Embrace the awkward

and other lessons from a crash course in entrepreneurship.

Make $1000 online. Get featured in a blog. Send a cold email to a stranger and arrange a coffee meeting. These are just a few of the assignments I was given this semester in Entrepreneurial Design, a course taught by Gary Chou, Christina Xu and Leland Rechis as part of the MFA Interaction Design program at SVA.

I entered the course with a healthy skepticism. Wasn’t entrepreneurship just something you had or didn’t have? Having worked in tech before grad school, there was always a kind of mystique around startup founders. To have such command, to execute on an idea so effectively, to raise so much funding must require some kind of unspoken “it” factor. I wasn’t sure I had whatever “it” was.

I quickly discovered that the class wasn’t designed to teach so much as instigate discomfort. You can’t really learn entrepreneurship without doing it for yourself, so this was going to require me to put an idea out in the public. Whatever I produced would be tied to my name. If I failed, my failure would be for everyone to see, forever traceable in Google searches.

I braced myself for a semester of suspended awkwardness.


Treat it like an experiment

When I share anything on the internet, my natural impulse is to curate it carefully. But things were different over the 16-week period of the course, and I found myself having to become a little more flagrant with my online presence. Sometimes that meant candidly asking for retweets or beseeching Facebook friends to sign up for a newsletter. Sometimes it meant listening to crickets chirp as I sent out dozens of cold emails.

It was emotionally trying, this work. I felt a palpable sensation of sinking in my stomach every time I hit Send. Then I’d wait in agony until the smallest affirmation would arrive in the way of a Like, and my spirits would rise through the roof.

At some point I tried to manage the roller coaster with a more neutral perspective. It helped to think of every interaction as an experiment. In an experiment, you can have a hunch, investigate it objectively, and analyze the outcome. There isn’t a concept of a right result or a wrong result. There is just the result, and it leads to some knowledge that helps set up the next experiment.


Launch before you’re ready

When you’re asked to drop everything and make $1000 on the internet, it raises lots of questions. Namely: How the hell will you do this? Then: What can you make that’s worth sharing with other people? And: Where can you add value in the world?

In times like these, deep reflection can quickly turn to endless rumination. That’s when constraints help. I had a pressing deadline. The pressure was on. I remembered something. Before we’d parted for winter break, a classmate and I had laughed about how much fun it would be to make a children’s book together someday. I wasn’t really sure how this would make either of us $1000 in the course of one semester, but I suggested we go for it.

If there’s any secret sauce to entrepreneurship, if there’s any “it” factor, it’s this: start before you feel ready. Avoid the perpetual stalemate of having preconceptions around what is and isn’t possible.

In the beginner’s mind there are many possibilities, but in the expert’s mind there are few. —Shunryu Suzuki

We knew nothing about printing or self-publishing, and it was unrealistic to think we could complete the book in such a short period of time as total beginners. We second-guessed ourselves: Should we scope down, maybe sell t-shirts instead? Sites like Custom Ink and Teespring made on-demand t-shirt designing and crowdfunding a breeze. But the book made us happy, and the fact that we didn’t feel ready was the point. A complete, polished product isn’t necessary for validating an idea. We could pull together a concept, propose it to the world, and see what the world had to say. We could build from there.


Embrace the awkward

The act of making is deeply personal. For some people it’s quasi spiritual— we make with the intention of learning things. We then construct meaning out of what we learn in the process, which allows us to take an incremental step in our larger understanding of the world.

We decided to run with our book idea, our passion project. It doesn’t get much more personal than that. The challenge then became mentally managing how personally attached we were to our idea and our dreams for it. You are not your work, Gary advised in many class sessions. Success and failure are things just that happen.

Allow me to flash forward to the end of the story, after the Kickstarter campaign we launched for our children’s book was a success. In this moment, happiness and sunshine abound. We are more than fully funded and look forward to continuing our work on the most delightful side project imaginable. In this moment, Gary’s advice is music to my ears. It’s the wisdom of a sage.

But in an alternate history, the campaign could have totally flopped. Would a detached point-of-view like this be possible then? Would I regret having put myself out there in the world? The nice-sounding answer: Not a lick! After all, I’d have learned something! The true answer: I don’t know. Human emotions are awkward. I might have regretted putting myself out there.

Sometimes we invest all of ourselves in something and it inevitably becomes personal, and then we crash and burn, and it all happens because we’re human. Sometimes we can’t help but identify with our work.

Before we launched our project, Gary had also told us: At this point, your biggest risk is inaction. I hadn’t thought of it this way before. We’re constantly making unconscious choices about the ideas that inspire us, aren’t we? We implicitly make a call: take action or don’t. Action is hard. It gobbles up time and energy. It has the potential to end in a soul-crushing kind of way. But when the risk of inaction is just as real? That’s when embracing the awkward, readying up for the potential skinned knee, and seeing what happens might just be worth it. ■


Shout out to Tess Russell and Adelle McElveen for their input.