7 questions to help you figure out if it’s time to quit your job to start your own business

There’s a ton of risk. But the potential for reward can be oh so alluring. Answer these seven questions to see if you’re ready for entrepreneurship.

7 questions to help you figure out if it’s time to quit your job to start your own business
[Photo: Ellicia/Unsplash]

Quitting your day job to be your own boss, set your own hours, and make your own decisions sounds like a dream come true for anyone stuck in a job they hate. Striking out on your own sounds like the perfect solution to your workday woes. But, after the initial enthusiasm, the downside starts to sink in. Starting your own business means leaving a regular paycheck and tossing benefits aside. There’s a ton of risk. But the potential for reward can be oh so alluring.


So, how can you tell if it’s the right time to jump ship and start your own business? Try answering these seven questions to see if you’re ready for entrepreneurship:

1. Are your excuses not to do it valid?

You’ve heard it all before from would-be entrepreneurs. “I’d love to start my own catering company when my kids are older, or maybe when I have two years of living expenses saved up, or maybe when I have more time.”

Melitta Campbell, a business coach who specializes in helping women start businesses, says there’s always an endless list of reasons for not starting your business. “Most often, these are excuses, but they will feel like real, rock-solid obstacles to the person in question,” she says. “Statements like ‘I don’t have the time’ are usually hiding some other limiting belief that the person may not be aware of.”

Ask yourself whether your excuses are really valid, or whether they are just masking your fears. To get over excuses, Campbell tells her clients to think 20 years down the road and ask how they will feel looking back at the situation they’re in now. “Will you be happy or will you regret that you put the opportunity off?” she asks.

2. Are you completely obsessed with your idea?

There will always be an excuse holding you back from taking the plunge, but while Campbell says there is never truly a right time to start a new business, the time for you is always right when you have an idea that you can’t get out of your head–something you think about constantly that consumes you and becomes an obsessive passion.


Sometimes, you can feed your passion without quitting your day job. If you can do this, start the business in your spare time and grow it while you learn the ropes and gain clients, perhaps while reducing the hours at your day job as you build your side hustle.

3. Are you primed to grow?

While passion is a key ingredient for any entrepreneurial success, it isn’t enough. To be successful, you also need to have a clear vision and goal, a growth mind-set and a desire to learn as you’ll need to wear many hats as an entrepreneur.

If you have a growth mind-set and are ready to roll up your sleeves and stretch yourself, entrepreneurship may be for you. “Running your own business is an amazing opportunity to achieve more growth and fulfilment than you ever thought possible,” says Campbell. But along with this growth and development comes many uphill struggles. Entrepreneurship is a steep learning curve, so you must be able to handle the stressors as well as the pleasures of growth.

4. Can you handle uncertainty?

Being an entrepreneur means ditching the regular paycheck and embracing an uncertain future. As an entrepreneur, you’ll need to push outside your comfort zone, take risks, and, at times, experience failures. “Entrepreneurship is all about the journey and who you become on your route to success, so you’ll need to be ready to experience new things, get scrappy at times, and enjoy the prospect of figuring out how to make the impossible possible,” says Campbell.

5. Do you love to network?

Successful businesses typically don’t exist in a vacuum. “Even if you plan to be a solopreneur, you will need to build a network, connect with potential partners, build a support circle, be visible in the marketplace, and make authentic connections with your prospects and clients,” says Campbell. Even before striking out on your own, join a professional networking group, attend conferences, and shake hands with as many people as you can to build your professional network.


6. Can you support the cost?

Starting any business is usually a costly endeavour. Consider whether you have a cushion to get you through the startup phase and deal with the financial ups and downs that come with starting a new business.

7. Are your expectations realistic?

Many people believe that being their own boss and being in charge of their own hours means they’ll have more time for family and their social life. Freedom, Campbell says, is the most common reason people say they want to start their own business. “In theory you have all the time in the world when you are your own boss, but you also need to be disciplined, focused, and be a master of time management,” she says.

But running your own business means you will need to do some things that you don’t love. You may be able to hire out those tasks, but in most cases entrepreneurs have to wear all the hats until they gain momentum in their business. To find out whether your expectations are realistic, seek out a mentor or someone doing what you want to do and ask yourself whether it’s really the path you want for yourself.

About the author

Lisa Evans is a freelance writer from Toronto who covers topics related to mental and physical health. She strives to help readers make small changes to their daily habits that have a profound and lasting impact on their productivity and overall job satisfaction