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4 Things to Ask Yourself Before You Quit Your Day Job

(Photo Credit: iStock.com/baona)

“Don’t quit your day job” could be the motto of any new entrepreneur. Setting up a business takes time, planning, and above all, money. Unless you’ve managed to squirrel away most of your salary, it’s normal to head to the office for the day and then burn the midnight oil for your passion project.

Murray McKercher has been in the business of starting businesses for many years. He quit his first major job with Bell Canada International in 1990 to strike out on his own as a consultant. Since then, he’s worn many hats, including first-time executive producer of the documentary Day Job, which was released in 2013.

The film follows three young startups as they navigate the world of funding, family and, for some, failure — a tale close to McKercher’s heart.

“It was a story I thought needed to be told because you see all these great, glamourous things about the startup world, and this was a much more realistic portrayal,” he says. “There’s really good, bad and ugly parts of this process.”

If your spouse isn’t on board, expect a rocky road ahead. “You already have one partner and your business is going to become your other partner." 

—  Murray McKercher

Eventually, you’ll have to make a choice about whether to stay or go, and that time might come before your personal business is rolling in it. Before you kiss your cubicle goodbye, here are four things to ask yourself:

Am I Ready For This?

The startup life is not for the faint of heart. Prepare yourself for long, irregular hours and say goodbye to steady paycheques. Extreme discipline is the name of the game says McKercher. “It is incredibly difficult,” he says, especially for those stradling employment and entrepreneurship.

While the cash flow from your nine to five is great, is it taking away from your focus at the home office? Or are you being unfair to your employer making business plans in your head all day? You should be committed to what you do, and if all you think about is your own business, now might be the time to quit.

But first you should ask...

Are My Friends and Family Ready, Too?

In pop culture, the startup-type is always a bachelor with nothing to lose. But what if you’re a real person with human relationships? If your spouse isn’t on board, expect a rocky road ahead. “You already have one partner and your business is going to become your other partner,” says McKercher. Is your human partner okay with that?

Friends play a role, too. Having a support network is paramount. “You’re working out of your house, no people to talk to,” says McKercher, “you need to engage socially or else you’re working alone.”

Friends and family should also prepare for less time with you. Says McKercher, “There will be sacrifices: time, money, trips.” If you’re not willing to give up summer weekends on the patio and vacations with your loved ones, you might not be ready to be an entrepreneur full time.

Everyone on board? Okay, now here’s a big one...

Do I Have Enough Money?

What is “enough,” really? Six to eight months salary is a common answer to this question, but what you’re really buying yourself is time. Have you paved a long enough financial runway to allow your business to take off successfully? In order to make the leap, you need cash flow, plain and simple.

“It will always take twice as long as you think it’s going to take to figure your business out,” says McKercher. So hope for the best, but prepare for the worst.

Turns out you’re flush with cash. Jealous! Here’s one last thing to ask yourself...

Am I Prepared to Fail?

According to Startup Canada, only half of small Canadian businesses make it to year five, but that data includes businesses with up to 100 employees. Other projections are less forgiving.

If your venture just doesn’t work out will your world fall apart? Is someone relying on you to keep the lights on? Have you chosen to cash in your RRSP while also preparing for a new baby? Consider the timing. According to McKercher, failure is a great way to learn — one of his most memorable ventures didn’t work out at all — but only you know whether you’re in a position to risk it all.

If you can answer yes to all of these questions you might be ready to quit. Just make sure your exit is epic, okay?

Michael Wekerle drops his notebook and pen while on the set of Dragons' Den during episode 15, season 10.