PERSONAL ESSAY

Taking the leap to be my own boss — even more unapologetically Black and free

On the African American anxiety of entrepreneurship and creating our own tables instead of fighting for a seat

By Takirra Winfield Dixon

Published June 12, 2021 6:30PM (EDT)

Takirra Winfield Dixon (Photo illustration by Salon / images provided by author)
Takirra Winfield Dixon (Photo illustration by Salon / images provided by author)

"Is now the time to do this?"

That's what a former colleague said when I told her I was ready to leave my job.  

It was my last day of work. I was relieved and anxious all at once. I just had to wrap up some last tasks, one last meeting, and then I would be on my way. 

Saying goodbye during the pandemic is weird because there are no farewell lunches or happy hours in person, no people walking into your office to chat one last time as colleagues, no parting gifts left on your desk, no notes left on your bulletin board. It wasn't a normal ending at all, just a lot of time to think and reflect between Zoom meetings. Instead of the usual goodbyes, I opted to have a small, light-hearted virtual gathering with my team and to send a note to our board and staff in my I'm-here-to-push-boundaries-and-make-you-uncomfortable-while-celebrating-my-Blackness way with the subject: "The Next Chapter: Unapologetically Black & Free." It was time to go.

Instead of packing up my office, I clicked the red "x" at the left-hand corner of my Zoom, closed my laptop, and turned off my work phone for the very last time. I popped a bottle of champagne, and waited for my husband to come home so we could breathe a collective sigh of relief. But the words I wrote in my farewell note are incredibly true. I wasn't just moving onto the next job. I was actually free. April 16 was also my last day of working for other people and the beginning of working for myself. 

In December of last year, I started to reflect on what I wanted to do with my career and it led me back to growing up in Baltimore, a Black girl with natural hair and dreams. My mom was the unsung hero of our family, making the choice to stay home to care for my brothers and me. She was my first example of what a Black woman could accomplish and I admired her sacrifice. My mom told me that early in her career, positions like secretary were the only jobs available for Black women. At one of the places she worked, she was the only Black secretary and was forced to sit at the back of the office while all the white women with the same qualifications and the same responsibilities were allowed to sit up front. Mom told me, "White folks didn't want to see Black faces when they walked in the door." When she would go to turn in her work, her white boss wouldn't even look at her: "She never acknowledged me or made eye contact because she didn't see my humanity." 

My grandmother and other Black women in our family had little choice but to work for years cooking and cleaning for white families in Virginia. My grandmother was the best cook — she made everything from fried chicken to chocolate cake to fresh buttered rolls. As a girl, when I would visit her, I used to help her in the kitchen making dough and waiting anxiously by the oven so I could taste one of her rolls. Her kitchen was warm, quaint and inviting. You could smell whatever she cooked throughout her entire one-level house. I can still hear her singing "For Your Love" to me and asking me to get ingredients off the shelf so we could make recipes from the green book of goodness she kept in the kitchen cabinet. 

As I grew up, I often heard people tell her, "Maude, you should've opened up a bakery or a restaurant!" Those statements weren't just compliments. They masked a lifetime of missed opportunities she was never given to begin with because her talents were relegated to someone else's kitchen instead of her own. As a Black woman in the South, this was out of the realm of possibility and laced in cloaks of discrimination. 

Because the Black women in my family had such limited opportunities and experienced racism, my mom raised me to be the most ambitious, strong, confident, questioning Black girl. She clothed me in a cape of possibility that slipped through the women's hands before me, and surrounded me with examples of Black excellence. I had Black dolls and I also had people I thought of as real-life Black superheroes, including a Black pediatrician, Dr. Lunis. Dr. Lunis was friendly, warm, honest, and he listened when I was scared. He'd tell me, "You're gonna be OK." I believed him because he cared. And then there was Debi Thomas, the most accomplished American figure skater in Black history. I used to sit on the edge of my parents' bed, probably a little too close to the TV, with my feet dangling off the front of the mattress waiting for Debi to come on and perform her jumps. Debi was beautiful. Her talent was as amazing as her outfits. She confidently glided on the ice like an angel, and she was Black. 

