Luck will matter more in the future

Imagine a cricket match between India and Ireland. The skill gap is so wide that even if Ireland wins the toss, India is still likely to win. The stronger team dominates, regardless of that small element of chance.

Now imagine a match between India and Australia. Two highly skilled, closely matched teams. In that case, the toss can actually impact the outcome. That one coin flip suddenly matters far more because everything else is nearly equal.

This is the “paradox of skill,” as discussed by Michael Mauboussin. As everyone’s abilities improve and the difference in skill shrinks, luck begins to matter more.

The same thing is happening across industries. AI is flattening talent curves. Everyone can now produce decent content, analyze data, write functional code, or design something that looks professional. The baseline has risen. Competence is no longer an advantage. It is expected. And in that environment, small edges or pure chance begin to play a much larger role.

So when I think about the future, I see increasing value placed on things that are hard to measure and even harder to teach. Taste. Creativity. Timing. Intuition. And yes, just dumb luck.

So, here are three obvious implications of that.

• The Rise of Signature Styles
  As AI raises the baseline for everyone, people are starting to care less about flawless but soulless content and more about the voice, perspective, and personality behind it. They want to connect with the human element. This makes individual style a key asset, especially when it comes to discretionary products or services where personal connection and trust matter most. Furthermore, with AI able to crank out passable content in seconds, including blog posts, slide decks, and even brand logos, the premium shifts to curation. Maybe even just having good taste goes a long way—whatever that is.

• Luck as a Strategic Variable
  If outcomes depend more and more on small variances, then “making your own luck” starts to become a real strategy. That means trying different things, exploring new spaces, and saying yes to experiments that have low downside but high optionality.

  But here’s the catch: that approach only really works in environments where failure is accepted, or at least where it doesn’t come with major consequences. That’s usually in more decentralized setups like startups, side projects, creative work, or small teams where people have more room to move. In top-down systems where everything has to be justified , and failure gets punished, people naturally play it safe. So optionality doesn’t just require the right mindset. It needs the right structure too.

• Survivorship Bias on Steroids
  When luck looms larger, the stories we see are often the tail ends of randomness. Celebrating only the winners without unpacking the role of chance warps our view of causality. As “how I made millions with AI” narratives increase, it’s ever more vital to ask: How many equally driven, equally skilled people tried and quietly failed?

That’s all for now. Thanks for reading