... No.
You want to learn skills that will increase your job security, make you happier, and advance your career. All that is true.
You might end up taking financial risks that seem heavy. $100 for an out-of-print book on a topic that you're really interested in. $750 (including airfare and hotel) to go to a conference. A couple hundred dollars of computing resources to try something out. Go for it. Those small financial risks are minuscule if they're making your life and prospects better.
That's different from risking your whole career.
"Career" is just a make-nice word for "reputation" (plus the time series of money infusions) and you don't want to take risks with that. Play a conservative game, because people are assholes and will take advantage of you as soon as there's a weakness in your story.
The tough part of all this is that it's hard to know where the worst career risks are. For example, academia is presented as a low-risk track for smart people, but the truth is that the long-term career risks are severe, even if unexpected job loss is extremely uncommon. (Finance, on the other hand, has more job volatility but much less existential career risk.)