Friday morning, October 25th. Watching another startup founder give a TED talk about how their three failed companies taught them everything, carefully omitting that investors lost millions while they 'learned' on other people's money.

The Failure Gospel

"Fail fast. Fail often. Failure is the best teacher. You haven't failed, you've just found 10,000 ways that don't work. Every failure is a learning opportunity. The only real failure is not trying."

Silicon Valley turned failure into a virtue. Now every industry has adopted the same narrative. Failure isn't just acceptable—it's celebrated. It's proof you're taking risks, pushing boundaries, learning and growing.

The people who succeed, we're told, are the ones who failed the most. They embraced failure. They didn't fear it. They treated each setback as a stepping stone to eventual success.

This narrative is mostly bullshit.

Thesis: The celebration of failure is primarily a post-hoc rationalization that lets people excuse poor planning, inadequate preparation, and strategic incompetence as bold experimentation. Most failure isn't valuable learning—it's predictable consequences of doing things badly. And the people who succeed usually do so by avoiding failure, not by learning from it.

What the Failure Narrative Obscures

The failure-as-learning story is compelling because it makes everyone feel better about their mistakes. But it obscures several important truths:

1. Most Failure Is Preventable

The romanticization of failure treats all setbacks as inevitable parts of the learning process. This is false. Most failures aren't mysterious unknowns that could only be discovered through experience. They're predictable consequences of doing obviously wrong things.

The startup that failed because they built a product nobody wanted didn't need to fail to learn this. They could have talked to potential customers before building. They could have tested demand before investing resources. They could have looked at the dozens of similar products that already failed for the same reason.

Their failure wasn't valuable learning—it was the predictable result of not doing basic validation work. They failed because they skipped steps that would have revealed the problem before committing resources.

The product launch that flopped because of poor timing didn't need to fail to teach that timing matters. Every analysis of previous launches in that market would have shown that timing matters. Every conversation with people in the space would have mentioned it. Every piece of conventional wisdom emphasized it.

The failure didn't teach them something new. It taught them something they could have learned by paying attention to existing knowledge instead of assuming they were special enough to ignore it.

The project that collapsed because the team dynamics were terrible didn't need to collapse to reveal that team dynamics matter. There are libraries of material on team formation and dynamics. There are assessments, processes, and frameworks for building effective teams. There are experts who specialize in nothing but this problem.

The project failed not because team dynamics are mysterious and unknowable, but because the leaders didn't bother learning what was already known or didn't care enough to apply it.

In each case, the failure narrative lets people frame preventable mistakes as valuable learning experiences. But learning something through failure that you could have learned without failing isn't valuable—it's inefficient and often expensive.

2. Failure Is Often Expensive for Others

The most enthusiastic proponents of learning through failure are usually people whose failures were expensive primarily for others, not themselves.

The founder who "learned so much" from their failed startup often learned on investor money. The investors lost their capital. The employees lost their jobs and equity. The founder got learning experiences and material for their next pitch.

The executive who "grew so much" from their failed strategic initiative learned while workers were laid off. The company lost market position. Shareholders lost value. The executive moved to their next role with "valuable experience leading through challenging transitions."

The consultant who "developed expertise" through trial and error did so while clients paid them to experiment. The clients absorbed the cost of the failures. The consultant built their resume.

When failure is expensive primarily for you, you're much more careful about avoiding it. When failure is expensive primarily for others, you can afford to romanticize it as learning.

The failure-as-learning narrative is often promoted most loudly by people who are positioned to capture the upside of success while others absorb the downside of failure. For them, failure really is just learning. For everyone else, it's loss.

3. Success Usually Comes from Avoiding Failure

The narrative says that successful people fail repeatedly before succeeding. This frames success as the result of learning from failure.

But look more carefully at actually successful people and organizations, and a different pattern emerges: they succeed primarily by being very, very good at avoiding failure.

The successful entrepreneur didn't try 100 random ideas and learn from 99 failures. They did extensive research, validated demand carefully, started small, tested constantly, and iterated based on feedback before scaling. They avoided most potential failures by being systematic and careful.

