Out-Fail Everyone Else Why Embracing Experimentation Is the Real Success Secret
Success stories often skip the mountain of failed attempts that lead up to a breakthrough—but inside Amazon, Booking.com, and other fast-moving organizations, out-failing the competition is the holy grail. These companies set up cultures where experiments are small, rapid, and frequent, and where failed attempts are recognized as stepping stones, not scars.
Contrast that with slow, process-heavy businesses that get stuck waiting for certainty or consensus—often, by the time they move, the window has closed. The secret: there’s rarely such thing as a truly right answer in advance; the best way to find what works is to run as many tests as possible, fail cheaply, and learn quickly. Safe, reversible choices should be made fast, with accountability sitting at the point of action, not up some distant chain of command.
It’s not just for companies—individuals who try more, fail more, and reflect more gain skills and confidence exponentially faster. In a world that rewards adaptation, your failure rate isn’t something to be ashamed of; it’s your best metric for future success.
Pick a part of your work or personal life where the stakes aren’t catastrophic, and brainstorm three quick-fire experiments you could launch this week—small tweaks, new approaches, or fresh routines. Run them without waiting for perfect approval or endless discussion. After each, write down what happened and, crucially, what you learned, even if the outcome was a flop. Share the results and learnings openly with your group or boss, emphasizing the speed and honesty of trying over just getting it perfect. By making fast, tiny failures the norm, you’re sharpening your edge—and building the knowledge base no one else can match.
What You'll Achieve
Leapfrog the competition by optimizing for learning speed rather than only safe wins—achieve agility, more resilient confidence, and sharper instincts in work and life. Internally, gain comfort with risk and imperfection; externally, get to the right answer (and better results) faster.
Raise Your Failure Rate to Learn What Works
List low-stakes experiments you can try.
Think about areas in your work, studies, or personal life where you can test a new method, technique, or approach without severe consequences for failure.
Document both your failures and your learnings.
For each experiment, write down the outcome and what you discovered—even (especially) if it didn’t work.
Share and celebrate fast, honest attempts.
Publicize rapid experiments within your team, class, or group, rewarding those who execute and iterate quickly instead of only those who 'succeed.'
Remove excessive sign-off and bureaucracy for reversible decisions.
Push for systems where most choices (unless truly irreversible) can be made by small teams or individuals, so learning is fast and opportunity is seized.
Reflection Questions
- What reversible decisions am I overthinking when I could just try and learn?
- How can I make failure safe and even celebrated on my team or in my projects?
- What did my last big failure teach me about the next opportunity?
- How can I better document and share lessons from failed attempts?
Personalization Tips
- In a startup or side project, test new product features with a small user group, then pivot quickly.
- As a teacher or coach, encourage students to run 'fail-fast' science experiments or creative drafts.
- Within friendships or partnerships, try different routines to see what strengthens the bond, openly learning from what doesn’t stick.
The Diary of a CEO: The 33 Laws of Business and Life
Ready to Take Action?
Get the Mentorist app and turn insights like these into daily habits.