Asher's Blog

There is an irony at the heart of achievement: winners often lose more than losers.

One of my mentors once expressed it in financial terms. He said that billionaires have lost more money than many ordinary people will ever make. A billionaire may have lost billions through investments, companies, market cycles and decisions that did not work, while someone else may have lost only thousands or millions. His point was not that losing money automatically makes anyone wealthy, or that every loss is admirable. His point was that people who operate at a significant level usually expose themselves to more attempts, more decisions and more risk. Their victories become larger, but so do some of their losses.

That thought stayed with me, and I eventually reduced it to a simple sentence: winners lose more than losers.

It sounds contradictory until you understand that there are at least two ways to avoid losing. You can become exceptionally good at what you do, or you can refuse to play. Many people who appear to have a clean record have simply attempted very little. They have protected themselves from rejection, embarrassment and failure, but they have also protected themselves from the opportunities that arrive only through participation.

If you plan to win a lot, you must accept that you will sometimes lose a lot. The important question is not whether you will experience failure. It is whether your failures are teaching you, strengthening your judgment and moving you closer to the result you want.

The people who win are usually the people still playing

Every meaningful pursuit produces unsuccessful attempts. If you are looking for a good job, you may submit many applications and receive many rejections. If you are building a business, you may approach customers who say no, test features nobody uses, hire people who do not work out and explore partnerships that lead nowhere. If you are raising capital, you may speak to dozens of investors before one believes in the opportunity. If you are building a relationship, developing a skill or pursuing an ambitious project, you will make decisions that look sensible but produce disappointing results.

The person who makes one application and stops after the first rejection may record fewer losses than the person who makes fifty applications. But the second person is far more likely to find a job. The first person has a better rejection ratio; the second person has a better chance of changing their life.

This is why the raw number of failures can be misleading. Ten rejections may mean that somebody is struggling, but they may also mean that the person has the courage to remain in motion. A person with no rejection may be extraordinarily competent, or they may simply have asked for nothing.

Winners accumulate evidence. They enter the market, receive an answer, study it and return with a better attempt. What appears to be repeated failure from the outside may actually be an active learning process.

Failure is not automatically useful

We need to add context, because slogans about failure can become dangerous. Losing money carelessly is not a qualification for becoming a billionaire. Repeating the same error without reflection is not perseverance. Ignoring evidence is not courage. Taking a risk that could destroy your health, family, company or obligations is not necessarily bold; it may simply be irresponsible.

Harvard Business School professor Amy Edmondson offers a helpful distinction in Right Kind of Wrong. She separates basic failures, complex failures and intelligent failures. In her words, “An intelligent failure is an undesired result in new territory.” It occurs when we pursue a meaningful opportunity in an area where the answer is not already known, use the knowledge available to us, keep the experiment proportionate, and learn something that can guide the next attempt.

That is very different from failing a familiar process because we refused to prepare, ignored a checklist or repeated a known mistake.

The mature ambition is therefore not to fail as frequently or spectacularly as possible. It is to increase the number of intelligent attempts while reducing preventable mistakes. We should be willing to pay tuition for learning, but we should not keep paying for the same class.

A useful failure should leave you with at least one of four things: better information, better judgment, better capability or a better relationship with reality. If it leaves you with none of those, you have not yet extracted its value.

Rejection is evidence that you are trying

Imagine that you have been searching for work for several months. Your inbox contains one decline after another. At first, each response feels like a verdict on your ability. Eventually, the repetition can begin to sound like a conclusion: perhaps you are not good enough; perhaps it will never happen; perhaps everybody else has an advantage you do not have.

But a rejection is not always a judgment of your entire value. It is a decision made by one organization, for one role, at one moment, based on a limited set of information and competing candidates. You should examine the message for whatever it can teach you, but you should not turn it into an identity.

If you are learning deliberately, your fiftieth application should not be identical to your first. Your CV should become clearer. Your understanding of the market should become sharper. Your examples should become more relevant. Your interview answers should become more concise and convincing. You should learn which roles fit your strengths, which skills employers repeatedly request and which relationships can help you enter the right rooms.

By the time the right opportunity arrives, you may discover that the journey prepared you for it. The rejections forced you to articulate your value; the interviews taught you how employers think. The disappointments expanded your resilience. What once looked like a collection of failed applications becomes the training ground behind a testimony.