When they did encounter setbacks, these were usually small, controlled failures that revealed specific information without destroying the entire venture. They didn't embrace failure—they minimized it ruthlessly while learning as much as possible from each setback.

The successful product team didn't launch 50 failed products to learn what works. They studied existing successes and failures in their space, talked extensively with users, prototyped and tested relentlessly, and only launched when they had strong evidence of product-market fit.

Their success came not from learning through failure but from learning through research, testing, and careful validation—learning methods that don't require expensive failures.

The successful organization didn't survive because it learned from catastrophic mistakes. It survived because it had systems, processes, and cultures designed to catch and correct problems before they became catastrophes. It succeeded through competent execution, not through dramatic failure-and-recovery cycles.

Yes, successful people and organizations encounter setbacks. But the setbacks are usually small, controlled, and quickly corrected. The defining characteristic isn't that they fail and learn—it's that they avoid most failures through preparation, and handle unavoidable setbacks efficiently.

4. The Best Learning Doesn't Require Your Own Failure

The failure narrative implies that experience is the only reliable teacher. You can't really learn something until you've failed at it yourself.

This is obviously false.

You can learn from other people's failures. Every failure that's happened to others is a learning opportunity for you—if you pay attention. Reading about failed startups teaches you without losing investor money. Studying failed products teaches you without wasting development time. Analyzing failed strategies teaches you without sacrificing market position.

The people who learn efficiently learn primarily from others' failures, not their own. They read extensively, study case histories, seek advice from people who've been through similar situations, and apply lessons that others paid to learn.

You can learn from theory and research. Many important insights are available from academic research, professional frameworks, and theoretical understanding. You don't need to personally discover that humans have limited attention spans—psychology already figured that out. You don't need to personally learn that certain team structures work better than others—organizational research already mapped this.

Learning from existing knowledge is far more efficient than learning from personal failure. The fact that it feels less dramatic and doesn't make for good TED talks doesn't make it less effective.

You can learn from low-stakes experimentation. When you do need direct experience, you don't need expensive failures to get it. You can run small experiments, build prototypes, test assumptions at low cost, and gather information without betting the farm.

Good experimenters fail frequently at small scale. They're not celebrating failure—they're using controlled testing to gather information cheaply. The goal isn't to fail, it's to learn efficiently. When failure is the information source, they make sure the failures are small enough to be survivable.

The Failure Theater Problem

The celebration of failure has created a perverse dynamic where people pursue failure for its own sake, treating it as credibility or experience rather than as costly setback.

Founders who wear their failed startups as badges of honor, emphasizing how many companies they've tried rather than focusing on whether they learned to avoid repeating mistakes. The number of failures becomes the credential, not the quality of lessons learned.

Professionals who treat every mistake as a learning experience that they're eager to share, framing incompetence as growth mindset. They didn't miss the deadline because they were disorganized—they learned valuable lessons about project management. They didn't alienate the team because they were a bad manager—they grew through receiving difficult feedback.

Organizations that celebrate "learning from failure" while making the same mistakes repeatedly. They hold blameless postmortems and talk about psychological safety, but never actually implement changes that would prevent similar failures. The ritual of learning-from-failure becomes a substitute for actually learning.

The failure theater is all the rhetoric of learning from failure without any actual improvement. It's failure celebration that serves primarily to make people feel better about their mistakes rather than to prevent future mistakes.

What Actually Works Better Than Failure

If learning from failure isn't the path to success, what is?

Learn from Others' Failures First

Before making any significant decision, find out who else has tried similar things and what happened. Read their post-mortems. Study their mistakes. Learn from failures that are already paid for.

This doesn't mean copying success blindly. Context matters, and what worked for others might not work for you. But understanding what failed for others and why is almost always valuable information.

The best entrepreneurs aren't the ones with the most failed startups—they're the ones who studied hundreds of failed startups and avoided making the same mistakes. The best strategists aren't the ones who tried everything and failed—they're the ones who learned from others' strategic failures and made better choices.

Test Assumptions at Low Cost

When you do need direct experience, get it at the smallest viable scale. Don't bet everything on untested assumptions. Test crucial assumptions with prototypes, pilots, experiments that cost orders of magnitude less than full implementation.

