Should I Quit My Job Or Close My Business? Here's When To Move On

Should I quit my job? Should I shut down my business? Should I end a partnership? In this post, you’ll learn the exact questions that I ask myself when deciding whether to move on and pursue something else.

First off, the principles outlined in this post apply to all areas of life. For example, I use this framework for relationships, projects, marketing strategies, everything!

I also want to stress that “quitting” or “moving on” does not mean that you are necessarily giving up. Sometimes “moving on” simply involves a pivot or a mindset shift that can change your perspective or how you feel.

It’s also important to note that we all have “baggage” in our lives (which could be your job or your business) that need to be culled without even realizing it.

We all put up with activities or people who drain us of our energy because we’re afraid to rock the boat.

The framework that I’m about to teach you will help put an end to your misery:) By answering these questions, you’ll achieve clarity and understand exactly what you must do.

But before we begin, I want to emphasize that in order for this process to work, you have to write down everything! Every single question that I’m about to ask you must be typed (or handwritten) in a document.

Also, you must force yourself to assign a number to each of your answers as well! Numbers don’t lie and they allow you to quantify and justify the results in your mind before taking action:)

Editor’s Note: Some of you reading this article are used to using your gut to make big decisions, and using your gut is great. But sometimes your gut doesn’t know the answer. Sometimes, you’re just hungry:)

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Table of Contents

Question #1 – Is Your Job Or Business Limiting Your Growth?

When it comes to quitting your job or shutting down your business, the first (and easiest) question to ask yourself is whether you are settling or compromising your potential.

Are you working at a job or running a business that has a low ceiling and doesn’t exercise your brain to its fullest potential?

For example, let’s say you are selling cheap Chinese junk with your Aliexpress dropshipping business and providing almost zero value to your end customer.

Even though you might be making a few bucks here and there, is selling junk with zero quality control a sustainable business that will continue to grow?

Are you working at a day job where you have stopped learning? Are you just going through the motions at work everyday just for the sake of a steady paycheck?

Can you see your self growing at your current position?

My friend Nathan Barry was making a healthy 6 figure income selling courses and ebooks when he realized that he wanted to work on something bigger.

So he made the difficult decision to shut down his course business and started ConvertKit, one of the best email marketing software companies in the world!

For this question, I want you to write down one of the following 2 statements and assign a number from 1-10(best).

My business or job offers the potential to grow and challenge me to the best of my abilities
My business or job does NOT offer the potential to grow and challenge me to the best of my abilities

Then, give it a number from 1-10 where a 10 indicates that you are being challenged and growing.

Editor’s Note: In the case of relationships, a 10 indicates that the person is good for your personal development and growth.

Question #2 – Have You Put Your Best Foot Forward?

Have you tried your best to improve your situation? Have you done everything in your power to grow your business or are you just giving up at the first sign of hardship?

For most people, the answer to this question can not be answered objectively and you must seek a neutral third party for a real answer.

Over the years, I’ve received countless emails from small business owners complaining that it’s impossible to start a successful ecommerce store.

“I’ve tried every marketing strategy out there. This is never going to work!”

“I tried selling online but every product I could think of had too much competition”

One time, I decided to challenge one of my readers who claimed to have “tried everything”. But when I went to take a look at her website, her online store looked horrible.

There were spelling errors, grammatical mistakes and the photography was terrible. It’s no wonder that her online store was a failure. She didn’t even complete the basics correctly!

So when it comes to putting your best foot forward with your business, you can’t really claim to have tried “everything” until you’ve overcome at least a few major obstacles.

You can’t claim to have put your best foot forward without soliciting outside help.

This principle applies to your day job as well. Have you spoken to your boss to discuss other roles that might be more fulfilling? Before writing off your job or your business, make sure that you’ve given it your all.

Knowing that you’ve tried your best to rectify your situation is extremely important in order to move on in good conscience. There should be no regrets!

Write down one of the following 2 statements.

I have put my best foot forward to make things work.
There are additional avenues I haven’t tried yet to improve my situation.

Then, assign a number from 1-10 where a 1 indicates that you have tried everything in your power.

