5 Tips to Help You Know When It’s Time to Quit

by Diana Drake

Annie Duke has built a career out of being a deep thinker. She is on track to earn her doctorate in psychology from the University of Pennsylvania. Duke is also the cofounder of The Alliance for Decision Education, a nonprofit that wants to empower students through stronger decision-making skills. And – in an enterprise that perhaps requires her deepest thought and most strategic decisions — she is also a renowned poker player who earned $4 million in tournament poker before retiring from the game in 2012 (many poker champs have advanced training in psychology or behavioral science).

Annie Duke knows a thing or two about when to hold ‘em and when to fold ‘em.

Annie Duke talks with Adam Grant.

During a Wharton McNulty Leadership Authors@Wharton conversation at the Wharton School in Philadelphia, Duke sat down with Wharton management professor Adam Grant to talk about the power of knowing when to walk away, the theme of her latest book, Quit.

“People stick to things all the time that they don’t succeed at, sometimes based on the belief that if they stick with it long enough, that will lead to success,” writes Duke. “Success does not lie in sticking to things. It lies in picking the right thing to stick to and quitting the rest.”

Here are 5 highlights about the virtues of quitting from Duke’s hour-long discussion with Grant, with added context from her book:

1️. Should I grit or should I quit? While these two concepts – sticking with something or giving up on it – are viewed as opposing forces, Duke says that quit and grit are two sides of the same decision. Anytime that you are deciding whether to quit, you are also deciding whether to stick with something. “Grit gets you to stick to hard things that are worthwhile. That’s a really good thing. Everybody should get [Wharton and Penn Professor] Angela Duckworth’s book, Grit. It’s a really important quality to develop in yourself,” said Duke. “But notice I said hard things that are worthwhile. This is the key. The problem with grit, when taken too far — which is our tendency — is to stick to hard things or not hard things that aren’t worthwhile. Why? Because we have a strong bias against quitting as adults.” According to Duke, getting the timing right about when to quit means looking into the future and seeing that the chances things will go your way are too slim.

2️. Timing is everything. A fundamental problem of making the decision to quit is that quitting on time will usually feel like quitting too early. In Quit, Duke writes that we are reluctant to walk away when we should because we have the feeling that doing so will slow our progress or stop it altogether. But by sticking to a path that is no longer worth pursuing – including a stock you’re invested in that’s losing money or a job you don’t enjoy – you are missing out on something that will create more progress toward your goals. “Contrary to popular belief,” said Duke, “quitting will get you to where you want to go faster.”

3️. Monkeys and pedestals. Speaking of making progress, Duke favors a mental model called monkeys and pedestals from Astro Teller, the head of X, Google’s innovation lab, to serve as a guide for quitting sooner. “You have decided you want to make money by training a monkey to juggle flaming torches while standing on a pedestal in the town square,” she explained to Grant. “You should not build a pedestal first. You should see if you can train that monkey to juggle. Why? Because what’s the point? Literally, there’s no point in building the pedestal if you can’t train the monkey to juggle.” Pedestals are the part of the problem you know you can already solve and the hardest component is training the monkey. Tackling the monkey first gets you to “no” faster, limiting the time, effort and money that you sink into a project and making it easier to walk away.

4️. Kill criteria. Quitting has a bad reputation. So much so, that when you’re getting signs that you should quit something, often you dig in and work harder. Anything but quit! Duke suggests that you come up with a list of criteria for killing a project, changing your mind, or cutting your losses; a list of signals you might see in the future that would tell you it’s time to quit. This will help protect you against bad decision-making when you’re in the moment. “In poker, let’s say I’ve lost $2,000, and once I hit that mark, I have to get up and walk away,” she said. “You want to set a limit on how long you can continue to endure the situation that you’re in…Let’s say that you’re in a job where you’re incredibly unhappy and you’re feeling very unfulfilled… What are the signals? What are the things that you’re seeing that would tell you that, no, this is a persistent state and you should not be sticking around?” A common way to develop kill criteria: “If by (date), I have/haven’t (reached a particular state), I’ll quit.” Enlist a mentor – a.k.a. quitting coach – to hold you accountable.