This is different from "failing fast." Failing fast often means launching quickly with minimal validation, failing, and learning from the failure. Testing assumptions means finding ways to get the information you need without expensive failures.

The goal isn't to fail quickly—it's to learn quickly. Sometimes that involves small failures, but often it involves careful testing that avoids failure entirely.

Build Systems That Prevent Failure

Instead of celebrating learning from failure, build systems that catch problems before they become expensive failures.

Code review catches bugs before they reach production. Preflight checklists prevent plane crashes. Financial controls prevent fraud. Quality assurance processes prevent defective products from reaching customers.

These systems are unglamorous. They don't make for exciting failure-to-success narratives. But they're how reliable organizations actually work—by preventing most failures rather than learning from them.

The best organizations don't have the most dramatic comeback stories. They have boring, systematic competence that prevents most problems before they occur.

Develop Judgment Through Study

Much of what looks like learning from experience is actually developing judgment—the ability to predict outcomes, recognize patterns, and make good decisions in uncertain situations.

But judgment doesn't require personal failure. It requires exposure to many situations and outcomes—which can come from studying others' experiences as effectively as from your own.

The executive with good judgment didn't necessarily make every mistake themselves. They studied decisions and outcomes across many organizations, learned to recognize patterns, and developed intuitions about what works.

The engineer with good judgment didn't necessarily create every type of bug themselves. They reviewed others' code, studied system failures, learned about common failure modes, and developed instincts for what's likely to work.

The investor with good judgment didn't necessarily lose money on every type of bad investment themselves. They studied investment outcomes systematically, learned to recognize warning signs, and developed heuristics for evaluation.

In each case, judgment developed through systematic learning rather than personal failure. They learned primarily from observation and analysis, using their own small failures only to calibrate and test their developing understanding.

When Failure Actually Teaches

This doesn't mean failure never teaches valuable lessons. Sometimes it does. But valuable learning from failure has specific characteristics:

The failure revealed genuinely new information. Not information that was already available if you'd looked, but information that wasn't knowable without trying. True uncertainties, not ignored certainties.

The failure cost was proportional to the learning value. Small failures that teach specific, actionable lessons are valuable. Catastrophic failures that teach general lessons you could have learned more cheaply are not.

The lesson was actually learned and applied. If you make the same mistake twice, you didn't learn from the first failure—you just failed twice.

The failure was on your critical path to success. Some failures are necessary because there's no other way to test the crucial assumption. Most failures aren't on the critical path—they're predictable consequences of skipping preparation steps.

Most celebrated failures don't meet these criteria. They're expensive lessons in things that were already known, or failures that taught nothing that led to subsequent success, or repeated failures where nothing was actually learned.

The Quiet Competence Alternative

Here's what the alternative to the failure narrative looks like:

Study extensively before acting. Read everything relevant. Talk to people who've tried similar things. Understand what worked and what didn't, and why. Learn from knowledge that already exists rather than insisting on learning through your own experience.

Test carefully when moving into uncertainty. When you do need direct experience, get it at the smallest scale possible. Run controlled experiments. Build prototypes. Test assumptions systematically. Learn from small, controlled setbacks rather than expensive failures.

Build systems that prevent predictable failures. Don't celebrate learning from mistakes you could have prevented. Build processes, checklists, review systems, and safeguards that catch problems before they become expensive failures.

Learn from your own small failures, but mostly from others' large ones. When you do encounter setbacks, extract specific, actionable lessons. But recognize that your most valuable learning comes from failures that others paid for and you studied.

Develop judgment through analysis, not through trial-and-error. Study outcomes systematically. Build mental models. Develop pattern recognition. Use small personal experiments to calibrate and test your developing judgment, not as your primary learning method.

This is much less dramatic than the failure narrative. It doesn't make for inspiring TED talks. It's quiet, systematic competence rather than dramatic failure-to-success stories.

But it's what actually works. The people and organizations that succeed reliably don't do so by embracing failure and learning from it. They succeed by being very, very good at avoiding failure through preparation, systematic learning, and careful execution.

