The Experience Myth

Experience is a double-edged sword. While experience can lead to greater expertise, this relationship is by no means guaranteed, and often hides stagnation, if not outright decline.

The true value of experience isn't measured in years, but in one's capacity for radical intellectual humility—the willingness to constantly challenge assumptions, embrace uncertainty, and prioritize learning over ego.

This doesn’t invalidate all experience, but is a reminder to evaluate talent through a more dynamic lens: by tangible results, demonstrable skills, and compelling evidence rather than accumulated tenure.

Here are 10 ideas on how experience can mislead:

1. 30 years of experience is often 1 year of experience repeated 30 times. Just because we show up doesn’t mean we get better. Think of your coworkers 30 to 40 years into their careers. Are they really at the top of their game or just hanging on? What was the last novel skill they learned? When was the last time they challenged a corporate tradition or volunteered to cross-train in a new area? What experience cohort is more often advocating for change and innovation?

It’s just like driving a car. We’re no better at driving at age 40 than we were at 30. Ten extra years of experience. Zero skill improvement.

2. Environments change, making past experience irrelevant. What was relevant and valuable in one era is now diminished, if not entirely negated. For example, coding and legal document review are two of many skills now in the crosshairs of AI, as new tools may obviate the need for human skill. Kodak and Blockbuster, once the world’s leaders in physical film and movies respectively, missed the transition to digital. Things change, and the best went bankrupt.

3. Experience is comforting. It’s a great feeling to be at the top after many decades of hard work. You’ve made it, and now feel you’ve earned some relaxation. Except you really can’t relax. The idea of always having this “beginner’s mindset” is uncomfortable for many. It feels great to be good, but to stay good, you have to go back to being bad by challenging yourself. It’s a continuous cycle of improvement.

“Complacency often afflicts precisely those who have been the most successful.” – Andy Grove

4. Experience rarely crosses boundaries. A great chess player isn’t more likely to be a good leader or programmer or investor. The expertise we gain in one field rarely transfers to unrelated fields. This is why doctors and dentists think they’re great investors but are not. Very good at their day job, but that’s where it stops. This also explains the failure of “brain training” programs. Yes, you get good at the brain training program itself, but not anything else.

5. Experience narrows our focus. Experience tunnels our vision and distorts our judgment as we selectively filter to fit our past experience. Partly due to overconfidence and the urge to feel like we have control, we forget that our personal experience is a tiny fraction of the history of this world. We’ve barely experienced anything, but our minds convince us we have complete knowledge. This is why we offer the same predictable solutions to emerging problems. They’ve worked in the past, so why not try them again?

6. Experience hardens our views. We overweight our experience and underweight data from controlled, independent studies and trials. Like idea #5, we believe our experience is somehow magical and special, and when we see evidence that conflicts with our beliefs, we throw out the data and keep the beliefs. Our ego keeps us as the center of the world. When there’s compelling data that conflicts with our views, we dismiss it.

7. Experience takes too long. If we rely just on personal experience, it would take centuries to synthesize the knowledge that could be learned by studying the lessons of what other people have figured out. There’s a lot that’s been learned. You can try to learn it all yourself, or learn from the lessons of others. Go with the latter.

8. Experience understates luck. Many investors believe their skill is the big reason for success, even though they’ve been investing in the U.S., where over the last few decades, outside of the Tech Bubble and 2009 Financial Crisis,  it’s been nothing but an up market. That’s an incredibly accommodating environment that has made it much, much easier to invest successfully. It has little to do with the investor and their experience.

9. Experienced people bend, if not break, the rules. After a certain level of experience, you believe rules are designed for less-gifted amateurs, rather than experienced professionals as yourself. This likely describes most hedge fund blow ups and disasters like the Challenger Space Shuttle. Experienced people selectively bend the rules, with a success rate no better than a coin flip.

In his book, The Logic of Failure, Dietrich Dorner explains the mindset of the Chernobyl reactor operators:

The great self-confidence of this team was doubtless a contributing factor in the accident. They were no longer operating the reactor analytically but rather intuitively. They thought they knew what they were dealing with, and they probably also thought themselves beyond the ridiculous safety rules devised for reactor operators, not for a team of experienced professionals.

10. Experience is bad at prediction. Experienced investors don’t know where the markets are going. Experienced politicians can’t pinpoint the next major political upheaval. Experienced meteorologists can’t predict the weather beyond a few days. Experience is better at preparing for the future, not predicting it.

Dee Hock, the founder of VISA, summarizes: “The problem is never how to get new, innovative thoughts into your mind, but how to get the old ones out.” It’s not experience that matters, but what you’re doing with it.