eCommerce

How to Start Over as an Entrepreneur (2022)

Written by pgex7

Entrepreneurs face mental health challenges just like everyone else. And the stress of running a business can lead to burnout and feelings of isolation. In honor of Mental Health Awareness Month, we’ll be sharing Inspiring stories and wellness resources to shine a spotlight on the issue.


Stacey Moss’s business, one she had spent a decade building with love, burned to the ground in an instant. Young mom Sylvia Ng was diagnosed with cancer while she was in the prime of a tech career. And Carl Churchill tore through retirement savings after a recession took almost everything from his family.

What units these three tragedies is the way they ended. For these founders, the worst moments in their lives spawned something new—and better.

How do you start over after failure or loss? How can you rebuild your life while dealing with the weight of grief? There’s something built into the DNA of that allows them to see opportunity entrepreneurs everywhere, even in tragedy.

We spoke to six founders who faced everything from a death in the family to near bankruptcy, and built or grew their businesses from the ashes. They share their hard-earned advice on how to start over.

Starting over as an entrepreneur

Seasoned entrepreneurs know that failure comes with the territory. They are often the ones who try, fail, and all start over again. Entrepreneur mindset kicks in and transforms failure into opportunity. In fact, one study found that second-time had higher success rates than entrepreneurship newbies.

Sometimes, though, tragedy becomes the catalyst for starting a new business. When you have nothing to lose, there’s never a better time to go all in on that big idea you’ve been marinating.

Having a small business requires focus, which is just what a grieving person needs to carry on.

Trisha Trout, Prairie Sage Soap Co.

Yes, starting a business carries risk. When you’re at your lowest, taking on a new challenge can seem daunting. But entrepreneurship can also be empowering. Ask soap maker Trisha Trout. As she found, starting her business gave her agency over her own fresh start. “Having a small business requires focus,” she says. “Which is just what a grieving person needs to carry on.”

If you’re ready to start over and create a new life as a founder, or to rebuild your existing business from scratch, get motivation from the stories of Trisha and other entrepreneurs who’ve been there.

1. Invest in your own well-being

Monisha Edwards holds a candle from her brand's collection
Monisha Edwards, founder, Scent & Fire

When Monisha Edwards’ father was injured in a tragic accident, she was the one the family turned to. She became his caretaker and, thus, neglected the branding agency she had built—as well as her own mental health. After being diagnosed with anxiety and depression, Monisha decided to prioritize her well-being.

She started making candles after reading about the benefits of aromatherapy. Putting sel-care first helped her start over with a healthy new outlook. It also inspired her new business. As her father became more independent, Monisha built candle and fragrance company Scent & Fire and became an advocate for mental health issues.

Monisha learned that taking care of herself meant she was better equipped to show up for her staff and her business. And for her that meant starting a support network and taking advantage of available mental health resources. She even adopted a dog. Monisha encourages entrepreneurs not to go it alone.

“Look for startup programs,” she says. “Some will partner you with a mentor to help you with sales, marketing, or anything that you need to help you grow your business. It can take away some of that stress—and stress can lead to depression.”

💡 Takeaway: When you’re ready to start over, seek a community. A few supportive friends, a therapist, a life coach, or a mastermind group can all serve as guides and cheerleaders as you take on your next challenge.

Read Monisha’s starting over story

2. Embrace the opportunity for a do-over

Founder Stacey Moss inhales a fragrant roller against a botanical background
Stacey Moss, founder, Moss Botanicals

Stacey Moss grew her business steadily over the course of a decade, blending botanicals and oils to sell under her brand, Moss Botanicals. One day, a massive wildfire ripped through southern California and took her home and business with it.

The experience was devastating for Stacey, but as she processed her grief, she began to see the fire as an opportunity for a fresh start. Doubts she had about scaling her business subsided, and tasks she’d been putting off now had her attention.

She used the pause to rethink her strategy, and eventually opened her own retail store. “When I restarted, I repackaged everything with all new branding,” she says. “It’s hard to stop what you’re doing when you have a certain momentum happening, but the fire allowed me to do that.”

💡 Takeaway: On the other side of loss is a rare chance for a complete do-over. It’s an opportunity for growth and self-improvement. If you’re starting over, this is your chance to park all your “should have” and relaunch your life or business using your newfound knowledge.

Read Stacey’s starting over story

3. Get scrappy and be prepared to put in time

Founder Carl Churchill holds a coffee in a cafe setting
Carl Churchill, founder, Alpha Coffee

Carl Churchill’s life was moving in a positive direction. The US Army veteran had started his civilian career in the tech startup world. He and his family of four enjoyed a comfortable life. Then, in 2008, the stock market crashed and the company where he was working—and held shares—shut down.

