Have you ever daydreamed about quitting your job to become your own boss? You're not alone: According to MBO Partners, the total number of self-employed Americans is currently nearing 41 million (31 percent of the U.S. workforce), and last year, Fortune reported that millennials in particular are starting more companies, managing bigger staffs and targeting higher profits than baby boomer entrepreneurs.
But it's not always easy or wise to give up your steady paycheck and benefits to go out on your own. There are a lot of factors to consider before you submit your resignation – but sometimes, your gut just tells you when the time is right.
Before they reached age 35, these professionals made the choice to leave their corporate jobs and dive headfirst into entrepreneurship. Here's how each of them knew it was time to make the leap, and what they've learned along the way. [Quitting your day job? Here's what you need to know about benefits when you're self-employed.]
Stephanie Abrams Cartin and Courtney Spritzer, co-founders and co-CEOs of Socialfly
Stephanie Abrams Cartin and Courtney Spritzer were both working corporate jobs when they started a social media agency as a side project. After 10 months of working eight hours a day and then spending every evening and weekend working on their business, they realized something needed to change.
"We had a steady revenue coming in from our side hustle, and despite the long hours, we enjoyed the work and were passionate about social media," Cartin and Spritzer said. "All of these factors led to our 'aha moment' at dinner one night, where we decided to quit our corporate jobs to focus on our agency full time. We picked a date, handed in our two weeks' notice and never looked back."
One the most significant challenges the duo faced came early on. They had originally launched their agency under a different name, and because of their ranking on Google, they received a cease and desist from a company with a similar title.
"This roadblock at the start of our business was scary, but after consulting with our business attorney and regrouping, we were able to turn the experience into a positive by rebranding to Socialfly, which better represents our goals and attitudes," Cartin and Spritzer said.
Socialfly's co-founders said they've loved the opportunity to build and mentor a team of fellow millennials. As an all-millennial office, the company fosters an environment that caters to the team's talents as individuals and as a whole.
"There is often a negative connotation associated with millennials in the workplace, but we have found ways to motivate our team in new and exciting ways that benefit ourselves as an agency and allow us to serve our clients better," said Cartin and Spritzer.
If you're thinking about taking your business full time, Cartin and Spritzer advised asking yourself if it's something you are still going to be passionate about two, five and 10 years from now. Running your company is a 24/7 job, they said, and there will be many sleepless nights. But knowing you are working at something you love makes it all worthwhile.
"Social media was, and still is, our passion and we are incredibly lucky to work in a field that is ever-changing and continues to fascinate and motivate us every day," Cartin and Spritzer said.
Brian Hart, founder of Flackable
When Brian Hart first created a business plan for his own financial PR agency, he was flat broke and expected to stick with his corporate job for at least another year before he was ready to work on his business full-time.
One day, he received an online inquiry from a firm seeking new PR representation. After realizing his vision was exactly what the firm wanted, he decided to quit then and there to pursue and grow his firm, Flackable.
"Being a business owner at 30 years old … I'll be a player in my industry for the next three or four decades," Hart said. "I'm investing in the talent, technology and innovation needed to thrive in an evolving business landscape. Clients are drawn to that forward-thinking approach, and it gives us a steep advantage over tired competitors."
For Hart, building his team has been simultaneously one of the most rewarding and most challenging aspects of his entrepreneurial journey.
"Hiring your first full-time employee … instantly welcomes new layers of complexity and responsibility. But the moment I found myself becoming more proud and excited about my employees' accomplishments than my own is when I truly felt like a leader," he said.
Hart cautioned would-be entrepreneurs that they need more than a product or service to succeed; they need a vision.
"You need a story that will captivate customers and inspire those around you," he said. "That's how you begin to distinguish yourself from the competition."
Jessica Lawlor, president and CEO of Jessica Lawlor & Company
For years, Jessica Lawlor hoped to one day quit her job and start her own business. She had even been saving money from her side hustle in preparation for the eventual transition. In October of 2015, she finally experienced the moment that convinced her she needed to work for herself.
While driving to a work conference, Lawlor had to pull over on the side of the turnpike to take a catch-up call with her boss.
