357: When To Shut Down Your Business Or Quit Your Job With Steve Chou

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Knowing when to quit your job or business comes down to answering eight specific questions, assigning each a score from one to ten, and adding them up. A total under 20 means leave now, between 40 and 55 is a genuine judgment call, and above 55 means your situation is better than it feels.

In this solo episode I walk through the exact framework I use, which applies equally to relationships, projects, and marketing strategies.

Below are all eight questions with how to score each one, the scoring bands, and what to do when the number lands in the ambiguous middle.

Key takeaways

• Write everything down. The framework does not work as a thought exercise.
• Assign a number to every answer. Numbers force clarity your gut cannot.
• Quitting is not always giving up. Sometimes it is a pivot or a mindset shift.
• How often you think about quitting is the single best indicator.
• Build a backup plan for every bad outcome to remove fear from the decision.
• Weight the questions that matter most to you. Health and family carry more for me.
• Under 20 means leave now. Between 40 and 55 is a real judgment call.
• Give anything three to five years before concluding it will not work.

How to use this framework

Write every answer down and assign each one a number, because this does not work as a mental exercise.

Every question below has to be typed or handwritten into a document, with a score from one to ten attached.

The reason numbers matter is that they let you quantify and justify the conclusion before you act on it. Gut instinct is useful and does not always know the answer.

Two framing points before starting. Quitting does not necessarily mean giving up, since sometimes moving on is a pivot or a change in perspective. And most of us carry baggage we tolerate because we are afraid to disturb things.

Here are the eight questions in order: is it limiting your growth, have you genuinely tried, does it spark more joy than frustration, is it damaging your health, does it compromise your beliefs, how often do you think about quitting, what is actually keeping you there, and is it too late to change your attitude.

Question 1: Is it limiting your growth?

Ask whether you are settling for something with a low ceiling that does not use your full capability.

For a business, the test is sustainability. Selling cheap imported goods through AliExpress dropshipping with no quality control might produce a few dollars, and it is not a business that grows.

For a job, the test is learning. Are you going through the motions for a steady paycheck, and can you see yourself growing where you are?

Nathan Barry is the example worth studying. He was earning a healthy six figures selling courses and ebooks, decided he wanted to build something bigger, shut it down, and started ConvertKit.

Score it: Write down whether your business or job offers the potential to grow and challenge you fully. Score one to ten, where ten means you are genuinely being challenged.

Question 2: Have you put your best foot forward?

Ask whether you have genuinely tried to improve the situation or are giving up at the first difficulty.

Most people cannot answer this objectively about themselves, which is why a neutral third party matters here.

The pattern I see constantly is people insisting they have tried everything. One reader told me it was impossible to start an ecommerce store and that she had exhausted every marketing strategy. Her site had spelling errors, grammatical mistakes, and poor photography, so the basics were never completed.

The standard for having genuinely tried: you have overcome at least a couple of major obstacles and you have sought outside help.

The same applies to a job. Have you spoken to your manager about other roles that might suit you better?

Why this matters is regret. Knowing you tried is what lets you leave with a clear conscience.

Score it: Write down whether you put your best forward or whether untried avenues remain. Score one to ten, where one means you have genuinely tried everything and ten means you have not tried much.

Question 3: Does it spark more joy than frustration?

Ask whether you are still enjoying the journey, since you are probably reading this because you are frustrated.

The question is whether positives outweigh negatives and whether your time is worth the stress.

Both directions of this have played out for me. My businesses were making four times my salary and I still debated quitting my job, because I loved the work enough to accept commuting to an office. I eventually left at eight times.

The reverse happened with the store. We had no sales for the first few months and shutting down crossed my mind, and I was learning enough and enjoying it enough to stay.

Score it: Write down whether it provides more enjoyment than stress or the reverse. Score one to ten, where ten means it sparks joy.

Question 4: Is it damaging your health?

Health here means your physical health, your mental health, your marriage, your friendships, and your relationship with your children.

The first step is deciding how much you actually value each of those. Plenty of entrepreneurs claim family comes first and behave otherwise, and others sacrifice their own health to protect their business and family.

Knowing what you genuinely value is what makes this question answerable.

Then ask how much staying is costing you across those dimensions.

Score it: This needs only a number. Score one to ten, where ten means your situation does not affect your health at all.

Question 5: Does it compromise your beliefs?

Ask whether you believe in what you are doing, because money quietly pulls people into decisions they would not otherwise make.

The slippery slope is real. People make choices purely on financial grounds without weighing the effect on other people or the environment.

