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My Starting Over Story: How I Revisited a Passion Project During My Lowest Point

Portrait of Terrell Grayson collaged over a pattern of bowties on a green background

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. 


Over the course of Terrell Grayson’s career, he wielded his talents across many industries and jobs, from performing as a voice actor to working as a chef and catering manager. Interested in entrepreneurship as his next move, he decided to transform a passion project into a business. 

But then tragedy struck his family and the resulting events derailed Terrell's plans. He became his sick mother’s caregiver and lost everything he had—his job, his car, his home. The experience caused him to reflect on the oft-repeated words of encouragement his mother had given him since he was a child.

Galvanized, Terrell returned to his dream and, in the midst of the lowest period of his life, launched The Simple Bow, making and selling handcrafted one-of-a-kind bow ties, and donating a portion of the profits to causes close to his heart.

This is Terrell’s story, in his own words:

The idea for my business started in 2008, when I decided I wanted to turn a hobby into a business. I started working on a plan, creating a design I couldn’t find for myself in the industry. I purchased some materials and did some research that would help me reach my goal of continuing as a successful entrepreneur. 

But life happened, and I was forced to stop the progress.

Then, over the course of three months, my mother, who has both lupus and a rare Stage 4 cancer, was hospitalized, my fiancé was shot, and my grandparents were in a severe head-on collision. Neither grandparent made it out of the hospital alive. 

This all happened in 2019. That fact that I seemed to be losing control of everything that mattered most in my life caused me to feel worried and stressed. I felt anxiety and depression come over me. I was unable to speak and think clearly and started losing confidence in myself and my abilities. For a while, I became a man that I didn’t recognize.

In a time when I seemed to be nearly losing all hope, I recalled something my mother used to say to raise my spirits: “You’re an intelligent young man. Just put a bow on it, and make it look nice.” That memory, paired with the old sewing machine found in her basement, led to the creation of The Simple Bow.

Terrell Grayson sits at a sewing machine with an array of bowties spread out before him
Terrell Grayson, The Simple Bow

The most challenging part was attempting to pick up where I left off in the midst of family turmoil. I didn’t have a knowledgeable mentor familiar with business in the fashion industry, and I was just going blindly ahead with nothing more than passion, a dream, and the desire to help get my family out of homelessness.

Starting a business can be a lonely journey. From the outside looking in, people made me feel like a failure, and that what I was doing was something so small and meaningless, when in fact, it is a job times 10 plus 1. Starting this business helped me to regain my confidence and stay motivated, and made me hope that one day things would change for the better, if only I pressed on and didn’t give up. It helped me in many ways, but the truth is that I’m still healing, because we are not out of the woods quite yet.

Starting this business helped me to regain my confidence, and stay motivated and encouraged that one day things would change for the better, if only I pressed on and didn’t give up.

In starting over, I learned that sometimes you have to do what you may not want to do, to get to where you want to be. For a while I felt that I had failed myself and my family, but I realized that this was just a new opportunity for me to gain the confidence to take the road less traveled.

What would I tell someone else in my shoes? Live each day as if tomorrow will never happen, because we never know what the next day will bring.


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Feature image by Loren Blackman