I never thought I would be self-employed. I literally planned out my life at 9 to live in New York, finance that lifestyle with a regular-smegular job, and live on fabulously. I really didn't see self-employment modeled in my everyday life, as most of the women who raised me worked for private companies, government entities, corporations, or the military.
It wasn't until college that I'd see self-employment modeled among women, especially the mothers of my friends who were first-generation Caribbean or African. All of their moms were highly educated and held down 9-to-5s but always had some sort of side hustle. Fast-forward to my first major publishing gig, working for a magazine that highlights all that is excellent about Black entrepreneurship, and I finally got bit by the bug. I decided to try consulting as a side hustle.
One day I woke up, ready to go to work after being given a raise and a title promotion, and a voice (God, duh!) said, "Janell, you need to quit. Go off on your own. It's now or never." So I did.
I went full-time with consulting and never left my love for editing and writing behind. No one would tell me that it wouldn't be all about empowering roses, extreme time and energy flexibility, and cashing checks. Baby, it can be a rough road, with many detours, bumps, and even crashes.
If you're considering becoming self-employed, consider what I've learned (mostly the hard way) in my journey:
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Taxes...Taxes... Taxes...
It was all good when I'd get my check at a job, and all the heavy lifting related to taxes had been done already. Maybe I'd cringe that my take-home pay had diminished by quite a lot once taxes were taken out, but that feeling is nothing compared to the utter horrific trepidation that comes with tax season when you have to file as a self-employed professional.
Quarterly tax obligations are real, and a huge lesson I've learned is that you have to really become honest with yourself about your money mindset, how you dealt with money before becoming self-employed, the federal and state tax requirements that apply to you, and the importance of embracing and taking full advantage of the resources out there to help you.
Often, when you're self-employed, you feel like you can do it all, but in my case, I found that dealing with money matters really intimidated me. I had to empower myself by asking for help and getting the information I needed to succeed.
If you're considering self-employment, talk to others who are self-employed, get references for tax attorneys, coaches, financial advisers, or certified accountants, and check out the IRS website to find out the information you need. Look to your local businesses and organizations that advocate for you. Get the knowledge you need and write out a plan of action ahead of time so that you won't be overwhelmed when you're ready to go for it.
And offer yourself grace. Life is not about perfection, and you can't know it all at all times. Experience can sometimes be the best teacher as well, especially when it comes to being self-employed.
Invoicing And Knowing Your Worth
Setting prices for your time, services, or products can be tricky, but if you decide to continue pursuing the same work you did in your 9-to-5 when you move on to be your own boss (like I did), this can be much easier. Be sure to check the market rates for what you offer to the world by going to sites like Salary.com or Glassdoor to help you set a baseline for what you should be getting paid. Ask around your industry and get a mentor who can guide you on this, especially someone who has been in their field, self-employed, for many years. (You want to learn from folk who have receipts.)
Early on, I tragically undervalued my services, talent, and experience and undercharged by a lot. I often felt desperate because, to be honest with you, my confidence wasn't as high as I thought it was when I started the journey. I also had bills to pay and didn't want to go through the shame of failing.
Well, if you're reading this, you can plan better than I did in the early days and set yourself up for success by not only charging what you're worth but adding tax (literally...I just told you about Uncle Sam, sis), but saving up and planning so that you can take or leave any client or customer. You won't be so pressed because you've financially and mentally prepared yourself to take the leap.
Now, I'm not saying deplete all your savings and live off of credit cards and hope. I am saying go into self-employment with a realistic sense of what you should be charging, how your prices and expenses affect your finances, the reasonable market rates for what you're offering to the world, and the quality of life you'd like to have for yourself and your family.
It took me years to get in a good groove of understanding the types of clients I wanted to work with, what publishers I wanted to build relationships with, what I was willing to sacrifice just for the experience, and my hard boundaries for the return on investment of my time.
Again, if you feel confused or anxious about this, get some help. Talk to a coach, join a Facebook group, or invest in courses where you can be around and learn from other self-employed professionals who have been successful, and the fruits of their labors are super-evident.
The Isolation And Loneliness
I've always been one who loves my own company and will do almost anything alone (especially traveling, going out to dinner or movies, or trying something new and daring that I can't convince anyone in my network to do).
However, especially during the pandemic, I learned that while I'm never really lonely, I absolutely hate feeling alone. The isolation really caused me to go inward, lose a lot of my zest for serving people, and ruined any sense of community I'd felt previously. It also made me realize that we need people and that I crave the exchange of human energy when it comes to doing what I love.
