Ask most people if they’d like to be their own boss and there’s a good chance you’ll hear “yes”—especially if it’s a Monday morning.

But when it comes to following through with that wish, few of us end up veering off the beaten career path.

In fact, a new Pew report finds that only 10% of the workforce is self-employed—a number that has actually declined slightly over the past 20 years.

But while quitting your day job to go solo is admittedly risky, like all risks it can lead to rewards—including a boost to your career satisfaction levels and even your bottom line.

To see what it really takes to strike out on your own, we found three wannabe-self-employed dreamers and asked them to share their plans with us.

Then we asked career and money pros to assess if they’re really ready to make their DIY career dreams a reality.

“I Want to Run My Own PR Company.”


Deja Cromartie, 25, Search Engine Marketing Coordinator, Philadelphia, Pennsylvania.

Why She Wants to Be Self-Employed

“I studied communications in college and have always had a passion for helping others tell their stories. I’ve been taking on some PR clients on the side, and I’d be so excited if I could make it my full-time career one day soon.

I love to explore, and I feel that PR would allow me the flexibility to travel for work and for fun. Plus, it would be amazing to hire my own team—helping people start their own careers and be successful is really appealing.”

How She’s Planning Now for the Leap Later

“Nearly all of my $45,000 salary goes to living expenses. But I’m putting my PR earnings into savings, which are about $5,000 now.

I’m also trying to set goals and expectations for my future business. For example, I want to make sure I’m generating consistent income—bringing in the same amount of revenue for six months—before I quit my job.”

What the Career Pros Say

Mary Beth Storjohann, a San Diego-based Certified Financial Planner™ (CFP®) and founder of Workable Wealth, thinks Deja is smart to save the income from her side gig working with PR clients while keeping her full-time job as she tests the waters.

Still, Storjohann raises a concern: Deja’s lack of an emergency fund, which should ideally be the equivalent of six months’ take-home pay. She feels that Deja needs this cushion—in addition to savings earmarked for her future business.

Aimee Cohen, the Denver-based owner of Cohen Career Consulting, agrees—and adds that Deja could benefit from creating a more detailed business plan.

“Does she have exact numbers on her overhead costs? Does she know who her competition is? What her marketing plan will be? How much business she needs before she can feasibly hire employees?” Cohen says, listing questions Deja should consider. “These are all important pieces of information that many new entrepreneurs don’t think about.”

To help answer those questions, Amy Swift Crosby, founder of SMARTY, an entrepreneurial network, encourages Deja to seek out a mentor.

“Get close to someone in PR who owns her own agency,” she suggests. “Deja may choose to do it differently, but the realities will be the same.”

What Deja Thinks

“It’s good to know that I’m moving in the right direction, and I’m inspired to save even more, particularly when it comes to emergency funds.

So my next goal will be to scale back my spending, stick to my budget, and stash away that extra money so I have a big enough financial cushion to make the leap.

I’m also going to focus on picking up two or three more PR clients and look into creating that business plan—so that I’m clear on all of the details that will make my business a success.”

Related: How I Did It: I Left My Corporate Job to Work for Myself

“I Want to Launch My Own IT Business.”


Mike Garuccio, 25, Telecommunications Server Administrator, Cleveland, Ohio.

Why He Wants to Be Self-Employed

“I’ve got an entrepreneurial spirit. As a high school senior, I took server administration courses at a community college, which landed me an internship at a major manufacturer and eventually led to a job.

To make extra cash, I’ve also worked for the Best Buy Geek Squad, which has helped give me the confidence and skillset to go out on my own.

My goal is to provide everything from web design and hosting to more traditional IT tasks, such as desktop and network management.”

How He’s Planning Now for the Leap Later

“I’ve started identifying clients on Thumbtack, a small-business platform, while trying to build an audience on Facebook. I hope to convert those “likes” into business soon.

I’ve run the numbers and know that I will need 25 to 30 clients to replace my income of about $65,000.

I’m only working with about five clients now. But scaling up is tricky because, with my day job, people need to be willing to work within my current restricted schedule.

My biggest concern is really whether I’m financially ready. Luckily, I have low expenses, thanks to a supportive, live-in girlfriend—and we’re renting a house from my parents. I’ve also been cutting costs anywhere I can to prepare for when my day-job income stops.

So far, I only have about $3,000 in emergency savings, because money I’ve made from clients has gone to cover things like web hosting and business cards.”

