When to turn your side project into a full-time gig

Three founders share the trigger that finally made them take the leap

To celebrate National Small Business Week, we’ve put together a five-part series that delivers honest, helpful advice from successful entrepreneurs.

These days, it seems like everyone has a side gig that they dream of growing into a full-time career. But going from dream to reality can require a lot of faith, logistics, and money. After all, is there ever really a great time to say goodbye to the salary and benefits that come with your day job to launch an idea you hope will work? Three founders from WeWork Labs, a global community of early-stage startups that offers mentorship and education, say that no—there is no perfect time to leap. But once you do it, you’ll never look back. Here, they share what exactly gave them the push they needed.


Kirk Reynolds, founder and president, Discover Outdoors, a guide company for hiking, camping, and backpacking
Where: WeWork 154 Grand St, New York City
I worked on my side project for… about a year, managing the business early in the mornings, at night, and on weekends.
My full-time job was… selling enterprise software for IBM. It was great for professional development and learning about different industries. And being in sales, there was flexibility in my schedule that allowed me to develop my business on the side.
I knew it was time to take the leap when… I made a commitment to my mentor to do it by a certain date. There was never a moment where I felt secure and completely ready, so without making that commitment to someone else who would hold me accountable, I don’t know that I ever would have made the jump.
I prepared to go full-time by… doing my best to save as much money as I could. We also had a stream of revenue that was steadily growing. 
The best advice I’d give to those working on side gigs is… always bet on yourself. It’s a scary leap to make, and I’ll never try to minimize the weight of the decision. However, once you’ve made the leap and there’s no turning back, it’s amazing how resourceful you become. You’ll also find there are people who want to help you, so you won’t be alone. Also, don’t wait until you have everything perfectly planned. That day will never come. Accepting the reality that you don’t have to have it all figured out takes pressure off the decision. 


Yael Oppenheim, founder, FitMyTime, a marketplace that connects trainers and trainees from around the world for live online one-on-one fitness and yoga workouts
Where: WeWork Derech Ha’atzmaut 45, Haifa, Israel, where he’s also part of the global WeWork Labs community, which offers mentorship and education.
I worked on my side project for… about seven or eight months.
My full-time job was… doing market research as a freelancer. 
I knew it was time to take the leap when… I won second place at a pitch contest held at WeWork Haifa, which gave me six months of membership to the WeWork Labs program. That, in addition to the great feedback I received as a result of the competition, really encouraged me to put more time and effort into my project. The support of the members, mentors, and managers of WeWork Labs has had a tremendous effect on my motivation, productivity, and networking, all of which contributed heavily to my commitment and passion.
I prepared to go full-time by… doing a little freelancing here and there to make money.
The best advice I’d give to those working on side gigs is… to make your full-time job your side project. Most people say that you must be fully dedicated to your project in order to make it work. It is definitely possible to start without leaving your day job—however, the best solution, in my opinion, is to work part-time to sustain yourself for several months while developing your idea. I believe that doing different things in parallel can actually benefit the creative process, because when you engage with different realms, solving different problems, it often leads to a fresh perspective.


Eiko Nakazawa, founder, Dearest.io, an early-childhood education startup that offers educational, flexible childcare through small-group programs hosted in homes and communities
Where: WeWork 175 Varick St, New York, where she is also a WeWork Labs member.
I worked on my side project for… about four months. I conducted research and small-scaled tests before deciding to do this full-time. 
My full-time job was… at Sony, where I worked for more than 10 years—first at Sony headquarters in Tokyo, then in New York, where I worked on global digital marketing, education tech, and branding initiatives. 
I knew it was time to take the leap when… our first business idea was accepted into Columbia University’s Startup Lab—the opportunity gave me the push to make the move. 
I prepared to go full-time by… using my savings.
The best advice I’d give to those working on side gigs is… to talk to other founders with similar business models, as well as people in your industry and investors. If you are open about what you’re working on and are able to reach out to many people, you should be able to get relevant feedback and advice. Not only are these helpful for you to plan the next steps, but also useful for you to understand potential pitfalls and challenges.

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