That testimony may later become a map for somebody else. They listen to your story, apply the lessons you learned painfully and reach their own opportunity faster. Your loss has now produced value beyond you.

The football lesson: more progress creates more exposure

Football makes this principle easy to see. The deeper a club advances in competitions, the more important matches it must play. More matches create more opportunities to win, but they also create more opportunities to lose—and the losses become more painful as the stakes rise.

Liverpool experienced this under Jürgen Klopp. In May 2018, the club reached the UEFA Champions League final and lost 3–1 to Real Madrid in Kyiv. It was a painful night. Yet Liverpool returned to the final the following season and defeated Tottenham Hotspur 2–0 in Madrid on 1 June 2019.

The 2018 defeat did not guarantee the 2019 victory. Sport does not offer that kind of contract; but the experience mattered. The team had travelled through the competition, felt the pressure of a final and discovered what that level demanded. They did not allow the pain of reaching the summit and losing to persuade them that the climb was pointless.

The club could only suffer a Champions League final defeat because it was good enough to reach a Champions League final. Teams eliminated earlier did not experience that particular heartbreak, but they also did not stand one match away from the trophy.

This is what happens as your ambition grows. You become eligible for a more consequential class of disappointment. A small company may lose a small customer; a large company can lose a contract worth billions. A junior employee may make a mistake within a narrow assignment; a chief executive may make a decision that affects thousands of people. Greater influence increases both opportunity and exposure.

The goal is not to become afraid of that exposure. It is to build the character, systems and relationships required to carry it.

The size of the loss is not the source of the wealth

The statement that billionaires have lost billions needs to be understood properly. They are not billionaires simply because they lost billions. The causal relationship works differently.

They were able to take part in opportunities of enormous scale. Some of those opportunities succeeded and created substantial value; others failed and produced substantial losses. Their wealth may reflect ownership, leverage, access, timing, skill, luck, persistence and market conditions. Large losses are often a consequence of playing at scale, not a magical ingredient that creates wealth.

This distinction matters because people sometimes romanticize risk after seeing only the winner’s final outcome. They hear that an entrepreneur invested everything, borrowed heavily or survived several collapses, and they conclude that recklessness is the price of greatness. They overlook the person’s knowledge, network, safeguards, ability to recover, or the many people who took similar risks and did not succeed.

The lesson is not “lose more money.” The lesson is make more thoughtful attempts, and develop the capacity to survive the attempts that do not work.

That means limiting the downside where possible. Test an idea before committing all your capital. Validate customer demand before building every feature. Put agreements in writing. Understand your legal and financial obligations. Avoid risking money you cannot responsibly lose. Preserve enough runway—financially, emotionally and spiritually—to make another good decision. Winners do not merely tolerate loss; they manage it.

Turn every loss into an asset

After a disappointment, it is tempting either to blame yourself completely or to blame everybody else. Neither response produces much learning. The better approach is to separate facts from emotions without denying either one.

Ask:

1. What exactly did I expect to happen?
2. What actually happened?
3. Which assumptions proved wrong?
4. What was within my control?
5. What warning signs did I miss or ignore?
6. What should I repeat because it worked?
7. What must change before I try again?

Write the answers while the experience is still fresh. A loss that remains only as pain can become fear. A loss converted into principles can become judgment.

This is particularly important in business. When an initiative fails, conduct a proper review without turning it into a search for someone to humiliate. If people fear punishment for reporting bad news, the organization will hide the information it needs to improve. At the same time, psychological safety should never mean the absence of standards or accountability. People must be free to speak honestly, and they must also be responsible for preparation, execution and learning. The strongest teams create room for intelligent experimentation while making negligence expensive.

Do not confuse quitting with changing strategy

“Do not quit” is useful advice, but it is incomplete. Sometimes persistence means continuing the same mission through a better method. Sometimes wisdom requires ending a project, leaving a harmful situation or accepting that a particular strategy has failed.

You can remain committed to the destination while changing the vehicle. A job seeker may need to stop sending generic applications and begin building relationships in a narrower industry. A founder may need to abandon a feature while preserving the company’s larger purpose. An investor may need to exit an asset whose original thesis is no longer true. A leader may need to remove somebody they like from a role the person cannot perform.