Embarking on a self-employment journey means also reaching out and being an active part of networks where you can serve, learn and grow so that you can avoid making mistakes, advance your career, boost your business, make friends, and really contribute in a more elevated way. Go to those mixers, sis. Take that coffee or virtual lunch invite. Travel on that retreat. Volunteer. Do things that will really enrich your spirit and provide some sort of social interaction that will make being self-employed something fulfilling to be.
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Broke, Going Back To A 9-to-5....And Failure
I really want to keep it 100 on this one: Almost every self-employed person I know has had to go back to a 9-to-5 at one point or another, even if it was part-time or something that they would never dare put on their resume. Sometimes, you gotta do what you gotta do.
Some people work a 9-to-5 to fuel their future of full-time self-employment. Some went solo and found that they needed to do a bit more self-development and get a bit more education by working for a company.
Some people took a leap and failed. It happens, and it happened to me. I'm proud of having sold shoes (one of the best jobs of my life), answered phones, or sold products via telemarketing because it taught me humility, customer service, and sales skills and helped me engage with people in a way I hadn't when self-employed.
It also boosted my confidence, letting me know I could do anything I put my mind to and that God would never leave me hanging off a cliff. It strengthened my faith and made me even more determined to continue to go for my dreams.
It also widened my network, and one job even helped me finance a major surgery I didn't even know I'd need. (The actual job was a flop, but the experience was a God-send that I'm forever grateful for because had I not been employed and fully insured, I'm not sure I'd be here to write this.)
Being self-employed isn't the fantasy that's often portrayed on social, but if it's the path for you, it can be super-rewarding. Be sure to take heed to the lessons I've learned along the way, remember your why, stay diligent, enjoy the process, and be that successful self-employed boss you were called to be.
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Some women have their whole wedding planned out, from the bridal gown and venue to the bridal party and playlist. However, KJ was not one of those people. “I didn’t foresee a wedding in my future,” she reveals. “I was just gonna be the boss chick, rich auntie. I didn’t force love in my life until recently. I never had an idea of what a dream wedding would look like, it was easier for me to elope.”
KJ Smith
Photo by Stanley Babb/ Stanlo Photography
And to many people’s surprise, that was their original plan – until Skyh brought up a valid concern. He was raised by his grandmother and thought she should be at the wedding, and naturally, that led to KJ wanting her grandmother to be there as well – then her mom – and later her sister – and, you’ve gotta invite the besties too, right? From there, the guest list continued to blossom. Much like the updo and pop of color bold red lip, she wore on her special day, which was initially on her Pinterest board as a soft glam look with her hair hanging on her shoulders, KJ is okay with changing her plan if it brings her and her loved ones happiness.
So let’s get into the wedding, which took place in Malibu, CA. The first thing you should know about the celebrity couple is that they’re non-traditional. They know, and they don’t care. So, in true unconventional fashion, they shared the morning of the wedding together.
“I woke up with Skyh, we walked our dog, had black coffee, and said good morning to the people who stayed at the venue with us,” she says.
Now, it was time for hair and makeup. While she was getting glammed up, she had Black-owned McBride Sisters wine and champagne (which ties into The Black Experience theme) on deck with her mom and friends, had her besties help rework her vows, retried on every outfit (sis is very Type-A), took photos, and ended the early-celebration with prayer and meditation. It seems very non-Bridezilla, I said.
“Yeah, I was the most unbothered bride ever. Everyone was just so supportive. As entertainers, we go on red carpets all the time. We actually have a production company,” she explains. “The get-ready process was like a day at work, but with people we love the most. Being entertainers, we didn’t feel stressed at all, but my excitement was so high.”
Things moved quickly, and before she knew it, it was time to line up to walk down the aisle.
“Yeah, I was the most unbothered bride ever. Everyone was just so supportive. As entertainers, we go on red carpets all the time. We actually have a production company. The get-ready process was like a day at work, but with people we love the most. Being entertainers, we didn’t feel stressed at all, but my excitement was so high.”
KJ Smith and her bridal party
Photo by Stanley Babb/ Stanlo Photography
Since everything started with their grandmothers, the couple wanted to ensure they honored them and planned to keep an element of their wedding traditional. Although we’ve all seen the reception videos and photos online, you may have noticed visuals from the wedding itself are harder to find.
