Are you taking enough risks?
I recently finished listening to an interesting episode on the "Farnam Street" podcast called Getting Better by Being Wrong. On there, Shane Parrish the host interviews a super insightful best-selling author and professional poker player Annie Duke.
I highly recommend listening patiently to the whole thing but you can skip through some parts if you like they don't relate to you much.
However my favorite takeaway was on the topic of learning.
Annie shares an insight into how even the world class professional poker players end up with the "bad beat" thinking mentality after a certain point. She says she was a bit immune to this thanks to being an outsider and some very candid mentors who would keep her honest. With this she was able to constantly revise her entire knowledge base and was willing to keep "risking" games so she could uncover new unique strategies. This paid great dividends in the long run.
Bad beat thinking is where the players start to blame things on luck and get off the hook. This is quite an easy cop out considering poker is naturally prone to a bit of luck. She argues that the "bad beat mindset" is where two people complain about how luck played a much larger role in their losses. This actually feels great in the moment but is probably worse for both of them since it limits your learning ability dramatically.
I found an astounding similarity in the startup space which I argue is just as uncertain and unpredictable like poker.
Founders tend to get highly selective and too narrow in their imagination once they hit some decent success and blame the rest on the market. Yes, market is the ultimate tail wind you need to succeed but you can't posit it as just pure luck. If you are willing to learn and pivot and persevere, eventually you will meet your market. The real thing however is whether you are still actively trying new uncomfortable things. Are you still just as stoked to take risks on a weekly/monthly basis?