Welcome to “When to Jump”

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 around the world. 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: what have others done, when faced with staying the course in something comfortable, or taking a risk to chase their passion? This seemed like a simple enough question.

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.

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. As of today, www.whentojump.com is live. You can sign up for stories in your inbox here. You can read long form narratives on this When to Jump Medium publication, view photos on our Instagram account (@whentojump), and get quick updates from our Facebook page and Twitter handle (@whentojump).

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

This project is dedicated to my friend and former coworker, Corey Griffin, who inspired my journey and this project. For more information on Corey and his legacy, please visit the Corey C. Griffin Foundation’s website.