Rebooting Reboot Workshop
Five years ago I stepped forward to ask a question: How do you build a career that supports the life you want?
To find the answer, I co-founded an unconference called Reboot Workshop. I had just formed my own WordPress company and decided to go freelance to live outside the 9 to 5.
For Reboot, I wanted to create a space for anyone looking for career freedom a way to pursue their passion. A space where anyone can answer and ask questions. I knew I needed help starting my own business, and I knew I had somethings to offer others. So I opened the doors to start the conversation. My business partner, Jim and I brought in a panel of experts to talk about their areas of expertise: Accounting, writing, social enterprise, life/work balance, law.
We got together as a group four or five times over 2011–2014. Sometimes in a networking setting, sometimes as an unconference, sometimes as a panel event. The main thread was there. If you want to build a business, step up and ask questions. It was a great time for it too. With coworking just getting off the ground, with hackathon culture spreading like wildfire, with the start of web training bootcamps it was a time of asking and answering. For each of these things the question being asked was fairly straightforward: “Can these things really make any money?” (Short answer: Yes)
The idea of these things being profitable seemed like a joke when I got started and yet — whether you are aware of it or not — each of these three ground-breaking formats have grown overnight into billion dollar industries. For someone looking to get into startups, or technology, or freelance the opportunities are there like never before. But as these industries grew up something was lost.
I spent the last four years teaching classes at General Assembly, arguably one of the most successful coding bootcamps. I travelled around the world with StartupBus — one of the craziest hackathons. I moved from coworking space to coworking space until New Work City, New York’s first coworking community closed their business, lost in a fray of spaces offering “community” (and only some delivering). Every month I see students and eager participants coming through programs onto New York’s tech startup scene asking the same questions “How do we build a career that makes us happy?”
In a way, that question gets harder to answer every year because while the opportunities exist, the road to success is hard to navigate and becomes more challenging in a crowded space. The gravity of the New York Tech scene has shifted. Ever since New Work City closed, there’s been a real lack of center to it all. There is no common ground for people from different disciplines to meet and talk. There’s still the New York Tech Meetup. Coding bootcamps are bigger than ever, coworking is a worldwide phenomenon, but what’s next? Where can people who are just getting a start (or who are still thinking about their options) go to ask the questions? How do you get started and how do you keep sharp?
For many the real question on the table now is: “How do you build a community around innovation?”
I’ve heard this question asked by Universities, Museums, Fortune 500 companies, Startups, Nonprofits. Too often the answer seems cheap and empty. It’s easy to get seduced by the startup life if you’re not in it. You walk into a coworking space and you see ping pong and a beer tap and go “Is this really what work can be?” For anyone in the space, the challenges hidden beneath the surface become apparent quickly, but only when you ask the right questions. In 2016 there’s a real desire, a hunger now for doing something real, something you care about. People want to feel like they’re part of something bigger.
My colleagues and I talk about it in the little touches. When you walk into a place and the words roll off their tongue “community” and for those of us paying attention it can sometimes be an empty word. Is community really just a bunch of people together in a room? It wasn’t five years ago. Right now, 99% of all businesses in New York are small businesses. Yet where is the small business and freelance community that came up around coworking five years ago? Where do freelance web developers (or writers, or designers, or artists) go when they’re looking for clients? How do these people (people like myself) save themselves from burnout and create a sustainable life for themselves?
The truth is the community exists. The answers are out there.
is a better time than ever to start your own business.
is a better time than ever to learn a new skill.
is a better time than ever to ask the right questions.
Five years ago I asked the question: “How do you build a career that supports the life you want?”
I found the answer but I have a question for you.
What do you have to offer?
Reboot Workshop is a day-long unconference. Come expecting to learn, share, and ask questions.