Photo-Illustration: by The Cut; Photo: Getty Images
It’s the dream: Start your own business, be your own boss, and control your own time. But in reality, this is a bleak time for entrepreneurs, especially small-business owners who have to deal with whipsawing tariffs, inflation, and rising costs of living. “Almost every small-business owner I know is getting squeezed, especially the ones who work in hospitality,” says Amanda, who owned a chain of cafés in Los Angeles that closed a few years ago. “I’m so glad I got out when I did.”
But when you own a business, you can’t just quit. There are employees to consider, investors to report to, and orders to fulfill. The decision to close your doors is complicated — and lonely. “I didn’t have anyone to talk to about it,” one former business owner told me. “None of my friends understood. They were like, ‘What? We love your store. You can’t close!’” Here, three entrepreneurs who shuttered their businesses talk about burnout, identity crises, and what they’re doing now.
—Jamie, former owner of an ice-cream shop in New York
Throughout the eight years of running my business, I went in and out of burnout several times. The first was when the business was a year old. I had gone through the extreme stress of opening a storefront, being in the grind every day. I got hives that first summer. Then, when winter hit, I was super-depressed and miserable and realized I needed some help. I found a consultant who specialized in small food businesses, and she helped me so much. She also made me feel less alone in what I was going through.
I know that running your own cute storefront in New York seems like a dream. But you have to be on top of so many little things all the time. You have to make sure your fire extinguisher is up to date, because someone will pop into your store and check. And employees can be so difficult. It’s exhausting, physically and emotionally, to hire people, train them, and deal with all their B.S. And you can’t be friends with them at all. I had a bunch of employees that I trusted professionally, but for everyone’s comfort, I kept my distance — and that can be isolating.
Customers in New York are very difficult too. So many people want you to make them something special that’s not on the menu. And at first you’re like, “Oh yeah, we can figure this out.” But then it becomes taxing for your employees, and it’s hard to figure out pricing. After a while, I was like, “I’m sorry, you need to order the sizes that we have.” But customers don’t want to hear that.
I felt like a lot of my friends couldn’t relate to what I was going through professionally, either. They would talk about how stressed they were at work. Then, when I would say I was stressed, they couldn’t understand — they were like, “But you’re your own boss!”
Five years in, I decided to close the storefront and focus on my wholesale business. I had started selling the product in supermarkets, and that seemed much more scalable than the store. I was also trying to run a frozen-dessert cart — I shudder thinking back on it. I was just trying to do too much. And that kind of burnout led me to make decisions that I wasn’t proud of. There was one point when I didn’t have anyone with a food handler’s license working at the store at night. I was lucky, because the one time the food inspector came, I was there late myself, so it was fine. But it was such a close call. And up until then, I had always been so careful. I never took risks like that. But things had gotten to a point where I had so much else on my shoulders that I was letting things go.
When I closed the store, I was really optimistic about raising money to expand the wholesale business. But it wound up being even more challenging and isolating. I was working in a basement, packing the product mostly by myself. I was testing our recipes, sampling the product at the distribution center, going upstate to meet suppliers, analyzing sales, pushing coupons, and going to stores to make sure that the product was being displayed correctly, all on my own. It was a lot.
I was also trying to fundraise. I went to all these pitch competitions and was constantly following up with potential investors. And it got to the point where I was tired seeing all these other entrepreneurs raise money, but not me. I was seven years in, and I didn’t want the next seven years to be as hard as the first. That’s why I decided to close in the end. I had raised $50,000, and that was not enough. I was waiting to hear back from some other investors, and when they said “no,” I was like, I’m done. I knew I’d given it all I had.
Still, closing was extremely painful. My business was a huge part of my life and identity. I felt ashamed. Like, why couldn’t I make this work? It was embarrassing. One of my mentors told me that women entrepreneurs often struggle with closure a lot more than men, and I think it might be true. I would bump into guys I met at pitch competitions, and when I asked them how things were going, they’d be like, “Oh, we closed. The margins were too small and we couldn’t make enough money. No big deal.”
