Knowing When To Quit

3 Key Questions To Shape Your Quitting Criteria

Is the pain of putting up with the tough times worth the benefit of the light at the end of the tunnel?


Knowing When To Quit. 3 Key Questions To Shape Your Quitting Criteria. Cartoon of a man flouncing out of an office saying dramatically "I quit!".

Knowing When To Quit - Overview

Knowing when to quit is an important thinking skill and applies to several areas of your life, notably your relationships and your career and business.

In determining when to quit it is important to be very clear about why to quit.



There is an important difference between quitting a project or a job and quitting a relationship.


  • Quitting a project or a job is about opportunity cost
  • Quitting a relationship is to do with toxicity 







Dealing with the tough times - Quit or Continue?

Here are some general pointers to knowing when to quit:

  • Pain vs Gain - Is the pain of putting up with the tough times worth the benefit of the light at the end of the tunnel?
  • Short Term vs Long Term Strategies - Quitting as a short-term strategy is usually a bad idea because it is usually based on subjective and emotional factors.
  • When You MUST Bail Out Quickly - However there is an exception to this when you have made a commitment to a new project or job, or a new relationship, and realise very early on that you made a serious error of judgement.  In this instance it is a very good idea to bail out quickly before you do yourself and the other party serious harm.
  • Why Quitting For The Long Term Matters Most - Quitting for the long term is a better idea because it frees you up to focus on something more beneficial to your long term interests.
  • There Are Very Large Business Benefits In Pushing Through Tough Times  - In business significant and large benefits accrue to the tiny minority of people who are able to push on through the tough times just a bit longer than most people
  • Your Response To Tough Times Determines Your Ultimate Success -  The achievement of most worthwhile things in life is controlled by how you handle the tough times.
  • Its Nearly Always Fun & Easy In The Beginning - In the beginning, when you first start something - whether in business or a relationship, it’s fun and its easy to stay engaged. The thrill and pleasure of the new relationship or the rapid learning and progress you make in your business  keeps you going.
  • The Long Slog Through Tough Times Is The Route To Mastery - And then the tough times happen and in business this marks the long slog between starting out and mastery, and in a relationship this is where it deepens and puts down deep roots that will sustain it for the long term
  • In Competitive Business, Tough Times Can Be Your Ally - The world of business is competitive and tough times can be your ally. The harder it gets, the better chance you have of insulating yourself from the competition because they too will face the same challenges and many will quit.













Deciding WHEN to quit

A decision to quit based on how you feel in the present moment is most probably the wrong decision.

The best approach to knowing when to quit is to have a pre-determined set of "quitting criteria" which sets out certain key limits and boundaries beyond which you are not prepared to go.



    3 Key Questions To Determine Your "Quitting Criteria"

    1. How much time are you willing to spend?
    2. How much money are you prepared to spend/lose?
    3. How much pain are you willing to put up with?



Be Aware Of These Cognitive Biases

Knowing when to quit involves being prepared to let situations and people go.

Letting go is hard

We are hardwired to hang in, not to leave or quit. You are more likely to stay long past the "sell by date" of a situation or relationship than you are to "jump ship" too soon.

Here are 4 cognitive biases to be aware of and that can hold you back and stop you knowing when to quit:

1. The sunk cost fallacy

You have invested so much time, money and energy that it feels very hard to just write it all off. This fallacy has you focused on inputs that are  irretrievable—and it holds you back from seeing where you might find yourself in the future.


2. Your focus is locked-in on positive cues

Intermittent reinforcement combined with an over optimistic bias  can keep you hanging on way past the point when you should quit.

Intermittent reinforcement occurs when the counter-party is inconsistent in "doling out the goodies".

Often their behaviour is toxic but from time to time they dispense some goodies - which can be tangible of intangible. The nature of the goodies is not important but their effect on our behaviour is very important when it stops us from knowing when to quit and actually doing it.


3. Being thwarted makes the heart grow fonder

When we realize that we’re likely to fail at a relationship or a job we begin to see that goal as even more valuable than it really was initially.


