From the young age of 6, I wanted to be a writer. I honed my craft in a tiny purple journal with a kitten on the cover. Each entry started with “Dear Darla”—the name of the journal, of course. While I had the habits of a writer down pat, I didn’t expect the path forward to unfold as it did. Here’s my story.
My late teens and 20s
Age 18: I just want to be a writer, so I publish my first news article in the local paper as a high school senior. I make $15 to spend on going to the movies with friends.
Age 22: I’m a teacher, and sometimes I write for fun. I graduated journalism school in a recession as newsrooms were closing and print publications were dying.
Age 28: I still want to be a writer, but I’m also still a teacher. I wonder daily if I took the right path.
My 30s
Age 33: I am a teacher-writer. To stay sane during COVID-19, I started helping more publications cover the pandemic news. Meanwhile, virtual teaching kills my love for education one Zoom call at a time.
Age 34: I become a writer. But I was one all along, right? I turn in my resignation letter for teaching when my freelancing income starts to outpace my teaching income. I establish my LLC and start calling myself a small business owner of a marketing and media company.
Age 36: Pregnant with my fifth child, I scramble to finish my last deadlines and turn in client work before going into labor. I’m able to work part-time as a freelancer—a must with my gaggle of kids—and make more than triple the income I would have made while teaching. Why did they always say creatives can’t make any money?
Age 37: I update my website from “writer” to much more after realizing my freelance business has expanded. I write: “I am a journalist, copywriter, content marketing writer, editor, content strategist and coach to other freelance business owners.” And, I also post my favorite clips and client work, everything from the Washington Post and Consumer Reports to collaborations with Johnson & Johnson, What to Expect and hospital systems across the country. I haven’t “made it.” I feel like I’m just getting started.
Thriving on your own as a freelancer
Freelance life isn’t for everyone—but it is for the 64 million Americans (38% of the U.S. workforce) making it out there on their own, according to a 2023 UpWork survey. This was the highest number in history of freelancers working in the U.S. The future looks bright, with 85% of freelancers reporting their best days of freelancing are ahead of them.
Freelancing is the first job I’ve woken up each day excited about. The possibilities of expanding your own business based on your own availability, interests and strengths, and rejecting those that don’t serve you, is incredibly empowering. Have a toxic boss? Not with freelancing. You are the boss, for better or worse—but it’s usually for the better.
This level of flexibility means that on Friday mornings, I go garage-saling with my mom and kids for retro purses and new toys. It means heading to the gym at the time of day my body needs it the most, not when my company gives me a break. It also means hand-selecting clients, publications and “colleagues” who radiate positive energy, thus curating my environment to feel meaningful and uplifting.
Moments of frustration
Freelancing isn’t all freedom and bliss and big dollar signs and creative brainstorms. It’s a lot of work, especially in the beginning. Nobody teaches you how to run a business or who to ask about running a business.
You’re often chasing payments and following up again and again on outstanding invoices. Editors and project managers don’t “owe” freelancers anything, like they do their own staff, so they might stop communicating midproject and change directions completely and without explanation.
At first, finding and building relationships and creating an avenue for a continuous stream of business is a struggle. But with patience and consistency, it’s not only doable—it’s also worth the wait.
Depend on friends—and others you trust
My friends are my exceptionally helpful assistants. Finding an assistant is a worthy but daunting endeavor. But as a freelancer and a solo business owner, having another person or two who knows the ins and outs of your business means a second set of eyes to catch mistakes (like when I scheduled a deadline out two years from now) and someone to handle tasks unrelated to your creative process, such as invoicing.
Some freelance coaching clients I work with are hesitant to hand off any part of their business to someone else, but at some point the reward outweighs the risk. It helped them to start delegating smaller items before all of the invoicing or email management.
Assistants and friends along the way, such as other solo business owners, become your colleagues. And everyone needs colleagues, even if you are remote.
Let’s talk money
At a family reunion, my great aunt introduced me as a “mommy blogger,” which she meant as a compliment. But images of bloggers, writers and other creatives send an outdated message of “starving artists,” which doesn’t have to be the truth in freelance life.
At first, it helped to have my freelance work as a side gig to my regular career, as many do. As my career ramped up, I had to consider tough work-life balance decisions, such as investing in full-time day care.
Growing a business can feel like a full-time job—and I’ve been through times where it certainly was one—but I ultimately settled on 20- to 25-hour weeks to achieve a healthy balance between self-care, work, momming and trying to tame my family’s laundry mountain.
Budgeting and financial planning
I budget enough to pay my assistants, which ends up being around 40 to 60 hours of work per month for them. Other expenses are minimal, including some seminars and workshops I want to attend, additional fees I incur from travel journalism on media trips, subscriptions to publications and other freelancer tools. I pay an accountant I love and have worked with a few coaches I also love, all of whom are worth the investment.