Dr. Lunis and Debi showed me what was possible. So one day, with all my Black girl superhero-ness, I said to my parents, "I want to be a doctor and an ice-skater when I grow up!" The look on their faces felt like, "What just happened?" I could tell even as a kid they didn't want to crush my dreams. In the gentlest manner, they tried to explain why this would not be possible: "Don't you just want to be a doctor?" 

Throughout my career, I have taken that confident little Black girl with me, determined to get to the top of the game in whatever job I had. In high school, my first job was at the Maryland Science Center working in the interactive space exhibit. I went in early, stayed late and learned everything I could. I wanted to be the perfect employee, memorizing space facts so I didn't need notes to help visitors. And I was rewarded — compliments from managers and colleagues, free tickets for family and friends. People really seemed to respect my work ethic. Being a "good" employee was how I approached every job since. Job after job, this behavior was rewarded with accolades. Then came the promotions and the money: I remember getting a note from a boss who said I was the best employee he had ever worked with and he hoped I would stay onboard to continue making great progress for the organization. He knew I was on track make it. 

In the months before I left my very last job, I was feeling uneasy, unmotivated, a little sad, and approaching projects in a robotic way. My check-ins became routine: "How are you? What are your wins today?" Here's the next 50 projects coming down the pike. It felt like there was no end in sight. I was tired of being plugged into someone else's goals. My mom often said, "Make sure you have a job lined up before you go to the next one." This time there was no next job.

I made the decision not to take a leap of faith, but to just leap. I no longer wanted to be defined by what I did but rather who I am. What if my mom and my grandmother could have done the same? 

Once I made my decision to leave, I just wanted to move on. But older Black women wouldn't let me. Every conversation I had with them was like a dissertation defense of how I was going to be OK. Two older Black women with whom I worked wondered why I would dare leave the system I had been able to navigate so well. One of them, clearly signaling I wasn't in my right mind, said: "Wouldn't you rather just stay at your job? It's a pandemic and jobs like you have don't come so easily. Why give it all up?" The other just simply replied to an email I sent giving her a heads up: "Good luck." She just knew I was going to need it. 

For Black women, walking away from a job is a freefall of unknowns we imagine might destroy us and disrupt our lives. It's the type of risk that feels impossible; the type of risk that never allowed my grandmother to own a business. That I chose potential disruption is a foreign concept when stability was the only choice for Black women who worked hard to attain it in workplaces where we weren't respected or even allowed in the first place. 

The Black women before me couldn't have imagined that I'd work in the administration of the nation's first Black president. I loved serving with President and Mrs. Obama, and every day I would get reminders from family, acquaintances and friends, and former colleagues and bosses that I had truly made it. I remember my husband's family coming to our house and being awestruck by photos on the mantel of me at the White House Holiday party with whatever celebrity I'd met, or with high-ranking cabinet officials, and even a few with the Obamas. When she saw my signed copy of "Becoming," my husband's cousin said, "Well, you don't need to do anything else; my cousin knows the Obamas!"

But when the administration ended, I watched several white men who had also served with me take months-long vacations and then launch their own firms using money they had saved, were given, or had invested. I did not have that luxury. I wished I could have launched my firm then, but I was scared to death to walk from stability. I put my dream on hold, packed up my office and headed to the next job. Recently, I called a white colleague who also owns a communications firm to give him a heads-up about my intent to launch my own. Before I could get any words out, he actually said to me, "I hope you're calling me to tell me you're coming to take your talents to my firm." He preferred that I work for him instead of working for myself, much like the white families my grandmother worked for preferred her to cook and clean for them.

After a long pause, I told him my news. "Actually, I'm launching my own firm." His silence was deafening. I knew he feared my freedom. 

I told a close friend about my dream. She said, "Don't you want to wait it out until it's safe?"

"Safe?!" I said. "It's never safe for a Black woman in America!"

She supported me, but wondered if America would protect me. And I sobbed after we talked. She had hit on my darkest fears — that I wouldn't make it on my own. Deep down, I feared that I would let myself down, my mother down, my grandmother down, our ancestors down. 