5️. Diversify your portfolio. Just like investors want a diversified portfolio to protect against losses if an investment tanks, people should also embrace the power of options to be prepared for either a forced or voluntary quit. Don’t wait until you are letting go to start exploring your alternatives. “One of the goals for all of us should be to, as much as possible, maximize the diversification of interests, skills, and opportunities in each of our portfolios,” writes Duke, who was forced to stray from her academic course when she fell ill early in her career and soon after took up poker as a way to make money. “Even after you have found a path that you want to stick to, keep doing some exploration. Things change, and whatever you are doing now may not be the best path for you to pursue in the future. Having more options gives you something to switch to when the time is right.”

Conversation Starters

Why does quitting on time often feel like quitting too early?

How do you feel about quitting? Does this article (and Annie Duke’s book) prompt you to think differently about it? Why is quitting an important decision-making skill?

Share your story of quitting in the comment section of this article. How did you arrive at this decision? Were you motivated by “picking the right thing to stick to?”

9 comments on “5 Tips to Help You Know When It’s Time to Quit

  1. In today’s day and age, parents and teachers emphasize the importance of receiving a good education and being successful in life. Although success is subjective and can often have multiple different meanings, I do believe that quitting is a big part of success. To some people, quitting is never an option. They are raised under the impression that quitting is for the “weak” and that it can heavily influence the future an individual might have. However, I disagree with this statement. I believe that every person has a different path towards success but everyone’s path will definitely be filled with rejection and quitting.

    I used to be one of those people, afraid to quit. But through the years, I’ve learned one thing. Sometimes, whether it is academically or personally, holding onto something that you believe will benefit you in the long run does not always happen. Sometimes, holding onto something hurts you more than letting go. For example, let’s say you have this best friend who you are really close to. They know all your secrets and all your favorite things, you guys talk every single day. However, as time passes, you guys slowly begin to drift apart and gradually they begin to enjoy the company of others over yours. To you, they seem to be having a better time with other people as they slowly begin to talk to you less and less. You text them, check on them, hoping to have your best friend by your side. One day, they no longer even acknowledge you when they see you on the streets. This is an example of when it is time to quit. In situations like this, holding on can be more detrimental for your own well being than letting go and quitting. The hard part of this whole process of grit and quitting is knowing when it is the right time to quit.

    Oftentimes, when we quit something, we reflect on this quitting in the future negatively. Many people tend to overlook the good aspects and focus heavily on the negative consequences. They tell themselves maybe if I did not drop out of high school and I did not stay up all night partying, I would be successful. They tell themselves what if I did this a little differently or maybe if I did more of this, I would be more of the person I want myself to be. However, this is the incorrect mindset. I believe that as people, quitting is something that is necessary. As they say, every rejection is a redirection. Sometimes, in your life, you need this redirection in order to be able to grow as a person and to set yourself up to be your ideal self. We often see quitting on time as quitting too early because of the success we see from others and these fake scenarios we make up in our head. Society has such a bad connotation on quitting that it almost seems shameful.

    As we grow and mature, it is important to be able to quit and to change our perspective on what quitting is. Quitting does not make you unsuccessful, nor does it make you a loser. It is actually quite the opposite. It takes a strong minded person to be able to walk away from something, to be able to quit their job, quit their responsibilities, and so on. Being able to determine when enough is enough and when quitting is beneficial towards our own success. Sometimes, it is okay to be selfish and to care about your own being and your own success over others. We just have to understand that quitting is an option and always will be but we have to make sure that it is the right decision. If we are able to do this, our success is unlimited, making decisions will become easier especially for those who are indecisive and will build character, allowing us to become the best version of ourselves.

    As the generation is changing and society is becoming more open minded, hopefully Gen Z’s and the many generations that are to come can help change the stigma that is held against quitting. Quitting is scary and always has been for me, but I have slowly learned that sometimes it is better to quit and it is better to redirect your life in a totally different direction.

  2. What an insightful discussion, Annie! We, as humans, have the inherent bias of how quitting is showing weakness, perpetuating the idea that persistence at all costs is the only path to success. Contrary to popular belief, quitting isn’t failure, but rather an act of knowing yourself and your limitations. Annie touches upon the idea that the act of quitting is not about giving up; I think she’s saying it’s about finding the courage to pursue what is truly worthwhile.

