Quit the wrong stuff. Stick with the right stuff. Have the guts to do one or the other. — Seth Godin, The Dip
I picked up this book some years ago. Until that point, I had done a fair amount of quitting. I had quit jobs, projects, relationships, and self-founded ventures. With hindsight, some of these decisions were good, some regrettable. I never had a general framework for thinking about whether to stick or quit something. Templating off the book, I've developed my own method for approaching such decisions. It's not a magic wand I wave at those ambiguous junctures in life, to conjure the right choice. It's just a structured way to get out of my head, and navigate those moments with clarity. I've been surprised by how generalizable my framework has been, but it's bent towards decisions faced in ambitious endeavors. Here's what this guide currently looks like.
questionnaire
I know, a long preamble for what's essentially a list of questions:
- Are you panicking?
- What exactly are you thinking of quitting?
- Are you willing to be the best in the world?
- Is your persistence going to pay off?
- Are you making measurable progress?
- How can you fail fast?
- If you quit now, will it increase your ability to get through the Dip on something more important?
- Is your desire to stick motivated by sunk cost?
- Are you letting pride get in the way?
- Would you regret the journey if you quit now?
- If it scares you, it might be a good thing to try.
When I'm agonizing over a decision, I run through these questions, not necessarily in one sitting. But, I do try my best to approach them honestly, from the gut. If you're an overthinker like me, rationalizing every side of an argument comes naturally. It helps to reactively answer each question, before the brain has a chance to intervene.
Why these questions? Here's some brief context for each of them:
0. Are you panicking?
This is obvious, but you shouldn't make any big decisions when you're panicking (or experiencing any emotion intensely). Your judgement is compromised, co-ercing you into thinking short-term. Thinking reactively. This can be dangerous and expensive for the long-term. If you feel like you're heart is about to burst out of your chest, it's best to wait until the panic subsides before continuing.
1. What exactly are you thinking of quitting?
Sometimes, this is clear. Other times, it helps to be explicit about this. If you're business is struggling, are you thinking of quitting a marketing channel that's not converting? Or a product that's not working? Or the market? Or the strategy? Or the whole business altogether? If you're in a job you despise, are you contemplating quitting the team? The company? The industry? Or your career path altogether? Knowing this grounds your thinking for the rest of the questions.
2. Are you willing to be the best in the world?
"if you don't try to be the best, you won't even be good" — Paul Graham, How To Do Great Work
In just about every market—from consumer goods, enterprise software, labour, to even dating—there's an over-abundance of choices. Faced with a dizzying array of choices, many people just pick the market leader. They buy the highest-rated product on Amazon, they eat at the most popular restaurants on Yelp, and choose the accounting software that's recommended by the most people they trust. So markets are tending towards winner-take-most. The best product, service, content, employee, business, dating profile, etc gets 10x the rewards of the second-best, and the second-best gets 10x the rewards of the third-best, and so on. (Zipf's law is a bitch.)
That means that if you're going to achieve anything ambitious, you have to be willing to be the best in the world at what you do. But "world" is a flexible term. If someone's looking for a freelance videographer, their world is the set of all freelance videographers who speak their language, who are available, can work in their region, for a price that fits their budget. So you can scope "world" however you like, but you have to have the capability and williness to be the best in that category, otherwise the juice is likely not worth the squeeze.
3. Is your persistence going to pay off?
Seth Godin explains that almost everything worth doing in life predictably imposes a period of hardship, which stands between starting something and achieving success. This is the Dip. The book goes into much more detail on different types of dips—education dips, risk dips, emotional dips. The idea is straightforward though: you need to suffer through a dip, otherwise the payoff on the other side would not be worth it.
But not every dip leads to a payoff. Sometimes, when you're experiencing struggle, you might not be in the heart of a dip, but you could be in a cul-de-sac—a dead end, where nothing changes despite constant effort. Unfortunately, dips and cul-de-sacs aren't linear, so they don't feed you little bits of information to help you distinguish between the two.
Persistent people can visualize the light at the end of the tunnel when others can't see it. At the same time, smart people are realistic about not imagining light when there isn't any. So, do you believe there's light at the end of the tunnel? I'm sorry, but I don't have advice for how to approach this question.
4. Are you making measurable progress?
Even though I just said progress may seem elusive, if you can sense it—or even better measure it—than it's a good reason to stick. However, if progress has been incremental over a long time, and you're not sure if it's going to accelerate, it may be a sign to quit.
