Building wings on the way down, or: How an achievement addict finally learned to fail.

https://commons.wikimedia.org/wiki/File:Dr._Michael_Wolff_Cliff_BASE_Jump,_Blue_Mountains,_Australia,_2001.JPG
“You’ve got to jump off cliffs all the time and build your wings on the way down.” ~Ray Bradbury

I started a business and it failed. This post represents my first public attempt to make sense of what happened.


Not to brag, but I’ve always been really good at stuff.

I was a starter who helped my high school women’s soccer team go all the way to the state championship—the furthest the team ever advanced before or since. I won 6th place in Jumpers at the American Quarter Horse Youth Association World Championships at the age of 15. I’m an International Lindy Hop Champion. I have a Ph.D. in Philosophy and Women’s Studies.

After completing The New Movement’s improv comedy curriculum this winter, my Level 1 teacher lovingly called me “an achievement junkie.” She’s not wrong. As a high-achieving student who loved school, I took great comfort in knowing that my teachers would place clear obstacles in front of me, and my job was to overcome them. Pass a series of intense comprehensive exams on the history of Western Philosophy since approximately 500 BCE — check. Write a thesis — check. Defend a dissertation — check. My plan was to get published, teach philosophy or gender studies as a college professor for six years, then get tenured and ride off into the academic sunset.

After graduating in 2009 into the worst academic job market of my lifetime, I stepped off the comfortable track of obstacle-jumping achievements and into the scary unknown, where “what to do next” is totally unclear and unpredictable. It’s cool, though—after six months working 3 part-time jobs, I landed my first real job at Harvard. I was promoted to Director of the Harvard College Women’s Center just three semesters after being hired as Assistant Director.

What I’m saying is, when I put my mind to something, I really do it.

So when I co-founded recruitHER in late summer 2015, nobody who knew me was surprised. When we attracted national attention and got featured in publications like Austin Monthly and Austin Woman magazine, nobody was surprised. When we secured investment funding in late March, nobody was surprised.

When we closed the business one year after launch, everybody was surprised.

That should feel like a compliment. It should feel great that everyone expected us to be successful. But I’m now the co-founder and CEO of a failed business, and it hurts to say that.

I’m in great company—80% of entrepreneurs who start businesses fail within the first 18 months. People tell me having a failed business is basically a badge of honor in the world of entrepreneurship. I’m trying to tell myself that being part of the majority who fails isn’t something to be ashamed of or embarrassed by.

I’ve already hit my deepest depression and darkest place about the whole thing. My heart already broke because my passion project and only real “big dream” didn’t come true. I’m in the early stages of healing.

As a philosopher, my tendency is always to reflect on my experiences and figure out how to learn from them—what can they teach me about myself? As a communicator and community-builder, my impulse is always to share my lessons learned with others, so that I can help to build a bridge and support those who walk a similar path. This blog post is a halting attempt to start both of those processes. Here are my preliminary conclusions:


“Write hard and clear about what hurts.” ~Ernest Hemingway

Failure is hard.

Obviously, failure is part of life and absolutely necessary along the path to success. Turns out, accepting that on a personal level is actually not that easy for me. Failing at something I really care about has shaken my self-understanding. Before, every time I’d thrown my whole self into a project, that project was successful. I’ve been the first person to hold every single one of my professional positions (with the exception of my promotion to Director of the Women’s Center at Harvard)—I have a lot of experience creating value and building capacity from the ground up. Having failed, it’s hard for me to accept that my best effort wasn’t good enough. Throughout the process of launching and running my own business, I’ve been in the grips of a nasty case of impostor syndrome. Now that I’ve failed for real, it feels like confirmation of those fears.

As an expert on gender issues, I know that as a woman, I’m more likely to attribute my failure to lack of skill rather than bad luck. I’m working to adjust my perspective, because we definitely had some really bad luck. My business partner learned she was pregnant one month after she quit her job and helped me launch the business. Everything was rushed because the baby was coming and there was nothing we could do about that. One of our biggest clients had a massive internal meltdown, leaving some of our strongest candidates in the hiring lurch. The rest of our seed round never materialized. Our first, most critical hire didn’t work out.

