I Quit — And You Should Too (Sometimes)

Quit by Annie Duke

This blog is inspired by a book I read recently, one that resonated with me so deeply, I knew a single Toastmasters speech wouldn’t do it justice. So here I am, dedicating an entire post to it. The book offers a bold and unconventional take on perseverance, challenging the idea that we must always push through at all costs. Sometimes, the most courageous and strategic thing we can say is "I quit". Not out of weakness, but to make space for the opportunities and questions that truly deserve our energy and focus.

"How many of you think that the word 'QUIT' has a negative connotation?

Now, what if I said, 'John quit smoking'? I mean, that’s fantastic, right? John has just done something incredible for his health—he’s probably added years to his life. But what if I said, 'John quit his college, his job, or even his relationship?' We wouldn’t hesitate to call him a serial quitter or someone who just can’t make things work. The question for us today is: Why is quitting viewed in such a bad light? And what if I told you that quitting is a skill—a skill we can all learn? This speech will shed light on how we can get better at quitting, with real-life stories and lessons that can help us let go of things that aren’t working, so we can move on to better things. In fact, most of us grew up hear sayings from the legend Vince Lombardi like ‘Quitters never win, and winners never quit.’ But what if the opposite were true? What if quitting, at the right time, could actually help us win in the long run? What if quitting could be the smartest decision, not a sign of weakness or failure?"

"Now, I’m not talking about quitting when things get tough, or when we hit a minor obstacle. I’m talking about quitting strategically—about recognising when it’s time to walk away from something that’s no longer serving us, to make room for something better. This concept of strategic quitting is something that Annie Duke talks about in her book Quit. But before we dive deeper into how we can become better at making these strategic decisions to quit, let's first take a step back and try to understand why quitting is so difficult for us in the first place. And along the way, let’s see how we can tackle each of these challenges one at a time.

1)    Sunk Cost Fallacy:

“But we’ve already invested a million dollars and 200 man-hours into this! We can’t just let it go now!”

How many of us have heard, or even said, something like that? This is the sunk cost fallacy at play—where we feel compelled to continue because of what we’ve already invested, even when it’s clear that the situation isn’t working. The problem is, by persisting, we often waste even more resources, digging ourselves deeper into a hole, only to realise we should’ve quit much sooner.

A popular British saying goes, “Don’t throw good money after bad.” Yet, in the early 2000s, the UK government fell into this very trap with their national ID card project. Despite realising halfway through that it was a lost cause, they continued pouring money into it for another decade. Why? Because they had already invested so much in the analysis, technology, and infrastructure. If even governments can fall for this trap, how can we, as individuals, avoid it? The answer is simpler than you might think. Next time you hesitate to quit, ask yourself: Am I holding on just because of what I’ve already invested, or is this still the best course of action?

If that doesn’t help, consider this strategy to avoid sinking costs in the first place. Imagine you want to train monkeys to juggle on a pedestal. What do you do first? Train the monkeys, right? Without them learning to juggle, the pedestal is useless. Yet, in our projects, we often begin with the easy tasks—building the pedestal—because we crave progress. But if the monkeys can’t juggle, the pedestal is wasted effort. So, ask yourself: Am I building a pedestal for a monkey that can’t even juggle? This mindset helps us avoid wasting resources on something that’s unlikely to work.

2)    Goal Fixation:

Another reason we struggle with quitting is due to goal fixation. It’s natural to start something with a clear end result in mind—after all, it’s hard to commit to anything without expecting something in return. But the problem arises when we chase that goal so blindly that we lose sight of whether it’s still the right goal. We become fixated on the finish line, even when the path we’re on no longer serves us. That tunnel vision makes it incredibly difficult to pivot or quit, even when every sign says we should.

Imagine you’re climbing Mount Everest. You’ve spent years preparing—saving money, training your body, maybe even sacrificing relationships. After weeks of trekking through brutal weather and low oxygen, you’re just a few hundred feet from the summit. You can literally see the top. But then your guide checks the clock and says, “We’ve hit our turnaround time. We need to head back now—or we might not make it down safely.” In 1996, several climbers were in this exact situation. Despite the warning signs—exhaustion, bad weather, oxygen running low—they pushed on. They were so emotionally and mentally invested in reaching the summit, that turning back felt like failure. They did make it to the top. But tragically, some never made it back down. Now, we only see this as a devastating story because they didn’t survive. Had they returned safely, we might’ve praised their grit and perseverance—even though they ignored clear signs.

That’s the danger of goal fixation. So how do we avoid this trap? It’s simple: turnaround time is our answer. And in the real world, that means having a kill criteria and setting it up early. A kill criteria is something we rarely set. We define success in glowing terms but forget there’s an equal probability of falling short. And when things do go south, we don’t know when or how to quit—because we never defined what failure looks like.

A good kill criterion might sound like: “If I haven’t hit X milestone by Y date, I’ll walk away.”

It removes emotion from the decision and makes quitting feel strategic, not like giving up. And that’s exactly what turnaround time is for climbers on Everest. It’s not quitting. It’s surviving. It’s winning the long game.

3)    Combining Identity and Goals

Finally, We tend to tie our identity too closely to our goals. Think about it—how many times have you heard someone say, “I’m a founder,” “I’m a marathoner,” “I’m a PhD student,” or even “I’m a climber”? These aren’t just things they do—they become who they are. And that’s where it gets dangerous. Because if you’ve told the world and yourself that, quitting starts to feel like an identity crisis. It’s no longer just walking away from a job, a project, or a goal— it feels like walking away from yourself. We stop asking, "Is this still good for me?" and instead we cling to, "But this is who I am."

Let me give you a relevant example from sports: Did you know that Michael Jordan was not just a basketball player, he was also a professional baseball player? After winning three consecutive NBA titles with the Chicago Bulls, Jordan shocked the world by announcing his retirement at just 30 years old at the peak of his powers.

He pursued baseball for a short time representing the White Sox in MLB, even hitting home runs but when he returned to basketball, he was a better player, a better person, and, crucially, he wasn’t tied to being just a “basketball player.”. He showed the world that quitting was not a sign of weakness—it was a sign of personal growth and awareness.

Don’t let your identity be trapped by your goals. You are not your job. You are not your title. You are not even your goals. You’re allowed to change your mind. You’re allowed to walk away. And doing so doesn’t mean you’ve failed— it means you’ve grown.

I hope the small tricks shared here today will help you face the fears of quitting. But above all, always surround yourself with truth-tellers—the ones who can show you the mirror, keeping you grounded so you don’t get bogged down by sunk costs, the harms of tunnel vision, or the crisis of identity when it’s time to quit.

Most importantly, don’t wait for certainty before making the decision to quit. As I like to say, Quit when everyone asks you, "Why?" and not "Why not?"

So, here’s to happy, strategic quitting—moving from things that hold you back to those that propel you forward.

And with that, I Quit!

P.S. In case you’re wondering: the Toastmasters speech was a hit, and I was thrilled to walk away with the Speaker of the Day award.

Toastmasters Best Speaker Award for Quit!