5. How can you fail fast?
When you're in the the throws of uncertainty, maybe the best move is to get more information in the direction of making a decisive choice.
Personally, I've found this works great for well-defined tasks, like A/B testing a marketing channel, or trying out a new feature in a product. But it's so hard to apply it to bigger decisions like business strategy or startup vision, because it's hard to identify what failure or success concretely looks like until you're deep into it.
6. If you quit now, will it increase your ability to get through the Dip on something more important?
It's ok to quit, and to do it often, as long as you're quitting the paths that don't go anywhere or aren't important. And if you truly believe that quitting will free up your resources to get through the Dip on something that's truly more important, then you should do it.
But beware of becoming a serial quitter, like me. For a long time, I was the wannabe-entrepreneur who jumped from idea to idea, as soon as he hit his first obstacle. I thought I was "pivoting", in search of something better, but really, something easier. I would give up long before paying my dues in the Dip to reach some pay off. Unfortunately, when you start over, you get very little credit for how long you stood in line with your last venture.
7. Is your desire to stick motivated by sunk cost?
By the same token, beware of the power of sunk cost. Just because you've invested a lot of time, money, or effort into something doesn't mean you should keep going. Today is day 1 of the rest of your life, so given what you know and possess, make the choice that's going to maximize your future.
8. Are you letting pride get in the way?
Pride is the ugly cousin of sunk cost. Sometimes, we stick with something because we we're too afraid to admit to ourselves or others that we were wrong. But quitting in those situations is just like ripping off the band-aid. People usually feel really good after they quit a dead-end project because they discover that hurting one's pride is not fatal. You work up the courage to quit, brace yourself for the sound of your ego being ripped to shreds—and then everything is okay.
9. Would you regret the journey if you quit now?
Although we have a hard time acknowledging it, so much of what occurs in life is governed by chance. So despite our best efforts and wishes, sometimes, we don't achieve the outcome we want because of poor luck. Having the respect and appreciation for the chaos of the world, before sticking or quitting, I now ask myself whether I would regret the journey—not whether I would regret making it to the destination. A journey can be meaningful through learning, growth, challenge, passion, relationships, etc., all totally independent of success or failure. So if the instrinsic rewards of the journey are valuable to me, it's probably a good idea to continue.
10. If it scares you, it might be a good thing to try.
"If you have two choices to make, and they're relatively equal choices, take the path that's more difficult and more painful in the short term." — Naval's Razor
Not a question, but a reminder. When something scares you, in the right kind of way, it's a sign that you're about to step outside your comfort zone for something meaningful. Fear can be a valuable signal.
bonus: If you're going to quit anyway, is there something dramatic you can do instead that might change the game?
Taken from Seth Godin himself:
"When the pain gets so bad that you're ready to quit, you've set yourself up as someone with nothing to lose. And someone with nothing to lose has quite a bit of power. You can go for broke. Challenge authority. Attempt unattempted alternatives. Lean into a problem; lean so far that you might just lean right through it.
David found himself stuck in a dead-end job at the end of a long career at one company, and he was ready to quit. His boss was a disaster, the work wasn't adding any value to his resume or his day, and he was unhappy. David went for broke. He had a meeting with his boss and his boss's boss (quite a no-no) and calmly explained his problem. He said that he figured he'd end up quitting, but he liked the company so much he wanted to propose an alternative. So he did. He walked out with a major promotion, a brand-new challenge, and a new boss. If he had covered his downside, worried about the short term, and not been prepared to quit that very day, it never would have happened. He wasn't bluffing. He really was ready either to quit or to lean into this new job, to rededicate himself to the company and make something happen."
conclusion
Work culture, at least in the west, has had a strong obsession with "not giving up". But, I'm glad it's coming around to the idea that quitting is not only okay, but smart, in many areas of life. I mean, ffs, The whole "fail fast" ethos in startups is about quitting the bad ideas quickly, so you can invest resources in the right ones. Sounds cheesy, but I think strategic quitting is the secret to success. But reactive quitting and serial quitting are the enemies, and most people (especially myself), do just that.
If you've decided to quit, congrats. Hope you can focus your energy to sticking with a better path.
If you've decided not to quit, then you now need to do the opposite of quitting: rededication. It's investing in an invigorated new strategy designed to attack the obstacles facing you in a new way. Good luck.