When I left the investing world in 2014 to chase my dream of playing pro squash, I felt thrilled — and terrified — as I boarded a one-way flight to New Zealand. Leaving a set path to follow a passion felt like a solo pursuit. That feeling is what led me to write a book, When to Jump: If the Job You Have Isn’t The Life You Want – to help others going through that journey feel less alone.

Today, the decision to jump has become a movement – The Great Resignation – with many more people behind it. A record 48 million workers quit their jobs in 2021. And it doesn’t show signs of stopping: nearly half of workers today are seeking a new job.

The way we work is changing – and with it is how we think about our careers. If we’re fortunate enough to have employment options, the job we choose is increasingly impacted by the type of life we want.

Whether you’re making a massive career switch, changing jobs in the same industry, or going for a new role in the same org, the Jump Curve framework in my book shares four key insights to remember:

  • Listen to the little voice: If you hear an inner whisper that keeps telling you to take a risk in your career, listen to it. It’s usually right.
  • Make a plan: Once you decide to follow your gut, it’s time to get down to business – the budgeting, brainstorming, skill developing. Successful jumps aren’t spontaneous. 
  • Let yourself be lucky: Not even the best planning can remove all the risk. At some point, close the spreadsheets and journals and make your move. 
  • Don’t look back: No jump is a straight line, but you’ve put in the time to plan. This move might be crazy, but it’s not stupid. Embrace everything ahead and remember that the beauty of this journey will come from those “10,000 unsexy steps” along the way.

You may take one jump in your career. Or you may take several. There’s no formula.

My jumps away from structure have ultimately led me back to it – in a way that made sense for me. Today, I’m a for-profit impact investor focused on climate change and inclusive growth. I’m in a more formal workplace and able to do mission-aligned and entrepreneurial work. 

This opportunity was made possible by the sequence of events that unfolded after my very first jump toward chasing the pro squash dream. From there, I jumped to write my book and then launch a future-of-work startup, where I was invited to a startup summit hosted by my current co-workers. 

In this multi-jump journey, I realized something: A jump is not so much a one-time pivot, but a continual zig zag. Your jump may zig you one way, only to later zag you another, and it will continue in that way as your career evolves.

Knowing this, I wish I’d also asked myself a question when I took my jump: how do I make sure the zig I make with this jump sets me up for zags I may want in the future?

Here are three things to keep in mind on your zig zags ahead:

Stay in touch. Give friends, colleagues, and bosses the heads up of what you’re doing and where you’re off to, and then be sure to keep them updated regularly. You have no idea how they’ll come back into your work or your life, but the odds are, in some way, they will. A mentor of mine from my college internship – over ten years ago – ended up being the very person who recruited me to my current role. 

Keep learning. The way we work now will look vastly different in just a few years, and with this flux comes with it a constant array of new skills to master. Stay ahead of the curve by reaching out to experts and going deep in researching on topics that interest you

Accept that you’ll change. Your wants and needs today are different than they will be tomorrow. At twenty-five, my idea of a jump meant living out of a carry-on and sleeping on couches. Not today. Circumstances change. Things happen: spouses, kids, health –  all new variables that generate the need for new decisions which may change where you want to go. That’s okay. Give yourself permission to evolve. Your first jump is just that – your first one. Make it, and be open to what comes next.

You have no idea where your next jump will lead – and that’s the fun of it. Good luck on your zigs today and the zags they’ll create tomorrow. As you go along, reach out to me – I’m excited to see where you go.


  • Mike Lewis worked at Bain Capital before chasing his dream of playing professional squash around the world. That led to his book, When to Jump: If the Job You Have Isn't the Life You Want, a collection of case studies with clear guidance on how and when to jump toward a passion. Today Mike is a venture capital impact investor with a focus on climate transition and inclusive growth themes globally. He received his BA from Dartmouth College and MBA from Stanford University and lives in Santa Monica.