Riding the Rollercoaster: The Thrills (and Challenges) of Full-Time Freelancing and Entrepreneurship

My inner child is constantly in awe, filled with both excitement and confusion by the interesting career path I chose.

Fashion has always been my thing, but my earliest career aspiration was to become a hairstylist. I grew up in Philadelphia, raised by my amazing Mom, and going with her to Germantown Avenue to get her chic, short haircuts was a ritual. From the buzzing of hair clippers to the scent of the curling iron and the snipping sounds of hair scissors, I absorbed everything around me. I’d sit on the sticky, black leather couch, thumbing through magazines like Hype Hair, Essence, and Black Hair, noticing the men who entered the shop selling bootleg DVDs. But what interested me the most was the limitless creativity on display: women of all skin shades and hair lengths with renewed confidence adorned with fresh hairstyles.

Through these experiences, little Amirah witnessed Black people expressing creativity and building community. It was a world where beauty wasn’t just skin deep but a catalyst for conversations about fashion, music, and the essence of womanhood. Inspired by my childhood friend's ability to braid hair, I convinced my mom to purchase me a human hair mannequin from the beauty supply store. For hours, I’d experiment with braiding techniques, mastering intricate styles like zig zags and crisscrosses (with Allen Iverson’s iconic presence playing for the 76ers as more motivation).  

Though I am not a hair stylist now, I still enjoy trying new styles on my hair. I've been entrenched in the fashion industry for the past eight years (eleven, if we include my time in retail). As a child, the notion of business ownership never crossed my mind. In my early twenties, after graduating college and moving to NYC, I quickly realized working a traditional 9 to 5 was not for me. Legendary figures like Misa Hylton and June Ambrose, fashion stylists, and creative masterminds responsible for iconic looks sported by my favorite artists, Lil’ Kim, Busta Rhymes, and Missy Elliott, served as my inspiration. Their ability to create art through fashion was a path I wanted to be a part of, but I was unsure how to walk down that path. As a fashion stylist, I’m grateful they paved the way for me and many others. 

Since 2019, I have been a full-time entrepreneur and freelancer. Unlike many people with a safety net of savings set aside to venture out into the unknown, my journey looked different; mine may not be suitable for everyone, but it worked out for me. Despite growing from an intern in 2016 to building my knowledge as an assistant stylist for years, I still worked part-time as a retail store manager in Downtown Brooklyn. Though the stability of a steady paycheck was tempting, my heart yearned to check in photos of looks, be on set, and even wrap up cool projects. Balancing both worlds became increasingly challenging, as I either turned down exciting projects to work at the store or called out of work to assist on projects. There was also an added burden at the retail store, with a prejudiced manager above me who consistently made it her business to demean the Black managers and employees. Her manager and H.R. ignored our constant concerns.

 Breaking free from this toxic environment and pursuing my dreams was a clear choice. With unwavering determination, I jumped off the porch and embraced the life I had dreamed of. Saying this journey of entrepreneurship and freelancing is consistently easy and breezy would be far from the truth. While undeniably beautiful and gratifying, it’s more equivalent to a rollercoaster ride with sunny days and cloudy ones alternating unpredictably. Loads of thrills and lots of challenges are the reality for any entrepreneur or freelancer, and I have six experiences that I’ll dive into.

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1. “TO FREEDOM”- I wouldn’t be surprised if autonomy is a primary driving force behind many people opting to become self-employed. But before I get any deeper, let me address an actual reality: transitioning from a traditional 9 to 5 to the world of entrepreneurship or freelancing can sometimes mean trading set work hours to having little to no healthy balance between work and your personal life. Entrepreneurship can turn into a 24/7 commitment if you let it. In my case, the nature of my styling work usually demands long hours, but I choose what projects I want to work on. As a storyteller and freelance writer, I meticulously proofread my words. My passion project, CreatedbyUs., is a directory for people to stay connected with and shop from hundreds of Black businesses. I spend hours updating the site and creating content weekly.

   

   I find joy in dictating my schedule. It’s a freedom that allows me to tune into my body’s needs, heed my intuition, and prioritize accordingly. Also, I believe our bodies correlate with the planets, hence why many people have a hard time working on Mondays, the day of the week that the Moon rules; that’s a topic I’ll save for another time. The ability to shape my day according to my rhythms, take a nap at random, spend the day with loved ones, or decide to tackle my emails is invaluable to me. 

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2. Net 30, 60, and Beyond - Who enjoys waiting a month, two months, and even sometimes four months to receive payment for a project long since completed? * cues crickets * Absolutely no one. I had never encountered the agonizing concept of “net 30” payment terms until I started in fashion. Silly of me, I thought compensation would follow swiftly after completing a project. Whew, was I in for a rude awakening? It’s truly the bane of many freelancers' existence. There have been instances where invoices totaling thousands of dollars lingered unpaid, leaving my bank account as dry as a desert thanks to the bills that snatched my coins like a thief in the night. Yet, I still needed to wait a few more weeks to receive payments. Now, close your eyes and imagine seeing a campaign you worked on go live on Instagram while the money for your art, time, and work is elusive. 

   

   In response to this persistent issue, I've implemented late fees, only to find that some brands completely disregard the bold red print on my invoices and still pay at leisure. For specific projects, I secure a fifty percent deposit upfront and receive the balance within a week of completion. There are quite a few things within the fashion industry that I’d like demolished, and “net 30” payment terms are very high on my list.

