How to Know When to Quit

Before I became a full-time freelancer, I worked for a couple of different companies. Both times I started a new job, it started out exciting and fun. Great benefits! Cool perks! Interesting work!

After a year or two, it got harder to get up in the morning and face an eight-hour day of doing whatever it was I was hired to do. By years three to five, the shine was wearing off, and finally it was clear that I needed to quit my job. I'd tried to make proactive changes, but it was time to move on.

Winners never quit?
This move-on point is what bestselling author Seth Godin calls a cul-de-sac in his book The Dip: A Little Book that Teaches You When to Quit (and When to Stick). He says when you hit a cul-de-sac (French for “bottom of the bag,” meaning “dead-end”), it's time to quit. This sort of advice is quite unlike the winning and failing quotes we hear so often in our society, such as:

  • “Quitters never win.”
  • “Thomas Edison failed more than 1,000 times before he invented the light bulb.” (Others actually produced incandescent lights before Edison. He did create the first practical light bulb and an electrical system to support it.)
  • “Boom, crush. Night, losers. Winning, duh.”—Charlie Sheen

It's all about winning, and winners never quit, right? Well, that's not entirely accurate. “Winners quit all the time,” writes Godin. “They just quit the right stuff at the right time.”

Cul-de-sacs go nowhere
We've talked a bit about the cul-de-sac, but let's explore the end of the road a little more. In this situation, you've tried to make proactive changes and find solutions. Maybe your ultimate goal is to work two days at home each week. You've written a proposal that outlines a solid plan to make it work, along with a no-obligation trial period, but it was shot down because your boss is a micro-manager who doesn't trust her employees. Maybe you've tried to make your neighborhood ferret-sitting service a success, but the market isn't there, and you're realizing that your niche is too narrow.

It's time to move on; you've probably hit a dead end.

Leaning into the dips
But what about those countless stories of famous people who overcame adversity and rejection, never losing sight of their goal? A few examples:

  • The Alfred A. Knopf publishing house rejected books from Jack Kerouac, George Orwell, and Sylvia Plath.
  • Before Disneyland and Mickey Mouse, Walt Disney started a company called the Laugh-O-Gram Corporation that filed for bankruptcy when financial backers pulled out.
  • Stephen King received 30 rejection letters for his first novel, Carrie. His wife pulled it out of the trash and encouraged him to submit it again.

Not to mention the Vincent Van Goghs, celebrated posthumously, but never receiving recognition in their lifetime — yet Van Gogh never quit painting. We kind of love these stories, don't we? They're inspiring. But they don't necessarily translate into practical advice, unless you're okay with being a penniless painter who struggles with anxiety and mental disorder. I'm going to guess that most GRS readers don't fall into that category.

So how do you know when to keep going and when to call it quits? Godin says if you haven't hit a cul-de-sac, you're probably at a dip. In the beginning of anything new, you're excited. You're learning, doing fun things, and you feel energized. Then you hit a dip. You're assigned a project you don't want. You realize that being a freelance writer doesn't just meaning working from home in your yoga pants, it also means invoicing and marketing. You're blowing through your piano music only to hit a major wall at the 12th measure of Chopin's Prelude in E Minor Op. 28 No. 4.

“The dip is the long stretch between beginner's luck and real accomplishment,” writes Godin. “[It's] the set of artificial screens set up to keep people like you out.”

What's more, Godin says successful people don't ride out the dips or merely survive them. They don't hide their sheet music in the piano bench, hoping the teacher will forget about Chopin. “…they lean into the dip,” he says. “They push harder, changing the rules as they go. Just because you know you're in the dip doesn't mean you have to live happily with it.” In fact, by leaning into it, you can shorten the amount of time you spend in the dip.

Winners are strategic quitters
No one wants to go down on a sinking ship or stick around because they're complacent or afraid to quit. Maybe you're out of money and you've sunk too much into a failing project. Maybe you've lost interest. Maybe you picked the wrong venture and simply don't have the talent. Ouch. That's a hard pill to swallow, but it's sometimes true. We aren't all capable of being prima ballerinas or NBA superstars — what is your goal? Have you had any indication that it's attainable?