Editor’s Note: The scale is backwards for this question. A 10 indicates that you have tried nothing!

Question #3 – Is Your Business Or Job Sparking More Joy Than Frustration?

Most likely, you aren’t reading this post unless you are sufficiently frustrated:)

But a simple question to ask yourself is whether you are still enjoying the journey. Are there more positives than negatives and is your time worth the added stress?

When my businesses were making 4X my day job salary(I was making 8X when I finally resigned), I debated whether to quit. But I loved my job so much that I was willing to stay despite the inconvenience of having to commute to a physical office.

When my wife and I started our online store and received no sales the first few months, the thought of shutting it down had crossed my mind. But I was learning so much and having so much fun that I was willing to stick it out for better or for worse.

For this question, write down one of the following 2 statements.

My business or job provides more enjoyment than stress.
My business or job provides more stress than enjoyment.

Then, give it a number from 1-10 where 10 indicates that your business sparks joy:)

Question #4 – Is Your Business Or Job Detrimental To Your Health?

The word “health” for this question can apply to many aspects of your life.

For example, does your business negatively impact…

Your own health (both mental and physical).
The health of your marriage.
The health of your relationship with friends.
The health of your relationship with your kids.

First of all, you have to decide how much you value each of the above. Some entrepreneurs claim to put family and marriage first but then do the complete opposite.

Other entrepreneurs sacrifice their own health to maintain their business and family. The key is understanding what you truly value.

Then, you must ask yourself how detrimental it is for you to stay in your current situation. Is your business or job worth the toll on your mental and physical health?

The answer to this question requires only a number.

Write down a number from 1-10 where 10 indicates that your business or job does not affect your health whatsoever.

Question #5 – Does Your Job Or Business Compromise Your Beliefs?

Money often does strange things to people and excessive greed can sometimes lead to compromise. It’s a slippery slope!

As humans, we sometimes make decisions purely based on the money without thinking about the effects on other people or the environment.

For example, let’s say that you started a successful business selling diamonds but later discovered that millions of innocent women and children were being exploited to mine and produce your products.

Would you be fine with that?

What if the company that you work for is responsible for dumping toxic waste into the ocean?

Sometimes, our business or job silently kills us on the inside. Even though the money is good, you may have to ask yourself whether you are working on a project that you believe in.

Is your business or job turning you into someone you hate?

My buddy Derek Halpern used to run a successful business publishing entertainment news and gossip before deciding that it didn’t make him feel good inside.

So he shut it down and now runs a multi million dollar business selling health food over at Truvani.

For this question, write down one of the following statements.

My business or job adds value to the world and I believe in what I do.
My business or job does not add much value to the world. I could do better.

Then, assign a number from 1-10 where 10 indicates that you feel strongly in what you do or the service you provide.

Question #6 – How Often Do You Think About Quitting?

The answer to this question is often the best indicator of whether you should quit your job or move on from your business.

How often do you think about quitting? Is it every single minute of every day? Or is it only something that you think about occasionally like once per month?

The most telling signal of whether you should quit is how your situation makes you feel. For example, when you think about your business or job, does it put you in a bad mood?

Does thinking about your situation ruin your entire day? Does it stop you from sleeping well at night?

If negative thoughts about your business or day job consume your mind all the time, then that’s a leading indicator that you need to get out of there.

The answer to this question requires only a number.

Jot down a number from 1-10 where 10 indicates that you RARELY think about quitting and a 1 indicates that you think about quitting all the time.

Question #7 – What’s Keeping You In Your Current Situation?

We all do things that we don’t want to do because we’re afraid of the consequences.

When it comes to a soul sucking job, most people work because they don’t know how to make money otherwise. Most people are afraid to quit their jobs because they don’t have the confidence to succeed on their own.

Sometimes, people stay in bad situations out of obligation. I have a friend who helps run her family business even though she hates it. But she doesn’t want to disappoint her parents and she’s afraid of confrontation.

I have another friend who runs a business with a good friend but her partner isn’t pulling her weight. In this case, do you cut ties and risk ruining the friendship?

The best way to deal with situations involving fear of the unknown is to analyze all of the possible outcomes.

