receives compensation from some of the companies listed on this page. Advertising Disclosure


11 Questions to Answer Before Quitting Your Job to Start a Business

Kenneth Burke
Updated Feb 02, 2022

With the right preparation, no business should fail! Work through these questions to put your business on the path to success.

It’s easier than ever to start a business, and that’s great! But there’s a lot to consider before you run off and quit your job. Entrepreneurship is not for everyone – and that’s perfectly fine!

Through my startup experience with Text Request, consulting with brands at all stages, and from simply living in the entrepreneurial world, I’ve seen a lot of failed attempts. Failure is a necessary part of growth, but after working with so many people, I’m convinced no business should fail. We just need to better prepare ourselves!

If you’re looking to start a business – especially if you’re considering quitting your job to start a business – use this article as a worksheet. Taking the time to answer these questions thoroughly will help you avoid common mistakes, and bring you a much higher chance of success. Let’s get started!

1. Why do you want to quit your job?

Every job and every business comes with its own set of problems. If you’re trying to run away from issues with your current job, starting a business will be a rude awakening. If you start a business for the wrong reason, you’ll be worse for it!

If you’re considering quitting your job to start a business for some kind of gain, because you see how to solve a common problem or to become more fulfilled, then you might be on the right track.

Be honest with yourself. Why do you really want to quit your job? Is there an office conflict you could resolve that would take starting a business off the table entirely?

2. Do you know how to start a business?

You can learn anything you want, and you’ve certainly come to the right place for it! Starting a business isn’t all that complicated these days, but you need to prepare yourself before diving in.

Here are a few things to look into:

There’s more that goes into starting a business, but this gives you a taste of what you should be prepared to do.

3. Is there a real market for your business?

The #1 cause of new business failures (accounting for 42 percent of them) is “lack of market need.” I.e. no one wanted to buy the product.

I often see people who want to be trailblazers and create a whole new industry. I appreciate the chutzpah, but 1,000 of these attempts crash and burn for every one that succeeds. Those who already have a market for their business – those who solve a problem – have a far higher chance of success.

Before quitting your job to start a business, do some market research. If there’s not a market, don’t try to force it! Platforms like AYTM and Survey System are great places to start your research. For local businesses, you can also ask around the community to get a feel of things.

4. What kind of effort, work and time will it take your business to start making money?

If you don’t have the right expectations going into your business, you’re going to have a miserable experience. But with the right expectations, you could excel!

Before quitting your job, you need to know what it’s going to take you – not someone else; not an investor or web agency – to get your business off the runway and soaring. How many hours are you going to need to spend, and how much funding is it going to take for you to start bringing in revenue? You’ve got to have a handle on this.

5. How much support will you need along the way (financial or otherwise)?

There are several kinds of support that you’ll want or need as you start a business:

  • Financial

  • Emotional

  • Advisorial

Dollar for dollar, what’s it going to take to support yourself (and your family) as you start this business? Will you need to bring on investors?

Entrepreneurs tend to experience a lot of exhaustion, and they normally have a good support system around them – either some caring friends or a loving spouse. When times are tough, who will encourage and motivate you to keep going?

According to Mark Cuban, “Sweat equity is the best startup capital.” But wouldn’t you also like some help instead of learning everything on your own by trial and error?

People love to help each other out, and it will be in your best interest to find someone whose expertise will help you make good decisions in this next phase of your career.

6. How patient are you?

Growth takes time. Unless you get lucky, the first three years are an all-out grind to understand your customers and build a solid foundation to scale. Can you handle the work when it doesn’t seem to be paying off yet?

Do you have the passion to keep going through setback after setback? It takes a monumental amount of patience and determination to make a business work. If you’ve got that, great! If not, you might want to reconsider.

7. Is the commitment your business will take worth it to you?

Most people who start a business make sacrifices. They give up their comfort, their money, their friendships, their health, their weekends, sometimes even their families. 

The average length of time for a startup to “make it” is seven years. Are you ready for a 7-year commitment to doing the same thing day-in and day-out? If you don’t think all of this effort and sacrifice will be worth it, then maybe you shouldn’t quit your job. Maybe your business should just be a hobby.

8. How will you approach branding?

In my experience, this is the single most overlooked aspect of any new business. Too often, people come up with an exciting name and a reasonably “cool” looking logo. But branding is so much more than a catchy name! Branding is all about the messaging your brand gives through its voice, logo, copy, website, ads – everything. It’s your identity!

Branding is the public-facing side of your business, so it needs to be top notch. Once you have a solid business plan and understand your ideal customers, I’d recommend working with a professional branding agency (or experienced freelancer) to help you create the perfect identity for your new business.

9. Who’s your competition?

Before you jump out of that plane, you need to know the landscape. What are you up against? What’s already available in your market?

The presence of competitors doesn’t mean you can’t compete, or even succeed. However, you can’t expect to win if you don’t know what you’re fighting, so do your research. Find other businesses in your space, and learn what’s working for them. You could even contact some of their customers (testimonials are a great resource) to see what they like and don’t like about your competition.

Implementing this research will save you thousands of hours of trial and error, and will ultimately lead to more money in your pocket.

10. Are you okay with failure?

9 out of 10 startups fail. And even the ones who survive make hundreds of mistakes. How does that make you feel – nervous or excited? If it makes you nervous, then you’re probably someone who’s terrified of failure and so much risk. If you’re excited, then maybe you should actually start a business!

When you start a business, you’re going to mess up more times than you can count. If you’ll feel bad about it every time, you’re going to tire out quickly.

11. What’s stopping you?

Perhaps what I love most about entrepreneurs is their undying passion. You can see it in their eyes. They’ll get beat up, but they won’t slow down. It’s beautiful!

One of the great things about today’s world is that, if you want to start a business, you can. There are plenty of resources available, and plenty of people and programs willing to help you.

The most important part of quitting your job to start a business is being prepared. Do you know what you’re getting into? Do you know what it’s going to take?

 If you’re willing to prepare yourself and take the risks, then – my goodness – what’s stopping you?

Image Credit:

Kenneth Burke
I'm the marketing director for a succeeding tech startup. Before getting into marketing, I was an award-winning sales rep at 2 different companies. I launched my own boutique marketing agency, and have helped dozens of businesses, from pre-launch startups to billion-dollar powerhouses, achieve their goals. And I've already written extensively on these topics for other outlets.