Sometimes, giving your best effort and being extremely competent isn’t enough to overcome difficult circumstances. Although it’s easy to forget in StartupLand, “pulling yourself up by your own bootstraps” was originally meant to highlight the farcical nature of the endeavor.


“Strength shows not only in the ability to persist, but in the ability to start over.” ~F. Scott Fitzgerald

I am stronger than I ever realized.

Holy cow did a lot of super stressful things happen to me, and I handled them with grace under pressure. In the final weeks, I spent many sleepless nights tossing and turning, unable to turn off my brain and stop looking for ways out of our problems despite dead-end after dead-end. Until all the money ran out and our final options dried up, I did not give up. My mental health was definitely impacted. By the time we made the final decision to close up shop, my emotional and psychological reserves were 100% empty.

I’m also proud of myself for recognizing when continuing to press ahead would have done me more harm than good. Some entrepreneurs choose to put themselves into massive amounts of debt for the sake of their unshakeable belief in an idea and ability to execute. For some, that faith pays off huge dividends. But 8 out of 10 entrepreneurs fail in the first 18 months. I did the math and decided that my risk tolerance doesn’t extend to undermining my own financial well-being. Were I in my early 20’s, maybe things would be different. But as a mid-career professional, I’d rather close the chapter on this particular effort and live to fight another day.


“It isn’t what happens to us that causes us to suffer. It’s what we say to ourselves about what happens.” ~Pema Chodron

I am more than my business.

When I get out of bed in the morning, I remind myself that I am more than my business. That my expertise, my skills, my passion, and my network did not magically disappear when we filed for dissolution of the business. My passion for advancing inclusion and promoting diversity is not “over” just because my business is. I am not my business—I am much more than that.

I think about my career path so far, and how I never in a million years could have predicted where my professional journey would take me. Based only on my own experience, there are probably amazing opportunities awaiting me now that would not have been open to me had I not taken this risk.

I consider that the experience I’ve accumulated over the past year has been a massive education in business fundamentals, leadership, comfort with ambiguity, and an opportunity once again to practice the art of resiliency. All of these skills will serve me well in my next role. I’m a better leader and a more capable professional for having been through this experience.

I remember that my dissertation advisor told my parents at my Ph.D. graduation not to worry that I didn’t have a job yet: “Gina always lands on her feet.”


“As you navigate through the rest of your life, be open to collaboration. Other people and other people’s ideas are often better than your own. Find a group of people who challenge and inspire you, spend a lot of time with them, and it will change your life.” ~Amy Poehler

People have got my back.

One of the most wonderful things I’ve gained through this whole experience is opening up about our failure and finding supportive, generous, helpful people at every turn. Every person I’ve spoken to about our decision to close the business has been empathetic, encouraging, and offered a helping hand. I am forever grateful to learn that I’ve built a network made up of wonderful people who have got my back and value the notion of paying it forward. It’s liberating to realize that failure isn’t the end of the world, doesn’t say anything about my personal character, and is taken totally in stride by other people. Hearing others praise my efforts and validate my expertise is very reassuring.

I’m joining the world of folks who are able to turn to someone like me and say, “I’ve been there. It sucks a lot. But you’re going to be okay.” I’m incredibly inspired by the reactions I’ve received to everything we’ve been through, and it helps me to re-frame for myself what it means to be an achievement junkie who just went through her first major failure. Seeing myself through the eyes of friends and colleagues is immensely helpful.

I am more than my business. Failure is hard, but I am strong. And luckily, I’m surrounded by people who have got my back.

It’s going to be okay.

“I have not failed. I’ve just found 10,000 ways that won’t work.” ~Thomas Edison
R.I.P. | July 2015 – July 2016