20 Years’ Experience… or Just Year One on Repeat?

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At the weekend I was having dinner with a friend who I hadn’t seen in 20 years. We started updating each other on our careers and she was in the same role she was in 20 years ago. Sure, the title had changed a bit, but the content sounded the same.
It made me ask, did she have 20 years’ experience or 1 year repeated 20 times?

It’s a question that tends to land somewhere between uncomfortable and transformative.

We often equate tenure with expertise. Twenty years in a role must mean mastery, right? Not necessarily. Because experience, on its own, isn’t what drives growth, reflection, challenge, and adaptation do.

There’s a quiet trap many of us fall into: we get good at something, then we keep doing it… the same way… for years. No real stretch. No meaningful feedback loops. No deliberate evolution. Before we know it, we haven’t built 20 years of experience, we’ve built one year of experience, carefully repeated.

And organisations can unintentionally reinforce this.

Roles become routines.
Performance becomes consistency.
Learning becomes optional.

But the world doesn’t stand still and neither should we.

Research backs this up. The concept of deliberate practice, introduced by Ericsson et al. (1993), highlights that improvement depends not on repetition alone, but on purposeful effort, feedback, and continuous refinement. Simply doing something for longer doesn’t guarantee you’ll get better at it.

Similarly, Argyris and Schön (1978) distinguish between single-loop and double-loop learning. The former is about making small adjustments within existing frameworks. The latter challenges the assumptions behind what we do. Growth lives in that second loop, but it requires curiosity and, occasionally, discomfort.

Although incorrectly attributed to Einstein, the quote ‘doing something over and over again and expecting a different outcome is a sign of insanity’ really sums it up!

So, what does “20 years of real experience” actually look like?

It looks like:

• Seeking out feedback, especially when it’s inconvenient

• Letting go of “how we’ve always done it”

• Staying uncomfortably curious

• Regularly updating your mental models

• Being willing to be a beginner again

It’s less about time served, more about how you’ve used the time.

For leaders, this raises an even bigger question:
Are we rewarding experience… or evolution?

Because high-performing teams aren’t built on tenure alone. They’re built on people who are learning faster than the problems they’re trying to solve.

So perhaps the better question isn’t how long someone has done something
but how many times they’ve rethought, relearned, and reinvented how they do it.

References (Harvard style):

Argyris, C. and Schön, D.A. (1978) Organizational Learning: A Theory of Action Perspective. Reading, MA: Addison-Wesley.

Ericsson, K.A., Krampe, R.T. and Tesch-Römer, C. (1993) ‘The role of deliberate practice in the acquisition of expert performance’, Psychological Review, 100(3), pp. 363–406.

Gladwell, M. (2008) Outliers: The Story of Success. London: Penguin.

Page, S.E. (2007) The Difference: How the Power of Diversity Creates Better Groups, Firms, Schools, and Societies. Princeton, NJ: Princeton University Press.