This post is from staff writer April Dykman.

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? Did you quit the cul-de-sac and lean into the dip?