failure—however noble in theory—simply wasn’t an option anymore.

This particular startup’s story illustrates the often-hidden but very real pressures that shape company culture. It’s one thing to advocate for resilience, but when a company’s survival is at stake, even the most well-meaning organizations shift their priorities.

Failure: A Luxury of Success?

The message becomes clear: “It’s ok to fail” is often a luxury only available to those with a cushion—both financial and reputational—to absorb the fallout. Top-level leaders can champion the philosophy without suffering the direct consequences that ground-level employees face. And as they climb higher, even they may find their stance on failure becomes less tolerant as their responsibilities grow.

Failure, at the end of the day, can be transformative and invaluable, but for many, it’s a privilege. The next time someone says, “It’s ok to fail,” it might be worth asking: is that advice genuine, or merely a line to rally the troops?

Inspired by this Quote: by a famous Business Coach "It’s ok to fail......"