“Winners never quit and quitters never win.”

You’ve been conditioned by the society with this famous quote by the late Green Bay Packers & Washington Redskins NFL coach, Vince Lombardi — especially when it comes to your work or relationships you’ve spent your time, money, and energy on.

But in today’s world where technologies are evolving at an exponential rate and affecting human behavior amongst the masses, operating with the above model of thinking can adversely impact your wellbeing.

By quitting something that’s taking up physical and mental space in your life, you create room to spend your time doing things that fulfill you and truly bring out the best in you.

But knowing when it’s time to quit something before it’s too late and when to keep working at it is a skill in itself. Luckily, I’ve been grateful to have quit over and over again.

I’ve quit so many times that I’ve lost count now.

I dropped out of my Ph.D. program in graduate school. During the same time span of 5 years, I launched and shut down 7 businesses — one of which was in operation for 14 months with 11 team members across 3 continents and we were cash-flow positive (5-figures).

I’ve quit multiple jobs before including 2 startups where I was brought on as a core team member. I’ve left books unfinished at the middle of the read.

Before I started my professional career in Silicon Valley in Technology Sales, I tried my hands at both, Coding and Data Science boot camps and quit.

Recently, I quit in the middle of a 100Km ultra marathon and turned back 80ft from the summit of Mt. Thielsen in Oregon after hiking up for almost 3h gaining over 9000 ft in elevation.

All of these experiences have helped me to develop a framework that you can also use to figure out whether it’s time for you to quit that job you’ve been feeling indifferent towards for a while, or end your romantic relationship which doesn’t have that spark to it anymore or that company of yours you once started with huge enthusiasm to make a positive difference in the lives of others.

Maybe it’s time for you to move on or maybe not. Here’s what to do.

Pre-Work: Before you start assessing whether it’s time for you to quit, you want to make sure you’re familiar with the sunk cost fallacy and that there’s no play for cognitive biases affecting your decisions.


Is this making me unhappy and worse off?

The sunk cost effect is our general tendency to continue an endeavor or continue consuming or pursuing an option when we’ve invested time or money or some resource in it.

That effect becomes a fallacy if it’s pushing you to do things that are making you unhappy or worse off.

Romantic relationships and businesses are a classic one.

The longer you’ve been together with the person or working on the business, the harder it is to end things.

So in order to quit successfully, you’ve got to make sure you’re not falling for the sunk cost fallacy. And then…


What cognitive biases are skewing my decision-making processes?

If you’re a radically open-minded person, you must be aware that we humans can be victims of our own cognitive biases.

Building awareness of the ones that are potentially damaging to your growth and well-being is the key to quitting something successfully.

The most common biases that prevent you from quitting something that is not serving you anymore are:

  • Confirmation bias (my favorite one :-): People believe what they want to believe and do not believe what they don’t want to believe. This makes them seek out information and data that strengthens their ideas and already held beliefs while ignoring and being closed-minded to new information that opposes their beliefs.

Use case: ​Startup founder about to ​go-to-market with the idea. Question to ask:

— “What evidence do I have that this startup/business idea is going to take off?”

  • Loss aversion (my second favorite ;-): In general, people tend to overemphasize their fear of losing something they’ve already put time, money, and energy instead of focusing on the potential gains that could come from quitting it and starting a new thing. Think of your last romantic relationship. If you could go back in time and knowing what you know now, would you end it earlier? That reluctance of ours which makes us stay in a relationship longer than we want is loss aversion in play.

Use case: Finding it difficult to move on in a romantic relationship. Question to ask:

— “How can I be so sure he or she is the only person I need to spend the rest of my life?”

  • Overconfidence bias: Your overconfidence gives you a false assumption that you are superior to others due to the hyper-inflated sense of your personal talent, skill, or self-belief.

Use case: ​Employee demanding a salary raise. Question to ask:

— “What data points do I have that proves I’ve not only over-exceeded the normal duties I was hired for, but my contribution is also making the overall operation of the employer better and it’s fun for others to have me in the team?”

  • Self-serving bias: This occurs when you connect positive outcomes to your skills and negative outcomes to bad luck. Often it’s the opposite thing in play i.e. you got lucky with the positive outcome and your bad skill led to the negative outcome.

Use case: ​Investing in crypto. Question to ask:

— “Am I sure that it wasn’t pure luck as I was able to get in at the right BTC price without knowing much about the technology?”

