Why I Don’t Regret Quitting My Job to Run a Startup

January 24, 2016, 4:00 PM UTC
Employees of start-up companies work at their designated spaces at the offices of 1776 business incubator in Washington DC, February 11, 2014. 1776 hosts about 185 start-ups in its offices. The incubator gives members a chance to take notes from high-profile entrepreneurs during what are known as lunch and learns. 1776 runs like a campus, with workshops, a communal kitchen and 24-hour access for members. 1776 was founded in January 2013 by Evan Burfield and Donna Harris, a pair of successful entrepreneurs with experience building companies and communities. AFP PHOTO/MLADEN ANTONOV (Photo credit should read MLADEN ANTONOV/AFP/Getty Images)
Photograph by Mladen Antonov via AFP — Getty Images

The Entrepreneur Insider network is an online community where the most thoughtful and influential people in America’s startup scene contribute answers to timely questions about entrepreneurship and careers. Today’s answer to the question “When making a tough business decision, how do you know when to trust your gut?” is written by Michelle Gadsden-Williams, cofounder and COO of Ceiling Breakers.

It was Friday morning in New York City, and I was scheduled to have a one-on-one meeting with my boss. As usual, I had my talking points typed out in ascending order, with a copy for my boss to review during our discussion. I silently rehearsed the conversation in my head, and after a few minutes of small talk, I began by submitting my resignation as the managing director & global head of diversity and inclusion at one of the world’s leading financial services firms.

I had been thinking about this decision for quite some time, and all sorts of things were going through my head. What would they think? Is it the right time? Am I making the right decision? Moreover, the most difficult challenge that I had to face was rationalizing my decision to family and friends. I had the position that most professionals dream of—global, influential, impactful, and above all, it was the position that I had worked incredibly hard for during my 25-plus years in corporate America.

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And here it was—I was going to “tap the mat” like a wrestler, quit my job, and pursue the unconscious dream of becoming a full-time entrepreneur along with my husband. Who does that? I do, apparently.

But my decision was indeed rational and well thought-out. I knew exactly what I was doing by resigning and what the implications would be. My husband and I talked about the pros and cons of my decision, and even covered the worst thing that could’ve happened. I’ve led a lifetime of taking calculated risks, which have all resulted in wonderfully positive outcomes. Why would this life-altering decision be any different?


I also sought the counsel of my father, a retired executive, who coached me to think logically about the decision and to remove emotion from the equation. I also have an invaluable ecosystem of friends, colleagues, and others who were personally invested in our success. All I had to do was ask for help—which isn’t as easy as it sounds. Given all of those factors, I had everything that I needed in order to make a sound decision and be successful. At the end of the day, should the entrepreneurial venture not work out, I can always reinvigorate a corporate career by keeping my relationships alive and nurtured.

Every day, we all face decisions that we need to make. I learned years ago that you simply need to put pen to paper and go through what many call a “plus/delta exercise” which, in essence, places value on the choices that you want to make. Examine the risk vs. the reward again and again. You do this until you have come to a decision that you can live with and ultimately articulate. Be clear about your intentions and the problem that you’re attempting to solve, and remove emotion from the equation. At the end of the day, it’s all about trusting your gut. I am extremely happy with the decision that I’ve made—I’m flexing new leadership muscles and every day is new and different. At this stage of my career, I could not have asked for anything better. The rewards certainly outweigh the risks by a long shot.

Michelle Gadsden-Williams is the cofounder and COO of Ceiling Breakers LLC, a multi-faceted business focused on diversity consulting, media-driven women’s empowerment initiatives, and diverse entertainment investments, based in New York City.

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