How to Follow Your Gut—And Why You Always Should
Career Fit

How to Follow Your Gut—And Why You Always Should

THE BEST DECISIONS COME FROM YOUR GUT. ONE CONTESSA SHARES HOW SHE'S FOLLOWED HERS—AND HOW YOU CAN, TOO.

Law students and new attorneys often reach out to me for advice on how to enter the in-house world. I enjoy sharing my story—not only because it is hardly the norm, having started in-house directly from law school without spending time at a traditional firm, but also because my current role is one that came about by following my gut.

From the time I started law school, I knew I wanted to use my degree in a way that was closely tied to my interest in arts and culture. So after graduating from law school in 2005, I turned my attention to the field of Intellectual Property, earning a Master of Laws (LL.M.) the following year. During that time, I had an externship with music licensing heavyweight BMI, which is where I encountered my first in-house attorney. I immediately knew that in-house was for me, loving the idea of advising a business as opposed to individual clients, with the opportunity to contribute to a company on a broader scale.

When I’d share with lawyers that I was planning to find an in-house role straight out of school, my enthusiasm was met with doubt. Even with an LL.M, common thinking was that the only way to score that kind of gig was to start at a firm. But I was steadfast, determined to follow my gut.

A few months post-LL.M., I proved the skeptics wrong, landing an in-house position at New York City’s 92nd Street Y, a large and well-respected cultural and community center that was growing its legal team from one to two. At the time, the 92nd Street Y had begun widening its reach by making its programs available through third party media outlets and this required extra support in the area of rights clearance. While the job description didn’t exactly meet all of my criteria, as I knew I wanted to contribute across the board in the legal department, I believed this was a great starting point—an entrée into in-house lawyering.

And it certainly was—I grew up as an attorney at the 92nd Street Y, elevating my title from Legal & Copyright Clearance Coordinator to Staff Attorney to Associate Director of Legal Affairs. As planned, I threw myself into and contributed to the organization’s many businesses—sharing ideas, going to as many meetings and events as I could, and highlighting my skillset well beyond that of a traditional lawyer. After nearly 7 years, my gut kicked in again. Just as I knew out of law school that I wanted to work in-house, I now found myself feeling I was ready for my next opportunity.

It was around this time that I discovered SoulCycle. I was never particularly athletic, and exercise always felt like a chore. But SoulCycle, with its emphasis on a mind/body connection, was different. It was love at first ride. Each time I left class, I felt like a better version of myself. And, in the narrow hallway of this inspiring indoor cycling studio is also where I met my husband. SoulCycle was clearly a special place for me.

One summer Saturday at SoulCycle in Bridgehampton, I found myself out on the large deck, filled with riders socializing and shopping among the growing selection of SoulCycle retail gear. Taking in the scene, it appeared that the business was evolving, which made me think their corporate needs may also be evolving. Before we left, my then fiancé and I had the pleasure of running into one of the business’s co-founders. Our paths had previously crossed when I had the opportunity to inform the co-founders that they were our matchmakers!  

Once I returned home to the city, my gut got to work. I sent the co-founder an email, taking the opportunity to share my resume should the needs of the company expand in the legal realm. This is the way I look at listening to your gut. Zero regrets. Zero wondering. Go for it, and know you did.

This is the way I look at listening to your gut. Zero regrets. Zero wondering. Go for it, and know you did.

A few months later, I was invited to lunch at SoulCycle’s corporate offices. I was thrilled! I believed this could be a defining career moment. At the meeting, I shared what I knew I could bring to the table as an in-house attorney in a growing business model. I also knew from my years at the 92nd Street Y that I had more to offer beyond that of an attorney—from sharing concepts and ideas across departments to communicating with patrons. I learned that being more than an attorney is something that stayed with them from that meeting. About a month after that meeting, I started at SoulCycle and this February, I celebrated my two-year anniversary.

By following my gut, I landed my dream job. These are my tips for recognizing and following your gut, too:

1. Ignore Naysayers. 

Don't get discouraged by the opinions of others—if your gut is leading you in a particular direction, stay the course! {Click to tweet}

2. Trust Your Instincts. 

If you see a potential opportunity, go for it! Regardless of the outcome, there is much to learn and gain by putting yourself out there.

3. Believe In Yourself. 

Confidence is key. And, no one knows better than you what feels right. So don't be afraid to listen closely to your gut—whether it is leading you towards or away from a given job or opportunity. 

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The thing about “gutworking” too is that it doesn’t end with just the job offer. An in-house attorney is a company’s trusted advisor, and I tap into my gut each day in order to best carry out this role. 

I encourage everyone to listen to their gut, stay true to what they seek to do professionally or otherwise, and know you can make it happen.