Self-employment is something many people prefer or aspire to, as being your own boss is both admirable and empowering. And women are bossing up more than ever, representing almost 40% of all self-employed professionals. Being self-employed myself, I can attest to the benefits, but like everything in life, there are two dueling sides to every coin. And if you're considering taking the leap from 9-to-5er to self-employed, there's a lot to consider before totally pulling the plug on your day job.
Here are a few things to know, from my own experience, before transitioning into self-employment:
1. Recognize that self-employment is not entrepreneurship.
There are key differences between being an entrepreneur and being self-employed that many people get all mixed up and confused about. The terms are often used interchangeably, but they are definitely not the same.
A self-employed person operates just like an employee, often offering services and talents to business owners, nonprofits, or organizations. An entrepreneur typically offers goods and services to a client or customer, registers their business for tax purposes, and can reap the benefits of resources like business bank accounts, financing, and investments.
When you're self-employed, you often don't get paid if you don't work, most typically as a freelancer or on a project-by-project or client-by-client basis. When you're an entrepreneur, you can successfully scale a business where you can reap the benefits whether you're actively working in it or not.
You can indeed launch a one-person business (i.e., as a limited liability company or LLC), but there are requirements related to that, particularly when it comes to taxes. There are also things to consider, such as lifestyle, goals, and risk tolerance. The annual and financial obligations entrepreneurs have aren't the same as self-employed professionals, like additional taxes, filing fees, and mandatory financial reports.
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(I know some of y'all entrepreneurs might be reading this with a side-eye, but hey, not every self-employed person is a business person, and some simply might not want the extra maintenance and responsibilities of having a registered business, no matter the perks.)
While I'm not discouraging any self-employed person from launching a business, knowing the difference between the two is important because it sets the tone for how you approach the work that you do, your expectations on the lifestyle and requirements, and what benefits might be afforded to you.
Many entrepreneurs can employ people, scale their businesses for expansion, get capital investment, and even take days, weeks, or months off without having to actually work yet still reap the benefits. This is often not the case for a self-employed person whose salary largely depends on actual work hours, paid invoices, and strategic budgeting.
2. Inform yourself about the tax obligations and other financial shifts that might happen once you are self-employed.
When you're working a 9-to-5, your company handles taking taxes out of each check. This is not the case for self-employed folk. There's a quarterly schedule that must be followed for federal taxes, and there are other regulations based on the state where you primarily work (even if you're working remote). If you're used to having a hands-off approach to taxes (other than going to the tax preparer once a year), you definitely want to shift your expectations and get to know all the information you can about self-employment taxes.
Also, the way you budget might be a bit different when you're self-employed. If you find, for example, that you're constantly living check to check or that you're used to a guaranteed paycheck every two weeks, you'll need to shift the way you look at how money flows in your household.
Self-employment can include periods where you're not getting paid as consistently, and many companies work with invoices that are paid 30, 60, or even 90 days after you've finished the work you've done for them. Keep this in mind and plan accordingly based on the industry you'll be working within.
Talk to a tax or personal finance professional to find out about how your finances and tax obligation might change once you decide to become self-employed, and then set up a plan so that you won't get caught slipping come Tax Day. The process is different for self-employed people, and this is an important aspect of the process that will save you lots of money and stress in the long run.
I learned the hard way to negotiate, upfront, a set period of time for my services (when applicable and reasonable) to be written into a contract and to set my rates not solely based on my previous salary but considering additional costs like WIFI, travel, health insurance that I have to pay for out-of-pocket, home office technology and tools, and the time it actually takes to complete tasks. The pandemic brought home how super-important this was because, as a freelancer, someone can simply cut you with no compensation or warning.
3. Get to know your true strengths and weaknesses when it comes to work ethic, skills, environment, and motivation.
Self-employment is definitely not for the faint at heart. It can be a constant hustle in the beginning, and if you're not careful, you might end up wondering how you'll pay your rent or car note simply because you don't have clients or work lined up. It's good to be a self-starter and super-organized. It's also good to brush up on your marketing, communications, and sales skills because you'll need to pitch yourself and your background in order to land projects and clients.
While working your full-time job, take a few courses or find a self-employed mentor so that you can strengthen your skills in areas where you might need some improvement (i.e., pitching, online marketing, social media branding, or project management.) Practice self-employment on the side as an intern or with a side hustle so you can learn a bit more about yourself that you might be overlooking while serving as an employee.
Being self-employed means you become multiple departments in one person. For example, your current company provides support like assistants, accounting departments, legal teams, and IT, so you might not be used to having to handle all of those things on your own. For some, this can be overwhelming, while others find the challenge invigorating and worth the sacrifice if it means having autonomy and financial and time freedom.
