9 Questions To Ask Before You Quit Your Job And Start Your Own Business

Leaving the 9-5 and starting your own business sounds exciting. No boss, no pointless meetings, and full control over your time!

But excitement alone won’t pay the bills. The reality?

Most people who make the leap too soon end up broke, frustrated, or crawling back to another job.

If you want to escape the 9-5 for good, you need a plan.

Before you turn in that resignation letter, answer these nine questions.

They’ll tell you if you’re ready or if you’ve still got work to do.

1. Why Do You Want to Start a Business?

If your answer is "I hate my job"—stop. That’s not a good enough reason.

Hate won’t pay your mortgage or attract customers. You need a real reason.

Freedom? Control? Building something meaningful? Your WHY is what keeps you going when things get tough (and they will get tough).

2. How Does the Business Make Money?

A business isn’t just a passion project. It needs to generate real cash.

• How do you get paid?
• Who’s paying you?
• What’s the business model?

If you can’t explain it in one sentence, you’re not ready to quit yet. 

Which is fine! You can start working on this part during your 5-9 while working your 9-5.

3. Who Is Your Ideal Customer?

Your business exists to solve a problem but who has that problem?

If your answer is “everyone,” you’re already in trouble. 

Think about Apple. One of the most valuable companies in the world with a valuation in the TRILLIONS.

Do they serve EVERYONE? No, tons of people prefer Android phones or PCs.

So if Apple can't serve everyone, neither can you. 

The more specific you get, the easier it is to find, market to, and close the right customers.

4. How Much Money Do YOU Need to Earn After Taxes?

Your business revenue is NOT your personal income. This is a huge mistake beginner entrepreneurs make when calculating their financial goals.

Taxes, expenses, and reinvesting back into growth all take a cut.

If you need $10K/month to live but only bring in $6K after taxes and costs, you’ll be back at a job in no time.

Know your real number before making the jump.

Hot Tip: Use that number and work backwards into what you need for your business revenue goals.

5. Do You Have a "Quit Day" on the Calendar Yet?

Leaving a job is easier when there’s a deadline. Without the urgency of a deadline, you'll push it off longer and be slower to do things to prepare for your exit.

It's human nature to procrastinate when it comes to something we fear or that could cause any kind of pain (financial, physical, emotional, spiritual). 

If you’re serious about starting your business, set a quit date—even if it’s a year from now.

A date forces you to take action, build momentum, and stop pushing it off until “someday.”

6. Do You Have a Financial Foundation (6-12 Months of Expenses)?

Your business will take time to grow.

If you don’t have a financial cushion, you’ll make desperate decisions like undercutting prices, taking bad clients, or going back to a job because you ran out of money.

Aim for 6-12 months of expenses saved before you quit.

Even better is if you can use some of the income from your existing job to pay for services and products to get a head start (website design, coaching, personal branding, etc).

7. Do You Have an Existing Personal Brand Around This New Venture?

Starting from scratch is tough.

If you already have an audience, network, or reputation in your new space, you’ll gain traction faster.

But if you are making a transition from sales to interior design or engineering to basket weaving, it's going to take some time to shift how others perceive you.

If you're swapping fields, then start building your brand now while you’re still employed.

8. What Can You Do TODAY to Start Building Your Business and Brand?

You don’t need to quit to start. I actually recommend in 95% of situations that you don't.

Right now, you can:

• Test your business idea
• Build an audience on Instagram, LinkedIn or YouTube
• Get your first client on the side
• Create content that positions you as an expert

Most people wait until after they quit to start. Big mistake.

Start now, so when you do leave, you’ve got momentum!

9. Is There Money Available to Invest in Products and Services to Accelerate Your Timeline?

Free tools and DIY hustle can only get you so far.

Investing in the right tools, coaching, or mentorship can speed up your timeline and help you avoid costly mistakes.

Do you have money set aside for this? If not, plan for it now. Even better, start using these things in your 5-9 while working your 9-5! 

It will build your confidence and strengthen your resolve for your "quit day".

Final Thought: If You Can't Answer These, Don't Quit Yet

Over 80% of businesses shutdown in the first 5 years and most people give up before the 6 month mark.

That doesn't change the fact that starting your own business is one of the best moves you can make but only if you do it right.

I've started three businesses (and about to start a 4th) and I coach entrepreneurs so I know what will increase your chances of success.

You can do so much BEFORE you ever start going at it full time.

So if you struggled to answer these questions, you’re not ready to quit yet.

And that’s okay. Take the time to get your foundation right, so when you do leave, you never have to go back.

Want help figuring out your escape plan?

Schedule a Discovery Call and let's discuss where you are on the journey and what your goals are.