Over the next couple of years, Carl sold cars, interviewed for multiple positions, and burned through the family’s retirement savings. “Sometimes we were just making minimum payments on credit cards in order to buy groceries,” he says. While he eventually found some work in mortgage brokering, the family decided to start anew with a coffee business. Carl worked full days and hustled nights from the family’s basement to get it up and running.

In the end, the long hours paid off. The family eventually opened two Alpha Coffee cafés in Utah and the business is now their full-time focus.

💡 Takeaway: Starting from nothing can help you start over because it forces you to find creative solutions to problems—and some of the most successful businesses started this way.

Read Carl’s starting over story

4. Work with what you’ve got and lean into your superpower

Founder Trisha Trout holds a mug against a brick background
Trisha Trout, founder, Prairie Sage Soaps

Until 2008, Trisha Trout had never managed any of her family’s finances. Her husband worked full time and handled the bills while Trisha worked in the home, raising the couple’s two sons. That year, though, her husband was diagnosed with cancer and passed away just months later.

The emotional stress of losing a spouse was compounded by the financial stress of losing the household breadwinner. Trisha had to learn everything from scratch, selling most of the family’s possessions to get by. But she was determined to build a new life for her family. While she didn’t have much work experience, she had been teaching herself soap making as a hobby and side gig.

Trisha turned to this hobby once again when she was starting over. The business, Prairie Sage Soap Co., afforded her the ability to learn new skills, lean into something she loved, and buy a small home for herself and her sons.

💡 Takeaway: If you’re faced with starting over, think about your unique skills or interests that could be the inspiration for a new business. Everyone has a superpower. What’s yours?

Read Trisha’s starting over story

5. Learn from your mistakes—and let them guide you

Founder Sylvia Ng lays in the grass with her two young children
Sylvia Ng, founder, Amidira, with her two sons

Sylvia Ng was a young mom and tech executive when she found out she had breast cancer. Through her recovery, she realized what was really important in her life: her family and her health. She also saw gaps in the cancer support space, inspiring her to start Amidira, a cancer-care gift-box brand.

Starting over for Sylvia also involved teaching herself to face completely new and unfamiliar business challenges. While it’s been a humbling experience, she has been able to leverage entrepreneurship to design her life around what really matters. Sylvia restarted in the aftermath of cancer not only with a new outlook, but a new career path.

💡 Takeaway: When you think you’re starting from scratch, remember that you’re smarter and stronger than you were the first time. Use your past experiences and newfound skills to guide you in the next chapter.

Read Sylvia’s starting over story

6. Remember that healing is a journey

Founder Terrell Grayson leans on a sewing machine in a studio full of bow ties
Terrell Grayson, founder, The Simple Bow

After he couldn’t find bow ties to suit his preferences, Terrell Grayson started making some himself. He turned that hobby into a business, but the dream was short-lived. “Life happened, and I was forced to stop the progress,” he says. Three tragedies struck his family over a course of three months, and Terrell lost his job, car, and home while trying to pick up the pieces and care for his sick mother.

The experience caused him to reflect on positive memories of his mother and the encouragement she gave him. He dusted off his sewing machine and picked up his old hobby again. Terrell relaunched The Simple Bow with a social mission and sells his one-of-a-kind bow ties on his website.

“Starting on this journey helped me to regain my confidence, stay motivated, and encouraged me that one day things would change for the better, if only I didn’t give up,” Terrell says. But he also acknowledges that a do-over doesn’t magically fix everything, and healing is a process.

💡 Takeaway: Be patient with yourself. Starting over can be healing in many ways, allowing you to refocus on the future. However, healing takes time, so remember to stay in touch with your mental health throughout the journey.

Read Terrell’s starting over story

Start over on your own terms

It’s never too late to start over, as these founders can attest. Whether you’re feeling stuck or burnt out and deciding to make big life changes, or a failure or tragic event has caused you to rethink your path, starting over can be a thrilling experience.

As an entrepreneur, overcoming the challenge will serve you as well as you navigate the ups and downs of being your own boss. Throughout it all, remember: take care of yourself.


Feeling inspired? Subscribe to our newsletter at the bottom of this page to get more stories like this and business resources in your inbox. And check out our mental health and wellness hub for entrepreneurs.

Feature image by Loren Blackman

About the author

pgex7

Leave a Comment