On the other hand, reactive quitting and serial quitting won't get you anywhere in life. You also can't quit every time a situation is uncertain or difficult, because as Godin points out, most things that are worth doing have dips. How do you know if you're cutting out too early? He says to ask yourself the following questions:

  1. Are you panicking? Don't quit when emotions are running high. You should always decide to quit when you are calm and thinking rationally.
  2. Who are you trying to influence? Influencing one person (your boss, for example) is often harder than influencing a market (such as potential clients for your start-up). Figuring out your audience can shed light on your potential for success.
  3. Are you making measurable progress? With any goal or task you set out to accomplish, you're in one of three positions: falling behind, standing still, or moving forward. This is true of careers, relationships, and finances, to name a few. If you're not moving forward even to a small degree, or at least standing still with some forward progress imminent, it's time to think about your strategy.

Quitting doesn't necessarily mean ending a relationship, turning in your two weeks' notice, or abandoning your business because sales are slow for a couple of months. You also can quit a tactic or a project. Sometimes quitting just means refocusing or finding a new approach. But rather than seeing it as a failure, quit strategically and realize it's an opportunity for greater success, or identify a dip as a dip and lean hard.

Speaking of leaning, I guess it's time for a certain Chopin prelude to come out of hiding.

What's an example of a cul-de-sac and a dip in your life? D id you quit the cul-de-sac and lean into the dip?

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Mondo Esteban
Mondo Esteban

My work commute consists of being in unpredictable city traffic two hours a day, time to quit?

Matt Bell
Matt Bell

Wow – really good article that hits me right in my self-employed heart. Godin’s comment that “The dip is the long stretch between beginner’s luck and real accomplishment” really struck a chord. I think anyone trying to accomplish something difficult finds it tough to balance the fear of being a fool on the one hand and the sense of mission that drives you forward on the other. There are no simple answers as to when to quit and when to press on, but the questions in this article are really helpful.

El Nerdo
El Nerdo

A more fitting term for cul-de-sac is DEAD END. Two short and brutal Germanic words, even a little redundant (“the end” is also death: dead death). Dead end: It’s definitely dead, and it stinks of carrion, and the air is thick with flies– you know the feeling when you’re stuck there: the despair in the pit of the stomach, the urge to flee in any direction, the howling invocations for the swift arrival of the weekend, the dreams of punching the boss in the face, the very large bar tabs fattening your credit card balance, the burning jealousy when you… Read more »

chacha1
chacha1

Same reason I stopped at an M.A. My advisor told me the best career move she ever made was not letting *her* advisors know she could type. I have made more money as a glorified typist (and had easier working conditions) than I ever would have teaching undergraduate history surveys.

El Nerdo
El Nerdo

Smart move. The life of the adjunct is a thankless one.

KS
KS

My story was similar. I was 2 years into a PhD program in biophysics that I hated. I hated my classmates, my faculty, my work. I was miserable, crying, and physically ill from what I was doing. One day, I realized I couldn’t take it anymore. I went in when I knew people wouldn’t be around to collect my things. I had $1000 in the bank. The next week, I ran into an acquaintance I hadn’t seen in years. When I told her what I’d done, she told me her lab had a job that would probably tide me over… Read more »

El Nerdo
El Nerdo

That’s a great story. We really need people doing doctoral-level research, but sometimes academic departments seem to believe that’s the only kind of educated person the world needs, and the truth is that the world is clamoring for skilled professionals more than anything else.

Tami
Tami

What is your life’s work?

