She Quit a $50K Day Job to Follow Her Dreams — And Earned More by Month 3

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Freelance business
Jessica Lawlor is the CEO and founder of Jessica Lawlor & Company, LLC. Photo by Chrystina Noel

Jessica Lawlor is good at being uncomfortable.

She hated her first yoga class, but she went back — and fell deeply enough in love with her practice to become an instructor.

She “didn’t really plan on becoming a writer,” but the title is one in her manifold resume. (Other entries include editor, content manager, speaker, professor, consultant and CEO.)

So it makes sense that her blog, Get Gutsy, is all about finding your best self at the end of your comfort zone. It was also the key to her eventual (and surely uncomfortable) decision to quit her hard-won day job and take on the freelance life full time.

And as it turns out, discomfort is 100% worth it.

Although she’s only been in business for about a year and hasn’t yet celebrated her 30th birthday, Lawlor’s earnings now dwarf the $50,000 salary she left behind.

Here’s her story — and her best advice if you’re looking for some lucrative discomfort of your own.

Quitting Your Job is Scary… But It Can Pay Off Big Time

Lawlor spent six years climbing the ranks in corporate public relations positions after studying the subject at Temple University.

It’s not like she didn’t like her jobs. She worked first in healthcare and later in travel, and PR itself was a blend of all her passions: writing, speaking, creativity and strategy.  

But Lawlor always knew she wanted to work for herself.

She’d been inspired by a book she’d read in college about making a living as a freelance writer. “I had no idea that was even a thing,” she said. She’d always been drawn to writing, and in her freshman year had briefly studied journalism.

Plus, she said, Temple has a reputation for churning out hard workers, hustlers and entrepreneurs. “The word ‘gritty’ is used to describe it a lot.”

Still, when she started her blog, she had no idea it would be the key to her future. It was the fall of 2012, two years after her college graduation.

Lawlor had always been very involved as a student, constantly taking on side gigs, internships and extracurriculars. So after turning the tassel, she found herself at a bit of a loss.

“All of a sudden, all I was doing was working,” Lawlor said. She’d never had so much free time. Even though she logged 40-hour workweeks, it felt like she was on vacation.

So in her free time, she found herself doing some pretty gutsy things in the pursuit of finding new passions — like getting active, losing 40 pounds, and becoming intentional in her networking — writing about it all the while.

One day, she found an interesting email waiting in her inbox.

Greg Galant, CEO and cofounder of Muck Rack, had noticed an article of his had been referenced in Lawlor’s blog. (She had tagged him in a Tweet.)

He wanted to say thanks and to ask if Lawlor did any freelancing — he needed writers for his company.

After she penned a few guest posts for the company blog, Galant upped the ante, asking Lawlor to become his blog’s managing editor. Did she feel like she was up to the job?

Well, maybe not — but remember: Lawlor’s an expert in discomfort.

“I lied and said yes,” she told me. “Fake it ‘til you make it.”

And “make it,” she did. After taking on that first gig, other opportunities began flowing her direction. (You can read more about how she landed her various clients here — Twitter proved an invaluable tool.)

Eventually, waking up at 5 a.m. to keep up with her side hustle stopped making sense. Plus, she’d never been a morning person.

So Lawlor quit her job and took her freelance business full time in December 2015.

Fast forward: now she’s the CEO and founder of Jessica Lawlor & Company, LLC. She has one employee so far, and at one point earned $10,000 in a single month’s time.

In other words, she knocked the freelancing thing out of the park.

Want to Start Your Own Business? Here’s This CEO’s Advice

Even if your day job isn’t well-paid and cushy, it can be terrifying to let it go in pursuit of your dreams.

But if you’ve been fantasizing about starting a business of your own, Lawlor’s story might inspire you to, well, get gutsy.

“There’s more out there than sitting in a cubicle for 40 hours a week,” she promises.

Before you start drafting your resignation, however, here are a few pieces of sound advice for aspiring entrepreneurs.

1. Get Hustling and Start Saving — ASAP

Lawlor was freelancing long before she dropped her full-time job to start her business, which was key to her success for two important reasons.

First of all, she was able to save up a $40,000 backup fund in case her plans fell through.

And secondly, it helped her narrow down exactly what she wanted to spend her time doing.

Lawlor dabbled with freelance writing, social media marketing and consulting before eventually finding her main source of income in content management.

“Whatever it is you think you want your business to be, start doing it right now and save that money,” Lawlor advises.

It’s always nice to have some extra side hustle cash — and if worst comes to worst, you’ll learn what you don’t want out of your freelance career.

2. Prioritize and Focus — You Can’t Do Everything

By the time Lawlor had the wherewithal to quit her job, she was working 16 hours almost every weekday.

Whether “work” meant freelance writing at 5 a.m., sitting in her cubicle from 9 to 5, or staying late chatting after teaching evening yoga classes, it was undeniable: Her life was too full.

“I was doing all these cool things, but I didn’t really feel fulfilled,” Lawlor said.

So she made a list of everything she was doing, and circled all the stuff she felt she couldn’t live without.

“The only one I didn’t want to keep was my full time job.”

She knew what she had to do.

Prioritizing and focusing not only helps you avoid burnout, but also enables you to strategize your business. Although Lawlor earns money in a variety of ways, she knows where she needs to spend the majority of her time and energy to continue being successful.

It’s a fact of life, after all: You just can’t do everything. So pick a few things and do them really, really well.

3. Have a Backup Plan and Eliminate Unnecessary Expenses

Lawlor didn’t even think about ditching her day job until she had some considerable savings.

“It eased my worries a ton to have this money to fall back on,” she confided.

One reason Lawlor was able to save up that $40,000 cushion in just three years? For the first six months after starting her company, she lived at home, as she had since college.  

And once she did get her own apartment, Lawlor realized just how nice it had been to have people around during her workday — even if they weren’t actively conversing. (Work-at-home freelance writers quickly learn how isolating their career choice can be.)

“There’s no shame in it,” Lawlor said. “I actually really loved that experience.”

In fact, she still visits and works from her folks’ home on a regular basis.

4. Use, Use, Use That Network

As mentioned above, networking — both online and in real life — was key in the creation and growth of Lawlor’s client base. In fact, she found just about all of her clients through her network rather than via cold calls or emails.

If you’re not a natural networking guru, here’s a piece of sage advice: Use your social media feeds to promote not only your  own work but also that of others.

It’s an easy way to make new connections and strike up possible business opportunities.

5. Be Yourself

It might seem trite, but she swears it’s her secret ingredient.

Whether on Twitter, Facebook or her blog itself, Lawlor makes it a point to be transparent.

She writes about her wins, of course, but blogs about the un-sexy parts of business ownership, too. (Tellingly, the latter of those two posts is exponentially more popular.)

People like authenticity, she’s discovered. She guesses it has to do with the innate disconnect between real life and our carefully-curated online personas.

A reader might “see your Instagram post from the beach on a Monday, but they don’t see what goes into that,” she said. To counteract the dichotomy, Lawlor’s as honest and real as possible.

“We’re all human, we all have our flaws and that’s what people relate to. Being vulnerable,” she added, “has actually helped me get more clients.”

So there’s more incentive than mere authenticity to follow Lawlor’s mandate:

“Be yourself online.”

Hey — no one said it was going to be comfortable.

Jamie Cattanach (@jamiecattanach) has written for SELF, Ms. Magazine, Roads & Kingdoms, VinePair, The Write Life, Wonderfilled Magazine, Barclaycard’s Travel Blog, Santander Bank’s Prosper and Thrive and other outlets. Her writing focuses on food, wine, travel and frugality.