Life is not chess, it's poker. Gently putting your thumb on the scales is the best we can do.
Certainty is an illusion, only probabilities are real. So what you do isn't "Plan the next 10 years", it's "Make $goodOutcome a little more likely than $badOutcome", then adjust in real-time as the situation changes.
You can apply this to your career by having a career vision that helps you walk in a direction and lets you own your career.
You can apply this to your day-to-day work to make decisions faster.
You can use it to think about the hiring and interviewing probabilistically instead of feeling like you have no control, but also not beating yourself up, if things don't work every time. You're selling a high-end product after all, not every lead's going to convert :)
You could even use an expected value approach to deciding whether to work for startups or bigtech. And don't forget about your luck surface area – that really matters.
Avoid ruin and have fun with the rest.
Cheers,
~Swizec
PS: for a great in-depth book on this stuff, check out Thinking in Bets by Annie Duke. Taleb's works can be good for a more financial-focused look. Kahneman's works are great for a "Wow humans are fundamentally probabilistic" vibe

