In-House Counsel

Do This If You Love (Or Don't Love) Your Job

on February 16, 2023 at 10:43 AM

Early in my career, I landed my dream job at a dream company. I was the first attorney at Etsy. For an artist turned lawyer[1] I couldn’t have been happier with my day-to-day work, the culture, and my colleagues.

And then, one unassuming day, around six years in, I floated into my buddy’s office for a regular chat about something regular (it was probably contracts related).

After we moved past the matter at hand (contracts), he got serious. He glanced around and lowered his voice.

“Sarah,” he said, “are you interviewing at other places?”

I felt question marks pop up all over my face. I silently shook my head “no” as fear crept in.

Did I mess up the agreement? Was he trying to warn me of something? And if not, why would I cheat on my role, my work friends, the Etsy community, or this amazing business? Did he think I should leave? Who would ever look elsewhere if they existed in a dream?

I stared at him.

We were close enough for him to read my face.

“Interviewing,” he explained, “is a skill. You must practice this skill or it will get stale. You have been here a long time but remember, you’re not married to a company. There’s no ‘til death do us part.’ Keep an open mind. It’s important to understand your options and your worth. Unexpected events happen in life, family, jobs, businesses, and the economy. Even if you are satisfied, even if all is good, once a year, interview for a new role. Don’t half interview and don’t passively interview. Seriously interview.”

I nodded as I clutched the contract we had just discussed. It was a lot to take in.

Because of this advice, I paid closer attention to the job market, applied to opportunities, and actually answered recruiter emails. I dissected what my next role might look like. I detailed the type of company, executive team, finances, role, compensation, and culture. Seriously interviewing took serious effort. And then, several years later, when my personal circumstances changed, and it was time to wake up for the next dream, I had recent research, a network, and muscle memory.

As layoffs and disrupted lives fill my newsfeed, it’s easy to relate. It could have been me. It could have been any of us.

I’m reminded of my work friend who positively altered my career trajectory. If you love your job (or if you don’t love your job) seriously interview for another role at least once a year. Who knows, you may find an even better fit. But if not, this is one small and serious way to try to prepare for the unpredictable.

[1] For those of you who have been following my journey, I turned back into an artist.


Sarah Feingold (she/her) is a Brooklyn-based startup attorney (formerly first Lawyer and General Counsel at Etsy and Vroom), artist, playwright, investor, board member, speaker, candy eater, and mom. She teaches Media Law at NYU’s Tandon School of Engineering and received The New York Law Journal’s General Counsel Impact Award. Sarah’s worlds collide in her new play, Dirty Legal Secrets – www.sarahfeingold.com

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