Heather
Heather

Thanks El Nerdo, Chacha1, & KS for sharing. I am glad to hear others’ stories about leaving school. I was almost through a masters program with aspirations to go on into a PhD program but got a job that I discovered was my passion and the thesis got slowly put on pause until I admitted I really didn’t want to go back. I’ve always had kind of a nagging feeling about quitting – mostly due to those kind of societal platitudes that April related. But instead of more student loan debt, I have time to spend with my family and… Read more »

ZA
ZA

I finished my PhD, last year, while working full time in the field my degrees are in, education. My goal was simple-I wanted to have options and interesting questions to ask and problems to solve. Well the great job I was in ended, and I got another, not so great one. I didn’t get my degree for a job like this. But it’s work, adds a skill set and nice looking title to my resume. I’ve been in it 6-months and I’m already looking for another, not because I want to quit, but because I want a job that’s a… Read more »

Laura
Laura

“…the howling invocations for the swift arrival of the weekend” – ROFLMAO! I think this goes at the top of my projects/to-do notebook at work. 🙂 If you met your wife in grad school, that is probably the reason why you were there – not the PhD, hence that felt like a dead end. You got the right thing out of it, then left. There’s an anonymous quote that people come into your life for a reason, a season, or a lifetime. Same goes with work situations, I think. If you got what you’re supposed to from it, then it’s… Read more »

El Nerdo
El Nerdo

Well, getting my M.A. was a delicious experience, 100% brain candy, and I thought that getting into the PhD I though was a “dip” of sorts, until I realized that no, there was no exit, no job prospects, the “heroes” of my department were not getting the kinds of jobs I wanted, and working for years on a dissertation without funding was a fool’s errand. My wife’s story is way more dramatic– she was actually conned into accepting a fellowship for a department that was closing, and nobody told her until she showed up, so they stuck her in some… Read more »

Megan
Megan

I quit my steady job last year to freelance and stay at home with the kids. I haven’t looked back – and my only regret is not doing this earlier – but it’s been hard. Prospects have dried up, the “I’ll call you backs” never do, and “We’ve already filled that position” pile up. That being said, I just keep plugging away. I’m in a dry patch, so I’ll punch up my professional website and cold-email people. I make myself so busy drumming up new business that I don’t really have time to sit and think “Gee, I don’t have… Read more »

Jeff
Jeff

I worked for a large company for 6 years and it was good but progressively got worse. I was miserable in my job, my boss was a jerk, and there was no end in sight. About 1 time a year from years 3 to 6 I would consider the thought of leaving to start my own company in the same line of work but each time I would chicken out and stick with what was safe. Finally in year 6 I’d had enough and took the leap of faith to go out on my own. Now I’m 16 months into… Read more »

29 and holding
29 and holding

I have read several of Seth Godin’s books. I admit I can’t understand them. It’s airy, high level advice that isn’t something I am able to internalize and use in my life. I concluded after reading his last book that, really, he’s very good at marketing his books…yes okay, figure out when your efforts are not getting you anywhere and find a new gig. Is this new advice? um no. Sorry Seth (and April!)

David
David

I’m with you. I subscribed to his blog for a while cause he provides little tidbits that make you feel good / smart, but then you realize it’s all fluff.

I think there are definitely good marketing lessons to learn from Godin, but they’re not the ones that he’s writing down in his books…

Jacq
Jacq

I quit my dreams of becoming a writer and focused on a higher earning career that I was very good at but wasn’t as wow-glamorous. This is why:

What’s the difference between an English major and a large pepperoni
pizza?

The large pepperoni pizza can feed a family of four.

El Nerdo
El Nerdo

haaa haaa haaa. yes.

Suz
Suz

And yet, now you have a good paying job. And you were an English major. Amazing. English majors get lots of different jobs; they’re not all trying to be writers. And guess what? Even writers sometimes can feed a family of four! (This blog we’ve just read–case in point.)

El Nerdo
El Nerdo

Okay, but it was a good joke, wasn’t it?

chacha1
chacha1

Jacq didn’t quit being an English major. S/he quit trying to be a full-time writer.

The fact that s/he now has a good-paying job is due to facing up to the fact that 99.9% of would-be full-time writers don’t make enough money to live on.

