Meet Chicago-based Ashantis Jones.
Newer to freelancing full-time, Ashantis has been using their entrepreneurial spirit to do sporadic freelance jobs since 2016 but this year, they’ve hit the ground running with a serious freelance career. They’ve been experimenting with a wide variety of services, all in the wellness education arena, where they’ve been building a following and devoted client base for personal training, group fitness classes, social media content creation, corporate trainings, coaching, therapy, virtual assistance, and more.
While that may sound like a lot, they wouldn’t have it any other way because it allows them to fill the many different buckets of what brings them joy. Keep reading to hear Ashantis’ journey thus far and their tips for LLCs, imposter syndrome, burnout, and tech tools.
Year started freelancing: 2016, full-time 2023
Age when started freelancing: 22, full-time 28
Preferred Pronouns: she/them
Getting into Freelancing
You’ve been freelancing on and off for several years, what made you decide to turn it into a career?
Right, I began with sporadic gigs, mostly helping friends and acquaintances with various tasks.
I started taking freelancing more seriously this year. The decision was influenced by the instability in the job market, experiencing layoffs, and a realization that corporate environments never felt like the right fit for me.
What was your educational and experiential background before starting freelancing?
Initially, I started with a high school diploma and internships.
I later earned a Bachelor of Fine Arts in Theater Management with two minors in business-related fields. After some time just working in corporate jobs, I went back to school and obtained a MEd in Counseling, specializing in college counseling and student affairs and clinical mental health, so I could see people as a therapist.
Plus, I got my National Academy of Sports Medicine certification to become a certified personal trainer and a DEI certificate.
On top of my skills as a fitness and mental health professional, I started by offering freelance virtual assistant services, supporting small businesses and individuals doing similar work as me in Chicago. This has involved a wide range of tasks from website updates to event planning.
I’ve intentionally set up my business to have a diverse range of services so I can allow my brain to work in many different ways.
Can you elaborate on the range of services you now offer?
There are so many of them, but they all generally fall under wellness education. My services in health and wellness include personal training, group fitness instruction, corporate fitness, and mental health coaching (pre-licensed therapist).
This year I’ll have therapy clients as well, but that will be contracting through a private practice.
Services on the education side include public speaking and trainings on mental and physical health and having a holistic approach to both.
On top of that, I’ve also ventured into virtual assistance, supporting weight-inclusive providers and Black-owned businesses, but I am not taking on any more regular clients like that at the moment.
How do you explain this to people as an elevator pitch?
Typically I try to find out what the other person’s doing first. Then, I’ll give them an elevator pitch based on what I think makes the most sense for them.
Business Management and Marketing
How do you manage all these different income streams?
I consider them as all different arms of one business, which is filed under wellness education initially.
For managing it, initially, I organized everything through HoneyBook, but I recently switched to Square because it’s been free or less expensive for me. I use it for invoicing, contracts, point-of-sale, and holding all my client information.
I’m a big fan of using tech, especially free tech, to support my business automations.
Do you find it challenging to market the diverse range of services you offer instead of just one niche?
Absolutely. The way I’ve handled it is I focus my marketing on where I want to put the majority of my effort at a given time. For instance, if personal training is my priority, I channel my marketing efforts towards that. I base these decisions on where most of my consultation requests are coming from and the potential
How did you go about getting your LLC, and what role did your family accountant play in the process?
I consulted with my family accountant, who is a CPA and had been managing my mom’s business. Given her expertise, the process was straightforward. I asked about transitioning from a bunch of 1099 paperwork to having my own LLC. She handled the paperwork, and I essentially just signed a piece of paper.
Having this resource, which I already knew and trusted, was crucial. She filed everything, helped with deductions, and seamlessly integrated it into my regular tax bill. Working with a CPA who has been doing this for large corporations for over 20 years makes me feel very safe and secure in my single LLC.
Why did you choose to establish an LLC instead of a sole proprietorship or other business format?