I pride myself on transparency in finances and encourage other women and creatives, especially, to do the same so everyone can see what is possible in this field. And, I started with that very first $15 story. In 2020, I had my first $1,000 month. In 2021, I had my first $10,000 month but had to account for an unpaid maternity leave, which is exceptionally difficult as a freelancer and requires diligent savings during and before pregnancy.
Then, in 2022, I passed my $20,000 month goal but became cautious of burnout. I started to check my hours to ensure I was keeping that part-time schedule I’d committed to, not just a bottom line. In 2023, I reached $27,000 per month, but more importantly, I figured out how to save for a month of vacation.
This year, in addition to financial goals—which are incredibly important when you have five kids and shouldn’t have calculated how much college will cost in 18 years—I’m prioritizing stress management, exercise and going outside more. My financial goals are intertwined with finding people I love working with, who value my abilities and pay what I’m worth.
But… what do you DO all day as a freelancer?
I get this question a lot. Apparently, freelancing sounds a lot like sipping lattes in a cafe with a laptop and not like work to some folks. Here’s what a typical day looks like for me:
Early morning
7 a.m.: My 3-year-old bangs on his door to come out. He wants to lie in my bed but gets mad if my other four kids beat him to it and brings the toddler rage. We all have a cuddle-up, pile-on-Mom-type situation for a few minutes before my husband leaves for work, ushering half of them out to day care. We ask Alexa about the weather, which informs whether I’ll put on my gym clothes first or a work-from-home outfit (I have sloppy ones and more put-together ones, depending on the agenda for the day, which I check next). I’ll scan my email, apps and bank accounts to see what’s happening while my kids get ready.
8 a.m.: I down a protein shake and a coffee and see the last of my five kids off to school or camp. I look around at the hot mess of a house and try to realize that I just happen to work here, and I don’t have to clean and work at the same time. Sometimes that mindset works and sometimes it doesn’t. On a great day, I thaw some meat from the freezer for dinner.
Morning
9 a.m.: I head to the gym, which only happens on days I’ve blocked out on my calendar to prevent people from choosing that spot for interviews or client meetings. It’s a 30-minute, boot-camp style class that has been essential for my postpartum recovery. I pump breast milk in the car on the way back or during my first Zoom call.
10 a.m.: I’d like to say I’m deep in creative work at this point, but I’m typically still digging out of my inbox, which consistently fills up with publicist pitches, client requests and editor interactions throughout the day. I tend to jump around in my tasks, cleaning out some emails while sending some pitches to publications or new clients. My preference to bounce around between tasks, such as checking my email after finishing a trying chunk of an article, works best for me—something that took me a while to accept in the world of TikTok productivity “best practices.”
Midday
12 p.m.: I wrap up a few calls, such as an interview with an organic farmer in Iowa who specializes in growing crops for perinatal parents and a coaching client call with a freelancer hoping to gain more confidence in pitching editors. Then, I realize I haven’t eaten in a while when I see my neighbor come home from work for a lunch break—the world outside my office window is my timer. I text the babysitter back and answer a call from the school that one of my kids has a headache and needs to be picked up. I head out to get him—something that would have required taking half a day off (sometimes unpaid when I’d run out of sick days) as a teacher.
1:30 p.m: I start to lose steam and sometimes stop here for a bit. A chronic back problem that only eases with movement sends me outside on a walk with my Aussie-doodle rescue, Jack Frost. I lose, or maybe gain, a half hour in conversation about balancing work and home life with the neighbor, another remote worker out for a stroll.
2:30 p.m.: The kids start trickling in. My husband and I text about the complicated evening of practices and pickups, who is driving where and what we’re eating for dinner. I finalize a piece I’m editing between kids asking for snacks and showing me pictures they made. I have to relocate my train of thought a few times, but my kids’ brotherly banter signifies the workday is wrapping up.
Early afternoon
4 p.m: Coffee break. Nonnegotiable. Sometimes with my mom, who lives nearby. I open some packages that have come in for product-testing articles, such as kid-sized kitchen knives or the best travel raincoats.
4:30 p.m.: I make dinner and the kids’ lunches for the next day, find sports uniforms, throw in a load of laundry and answer a question from my assistant via text or Trello board alerts.
Evening time
6 p.m.: I watch my kids’ soccer game, brainstorm a pitch about kids’ sports, then try to turn my work brain off.
8 p.m.: After putting the kids to bed, I flop down for quality time with my husband, which usually involves recounting the highs and lows of the day.
9:30 p.m.: I resist the urge to knock out some emails for the next day and go to bed instead.
I know this is one of the busiest and most chaotic times in my life, but at the end of the day, I realize how lucky I am. Having a flexible career, doing what I love and being able to close my laptop and head to the pool with my kids on a hot summer afternoon is the definition of success.
This article appears in the September 2024 issue of SUCCESS+ Magazine. Photo by BongkarnGraphic/Shutterstock.
