Mike Lewis: Founder and CEO of When to Jump

  • Name: Mike Lewis
  • Job Title: Founder and CEO of When to Jump
  • Age: 28
  • Location: San Francisco, CA

Your website says: “When to Jump  is a community dedicated to exploring the fundamental question we all think about: when is the right time to go do what you really want to be doing?” Tell me about when you made the jump.

I grew up in a small city in California. My dad was interested in squash and by chance, when we moved into town, they had some of the only squash courts within 90 miles. I was 13 when I fell in love with sport, and like most kids, I dreamed of playing professionally one day. What is neat about squash is that it seems very random in the U.S. but it’s very popular and widespread throughout the rest of the world. There is a professional squash tour, and while it’s not very lucrative, it does allow you to compete all over the world. I made it a point that someday I would join the tour. I was fortunate to have the support to train, travel, and find the right players to compete against in order to play at the collegiate level. But by the time I graduated college, I wasn’t at the that professional level.

I had a great opportunity to work for an investment firm in Boston—like any kid graduating college, being employed was the first thing on my mind. A few months into working, I realized that if I didn’t try to play squash professionally soon that the window would close and probably never reopen. My day-to-day looked a lot like everyone else’s who works at a desk. I liked it. I was working with smart people. But there was a little voice in my head that I really wanted to follow, I just didn’t know how.

I talk about this in my upcoming book called When to Jump: If The Job You Have Isn’t the Life You Want. You can sign up to get updates on the book release here. I share what it was like to leave the corporate world and move to New Zealand to start the pro tour. From that moment on, I began what would be a pretty incredible journey.  

Mike And Map

Tell me about the pro tour and how the project really became a reality.

About a year before I left, I started to play on the tour part time. I would play on weekends or take a sick day here and there. The tour is a funny conundrum because you need pro points to get into the tournament but you don’t get into tournaments without points—you kind of need to start with a lucky break. I was lucky to find a few tournaments in the states where they let me in as the last spot.

The idea for When to Jump came when I was going through that experience and was looking for some sort of reinforcement that I wasn’t completely crazy. I would cold call people who, similar to the people on your website, had created a cool life for themselves specifically by making some sort of jump. I just kept asking them, “How did you know when to jump?”

I got in touch with a woman in January of 2013 who told me how she left her job on Wall Street to become a cyclist, and later made the Olympic team. Her advice wasn’t about how to become a cyclist, but rather about her fear of failure and other relatable issues that people find helpful regardless of what your jump is. I sketched a cover page for a book idea that night. I told my friend, Corey, who worked next to me that I would make it into a book someday.

For the next year and a half, he held me to it but I kept making excuses. While I was gone in August of 2014, Corey passed away in an accident. I stopped with the excuses. Over the next 10 months, I stayed with locals, other squash players, host families, friends of friends, and strangers while I continued to interview people. I called the project When to Jump after the cover page I had sketched a year and half earlier.

Mike Group Shot

How did this project develop into into a book deal, partnership with the Huffington Post, events in different cities, and various other mediums?

I really just wanted to see it through and didn’t stop myself from dreaming big. Instead of just writing a book or making a website, I wanted to make a platform that looks like TED with in-person events, an online community, a media partnership, and then books as well. It was kind of crazy since at the time I was backpacking around the world playing squash, but I put that idea out there and fortunately people responded.

When I came back I was introduced to people in the book world and had an incredible agent in New York take a chance on me. We made a proposal and received a few different opportunities for book deals. We met the people from Macmillan and it just felt like the perfect match. The book is coming out in January of 2018. You can sign up to get updates on the release via our newsletter.

Macmillan were the first ones to say, “Let’s make this part of your vision and anchor the When to Jump platform through a book.” Around the same time, in a series of really fortuitous events, I ended up meeting Arianna Huffington who initiated the idea of a partnership with the Huffington Post. In the span of a couple months, I went from crashing on my buddy’s couch to pitching stories and editing narratives to negotiating a media partnership, finalizing a video channel, and then launching a book deal.


Will the book mainly cover your story or multiple jump stories?  

Both. My story will be threaded throughout the book but we are also featuring dozens of stories from individuals of all different walks of life who each left something comfortable.

You mentioned the cyclist you interviewed struggled with the jump because of her fear of failure. Is that a common theme?  

Read the book to find out! But yes, one of the biggest reasons for not jumping is a fear of the unknown. You know what you’re giving up but you don’t know what you’re getting.

Some people may read this and think about how difficult it can be to jump when they have bills to pay, children to support, etc. What advice do you have for those people?

It’s less about big jumps. It’s about making any jumps that matter—a jump could be learning a new language, getting a second job on the weekend, or volunteering. There’s a lot of little things you can do to spice things up.

On the other hand, some people struggle with not knowing where to jump to. What advice do you have for people who haven’t figured out their passion?  

Find things that interest you and start taking steps to learn more about those things.

Scuba Mike

What’s the most inspiring jump story you’ve heard thus far?

The first female bishop in the Anglican church got to that position from a public relations job in a large corporation. But there are so many inspiring stories. I think there will be something that everyone relates to in the book because we feature people of all ages, ethnicities, genders, job types, income levels, etc. Like we talked about earlier, there are all sorts of different jumps you can make.

What’s next for you after the book?

Fulfilling the potential of When to Jump. I truly believe it can be just as big as TED one day.  I’d love to get there and if I don’t make it it, at least I can say I tried.

Anything else you’d like to add?

We are hosting our first Jump Club on October 9th in San Francisco. It is an in-person event that is part speaker series, part beers with friends, and part music festival.

Question from the last interviewee: Which part of your job have you found most difficult and why?

I think the most difficult part of my job is prioritizing all of the different opportunities because you don’t really know how to structure your day when you’ve been working for other people your entire life. It’s really hard to stay focused on the most important things when you don’t always know what they are.

What one question do you want to ask the next interviewee on People With Cool Jobs?

Is this what you grew up thinking you would do?

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