Here's the way I look at it. Once your 401k or other retirement savings are on track to give you a comfortable retirement, that's like an option -- you are effectively guaranteed a minimum lifestyle. Within this bucket, you should certainly be balancing the expected value and risk "by the book" (diversifying, etc.).

How do you increase the value of an option? Increase the volatility. Continuing to minimize risk is not going to meaningfully change your lifestyle. Your call option already protects you on the downside, so you should try to blow it out on the upside, and take a risk.

You can also view your experience and skills (and the minimum salary it allows you to command in the market) as the same thing. After a certain point, try for something that will meaningfully change your lifestyle. Worst case, you can fall back to that floor salary.