Take many small risks.

And safeguard two resources you have.

Time and money.

So, instead of working on a big project every year, which I am a big proponent of, work on  4 projects – 1 big and three small.

Your 1 big project should come out of your smaller projects after it has shown promise and downside is low.

Once you have this clear, decide what big win means for you.

Is it a lot of money?

A ton of free time?

Happiness?

This does not have to be either or situation. You can achieve two outcomes at the same time. Still one of those has to be a priority.

Once you have figured it out, optimize for that outcome.

If happiness is the outcome you want, think about what makes you happy and pursue projects that allow you to do that.

If lots of free time is your goal then build your projects around a lifestyle where you can pursue your projects without investing a lot of time.

Don’t choose anything that takes a lot of time. If your project is a business, then choose one where you make something once and sell again and again, like a product, book, or software.

Hope you’ll give it a shot.