Failing Upwards

Beyond the Cautionary Tale: Survivorship Bias as Strategic Insight #

Survivorship bias—our tendency to focus on successful outcomes while overlooking failures—typically enters conversations as a cautionary note. We’ve all witnessed this dynamic: someone celebrates a remarkable success story, only to have another person interject with the observation that “that’s just survivorship bias,” effectively suggesting we should discount the achievement as statistical noise rather than meaningful evidence.

This critical application of the concept certainly serves an important purpose in tempering unrealistic expectations and protecting us from flawed conclusions. However, what’s often missing from these discussions is how to transform this cognitive insight into practical strategy. If we accept the premise that many celebrated successes—whether in entrepreneurship, investing, relationships, or literal lotteries—contain substantial elements of fortunate circumstance alongside skill and effort, a more nuanced and productive question emerges:

How might we systematically position ourselves to benefit from this probabilistic reality rather than merely using it to discount others’ achievements?

Strategic Risk Management in Probabilistic Environments #

Generating meaningful returns in any domain—whether financial, professional, creative, or relational—inevitably requires embracing calculated risk. A fundamental principle in risk management suggests that expected rewards generally correlate with both the magnitude of risk undertaken and the probability of successful outcomes. However, if we acknowledge that success contains significant probabilistic elements beyond skill alone, we can develop more sophisticated strategies for positioning ourselves advantageously within these uncertain landscapes.

Several evidence-based approaches can systematically improve our relationship with favorable probability:

Adaptive Sequential Experimentation #

We can implement variations of the martingale strategy, which involves placing a series of calibrated small bets and methodically adjusting our resource allocation based on continuous feedback. Unlike the problematic gambling application of this approach, a thoughtful adaptive strategy involves:

• Starting with small, affordable experiments that provide meaningful information
• Carefully analyzing outcomes of each attempt to extract actionable insights
• Progressively increasing investment in approaches showing promising signals
• Quickly pivoting away from directions demonstrating clear negative patterns
• Maintaining sufficient reserves to sustain multiple sequential attempts

Opportunity Surface Expansion #

Perhaps the most powerful probabilistic advantage comes from systematically increasing our exposure to potential opportunities. By diversifying our endeavors across multiple domains with limited correlation, we create multiple potential pathways to success. This principle forms the mathematical foundation of modern portfolio theory, which demonstrates how thoughtfully combined risk exposures can create more favorable aggregate risk-reward profiles than any individual component could provide independently.

Catastrophic Risk Mitigation #

Finally, sustainable risk-taking requires implementing minimax principles—strategies that minimize potential maximum losses while preserving upside potential. This approach acknowledges that not all risks are created equal: some threaten temporary setbacks, while others could permanently eliminate our ability to continue participating in the game. By designing our risk exposure to protect against complete resource depletion, we ensure our ability to persist through multiple iterations—a critical requirement for benefiting from probabilistic opportunities over time.

The Art of Productive Failure #

These strategic frameworks converge on a powerful mindset shift I call “failing upward”—a deliberate approach to setbacks that transforms them from discouragements into catalysts for growth. Failing upward represents a distinctive response pattern: when you encounter inevitable setbacks, you maintain forward momentum rather than becoming immobilized by disappointment.

Directional Failure: Upward vs. Downward Trajectories #

The directional quality of failure deserves careful attention. Consider two contrasting scenarios following the same initial setback:

Upward Failure resembles a momentary stumble during a continuous journey—you acknowledge the fall, extract valuable insights, adjust your approach as needed, and continue forward with minimal interruption to your overall trajectory. The setback becomes integrated into your development rather than derailing it.

Downward Failure, by contrast, involves becoming psychologically anchored to the disappointment—remaining metaphorically on the ground, ruminating on the fall, developing narratives of personal inadequacy, and potentially waiting for external rescue rather than self-initiated recovery.

The Psychological Foundation of Resilient Progress #

At its core, upward failure involves cultivating a refreshed perspective after disappointment—recognizing that while a particular endeavor didn’t yield desired outcomes, you retain the capacity to redirect your energy toward alternative opportunities or refined approaches to the same goal. This psychological resilience creates a sustainable foundation for continued experimentation.

Upward failure embraces the realistic expectation that most specific attempts in life won’t perfectly match our initial vision, while simultaneously maintaining confidence that the cumulative effect of persistent, learning-oriented effort creates substantial momentum over time. As I’ve explored in greater detail in my examination of how skills and experience compound, consistent investment in growth-oriented activity—even through frequent setbacks—creates exponential returns through the accumulation of capability, perspective, and opportunity recognition.

The Primacy of Interpretation #

Perhaps most importantly, your cognitive framing of failure fundamentally determines its impact on your development trajectory. Given that setbacks will significantly outnumber perfect successes in any meaningful pursuit, developing a productive relationship with failure becomes an essential life skill rather than an optional psychological nicety.

The ultimate downward failure—one that guarantees stagnation—is disengagement from the iterative process entirely. By contrast, maintaining engagement with the challenge, despite temporarily disappointing outcomes, preserves the possibility of eventual breakthrough that complete withdrawal eliminates.