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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 unites 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 entrepreneurs that allows them to see opportunity 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 entrepreneurs 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.
How to start over in 6 steps
1. Invest in your own well-being
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 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
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 haves” 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
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
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
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
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 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
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How to Start Over FAQ
How long does it take to start over after a major setback?
There's no universal timeline—rebuilding after a major setback can take weeks for practical changes, like rebranding a business, or years for deeper emotional and career shifts. Recovery speed depends on the scale of what was lost, the support available, and how much needs to be relearned from scratch. Some people rework their plans within months, while others need much longer to develop new skills or find a new direction. Moving at a pace that fits your circumstances matters more than matching anyone else's timeline.
Is it normal to feel scared when starting over?
Yes, feeling scared when starting over is a normal response, especially after loss or failure. Taking on a new challenge while already at a low point can feel daunting, even though that discomfort often signals growth rather than danger. Naming the specific fear—rejection, financial risk, or simply the unknown—makes it easier to work through instead of avoiding it. Building a support network of mentors, friends, or a therapist eases the transition and keeps fear from stalling progress.
How do you know when it's time to start over?
It's usually time to start over when your current situation causes more stress or stagnation than change would create, or when a job loss, health crisis, or other life event forces the decision. Repeated restlessness, goals that feel stuck, or a growing gap between your daily life and your values are stronger signals than a single hard day. Trust patterns over isolated setbacks. If the same frustration keeps resurfacing despite your efforts to fix it, that repetition is usually the clearer signal to make a change.
How do you rebuild confidence after starting over?
Confidence after starting over rebuilds gradually through small, consistent wins rather than one dramatic breakthrough. Setting achievable short-term goals and tracking even minor progress creates proof that you can handle the new chapter ahead. Founders who've relaunched businesses after losing jobs, homes, or income often describe regaining confidence step by step rather than all at once, with motivation returning as momentum builds. Expecting setbacks along the way, rather than instant transformation, keeps that momentum from stalling.
How do you stay motivated during a fresh start?
Motivation during a fresh start comes from focusing on small, achievable actions instead of the total size of the challenge ahead. Reconnecting with a skill, hobby, or value you already love can turn a forced restart into something meaningful rather than purely difficult. A support network—mentors, friends, or a coach—helps sustain momentum when energy dips and doubt creeps in. Celebrating incremental progress, instead of waiting for a full turnaround, keeps the process from feeling stalled.
