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Academics have started to investigate the kind of grief that hits entrepreneurs who’ve taken their one moonshot and failed

Madison Van Rijn/The Globe and Mail

I wasn’t like the other little kids in my hometown of Sydney, N.S. When my teacher in elementary school worried I was ogling the lingerie section of an old catalogue we were using to make collages, I was actually scoping out the living room sets. At home, in our small bungalow—the walls painted white, the carpet brown—I relished buying colourful little accents for my bedroom and the rec room, helping our house take on new life.

If small businesses are made of dreams, then the home decor store I opened eight years ago, Habitat, was a chance to live out my childhood fantasies. My goals were modest: to pay down my student loans, take the occasional trip abroad and enjoy the freedom of working for myself, doing something I loved. I’d put in more hours, sure, but I’d do it on my own terms. In December 2013, five years out of university, the dream came true: I welcomed customers into a high-ceilinged shop in downtown Cornwall, Ont., kitted out with cherry fixtures and a grey-green accent wall, stuffed with candles, throw pillows, curtains, kitchen tools and imported jewellery.

But things didn’t go as planned. I’d estimated daily sales of $300, six days a week. On good days, however, I’d only bring in $100—and good days were scarce. By May, I was already struggling. I’d put off paying bills and borrowed money from family and friends to stay afloat. The next month, I slapped a “Closing” sign on the door and gambled on a storefront 45 minutes down Highway 401, in Brockville. It was another historic building, but in a downtown with more tourists and foot traffic, lots of coordinated shopping events and, hopefully, a happier ending.

It’s no secret the odds are against small businesses. More than half fail within the first five years. And even that last-ditch move to Brockville couldn’t save mine. Amid a terminally grey winter, when I slept in the back of the store and fell behind on my rent, my remaining money, patience and energy evaporated. In February 2015, I closed my doors for the last time, joining the roughly 39,000 businesses who do so each month in Canada. My journey was over—but I was about to embark on a new one that would take me through the stages of grief as surely as if I’d lost a beloved friend rather than a business.

And I was completely unprepared for it. The tiny section in my business plan headlined “exit strategy” proclaimed I’d sell off what I could to pay my debts. (In reality, that barely made a dent.) There was nothing about how letting go of the business would be a much longer and more complicated journey than owning it.

Today, a huge swath of entrepreneurs find themselves in a similar position due to COVID-19. The Canadian Federation of Independent Business estimates 50,000 entrepreneurs have already been driven under, and a total of 200,000 might ultimately close once the full effects of the pandemic have hit. Which means they’ll face the same erratic journey back to wholeness that I did. Mourning together, but alone.

There’s a certain optimism required in entrepreneurship, and I remember the excited conversations I’d have with a nice couple around the corner from my store in Brockville. They’d made a mid-life career change and opened their own hospitality business, and when they’d wander past my place, we’d chat about our successes, feeding off each other’s positivity. If one of us could make it, we all could.

But with my store showing its weaknesses early, I noticed they stopped waving when they walked by. Then their visits stopped all together. I felt like a traitor. As I packed up what was left of my dream, with workers from a local charity boxing my unsold items to give away as door prizes, I remember having to fight off a panic attack so bad that I thought I was dying.

Madison Van Rijn/The Globe and Mail

Once I’d locked up for the last time, I headed west on the Greyhound in search of distraction. I bounced around short-term sublets and worked as a barista, trying to pay off my business and other loans and save for journalism school, which I’d decided would be my next chapter. But I was angry and sad, and spent my spare moments relitigating every decision I’d made, trying to make sense of my failure.

I didn’t know it then, but I was in the early stages of grief. Psychiatrist Elisabeth Kübler-Ross developed her now-famous five stages—denial, anger, bargaining, depression, acceptance—in 1969, when she published On Death and Dying, based on interviews with people experiencing terminal illness. And though grief research tends to focus on the death of a loved one or the collapse of a relationship, a few academics have started to investigate the kind of grief that hits entrepreneurs who’ve taken their one moonshot and failed.

Michael Freeman is a psychiatrist and clinical professor at the University of California, San Francisco, who has been researching entrepreneur mental health for 15 years. “Entrepreneurs can feel about their business the same way parents feel about their children,” he says. In fact, he adds, a team of researchers in Finland took brain scans of entrepreneurs who’d lost a business and compared them to those of parents who’d lost a child. “And they found the same kind of footprint between the two groups. So when a business fails, the intensity of the grief can be quite full.”

I kept my head down and worked—a lot, having taken a part-time job at a local radio station on top of slinging lattes. But I couldn’t stop the questions that zoomed through my head day and night. At the grocery store. In the shower. Taking a walk. Lying in bed on the cusp of sleep. What if I’d doubled my loan request? What if I’d rented a cheaper storefront when I first opened in Cornwall? What if I’d posted more pictures of my inventory on Facebook? What if I’d opened a few weeks earlier? What if I’d charged 10% more storewide?

Dean Shepherd, a professor of entrepreneurship at Notre Dame University’s Mendoza College of Business, calls this loss-oriented processing of grief, where we build an account of why our business closed. And while it’s a necessary part of the healing process, it can go too far. “We think about how bad we feel and it actually starts to increase our negative emotions,” says Dr. Shepherd, one of the world’s leading researchers on the subject of entrepreneurial grief.