Jacq
Jacq

What ended up happening was that I really enjoyed accounting but loved writing. I was very good at accounting but the really good jobs in accounting don`t come along until you put the years in. Lots of people give up before then and call it *soul sucking* when it really isn`t later on if you have any aptitude for it. The writing was very iffy because it`s such a subjective field. Oddly enough, I ended up writing business and marketing plans and later annual reports etc., so sometimes things happen in very strange ways. I`ve read a lot about the… Read more »

Laura
Laura

I’m an English major and I just shared this with my family and English major friends. Love it!

retirebyforty
retirebyforty

Good visualization about cul-de-sac and dip. I feel like I’m at a cul-de-sac in my current job. There are opportunities to grow, but I don’t want to do it. If I just keep doing the same thing, then I will get left behind. It’s going to be quitting time soon. I think I’ll be happier with self employment so I’ll try for a few years and see.

Bella
Bella

This is a great comment – maybe sometimes the difference bewteen a dip and a cul de sac is knowing if you can/want to lean in. I recently changed jobs – to do something completely different – at the same company. It was hard to finally come to the realization that while I could do my old job – it was killing me – that leaving wasn’t quitting but recognizing that my strengths and interests lay elsewhere. Boy – I wish I had made the switch sooner, but at least it’s made now.

Dogs or Dollars
Dogs or Dollars

This is where I’m at. I could do better. Be more motivated. Move up the corporate ladder. But why?
I make enough money. I certainly don’t want anymore responsibility. I’m not interested in the subject matter. But stagnating kind of sucks too.

Isn’t it ok to just ‘have a job’? Must it be the end all be all of your existence?

29 and holding
29 and holding

No, it doesn’t. I think realizing that your life does not begin and end in one thing, whether it be a job, a hobby, or family, but is instead the sum of all its parts, that is just part of maturing into an adult. You don’t have to pursue One Big Dream, you can have lots of little goals and still be fulfilled.

Masky
Masky

So right! I ve never believed in d “Big Dream” be it job/career, family,lifestyle. Because your life does not consist of just one thing, its d sum of all dis little aspects. This of course does not mean u don’t have a picture of what you want in each of dis areas,it just mean that one area should not define you.

Sara
Sara

I feel the same way. I’ve decided that it’s ok to just have a job and work on other areas of my life. My job makes me happy, but it isn’t a life passion. I’ve had offers to go to other companies for more money, but I’m kind of happy here. I’ve decided to work on more personal growth than career growth.

Beth
Beth

They just did a great story on this same subject on NPR a few days ago.

pc repair
pc repair

Don’t give up, people. Here’s another stat: Babe Ruth was called the greatest hitter of all time. But he struck out 1,322 times. So like Jim Valvano said “don’t give up. Don’t ever give up.”

Samantha
Samantha

That reminds me of the Michael Jordan “failure” ad for Nike:

http://www.youtube.com/watch?v=45mMioJ5szc

Holly
Holly

I have noticed here on GRS that I cannot always use the scroll bar and that very often only the arrows at the top and bottom will work.

I noticed it began at the same time that this site allowed boxes of links to magically appear and disappear on the bottom right.

Could it be the browser that I am using?

Anyone out there experiencing this?

Carla
Carla

Holly, I have the same issue. I use Google Chrome by the way. This just started a little over a month ago…

29 and holding
29 and holding

Yeah, this site isn’t very good with Chrome.

louisa @ TheReallyGoodLife
louisa @ TheReallyGoodLife

Like the other self-employed people on here, I experience ebbs & flows of work and enthusiasm – some projects make it through the dip, others get abandoned by the roadside. I don’t have the time or energy to pursue each one so it’s better to abandon some to meet my bigger goal: to stay self-employed.

I do sometimes have “what if” moments where I wonder what would have happened if I had pursued X or Z further rather than leaving them in the dip but that’s even less productive than pointlessly slogging away at something with no end in sight.

Krantcents
Krantcents

I have quit a few and never let a dip stop me. I am usually successful achieving my goals although it may take longer. Most of my life, I was either self employed or had control of my future. My worst attribute is I don’t know when to give up. Now I am in the last years of semi-retirement and will officially retire in less than 6 years.

