The Raw And Real About Self-Employment
Career & Money

The Raw And Real About Self-Employment

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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