Madison Van Rijn/The Globe and Mail

The flipside of loss-oriented processing is restoration-oriented—taking concrete steps toward a new life, such as selling a house, planning a move or looking for a new job. But that can be dangerous, as well. “The problem with that particular way of doing things is that while it tries to push negative emotions to the side, those negative emotions eventually have a way of percolating up,” says Dr. Shepherd. “And they might come up at an inopportune time.”

He saw this in action with his own father, who lost his business when Dr. Shepherd was young—an event that inspired him to study entrepreneurial failure in the first place. His father put all his energy into the restoration side of his grief and didn’t engage with the loss. “It was probably 10 or 15 years later, and we still wouldn’t talk about it, because we knew that it would bring up all sorts of pain,” says Dr. Shepherd. “I’m not sure he ever fully got over it.”

Much like his father leaning toward restoration, everyone has a default orientation for grief, he says. But he proposes a specific model, based on one first identified in the 1990s, that involves alternating between restoration-oriented and loss-oriented methods of grieving. So an entrepreneur could work on that loss accounting and then switch over to restoration in order to recharge their emotional batteries and help reduce secondary causes of stress, such as worrying about paying the bills. Then they can toggle back and forth as needed.

Inadvertently, that’s the sort of model I followed when processing my grief. Instead of, say, moving back in with my parents and wallowing in sadness, I got a job (albeit one that paid an hourly wage and forced me to deal with angry customers all day) that would help me slowly pay off my debts and plan for a new life. At the same time, I still subjected myself to the emotional questioning that went along with closing shop. That’s how I was able to come to grips with the fact that virtually nothing would have saved my store. Sure, I could have paid less in rent, but a cheaper storefront would have lacked the visibility and walk-in traffic of my original location. And doubling my loan would’ve just left me deeper in the red after the inevitable closure.

It was gruelling work—but that’s nothing new for entrepreneurs.

The most challenging times through all this were the moments I couldn’t do anything at all. That’s one reason I liked working two jobs in the aftermath: It was a helpful distraction during that first challenging year. But sometimes, when I had the night off, I’d be nearly overwhelmed by feelings of failure and loss.

But as the adage goes, time really does heal all wounds. “It could be a year, it could be five years,” says Dr. Shepherd. “We can accelerate it by using these different processes, and some people will be faster, because they’re better at using these processes.”

So it went with me. Gradually, I became more generous with myself, and after the first year, I was over the worst of my grief. There’s a difference between knowing intellectually that you’ll be okay and truly believing and feeling it. I can’t tell you the exact moment it happened to me; I just know that it did. (Dr. Shepherd adds that not all entrepreneurs will go through the grieving process—they might not feel as deeply affectionate toward their side hustle or ultra-lean startup as I did toward my long-cherished dream.)

But to truly rebound from the failure of my business—both emotionally and financially—took about five years. That’s how long I spent struggling to pay off my debts and establish myself in a new career. It took nearly as long to rebuild some lost components of pride and self-esteem that had disappeared along with my erstwhile identity as a business owner, to stop looking back on the experience with resentement.

Five years is a long time, and it can be hard for entrepreneurs to hear it might take that long to properly come to terms with a business loss—especially when they’re still fighting to stay afloat. But when I embarked on this journey myself, I wish I’d had a better handle on what I was about to face.

In the intervening years, I’ve become a more mindful person—and I can see how that would have helped me immensely when I was still in the thick of running my store. It wouldn’t necessarily have changed the outcome, but I definitely would have had a softer landing if I’d been able to separate my business failure from my own personal sense of worth.

That’s why it’s encouraging to hear about researchers like Jeffrey Overall, an associate professor of business at Ontario Tech University in Oshawa. Part of his research focuses on the impact of mindfulness on entrepreneurs, and one of the projects he works on, called the Global Institute for Conscious Economics, has at its core the idea of creating a healthier, more mindful relationship between businesspeople, money and the wider economy. In this era of hustle culture and success bias, that could help change the tenor of the popular discourse around failure—and by getting this notion into entrepreneurs from the start, it could help create savvier, more resilient operators.

“If you’re engaging in these processes of mindfulness and conscious awareness, you can pull out those really important gifts to take away that make you a better businessperson and also a better person because you’re evolving,” says Dr. Overall. A bonus, he adds, is that it allows you to avoid repeating the same issues that “might have gotten you into that place of needing to grieve a business.”

For a long time, I had a recurring dream: I’d return to my store and find everything just as I’d left it—as though I’d locked it up one night and never come back. Sometimes I felt so relieved that I’d find myself close to tears—grateful to have avoided all the pain and embarrassment that came with closing Habitat for good. But then I’d wake up and remember I had indeed failed, and the grief would wash over me again.

Then one night, I had that same dream and found myself feeling disappointed. I have to go back to this? I thought. But I like what I’m doing now.

That might not have been the sign I was healing from my loss, but it was definitely a sign. If nothing else, it felt like a rare reward for doing the work that continues long after most people will admit it does.

There are still certain dates or times of year that trigger those feelings of sadness, often courtesy of Facebook memories—my opening day, a sunny spring morning after I’d barely survived that first tough winter, a post announcing the store was shutting down. But there’s enough distance that it no longer feels wounding to think about. I can once again browse through a home decor store without feeling a pang of discomfort.

My business was part of me. It always will be. I loved it once and imbued it with great hopes. And even though I lost it all, I survived.

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