Should you stop or work? What skills do you want to acquire? How do you estimate how much you will actually earn? If you're good at what you do, it turns out the only kind of risk is not taking a risk at all. This is my quick guide on how to think about the different opportunities that come your way. Learning early is more important, but winning is absolutely something you should focus on mid-career.

I'm Garry Tan, venture capitalist and founder of Initialized Capital. We were early investors in billion-dollar startups like Coinbase and Instacart. I'm creating my own individual YouTube channel, with no staff or team – I'm all about raw and unfiltered, which isn't perfect.

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