4. FOMO - fear of missing out

FOMO is self-explanatory and can be a powerful cognitive bias that prevents you doing that which otherwise you know you should do - which is quit.






The Business Opportunity Cost

We only have so much time, money and energy so knowing when to quit becomes essential if you are not pursuing your best opportunity to become the best in your field.

In The Long Game we outlined 7 proven strategies, with resources, for playing the long game and becoming "so good they can't ignore you".

Our key focus and core theme of this site is about how to cope with tough times by thinking effectively. In Thinking Fast And Slow we set out a route map with clear pointers regarding how to exercise good judgement and  make good decisions.

This theme is developed further in Improved Decision Making - Use Probabilistic Thinking

If you are experiencing any form of resistance to making the decision to pursue your best opportunity to become the best in your field then please refer to Immunity To Change.






Toxicity In Relationships

Knowing when to quit a relationship whether in business or your personal life is hard.

Over the years I have found that the point at which a relationship becomes toxic is the point at which to quit.

We all have different thresholds of what we find acceptable and can tolerate in relationships.

My own personal view is that when a relationship shows any of the following characteristics repeatedly is the time to end it:

  • People who are "emotional black holes" and what I refer to as "drainers".
  • Narcissistic behaviour - in all its forms and manifestations.
  • Arrogance and rudeness, a selfish lack of consideration.
  • The "never enough" syndrome - no matter how much you give to the other person it is never enough.
  • Repeated crossing of your boundaries.
  • A horrible sinking feeling when their name flashes up on your phone or in your inbox.
  • When the overall effect of being in a relationship with the other person is toxic.

In my experience it can be quite difficult and take time to reach clarity on toxicity in a relationship when:

  • In a business relationship the other party has the power to confer major financial benefit.
  • In a personal relationship the other party is very attractive and charming - a common trait with narcissists.
  • You love the other person and have a lot of emotion / time / money invested in the relationship.







Examples of Toxicity In Relationships

The abusive mentor

Approximately 8 years ago I was new to the commodities business and specifically to the market for refined fuels and crude oils. This business is about bringing buyers and sellers together.

I had a very wealthy and successful Spanish commodity trader who was mentoring me. He was good, but overwhelming arrogant rude and dismissive, and eventually one day I reached the point of no return and called him out for his behaviour. I figured I could find other ways and other people to help me learn the business - which over time I did.

The arrogant, rude and over-bearing business associate

This anecdote has a feature that also appears in the final anecdote below, and that is that over time the other person's  changed dramatically.

In my early association with this South African business man he was friendly and fascinating - a quirky character but interesting. His inter-personal skills were always weak but he seemed appreciative of the information and help that I shared with him.

Then in more recent times during the early stages of the pandemic his attitude to me became increasingly rude and abrasive, put simply he changed, and we would end up shouting at each other and hanging up on calls.

I tried to find out what the issue was and eventually I came to realise that he wrongly attributed certain business weaknesses to my commercial professional performance in our business relationship. I did my best to improve things but after one too many abrasive and rude calls I blocked him on WhatsApp and on my phone and emailed him to explain exactly why.

The breakdown in a long standing loving personal relationship

This anecdote was shared with me by a longstanding male friend.

I have posted a piece featuring this man's pain at losing a much loved woman through her obsession with posting sexualised body pics to exclusively male followers on Instagram in:  Roxanne - I Will Not Share You With 35,000 Other Men

I think this personal tragedy is largely self explanatory, but for context I do understand that the woman's obsession with posting on Instagram was a pattern of behaviour that only developed 5 years into a 6 year relationship.

To conclude, each of the counter-parties to these toxic behaviours undoubtedly had their reasons and perhaps unresolved issues that motivated their behaviour. But there came a point in each of these situations where you can only deal with the presenting behaviour.

The point at which the counter-party's behaviour becomes persistently toxic is the time to quit.






Return from "Knowing When To Quit" to: Mental Models



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