7 Questions to Ask Before You Quit Your Job

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Are you ready to hand in your two week’s notice and become your own boss?

Not so fast.

Quitting your job to pursue your business full-time is a dream for many side hustlers, but there are a few things you should have in place before you make the leap.

When I was working in my corporate gig, I probably stuck around longer than I needed to because I’m a little more risk averse. I was out to dinner with my boss in Eureka, CA … and it wasn’t until my second beer I finally got up the nerve to tell him I was leaving.

Since I’d been thinking about it for at least a year, it felt amazing to get that off my chest. But it wasn’t a spur-of-the-moment decision or a triumphant flip-off-everyone-in-the-office-and-make-a-dramatic-exit.

It was the result of 3 years of hustling nights and weeks to build my business (the now-defunct footwear comparison shopping site).

Here are the most important questions to answer before you make the leap.


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1. Are You Quitting “To” Something or “From” Something?

Even if your job is miserable and the very thought of another day in your cubicle makes you want to gouge out your eyes, quitting purely to escape won’t solve all your problems.

Thankfully, this is where your side hustle comes in. Quitting to work on your business is much different than quitting to get away from a dissatisfying work situation without a plan.

It’s the same thing for retirement, and it’s something I think keeps many would-be early retirees still punching the clock. Work has become part of their identity and they’re not sure what they’d do without it — even if mathematically they don’t need the income anymore.

In my case, I wasn’t quitting to escape a job I hated; I was quitting to pursue a business I enjoyed more — and that I thought had way more upside potential.

If you can’t imagine what you’ll spend your time doing after quitting your job, you’re not ready to quit yet.

2. How Much is Your Side Hustle Making?

Before you quit, make sure your side hustle is validated with real dollars.

Some readers are more aggressive than I am, but I wanted to see several months or even a year of my side business earning enough to cover my expenses before I quit.

Some people wait longer — like Shannon Weinstein who had a multi 6-figure side hustle before calling it quits at work.

Others, go all in much earlier than I would have, like Kelan Kline who jumped ship after his side business earned just $50.

If your business is seasonal, making it through a whole cycle would be smart so you can get the full picture.

Writing your own paycheck every month is a big deal — and having a track record of earnings before you leave can ease that anxiety in a big way.

3. How Much Runway Do You Have?

Runway is the amount of cash you have socked away to cover your living expenses while you build your business revenue up to a sustainable level.

Again, I’m more conservative so I like to have at least 12 months of living expenses in an emergency fund. Others are happy with 3 months in savings.

Not sure where you’re at in terms of runway? My 30-Day Money Cleanse will help.

4. Do You Have a Sales Pipeline?

Do you have clients and sales in the pipeline? Do you have a process to acquire more?

Both are essential before you take the leap. This is the only way to secure you have a viable business and didn’t just get lucky with a referral client or two.

In my case, I had a system for building out advertising campaigns for the shoe site, and could see how with more time to dedicate to it, the business would grow. It was proven and repeatable, but just needed more time and attention.

5. Is Your Full-Time Job Preventing You from Growing Your Side Hustle?

It’s easy to sit back and imagine all the great stuff you could get done if you just freed up the 40-50 hours a week you’re pouring into your day job.

And this definitely felt like the case for me.

But is time really the bottleneck? Or with a little creativity, could you get more leverage out of the hours you do have?

At a certain point, it doesn’t make sense to keep the day job. For Nate Jackson, that came when he found out it was literally costing him money to go to work.

6. How Will Your Costs Increase or Decrease?

Becoming a full-time entrepreneur will impact your budget, both positively and negatively. If you plan to work from home, your commuting costs will go down, but your energy bill may go up.

Related: My Home Office and Hardware Setup

When I turned in the keys to my company car (one of the best perks of my old job) I had to go get a new set of wheels and start paying for car insurance. The vehicle purchase was a one-time cost but the insurance was a new ongoing expense.

If your business is location-independent, you might actually be able to recognize a huge cost savings by relocating to a lower cost of living area or an area with lower taxes. It could mean a cool opportunity to explore other parts of the world and run your business from the road.

The biggest wildcard expense for the newly self-employed (at least in the US) is health insurance.

When I first quit my job in 2008, I was able to get decent health insurance for myself for around $50 a month. Today when I look for my family of 4, it’s at least $1200 a month — and that’s for a high-deductible high-coinsurance plan that would really only kick in in the case of a catastrophic illness or injury.

You can use a site like PolicyGenius to comparison shop different plans.

In any case, insurance is a significant expense you have to account for before you make the leap.

7. What’s Your Realistic Worst-Case Scenario?

After you’ve crossed the first 5 items off your kiss-the-job-goodbye checklist, a 6th item to consider is your worst-case scenario.

If everything suddenly comes crashing down around you, what happens? How does that impact your life, your business, and your livelihood?

I know this can be kind of scary to think about, but I think it’s an empowering question because when we really dig into it, the worst-case scenario probably isn’t life-threatening. We tend to make things a bigger deal than they are.

People quit their jobs all the time and the world keeps spinning. People do it who are far less prepared than you are.

So be honest: what’s your worst-case scenario?

  • Do you have to change your business model?
  • Do you have to go find another job?
  • Do you have to move into mom’s basement for a bit?

It might be a bruise to the ol’ ego, but it’s all temporary. And my guess is you’ll be happier having taken the chance than to stay the course and wonder “what if?”

Your Turn

What else what you want to make sure to have in place before your quit?

Stock photo by Neomaster via Shutterstock

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

6 thoughts on “7 Questions to Ask Before You Quit Your Job”

  1. Oh my word! Where was this post when I quit my job back in 2014?? LOL! I struggled so hard, but in my defense, I was utterly miserable, Nick. I felt like I was having a stroke every day when I went into the office. I quit without giving even a one-day notice.

    Now, the struggle was real. It lasted for 3 months; however, if I hadn’t done what I did, I doubt I’d be writing for a living, now.

    Great article. I wouldn’t recommend anyone do what I did.

  2. Currently working on this. I set a deadline for June 1 to be done with my job. But I do have debt to pay off and I’m now contemplating whether I should stay in my 9-5 and finish paying it off before transitioning to freelance full time.

  3. Thanks for a reality checklist. Your point about quitting “to” or “from” is an excellent one. So many of my business owner clients really only wanted to get out of a bad job not start a business. Yes paying off debt is a great way to clear the decks and open up your options. Have a healthy saving account will help new entrepreneurs make better decisions using logic instead of fear and lack.

  4. Very insightful tips. I made a mistake of quitting a job in 2013 and then going into a business i did not fully understand. I lost everything within a year and i was back to employment. so what i did later ,was get a side hustle and run it for one full year before quitting again. this time round it worked.

  5. Great posts and article! Real considerations pointed out before quitting. My question….If I started a podcast that I started to make side money and also became kind of popular socially….how do I keep this from my current employer? Nick how did you keep your employer out of or in the loop before you quit your job? Was it an issue for you to have your sidehustle while working your 9-5?


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