The Friday Reality

The failure celebration is primarily a rationalization. It makes people feel better about their mistakes by reframing them as learning experiences. It makes dramatic failure-to-success stories more compelling. It gives people permission to be less careful and less prepared by framing failure as inevitable and valuable.

But most failure isn't valuable learning. It's predictable consequences of skipping preparation, ignoring existing knowledge, or not testing assumptions carefully. The lesson was already available—you just didn't learn it until you paid for it through failure.

The most successful people don't succeed by learning from failure. They succeed by learning extensively before acting, testing carefully at small scale, building systems that prevent failure, and developing judgment through systematic study rather than expensive trial-and-error.

When they do fail, the failures are usually small, controlled, and quickly corrected. They don't celebrate the failures—they learn the specific lesson and move on. The failures aren't the point. Learning is the point, and failure is just one (expensive) learning method among many.

Stop celebrating failure. Start celebrating learning. These aren't the same thing. You can learn without failing, and you can fail without learning. The goal isn't to fail fast or fail often. The goal is to learn efficiently—which usually means learning from others' failures and your own careful experiments, not from your own expensive mistakes.

Stop treating failure as inevitable or necessary. Most failures are preventable. The people who fail repeatedly aren't necessarily learning more—they're often just repeating mistakes while calling it experimentation.

Start treating failure as costly signal that you didn't prepare adequately. Not something to celebrate, but something to analyze, learn from once, and avoid repeating. A small failure that teaches a specific lesson is valuable. A catastrophic failure that teaches a general lesson you could have learned more cheaply is waste, not learning.

The uncomfortable truth: The failure narrative is popular because it makes people feel better about their mistakes and gives them permission to be less rigorous in their preparation. But success comes from competent execution, not from learning through failure.

Study extensively. Test carefully. Build systems that prevent failure. Learn primarily from others' expensive mistakes rather than making your own. Develop judgment through analysis and observation more than through personal trial-and-error.

This is less dramatic. It won't make for inspiring conference talks. But it works better.

Stop failing fast. Start learning efficiently. The people who succeed aren't the ones who failed the most—they're the ones who avoided most failures while learning everything they needed to know.


The failure fetish: We celebrate failure as learning—'fail fast,' 'embrace failure,' 'failure is path to success.' But this romanticization is mostly excuse for poor planning and strategic incompetence masquerading as bold experimentation. Thesis: celebration of failure is post-hoc rationalization letting people excuse poor planning, inadequate preparation, strategic incompetence as bold experimentation. Most failure isn't valuable learning—it's predictable consequences of doing things badly. People who succeed do so by avoiding failure, not learning from it. What narrative obscures: (1) Most failure is preventable—predictable consequences of not doing basic validation work, ignoring existing knowledge, skipping obvious steps; (2) Failure is expensive for others—founder learns on investor money, executive learns while workers laid off, consultant learns while clients pay for experiments; (3) Success comes from avoiding failure—successful people/orgs succeed by being very good at avoiding failure through systematic preparation, careful validation, controlled testing; (4) Best learning doesn't require your own failure—can learn from others' failures, from theory/research, from low-stakes experimentation. Failure theater: pursuing failure for its own sake, treating failed startups as badges, framing incompetence as growth mindset, celebrating learning-from-failure without actual improvement. What works better: learn from others' failures first, test assumptions at low cost (goal is learn quickly not fail quickly), build systems that prevent failure, develop judgment through study not trial-and-error. When failure teaches: revealed genuinely new information, cost proportional to learning value, lesson actually learned and applied, on critical path to success. Most celebrated failures don't meet these criteria. Quiet competence alternative: study extensively before acting, test carefully when moving into uncertainty, build systems preventing predictable failures, learn from own small failures but mostly from others' large ones, develop judgment through analysis not trial-and-error. Most successful people don't succeed by learning from failure—they succeed by learning extensively before acting, testing carefully at small scale, building systems preventing failure, developing judgment through systematic study. Stop celebrating failure, start celebrating learning. These aren't same thing. Failure narrative popular because makes people feel better about mistakes and gives permission to be less rigorous. Success comes from competent execution, not from learning through failure.

Today's Sketch

Oct 25, 2025