Also, if you're motivated to do your best by being around teams or working in an office, self-employment might be too isolating for you. True, there are groups and co-working cultures you can join, but it's definitely not the same as having built-in comradery of fellow full-timers at a company. Be aware of these things so that you're realistically making a choice that suits the life you want to live and the work experience you want to have in order to thrive.
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4. Create an emergency fund solely for the transition.
While you're working a 9-to-5, create a separate savings account just for the transition. Anything can happen between quitting your job and getting your first freelance gig, client, or project. When I first stepped out to be self-employed, I thought I had the dream client, only to find out that it wasn't a good fit and I'd be looking for a new one after six months. This might happen several times before you really hit a groove, find your fit, build up your reputation, and get consistent work.
Having a financial cushion outside of your usual emergency fund helps to soften the blow if something like a client loss, a late invoice payment, or an unexpected work-related expense (i.e., computer replacement or broken equipment repair) comes up.
Sometimes, self-employment can include certain up-front costs like renting an office space, investing in new technology or other tools, travel expenses, or hiring other self-employed professionals (i.e., a consultant, web designer, or tax preparer), so you'll want to be smart, be prepared, and keep your receipts.
5. Understand your why.
Every great and sustainable journey starts with a good reason---a "why" that keeps a person going. If you know your why, you're less likely to just give up when things get rough, and you're less likely to make costly, mentally and physically draining mistakes. I decided to go for full-time self-employment because, after more than a decade working in my field, I really felt burned out at the time, began to resent not being promoted as quickly as I thought I should, and saw that I could make more money contracting my skills and talents out than working full-time for one company.
I also loved that I could pick and choose who I worked with and align my values with the projects that I was part of (versus being forced due to being a full-time employee beholden to a contract and the so-called values of a corporation or company.)
I've made quite a few mistakes over the years, but my why remains the same, and when times get hard, I simply remember the overall peace, flexibility, and autonomy I have in serving the women millennial audiences I want to serve through journalism and communications.
6. Be sure that you're offering services or expertise that can be used for years to come and that's competitive.
If you're considering self-employment, be sure your skills are competitive and have a future of need. I knew, even a decade ago, that much of the media industry was going the freelance route, and today, with layoffs becoming commonplace and full-time employee budgets being cut, contract work has become the name of the game. I saw this industry shift coming a mile away, and, like my early foray into digital media before publishing houses were monetizing it, I knew eventually, freelance work would be abundant and preferred.
If you're already doing a job that is in high demand or you offer something niche and one-of-a-kind, working for yourself might be the move. But if you've found that your current skills might be obsolete in the next two to five years, try learning another skill, shifting how you do the work you do, or tapping into another passion that can ensure you're offering something valuable in a market where it's direly needed.
Self-employment can be a joy and a pain, and for many of us, it's the only choice for self-care, mental wellness, and financial freedom. If you're considering taking the leap, take into account these tips and go forward in bold confidence, informed, and prepared.
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A Goddard College graduate, who earned an MFA from Pratt Institute and was awarded an honorary doctorate from Marymount Manhattan College, Mahogany offers unapologetic realness with a side of grace and empowerment. "I started touring locally. I started creating chat books so that those poems will go in the hands of the people who were sitting in the rooms," she shared.
"And then I started facilitating poetry workshops, so I used my chat books as curriculum. And that, in turn, allowed me to further invest in my art and show the community and people who were hiring me that it wasn't just a one-off, that it's not just, you know, a fly by night—that I am invested in this art as much as I am invested in your community, in your children's learning, in our growth."
Mahogany has a special way of moving audiences, and her superpower sparks shifts in perspective, post-performance introspection, and strengthening of community bonds, especially among Black women. (One can undeniably recognize her gift for arousal of the spirit and mind merely from her listening to her insights from the other side of a Google Hangout call. I can only imagine the soul-stirring, top-tier sensory encounter when watching her perform in person.)
In this chat with xoNecole, Mahogany reflects on sustaining a creative career, the aftermath of writing a banned book, and using poetry for both healing, community-building, and activism.
Anthony Artis
xoNecole: What are three key things that have laid the foundation for a sustainable creative career for you?
Mahogany L Browne: What has helped me is that I'm willing to go in being an expert at knowing poetry and knowing the way in which art can change the landscape of our lives, not just as a poet, but also as a poetry facilitator. How you move through classes, those things are mastered, right? So when I go into another space that's maybe tech-heavy, I don't mind learning and being, you know, a student of the wonder of how we can make this magic, work together.
Two, you’ve got to know how to pivot. Sometimes we say, ‘Alright, this is what my life is going to be. I'm going to be a New York Times best-selling author. I'm going to, you know, have an album that's Grammy-nominated. And then, say you get dropped from your record label. That doesn't mean you can't make an album anymore. You can also still create an album that can be submitted to the Grammys. So, what does a pivot look like as an artist who doesn't have an institution behind them? Pivot being a student of the wonder.