I also found it really difficult to find a new job. In my experience, nobody really wants to hire someone who has run their own business before. I looked for months and months. Finally I ended up going to real-estate school, because real estate is sort of entrepreneurial. You get your license, and then it’s up to you to make the sale. And I had a ton of experience in sales. Serendipitously, I also met my husband around that time. And when the pandemic hit, we moved abroad. Now I have two kids and I haven’t worked for the past couple of years. It’s bizarre sometimes. Like, “Mommy used to have a business.” But I’m working on starting something new. I’m just much more careful about my boundaries these days.
—Amanda, former owner of a café with multiple locations in Los Angeles
When I started my business, it was out of pure passion for creating community spaces that brought people comfort. I wanted to provide an atmosphere where people could forget about the shit in their lives and feel better, and it felt like there was an art to that.
There was no strategic business plan in the first year. We were just throwing spaghetti at the wall, saying “yes” to everything, and the business grew. Pursuing this entrepreneurial dream, especially in a big city, felt great. This is a place where people appreciate craft and quality, so our success was very satisfying. It was not just a job and not just work — it was everything that I believed in.
Financially, the business was all bootstrapped. I put in my own funds and worked 18-hour days nonstop. Any money we made, we put back into the business, and that was how we operated for quite some time before we got our first investment.
Accepting money from investors is one thing I would do differently if I could do it over again. We were very green when it came to raising capital. Once we got the investment, I had to report to investors who were treating us like a tech company in terms of what they required. It allowed for growth, which was good, but also, to what end? When you’re running a successful business in a major city, everyone’s like, “When are you going to open up your next location?” And you’re growing just for growth’s sake.
As we got bigger, things got more stressful. And even though we were profitable, we got into this cycle of always looking for additional capital. A lot of investors were like, “Well, after you get to this number of locations, come back to us.” So I was like, “I guess I’d better open up some more stores, because if we get to that next point, we can get access to more capital, and it’ll help us do all these other things that we want to do.”
Another thing I wish I had done differently was think more about what I wanted for myself personally. I had goals for the business, but not for what my own life would look like running it. In hindsight, I wish I’d been very clear on that from the start, and revisited that vision as I went along.
We hit the ten-year mark and that was significant. We had five permanent locations and a few pop-up locations. I definitely felt a little burnt out, but then the pandemic hit and the stress was on a whole other level. Suddenly the work became totally joyless. When you’re stuck with multiple retail locations and leases and so many employees that you’re responsible for, you can’t go anywhere. I had never thought that in building a hospitality business, I was building what became a trap. All the satisfaction it had given me before suddenly evaporated overnight. I went from trying to grow the business to trying to save it. We were in defensive mode with no breaks. I didn’t have any time to take care of myself. My mental health was in a bad place. I felt helpless and completely out of control of my life. But it never occurred to me to quit. It just wasn’t an option. All the people I employed would just be jobless. I couldn’t do that.
I managed to get us through the pandemic, but all that stress and trauma changed everything. Not to mention the cost of everything — transportation, logistics, materials — practically doubled, and it became unsustainable. I didn’t feel capable of being the best leader anymore. And then I just stopped wanting to go to work. When it’s your own business and you don’t want to go to work anymore, that’s when you need to throw in the towel. I realized that I wanted to build a life for myself that was separate from the business.
I have always been an all-in person, an incredibly hard worker, dedicated to whatever I do. So deciding to get out of the business put me into a total identity crisis. It also took a long time, about a year. I had multiple locations and a fairly big team, plus I had investors — I couldn’t just quit. It took a lot of work to unwind, and I never stopped. In the end, I was able to sell the business and exit. But not at the valuation that was my initial goal. At that point, it wasn’t about the money to me.
When it was finally over, I was so relieved. But it was complex. I didn’t know who I was outside of my business. I took a bunch of time off. I went to therapy. I had so much to process that I had just shoved aside for years. But there was also a big sense of freedom. And that felt great. I used to think that getting out of the business meant failure. But in some ways it felt like a huge accomplishment.