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3. Connecting and Creating with Other Passionately Talented People - Group projects dominated my coursework during college, and I was not a fan. I preferred the solo route regarding academic or professional tasks, ensuring deadlines were met and outcomes matched my visions. My professors often emphasized the importance of collaboration in the fashion industry. Nowadays, I constantly find myself connecting, meeting, creating, and working with highly talented individuals. The beauty of this is that everyone brings their unique passion and perspective to creating art, improving the creative process in a way I couldn’t do alone. I’m blessed to forge meaningful work relationships and see our art come to life unimaginably. 

   

   In 2016, while interning, the lead stylist told me another intern would meet with me to pick up clothing for the shoot we were working on. Jazmine, the other intern, showed up and was so friendly! We started talking about our shared experiences within the fashion industry, our backgrounds, and where we were from. Lo and behold, we lived only a few blocks away! Since that day, our friendship has extended past styling, and I’m grateful. We’ve worked on multiple projects together, creating art that’s landed on the cover of magazines. We’ve also celebrated birthdays, major life events, and more together.

   As an entrepreneur, the avenues to meet someone are countless. Whether it’s striking up conversations with strangers on the train, at a coffee shop, or chatting with someone while standing in the Trader Joe’s checkout line, every interaction you encounter can turn into something meaningful. Even if it doesn’t, that’s okay too. I’m big on putting people I know into opportunities that greatly benefit them, their career/business, and their pockets.

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4. Slow Weeks and Months - I was naive in the early stages of my styling career, believing that ascending the different tiers would guarantee a steady stream of exciting projects. I was wrong. The past year and a half has been a stark reminder, apparent to anyone who has glanced at grocery prices, inspected the interest rates on credit cards, or even grappled with the soaring cost of living within the U.S.; inflation is no joke. Not only does inflation affect what I just mentioned, but it also affects jobs, including the livelihood of entrepreneurs and freelancers. 

   As inflation stubbornly (I wonder if it’s an Aquarius) stays stuck around that mid-3% range, businesses scramble to grow their net profit. To do that, they reduce costs, with Marketing usually being the first department; any creative title, but especially styling, will feel this tremendously because while I strive to make the talent in a campaign, commercial, or photoshoot look oh-so-fabulous, the number of projects slowly dwindle, the budgets presented to me become laughable yet concerning because hiring and paying me isn't the brand's priority.

   

   The middle of the summer, when vacationers are basking in the summer sun, and the beginning of winter, when families are joyously spending holidays together, is the most sluggish period because the projects take a backseat. I’ve been diversifying my focus to include personal styling because you must wear clothes, no matter the season. I’ve also embraced the downtime to collaborate on test shoots and execute passion projects I couldn’t focus on during my busier moments. I’ve accepted that the slow days, weeks, and months don’t feel good but are inevitable.

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5. See Ideas Come to Life - One of the most heartwarming feelings is when someone entrusts you with their vision, believing in your talent and expertise to bring it to fruition. I’ve been asked to write the bio and other informational wording on entrepreneurs' websites. It means a lot to me that my writing style resonates deeply enough for them to want to share it with their core audience. Through the journey of personal styling, being of service takes center stage. I am privileged to guide them toward clothing, footwear, accessories, or even a new sense of style. While it’s effortless to conceptualize outfits browsing on a website or from racks at your favorite store, the magic unfolds when you see it all come together on a model, a talent, or a client. Everyone involved radiates joy. Walking away from a project, knowing every fiber of your being was poured into it, ensuring its success, is an unparalleled feeling.

   

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6. H.R., Marketing, You are Everything in Between - This experience is more relevant to entrepreneurs and freelancers who haven’t assembled an entire team yet. As mentioned, I am grateful to be on this journey, creating my own path and paving the way for future generations. However, without a team, one instantly becomes a Jane/Jack-of-all-trades, not by choice but by necessity. You morph into H.R., addressing issues when they arise, maintaining a delicate balance between respect and protecting your ass. For businesses with a social media presence, a substantial chunk of time is allocated to creating content that engages your audience and brings in more revenue. This relentless pursuit can easily leave you vulnerable to burnout; it’s exhausting.

   

   Mastering the art of delegation is a game-changer for entrepreneurs and freelancers. I’ve found it helpful to refine my to-do list and planning regimen. Getting clear on what tasks require immediate attention versus those of lesser urgency is a potent antidote to mental clutter and stress. By discerning priorities, we can alleviate the burden and navigate the entrepreneurship landscape more easily.

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   Becoming your own boss may sound glamorous, but it’s far from a walk in the park; it's more like a rollercoaster ride filled with peaks and valleys. Taking this leap of faith has been among the most rewarding decisions ever. I know little, teenage, and twenties Amirah is constantly amazed by everything I’m doing today and how it aligns with my visions back then. Reflecting on my experiences stepping out as a full-time entrepreneur and freelancer, I could have easily recounted thirty more. But I’ve chosen to share these because they’ve left the deepest imprint on me thus far. These raw and pivotal experiences have helped shape my journey and taught me lessons I’ll hold near and dear to my heart forever. 

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   ~ If you’d like to send a couple of dollars for 🫖 or ☕️ while I’m sitting at the coffeeshop writing these essays or working on fashion projects: Buy Me A Tea/Coffee