tl;dr is in the one-to-last paragraph:

“A quitter never wins and a winner never quits.” In 1937, a self-help pundit named Napoleon Hill included that phrase in his very popular book Think and Grow Rich. Hill was inspired in part by the rags-to-riches industrialist Andrew Carnegie. These days the phrase is often attributed to Vince Lombardi, the legendarily tough football coach. What a lineage! And it does make a lot of sense, doesn’t it? Of course it takes tremendous amounts of time and effort and, for lack of a more scientific word, stick-to-itiveness, to make any real progress in the world. But time and effort and even stick-to-itiveness are not in infinite supply. Remember the opportunity cost: every hour, every ounce of effort you spend here cannot be spent there. So let me counter Napoleon Hill’s phrase with another one, certainly not as well known. It’s something that Stella Adler, the great acting coach, used to say: Your choice is your talent. So choosing the right path, the right project, the right job or passion or religion — that’s where the treasure lies; that’s where the value lies. So if you realize that you’ve made a wrong choice — even if already you’ve sunk way too much cost into it — well, I’ve got one word to say to you, my friend. Quit.

There is a problem solving perspective in which one is searching a tree of sub-goals. Nodes that are a conjunction of sub-goals are straight forward. You have to solve all the sub-goals, so if you get stuck on one of them you mustn't quit.

Nodes that are a disjunction of sub-goals are much harder to manage. Sometimes the problem is solvable (because, say, the 10th sub-goal is solvable) but the first 9 sub-goals are insoluble. You cannot solve the problem without quitting on nine of the sub-goals (or quitting on your original choice of search order).

Life often throws you problems that you cannot solve if you refuse to quit (from failing sub-goals). Sometimes, taking the attitude that "a winner never quits" guarantees failure.

There's a difference between "quitting" and "putting your energy elsewhere". The second is a good thing, the first is just giving up.

Yeah, the article addressed that pretty well:

VENKATESH: So one of the strange things we found out when we spoke to baseball players is that they have their own language for quitting. They actually quit. They just don’t call it that. They don’t call it quitting. They don’t call it giving up. But, they say, “You know what? I’m just going to shut it down for a while.”

VENKATESH: So, what does it mean to be a quitter as opposed to a “shutter downer”?

HALL: Probably the same thing, is just sounds better when you say ‘I’m just shutting down.’ You know, it’s like you’re not really doing it, but, you know, you are.

Seth Godin's "The Dip" talks about this and knowing the difference between a dip and a cul-de-sac.

Agreed. "The-Dip" is a great read on this topic. His basic premise is great in the sense that it's not about quitting or sticking into something for sake of stubbornness.

It's all about knowing what It'll take to quit before hand, see if it's worth starting, and improve the odds of making it past the dip.

Unfortunately I had to quit the article about halfway through. It being a transcript of a radio broadcast made it pretty hard to follow, at least for me, but what I read was pretty fascinating, especially the part about the baseball player.

Does anyone know if there's a version of this that is formatted as a article?

Link to their podcast -- more enjoyable than reading a transcript.

http://itunes.apple.com/au/podcast/freakonomics-radio/id3546...

No... but you can probably find it in audio-form on the freakanomics podcast, if that would go down easier.

From the examples, it sounds like the answer to the question "when should I quit" comes most easily when you have some source of objectivity.

It's easy, from the outside, to see a baseball minor league player in their early 30s and think "he would be better off quitting." The hard part is to accept that idea from the inside. Sometimes having a dream to be striving for is nearly as rewarding as success itself.

This reminds me of Rickey Henderson, who played for 25 seasons, played minor league ball when he was 48 and still refuses to retire.

I listened to this over the weekend. It was entertaining, but can be summed up with "Sometimes you quit too early, sometimes you quit too late" from somewhere in the middle of the program.

Not a lot of hard data, but some interesting anecdotes.

The podcast also highlighted the importance of "failing fast," or figuring out what will or will not work as soon as possible, and adjusting accordingly. This iterative approach to finding success seems to pervade start-up culture, and in my instances, is very sound advice IMHO.

I hate the word "pivot" because it's over-abused in startup parlance, but I like it as a way to describe smart navigating -- not just in startups per say, but maybe also in the bigger game of life as well.

I think it's important to remain focused on one big long-term destination/path, but still be flexible to "quit" short-term and change directions along the way to eventually get there.

"If at first you don't succeed, try, try again. Then quit. No use being a damn fool about it." -- W.C. Fields

Can't remember the source ... "If at first you don't succeed, destroy all evidence that you ever tried."

Or just make it so banal on your resume no one will care to check.

"Tamed tigers for a circus" becomes "Shoveled cat poop".

Here is the MP3: http://audio.wnyc.org/freakonomics_specials/freakonomics_spe...