"[I was] jotting down notes and to-dos from our meeting that happened to take place during the middle of my drive," she said. "I felt scattered, stressed and unhappy. After the catch-up meeting, I resumed driving and called a friend. I vented to her about my work trip and endless to-do list. 'What are you doing?' she asked me. 'Quit your job. Take your own business full time. You can do it. I believe in you.'"
Lawlor had heard these words from others before, but in that moment, they struck her differently. She decided to make her plan a reality. That December, she quit her job and made her specialty communications agency, Jessica Lawlor & Company, her primary occupation.
As a social person who thrives on being part of a team, Lawlor initially had a tough time with how lonely it could get being a solopreneur.
"I never thought I'd miss that office watercooler talk or mindless chit-chat throughout the day," she said. "To combat this, I try to … schedule phone calls or lunch meetings so I ensure I'm still out and about interacting with others."
Even on the tough days, Lawlor feels it's all been worth it to be able to choose her own work and clients. She even has time to work on her blog and pursue side projects like teaching yoga – but she had to adjust her mindset and treat herself like a client to make sure her own projects got prioritized too.
Finally, Lawlor noted that hiring help when you can afford it – or, at the very least, tapping into your network of fellow business owners and industry professionals for advice and opinions – will help your business thrive.
"You can't do it alone. You need a team," she said. "I hired my first team member a few months ago. Two minds are always better than one, and she brings new strengths to the table to make JL&Co even better."
Nicole Pomije, creator of The Cookie Cups
After four years at her corporate job, Nicole Pomije realized there was no more room for her to grow in her career. She had been working for herself on the side, and soon realized she had more potential than she could achieve with her employer.
"I didn't see a future for advancement there for me," she told Business News Daily. "I wanted to explore my own passions. I knew that being on my own without a steady paycheck would be challenging but once I gave my notice, I felt this sense of freedom, and feeling that the sky is the limit. It was."
Although Pomije maintains several entrepreneurial projects, her main focus these days is The Cookie Cups, a dessert business that sells its "cookie cups" online and at local markets and events. She's faced a few common challenges along the way, such as packing, shipping and funding, but she believes each one has been a learning experience that will help in the long run.
Overall, Pomije says she's loved the experience of developing her own new and vibrant brand.
"We have a long way to go and in some respects this is only the beginning, but everything feels like a new and exciting experience when you are building the blocks to a new concept," she said.
Pomije's best advice for aspiring entrepreneurs? Be realistic and understand what you're getting into if you decide leaving corporate life is the right choice for you.
"It won't be easy, but it will be worth it if you stick to your plan and persevere no matter what," she said.
Crystal Richard, president of Crystal Richard & Co.
Crystal Richard loved her job, her team and the company she worked for – and yet, something was still amiss. She was happy, she said, but she knew she could be happier.
"There were all these signs and whispers … telling me that entrepreneurship was my destiny," Richard said. "In the last few months before launching my own company, I wasn't sleeping. I had my first panic attack. I was easily irritable and could pick a fight with my poor boyfriend about anything, any time of day."
Richard finally decided to start her own PR firm, Crystal Richard & Co., after five years of agency life. Despite conventional wisdom that says you should have a certain amount of money saved up before quitting your job – not to mention her student loans, rent and car payments – Richard decided to just go for it sans financial safety net, and figure out how to make it work along the way.
"What I realized is that if you really, really want it, you'll find a way to make it work," she said. "Whether that involves waiting tables or bartending to pay the bills, if you want it bad enough, you will figure it out."
Richard says she's thrilled with the flexibility, freedom and opportunities she has as a solopreneur. As an employee, she would have had to request a day off and prepare her team for her absence if she wanted to travel to an event; now she can just say yes and go. However, she noted that one of the most important lessons she learned is that it's OK to take a break from your business sometimes.
"In the first month … I found myself wanting to work all the time, not because I had to or needed to, but because with the responsibility solely on me to deliver for my clients, I was constantly worrying that I wasn't doing enough," Richard said. "I've since learned that actually enjoying my weekends, taking a vacation or 'me day' is 100 percent possible when you're an entrepreneur as long as you're delivering great work and results for your clients."
For more tips on going full-time self-employed, visit this Business News Daily guide.