What the Career Pros Say

Swift Crosby points out that Mike is fortunate to have another household income stream through his girlfriend, as well as a forgiving rental situation.

“These both provide household stability, so he can sustain any surprises that may come up during his transition,” Swift Crosby says.

However, she says it would be even better if Mike had more saved up. Storjohann recommends that he focus on building up his emergency fund to the equivalent of six months’ take-home pay, highlighting that he should keep in mind that his earnings will need to cover personal spending as well as business operating costs.

As part of creating a business budget, Swift Crosby raises some questions for Mike: Is the company going to be locally driven or international? Will he need employees—his own Geek Squad of sorts—to put out fires when there are emergencies?

And looking toward the future, is he willing to dedicate the next five years to really putting in the hours to set up his company? This way, if he chooses to start a family someday, he can help avoid having to work until midnight as a new dad.

Swift Crosby adds that thinking through these choices now will help Mike craft the ultimate situation for himself.

What Mike Thinks

“I really appreciate the advice. Right now, I’m focused on building clients—and just managed to find two more.

Even better, one is able to accommodate my day-job constraints, knowing that I’m trying to branch out on my own. So I can use these new clients to further build my savings over the next few months.

I have thought through eventual plans for the business and definitely want to grow to the point of having employees. And, ideally, I’d like to expand beyond Ohio. But these plans are nowhere near defined yet.”

Related: Fearlessly Freelance: 6 Experts Tips From People Who Successfully Took the Plunge

“I Want to Start a Photography Business.”


Sonja Salzburg, 33, Quality Control Manager, Fort Collins, Colorado.

Why She Wants to Be Self-Employed

“The thought of working from home—with my dog at my feet and time to check on my backyard honeybees during breaks—is beyond exciting. And not commuting 30 miles each day would also be a major perk.

As for the work itself, my real passion is photography. I have a degree in fine arts, but I took jobs outside that field after graduation. However, I’ve been building up a side business by shooting the weddings of friends and family.

As a full-time photographer, I anticipate working fewer hours, and bringing in the same income as my current salary of about $35,000. And even if I do work as much, at least I’ll be building my own company and doing something that fulfills me.”

How She’s Planning Now for the Leap Later

“As I’ve ramped up my photography, it has helped my bottom line.

My husband, Max, and I now have about six months’ worth of emergency savings. We can easily cover our mortgage. And we rent out an apartment to a tenant.

One potential complication is that Max quit his job a couple of months ago. Since then, he’s been helping me, drawing on his 12 years of experience in marketing and sales. He’s even worked as a second photographer with me at weddings.

Our goal is to create a business we can both work at, while making a good living.

Still, I do worry: If we’re both self-employed, will it be tougher to take out a car or business loan? And is it smart to take out a small business loan now—or should we start small and grow from there?”

What the Career Pros Say

Overall, Cohen feels Sonja is ready to embrace the self-employed life.

“She’s been running a photography side business, which tells me she knows what’s involved and her earning potential,” she says. “And the fact that her husband offers complementary skills is a real plus.”

But Cohen also notes that this is not to say that the couple won’t potentially face some challenges: “In reality, owning your own business is a 24/7 job that can be highly stressful.”

As for Sonja’s worries, Storjohann acknowledges that self-employment status can make borrowing tougher, which is why she recommends building the business organically—rather than opting to take out a small business loan.

“The last thing Sonja needs is to be stressed about whether or not she’ll be able to make a big loan payment,” Storjohann explains. “I’d also urge Sonja and her husband to not get into any credit card debt as they adjust to a variable income.”

Since weddings do ebb and flow, Swift Crosby adds that Sonja could benefit from thinking about a strategic plan for the off-season.

“If there are numbers on paper, it’ll be easier for them to see what the projections look like, compared to how business is actually trending,” she says.

What Sonja Thinks

“This is a relief because I’m ready to leave my job. I know I could be even more prepared, but isn’t that true with everything in life? You’ll be waiting forever if you’re waiting for everything to be perfect.

It’s good to know that we should start small. I’ve been daydreaming about taking out a big loan so that we can do everything we want with the business right away.

Instead, I’m going to put that energy into plugging away step by step. And it’s exciting to know that once I quit, I’ll be able to devote even more time to my business.”

Related: How We Learned to Budget With an Irregular Income

Photo of man at home courtesy of Shutterstock.