    I find it that quitting on time often feels like quitting too early because our society emphasizes the virtues of persistence, perseverance, and pushing through challenges. There is an ingrained belief that success is achieved only by those who never give up, regardless of the difficulties they face. As a result, we may internalize, the notion that quitting is synonymous with weakness or failure. On one hand, the inherent fear of quitting can be traced back to our natural aversion to uncertainty and the unknown. It is a primal instinct to seek stability and security, This fear is deeply rooted in our human nature and can manifest as hesitation, doubt, or anxiety when considering the act of quitting. On the other hand, the fear of quitting is also culturally influenced and ingrained within societal norms and expectations. Many societies emphasize the value of perseverance, commitment, and never giving up. This cultural narrative often labels quitting as a sign of weakness or failure, which can create a fear of judgment, shame, or guilt associated with the decision to quit. This external pressure can make it challenging to overcome the fear and make the choice that aligns with our own well-being and happiness.
    This painted narrative can make us feel guilty or uncertain when we consider quitting, even if deep down we recognize that it is the right decision. We fear being judged by others or ourselves for not enduring longer, and we worry about missing out on potential opportunities and success. The worst feeling is regretーwhen you miss out on something big that could have been yours had you kept going a little longer. It gets you thinking, “Why didn’t I just hold on?” or “Why was I so quick to quit?”. Asking yourself why over and over again and what you could’ve done differently. However, it is essential to remember that quitting something no longer worth pursuing will “get you where you want to go faster” as said by Annie. Quitting is, or ideally should be, a reflection of self-awareness to pursue paths that align with our true passions and values. Recognizing the distinction between quitting too early and quitting on time allows us to make choices that support our growth and happiness rather than simply conforming to societal expectations.

    During the discussion, Annie builds on the idea that by not quitting, “you are missing out on something that will create more progress toward your goals”. This principle is especially true for those working in jobs that make them miserable. As shown in a global poll conducted by Gallup has uncovered that out of the world’s one billion full-time workers, an astounding 85% of people are unhappy in their jobs. By quitting, you create space for new opportunities that align with your passions and aspirations. Leaving a job you don’t enjoy allows you to explore different paths, discover your true talents, and pursue a career that brings you genuine joy. People don’t always know what they want, they cant differentiate which passions or aspirations are the lasting ones. Part of the reason why is that passion doesn’t have a concrete form. Passion is an internal state of being, an intense drive and motivation that often cannot be easily quantified or measured. It is a deeply felt emotion and energy that fuels action and purpose, but its intangible nature makes it challenging to define in concrete terms. Which is partially why it’s so scary to bet on. But by making the decision to quit misguided paths or behaviors, individuals open themselves up to the realization that they don’t truly know what they want. And by facing this aspect of their nature head-on, they learn how to eventually shape and solidify their true passions. Life is too short to settle for mediocrity, and by quitting something that you don’t enjoy, you open yourself up to a world of possibilities and the potential to get what you want. Of course, this is easier said than done as quitting involves careful consideration and a leap of faith. The unknown can be terrifying but also essential.

    As someone who has been dancing for over half of their life, I relate to the struggle of figuring out when to quit, especially if it’s with something you’ve invested so much time and effort into. I remember the countless hours spent in dance studios, pushing myself beyond my limits, and striving for perfection. It was a rollercoaster of emotions, from the thrill of nailing a routine to the crushing disappointment of not living up to my own expectations. For years, I convinced myself that quitting wasn’t an option. I felt trapped by my own dedication. But I knew, I never really liked dancing, it was mostly out of obligation and fear of disappointing my family who invested their time and money into my dancing.

    Time is a precious and finite resource. Spending a significant portion of your life doing something that brings you misery is a disservice to yourself. Thank you, Annie, for detaching some of the negative stigma that comes with quitting.

  3. I fully think no one should ever quit. Although if you are someone who can’t stick to something then it’s your choice to quit or not. Even if quitting doesn’t make you unsuccessful that loses a chance of being successful. Yes you may be able to quit something that isn’t beneficial to you but every time you quit you’re losing a possibility since it could be come beneficial. The only instance where you should “quit” is when you move onto a bigger opportunity that has more possibilities. The decision of whether or not to quit something is highly dependent on the specific situation, circumstances, and individual factors. I would agree with quitting in specific instances but if you continuously quit you start to build a bad habit. I believe if you quit your not fit. Quiting opens new opportunities for other people as well if you choose to quit then someone who fits the job will take it.

