Counterintuitive Truth: Luck Is Only Useful If You’re Ready for It
The paths to startup success are lined with stories of luck—sometimes eerily so. But what stands out, when you dig deep, is that opportunity only matters if you’re prepared to see and seize it. Behavioral economist Richard Wiseman famously studied luck, finding that 'lucky' people practice open-minded attention: they’re more likely to spot, write down, and act on unexpected opportunities than their 'unlucky' peers. At Excite, for example, funding and breakthroughs came through bizarre chains—accidental introductions, contracts born from random conversations, unlikely investors.
The founders of multiple legendary companies kept logs (sometimes mental, sometimes literal) of chance encounters—a lunch that led to a connection, a small meeting that went nowhere but sparked an idea. Rather than brush these moments aside, they leaned in gently, treating each as a test, not a make-or-break commitment. By experimenting and learning, even from apparent failures, they readied themselves for the moment when true luck arrived. Importantly, rare is the person or team for whom luck arrives if they’re not prepared; you can’t cash in good fortune if you never see it.
To start milking luck for all it’s worth, keep a visible record of new connections, chance offers, or wild-card opportunities that come your way. Don’t overcommit at first—treat each as a low-stakes experiment to see where it leads. No matter how it turns out, document what happened and what you learned. Invite your friends or team to do the same, and you’ll create a net that catches lucky breaks others miss. Try this habit for a month and notice the difference.
What You'll Achieve
You’ll expand your capacity to notice and capitalize on lucky breaks, increasing your access to life-changing opportunities and learning faster from every experience.
Set Up to Recognize and Leverage Lucky Breaks
Keep a visible log of opportunities—even small or uncertain ones.
Write down any chance meetings, unexpected invitations, or random connections, however minor. Review this list weekly.
Treat each opportunity as a mini-experiment, not a full commitment.
When something lucky (or weird) happens, ask, 'Could this be worth exploring?' If yes, give it limited time or resources to test its potential.
Learn from every opportunity—even the ones that flop.
After each experiment, briefly note what worked, what didn’t, and how you might adapt for next time. Encourage your team or friends to do the same.
Reflection Questions
- When was the last time you turned a random connection into a meaningful outcome?
- How can you better spot and test new opportunities in everyday life?
- What experience taught you the most, even though it didn’t work out as planned?
- Are you leaving space in your week for unplanned experiments?
Personalization Tips
- You run into a teacher at the grocery store who mentions a competition—consider entering, even if it's outside your wheelhouse.
- After being introduced to a neighbor with an open internship, you try it for a week before making a big decision.
- A friend tells you about a new club at school; you attend once and jot down your impressions.
Founders at Work: Stories of Startups' Early Days
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