• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
LeadershipAsk Annie

When to quit your job and start your own business

By
January 15, 2015, 2:36 PM ET
quit
I quit message on office doorPhotograph by Bill Varie—Getty Images

Dear Annie: I’ve been in my current job for about five years, and not only do I dislike what I’m doing, but our department got a new boss a few months ago who drives me crazy. He has no integrity, encourages us to take shortcuts that do a disservice to customers, and second-guesses every decision anyone on my team makes.

I’ve always wanted to start my own business, and I think I have a solid idea for a company. The thing is, I read your column mentioning the high rate of failure among startups — the ones we never hear about — and I’m debating with myself over taking the plunge. How do you know if you’re really ready to run your own company? — Thinking It Over

Dear Thinking: Good question, especially given the current IPO gold rush, which is creating a whole new batch of overnight-millionaire entrepreneurs. Still, your main motivation right now seems to be getting away from your terrible boss, and that sets off some alarm bells.

“You never want to start a company as a reaction to a bad situation,” says Ashish Toshniwal. “You need to have an idea you are really passionate about, or you’ll never make it through the first couple of years, which are extremely tough.”

Toshniwal has been in your shoes. About six years ago, at 26, he was unhappy in his job as an engineer at Dell. At the same time, he and a friend, then-Yahoo-engineer Sumit Mehra, were building Facebook apps for fun in their spare time. When smartphone technology came along, the pair quit their jobs to launch Y Media Labs, which now develops mobile apps for PayPal, eBay, Bank of America, Symantec, and many others. The company has grown from the two founders to 141 employees, and Toshniwal expects to hire about 80 more staffers by the end of the year.

“We were really passionate about this new technology, and we saw an inflection point, where growth was just about to take off,” he says. “Wanting to leave an unchallenging job, or any particular boss, was never the motivation.”

It shouldn’t be for you, either. “You have to start with what your true passion is, and then work backward and find a way to pursue it,” says MJ Gottlieb. “You might find that’s by getting a different job, rather than starting a business.” Gottlieb is the author of How to Ruin a Business Without Really Trying, a compendium of 55 mistakes he made while starting and running six successful companies over the past 23 years. “Above all, don’t quit your job because you believe you have a great idea for a business,” he adds. “An idea is not enough.”

So, what is enough, then? Consider your answers to these four questions:

  • Do you have any evidence that your idea will fly? Too many entrepreneurs start companies without doing enough research, or asking enough hard questions, to make sure their product or service is “something that people actually want or need, and that will entice business away from competitors,” says Gottlieb. “Especially if you hope to attract investors, you need customers and revenues. Nobody funds an idea.” One way to try out your business without quitting your day job: Build your company on the side, in your spare time, until you know for sure it can survive in the marketplace.
  • Are you ready to be flat broke for a couple of years? Toshniwal and Mehra funded Y Media Labs with their own savings and credit cards, and then took no cash out of the venture for the first two years while they built a solid customer case and refined their mobile-app technology. “We lived a very frugal life,” says Toshniwal. “In fact, we took such a hit financially that we almost gave up.” This isn’t everyone’s cup of tea. Notes Toshniwali, “If you work for someone else, you always get paid no matter how the business is doing.” Not so with a startup.
  • Are you good at solving problems and overcoming obstacles on your own? One thing Toshniwali missed after he left Dell was the enormous corporate support system he had always taken for granted. “As an employee, you have access to the company’s resources. You can usually assume your manager or someone else will take care of details and problems that get in your way,” he says. “In a brand-new enterprise, it’s just you doing everything — while being under intense pressure to produce results.” This is why it’s not unusual for exhausted would-be business owners to run back to a cubicle somewhere.
  • Would you mind giving up a life outside of work? And, if you have a family, how do they feel about it? “As an entrepreneur, you’re always on call, including nights, weekends, and holidays,” notes Gottlieb. “I’ve had to miss a lot of birthdays and events, and let down a lot of family and friends. At one point, I realized I hadn’t taken a vacation in 14 years.” In what has to be in the running for Understatement of the Year, Gottlieb adds, “The life of an entrepreneur is not in everyone’s DNA.” Many entrepreneurs — including those who have real-life, flesh-and-blood spouses or significant others — say they feel married to their companies.

If your honest answer to all four questions is “yes,” then go for it. But if any of the four (or more than one) gives you pause, think about looking for a different job — maybe even inside your current company, but with a better boss — instead. Good luck.

Talkback: If you’ve ever quit a job to start a business, what was the biggest adjustment you had to make? Leave a comment below.


Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

AI promises to free workers from grunt work, but psychologists say those mindless tasks are exactly what our brains need to recover
AIworker productivity
AI promises to free workers from grunt work, but psychologists say those mindless tasks are exactly what our brains need to recover
By Marco Quiroz-GutierrezApril 11, 2026
20 minutes ago
Three people sit behind a desk and look at the phone screen of the person in the middle.
Future of WorkConsulting
Meet ‘trendslop,’ the new, AI-fueled scourge of workplace consultants everywhere
By Sasha RogelbergApril 10, 2026
11 hours ago
A young man looks at his phone, and a flurry of red arrows point downwards.
Cryptosports betting
Prediction markets have made betting easier than ever—and young men are paying the price
By Carlos GarciaApril 10, 2026
15 hours ago
chick-fil-a
North AmericaImmigration
Why Chinese immigrants to America love Chick-fil-A so much
By Fu Ting and The Associated PressApril 10, 2026
16 hours ago
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf’s $100M club—and donated his entire Ryder Cup stipend to charity
SuccessGolf
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf’s $100M club—and donated his entire Ryder Cup stipend to charity
By Sydney LakeApril 10, 2026
17 hours ago
United Airlines CEO Scott Kirby
SuccessThe Interview Playbook
United Airlines CEO judges candidates by whether pilots would want to go on a four-day trip with them: ‘If you say no, then they’re out’
By Emma BurleighApril 10, 2026
17 hours ago

Most Popular

Mark Cuban admits he made a mistake letting go of the Mavericks: 'I don't regret selling. I regret who I sold to'
Investing
Mark Cuban admits he made a mistake letting go of the Mavericks: 'I don't regret selling. I regret who I sold to'
By Fortune EditorsApril 9, 2026
2 days ago
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf's $100M club—and donated his entire Ryder Cup stipend to charity
Success
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf's $100M club—and donated his entire Ryder Cup stipend to charity
By Fortune EditorsApril 10, 2026
17 hours ago
Schools across America are quietly admitting that screens in classrooms made students worse off and are reversing years of tech-first policies
Innovation
Schools across America are quietly admitting that screens in classrooms made students worse off and are reversing years of tech-first policies
By Fortune EditorsApril 10, 2026
1 day ago
The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
Economy
The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
By Fortune EditorsApril 9, 2026
2 days ago
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
AI
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
By Fortune EditorsApril 9, 2026
2 days ago
The Navy confirmed an ‘abundant amount’ of Uncrustables when the Artemis II crew lands. Smucker’s just offered them a lifetime supply
Politics
The Navy confirmed an ‘abundant amount’ of Uncrustables when the Artemis II crew lands. Smucker’s just offered them a lifetime supply
By Fortune EditorsApril 10, 2026
11 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.