Prominent business figures are highlighting a hard truth about leadership: failure hurts, but it teaches. Referencing experiences shared by Jeff Bezos, Sam Altman, Brad Smith, and Stephen A. Schwarzman, the message lands with fresh urgency as companies face rapid shifts in technology and markets. The lesson is simple and timely. Learning from mistakes can guide strategy, culture, and risk-taking across industries.
“Setbacks are terrible, but they also are great teachers.” — Stephen A. Schwarzman
A Shared Lesson From High-Profile Leaders
Schwarzman, the co-founder of Blackstone, has long argued that leaders improve by studying what went wrong. He joins a group of executives who have voiced similar views. Bezos has written to shareholders that large failures are the price of invention. Altman navigated a governance shock at OpenAI in 2023. Smith, Microsoft’s president, has weathered regulatory fights that reshaped the company’s approach.
These leaders work in different sectors, but the theme is the same. They treat missteps as feedback. They use setbacks to refine goals and change course. The idea is not new, yet it remains rare in practice when pressure rises and stakes run high.
Track Records Marked by Missteps
Examples from recent decades show how painful episodes can reset strategy.
- Jeff Bezos saw Amazon’s Fire Phone flop in 2014. The company took a write-down of roughly $170 million and cleared unsold units.
- Sam Altman was briefly ousted by OpenAI’s board in November 2023, then returned days later after staff and investor pressure, prompting board changes and a governance review.
- Brad Smith helped steer Microsoft through major regulatory scrutiny of its $69 billion Activision Blizzard deal. The U.K. initially blocked the deal in 2023. Approval followed after the company reworked terms to address concerns.
- Stephen A. Schwarzman managed Blackstone’s exposure during the 2008 financial crisis, later discussing how the firm changed risk controls and deal timing.
Each case brought public criticism and financial or reputational costs. Each also led to process changes. Leaders adjusted product bets, governance structures, legal strategies, or investment pacing.
Why Failure Can Strengthen Strategy
Setbacks force choices. Companies often re-examine decision rights, metrics, and where to place capital. They revisit assumptions about users, regulators, and partners. This can sharpen priorities and cut vanity projects.
Bezos has argued that experimentation needs room for error. The idea is to place many small and some large bets, accept losses, and scale what works. OpenAI’s board episode showed how governance gaps can disrupt operations. The response—adding independent oversight and clearer roles—reflects a common fix after crises.
For Microsoft, the Activision saga showed that early, detailed remedies can shorten regulatory battles. Smith’s public outreach, commitments on cloud and gaming access, and revamped deal terms signaled a more cautious path to mergers under strict review.
Multiple Viewpoints on Risk and Resilience
Supporters say learning fast from visible errors builds trust. They believe transparency—owning missteps and showing steps taken—can calm investors and staff. Critics warn that celebrating failure can excuse poor planning. They argue that disciplined testing and staged rollouts reduce avoidable mistakes.
Both views point to a middle path. Leaders must set clear guardrails while protecting room to try new ideas. The key is to capture lessons in writing, shift incentives, and follow up with measurable changes.
Signals for Workers and Investors
Investors often watch for three signs after a setback: a frank account of what happened, specific corrective actions, and evidence those actions stick. Workers look for psychological safety and fair accountability. Without those, the same errors repeat.
Companies that turn setbacks into systems change usually do three things:
- Document the root causes, not just the symptoms.
- Change processes, ownership, or incentives.
- Publish milestones and track progress over time.
Schwarzman’s line captures the trade-off. Failure hurts in the short run, but it trains judgment. Bezos, Altman, and Smith have reached the same conclusion through very different trials. The coming year will test how well these lessons hold as AI, regulation, and capital costs shift again. Watch for executives who admit what went wrong, show their fixes, and invite scrutiny. That is where real learning tends to stick.
