How an idea grew a community in 2016

I started this year living and working from a couch. I was trying to figure out how to move forward on an idea, and stuck on what to do. Fresh off an adventure that propelled me out of my corporate job, away from my comfort zone and around the world, I was now back at home – or actually, at Crosby, Charlie, Emily and Claire’s home – with an idea in mind. And a huge block of fear ahead of potentially chasing it. 

Ironically, my idea was to build a community – spread across digital media, in-person events, and a book – that would facilitate a safe place for chasing ideas. I had a name for it, When to Jump, but that was about it. I couldn’t help but laugh not knowing when to jump to start When to Jump.

Ideas – and the passion projects and dream pursuits that they inspire – are really scary. The only thing more terrifying of having an idea of something you want to do is the prospect of not doing something about it.

But what do you do next? On my friends’ couch during the first few months of 2016, the answer became clear.

While my friends were more than generous in giving me a sofa to crash on, it was something less obvious and far more important, that came along with the cushions: their unconditional support. The community I was looking to launch would come from this first makeshift one: a group of other people who shared with me their own fears and dreams, who supported mine, and who wanted to help see it forward. 

But more effective than any tactical advice or strategic planning was what came from the random conversations coming home from nights out, late night brainstorms after work, weekend morning chatter in the living room before Game of Thrones. No one would name it, or even define it, but between meals and before morning commutes, midnight snacks and on the way to the bar, there it was: honest, real support for my attempt to chase my idea.

Ultimately my jump was put in motion by people that extended far beyond my roommates – gym partners and former classmates, coffeehouse baristas and corner bartenders, the guy in my Uber and the girl at the grocery store checkout line. In addition to my couch hosts, these are just some of the heroes of my jump story – the ones who put up with endless questions, answered unnecessary follow up thoughts, stamped out any early seeds of doubt before they could sprout.

Read more: Experiencing adventure in 2016

As I left the couch and began my jump during the second half of 2016, I took from these friends, neighbors, and strangers far more than I gave in return.

As I look ahead for 2017, I want to give it back.

I was lucky – incredibly, incredibly lucky – to have bumped into this random, beautiful cast of characters who helped me start When to Jump over this past year. Most people aren’t so lucky. My goal is to change that with what we’re building.

For 2017, and years afterward, I hope to deliver a community and environment where the people, ideas, support are waiting for anyone looking to take an idea forward. My goal is offer a stage for anyone to get up to, stand on, and shout out a jump to make. And then connect with their version of couch hosts, bartenders and coffee baristas that are waiting to offer that same type of support.

It’s not going to happen overnight, but we’re slowly pulling it together. This time next year I’ll release a book, When to Jump: If The Job You Have Isn’t The Life You Want (join the newsletter if you’d like to get the word when it comes out). And a few weeks ago, in a keynote session with Airbnb, I got to test out our growing stage. In front of a few thousand strangers at Airbnb’s annual community festival, I ended my session with an ask to the audience: in a couple words, e-mail me your jump. Within minutes, I had over 500 e-mails of secret dreams, hidden ideas, tucked away and waiting to be told:

“Grad school and my business in food entrepreneurship.”

“Open boutique hotels around the world.”

“To live a life full of travel.”

“Write and act in my own web series.”

We all have an idea to chase and a jump to make. Next year, I will work to grow this stage support current and future jumpers everywhere. So after the holidays, come find me to get your jump started. I’ll be ready with stories, people, and ideas for you.

And, if needed, a couch.

This is a guest blog and may not represent the views of Please see for more details. Thumbnail from gettyimages.


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