It was ten years ago this month that I loaded all my most essential possessions and my faithful companion Luna into my 2000 Honda Odyssey and hit the highway heading south.

Well, first I had to head north, but I’m getting ahead of myself, so let’s rewind.

This is a story that was written about me shortly after I returned from my South of the Border Odyssey. I think it gives a good preview and backstory of tales to come.

“I Wanted to See My Name on a Label”
When a Fashion Designer Follows Her Passion

“Follow your passion” is advice commonly dispensed, a trope of commencement speeches and career coaches. But what does it actually look like when someone follows a childhood dream through to a business? I sat down with Sheila Moon, the women behind her eponymous company, which specializes in women’s bike gear, to ask her about her experience doing exactly that.  

Sheila always had a clear vision: she wanted to see her name on clothing labels. She worked hard over almost fifteen years to make it happen, launching the Sheila Moon brand in 2003. Yet, recently, what was a driving passion and a successful business became overwhelming and stressful, and her passion for design seeped away. Sheila described, “This was a dream I’d had and now it’s like a really nasty divorce where everything I loved, I now hate.”

I had long known Sheila Moon the brand from when I first got into biking and coveted their beautiful gear, and was thrilled to meet the real Sheila in the flesh at a recent writing class. Sheila is energetic, with short reddish hair curling in a lively way around her face. She looks more like a yoga teacher or cyclist than a business mogul. Learning more, I become fascinated by how her passion for design turned sour.

Realizing a Dream (to be listened to)

Sheila started off by saying, “I’m an egotistical brat!” to explain her long-held desire to see her name on a fashion label. In truth, it was more than that. It was also a way for her, as the youngest with four older brothers, to gain some attention, to be listened to.  “For so many years, I had all those brothers, and they never listened. I was always just the little kid sister.  I had to work really, really hard so people would recognize me and listen to me.”

Sheila’s dream propelled her through fashion school and into a freelance business helping clients develop their patterns. For years, working to create other people’s designs, she thought to herself, ”but what about me?” She wanted to make her own designs, but either had time or money; never enough of both to launch the fashion line she dreamed of.  At one point, after she’d dealt with a particularly difficult customer, she decided it was time for her to do her own thing.  

By this time, Sheila had been a serious road biker for a while and was known in the industry. She had started making bike clothes for herself because the ones provided were utterly inadequate.  When she’d started racing for a new team, the kit they gave her included men’s chamois.  She described, “I wore this chamois for one race and thought I was going to die because my privates were so torn up.  I’m like, ‘Oh my God, how do women do this?’ “

She realized they don’t have to and started making her own designs.  The first item in her line was a pair of arm warmers. The idea came from a fashion shirt she’d designed that had one arm with a turtleneck, and an arm warmer instead of the second sleeve. The fabric was yellow with purple flowers[OU1] , and she thought her biking friends would love them. She made some and they were a big hit, so she made more.

Sheila was her own salesperson at first (a job that scared her). She would call bike stores to ask them to take a look at her clothing samples. A few agreed to buy and her business was off.  The early days were fun. She had time to really focus on designing, and also to chat with her retailers. She started displaying at trade shows. I asked Sheila if she felt the satisfaction that she’d dreamed of when she actually saw her name on labels and sponsor banners.  

“Yeah, I always felt like a rock star.”

Sheila stood out in the male-dominated bike industry, which she described as “all steel and carbon and really sleek.” She made it a point to be different, and play up the femininity of her brand. She described her booths at tradeshows as “just a mess of fluff” staffed by sexy women that actually worked for her. People would be walking through the tradeshow, eyes glazed over, and would be startled seeing her booth.

“It was so much fun to be recognized for what I did, to really stand out and be different.”

Getting Thrown Out of Balance

As the business grew, making sure that goods shipped on time became a bigger and bigger responsibility. Sheila struggled to balance work and taking time for herself.  She had wanted to grow her business enough to free her from some of this responsibility.  This required bringing on a production manager– a role that never worked out. “I’m not a good manager,” Sheila confessed, “It was hard to learn about myself.”  

Though Sheila received a lot of qualified applicants for a high-level management position, Sheila lacked the confidence in her business to bring on someone that seemed overqualified. She thought, “Why would they want to be stuck in my piddly little business?” Sheila settled for someone who ultimately wasn’t the best person for the job.  “I was afraid of giving away control over my business,” she admitted.

Sheila didn’t have a business background (she’d actually started out as a business major in college, but quickly switched to history and journalism:advertising). To learn more, she took advantage of financial advice from organizations that help small and women-owned businesses. It was talking to a financial adviser that she realized what her next step would be.

Walking Away

By this point, almost ten years after she first launched, Sheila was unhappy. What had been year-over-year growth for the Sheila Moon brand had started to decline, compounded by a few difficult employees. And she was taking it all personally. Because it was her business and her name on the labels, Sheila felt the weight of it all on her shoulders.

Sheila was struggling to figure out what to do next when she met with an advisor who asked her, “Did you ever just think about selling your business and just walking away?” Sheila was stunned; it felt incredible. She thought, “I could do that?!” By the time she left the advisor’s office, she was already making plans how she could leave.

Sheila felt completely done with her business by then, so she filled outstanding orders and drove south, spending a year traveling around Central America. She did exactly what she wanted: hanging out on beaches, going for long walks with her dog, Luna, traveling where she wanted and meeting new people.

This time, coupled with her dad’s death the same year, was a fundamental shift for her.  Since her return from Central America, she’s tried to continue to prioritize things that excite her.

“I think the biggest thing I learned from running my business, and getting away from it, is that it’s really, really important to live and enjoy yourself.”

The Demise of THE Sheila Moon

I asked Sheila how it felt to give up the Sheila Moon Brand: “Most of the time, it feels awesome. One thing that was happening was that I wasn’t Sheila Moon.  I was The Sheila Moon. I was a brand, not a person.” Though in the beginning, she loved the recognition that came with it, the identity became too much responsibility as the business started to decline.

It’s been hard for Sheila to tell people that she’s closing down the brand; she hasn’t made a formal announcement yet. It hits a deep nerve to lose something that she has loved for so long.  She described how she had loved sewing from the age of five, “I want to get back,” she said. “I would like to still have my passion for designing. Every once in a while, I get a little hint of it, but not much. I’m not quite ready to give it up.”

Giving up also means a final ending; it would mean that the business failed.  She can’t help but compare herself to others that started successful businesses around the same time. It’s hard for her to remember that she created a whole business out of nothing; she feels like a failure.

Finding her Next Passion

Yet, when I look at Sheila, who is lively and energetic, I don’t see a failure at all. I see someone who has followed her passion with both courage and intelligence. She took big risks to build the Sheila Moon brand into what it was, and worked hard to make it happen.  It also takes a whole lot of courage to admit that it is no longer working. Sheila is finding new passions, like writing mystery novels set in Central America, and I can’t wait to see what comes next for her.

I couldn’t help but ask– what would she advise someone else? Should they follow their passion, thinking about how hers has ended?

“If I hadn’t followed my passion I would probably still have my passion for sewing and designing. But I know myself, and these past 25 years, I would have been completely frustrated because I was not doing what I loved to do and I hadn’t tested myself.  So, yes, follow your passion. It’s the most amazing thing in the world to be doing what you love.”

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