Iterations over time will always win

2025-08-04

Let me illustrate this idea with a quick thought experiment. Take two people with equal ability at any particular skill (e.g. painting, programming, etc.). Both individuals are instructed to spend 1 hour per day working on the same skill. Person 1 is instructed to start a new painting every day, whereas person 2 is told to start a new painting every two weeks.

After two weeks, person 1 has produced 14 terrible paintings, and person 2 has produced 1 painting. I think it's safe to assume that you can't improve much within two weeks, and so the painting of person 2 will definitely be better than the best of the 14 paintings that person 1 produced, as they were able to spend 14 times longer working on it.

However, stretching this out to a period of 1 year, person 1 will have now produced 365 paintings, and person 2 only 26. Now, you bring in an independent judge to pick the best painting. Over this timeframe, it would be hard not to believe that person 1's best painting would beat the pants off person 2's. Despite both people working on this skill for the same amount of time, the person who iterated faster won.

If I have convinced you of that, then we conclude that it's not the amount of time spent working on a skill that matters, but the number of times we iterate, fail and start over.
Successful startups iterate and pivot. "Move fast and break things" is a common mantra.

Itterating is hard for perfectionists. The reality is that you will have to learn to be comfortable with being uncomfortable to iterate at a high frequency. One of my goals with writing these articles each day is to develop the ability to iterate quickly - to stop being a perfectionist, and say, "good enough", and move on.

© 2025 Sam Affleck. All rights reserved.

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