Go, Fight, Win.

Playing the devil’s advocate against the value of failure in a world far too full of it

For the last couple decades, messaging surrounding the value of entrepreneurial failure has provided insurance for innovators to pursue risky ideas with little reservation. A ridiculous amount of lore around failure in modern academia and entrepreneurship has since precipitated from the fallout, with some authors going so far as to describe success as a story entirely contingent on failure. Before anyone could really second-guess the whole thing, we have surrounded ourselves with much literature reifying failure as a surprisingly desirable outcome.

Why has failure become so popular? For me, three reasons immediately come to mind:

  1. Educational value: It’s rational to believe humans substantively improve after failure. We’re logical beings, so, more often than not, we tend to avoid making the same mistakes more than once.

  2. Emotional value: There is some amount of gratification that is experienced in conducting postmortem analyses. Detailing the when, how, and why’s of our failures help us feel more confident in tackling future problems.

  3. Cultural value: Narratives of redemption are uniquely inspiring. We remember successful individuals who capitalized on lessons from past failures because these stories can be relatable and romantic.

While there are probably some arguments I’m missing here, these reasons alone suggest failures can make for some incredibly good writing. Try hard enough, and in nearly every failure one can find a compelling story to tell, an interested audience to sell it to, and a nominal amount of education to provide other people with.

Despite the quality of stories that tend to precipitate from failure, I believe much of our obsession with extracting value out of failure is pretty flawed. To me, the belief that we are able to “learn from failure” is predicated on the world in which a failure occurs remaining consistent among repeat encounters with a specific problem, a large assumption that doesn’t necessarily hold true in today’s world. As a result of this, I think we’re much worse at tracing back and root-causing failures than we think we are, an effect Thiel refers to as “over-determination” in an old podcast with Tim Ferris:

 “Most businesses fail for more than one reason. So when a business fails, you often don’t learn anything at all because the failure was over-determined.

“You will think it failed for Reason 1, but it failed for Reasons 1 through 5. And so the next business you start will fail for Reason 2, and then for 3 and so on.”

Although this critique clearly doesn’t hold true in some highly defined, rule-based systems, failure elsewhere does present quite an unpredictable enemy, and it is exactly because we lack all the information required to eliminate its possibility that we begin hallucinating in our pursuits to find quick and simple answers to hard, multitudinous questions.

Ultimately, the issues above stem from the idea that the problems we are failing at now tend to be complex beyond the possibility of much useful reflection, however attractive such a reflection may seem when this is the case. While many reflections on failure show nuance and probably do have legitimate lessons associated with them, there are actually not all that many times we see ourselves explicitly citing prior lessons derived from failure as critical reasons for success later on.


Even if there is value to be had from reflecting upon failure, it feels to me massively overrated, at least relative to the value of success. I believe a large part of this effect can simply be attributed to a disparity in empathy, especially when a failure seems inadvertent and appears publicly. We’ve all made mistakes before, so more often than not we hope for others the recovery we once hoped for ourselves. On the contrary, there’s a celebration in every success, and the occasion calls for surprisingly little further commentary. Beyond just this “win”, however, success is also a fundamentally more productive experience. Jason Fried puts this quite bluntly in Rework:

Another common misconception: You need to learn from your mistakes. What do you really learn from mistakes? You might learn what not to do again, but how valuable is that? You still don’t know what you should do next.

Contrast that with learning from your successes. Success gives you real ammunition. When something succeeds you know what worked — and you can do it again. And the next time, you’ll probably do it even better.

A study on performance persistence Rework later cites substantiates this. After reviewing thousands of entrepreneurs’ performances*, researchers at Harvard Business concluded that while already-successful entrepreneurs are more likely to go on to found successful businesses, entrepreneurs whose companies failed the first time are almost no likely to do any better in future ventures than entirely new entrepreneurs. These results suggest that (with respect to the problem of starting a new venture) failure actually had little to no effect on future success, while the experience of initial success did. Other, more recent studies have also arrived at similar conclusions, with this study of nearly ten thousand German venture-backed companies even identifying entrepreneurs that experience failure as more likely to fail in the future.

*: Only venture-backed companies are surveyed, and success in the study is defined as going public or filing for public offering. Some arguments suggest conclusions from exclusively venture-backed companies may not be representative of the entire entrepreneurial population.

Perhaps the greatest issue with reporting failure as a predictor of success for new ventures is not merely its factual inaccuracy, but the way it encourages the evaluation of business prospects to be rooted in some artificial narrative, rather than in people and ideas. For the aspiring entrepreneur, I believe this framing is dangerous. On the scale of individual actors, mantras like “fail early, and fail often” encourage innovation without prudence. They lower the critical thinking required to focus time, skill, and capital into building a product, in a mechanical, brute-force search for good ideas. When such expenditures prove fruitless in their pursuit, as they often do, they rehabilitate people involved, enabling them to swiftly return to the culture of “reckless failure” they once embraced. Within this circular, self-fulfilling prophecy, our very definition of failure gradually morphs, turning prior failures into justification for future success and present failures into “necessary costs” they never were. I think we really need to escape this cycle, however purposeful or healthy the concept of a trivial failure appears. Instead, we should despise failure and study our successes, doing whatever we can (while in our power and aligned with our beliefs) to avoid “learning the hard way”, lest we end up with a broken incentive scheme for putting our thoughts before actions.

If the situation arises that a failure does demand retrospection, I strongly recommend scoping the exact failure that is being addressed as narrowly as possible. I believe addressing failures from the most logically constrained perspectives possible is the most productive approach to developing postmortems that could prove useful in the future, while contextualizing failures by exaggerating their nature and the stories behind them leads to aporetic chaos, potentially even causing further failure.


The phrase “Go, Fight, Win” was something an old debate coach would tell my team shortly before we entered debate competitions against teams we had a particularly hard chance of beating. Regardless of the severity of our losses (of which there were many), or the gap in experience between other teams and ourselves, this phrase, simple as it may be, made crystal clear to us that we weren’t just at the tournament to gain experience— we were there to win. In forgetting about the possibility of failure, we better immersed ourselves in our efforts to succeed, and, when it counted most, doing so made all the difference. It focused our minds and placed our eyes on the prize—where they really belonged.

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