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How to know when to quit

[ 18 ] January 21, 2011 |
Should I quit? Graffiti says, "Quit your job and go paint at night"

Image by dev null, on Flickr

Do you ever wish you could see into the future and know how things will turn out, so you can stop throwing energy at things that aren’t going to amount to anything? Should I start a blog, or will it just end up on the electronic junk pile? Should I keep trying to build my yarn-dyeing business, or is it a dead-end proposition? Should I stick with my job, or quit and find a new one? And then, of course, is my career going to get better, or should I find a new one of those? Should I stay or should I go?

Most things are fun when you first start them. There’s the excitement and novelty of trying something new, the exhilaration of growth and learning a lot in a short time, and the dramatic progress of going from zero knowledge and skill to some knowledge and skill. But what happens after that?

Once the initial rush wears off, things level out. The novelty wears off, progress is less dramatic, and suddenly, it starts seeming like an effort.

At that point, I often quit. I’m kind of a serial monogamist, with guys as well as activities. There’s the initial crush phase where everything is skyrockets and bliss, and nothing else even seems interesting. Then things settle into a pretty happy, more reasonable routine. Then things get difficult (familiarity starts to breed contempt, bad habits accumulate to the point of annoyance, there’s a worldwide spike in the price of merino wool, etc.), and I quit.

I get a lot of teasing about this from some of my friends, and deservedly so. I always think I’ll love someone or something “forever,” but it always turns out to be more like 3 years. Houses, jobs, romantic relationships–each starts out appearing to be the grand answer and something I’ll love forever. Then, three years later, I’m gone. The one exception is my car, which I’ve owned for almost 13 years. (What can I say, it’s a Honda.)

Quitting: the opposing theories

We’ve all heard a million times: don’t quit. You can’t succeed if you quit.

A quitter never wins and a winner never quits.
Napoleon Hill1 Vince Lombardi3

Most people who succeed in the face of seemingly impossible conditions are people who simply don’t know how to quit.
— Robert Schuller1

Most people give up just when they’re about to achieve success. They quit on the one yard line. They give up at the last minute of the game, one foot from a winning touch down.
–Ross Perot 1

I think the Ross Perot quote sums up the worst fear about quitting: what if I quit right when I was about to succeed?

But then again, there’s the opposing view.

Quit while you’re ahead. All the best gamblers do.
–Baltasar Gracian2

Of all the stratagems, to know when to quit is the best.
–Chinese Proverb2

If at first you don’t succeed, try, try again. Then quit. There’s no use being a damn fool about it.
–W. C. Fields1

Ok, so maybe the last one is tongue in cheek, but doesn’t it spell out what we’re really afraid of if we don’t quit: what if I’m wasting time and energy by foolishly pursuing a dead end?

When to quit

I’ve seen a lot of advice lately that says that if you keep doing a little bit every day toward your goal, you will eventually get there. But let’s face it, some things just never get anywhere. It seems obvious that if an effort is never going to amount to anything and you’re not enjoying it any more, it’s time to quit. But how can you tell the difference between being nowhere and being close to making it?

A related question is, how do you know whether it’s worth the effort to start something? If you’re just going to quit later, is the initial rush of jumping in worth the fact that nothing will be achieved in this effort?

I think that depends on your goal. If you want to have adventures, have fun, or broaden your life experiences, it doesn’t really matter if you never “succeed” in the sense of accomplishing anything or achieving any goals. Start at will, enjoy it while you can, quit if it becomes a drag.

But if you have a particular end in mind, such as earning enough income to quit your day job, suddenly it’s very important to know whether your pursuit will lead to success, or whether you’re wasting your energy and should try something else.

Someone recommended that I read The Dip by Seth Godin. It’s a short little book on exactly this subject. The premise is that anything worth doing has a dip: the part where the fun wears off and you have to put in a lot of effort to get any results. If you make it through this phase, then the whole thing takes off again and you start seeing a lot of success fast, but most people quit in the dip and never make it that far.

Not everything has a dip, though. The other main model presented in the book is the cul-de-sac or dead end. In the cul-de-sac, no matter how hard or persistently you work, the thing will never take off. There will never be a big payoff at the end.

That much we knew already. The trick is how to distinguish the two. I don’t know about yours, but my life doesn’t come with a graphical readout illustrating a post-dip upsweep coming up soon, or a cul-de-sac flatline. (I’m imagining it appearing above my head, like that guy in Stranger than Fiction.)

