Lessons Learned: My First Year of Building a Business as a Personal Stylist.

By Cheryl Nomdarkhon

I’ve had a love of fashion since I was a teenager. I grew up watching Jeanne Bekker from Fashion Television interview the original 90’s Supermodels, trailblazing designers, and household names backstage during fashion week — New York, Paris, Milan, London — every week on CityTV. 

She would have access to the most coveted runway shows, and intimate conversations with everyone and anyone in the industry. Apart from watching FT, I collected numerous fashion magazines like Mademoiselle and Glamour. I especially liked the before & after photos and fashion do’s and don’ts.  

Fast forward 25 years to March 2020, and I found myself laid off from my full-time job for a global training & development company. It was a time to reflect and reinvent myself and start over. I’d worked in several industries, from IT to health and wellness, but nothing came close to what I wanted in a truly fulfilling career. I wanted to have a real work-life balance and a job where I could make a lasting difference with people.  

“It didn’t take too long to realize that the thing that I always wanted to do was create a career in fashion — specifically personal styling.”

While I was decluttering at the start of the pandemic, I found a black and white picture of my dad in my photo album. I was struck by memories of my dad, who passed away in December 2001. It was a photo of him sitting on a bench, probably at the time when he worked for the Jamaican Customs. He sat crossed legs, his pants starched and crisp, his black shoes polished and shined. 

I remembered his clothes, his closets. He always kept his clothes in immaculate condition even though he wore a uniform to work. On his days off, he always looked sharp. When we first moved to Canada, he took us to the Eaton Centre to go shopping. It didn’t take too long to realize that the thing that I always wanted to do was create a career in fashion — specifically personal styling. My dad significantly influenced my decision to embark on my new journey.   

Getting Started as a Stylist.

Starting my business, Uncover Your Style, during the pandemic meant that marketing and networking would look very different from my past business as a holistic nutritionist ten years ago. I made it my goal to share what I was up to with the people in my life — family, friends, past work colleagues, and my connections on social media. I attended weekly networking events over Zoom and had coffee Zoom meetings with other business owners and female entrepreneurs. Last year I joined an online organization for Black stylists called Black Women Who Style. Although I’m the only member from Canada, the group’s organizer, who’s been styling for five years, is very gracious. She’s created a platform where stylists help each other, not bring each other down.  

As the pandemic meant moving back and forth between lockdowns and re-openings, the most realistic way to conduct my business was virtual. The handful of clients that I had was through word-of-mouth. To gain experience, I practiced with family and friends doing consultations over Zoom, including closet/wardrobe edits. I had a few inquiries from my website, but nothing significant.  

“How I looked and how I sounded became critically important. I never had to contend with this when I worked in the corporate world as an employee.”

I also had to learn to navigate and use social media, like Instagram. Because what I do is visual, I had to learn how to present myself to people. How I looked and how I sounded became critically important. I never had to contend with this when I worked in the corporate world as an employee. I was always the one working behind the scenes in my job. There were opportunities for me to speak in front of large groups of people and present myself as someone professional and knowledgeable, but being out there and having people ‘watch and judge you’ anywhere in the world was very unfamiliar and uncomfortable.

I’m still not 100% confident and used to putting myself out there. I sometimes overthink what I will create on Instagram and TikTok and how I come across on camera. Is what I’m presenting educational, informative, and fun? Will people get it? Imposter Syndrome comes up a lot. Another pitfall is that I automatically compare myself to other stylists and how many ‘likes’ they get and how great their content is compared to mine.

My Lessons Learned. 

One of the biggest mistakes in my first year in business was signing up to advertise for a Yelp promo account. It seemed like a good idea at the time. I registered to use several hundred dollars in (Yelp credits) to advertise personal shopping for the holiday season.  After six weeks of ad promos, there were no new clients or leads. I cancelled right away when I saw my bill the following month. Sometimes things may sound enticing, but it doesn’t automatically lead to success for your business. I learned this the hard way financially. I still get solicited to advertise, and I politely decline the offer.

I made the other mistake of saying “yes” to everybody for styling. There were times when I said yes to working with a client who was very difficult. Early indications were that the client wouldn’t be fully ‘coachable’ or agreeable, but I ignored my inner voice. I now know the importance of vetting and interviewing potential clients before we agree to work together. 

My Goals For The Future.

One of my goals for the future is to create a one-stop-shop experience for clients — like a boutique image consulting service with other stylists, designers, make-up artists, and photographers.

Sometimes, I pinch myself and wonder how I got here. I’ve spent the past 18 months hustling — giving away my time, knowledge, and expertise to get somewhere. There are many times that I’ve been disappointed about not booking that client, not getting that opportunity on a grand scale. There are also days when I feel like giving up on my dreams. The conversation in my head is that “It’s too hard, nothing is working, nobody wants what I have to give.” The biggest challenge is having that winning mindset and keeping it going, no matter what. I belong to a Mastermind group and a meditation group that helps during those difficult times.

The truth is that I haven’t yet achieved the publicity, notoriety, and good client base that I want to commit to being financially and personally fulfilled yet. I’ve created action plans and revised my business plans and goals for 2022, and I continue to plant the seeds for the next chapter — and I’m looking forward to what I will harvest in the next few months.