Relationships also really help. How do I serve the community? And in turn, that tells me how the community can show up. For me, I have long-standing ties with a community that will outlast my one life. So, what does it mean to create space where these relationships can develop, can be nurtured, can be rooted, can be cultivated? Creating space—it happens through relationships.
xoN: With today’s economic challenges, what does your current creative process look like, and what are you working on?
MB: I’m always thinking five years ahead. I just reviewed the pages for two children’s books and recently released a YA novel. I’m drafting an adult fiction manuscript now.
Anything I create is founded with the root of poetry, but it can exist in captions. It can exist in commercials. It can exist as a musical. So that's where I’m at now.
xoN: You started performing "Black Girl Magic" in 2013, had an acclaimed performance of it via PBS and the work went on to viral success shortly after. Talk more about the inspiration. And what do you think about the continued relevance more than a decade later?
MB: I wrote it as a rally cry for the mothers who had been keeping themselves truly in harm's way by, you know, being a part of the community right after the death of their child or their loved one. They are usually mothers of victims of police brutality—and just seeing how they showed up in these community spaces, they are devout to the cause but obviously still grieving.
"I wanted this poem to be just a space of reclamation, of joy and of you, of your light, of your shine, of your brilliance, in any which way in which you fashion. Every room you enter is the room you deserve to be in. What does it mean to have a poem like that that exists?"
And the first time I did the poem, the Weeping that occurred, right? It was like this blood-letting of sorts. The next time I performed it, I'm moved to tears because I'm seeing how it's affecting other women who have just been waiting to hear, ‘You belong. You deserve. You are good. We see you. Thank you, despite everything that they said to make you regret being born in this beautiful brown, dark-skinned, light-skinned, but Black body.’
Black women are the backbone—period. Point blank. And so, that that poem became a necessity, not just to the fortitude of Black women in the community, but like you know, in service of healing the Black women.
xoN: One of your books was banned at a school in Boston, and it was later reinstated due to parental and activist support. What was that experience like?
MB: Well, I think it happened because they were racist. That's it. Point blank. The reversal of it was empowering, right? I realized, oh, I thought we just had to sit here and be on a banned book list. But no, parents are actually the leaders of this charge.
So to see that, the parents said, ‘Nah, we're not gonna let you take this book out of my baby’s school just because it's a Black kid on the front saying, ‘Woke’ and they're talking about being a global citizen. They're talking about accountability. They're talking about accessibility. They're talking about allyship, and you don't want them to have compassion or empathy or have even an understanding, right? So no, we rebuke that, and we want this book here anyway.’ To see that happen in that way. I was, like, reaffirmed. Absolutely.
xoN: You recently organized the Black Girl Magic Ball at the Lincoln Center in New York. Honorees included author and entrepreneur Rachel Cargle and National Black Theater CEO Sade Lythcott. What impact did it have and what expanded legacy do you hope to leave with your creative works?
MB: I was really interested in not celebrating just the book, but celebrating the community that made the book possible. And so I gave out five awards to women doing that thing, like, what does it mean to be a Black girl in this world?
I just thought it was gonna be an amazing time. Everybody's gonna dress up—we're gonna celebrate each other. And boom, I then realized that it responded to like a gaping hole. There was a missing thing for Black girls of all walks of life, all ages, right?
"It's very intergenerational. That was intentional to come together and celebrate just being us."
You have all these instances where just being you is either the butt of a joke or it's diminished and not worthy of a specific title in these larger institutions. So what does it mean to just to be loved up on and celebrated?
It felt like a self-care project at first. You know, for the first couple of years, folks were coming and they were getting that sisterhood. They were getting that tribe work that they were missing in their everyday lives.
I love the Black Girl Magic Ball because we got us. If I go out with a bang, they'll remember that Mahogany worked her a** off to make sure all the Black girls everywhere knew that she was the light. We are the blueprint.
For more information on Mahogany L. Browne, her work, and her future projects, visit her website or follow her on IG @mobrowne.
Featured image by Anthony Artis
“I think for me, an all-American girl, for some reason, brings me back to when I was younger, and just like playing at my grandma’s house and just being outside,” Kennedy told xoNecole ahead of her attendance at the 2025 BET Awards.
“I just feel like when I was younger, you know, you don’t have as many responsibilities. There’s not as much weighing you down, and so I kind of go back to that mindset. Like, even now, being 27, I’m trying to get back to that younger girl.”
The 2025 BET Awards, hosted by Kevin Hart, took place in Los Angeles at the Peacock Theater on Monday night (June 9). The star-studded event was filled with tons of surprises, including a trip down memory lane with a 106 & Park reunion, coupled with performances by artists that dominated the top spots during the music video countdown show’s reign from 2000 to 2014.
