How do you know when it’s time to lay down your cards or when it’s time to double down and push through?
Work & Life Lessons from The Gambler
While Kenny Rogers’ famous song The Gambler might not be your first stop when looking for life lessons on knowing when to quit, I think it’s worth a second look. Read on…
“You got to know when to hold ’em, know when to fold ’em,
Know when to walk away and know when to run.
You never count your money when you’re sittin’ at the table.
There’ll be time enough for countin’ when the dealin’s done.
Ev’ry gambler knows that the secret to survivin’
Is knowin’ what to throw away and knowing what to keep.
‘Cause ev’ry hand’s a winner and ev’ry hand’s a loser,
And the best that you can hope for is to die in your sleep.”
– The Gambler, Kenny Rogers
Ann’s Risky Gamble
What risks are you willing to take? I was recently introduced to a woman by a mutual friend at a swanky social event. We’ll call her Ann. As we were introduced, we quickly discovered we were all lawyers. Ann works for a large law firm doing commercial litigation and defending large companies, like mine. It seemed immediately clear to me that this woman had the same strength of personality and intelligence as our mutual friend. And, her modest, but visible tattoo, striking black hair, and 4 inch red heels showed a certain amount of individuality (maybe even rebellious nonconformity) in light of the very traditional trappings of a Big Law life.
I was impressed and imagined that she must have carved out a comfortable spot within that environment for the dynamic person she is. So when I told her that I had left law firm life a while ago to go in-house, her reaction surprised me more than most… I didn’t expect the to hear that she’d never wanted or expected to end up at a big firm or to hear her say, “sometimes I feel like it’s eating my soul.”
Sometimes I feel like it’s eating my soul??
She even said it in a nonchalant tone and with little recognition of the gravity of her statement. Rarely at a loss for words, I looked at her in surprise, with no response and no reassurance. There really wasn’t any to give at that point.
Life is full of risks, but gambling with my soul is not a risk I’m willing to take.
Hold or Fold?
Whether it’s leaving a job or a relationship, the decision making process itself isn’t something we talk much about. Plenty of people address what to do after you’ve left… Get back in the dating game, start your own business, or make the most of your first 90 days. But, deciding when to quit is harder.
Recently, I came across a book that addresses just this question. It’s called The Dip: A Little Book That Teaches You When to Quit (and When to Stick)
1) Am I panicking?
2) Who am I trying to influence?
3) What sort of measurable progress am I making?
To me these questions really get at the heart of the issue. If you’re panicking, stop and slow down. Good decisions are not made from that place. If you’re trying to influence anyone other than yourself, stop. It’s unlikely to work. And, if you aren’t making any sort of progress, then fold. Quit quickly, and go do something else with your time.
Every Hand’s a Winner & Every Hand’s a Loser
I’m sure that Ann’s job originally provided her an amazing opportunity in the beginning to go along with the baggage that inevitably came with it. The question is exactly when along the way did that job become such a loser… And how can we avoid staying too long?
Godin’s suggestion is to decide when to quit before you even start. He quotes ultra marathoner Dick Collins who said “[d]ecide before the race the condition that will cause you to stop and drop out. . . If you are making a decision based on how you feel at that moment, you will probably make the wrong decision.”
“The best quitters . . . are the ones who decide in advance when they’re going to quit.”
“If quitting is going to be a strategic decision that enables you to make smart choices in the marketplace, then you should outline your quitting strategy before the discomfort sets in.”
Deciding ahead of time when the job no longer works for you, would minimize staying too long out of the simple fear of change or an overdeveloped sense of loyalty. Looking forward strategically about when to quit would also make us more conscious about positioning ourselves to make an impending big move – both financially and emotionally. This an idea that I’ve chosen to adopt. Knowing that when the ace drops, it’s time to fold sounds like a better idea than simply continuing to add to the pot only to find out in the end that my hand is a loser.
Note: I recommend reading The Dip, and I think it provides plenty of value to merit the $9.32 cost on Amazon, but I do have one note of caution for you… I found Godin’s advice about becoming “the best in the world” – i.e. not quiting and pushing through the Dip – to be lacking and overly simplistic. So if money is tight, seek it out in a used bookstore or just spend a few minutes flipping through it on your next trip to the Barnes & Noble.
The Best that You Can Hope For
So here’s where I recommend taking leave of The Gambler’s advice. There’s plenty more to hope for than “dying in your sleep.” Change can be hard, but it’s also good.
As many of you already know, I gave my resignation at the end of July to the company I worked at for 5 years. The company where I first became an officer, where I knew the CEO and executive team personally, and where most of them had been there from the beginning as shareholders. The company had faced some challenging times due to overseas expansion and was purchased in April. It wasn’t an easy decision for me to go, but it was time for a change.
Maybe I stayed too long to begin with or maybe I finally got it right. Otherwise, I wouldn’t have been there to take the exciting opportunity that came along.
What do you think about deciding the conditions under which you would quit before you actually start?
