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​Welcome To A Community of Passionate Dream Chasers

Mike Lewis's story sounds like a typical one of this generation. Yearning for something more, he leaves Corporate America in the pursuit of his dreams, giving up the security of a regular paycheck to go travel the world for freedom, life experience and happiness. Except this is not a typical story. And Mike is no typical dreamer. In fact, Mike has been so passionate about finding his dream job that it led him to create an entire community of like minded individuals. One that has caught the attention of people like Arianna Huffington. We sat down with Mike to ask him how his unlikely story took him from the boardroom to the center of a movement that's much bigger than he ever thought possible.

DJ: Tell me about your background. What inspired you to start When to Jump?

ML: When to Jump evolved organically out of a passion of mine.

I wanted to wake up and feel like I was doing something that made an impact. Like many people I was doing a job I liked but I really wanted something more. The light bulb moment came out of my own struggle to find my path. The more people I spoke to the more I realized I wasn't the only one on this journey and I started collecting the stories of others who had also taken a risk to pursue a passion in some way. My friends encouraged me to keep going.

What I learned is that we all have something that we love to be doing. Whether that's going back to school or starting our own business - we have dreams and thoughts tucked into our head. While my experiences were unique to me, I believed that it shouldn't feel like I was going through it alone and the more I searched, I realized others didn't want to feel like that either.

At the time I was largely focused on playing professional squash. At some point, I said to myself “life is too short" and in figuring out when to chase this dream, a side project was born. It started on, and slowly grew from there.I got to a place where I felt like if I didn't jump then I never would, and it was the stories of others who helped me make that step. As time moved on, these stories have found a home and a supportive community growing around them. Today, you can sign up for these stories on

DJ: What do you consider a 'jump'?

ML: Jumps come in all shapes and sizes. It's not always about leaving your full-time job. A jump could be getting a promotion, changing careers entirely or pursuing a passion project. And there are lots of reasons to jump – it could be emotional, to support family, gain location independence or financial reasons.

DJ: What do you love most about When To Jump?

ML: It's not a place to tell you how to live your life or give you the 5 steps to find happiness. What I am the most proud of is that we have become the container for people to exchange the stories of their lives.

We are a community of people from all different walks of life. We stretch from Kenya to Australia to Spain. When to Jump is a place where people can express their jumps and share the good and the bad about what it really takes to make a jump into the unknown.

DJ: What advice do you give to people who know they want something more but they don't have any idea what to jump to?

ML: We have a lot of members who post photos and share stories about how they just followed the thread that made sense. Many people have a lot of interests. Elizabeth Gilbert says “follow your curiosity" and I believe that. You have to follow your curiosity and ask lots of questions. Pull a thread and then pull another one. If you like to travel, volunteer in a travel guide store. Put yourself in a place where people are like-minded. That's where you will see things that you can't plan for right now. You don't know what you don't know and you need to take baby steps to run into new opportunities.

DJ: Do any big challenges in your career come to mind that you turned into opportunity?

ML: A lot of people hear success stories and think that when they jump they'll get immediate gratification. And what you don't hear is the roller coaster that goes on emotionally. Our community brings out a collage of authenticity about what it takes to make that jump.

It's taken us a while, but we are now very fortunate to have the interest of big names like Arianna Huffington and the Huffington Post and the publisher Henry Holt & Co, of our soon to be released book. This will ensure our work gets out to a wider audience via college reading list, libraries and city cafes around the world.

DJ: What lessons are you hoping others take away from your work?

ML: I hope When to Jump makes people feel less alone in the experience and helps them feel part of a valuable, supportive community. Jumping from one thing to another may feel like an isolated process but what I've found is, that feeling is fundamental to being human. Before you jump you can't plan every single detail out and you'll never know all of the knowns. There's always a reason not to jump.

DJ: What's next for you?

ML: We have a book coming out in early 2018 featuring some of the best and most meaningful narratives and stories. We also have our very first in person event 'The Jump Club' running in San Francisco early October. We use our e-mail newsletter to keep everyone in our community up to date, so if you're interested to stay in the loop, subscribe at

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