Within 20 months, my stepmother, my best friend and my brother died. My burnout, if that’s the right word, started somewhere in those 20 months. I question the word as it did not feel so much like a thing burning out as a choice that had run its course. Until March 2015, I managed the digital business of a major US sports league, a six year stop on a road that started over 15 years before with a NYU law degree, a stint at a major law firm and time as general counsel of a national magazine publisher.

The catalyst for those years was another death, that of my mother when I was in college. It was unexpected and I felt untethered and alone. I choose a stable professional path to ensure that I could support myself. For those 15 years, I drew some satisfaction from the quality of the work I did, guided by my “internal barometer of excellence,” a phrase introduced the first day of law school by the dean to describe that thing that made my classmates and me high achieving people. My work reflected well on my abilities but neither let me exercise them fully nor felt organically connected to me.

Before her death, my best friend, an author of a memoir about her struggle with breast cancer, frequently voiced her frustration about the things she had not achieved. I reminded her that ten years in treatment while raising a child and writing a book seemed more than ample accomplishments. She said it was not enough. I know what she meant, not about her but about me.

Even before my stepmother’s death, the first in the series, I understood that I was disconnected from my work. I wanted to direct and own the fruits of my labor. I spoke to a few recruiters about a move to an early stage company, stressing my need to help build something. I would consider any product or market but had to feel passionate about the company’s mission and executive team. I looked at a few options but nothing seemed right.

At a dinner in August 2014 days after my 25 year-old brother’s funeral, a dear college friend asked me about working on a start-up in the online kid’s consignment space, the idea being better stuff, less waste. Here was the opportunity to build a business I believed in, with a community of women I felt connected to. Several months of research and discussion got me sufficiently excited to quit my job and work full-time on the site. A start-up may hardly seem like the thing to do when burned out but for me it was a means to stave off a potential regret, a regret that that I did not accomplish enough, that I did not try, that I ran out of time.

Originally published at medium.com