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.
Each year I get a little more clarity on what was (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, four weeks after the launch of the When to Jump book, 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.
It's felt like one long, crazy dream.
That's probably the best way to describe the first two weeks on the road: the five cities, two countries, 17+ events, and hundreds of people I've been lucky enough to meet on the book tour so far. It's felt like one long, crazy dream.
And the best part has been the people. When the cities and talks and signings fade away into a blended blur, what will stand out will be conversations like one with a couple in Boston last Tuesday after the event at Harpoon Brewery, who drove in to share with me their jump: starting a non-profit in honor of their son who passed from pediatric cancer. Or the young woman in Washington, DC, who shared with me after the event at the Smithsonian that she feels she no longer needs permission from her mom to jump and live life on her terms—a welcomed perspective toward a tough and harmful relationship that marked her childhood.
8 days ago the book launched, over 3 years ago I left my desk to play squash, and 2 years before that I started thinking about taking a jump that would change my life.
In a different parallel somewhere else in the same universe, Laura McKowen was living a life different than mine - a single mom a few years older than me - yet going through similar motions, wondering how to act on a dream that seemed both crazy and maybe doable.
Laura reached out to me after hearing my interview with Rob Bell in March of 2016. It was the day after she gave notice to her job, and set forth on her passion for writing.
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.
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.
When I planned to play pro squash, my biggest fear would be that I’d be lonely, sitting in a vacant motel room watching days pass. So I made an itinerary that would give me the first few weeks on couches with friends of friends. After that, I figured I would have to deal with being on my own.
That didn’t happen.
A few weeks on couches turned into nearly two years on more couches and under mosquito nets, on mountain tops and basement bunk beds, crashing with friends, friends of friends, and strangers while stepping into peoples’ lives right as they’re being played out
Today is the day.
Not a whole lot to say other than THIS IS TOTALLY SURREAL!!! You can waltz into bookstores across the country and in most countries around the world, or online wherever books are sold. You can scribble down your jump and post it on our community jump wall. You can spread the word in 3 ways and in under 30 seconds.
But most of all, I hope you enjoy it.
I hope it leads to something positive in your life. I hope it gives a source of permission to try something new - big or small. I hope it serves as a gift to someone you care about, someone who is ready to jump and needs that nudge. IT WILL BE THAT NUDGE!! :)
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.
When To Jump
What If the Job You Have Isn't the Life You Want?