Ru
Ru

“But they don’t necessarily translate into practical advice, unless you’re okay with being a penniless painter who struggles with anxiety and mental disorder. I’m going to guess that most GRS readers don’t fall into that category.” I’m a penniless ceramicist (with the extras you mentioned too!) and that’s worse because the public don’t want to pay a fair price for your work when they can get a plate at Ikea for 50p and the art world looks down its nose at your “craft”. When I recently considered quitting, my mum reminded me of my sunk costs and efforts (and me… Read more »

Bella
Bella

Ru, as a potter (though in my spare time) I completely agree with the sense of craft versus art – but getting an advanced degree in a creative field is still a good thing if you can parlay it into a job that pays well and lets you be a little creative. Besides – isn’t tuition at least free in the UK?

Ru
Ru

No, tuition is not free, it’s £3000 a year, but with our student loan system I don’t have to pay that back until I’m earning 15K or more (which isn’t a living wage in my part of the country). That gets paid straight to my university, and I get a maintenance loan of around £4000. It’s more the cost of living that gets me- the loan doesn’t even cover my rent in London, which is why I’m living with my parents and commuting 3 hours every day I decide to go in. Worse comes to worse, I go back to… Read more »

Stellamarina
Stellamarina

I think that anybody who is studying any kind of art also needs to take business and marketing classes as part of their education.

Ru
Ru

My course is pretty good for that, we meet lots of established ceramicists (Kate Malone, Julian Stair, Michael Eden, Cynthia Vardhan), and talk with them about the risks they take, how they established their business, how they price their objects, what problems they’ve had on the way. Part of every project brief is identifying the market you plan to sell to, and we’re expected to talk to retailers too.

I’ve got so much out of this course that I never could have learned on my own, so it’s totally worth all the pain and effort!

Amber
Amber

A couple of years back I learned my ‘time-to-quit’ signs. – sleeping in more frequently resulting in getting into to work late…and eventually not carry about tardiness (being in usually 30 mins early is my normal ‘happy’ routine) – Dreading going into work the following day, which usually starts at the end of the current work day, souring my mood for the evening. – Increased periods of illness. – Finally coming home in tears because I can’t stand the idea of going back. At this point I hand in my resignation and tell them to keep my vacation pay. I’m… Read more »

C. Hernandez
C. Hernandez

I started out as a sales representative out from college and in just couple of years have my own agency. I love what I do because it provides me with the ability to work on my own and being able to have my team and help them. Freelance work also helps me save time to spend with my loved ones.

Gail
Gail

Up until a few years ago, I enjoyed my job but I think it was because of the people I worked with. It was not my whole life and I had a fulfilling life outside of work (family, hobby). About 2 years ago, things changed. I no longer liked my job and realized that I was stagnating. I decided to go back to school to become a teacher. I have had to stick it out at my job for financial reasons. It has been excruciating. Some days, I want to walk outside in a lightening storm with metal shoes on!… Read more »

Squirrelers
Squirrelers

I actually think that Godin’s right about this one. In our society, there is sometimes a stigma associated with quitting. Just the notion of giving up is deemed as acknowledging failure, or not having enough perseverence or work ethic. While that may be true in some cases (as perserverence can actually be a tremendous thing in many cases), it’s foolish to have a general assumption that only losers quit. Sometimes, it’s smart to give up on something and just flat out quit. When we reach dead ends, we need to move in different directions. No shame there, and it could… Read more »

UltimateSmartMoney
UltimateSmartMoney

I know I will never quit my day job. Why? Because it is easy income for me and my family. However, I have no idea what’s in store for my future since my company can lay me off at anytime due to no work. That’s why I have to have my resume polished often just in case.

Vince Thorne
Vince Thorne

If you are learning a skill worth learning thenn quitting might be the wrong decision even if success is elusive. If you are learning nothing but succeeding, you are likely not thinking of quitting (and you may be on either side of wall street). If you are learning nothing and not succeeding then it is time to move on.

Cherleen @ My Personal Finance Journey
Cherleen @ My Personal Finance Journey

I do the same thing. When I feel that I am already dragging myself to work and watching the clock as I finish my task, then I know that is the time for me to look for another job and move on to another company.

