When should you quit?

Serial entrepreneur Michael Girdley walks through four frameworks for deciding when to quit: Annie Duke's pre-set thresholds, Reid Hoffman's single-goal test, Jeff Bezos's 75-year-old self advice, and Derek Sivers's "hell yes or no" rule. He adds a 2x2 matrix plotting joy against profit, and argues that if you're asking whether to quit, you probably should.
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So when should you quit something? It's one of the hardest things to do, uh, because there's a lot of things going on in our brain that make it very difficult for us to quit something that we've been working on for a long time and we're maybe like very emotionally invested in it. So how do you know when you should quit that thing? Well, that's what this talk is about. I'm going to give you a framework to talk about it and think about it and then be able to make a good decision to quit maybe something that you're considering getting out of. We'll do it all in less than 10 minutes. So if you're new here, my name's Michael. I'm a multiple business owner. I like to share stuff on the internet because I like to teach. I also like to talk about business because I'm a business nerd. So those two things work super well all together. If you want to get better at running a business, if you want to get better at that sort of stuff, uh, give me a follow, give me a comment below. It will help me be seen more, and I'd appreciate it. So who is this for? You are someone that is working on multiple projects. Maybe you own multiple businesses like I do, or maybe you have a job or relationships in your world that you want to get out of. Maybe you're volunteering for some organizations, or some combination of all of those things put together. This presentation's for you. You are thinking about quitting something, but you're not quite sure if you should. So anywhere you're spending your time, it's maybe something you want to get out of. We're gonna talk about how to know when to quit at least one of those things in this Look, let's start with why quitting is so hard. That's one of the things we need to have in our mindset as we think about getting out of things. And there's a bunch of things that are wired in our brain that makes it very difficult for us to quit things. And some of those are things called cognitive biases or cognitive fallacies. And these are ways that our brain, like, tricks us on stuff. And one of those tricks is this thing called the sunk cost fallacy, which is you take a look at something that you've worked on for a long time and you're like, oh, I have all this time and money invested in it, like, I should continue working. It'd be a shame to waste that money, or it'd be a shame to waste all that time and it'd be for nothing. Well, the reality is That's a trick. The trick is that money, that time, it's already spent. It's not going to help you anymore to keep working on it, whether— no matter what the outcome is, it's not like you're able to ever get that back. So that's one of the first ways and reasons it's hard to quit. The second is this idea of opportunity cost, which is our brains aren't really well wired to understand the opportunities we're missing out on by working on something. So let's say you have a job. Well, that means you can't go work on something else because there's an opportunity that you're— well, you, you can only work on one thing at a time. You can't work on that other opportunity when you have a full-time job at one particular company that maybe you want to quit. The last thing is It's super hard to quit, often because of emotional and societal pressures. And I'll talk a bit later in the presentation. I've stuck with stuff for a long time because I felt emotionally obligated to other people to keep working on those. There's also things where you have a level of kind of societal pressure. If somebody thinks that, you know, your business that is a success and you quit it, well, maybe it wasn't a success and you don't look as good in the eyes of your friends. So there's societal pressures as well that make it difficult for us to quit things. Why is it so important? It's so important because focus is power. If you're working on things that are distracting you from what you're really meant to be doing, and you be quitting, like, that hurts your ability to execute well on those things. And in the end, like, you only get one life to live, so how are you going to spend it? Well, you don't want to spend it working on things that you should be— well, should have quit. And frankly, like, one of the reasons I've often quit stuff is there's only so much you can do at any given time. Uh, I call this shower time. Like, I can only focus on so many things at a given time, so sometimes I just need to quit stuff so I can make sure I do my best at the things that are the most important for me. So let's talk about a couple of frameworks that you can use to think about when to quit. And this is a cool one that a lot of people, as I've talked about this issue, have mentioned. It's from Annie Duke, and it's called the Quit criteria framework, and it's basically this: before you start a project, you define what success will look like. We all kind of do that, like, oh, this business will make us a lot of money, or we'll go public someday, or this venture will change a lot of people's lives. But what we don't do is sit down and imagine what could happen on the downside and what would cause us to quit. So for example, like, let's say, uh, you're going to start a new business. When you would start that new business, you would go in and say, okay, here is what would cause me to quit that business, right? For example, if we can't get any investors to sign up, well, then I'm going to quit that business because I, you know, can't continue no matter what. Or you might say, hey, if no customers show up and are willing to pay us within 3 months, we're going to quit, right? And so we basically define the opposite of these success criteria to be failure criteria. And what Annie espouses in this kind of approach to quitting is you premeditate quitting and you say, okay, well, before I get into something, before I work on something, I'm going to decide that I'm going to get out. And another example, let's say you get into a job that you hate, or you go into a job and you're worried you might hate it. Well, one of the things that will cause you to quit is your boss— you don't get along with them. Well, if that happens, then you should definitely quit. So these, these would be these ideas that Annie Duke would use us to take a look at things and decide what to quit. All right, here's another framework to think about when to quit. This comes from Reid Hoffman. He founded LinkedIn, and basically a lot of what these guys that worked with LinkedIn and other folks around a startup called PayPal had was this idea of maniacal focus, or like you just singularly work on one thing. And what Reid would force people to do when he was running his business, uh, and tell people how to make decisions was write down the number one thing that you're trying to accomplish. What's your number one goal? And then ask yourself, is doing this thing that I'm considering quitting helping or hurting that particular goal? And if the answer to that is it's not helping me achieve that goal, that mission that I'm on right now, then I should quit doing that thing. So for example, let's say you're a co-host of a podcast and your