Our social systems are often built to kick Black women and then designed to kick us again when we're down. Just the thought of having to file official paperwork was overwhelming. This was all foreign. I called a friend who had also gone out on his own and I asked him what I should do. He guided me and connected me to his tax attorney. I was anxious as I set up that first call. The attorney assured me everything would be fine and he walked me through all the steps needed to start my business. I listened. I took notes. I was still scared. I had heard horror stories from other Black business owners about being in the system. 

And then one of those missteps came true. After we submitted the paperwork, we learned they left the "s" off the end of the name of my firm. It happened; I got kicked. I was in a full-blown panic. This may sound silly to some, but being a Black woman stuck in government systems means that we're dead last on the list to get simple things like corrections done. And then the attorney called me. "We'll get this corrected," he said. "I know the paperwork to file."

When all the paperwork was finally cleared and right, I had a feeling of pride and self-worth I had never felt before. I started working on my website, my logo and all the legal to-dos. And I chose incredible Black people and Black businesses to help me do it all. 

A couple of days later, I picked my mom up to take her to an appointment. My heart was beating fast. I waited until we got to the first traffic light and told her my news.

"Well, mom, I'm a business owner now. I filed paperwork the other day and it's official."

She seemed worried at first, and proceeded to ask me questions about the business to make sure I'd be OK. Then she said, "Well, you know what you're doing, and I support you."

I knew then I had made the right decision. I'm so grateful that she put Black role models in front of me, but she will always be the first. 

I announced this new venture in February on the anniversary of the day my grandmother passed, while I was still protected by the shelter of my job. There was no way to know how people would respond. Then one by one, the clients started to come. Someone even asked to work for the firm before I could officially sign my first client. My idea and my abilities were validated in a way that moved me from having a job to being a founder. I chose the title "founder" intentionally because I do not want to ascribe to mostly white norms as a CEO or a president or an executive director.

I built my own table. On April 16, I walked away from stability. I thought about my grandmother and if she were alive today, how proud she'd be. I thought about all of the people who told me it wasn't the time, and decided it was my time. 

Today, I couldn't be happier. I wake up every morning and want to work hard for my clients. Many of them are Black women leaders and visionaries working for justice. I see their potential. They inspire me. Sometimes our meetings are like Black girl therapy. My clients often come to me exhausted from the aggressions they've dealt with in a day, and before we get to work, we talk in a safe space about what it's like to be a Black woman. Then, I gently nudge them to channel their feelings into a courageous speech or commentary or interview. A client recently thanked me for helping her find her true voice. Another client has spoken up publicly about her personal story for the first time. My first hire was a Black woman colleague that I refuse to call an "assistant" because she is powerful in her own right. And sometimes, my Black women clients are referring me to other Black women clients and we are in a world of possibility in a world that won't see us. Together, we are walking away from white supremacist capitalism and entering into an ecosystem of our own. There is nothing like it. They are my Black superheroes now. 

Some days the work is really hard, but it is no less gratifying. At times, I am overwhelmed when all the client deadlines seem to run together or when I have to say "no" to a potential client. Sure, I may encounter tough times in this new chapter, but I would never forgive myself if I didn't at least try. There is a chance I could lose everything. I don't have a trust fund or a silver spoon of wealth to fall back on. My home is likely my greatest financial asset and realistically, the bank owns that. My savings could be depleted because of an emergency. Or I could hit a lull in business due to circumstances beyond my control. But honestly, I'd rather be forced to fold up my own table than leave the one someone else built. 

In the future, I never want to lose sight of the brave feeling I had when I took my first client meetings. I want to always remember the original clients who bring me joy every day. I hope that together, we can build a movement that centers our stories and our mothers and grandmothers and ancestors who couldn't have imagined our tables. For those who worried about me in this journey, thank you for your concern. I'm still here. I'm on my own — in a freefall of my choosing, making of the world whatever I damn well please. Unapologetically a Black woman and free.  


Takirra Winfield Dixon

Takirra Winfield Dixon is a Baltimore native, activist and former Obama administration official. She is also the founder of Unapologetic Communications

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