I explored different options with my CPA based on my business goals. Considering I didn’t plan to have employees and wanted flexibility, my CPA suggested a single-member LLC. It made the most sense from a tax return and deduction standpoint. The decision was guided by understanding my long-term plans and the assurance that I wouldn’t be hiring employees.
How did you create and manage your website, and what platform did you choose?
I’m a Squarespace girl through and through. Back in 2016, my partner helped me create a custom portfolio site. However, after parting ways, I transitioned to Squarespace for its user-friendly interface. I chose Squarespace over other platforms because it offered simplicity without dealing with plugins or complexities associated with platforms like WordPress. I’ve revamped my site a couple of times but remain a Squarespace enthusiast.
How much did you make in your first year freelancing?
I don’t have an exact number for you, but I think I made around 20 grand this year from freelancing. I think I told myself I was going to make 80 grand by the end of this year and April me was a little delusional.
Have you experienced imposter syndrome, and how do you cope with it?
Imposter syndrome is a daily struggle I’m working through, especially with some of the random contracts that I’ve gotten in the content creator space. Sometimes it’s like “who gave you the right?” And I remind myself of my qualifications, all the education I’ve done to be able to do this work, and the experience I’ve had. It’s about recognizing that my expertise and achievements grant me the right to pursue this line of work.
It’s a lot of what I’ve told coaching clients and previous therapy clients where sometimes you’ve just got to look in the mirror and remind yourself, “You are that girl.” Even when you don’t feel like it, you are. (Megan Thee Stallion)
What about burnout and what advice do you have for freelancers facing it?
Frankly, there are some days when I wonder if I will ever not be low-key burnt out. But that has more to do with the system that is capitalism and how we interact with it more than about us as individuals.
I really like the metaphor of a battery. If you take a battery out of the pack and it’s fully charged, it’s gonna work like a fully charged battery. Versus if you take a battery out of a different remote that’s already been in there and then it dies in a week once you switched it to a different remote, you can’t really be mad because it wasn’t a brand new battery. Sometimes we have to think of ourselves that way too; if you wake up in the morning and you’re already on low, you do not have the same productivity level as the day when you woke up at halfway or 95%. Those are different people. Capacities as humans can ebb and flow and that is very normal.
We need to separate between manmade capitalism and what is real.
As a woman, queer person, and disabled individual, what challenges have you faced in freelancing, especially in the fitness and mental health space?
The challenges have been multifaceted, including online harassment, societal biases, and navigating within non-traditional spaces. I don’t utilize weight loss or static base changes at all. The norm is thinness and whiteness and why is that?
It’s been tough as a queer person, certainly as a disabled person because that definitely impacts how quickly I end up in burnout. Being neurodivergent, but then also like having a chronic illness with Fibromyalgia, like those things are all their own challenges. It takes time to be your own caregiver.
Acknowledging the uniqueness I bring to the industry, I focus on the positive impact on my community. I try to continuously remind myself that if I was doing something wrong, I would have zero clients, I wouldn’t have any followers, and I wouldn’t get a random DM from someone saying today this post was really helpful for me. Getting those words of encouragement from people has been super helpful with navigating all the bullshit and noise.
If you could offer one piece of advice to a new woman freelancer entering wellness, fitness, or the outdoor industry, what would it be?
Establish systems early on to set yourself up for success. Whether using technology or other methods, create systems that suit your needs. Adapt your business to your lifestyle, avoiding the trap of recreating a nine-to-five environment. Stay organized, inquire about deductions, and work with other professionals who can help.
Learn More About Ashantis Jones
Want to learn more about Ashantis and what they’re all about? Check out their website and follow them on Instagram and TikTok for more wellness tips and weight-inclusive fitness content.
Want to support their business? Join one of their online or in-person weight-inclusive group fitness classes and wellness events! Alternatively, reach out about personal training or wellness coaching.