Kennedy, who received her first nomination alongside Tanner Adell, Brittney Spencer, Reyna Roberts, and Beyoncè in the BET Her category for “Blackbiird,” the reimagination of the original The Beatles of the same title (minus the extra i), invited xoNecole to get ready with her as she prepared for her first-ever BET Awards.
Beauty Rituals Inherited From Her Mother.
Rather than booking her makeup artist ahead of the big night, Kennedy decided to go on a budget and do the task herself, something that isn’t too out of her norm. She noted how she incorporates some of the things she witnessed her mother do while growing up in her routine.
“I remember being younger and seeing all the makeup laid out on my mom’s counter,” the “I Look Good In That Truck” singer recalled. “I don’t even think she knows this, but there were moments where I would like to go and steal her makeup. She would have Mac. I think it was some kind of foundation powder, and I would go in there and I would put it on, and I’m like I hope she doesn’t see.”
She added, “My mom is very natural with her makeup, so even though I’ve got these big lashes on, I always gravitate towards just neutral looks… I don’t do anything too fancy.”
Tiera Kennedy’s Holy Grail of Products.
Kennedy took it upon herself to take a class to ensure that she’s prepared for nights like these, where she’s the one responsible for bringing her glam look to life.
“We are independent,” she said, reminding us that she is no longer tied to a big machine when it comes to her work as an artist. “We ball on a budget. I have to do my makeup for award shows, events, all the things, and so my makeup artist that taught me how to do all of this, Hailee Clark, she put me on to Nars, the foundation. I don’t know exactly what the name of it is, but I love it.”
“I don’t know all the fancy technicals, but I know that it makes me just look kind of airbrushed, and so I love it. Then, I always use this Laura Mercier [setting] powder because I get real shiny, so I’ve gotta reapply that quite often.”
“We are independent. We ball on a budget. I have to do my makeup for award shows, events, all the things, and so my makeup artist that taught me how to do all of this, Hailee Clark, she put me on."
Her Decision To Wear Hanifa For The Big Night.
Intentionality is essential for Kennedy, which is why she jumped at the opportunity to support Black designer Anifa Mvuemba with a dress from her fashion brand, Hanifa.
“Takirra on my team helped me pick out the dress. I really like to represent in country music, and being in Nashville, I like to represent Black culture through the things that I wear, and I was excited to get to wear a Black brand to the BET Awards,” said Kennedy.
“She was telling me about this brand, Hanifa, and we were on FaceTime just scrolling through the website, and she was like this looks like you. This feels very rooted, like fits those natural tones, and so she bought the dress and was like, ‘This is what you’re wearing.’”
The look was a Raven Knit Dress in Eggplant/Dark Brown Mesh from Hanifa.
Tiera Kennedy in her younger years.
Courtesy
Kennedy also nurtured her inner child for the look, taking it back to her roots with one small detail in her hair that she had her mother carry out before she hopped on the flight to LA.
“I had this vision of wearing beads in my hair because when I was younger, my mom would always do that, and I didn’t love it, but now I’m like, it would be really beautiful to tie all of that together, and the Hanifa dress just fit perfectly.”
“Just even in the past couple of days, I’ve had to take a second, and just look back at all of the awesome things we’ve gotten to do,” said Kennedy when asked what baby Tiera is feeling in this moment.
“I had this vision of wearing beads in my hair, because when I was younger, my mom would always do that, and I didn’t love it, but now I’m like, it would be really beautiful to tie all of that together, and the Hanifa dress just fit perfectly.”
“I dreamed of having a record and having this team that was doing all of these things for me, and now, being an independent artist, and being in control of my career, I’ve gotten to build an awesome team behind me that helps me get to where I am. It’s been a lot of hard work, and I think when I was younger, I would have never imagined that I could do all of these things, and so, yeah, to be here, I don’t even think I would believe it.”
Although “Blackbiird” didn’t win in the BET Her category during Monday night’s show, Kennedy’s future is brighter than ever, which she attests to her faith playing a huge role in guiding her next steps as she continues to rise to stardom.
“Thinking about the next thing, I think that can be really daunting when you’re an independent artist. It’s like you have to be thinking of what’s coming next, to prepare for that, but I think the way that I like to walk through life in general is letting the Lord lead,” Kennedy said.
“I know that a lot of time when I have a vision of what I want things to look like in my head, He always exceed my expectations. So, I think the plan is to continue to release music, and continue to show up as my authentic self. Getting to have these moments like the BET Awards is so awesome, but also, at the same time, that’s not what I do this for. I do it for the humans that are listening to my music, that are [having] fun and healing through my music, so I hope that I can just continue to do that.”
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