Is the best path to specializing and high compensation specializing in a certain field or skillset? I am relatively late in my career and do not have much to lean on in regard to expertise and freaking out around long term job security

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It is in the short run. In the long run, depends on how in demand your skillset is and how many people can do it (incl. any regulatory restrictions). It’s one reason neurology/anesthesiology pays so well in medicine.

Generally people who apply broad skills earn more (CEO vs the specialists who report to them, for example). Have a read of the book “Range” - it might might cheer you up. Good luck

Honestly it depends what your desired range is. The skills to get you from 200-500 are way different than the 1 million plus skills. People who are highly specialized and unique skills tend to have an overall cap on career earnings but that cap is good enough for the overwhelming majority of us.

In a sort of non answer to your question the most lucrative career path for someone who’s hyper specialized in one skill is probably playing a popular sport that isn’t hard on your body like basketball, baseball or soccer and having a long playing career at an elite level and then moving into being an amazing coach. If you’re at that level you can probably earn like, 20-30 million a year during you playing career for 15-20 years and then coach another 2 decades for career earnings around 500 million.

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