  4. Oftentimes quitting on time feels like we are quitting too early because there is this negative connotation around quitting that forces people to think twice about whether they really want to quit or not. For example, I debated on wanting to quit my taekwondo classes, however, it took me a long time before I made my final decision. All because when I wanted to quit, I kept telling myself that it was too early and that I haven’t even experienced the class and its tournaments and events as a whole. However, I have been in this course for a year now and my current situation and feelings towards the class was just not worth it. So after debating about it for a couple months, I finally came to the decision to quit the class. However, even then, when I quit the class it was only because the situation was convenient and that it made it easier for me to quit with less guilt on me. Looking back on it now, I should have just quit when I thought about quitting because I spent too much time and effort on the class and debating whether or not to quit was kind of too much. However, I don’t regret quitting as I feel there are other things I am more interested in and would rather spend my money on those classes instead rather than my taekwondo classes.

    Knowing when to quit or to grit is an essential skill we should learn in our lives. Sometimes it doesn’t only apply to classes or projects, but people too. We often grit through unnecessary experiences with people in hopes that we can somehow change them or that they will somehow change themselves. However, sometimes we just got to know when to quit or cut these people out. Yes, there are some cases where these people do change. However, it is because a lot of effort and time was put into them, sacrificing precious time that could be spent elsewhere. It is often better to cut early and spend less time recovering from the lost person than sticking it out and end up wasting a lot of time with said person and then even more time recovering from said person. It’s a hard lesson to learn but an important one to keep. So yes I fully agree with Annie Duke and I think that the knowledge she has given us today is very informational and important to know.

  5. Never is perseverance and grit more celebrated than in sports. Never quitting is what helps get you to victory. You endure, you struggle, you keep going. But do you ever hear about those athletes who persevered only to end up worse, either physically or mentally?

    “The problem with grit, when taken too far….is to stick to hard things or not hard things that aren’t worthwhile,” advises Annie Duke in this article. Figuring out when something is no longer worthwhile is an important lesson and it requires a strong sense of self. You need to know what is most important before setting and recognizing limits.

    For me, the goal of collegiate tennis was a worthwhile goal. Doing well in this endeavor gave me a sense of pride, accomplishment, and identity. However, overuse injuries started to plague me as early as 7th grade. I soon embarked on what would become a four-year journey of medical visits, tests, and physical therapy – a process full of questions and big unknowns. Doctors advised switching to a different sport as surgery was not a guaranteed fix. Only time would tell if the gamble of continuing my sport would pay off.

    Was this still a “worthwhile” goal? “A fundamental problem of making the decision to quit is that quitting on time will usually feel like quitting too early,” says Duke. This was certainly true in my case. At this point, having the “kill criteria” Duke speaks of before emotions got in the way might have been a good thing to consider but I, and even my parents, simply did not have enough experience to know what criteria to trust.

    I ended up persevering with a new coach, new technique and intensified physical therapy. My resilience and grit were celebrated. However, after two more years, I finally recognized that my shoulder was never going to return to normal and that competing at an elite level would not be possible. My “kill criteria” became very simple: when the recurring pain and disappointments started to negatively impact all the other aspects of my life, I knew I had to fold.

    One surprising lesson here is that persevering not to quit is by far the easier choice. You are lauded and applauded for such courage; our society rewards that kind of grit. But learning when and how to walk away from something requires much more courage and introspection because, in the end, you are often alone in making an unpopular decision. That is a journey that teaches some important leadership and decision-making skills very useful in life and in business. You learn a lot about yourself and what you find most important. You understand your limitations and know how to ask for help. You start to look to other interests and find other opportunities. You keep exploring and learning to be flexible over different possibilities. Learning when to fold is a problem-solving skill that turns a negative into a positive. In the end, “quitting will get you to where you want to go faster” and for me, that is now developing into the person I want to be and focusing my energies on a future career in entrepreneurship.

    “Quit” is not a bad word; it’s even the eye-catching title of Duke’s book. Knowing when to fold is not an easy decision and is a definite process that needs practice to make the next experience more efficient. I believe with each time, you will emerge stronger and more confident in any direction you have chosen.

