Is It Time To Dramatically Quit Your Day Job?

Gwen Dean quit her day job to become a self-employed puppeteer in front of millions during this year’s Super Bowl. Dying for a dramatic exit? Before you throw in the towel to chase a dream, ask yourself these five questions.

Is It Time To Dramatically Quit Your Day Job?
[Image: Flickr user MIKI Yoshihito]

In 2013 the showiest way to quit your job was with an after hours dance to Kanye West. But on February 2, 2014, New Yorker Gwen Dean upped the ante. On a Super Bowl commercial for GoDaddy, she quit her job of 18 years to become a self-employed puppeteer. She told her boss, Ted, “Ciao baby,” with the help of a blue fuzzy bird.


Trading in a machine engineer’s license for a cast of characters made of foam, fur, and feathers sounds a bit extreme. Did Dean make a mistake?

“Absolutely not; I’ve had no regrets or second thoughts,” she says. “When I make a decision, I tend to analyze until I’m paralyzed. I was ready.”

Dean discovered her true passion lay in puppetry in 2006 when a friend asked her to help out with a show at a local hospital. Dean fell in love with the art. She started reading books on puppetry, made her own characters, and joined puppet guilds. Then she had a revelation: “This could either be the world’s most expensive hobby, or I could start charging for shows,” she says.

She ran a small business on the side, entertaining kids at daycare centers, hospitals, and birthday parties, until her day-job hours were shifted and she could no longer do both. Then fate stepped in: “I saw a blind ad looking for a puppeteer who wanted to quit their day job,” she says. “It’s as though I had wished upon a star.”

Turns out, GoDaddy had an idea for a Super Bowl commercial that would feature someone in a creative field quitting their job on live national television to pursue their dream. Dean was chosen, and she hasn’t looked back. She’s in good company; 48% of Americans dream of starting a business, according to research by UPS, but half of small businesses fail within the first five years, according to the Small Business Administration.


How do you know if you should follow Dean’s lead and quit your day job? It depends on your threshold to pain, says Kevin Johnson, author of The Entrepreneur Mind: 100 Essential Beliefs, Characteristics, and Habits of Elite Entrepreneurs “Those who can withstand the ups and downs and keep going are ultimately the best suited,” he says.

Dean and Johnson say there are five questions you should ask to see if you’re ready to quit your day job:

1. What are my responsibilities?

If you have a mortgage, kids and student loans, it may not be time to start your own company, says Johnson. But if your household has a second income or you’ve saved enough money to live on for a while, it might be a good idea.

“The fewer the responsibilities you have the better,” Johnson says.

2. Do I have a sense of adventure?

If you’re dreaming of starting a business because you don’t like your job, find another job, Dean says, but if you have an idea, let it grow.

“Running a business is like going through life with just what’s in your backpack,” Dean says. “You need to be able to think outside the box, inside the box, through the box, and while standing on the box. You must be up for a wild ride.”


3. Does my idea sell?

Johnson suggests testing your idea to see if it sells. Set up a website. Test your product sales online or through sites like eBay or Amazon. Get a booth at a trade show.

“See if people will pull out their wallets and invest in you or your idea,” he says. “If it doesn’t make money, it doesn’t make sense.”

4. Did I do my research?

Hit the books, says Dean. You have to have passion for it.

“It shouldn’t feel like drudgery to read three books a week on this topic,” says Dean, who studied everything from show business to copyright law and accounting. “If you want in bad enough, make it your business to know everything about it.”

5. Am I willing to go all in?

While it took Dean nearly eight years to make the leap, Johnson encourages people to leave their job immediately to make their small-business idea work.

“You have to be 100% in,” he says. “Having one foot in your job and another in a small business means you aren’t doing either effectively. By going out on a limb, you put pressure and expectations on yourself, and you set the environment for success.”


Another option is to take a leave of absence. “It’s a good middle ground for someone who isn’t sure,” he says. “It allows you to devote a lot of time to see if your business will work.”

Johnson advises that you leave your job on good terms. “They could become a client,” he says. “Or you may have to go back.”