number one goal is to build a company that goes public, uh, and you ask yourself, should I quit doing the podcast? Well, unless that podcast is helping you to create that business and your number one goal that you're trying to achieve, you should quit it. And that's the Reid Hoffman framework here, this number one goal framework. And in my case, like, I wanted to be in low capital expense businesses. These are businesses that didn't take a lot of capital to grow and that sort of thing. And I wanted to own high— I owned high capex business that was requiring a lot of capital. It's this business I'm wearing the t-shirt for. It's a coffee company. And that made an easy decision. It was in the way of my number one goal of how I wanted to transform the things I was working on. And it was easy. I put it up for sale and we sold the business. In other words, I quit it. Okay, here's a number three way to think about quitting, uh, and this is the regret minimization framework. So this comes from Jeff Bezos, founder of Amazon. And basically what he says to do in this is imagine yourself at age 75, you're on your deathbed. What would this version of you, the person of you that's dying, uh, say you should do at this particular moment? And if this person were to say that you should quit your job or that relationship relationship or that business that you're involved in or that side hustle that you're doing, you should quit. And as an example, like, I know people that dreamt of being an entrepreneur, but quitting a W-2 was risky, both from a societal standpoint and a money standpoint and all this kind of stuff. And 75-year-old me would tell me that I should quit it and pursue my dreams and, you know, swing for the fences. And 75-year-old me would also be okay even if I did that and I failed. 75-year-old me would not be okay if I didn't try. So regret minimization framework here around quitting. All right, number 4, this comes from Derek Sivers. You may know him, he does a lot of tech talks and stuff like that. It's a hell yes or no framework. Basically, the idea is you divide everything into two categories and two categories only. It's either a hell yes or it's a no. And hell yeses are things that you have unwavering enthusiasm for. Like, you have commitment to something and a feeling that you absolutely must do that thing. You couldn't imagine life without it. Everything else is a no, and you should say no to that stuff and you should quit it. And for example, I worked on a business that I hated. Made— and this happened in my life— I made good money, but it was miserable. And so it was not a hell yes, which made it a no. And eventually I got out of that business over time. I sold it and found other stuff that was a hell yes for me, that I found inspiring for all of me and all of my soul and mind and that kind of stuff. So Hell Yes or No framework is a framework for me. It's based on the insight that society and money and all this stuff, it clouds our judgment. And when I talk to people about why they're not quitting things, it's often because of irrational things like, what will my neighbors think of me? Or will I let people down? Or will I feel like I'm a failure? And so I ask yourself— this is the question I ask— would I work on this particular thing for free, or if it cost me money? Like, even if I got nothing out of it, let's say I have a ton of money in the business, or let's say I have a ton of time in it, or a lot of my prestige comes from it, and— but I, I'm concerned and I'm ready to quit it, I'm thinking about it. Like, if you ask yourself, would you work without any of those things in the way— money, obligations, prestige. Like, would I do this for free without notoriety, without any of that kind of stuff? And if you wouldn't do it without those things, it's time to quit. And so, example for me, I was on the board of a prestigious organization, but I was miserable with what we were doing. It was very different, and the organization had transformed over a number of years, and I felt an obligation because I helped start it, I helped get it going. But once I felt like I had done enough, kind of fulfilling my commitment to the people that had been there at the beginning, I decided to quit the board. I moved on, and it was a great decision. But, you know, I had to put aside all of these things that were holding me back from making the decision. I was scared about what other people would think or that I would let them down or that would cost me money. Well, in the end, like, it was the right decision to get out of it. Okay, so let's put all this to action in the last couple slides. There is a framework that I use if you're working on multiple projects to go through and sort your priorities, and it's uses a 2x2 matrix. You've seen these if you've been in business for a while. It comes from Boston Consulting Group, typically called BCG. And what I do is I put together a 2x2 matrix of all the stuff I'm working on, and one axis has the amount of joy I get out of it, and the other one is how much profit or benefit I get from the thing. And I put every major project that I'm working on there. It helps me sort and see where things sit relative to other things. And then basically the algorithm is the following. You should start killing stuff in the bottom left corner of things that aren't making you much money and aren't giving you a ton of joy. So actually, I had ChatGPT build this for me for a hypothetical entrepreneur. And you can see here, basically, the hypothetical entrepreneur put in different types of stuff the hypothetical entrepreneur was working on. ChatGPT didn't put anything here in the bottom left corner. But if there was stuff in the bottom left corner, these would be the things that you would start killing first, start quitting first, so you can focus on this stuff that gives you joy and gives you profit here in the top right corner. All right. Closing thoughts on all this. Quitting takes courage. It's hard. But I have never in my life or in— heard anybody ever say that they regretted quitting on a bad employee, a bad relationship, a miserable business, or any of that stuff too soon. And personally, I've never regretted quitting something. The regrets I have had are when I didn't quit soon enough. That's the only regret I've had about quitting. And then the last kind of thought around this is, if you're asking, should I quit this employee, or should I quit this particular venture, or should I quit what I'm working on, or should I quit this thing that, you know, is at that bottom left-hand corner of the matrix that I just showed you— if you find yourself asking that question, or somebody asked me that question, should I quit, the answer is always yes. Because by the time you ask the question, you're— it shows to me that in your brain you're stuck on all the things that don't matter, like societal pressures and money and risk and all that kind of stuff, when in reality, like, the core of who you are is starting to show through, and that is showing in you asking this question of should you quit. So my advice is, if you were debating quitting something and you opened up this video to get somebody to tell you, like, hey, here's how to figure out if you should quit or not, just you asking the question is enough for me to tell you you should just quit and you should just do it. All right, so that's what I know about quitting. Thanks for being here. Let me know what you think in the comments below. Bye.










