Most Big Wins Are Hidden Behind a Pile of Failures
You don’t see every failed joke a comedian tells in clubs before refining their act for Netflix. You miss the pile of scripts a filmmaker abandons, or the dozens of products Amazon launches that barely register until finally—Prime or AWS emerges and changes the game. In finance, almost every index fund is packed with underperformers, but a handful of giants—Apple, Amazon—dwarf all the losses.
Researchers who study venture capital and big stock indexes often find the same pattern: about 40% of stocks or startups lose most of their value, but a slim 5-10% explode, covering all the losses and then some. Broad success comes not from near-perfect hit rates, but from letting enough tries ride so that a few 'long tails' can make all the difference. Yet it feels startling each time a loss comes, as if things aren’t working.
This truth is hidden in plain sight—most progress rides on a small fraction of spectacular outcomes, and surviving (mentally and practically) through rows of ordinary or even failed attempts is what gives you a chance to win. By normalizing failure and focusing on systems that keep you exposed to opportunity, you make luck more likely to arrive.
Look at your wins and trace back the stack of tries, setbacks, or rejections it took to get there. Every time a project falls flat or an application is ignored, remind yourself that this is simply the toll for playing a game that rewards those who stick it out. Start distributing your energy and resources more widely—make more attempts, try different approaches, let the odds of a 'long tail' work in your favor. Measure your growth by what works after the dust settles, not by each stinging loss in the moment.
What You'll Achieve
Reduce emotional pain from routine failures, become more resilient and patient, and structure your efforts so that rare, significant successes have a chance to pay off.
Anticipate Failure and Play the Long Game
Examine your track record for hidden successes and failures.
Pinpoint a few ‘hits’ in your life (projects, relationships, investments) and backtrack to see how many attempts or failures stood behind each one.
Reduce emotional overreaction to everyday losses.
Remind yourself that in any complex pursuit (careers, investing, creativity), about half your tries will fail. Accept that messiness as normal, not personal failure.
Set up routines or systems that maximize your exposure to potential 'tails'.
Invest time or resources broadly across opportunities; avoid putting all effort into only one or two bets. Track results by overall progress, not by each individual try.
Reflection Questions
- How many failures (big or small) sit behind my best breakthroughs?
- How can I set up my routines to maximize potential 'tail' wins?
- Do I judge myself harshly for losses that are actually normal?
- How does accepting randomness change my approach to setbacks?
Personalization Tips
- An artist submits to many contests, knowing only a handful might win awards, but that’s all it takes for recognition.
- A student applies to twenty internships, expecting most rejections but landing one key offer.
- A business launches multiple products, understanding that a few blockbusters will drive the growth.
The Psychology of Money
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