Mike Lewis (Ep.29): The unsexy steps to chasing your dreams

Mike Lewis (Ep.29): The unsexy steps to chasing your dreams




At age 22, Mike Lewis had his dream job as a young venture capitalist at Bain Capital Ventures, moving up the ranks all while having fun and learning. But there was a little nagging voice reminding him of a dream – to play squash on the pro tour, even if it meant couch surfing and eating into his savings to do so. Mike did it, peaked at 112 and went on to write When to Jump: If the job you have isn’t the life you want. We’re bombarded by sexy stories about people who made the jump, but this obfuscates the planning, safety nets, and ways in which you can practice your own “jump.”And once you jump, there’s the guilt and the uncertainty BUT – it’s also when the element of luck starts to find you.

Mike Lewis and the When to Jump Community

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Show Highlights

The Jeff Bezos quote

When you are 80 years old, and in a quiet moment of reflection narrating for only yourself the most personal version of your life story, the telling that will be most compact and meaningful will be the series of choices you have made. In the end, we are our choices.

Just start

It can be tantalizing and compelling and far too easy to get into the mode of talking about a jump. It’s very sexy cocktail conversation, but unfortunately that’s not going to get you there.

What if you’re too busy?

I don’t think anyone is too busy, to overtired to take teeny little steps towards planning their jumps. And that’s what I think people tend to miss.

The three steps before pursuing your dream job

  1. Financial planning
  2. Safety net selling
  3. Pre-jump practice



Being honest about one’s desire to jump

One of the nights before leaving, I had one of these thoughts: my parents put forth this life for me, my siblings supported me. If I’m going to do this, I really need to see this through and that I’m not jumping for the wrong reasons. It’s easy to not jump because of the social status, income, and prestige — but it’s also sexy to jump for all those same reasons. The introspection for me was: “Am I doing this for the right reasons?”

Is chasing your dream job dangerous advice?

But I believe that in life, you’re either taking a jump or preparing for your next jump. That doesn’t mean you shouldn’t stop listening to the little voice.

Khe Hy
[email protected]

Khe Hy is the creator of RadReads.