    Thank you, Annie, for making “Quit” a respectable, strong, and wise option.-

  6. What stuck out to me in Annie Duke’s ethos was her quote that “quit and grit are two sides of the same decision.” Her idea inspired me to think about an important experience I went through as a kid, where I struggled with when and how to quit something — and, through that conflict, came to the same conclusion as she discussed in this article.

    My mom signed me up for many extracurriculars when I was younger. My weekends were jampacked with dreaded trips to my morning Chinese school followed by art lessons and a walk downtown to get to a vocal class. Afterward, she’d take me on another two-block walk that, at that point, felt more like a trek across a country on my exhausted limbs, to get to a dance lesson, topped off with a piano class. Martial arts lessons were off the agenda only because it was impossible to feasibly fit another extracurriclar in my schedule, thank goodness.

    Attending these classes with the expectation to do well in all of them really took a toll on my ten-year-old self. What should have been meaningful hours spent practicing the piano soon became monotonous and something I would detest. It wasn’t uncommon for me to come home after a long weekend and immediately collapse on my bed. I spent so long doing so many different activities that attending these classes soon became a drag, weekends quickly becoming something I dreaded. Singing and dance were activities I once had a lot of passion for, but it simply wasn’t worth it to take hours out of my already-busy weekend to attend those lessons. I soon began to question whether the amount of time I spent doing extracurriculars over the weekend was enriching or sustainable.

    Duke believes that grit means spending time doing something worthwhile, even if said thing is difficult. When I evaluated my extracurriculars, I realized something important: the majority of them weren’t things I even liked. Was it worth it to devote this much effort to something that wouldn’t be worthwhile? The answer was a resounding no. I learned that taking time out of your day for a craft should be of genuine interest and passion — otherwise, spending grit on said craft is useless. I wasn’t going to become a world-class singer or a renowned artist, so why waste my grit spending time on them at all?

    Even though I ended up quitting the majority of my extracurriculars soon after this realization, I still learned an incredible lesson from years of exhausting weekends and busy schedules. I got to experience grit. I now use this grit to channel it into extracurriculars and endeavors I’m interested in, such as creative writing and journalism. Am I a great dancer? Not at all — I can barely do a cartwheel. Do I still do vocal exercises? Definitely not. But, through my grit, I now appreciate the importance of consistent practice and thoughtful time management.

    Impactful articles are meant to not only display information, but to help the reader realize things about themselves and provide new insight. I’d never thought I could relate to an article that, at the surface, is simply a listicle that gives tips on how to quit. However, Duke’s advice that this article brings to light isn’t — and shouldn’t be categorized as — just that. I plan on continuing to read and comment on these articles from the Wharton Global Youth Program: because they will always prompt me to reflect.

  7. It was a crisp, autumn Sunday. With the crunch of leaves snapping below our feet and the soft gust of wind twirling our hair, my brother and I approached the holy destination: Target. In commemoration and well, convenience my parents combined our birthdays and granted us an exorbitant budget of thirty dollars. Without the need for words, my brother and I had reached the proposition to purchase as many booster packs of Pokemon Cards as we could. We yearned for our investment to yield us rare “Ex”es that looked “ebic” or even the rumored “Mega-Ex”es and “Secret rares,” which were elusive cards of much higher value. We weren’t only hoping for cards that would befit our fancy, but also, the fancy of fellow traders who would get scammed- er TRADE their cards in a net gain for us. In fact we have already amassed a net gain of ten dollars in our transactions. Our grit, it seemed, was boundless.

    Now, the trade of Pokemon cards was equivalent to the black market for elementary schoolers. The risk of confiscation by teachers and a slew of unjust punishments was a persistent threat. In my school, the staff was on a tyrannical crusade against Pokemon cards that overshadowed even that of their campaign against gum. So of course it would be of common occurrence to witness exchanges being committed in the moshpit of the cafeteria, the secluded recesses of the auditorium, during class, and the bathroom stall- which sometimes curiously exposed two pairs of legs. It was truly a grisly time to behold, with no guarantee that a potential trader would commit to a deal or be discovered. But now, before the holy shelves of overpriced cards ($5 a pack!) we were blinded by our dreams. Our star-struck eyes could see nothing but the pedestals before us.

