My PhD advisor once gave me the advice to use the “monkey bar technique”.
If you have achieved success in field X, and want to move into field Y, then you really don’t want to have to go back down to the bottom again and have to work your way up. Instead, a better approach is often to use your skills in field X to get a job that allows you to build expertise in field Y.
Sometimes you might need to take several steps to get where you want, where in each step you use your current skills to get a job that allows you to build new skills. This is similar to the way a child moving across the monkey bars holds onto one bar while reaching out for the next one.
In my case, I started out with a PhD in programming language implementation, which led to a job as a research scientist at Intel where I learned about the web, which led to a job as a software engineer at Google where I learned about product design, which led to a job as a product manager at Google and then Quora.
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