Quitting because you are tired of learning is different from stopping because the evidence has changed. One is surrender to discomfort; the other may be disciplined adaptation.

Before you stop, ask whether you have tried enough intelligent alternatives. Have you obtained feedback from people who understand the problem? Have you changed the variables that produced the first result? Have you allowed enough time for the new approach to work? Can you explain, using evidence, why continuing is less responsible than stopping?

Persistence should not make you rigid. The objective is to remain faithful to the purpose while becoming increasingly honest about the method.

Protect your identity from the result

One of the most damaging things we do is convert an event into an identity. We move from “I lost” to “I am a loser.” We move from “the application was rejected” to “I am unwanted.” We move from “the business failed” to “I am a failure.”

Those statements are not equivalent; an outcome contains information about an attempt. It does not contain the total truth about a person. You may have made a poor decision; you may need to develop your competence. You may have been unprepared. You may also have done many things correctly and encountered conditions you could not control. Honest reflection requires enough humility to accept responsibility and enough perspective to refuse self-destruction.

Carol Dweck’s work in Mindset is helpful here. A fixed mindset treats ability as a final verdict: failure reveals what you permanently are. A growth mindset treats ability as something that can be developed: failure shows what you have not mastered yet. This does not mean everybody can achieve every dream merely by trying. It means the present result is evidence for learning, not permission to pronounce a permanent sentence over your life.

Scripture gives the same posture in Proverbs 24:16: “For a just man falls seven times, and rises up again.” The distinction is not that the righteous person never falls. It is that falling does not become their final position.

Measure attempts, learning and recovery

If you measure yourself only by immediate wins, you will avoid valuable work whose outcome is uncertain. A better scoreboard includes the behaviours that make success more likely.

For a job search, track targeted applications, useful conversations, interview conversion, feedback received and skills improved. For sales, track qualified outreach, meetings, proposals, objections and the reasons deals are lost. For product development, track assumptions tested, customer behaviour, time and money spent, and what each experiment taught the team.

The purpose is not to celebrate activity for its own sake. A hundred careless applications are not necessarily better than ten excellent ones. The purpose is to distinguish a weak outcome from a weak process and then improve the right thing.

You should also measure recovery. How quickly can you return to clear thinking after a loss? How quickly can your team surface the truth, protect customers, correct the mistake and try again? Resilience is not the absence of pain. It is the capacity to process pain without allowing it to determine every decision that follows.

Winners do not fear the record

When people see a winner, they usually see the victories that remained visible. They see the company that worked, the job that was secured, the trophy that was lifted or the investment that multiplied. They do not always see the rejected proposals, abandoned drafts, wrong assumptions, lost finals, difficult conversations and private moments when quitting seemed reasonable.

Success edits the story after the event. It makes the journey look more inevitable than it was.

Do not let another person’s polished result make you ashamed of your unfinished process. Your present rejection may be one attempt in a much larger story. Your responsibility is to learn, adjust and remain available for the next opportunity.

So, if you are receiving no after no, do not immediately conclude that you are a loser. Ask whether the no is teaching you anything. Improve the application. Strengthen the skill. Change the approach. Seek honest feedback. Return wiser.

If you are building a company and something fails, face the brutal facts. Protect the business from a fatal loss, but do not become so afraid of failure that the company stops experimenting. The organization that never makes an intelligent mistake may not be innovating at all.

If you have suffered a painful setback, give yourself permission to feel it, but do not build a home inside it. A lost match is not the end of the tournament unless you refuse to play again.

Winners do not win because every attempt succeeds. They win because they make enough intelligent attempts, survive enough disappointments, learn faster than they repeat mistakes, and refuse to let an unsuccessful result become their identity.

Winners lose more than losers because winners keep entering the arena. And, eventually, they learn how to win there.

References and further reading

• Amy C. Edmondson, Right Kind of Wrong: The Science of Failing Well. See also the Harvard Business School overview and its explanation of basic, complex and intelligent failure.
• Carol S. Dweck, Mindset: The New Psychology of Success.
• John C. Maxwell, Failing Forward: Turning Mistakes into Stepping Stones for Success.
• UEFA, 2018 Champions League final highlights: Real Madrid 3–1 Liverpool.
• UEFA, Liverpool’s 2019 Champions League final victory over Tottenham.
• Proverbs 24:16.