The book offers a pretty radical answer: quit everything you can’t be the best in the world at. Then throw all your energy at getting through the dip on the one thing you will be the best in the world at.

Time to quit? For this broken boat, I'd say the answer is yes.

Image by Yogendra174, on Flickr

Specifically, if you’re trying to influence one person (as opposed to a market) and it’s not working, quit. If you’re not seeing any measurable progress, quit. If you’re in a non-growth situation, quit. (Examples here include dying industries and jobs with no room for advancement.) If these things are not true and you’re just panicking or frustrated, you’re in the dip–don’t quit.

This all makes sense to me. Also, the part about being the best in the world isn’t as crazy as it sounds. The trick is to define a small enough world. It’s like picking a dissertation topic when you’re trying to get a PhD: you have to become the world’s foremost expert in your topic in order to get a PhD. That doesn’t mean you have to become the world’s foremost expert in computer science, it means you pick some tiny, obscure tidbit of computer science that nobody has studied yet, study it, and poof! You’re the world’s foremost expert in it. Congratulations, Dr. You!

In this case, the assumption is that everything worth doing has a dip. That’s what keeps the rest of the competition out.

For something like word processing, Microsoft made it across the dip and then started digging it deeper and wider so nobody else could follow. You’d be crazy to try take on word processing as your next quest, unless you could come up with some radical new twist on it that changed all the rules.

But if you pick a smaller, specifically targeted market and make it through the dip, you can rule it. The trick is picking something where you have enough resources to make it through the dip. Everett Bogue seems to be a good example of this: tons of people are into minimalism, and tons of people are into making money online; he combined the two to make a small niche that he could rule, and did so.

Once you’ve identified what you want to pursue, the dip is your friend because it keeps the competition out. You just have to make it through yourself.

This makes a lot of sense to me. I’m still not 100% convinced that you need to quit everything you can’t be #1 at, but maybe he meant that more for “you” the company than “you” the person. I can say with a pretty strong degree of certainty that I will never be the best in the world at autocross; in fact, I’m pretty sure I’ll never be the best in the Huntsville, AL, club. I doubt I’ll even be the best female driver in the Huntsville, AL, club. But it’s a lot of fun, and it pushes me out of my comfort zone. I think it’s worth doing for those reasons.

I can definitely see the advantage of being serious about only one thing, though. Back in November, I was really excited about the revelation that it’s ok to try a bunch of stuff and let life sort out which things will work and which ones won’t. That makes a lot of sense to me, too, but actually trying to do it hasn’t been going all that well. I tend to get all obsessed about one thing and forget the others, then feel bad about neglecting them and try to catch up. I end up dropping most of the balls I’m juggling. Maybe it really would be better to focus on one thing. Obviously it would if I knew which thing to pick.

At least now I know what questions to ask. What small world do I want to rule? What dip is big enough to be worthwhile but small enough that I have the resources to get through it? What has to go so I can be #1 at what’s left?

Sometimes it’s actually easier to keep doing something than to quit, even if you know you should quit. Change is uncomfortable, and making decisions is also not a favorite among most people. I wish us all the courage to quit the cul-de-sacs and the determination to get through the dip. (And the wisdom to know the difference!)

1 Quitting quotes from

2Quote from

3I’m told the attribution was wrong on this one; here’s a source for the correct answer. Darn inaccurate internet. (Thanks, Lach!)

About Cara Stein: I'm a Breakthrough Coach and Creative Director On Demand. I'm also an idealist who has stopped trying to play it cool. I offer alignment, clarity, and unshakeable belief in yourself—and then I help you bring your vision to life with great sales copy and graphic design.

Comments (18)

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  1. Lach says:

    Well… I know ONE thing you’re going to be quitting PRETTY soon 😉

    I read an awesome little note the other day that I think might be just what you need to resolve some of that anxiety:

    “Persistence doesn’t mean knocking on the door until the damn thing opens. Persistence means knocking on all of them.”

    The vehicle might change, Cara. But you’re not a quitter so long as you keep the faith. You ROCK!

    • Cara Stein says:

      > Well… I know ONE thing you’re going to be quitting PRETTY soon 😉

      Hell yeah!! 😀

      Good point about keeping the faith. Seth Godin says kind of the same thing in the book I mentioned: quit tactics, but stick with strategies/big overall goals.

      Thanks, Lach! You’re pretty damn awesome yourself! 🙂

  2. Lucas says:

    Steve Jobs talks about the same thing. Dear to change. He talks about getting fired from Apple in 1985, life and death and how that was the best thing that happens to him! Check this YouTube video:

    • Cara Stein says:

      What a great video! It’s so easy to get discouraged and think it’s the end of everything when something goes wrong–so encouraging to hear how, in retrospect, those things were key to his success. Thanks for sharing that!

