Tags: leadership, blog
By any meaningful metric, a former executive of mine was a failure. Revenue targets? Missed repeatedly. Team morale? Cratered. Results? Nonexistent. He was eventually fired.
But check his LinkedIn today, and you’d think he architected a unicorn IPO. Post after post paints strategic brilliance, team-building mastery, and hard-won success. No mention of missed goals, chaos, or human cost. Just curated leadership platitudes and sanitized takeaways.
This isn’t rare. It’s become the playbook. A certain type of leader fails spectacularly, and instead of reckoning with the wreckage, they quietly rebrand it as triumph.
This phenomenon isn’t limited to tech. Take Hue Jackson, former Cleveland Browns head coach. Across two full seasons (2016-2017), his record was 1–31. One win. Thirty-one losses. This gives him the dubious distinction of having the worst two year record in recorded NFL history.
When fired, Jackson remained adamant he was the right coach. On ESPN’s First Take:
“I think it was a little premature… any time there’s all these undercurrents going, there’s something in there.”
Despite the record, blame was never personal. Always external, always circumstantial. He even implied the Browns were intentionally tanking; claims that a 2022 independent investigation found unsubstantiated.
Jackson’s playbook of failure was simple: blame external factors, claim misunderstanding, and promise future success. This template for failed leaders has become honed to perfection in Silicon Valley.
The king of the rebrand might be Adam Neumann. After overseeing WeWork’s spectacular collapse, involving a failed IPO, massive layoffs, and billions in losses, Neumann didn’t fade into obscurity. Nor was he humbled. Instead, he positioned himself as a misunderstood visionary whose successors couldn’t execute his grand vision.
On WeWork’s bankruptcy:
“It has been challenging for me to watch from the sidelines since 2019 as WeWork has failed to take advantage of a product that is more relevant today than ever before.”
Note what’s missing: any acknowledgment of the $19 billion in debt, thousands of layoffs, or investors who lost everything. Instead, it’s WeWork that “failed to take advantage” of his perfect vision.
Years later, launching a new startup backed by hundreds of millions, he said of WeWork:
“I am so proud of what we did… I think very few people disrupt categories and very few companies reinvent categories. Office is the second largest category in the world. And I’m very proud of what was achieved.”
He’s not spinning the story; he’s rewriting it entirely.
This self-mythologizing doesn’t just shield the leader, it harms the organization. When leaders fail spectacularly and then rebrand their failures as triumphs, it actively harms those left behind. Teams that bore the brunt of the poor decisions watch as the person responsible walks away unscathed, sometimes promoted. They see spin win and substance lose.
It sends the wrong message to emerging leaders: perception matters more than performance. Style gets rewarded. Reflection is optional.
One maddening aspect is that spectacular failure rarely ends careers, instead it often leads to new opportunities. The revolving door of leadership means even the worst failures don’t close doors, they just shift them.
In these circles, failure isn’t just survivable, it’s often irrelevant. Once you’re in the inner circle, the system recycles you. Especially if you speak in sweeping vision statements, appear confident under pressure, or stay close to capital and influence.
Proximity to success is often enough to keep you in the game, even if you never deliver.
I once worked at a startup led by a well-connected, technically excellent founder. Over time, almost imperceptibly, they prioritized visibility over viability. The drift was subtle but telling: marketing materials got refreshed while deals were not pursued. Team awards were celebrated while the business languished. External validation became more important than internal execution.
When the inevitable economic downturn hit, there was no “next big deal” because the founder had been subconsciously prioritizing optics over operations. They had been more focused on building a brand than a business.
This pattern is common in founder-led companies. Leaders become more focused on the optics of leadership than the actual work of leading.
Not everyone gets the luxury of failing upward. While some leaders glide from role to role, talented people fall once and never recover.
If you’re not in the inner circle, there’s no revolving door. Miss a target or get caught in a failing project, and you’re out. Worse, some people never get the chance to fail. Risk tolerance shrinks dramatically if you’re a woman, person of color, or first-time founder without a blue-chip résumé.
That’s what makes the mythologizing so corrosive. It’s not just about how some people spin failure, it’s about how others never get the chance to recover from it.
Not every polished narrative is a lie. It’s okay to put a positive frame around hard lessons. Saying “Here’s what I learned” after a stumble isn’t spin, it’s reflection.
Self-mythologizing skips the hard part. It dodges accountability, turns real damage into vague wisdom, and reframes failure as inevitable brilliance. It’s tidy, self-serving, and detached from reality.
Telling the truth is different. It’s messy. It requires humility and vulnerability. It means saying, “I messed up, and here’s how I’m working to fix it.”
Your gut reaction when you realize the story you’re telling doesn’t match reality? That’s a good indicator of whether you’re mythologizing or reflecting.
I’ve worked with leaders who got it right. Who owned their mistakes. Who asked hard questions and listened to hard answers. Who said, “I messed that up,” and meant it.
They didn’t always win. But they built trust. That trust remains long after the job title changes.
The hard truth: the appearance of success is more valued than actual success. Look the part, speak the lingo, manage up effectively, and you can fail in all the ways that matter while still landing the next opportunity.
Doing the right thing when nobody’s watching? Admitting fault when every instinct screams to deflect? That’s the real test of leadership.
People remember how you made them feel. Who backed them. Who told the truth. That’s your legacy.
The next time you see a leader posting about “lessons learned” from their spectacular failure, ask yourself: Are they sharing wisdom, or workshopping their comeback story?
The difference matters; not just for them, but for everyone watching.
Authentic leadership isn’t about crafting the perfect narrative. It’s about being real, even when it’s uncomfortable. It’s about acknowledging that failure is part of the journey, not a badge to be polished and paraded around.