Mike Lewis on Planning for Your Big Jump

This episode is sponsored by Gusto.

Afraid to make the jump into something exciting but unknown? Learn tips for how to do it from Mike Lewis, the founder of global community When to Jump and author of When to Jump. Mike’s path into the unknown was different than most: He left a lucrative career at a venture capital firm to become a professional squash player, or as Mike puts it “chase this obscure racket sport somewhere in Fiji.” In this enlightening interview, Lewis tells SUCCESS magazine’s Josh Ellis his own story of making the decision to leap into the unknown, and shares how to perfect your transition and what to do if it doesn’t work out.

This interview appears in the January 2018 issue of SUCCESS magazine.

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  • If you Google, “When is the right time to make the leap?” you might see a lot of aspirational content about what it’s like on the other side of that decision, Mike says. “Things look really nice and pretty, [but] glosses over onto the other side of making the leap.” 
  • When is it time to make the leap? To paraphrase When to Jump author Mike Lewis, when you’ll be satisfied with the outcome, good or bad, because the journey was absolutely worth it.
  • When you begin doubting whether you should make your next big move, try channeling your fear of missing out. “However scary it would be becoming a pro squash player and hurting my knee, it wouldn’t be as terrifying as never going,” Mike says.
  • By interviewing entrepreneurs, Mike saw four phases emerge in their journeys:
    • Listen to the little voice
    • Make a plan
    • Let yourself be lucky
    • Don’t look back

Favorite quote from this episode:

“If you get comfortable knowing that regardless of the outcome you’re gonna be satisfied because the journey is worth it, then I think that’s the time to jump.”  — Mike Lewis

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SUCCESS Talks, the popular audio program included every month in SUCCESS magazine, is now available as a weekly podcast. We feature fascinating interviews with prominent business, creative and thought leaders such as Tony Robbins, Richard Branson, Tim Ferriss and Barbara Corcoran, and include key takeaways designed to help you put information into action.

Catch up on all individual episodes at SUCCESS.com/SUCCESSTalks or download the monthly SUCCESS Talks Collection with your magazine subscription.


Josh Ellis is the former editor in chief for SUCCESS magazine. Before joining SUCCESS in 2012, he was an accomplished digital and print sportswriter, working for the Dallas Cowboys Star magazine, the team’s gameday program, and DallasCowboys.com. Originally from Longview, Texas, he began writing for his hometown newspaper at 16.

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