Emotional Entrepreneurship

After 7 years of official startup founder status, I still struggle with what it means to be one. That is to say, I still feel sometimes like I’m in high school and wearing my mom’s suit for a job interview, squinting in the mirror at my new reflection and wondering how many minutes it will take my prospective boss to figure out that I’m wearing a borrowed suit. Let it be known, I have been working for nearly 20 years, so this is ridiculous. The rational part of my brain is aware this is ridiculous. The whole point of being a founder is to take on risk and do new things, so of course it will feel uncomfortable. And I’m hardly the first person, especially woman, in the world to describe impostor syndrome.

And yet.

The whole point of the job is also to be confident in the face of a tsunami of new things. So even in the most authentic and trusting of entrepreneur circles, I have been reluctant to talk about the challenges. Because dwelling on the tsunami did not seem to be a viable startup growth strategy. So often, I sacrificed my need to talk and air the challenges for the sake of momentum and shine. And with time, it gets easier and easier. Seasoned entrepreneurs speak starry-eyed about their first pitch, first hire, their first acquisition, how little we had and how little we knew. The hardship becomes part of the lore, but the humanity is often left out of the story. That dissonance often sat, fermenting, deep in my belly.

Here’s the thing, though. If we want to encourage a diversity of founders and social entrepreneurs, build an inclusive society, and encourage new types of ventures to take big risks to solve climate and equity challenges of the day, we need to normalize the emotional journey.

When people become parents for the first time, their network showers them with wisdom and advice and invitations to call anytime of night because the first years are so sleepless and are often emotional rollercoasters. When people become entrepreneurs for the first time, there’s much less social understanding of what are helpful things to say, because it’s not as common of an experience — though arguably of similar significance.

When I became an entrepreneur for the first time, an important mentor in my life who is a fellow entrepreneur gifted me several plants to put in my new office with the kindest note explaining their significance to her in her own journey. She understands and will be there for me was the takeaway I had from that early experience. She was the person I would (metaphorically) call in the middle of the night. And I did. And I could have not made it through some of those metaphorical nights all the stronger without her support.

Progress, to me, looks like this: entrepreneurs and founders talking about the shared experience in a new way, normalizing the challenges — as they happen, and as messy as they can be. Progress looks like sharing experiences with peers even in the midst of fundraising, acquisitions, or whatever thing-of-the-moment whose failure cannot be granted and trusting. Progress is acknowledging that not everyone will have their mentor who gives them a plant and the invitation to share the journey, and progress is stepping in to be that for each other. Progress is also more funders and investors who encourage and prioritize this balance for all their founders.

I read an article about this phenomenon recently that likens the experience to someone riding a lion. Most look at the person on the lion and think: wow, they are really brave and have it so together. And the person on the lion is thinking: how did I get on this lion and how do I keep from getting eaten?

Of personal significance to me, lately, is the vacuum of conversation about dismounting the lion. There’s little conversation that I’ve seen from or about entrepreneurs who stepped aside to help their company grow into the next phase. i.e., There was no acquisition or other major event, it was just the right time. Common startup culture lore would have you believe you either ride the lion off into the sunset or you get eaten. But what if you just step aside to make space for what’s to come? Let’s make that part of the conversation, too.

What do you think?