Figuring out what to do next has been interesting. For now, I’m consulting for other businesses. There’s tons of freedom and flexibility. But sometimes I miss the sense of accomplishment that I used to feel. I’m helping others, but there’s no ownership in it. Overall, though, it’s amazing, and I love helping other businesses. I’m never stressed. I used to dread looking at my phone, because I knew it would just be bad news about the next emergency that I’d need to deal with. Now, sometimes I don’t look at my phone for an hour or two, and it’s fine. I’m so glad I got out when I did. Now, with all these tariffs going into effect, how the fuck can you run a business anymore?
—Marisa, former owner of a beauty salon in New York City
It was actually a relief when I closed my business in 2020. I’d been running it for eight years, and I had struggled a lot in 2019 — I’d tried to expand with a second location, but it didn’t work out. I had a lot of debt from the expansion and I didn’t have a way to pay it back. Then COVID hit, and even though it was awful, it was also kind of nice. All aesthetician businesses were shut down by law, so my phone wasn’t ringing, customers weren’t reaching out, employees were furloughed. I’m not saying that it was a great time, but I did feel this subtle kind of peace. My employees were collecting unemployment, so I knew they were okay.
I decided to close permanently later that spring. It honestly didn’t feel like a hard decision at the time, but even now, five years later, I don’t think I’ve fully processed the loss of my business. Before I closed, I did get a very large loan from the Small Business Administration, and that was comforting; it gave me something to fall back on. My lease was up and I’d been burned out for a while.
Initially I rented a two-bedroom apartment and used the second bedroom as a treatment room for clients. I used the small-business loan to pay a portion of my rent, and it was nice to start working again. But long-term, I never really wanted to do treatments from home. That was never the goal. It felt weird, like my home wasn’t my home. I’d make lunch and then I’d be like, Oh, I’ve got to open a window so it doesn’t smell like salmon in here when clients come in. The energy around what I was doing had shifted, and I just was kind of over it. After a decade in the industry, I felt like I’d done all I could do. I’d owned, operated and scaled a business in arguably the most competitive city in the world. I felt proud of myself, and I felt good about bowing out.
I did a total career shift and got into the craft-beer industry. It might sound random, but I’d always loved craft beer and I love the science of how things are made. I took online craft beer courses at Cornell and San Diego State, and then I did a two-week volunteer program with a brewer in Colorado. Then I got a temporary remote job for a craft-beer brand. It didn’t pay a ton of money, so I couldn’t afford to stay in New York. But it was a great opportunity to travel around a little bit. I wound up visiting Tennessee and found an affordable apartment that was within walking distance of a couple of breweries.
Now I work for a tasting company in Tennessee, scheduling beer tastings at different venues, and then I work at another brewery a few days a week. I love it. Sometimes I do miss being my own boss, but I feel incredibly lucky. Craft-beer culture is very relaxed. The customers are great. The people I work for are all fantastic. I make a lot less money than I used to, but I also have a lot less responsibility and pressure. I just collect a paycheck and go home. My boss’s decisions are not my business, and I’m happy to have that distance. I don’t want to live to work. To me, freedom equates success. And in that sense, I have achieved something really fantastic.
I do have a ton of remaining debt, though, and that’s extremely overwhelming. I don’t think it’s anything to be ashamed of, but it does feel daunting and scary. So I’m working on paying it off, but it’s slow going and it’s going to take me a very long time.
I still find myself telling people, “Oh, I used to own my own business in New York,” like I’m trying to prove something. It’s hard to go from owning your own business to working for someone else and making less money. It’s a blow to the ego. But I don’t want to be that person who’s like, “Oh, back in my younger days, I was the star quarterback in high school.” So I try to be mindful of it. And I feel so much happier in a smaller city that’s slower paced. I have a house with a yard and a dog. When I look at what other people in Tennessee are making, salary-wise, it’s on par with what I’m making. I’ve gained a lot and my needs are always met.
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