  • Herd mentality: This is when you blindly follow what everyone else is doing.

Use case: ​Think of the latest health & wellness trend or a viral consumer good. Question to ask:

— “Do I really want or need this product to serve a practical purpose of am I buying this because everyone else has it?”

  • Framing bias: This occurs when you make a decision because of the way information was presented to you, rather than based just on the facts.

Use case: ​Taking up a job at a startup. Question to ask:

— “Am I seeing all the available data about the health of this startup I’m about to join?”

  • Narrative fallacy: We humans are hard-wired for stories. When we come across stories we can relate to, this bias can occur.

Use case: Authors in the self-help genre. Question to ask:

— “So his story is inspiring. But what are the facts and data I can look that verifies his work is delivering real results for people?”

  • Anchoring bias: When you use pre-existing data as a reference point for all subsequent data, which can often skew your decision-making processes.

Use case: Westerners traveling in third world countries. Question to ask:

— “Wait does coffee also cost $5 here in Nicaragua?”

Once you’ve built awareness of any potential cognitive bias that may be skewing your decision-making processes, you need to address them by asking questions that helps you to generate data-points and create the most rational explanation for your decision.

Value #1: GROWTH

How is this still growing?

In life, you’re either growing or dying and staying where you are is you slowly dying.

So whether it’s your business or your relationship or health, it must be in a constant state of growth. Of course, growth is not going to be huge every year. But as long as you’re able to navigate the plateaus in a healthy way and keep growing, you’re on the right track.

A litmus test for growth

Ask yourself: — “What real-world data or examples do I have to verify that this job or relationship or business is continuously growing year over year?”

I like to have at least 1 unbiased objective data-point that shows the sign of growth. Once you’ve evaluated for the presence of growth, you then look for…


What are the contributions truly happening?

The secret of living is in the giving.

If you’re not sure about this, remember the last time you were feeling down but the moment you went out there and helped others — whether by donating your money to a charity or volunteering for an event, you ended up feeling better about yourself.

When it involves more than just you, the contribution has to be from all the involved people.

So before you decide to quit something, do the…

A litmus test for contribution
Ask yourself:
 — “What are my and her/his contribution to this relationship?”

— “How am I contributing to the company’s mission? Do 80% or more of the team members also show up at work wanting to contribute to the mission?”

Growth and contribution are the two factors that maximize human fulfillment.

When you’re growing (whether it’s your business or your relationship or health) and also able to contribute back (your time, energy, money, skills, etc), that’s when you feel most fulfilled and happy.

But there’s also this third value you may want to evaluate for before quitting. That is your…

Value #3: Personal Values

Is this still fun and enjoyable?

The emotional value you’re getting out of something you’ve invested your time, money, and energy into is just as important as to what’s quantifiable or visible to an outsider.

Life is short. Since death is our ultimate destiny, it makes total sense to maximize our time on earth to play and have fun more often, do things that are enjoyable and bring out the best in us.

Of course, we all have our own definition of what’s fun and enjoyable for us.

But if something is making you feel awful or making worse off at the end of the day, it’s time to uncover the root cause of why you’re feeling that way.

A quick litmus test for personal values
Ask yourself these questions: 
— “Am I waking up excited to go to work every morning?”

— “Do I long to spend more time and create memorable experiences with my partner?”
 — “Is working on my business fun and exciting or am I actually stressed all the time?”

So WHEN do you quit? When you can’t fulfill all three of these core values. When your work, relationship, or business has stopped growing (i.e. it has plateaued), when there’s no more contribution to be seen by all the people involved including yourself, and when it just doesn’t feel like worth continuing to keep doing it anymore.

If one is missing, it’s a warning sign to start working on improving that area.

But if all the three values are fulfilled, that’s a sign that you are onto something meaningful — keep doing whatever you’re doing.

Quitting something you’ve spent your time, money, or energy and developed an emotional attachment to it is never going to be easy. But the process of how you go about evaluating whether it’s time to quit something doesn’t have to be hard.

Make sure you understand the sunk cost fallacy. Resolve any of your pre-existing cognitive biases. Set your own values, do a regular sanity check on how you’re living those values, and when they’re in harmony, you’ll be more likely to create more opportunities — for yourself and others to win and succeed.


  1. A cognitive bias is an error in cognition that happens when your line of reasoning when making a decision is flawed because of your personal belief

Originally published at www.ankurmanshrestha.com.