I feel like what most people consider "risk" is more "fear of unfamiliar outcomes". To a gambler, a "risky" bet in a card game doesn't feel like it because both outcomes, winning and losing, are familiar. However that same gambler might not want to risk a smaller amount of money, even if the odds were better, in an unfamiliar situation.

So my advice is find safe ways to become familiar with the outcomes. Put yourself in situations where you will fail, or most likely will, but the stakes are low enough that it doesn't matter.

If you're worried about risking your time and energy on a side project, do a weekend version of it first. Find contests, hackathons, challenges that provide a scaled down, structured version of whatever you want to do and do those. Immerse yourself in the space (don't pretend to be an expert, just learn all you can), help people on related projects, and soon enough it won't feel risky anymore, you'll have a realistic intuition of the outcomes.

Also, beware of letting FOMO and envy motivate you. Those evaporate quickly.