DHH has gone from not having a driving license at ~25 yrs old to winning his class in Le Mans at ~33 yrs old.
The important observation: While going up through the individual endurance competition tiers, do not wait till you start winning the current tier before advancing to the next one.
As the saying goes, if you are the best in the room, you are in the wrong room. There is little opportunity (and motivation) to continue learning and improving. And this goes further — I’d argue that the worse you are compared to your peers, the more opportunity (and motivation) there is to learn and improve yourself.
If your ego can handle it, there is little purpose in staying in the current game until you are the best before moving on. While staying in the current league gives you more money and satisfaction, it slows down your progress.
If you are an employee, don’t wait till you are the most senior one with the highest pay before you start freelancing or start a company (if that’s what you want). If you are on Toptal, Upwork or another marketplace as a solo freelancer, don’t wait till you are one of the top earners before starting an agency/company of your own.