Becoming an entrepreneur? I think the thought first hit me way back when I was still carrying around a Jansport backpack, running between classrooms, lockers, and eating peanut butter sandwiches that had seen better days. Still, even years later, it never seriously crossed my mind to start my own business after finishing my English degree. At 20, I had a full-blown fear of phone calls and had never even stepped foot in a real office. There wasn’t a single part of me that felt like one of those “go-getter business types” I saw plastered all over Instagram. I felt like an unsure rookie with zero game plan when I proudly took home my master’s diploma. “I’ll be an entrepreneur when I’m 45 and settled down,” I used to say. And yet, there I was at 21, walking into the Texas Secretary of State’s office to get my business registered. Two years later? Part-time freelancer. So… why?
Looking back, I’ve always had that entrepreneurial fire.
When I reflect on it, I think that spark’s always been there. Even as a teen. At 13, I was flipping secondhand books I found at garage sales and reselling them on Craigslist for a few extra bucks. Not long after, I started crafting scrapbook layouts for niche magazines (and yep, they paid). I cobbled together my student income through every legal hustle under the Texas sun—no illegal greenhouses in this story, promise.
I worked part-time as a student assistant, sold vintage clothes online, did freelance editing, and even taught a couple of craft classes at the local rec center. I never thought of it as “being an entrepreneur,” but looking back, I just didn’t like being boxed in. I liked trying new things, talking to all sorts of folks, and being able to make my own money. Sure, my little Craigslist hustle took over a big chunk of our living room (sorry, Mom!), but my parents always cheered me on—even if I never really told many people about it. While most of my friends were working cashier jobs at H-E-B or Whataburger, I was out there doing my own thing. Quietly. But happily.
Graduated… now what?
If you’d asked me at 14 what I wanted to be, I’d have said it without blinking—“a writer.” I pictured myself holed up in my own cozy writing office, spinning stories or penning advice columns. Didn’t know if I’d write self-help books, Southern fiction, or parenting articles, but I just knew: writing was it.
And yet, once “someday” turned into “right now,” that dream got fuzzier.
I had my degree in hand—three years of undergrad and two more of grad school behind me—and suddenly that big question hit harder than ever: “So, what now?” The dean had said, “The world is yours.” Meanwhile, everyone around me was headed off on international trips, joining big-name grad programs, or taking over the family ranch or business.
Me? I was glued to job boards with zero clue which job title even fit me.
I used to joke, “Just let me keep studying forever.” But after three months of working on one long research project, I realized: nope. Not for me. I didn’t want to climb the ladder to be a researcher. I was crystal clear on what I didn’t want… just not so sure about what I did. “Something with writing” sounded good—but what?
Shooting in the dark: job apps with no aim or confidence
For months, I applied to anything that sounded remotely related to communication. Universities, newsrooms, city councils, nonprofits, retail brands—you name it. Whether the posting said content strategist, copywriter, or communications coordinator, I’d spend two hours tailoring a cover letter like my life depended on it.
But this was during a hiring slump, and especially in my small Texas town, folks weren’t eager to hire fresh grads without experience. Rejections rolled in like summer thunderstorms. I started to think that whole “world at your feet” line was more a nice quote than a fact.
“Hey world, I’m ready!” I wanted to shout. But the world seemed to answer, “Thanks, but we already filled that position.”
Becoming a freelancer… without meaning to
To keep myself sane, I started picking up side projects—editing student papers, running a few social media pages for local crafters, starting my own blog, and volunteering at a local newsletter. I was juggling all this with job applications and working 50-hour weeks… for pennies. My mom would say, “Why don’t you just freelance full-time?” I’d always respond:
“I don’t know how.”
“I’m too young.”
“Why would anyone hire me?”
Still, I kept at it. I didn’t realize it at the time, but I was freelancing—I just didn’t call it that. Eventually, after sending out what felt like 80+ resumes, I landed my first “real” job in a communications department at a finance firm. That 9-to-5 gig taught me a lot: how to talk on the phone without panicking, how to sit through meetings, give and get feedback, and most of all—how to work with a team. Those skills still serve me every day.
A quiet step toward business ownership
While working full-time, I kept blogging and picking up small writing jobs. Eventually, brands wanted invoices—and to send those, I needed a business license. So, I made a weekday trip to register my business with the state. No party, no champagne—just me and some paperwork.
I didn’t tell many people. Most friends didn’t even know I had taken that step. I still called it “my little side hustle.”
That first real freelance gig
I joined a bunch of Facebook groups for Texas freelancers and women entrepreneurs. For weeks, I got zero bites. Then suddenly, someone replied. They liked my writing. They wanted to hire me. I can’t even describe how that felt. It was electric.
That first job lit a fire. I soon found myself working four days a week at my day job so I could freelance more on Fridays. Then came a life-changing message: someone referred me to a tech company needing 100 SEO blogs written. I met the client at a coffee shop in downtown Dallas, blazer on, questions prepped, trying to look like a pro. (Inside, I was sweating bullets.)
I had to Google “how to write a quote.”
I landed the gig.
And it changed everything.
Freelancing takes off
After that, referrals came in. A contact from the mortgage site tipped me off to another client. Folks from my blog started reaching out. One day, I got a letter from a local entrepreneurship program in Waco—three months after moving there. I took it as a sign. I joined, and soon enough, half the group had hired me for web copy. Word spread fast.
Meanwhile, I was fading out at my office job. There wasn’t enough work, and it left me drained. Freelancing gave me energy, variety, and purpose. But going all-in? That still felt scary.
Even with a stable home, low expenses, and plenty of freelance gigs, I was afraid to leap. Why? Maybe because I still believed that entrepreneurship was risky. But really—was it any riskier than staying in a job that bored me?
My path wasn’t one giant leap—it was a series of small ones
I called my dad often for advice. I even saw a career coach who gave me a pivotal exercise: find job listings I’d actually apply to. I found a few. But with each one, my gut said, “You know what? I’d rather just do this kind of work on my own.”
That’s when it clicked—I had more entrepreneurial energy than I’d let myself believe. I didn’t want the big, bold leap. I wanted little steps. I went from five days employed, to four, to three. Slowly but surely, I grew into the business I’d quietly started years earlier.
And today? I’m living that entrepreneurial life
My story isn’t one of going from scared to CEO overnight. I still get nervous. I still mess up. Sometimes I overbook myself, and there are weeks I cross my fingers for a new client. But I can say this with my whole heart:
I’ve never had a job that fits me better than this.
I became a writer—on my terms.
I’ve got a cozy office.
I get paid to do what I love.
That 14-year-old dreamer? He’d be proud.
To anyone feeling that spark, hear me:
You don’t have to jump all at once.
You can take it slow.
Work one day less. Shadow someone. Do one gig. Talk to a coach.
Make it small.
Make it yours.
You never know—your future might just be sitting in a Texas coffee shop, Googling how to send a quote.
Have you ever considered becoming an entrepreneur? (Or are you perhaps even an entrepreneur?)
