It’s just about that time: the four year anniversary from that winter evening in 2014 when I told my boss I was making my jump.

With each year that has passed, I get a little more clarity on what was, at the time (and to some extent, still is) a surreal and game changing moment in my life. To paint the picture, I was in a job I enjoyed, newly promoted and on a path forward with the next milestone slowly appearing in plain sight. I had a boss I admired and respected. Yet, this month four years ago, I told him I was out. 

As I reflect on it, I still think it’s a crazy thing to jump. It’s never not crazy. And yet, I can’t imagine life taking any different route. Four years later, I center around what I call Four Big Things – the FBT - that helped me make a decision that would change my life forever. 

If you’re planning a jump, here’s the FBT you need to do.

Circle up a supporting cast. 

No jump is ever made alone, but more importantly, no jump is ever made by confiding only in one type of person – family, friend, coworker. You need a perfect blend. To get started, here are the first three ‘folks’ to circle up in your corner:

1.     “Switzerland” is someone who is a totally objective, neutral observer in your life. Unlike a parent or grandparent, Switzerland has no bias that may push you to stay on a safe path. Switzerland will tell it like it is. 

2.     “Nuts” is a doer, a maker, a fly-by-the-pants character who is way more, well, nuts, then you are. You plan for your jumps, Nuts doesn’t. Nuts is not someone you want to be like, but rather someone who reminds you that as crazy as you are, you’re not Nuts.  

3.     “Oops”  is the person who meant to jump but life got busy, and never went for it. Of all the supporting cast, Oops is the one who pushes you the most to jump – because the possibility of never trying is ultimately most terrifying.  

Make stuff, and lots of it

More than 18 months before I left my job in venture capital to play pro squash, I made a special folder on Dropbox. This would be where I would create, be messy, spitball, and make any and every piece of material that would relate to my jump. I committed to putting ANYTHING and EVERYTHING I could imagine about my jump to the pro tour inside this folder.

Travel ideas, fundraising slideshows, budget spreadsheets, lists of friends with couches to crash on–even mock cover page sketches and early draft interviews to what ultimately (five years later) became the When to Jump book, community, and global platform. On my phone walking back home or on a flight for work travel, I’d pull out this folder and build my jump. A lot of that material ended up not being relevant to my final plans to jump – but a lot of it proved critical. 

Months, and likely years, before you decide to jump, find a place to store your brainstorms, and get brainstorming. 

Plan one month

There’s a lot – maybe too much – material on social media pushing you to live your truth, take your jump…yada yada, blah blah, etc. etc. There’s not nearly enough messaging around what Day 1 of chasing your dream will look like – or Day 47, or Day 435. 

And while it’s overwhelming (and probably unproductive) to think out what exactly six months will look like, it will be helpful and even comforting to plan the first 30 days of chasing your dream: where will you be living? What specifically will you be doing with your time? Who will you need to see, where will you need to go? How much money will you need to save? 

In my book, the creator of the Humans of New York photography project, Brandon Stanton, reminds us that passion wears off after a couple weeks. The rest is hard work. Put pen to paper, plot out the first month, and you’ll be ready for the ride.

Measure the weight of regret

Draw a straight line down the middle of one sheet of paper. On the left side, fill in EVERYTHING going wrong with your jump. Flights missed, savings spent, customers lost – “failure” in the traditional sense, in every way. On the right side of the paper, write down the feeling of being 80 years old and not jumping. 

Take a piece of tape and paste this paper on your office cubicle wall, or under your computer screen. Somewhere that you’ll see it every day. 

The stuff on the left – everything going wrong in your jump – should scare you. And then, one day, when the stuff on the right – being 80 years old, and not trying for your passion – scares you more…it’s time to jump.


Need some inspiration to get started on your own jump? Take a look at Mike's When to Jump Roadmap and download your own blank template.

For ideas and support from more like-minded jumpers, visit

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