“We planned for it to be traditional, but we’re not like that, so we tried to create those moments. We jumped the broom and had a salt ceremony (where the bride and groom individually pour salt into a glass container, symbolizing their lives becoming one.) But honestly, still, nothing was traditional about it.”
She goes on to explain that her mom caught the holy ghost coming down the aisle, her glam team was on deck, and she became so nervous with excitement that she had an anxiety attack – something she struggled with for years, she explains tearfully. Her friends had to literally cheer her down the aisle because of how overwhelmed she felt until she eventually calmed down.
“Skyh was standing there with his hand on his heart; we have our own little language, and I could feel the support,” she shares.
It was surprising to hear all these emotional moments happened before the party we saw online. That is until she once again got into the backstory.
“As a Black woman actress, for so long, it was popular to be mysterious and secretive, but that’s not who I am or what I like. Plus, we both wanted to create an experience for everyone there. We are the people who always host family and friends,” she says. “Like for me, the first order of business was getting sandals for the women so they can dance all night long. We had oxtail, D'ussé, and a coffee and sativa lounge – which is part of Skyh and I’s lifestyle and routine. We wanted to bring them into our world.”
Skyh Black (L) and KJ Smith (R)
Photo by Stanley Babb/ Stanlo Photography
She went on to discuss the dance routine she did for her husband at the reception, which has taken over the internet. Apparently, that’s another thing that didn’t go according to plan. According to KJ, she had promised a performance at their joint bachelor/ bachelorette party, but her outfit got stolen from her car. So, Skyh ended up performing for her – complete with a strip tease. Still, she never forgot her promise to dance for him.
So, she hired her friend as a choreographer, learned the routine, made friends and family watch it endless times, and attended Beyoncé’s Renaissance show a few days before for a confidence boost. It ended up being a show to remember. But that wasn’t all the night offered. Lil Mo performed, and the guests received special goody bags featuring their favorite Black-owned products like journals, hair care, and more.
“We made sure everyone was taken care of all night. That kind of stuff makes us happy. I wanted everyone there to experience the joy and love I have for myself, my partner, and for them. I wanted them to feel full and whole, and they had the time of their lives,” she says.
But naturally, the internet is going to internet, and while there were countless people praising the event and applauding the newlyweds, some thought it was too over the top. I was curious to know her thoughts on some of the criticism.
“It’s cool. We did what we wanted to do. I’ve decided to share my world with people. Just how I went on social media platforms and found inspiration, I want people to do the same,” she explains. “I don’t think it's fair to my supporters not to give that out. There’s so much I wanna share with brides, specifically Black brides. I love that people are adding it to their Pinterest boards."
"I wanted everyone there to experience the joy and love I have for myself, my partner, and for them. I wanted them to feel full and whole, and they had the time of their lives."
KJ Smith
Photo by Stanley Babb/ Stanlo Photography
“I’m happy with it because we did what we wanted to do. They can do what they wanna do. Don’t be cruel, though, because you will get blocked,” she said, laughing.
The more I spoke with her, the more her sense of freedom shined through. People are always going to have their opinions, but at the end of the day, it’s you who has to live your life, and it seems like the couple realizes that and embraces that power. She also stressed the importance of not living for others and the lessons life has taught her.
“I’ve been to countless weddings, and I’ve been in countless weddings. I’m a generally older bride. So when women in my demographic get married, and you and your husband are busy working people like us, you deserve to have the one you want to have,” she shares.
“This is what we wanted to do. Our loved ones love and support us. We did so much to honor them, but we also wanted to start our own tradition, legacy, and creation. I'm not going to be pulled back into ideas of the past when I’m trying to create a future with my partner. “
If you’d like to see more of the couple, you probably won’t have to wait long. Although no content is planned yet, she admits to being an oversharer. “Me being open and transparent about my experiences lets people know it’s okay to have flaws; it makes you human, and for many years, I didn’t believe that was okay. I had pressure to be perfect, and I’d crumble every time,” she explains to xoNecole.
Now, she owns her flaws and uses them as a superpower to connect with her community and feel and express her love.
“Some people give us [Skyh and KJ] a hard time because they say we just seem too perfect. I’m like, why is that a bad thing? I love the people I love. From my man to my mama, to my friends - unabashedly. We move through time and space how we want to move. If we did it another way, we’d let ourselves and our union down.”
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Feature image by Stanley Babb/ Stanlo Photography
