How to Break Up With Your Own Business

Walking away from a passion project is hard, but it could be the best move for your career.

After you’ve poured your time, energy, money and creativity into a business or side hustle, how do you know when it’s time to call it quits? This question is faced by many entrepreneurs, and figuring out whether you’re in a temporary lull or a permanent downward spiral can be challenging.

For Marlo Scott, former owner of New York bar/restaurant Sweet Revenge, the first five years, starting in 2008, were bliss. She won a Time Out New York Eat Out Award, had her cupcakes featured on The Martha Stewart Show, and starred in a JPMorgan Chase credit card ad aimed at small businesses. Scott built up a loyal customer base in a thriving area of the West Village. Her personal success story, going from the corporate world to being an up-and-coming restaurant industry entrepreneur, was featured in national media, and on a site about doing what you love. All was running smoothly — until it wasn’t.

After five years, a few key factors shifted. With looming rises in the minimum wage, Scott did the projections and found that increase “would be financially devastating to a small business like me.” Add in food delivery services that made it easier for people to chill at home than venture out for a dinner and drinks, plus a downturn in street traffic and 18 businesses or restaurants within one block of her closing in a year and a half, Scott says, “It was just epic devastation all around me.”

Three years before her 10-year lease was up, Scott looked into pivoting to a new food business, such as ice cream, but the desired high-quality ingredients made the cost prohibitive. None of the options she explored made financial sense. She decided to stay until the end of her lease, even though “it was very draining financially, mentally, emotionally and physically.” She thought about seeking out investors, but wasn’t in the right state of mind. “That’s not a point where you want to go asking for money, from a point of weakness. It was tough because you think if I just work harder, but there’s nothing more you can do. It took me so long to make peace with the fact that I had tried literally everything I could do.

I know Scott from the 10 years I spent as a cupcake blogger, a side hustle I started in 2004, before I’d ever heard the term. I intended to have a hobby, not a business, but it soon grew into one that grossed $25,000 a year, split between me and a friend I partnered with.

I didn’t just blog about cupcakes; I lived and breathed them. I spent one to two hours a day scouring the internet for news. I reviewed cupcake bakeries whenever I traveled. I never thought about quitting, until our ad revenue dropped by 90 percent. By then, I no longer had a full-time job with the blog on the side. The blog was a crucial part of my income, so I had to make the painful decision to ease out of it to have time for more-lucrative work.

While the decision can feel bittersweet — or just bitter — there’s often a silver lining to closing one boardroom door and opening another.

But money isn’t the only reason to leave a side hustle. Sometimes, your heart just isn’t in it anymore, as was the case for fashion blogger Farrah Romaine, who quit her online boutique Couture Diva after experiencing “major burnout.” Of the experience, she wrote, “I was seriously unmotivated and I began to question everything I had been doing up until that point. Was it still worth it?”

That’s a question producer and media strategist Wendy Sachs, author of Fearless and Free: How Smart Women Pivot — and Relaunch Their Careers, told me anyone considering this type of move needs to ask themselves. “Are you doing it for the income or because it’s giving you a creative freedom that you’ve never had before and you’re getting gratification?” she said.

Pondering this is exactly what Scott did. “I had to make a decision. Did I want to keep this dream alive, which was killing me, or take a bet on a new dream and have peace in my life? I decided peace was more important than anything else,” she said, calling that choice “a huge relief.”

Sachs also recommends utilizing the services of a financial advisor to look at your books to determine how much money you truly have. How long can you keep running your business, or how much debt can you sustain before the business or side hustle is “so stressful that it’s not worth it. If it’s not sustainable, you shut down.”

When your side hustle starts to interfere with the rest of your life, that can be a sign the end is nigh. Isabelle Lichtenstein, Associate Editor at Go Magazine, worked as a face painter during college, earning $75 an hour for 15 hours a month at the height of her business. The red flag waved for her when she pulled an all-nighter to finish schoolwork plus a new side hustle, freelance writing, and had to paint faces at a party the next day. “It just became too much to juggle. At first, I felt really sad, because I loved face painting, but I knew that in order to begin the career I wanted, I had to let it go.”

While the decision can feel bittersweet — or just bitter — there’s often a silver lining to closing one boardroom door and opening another. “It comes down to getting extremely honest with yourself,” said Scott. “You have to ask yourself: Is this what you imagined? Does it actually make you happy? That’s such a tough thing for entrepreneurs.”

Scott wound up finding a job in Indianapolis working in marketing and PR around migraine medications in the pharmaceutical industry, and is completely content with her career trajectory, noting that she “should have gotten out sooner.”

Your business mojo isn’t over after one failure.

Sachs also acknowledge that there’s an emotional component to letting go of what you’ve poured your heart and soul into. “It can feel a little bit like grieving,” she noted. The good news? Having a varied resume is now commonplace. “You can have this full spectrum of professional lives and professional identities,” said Sachs, a former Capitol Hill press secretary and TV producer turned filmmaker, speaker and author. She considers herself a multi-hyphenate, and says “that’s a very modern way of looking at our professional identities.”

In other words, your business mojo isn’t over after one failure. In fact, Sachs urged women to take a cue from Silicon Valley. “What I’ve found is that the guys in the startup culture embrace failure when their companies blow up; they celebrate it like a badge of honor,” she said. “Here are these guys blowing through billions of dollars in venture capital funding.” And when they do, they don’t mind at all, assuming it’s simply a part of the business life cycle. 

Sachs said men also don’t take the shuttering of a business personally. “Women blame ourselves when things don’t work out, whereas guys look outward.” There’s nothing wrong with starting over, in the same field or a totally new one, either, explained Sachs. “It’s very accepted that there are going to be a lot of turns in people’s careers and there’s no linear path anymore.”

You can’t always predict what that path will look like, either. Scott sees her former business, and the decision to close it, as a stepping stone on her career trajectory. “My role in Sweet Revenge prepared me to have a different perspective on having a role in a big company,” she said. “I feel really fortunate. I didn’t understand the path while I was on it. You have to adjust your thinking. Before, I could make my own personal impact on a small patch of big giant New York City. Now I make a small impact on a really big company and I feel good about doing my part.”

Rachel Kramer Bussel writes about sex, dating, books, pop culture and herself. She’s the editor of over 60 anthologies, including Best Women’s Erotica of the Year, Volume 5, and teaches erotica writing workshops in person and online.