​Almost exactly two years ago, I sat across from Arianna Huffington and the rest of the HuffPost exec team in their polished NYC headquarters. We were discussing the opportunity to partner together: When to Jump and HuffPost. I was a few days into seriously considering my new “jump” – from the squash tour to starting the WTJ community – and as if the execs across the table could read my internal thought process, one asked, “So, is When to Jump a brand, or just an idea?”

I said of course we were a brand.

As soon as the meeting ended, I went about figuring out how to make a “brand”.

Turns out, it’s hard to make a brand and especially one anchored around a community. The past 18 months since I decided to jump into WTJ has been everything I anticipated it would be – full of failures, setbacks, surprises, big wins, huge losses, and above all, worthwhile.

​Together with my friends Daniel Jaffe (videographer guru) and Scott Korchinski (music maestro), I set out to capture the When to Jump story of the past 18 months in this video.

We feature a few jumpers who are contributors in the book – lawyer-turned-firefighter Brenda Berkman and banker-turned-fashion-entrepreneur Eric Wu – along with others – UN women’s rights advocate-turned-Netflix original TV series creator Vandana Snyder, pharmaceutical sales rep-turned-crossfit-gym-owner Maillard Howell – to bring the story to life.

I hope you like it, share it, and celebrate with us the first 18 months of When to Jump.

Mike

​I was sitting with my life in a roller bag at the airport gate in Boston, a few hours away from a one-way flight to New Zealand, where I’d turn up as a lowly ranked squash professional in need of a couch. As I waited, I thought of something I could do to commemorate wherever I would go next: I would spin my racquet in each new village, town, or city. In squash, like tennis, a racquet spin begins the match. That somehow felt fitting to do on my travels.

​I figured I’d do it once and then get over it. At most, maybe a half dozen spins would end up somewhere on my hard drive years later. A couple hundred racquet spins later, this video was made—and for four years later, I’m sharing it for the first time. If you like it, share it to those who have a jump to make—a racquet to spin for their own life dream.

Mike

I started this newsletter two years ago with a ton of ideas and very little else - besides about 12 subscribers, most (all?) of whom being my family members.

I imagined the newsletter to serve as the messenger of our small but mighty community – a microphone to a stage showcasing incredible people, ideas, messages and stories.

In a way, nothing has changed: I still have a ton of ideas. Most (all?) of my family members are still on the newsletter, and we’ve been lucky to see it grow tremendously since it was set up.

​Technically, this project started when I was 24. Only I didn’t know it then. What I did know was that I was at a crossroad.

I was sitting at my desk in Boston, thinking about my longtime dream: take a break from corporate America and play the professional squash tour. I wanted someone to tell me when to go, but no one was gonna say, "Mike, it's now July 1, time to go chase your dream, remember?" I could feel it slipping away.

Before letting that fear totally take over, I realized I couldn’t be the first and only person to be in this position. So I boiled it down to a simple question: should I stay the course in something comfortable, or take a risk to chase my passion? This seemed like a simple enough question. I wondered what others had done.
 
So I asked. I tracked down anyone who left something safe, whatever that was: a job in consulting or social work, in teaching or engineering. Through these conversations I began collecting stories, with the common thread being that each person left something comfortable to pursue a passion. I stumbled into people from all over: ex-bankers, electricians, scientists, journalists–people from all walks of life who left the safe inertia of their own circumstances to try and do what they really wanted to be doing. 

So I boiled it down to a simple question: should I stay the course in something comfortable, or take a risk to chase my passion?

After a while it became clear that this was interesting stuff. I was compelled to share. I began passing these stories along to friends and family, bus passengers and bartenders—others who were at their own crossroads. The stories caught on. They were helpful, and inspiring. I thought of a better way to get them out.

So that is what I am doing now. This project is about jumping. Sharing the amazing stories and ideas of those who have jumped into an unknown. Without them I wouldn’t have been encouraged to jump. These stories enriched my life and I hope they enrich yours too. 

Hope you enjoy the site, and if you have any questions or ideas for me, please reach out.
Mike