  3. Laurie says:

    Hi Cara, I found my way here via your comment at Lach’s blog…

    I don’t know how many times I’ve struggled with “the dip” myself…and then waste time worrying about the struggle! What I’m learning to do now is simply be in the moment and allow that to be enough. I have some big dreams and goals, after years of staying in one place and feeling rather stuck. What I had to do was choose a place to start and begin to find some clarity about what I truly want more than anything in the world…and that is FREEDOM. First finding freedom and empowerment within, gaining some much-needed confidence in myself, then looking at my dreams and goals without a bunch of “what if’s” and “yes, buts” in the way. It’s so exciting. 🙂

    I fully believe that if something’s not working, and you can feel that in your gut, then it’s time to quit. That’s different from quitting because it’s hard, or quitting because you’re in “the dip.” I used to approach everything with a bulldozer attitude, but I’ve found that if I just stop pushing so hard then things actually fall into place more easily and quickly. Who knew?!

    Your yarn-dying endeavors sound fascinating. I love crochet and I’m like a kid in a candy store when I’m in a yarn shop. Hope all goes well for you!

    • Cara Stein says:

      …and then waste time worrying about the struggle!

      Ooh, this is a big one for me. It’s not enough to worry or struggle or be discontent, I have to be meta-unhappy about being unhappy!

      Good for you for figuring out what you want and how to get it without so much struggle! One of my favorite of Lach’s insights is the one about how even when we’re trying to be positive, we’re often still making everything harder than it needs to be. Relax and go with the flow… I don’t know why that seems so hard to me! I hope it gets easier with practice.

      About the yarn, crochet is my favorite, too! Well, no, I like spinning even better. But yeah, the yarn-dyeing thing is cool and a lot of fun…when I don’t make it into work.

      Thanks for your comment! I hope I’ll see you around!

  4. ALBERT0 says:

    Good stuff! I think Tom Peters was talking about the dip in his famous entreaty to, “Fail forward fast.”

    Boldly try on new things, discover quickly which ones flatline, and roll on by with the ones whose dips are worth overcoming!

  5. ALBERT0 says:

    I’m not finding it as much now — I though it was in one of his writings and I’m sure it used to be really visible on his website…

    He’s got a tremendous amount of really good content in his (free) resources pages at and I know the ideas are in there, in his EXCELLENT and also downloadable _Innovation Tactics_ piece, “Innovate or Die” [subtitleS deleted, expletive it all!]

    I had to share this with you, too: another of my real favorites from his treasure trove, “The Heart of Business Strategy” is STUFFED with almost intuitive wisdoms that are way too often forgotten. AND, it’s challenging and FUN to figure out how to apply some of them in an electronically implemented business relationship.


  6. matt says:

    Great article on a great topic. I’ve been very interested in many of the same things, but unsure which ones to pursue and what things may be holding me back. Look forward to reading more from you.

    Really love your questions “What small world do I want to rule? What dip is big enough to be worthwhile but small enough that I have the resources to get through it? What has to go so I can be #1 at what’s left?”

    I’m going to remember that.

    • Cara Stein says:

      Thanks! For me, figuring out what to do next is always one of the hardest things, maybe the hardest. Good luck figuring it out! I hired a coach, which has helped immensely.

  7. Gee says:

    What a helpful post! It’s so true, asking the right questions makes all the difference in what we discover. Cara, I have been reading you for the last couple of days &just signed up for your ebook. You encourage me that there are some good answers out there for me, much appreciated as I consider paradigm shifts that sometimes have me feeling I stand at “the end of the world as [I] know it” ! Looking forward to having you as part of my journey- thanks!

    • Cara Stein says:

      Wow, thanks!! That’s my highest goal with this site. I can’t tell you how great it feels to hear that I’m helping you like that!

      I’m in a major period of transition myself, and it is really scary sometimes, but so exhilarating to conquer old fears, try new things, and make big changes! I hope it goes well for you, and let me know if I can help.

  8. Barb V says:

    “If you’re in a non-growth situation then quit.” Wow, that sooo speaks to me. It doesn’t always have to mean career advancement. Maybe it’s about growing mentally, spiritually, who you are as a person. I needed this right now. Thanks so much!

  9. babz says:

    mentioned this and the book on my show babzbuzz airs 12-1 I believe – LOVE THIS! bb

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