The hypotheticals make it concrete. A successful diamond business where you later learn the supply chain exploits women and children. An employer dumping toxic waste into the ocean.

Derek Halpern is the real example. He ran a profitable entertainment news and gossip business, decided it did not make him feel good, shut it down, and now runs a multimillion dollar health food company at Truvani.

Score it: Write down whether your work adds value to the world and you believe in it, or whether you could do better. Score one to ten, where ten means you feel strongly about what you provide.

Question 6: How often do you think about quitting?

This is the single most reliable indicator, and it is worth weighting heavily.

The question is frequency. Every minute of every day, or occasionally once a month?

What matters underneath is how the situation makes you feel. Does thinking about it put you in a bad mood, ruin your day, or keep you awake?

Negative thoughts consuming your mind constantly is a leading indicator that you need to leave.

Score it: A number only. Score one to ten, where ten means you rarely think about quitting and one means you think about it constantly.

Question 7: What is actually keeping you there?

Identify the fear holding you in place, then plan for the outcome you are afraid of.

The common versions: people stay in draining jobs because they do not know how else to earn money, or lack confidence they could succeed independently.

Obligation traps others. A friend of mine helps run her family business despite hating it, because she does not want to disappoint her parents and avoids confrontation. Another runs a business with a friend who is not pulling her weight, where leaving risks the friendship.

The method for fear of the unknown is enumerating outcomes. Ask what actually happens if the business fails completely, then build a plan for it.

Our backup plan when we started Bumblebee Linens was going back to work. That is unglamorous and it removed the fear entirely.

Score it: List every possible outcome with a plan for each, then score one to ten, where ten means the consequences of quitting are dire and one means quitting is not a big deal.

Question 8: Is it too late to change your attitude?

Ask whether you can still see the situation clearly, because resentment makes objectivity impossible.

The same circumstances support two completely different readings. When our sales were nonexistent, I could have concluded nobody would ever buy handkerchiefs. What I concluded instead was that the money was not where I wanted it yet and I was gaining skills that would benefit everything else.

Frequently we want to quit because our mindset has already left. If you are angry or resentful, you have effectively given up and can no longer assess the situation fairly.

Before deciding, list every positive of staying. Seeing potential benefits written down sometimes reframes the whole problem.

Score it: Write down whether you are analyzing with a clear mind or whether anger will be difficult to overcome. Score one to ten, where one means maximum resentment.

How to score your total

Add all eight numbers for a total out of 80.

Weight the questions if the flat total does not reflect reality. I always give extra weight to the health question, because my family’s wellbeing and my own outrank everything else.

What to do with a score between 40 and 55

Ask whether you are willing to live at 50%, and whether you can see a genuine path to 90%.

If a realistic route exists from where you are to substantially better, stay and do the work.

If the situation is already toxic, leave.

The broader point is that the act of writing these answers down produces clarity on its own. In most cases the tally is unnecessary because the responses already told you.

Fear should never be the reason to stay. The worst outcome available is spending another year having your soul drained, and never finding out what you were capable of.

My own rule of thumb is giving anything three to five years before concluding it will not work.

Frequently asked questions

How do you know when to quit your job or business?

Score eight questions from one to ten and add them up: growth potential, whether you genuinely tried, joy versus frustration, health impact, alignment with your beliefs, how often you think about quitting, what is keeping you there, and whether your attitude can still change.

What score means you should quit?

Under 20 out of 80 means leave now. Between 20 and 39 means you most likely should, after waiting a few weeks to confirm. Between 40 and 55 is a genuine judgment call, and above 55 suggests staying and working to improve it.

What is the best indicator that you should quit?

How often you think about quitting. If negative thoughts about your job or business consume your mind constantly, ruin your mood, or keep you awake at night, that is the clearest signal available.

How do you know if you have really tried everything?

You have overcome at least a couple of major obstacles and sought outside help. Most people cannot judge this about themselves, which is why a neutral third party matters. Many people who say they tried everything never completed the basics.

How do you get past the fear of quitting?

Enumerate every possible negative outcome and write a plan for each. Our backup plan when starting our store was returning to work. Having a concrete plan for the worst case removes fear from the decision entirely.

Does quitting mean giving up?

Not necessarily. Moving on is sometimes a pivot or a change in perspective rather than an ending. Nathan Barry shut down a healthy six-figure course business to start ConvertKit, and Derek Halpern closed a profitable business he no longer believed in.

How long should you give a business before quitting?

Three to five years as a general rule, unless the situation is genuinely toxic or damaging your health. Most businesses take years to work, and quitting at the first serious difficulty means never learning whether it would have.