The Moment 11 Entrepreneurs Knew It Was Time to Quit Their Jobs

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Making the decision to quit your stable job for the dream of starting a business is daunting to say the least. Yet it’s a decision so many successful entrepreneurs have had to make at some point. Unfortunately, there isn’t a one-size-fits-all answer for when you should quit your current job. The decision requires evaluating yourself, your finances, your passion for your current job and your passion for going out on your own. In order to help with this crucial decision, Seek Capital talked to 11 entrepreneurs on when they knew it was time to quit their jobs and start their business.

1. When You Run Out of Time

“I knew that it was time to quit when I realized that I reached an endpoint in terms of what I could do in a single day. I had a company for web design and at the end of the day, there was only a certain number of clients that we could take on in a month. The income was more or less predictable. It simply wasn’t fun anymore and I didn’t feel like I was growing,” said Adam Hempenstall, founder and CEO of Better Proposals. “That’s why I launched my own SaaS company — the promise of having more personal freedom while the business works (almost) on autopilot was amazing to me. I took the risk and 10 years later, becoming my own boss is the best thing I’ve ever done. Nowadays I can make enormous profits one month and nothing the next month — the stakes are higher and the thrill is bigger.” Study Reveals: The Best States to Start a Business

2. When You Have a Life-Changing Event

“When I had my first baby, I was working a demanding job with a long workweek. I barely ever made it home for dinner, and I’d only get to spend an hour or two with my child before bedtime each night. He was around seven months old when I started to have nightmares about missing his soccer games and not being there when he learned how to ride a bike,” said Barbara Nevers, founder of Neolittle. “After a month or two of those nightmares, I eventually decided to quit and start a business at home. Now my schedule is more flexible, and I can work while he’s sleeping.”

3. When You’ve Found the Right Idea

"In 2016, the height of the political season, I was actually freelancing outside of my advertising job for non-profits here in NYC, mostly LGBT focused ones, shooting their events, and doing websites. And the clients asking me for more resources, ‘Do you know any developers, grant writers or social media people?’” said Rachel Renock, founder and CEO of Wethos. “And at the same time, I was in advertising, and I had an incredible circle of creatives who wanted to solve problems that mattered. I ended up quitting my job in advertising with my two co-founders, Claire and Kristen. And we launched a beta a month before the election.”

4. When Your Current Employer Supports You

"I worked as a freelance web developer starting at 15 years old, and when I was 20, I moved to Florida to begin working for one of my clients full-time. Prior to taking the job, I told him about my side hustle, an e-commerce business selling magazine subscriptions including USA Today, Maxim, and Wall Street Journal. The e-commerce business began to take off about six months after I moved to Florida for this new full-time job,” said Greg Van Horn, co-founder and CEO of FinanceBuzz. “This was the first time I was living away from home, with my own apartment and all the bills that come with it, but I was 20 years old and the e-commerce business was generating in one month what my job was paying me in three months. I went to talk to my then boss and he said, ‘You can always get another job. If you have a business that’s working, that’s rare. You 100 percent need to go do it.’”

5. When Your Side-Hustle Income Exceeds Your Salary

"Quitting my job was one of the hardest decisions I have ever made, but [it] also turned out to be one of the best decisions. Working my day job while building my real estate company was taxing, but necessary for a period of time. Once my income from my side hustle became almost as much as the income from my day job, I knew it was time to make the switch,” said Joe Horan, owner of Wrightwood Homes. “Real estate was something that I was passionate about, and my day job was not. Now that I have fully committed to my passion, my company has grown significantly compared to when I was doing both jobs. My advice: Fully commit to your side project once it generates you a livable income. Until then, you may have to work longer hours than you’d like. It will be worth it." See: 7 Fears to Overcome Before Starting Your Business

6. When You’re Enthusiasm Shifts

“I knew it was the time to quit my job and start my own company when everything started suffocating me. Nobody likes to be micromanaged, and I think for the greatest part of my career, I was micromanaged. I always had ideas and was pretty enthusiastic about working,” said Darko Jacimovic, co-founder of “Actually, I don’t believe people who say they only work for a paycheck. We spend the major part of our day at work, and I always strived to use this time to do something meaningful and to enjoy it. When I realized nobody would give me as much liberty as I need if I don’t do something, I decided to take a leap and start my own business.”

7. When Your Boundaries Disappear

“I had a problem with 9-to-5 working time and working in an agency often means you’re available 24/7. This is how I ended up responding to emails, checking client’s Instagram and Facebook accounts past my working hours, and slowly the line between personal and professional life has faded,” said Raj Vardhman, co-founder of GoRemotely. “I was always tired and started dreading going to work. To make things worse — I used to love my job. This is how I decided to work freelance and manage my schedule how I see fit. In the end, the list of my clients grew I was able to open a business, and now I’m trying to help other remote workers find the best jobs on the market.”

8. When You Decide What Your Legacy Should Be

“Before I founded my charity, I was facing the question of what professional legacy I would leave behind. Fifty years from now when I looked back on my life, would I have harnessed my skill set towards making a unique social impact? I asked myself this question over and over,” said Shyam Krishna, founder of SKI Charities. “When I finally decided on the idea of social entrepreneurship through SKI Charities, I quit my day job and my breakthrough was achieved. Nine years later my team and I are empowering hundreds of females and their families in the most isolated parts of our world through microfinance and scholarships.” Read: Top Traits of Successful Entrepreneurs

9. When Your Gut Tells You the Time Is Right

“I quit a $100,000 job in January this year. I didn’t have an already-flourishing side gig to step into, but I had an entrepreneurial itch to scratch, and it was now-or-never. There was a wave of change breaking in the industry I wanted to work in (the science of learning for exams at school and university) and I needed to catch it, plus as a married 29 year old, this was my moment to build something great before starting a family,” said William Wadsworth, founder of Exam Study Expert. “I’d tried to get the business going alongside my career but lacked the time and headspace to make any meaningful progress. Quitting was the only way, and nine months [in, it] was 100 percent the right decision — my baby business is starting to grow up nicely.”

10. When You Still Don't Feel 'Ready'

“I got to the point where things started to work in my business, but I just couldn't devote as much time to it as I wanted. Did it fully replace my corporate income when I quit my day job? No, not immediately. But I also had to ask myself, what would be possible, if I'd free up an additional 45 hours per week from my day job and commuting to work,” said Susi Kaeufer, founder and CEO of Dreamlife Deluxe . “After I quit — not only my day job but also my apartment lease — to take my business full-time and travel the world, things got momentum and I made my first $100,000 within eight months. That's when I knew, not waiting until you feel ready and secure was the right move.”

11. When You've Completed Your Homework

"I was working as a manager for a major Canadian bank when I decided to quit. For a while, I struggled with whether it is right to quit a stable well-paid job for an uncertain venture. Before quitting, I studied the idea and consulted experts for a year,” said Hanif Bayat, founder and CEO of Wowa Leads Inc. “When I was done with my research, there was no doubt in my mind. I needed to quit my job so I could spend enough time on the business, raise money, and gather a team. I waited for my end-of-year bonus and quit in January 2018. It’s one of the best decisions I ever made."

The Bottom Line

Even if you don’t have a full business plan laid out, or are uncertain if you’re fully ready, quitting your job to start a business can still be the right move. Obviously, it depends on the person, but if you’re fed up at your 9-to-5 and have a passion for something beyond, tapping into your inner entrepreneur could be your ticket to newfound success. What all these entrepreneurs share is the idea that, even if their own new business fails, they have hope that it is better than remaining at an unfulfilling, stable job. More From Seek

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