If you are scared of quitting your job to start a business, ask yourself what’s the worse that could happen if the business completely failed. Then, come up with a backup plan!

For example, when my wife and I started Bumblebee Linens, our backup plan was to simply go back to work if our business failed.

When you outline and create a backup plan for every possible negative scenario, it makes your decision to move on infinitely easier because it takes fear out of the equation.

So before you answer the question of what’s keeping you in your current situation, jot down all of the possible outcomes and come up with a plan of action.

Then, assign a number from 1-10 where 10 indicates that there are dire consequences for quitting and 1 indicates that quitting isn’t a big deal.

Question #8 – Is It Too Late To Change Your Attitude?

When it comes to every situation in business and life, your attitude determines everything.

For example, when sales were nonexistent for my business in the early going, I could have reacted to my situation in 2 completely different ways.

“It’s game over man. Game over! No one is going to buy these stupid hankies! Screw this!!!”
“This sucks. But I’m gaining many new skills that will benefit other aspects of my life. Even though the money is not where I want it to be yet, I’m enjoying the journey.”

Do you see the difference in attitude?

Often times, we want to quit because our mindset is not where it should be. If you are angry or resentful towards your job or your business, you’ve effectively given up already. You can no longer be objective.

So before you make the decision to give up, try to enumerate all of the positives of staying in your current situation.

Sometimes, seeing the positives and the potential benefits written down in a document can reframe your dilemma in a completely different light.

For this question, write down one of the following statements.

I’m analyzing my situation with a clear and open mind.
I’m angry or resentful with my situation and it will be difficult to overcome.

Then, assign a number from 1-10 where 1 indicates that you’re at max anger or resentment.

Should I Quit My Job (Business, Partnership etc…) Or Not?

If you’ve taken the time to think through all of the questions above (and write it all down), you probably already have the answer you seek:).

But for engineers such as myself, I try to let the numbers do all of the talking.

Take the numbers that you assigned for all 8 questions above and tally them up. If your total is…

Less than 20 – You should get out of there now!
Between 20-39 – You most likely need to quit but delay judgement for a few weeks to make sure your feelings don’t change.
Between 40-55 – Your situation is mediocre, not great and not horrible. It’s a judgement call on your part. But in case you are Asian and reading this, a 55 out of 80 is still a failing grade:) I’d probably still quit.
Above 55 – Your situation doesn’t seem that bad. Stick it out and see if you can get your score closer to 80.

If the numbers above still aren’t providing you with the answers that you need, you can assign weighting factors to make certain questions worth more than others.

For example, I value the health of my family and my well being above all else. So I always give more weight to question #4 above.

If your “quit score” is between 40-55 and you have no idea what to do, here’s my general philosophy. Do you want to go through life living at 50%? Is 50% good enough for you?

If you can see a legit path to raising that 50% to 90% or more in your current situation, then you should stay, suck it up and do the work.

But if your situation is already toxic, then get out of there.

Regardless, the simple act of asking yourself these questions and writing everything down will help you achieve clarity. In most cases, tallying up the numbers won’t be necessary because you’ll just know based on your responses.

But fear should never be a reason not to move on. Because the worst thing that can happen to you is spending another year getting your soul sucked out of you.

The worst possible outcome is not giving yourself the chance to realize your true potential.

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3 thoughts on “Should I Quit My Job Or Close My Business? Here’s When To Move On”

Misty says:

This article could not have come at a better time.
I have been trying to get the courage to leave my job for months, but fear kept standing in my way.
When I looked objectively at what this is doing to my mental and physical health, the answer becomes much clearer, even if it is still a little scary!
Jesse says:

I got the e-mail for this article and wondered if you got tired of me asking you whether my business is fundamentally broken and I should move on. According to your scoring system the answer is… no. Hmm. Seems I’m just a curmudgeon some days.
Anthony Ferrara says:

Really helpful and important post for those who want to make the right decision about switching from a profession to another. Some people don’t think about the future and they do not have any plan for the next movement. just jumped out and can’t be successful and got frustrated. So you need to know the all related thing about moving your career track and this post will help you a lot with this.

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Should I Quit My Job Or Close My Business? Here’s When To Move On