This past month, I did something I never thought I’d do—I hired people. From the very beginning, I always saw myself building Cushion as a solo developer, riding into the sunset with a small, sustainable app. I romanticized growing Cushion to the point where I could live off its income alone. Once I reached that goal, I would retire to a cabin upstate and simply maintain it for years to come.

That all sounds lovely, but it’s far from reality. Growing an app is incredibly hard—especially when you’re also the designer, developer, and support person. Aside from the daunting task of making an app profitable, loneliness starts to creep in after years of trudging in the same direction. Whereas I once dreamed of running Cushion by myself, I now dream about collaborating with a small team.

Recently, this dream has begun to take shape. Late last year, I started brainstorming with freelance writer Carly Ayres on where to take Cushion from a content perspective. Ever since, we’ve been working toward a goal of supporting the freelancer community and providing truly useful content—not the same listicles that have overtaken every other app’s blog.


Last week, we launched the first interview in our new series, Talking Shop, where we talk to freelancers about freelancing. Like building an app on your own, freelancing can be incredibly lonely, too. Most freelancers don’t work in a co-working space or big city where other experienced freelancers are within arm’s reach. Talking Shop is our attempt to bring the conversation to those who are eager to learn more about the freelance world from those who live in it.


Alongside Carly, I hired freelance illustrator Ping Zhu to illustrate each person we interview. I see illustration as a primary area where Cushion can embrace the freelancer community even further. Each piece of content we publish should be paired with its own illustration that lends itself to the writing. The content is then a collaboration between several freelancers and credited as such.


In February, I hired freelance developer Larry Fox to help with the actual app. We’ve worked really well together in the past, so I reached out immediately when he decided to go full-time with freelancing. In his first month alone, working only a few days a week, Larry and I were able to launch OverbookingAvailability, and the Availability Badge. Needless to say, Larry has been essential to taking Cushion where I want it to go.

If I didn’t hire the help I so desperately needed these past few months, I would probably be stuck on a single feature, spinning my wheels, and only imagining the things I want to do with Cushion. Instead, I’m leading a team of freelancers, building features at a lightning pace, and publishing new content on a schedule. I’m not alone anymore, and I think I prefer it this way.