I don’t believe that quitters never win. There are those who quit their day jobs and pursued a business or interest, and then succeeded. Look at the positive side of the coin.

Project Management Tools That Work (Bruce)
Project Management Tools That Work (Bruce)

“Quitting” is kind of like “retirement” – the word can be misleading. I rarely use either word as they only confuse people. The only time I ever felt I quit was from the high school basketball team in the middle of the season. I joined the team because “guys do sports” but I had no real interest. I went on to eventually win two state championships in speech and debate. That was something I had a passion for (along with computer programming which became my early career). Since then I’ve changed jobs and careers when it was obviously time to… Read more »

Carsten
Carsten

Just for future reference, the plural form of “cul-de-sac” is “culs-de-sac.”

unsettled_guy
unsettled_guy

“Influencing one person (your boss, for example) is often harder than influencing a market (such as potential clients for your start-up).”

I really like the article, but I’m not sure I agree with the above point. It may be hard to influence your boss, but harder than influencing an entire market? not sure about that…

Ben - BankAim
Ben - BankAim

Thanks April, this is what I needed to hear. “Don’t quit when emotions are running high. You should always decide to quit when you are calm and thinking rationally.” Business online can be brutal and very discouraging. I was just talking to my wife today about how difficult it is to make a living online. Some recent events have caused my emotions to run high, like you have said. I need to wait to calm down and then get rational with my situation. I know once I calm down I start to dwell on the possibilities and how huge the… Read more »

marc
marc

This post hits home with me. I just turned 40. Been with the same mid-sized company for 10 years now – never thought I’d stay with one company so long, but, quite frankly, it’s been easy money. The first 6 years were flat-out great. I was learning cool stuff, got to travel the first couple of years, and had extremely flexible work hours. Commute is 10 minutes each way. Then I was promoted to supervisor, and now manager. I hate it. A couple of the people I manage are flat-out useless. It’s so frustrating. But, it’s a 6 figure salary,… Read more »

ES
ES

Wait! Make the move when-and if- you see something that sparks your interest. It’s always easier to move on if you have a specific goal.

Jennifer
Jennifer

I’ve had the same part-time job for 6 years, while I stay home with my kids the rest of the time. The new baby is due any day and I’m trying to decide whether or not to return to work after he’s born. The owners of this small business trust me implicitly, and let me do basically whatever I want. But I’m 30, and I’m maxed out in the industry. It’s the restaurant business, and I work for the nicest place in the city in a high-level position. But I never want to open a restaurant. So, maxed out. I… Read more »

BD
BD

“unless you’re okay with being a penniless painter who struggles with anxiety and mental disorder. I’m going to guess that most GRS readers don’t fall into that category.” Well…that actually is EXACTLY the category I’m in. But I’m working to get out of that category. Being penniless really sucks, and there is no money in being an artist. And with no money, it’s hard to get the medication I need for the other two problems. So yeah, I’m trying to change things around. I had my “this is when to quit” revelation 2 years ago. I gave up trying to… Read more »

Mr. bodybuilding
Mr. bodybuilding

Lol, whenever I felt too tired of a job or boss I would always WANT to quit but it takes me forever to do it and by the time I quit I dont feel like doing any other work for the rest of my life. But now I know better..

Robinson Mertilus
Robinson Mertilus

Excellent article. The most successful people know how to get started and how to stop. They tend to pick the best times to do so.

Trina
Trina

Thanks for this! This is one of the best stories I’ve read on GRS in a long time!

Sonja
Sonja

After trying to get a different positon in the company I was working in for a year I quit. This partly was an emotional decision, but it was a good one. Being stuck in the dead end drained my energy. It stopped me from finding out what I’d rather do and go at it.

Quiting my job (without any security) felt great.

I’ve now recently started a new position after three months being unemployed. Yes I could have applied for jobs first, but for me this was the way to break out of the dead end.

Mario
Mario

I’ve left too many jobs that I felt weren’t a perfect fit. What I think I’m quitting is quitting (for a while at least). Thankfully, I absolutely love my current job 🙂

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