    As soon as we were home, the cards were attacked by the ferocity of two almost feral boys. Plastic wrapping flew like confetti until at last the cards were all put into one pile. And thus, the reveal: we flipped through stacks of common cards, some hollows, a couple of reverse hollows, and… more trash that wouldn’t even amount to a penny. The only Ex that we got was a Togekiss which looked like a face on an inflated pillow whose corners were stretched to resemble wings. We were devastated. We could no longer train the monkeys- not a soul would trade for it. To make matters worse, the following week a five dollar card was confiscated by a random teacher that never returned it. We had dug our heels in and invested twenty dollars and a year… for naught. With the internet we confirmed that our cards were worthless and the Togekiss, two measly dollars.

    In brief, I completely agree with Duke’s five virtues of quitting. Having first hand experienced this brutal loss of money at the innocent age of eight, I can attest to the first three virtues. In retrospect, I was able to find the percent chances of obtaining rare cards and the odds of getting a Ex was 17%, a Secret Rare at 2% and a Mega… impossible as it can not be found in booster packs. I’m no expert at math but these chances are definitely in my kill criteria, especially with only twenty dollars. In fact, eight year old me was traumatized enough to put this experience on his kill criteria and be smart enough to progress to virtue five, seeking alternatives. And that is how we ended up with Yu-Gi-Oh cards worth as much as the very paper they were made of the following year.

    Armed with my veteran knowledge on the philosophy of quitting, I’ll be sure to utilize the five virtues. I would be able to separate emotions from logistics, recognize the necessity to guarantee the training of a whole circus of monkeys, create intelligent alternatives and – is that an overpriced non-fungible token of a stoned monkey?

  8. Way before I could even make my own rational decisions, my mom shoved me into the world of ballet, and for a while I enjoyed it. I wasn’t prima ballerina level but I didn’t look like a wobbling toddler doing it either. It was actually pretty fun to be one of those people backstage with the stage fright jitters, with the occasional accident of kicking someone in the eye in our ocean of teal tulle, even if I thought it was the worst feeling ever back then. Slowly but surely, it got less enjoyable, I was probably the worst in my class level and I lacked motivation, thus leading to a lack of skill, compared to the people who practiced and refined constantly. My heart said, “I hate this! I wanna quit!” but my brain said otherwise. I had devoted 6 years of my Saturdays doing this, 6 years of my mom hauling me round trip, 6 years of tuition, and 6 years of my own energy and effort. There were a lot of points to cover in quitting, I couldn’t just quit then and there. Ten-year-old me had to gather the guts that were sprawled all over the floor, which took the course of a month, to finally tell my mom, no thanks, ballet is not for me. At first, my mom rejected me immediately. So I squashed the idea back down and kept going for another 2 sorrowful years. Then my “quitting idea” resurfaced again, worming its way back into my brain. At this time, my mom was more open to it and, reluctantly, gave me the green light. I felt free and ecstatic but at the same time, a little regretful.

    “Quitting on time will usually feel like quitting too early.” Reading through this article, this particular statement caught my eye. I could say that I relate to it, but only to a certain extent. To me, it’s more of the opposite, what if I’ve waited too long to quit? What if I’m already stuck in this ocean of tar that is holding me back because I feel that I’ve already spent so much time, energy, and money? What if it’s too late to go back? I don’t think there really is a time span for quitting, anytime could be the right time, if you make it the right time. I wasn’t one of those kids that juggled extracurriculars that took up every minute of their free time nor a kid that just hung out, I was more like a love child between the two. In quarantine, I filled my time with a load of online activities, like the Debate Team, only to quit in a week because it was dreadful.

    I quit quite recently, but I’ve already made progress in these 1 ½ years. I’ve already started to pick up some other hobbies I enjoyed, while ballet was slowly crumbling. I fumbled around with these activities, not quite sure if it was going to head in the same path as ballet. I started to take swimming classes, picked up volleyball, and spent more time on art. To this day, I do enjoy all of these activities (although, art block can throw itself off a cliff), so I’m glad I decided to pick them up. However, happy endings are not always completely happy for everyone, there’s the villain. I still “battle” the “villain” of quitting other things in my life, like other hobbies and even friendships. There’s always more to learn since there is no perfect formula for quitting. All in all, I am satisfied with my decision to quit at 8 years, instead of spending even more time and money, so for me, 8 years was the perfect time to quit ballet and 1 week was the perfect time to quit the Debate Team.

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