Should I Stay Or Should I Go

The Clash’s hit song Should I Stay or Should I Go is about the end of a broken relationship.

It’s also a question every professional struggles with at one point or another in their career.

Right now, it’s THE question being debated in the corridors of power and across the media as it relates to President Joe Biden’s reelection campaign.

Don’t worry, this isn’t a blog about politics. All of us get enough of that already. But the non-stop coverage of the President’s candidacy does present an opportunity to explore the idea of quitting.

Grinding it out, never saying die, fighting through adversity are part and parcel of the American dream.  Quitting or giving up runs counter to how we define success.  There are a zillion quotes out there from successful people from all walks of life about the importance of hanging tough against the odds.

“Nothing in the world can take the place of persistence” – Calvin Coolidge

“Never give up, for that is just the place and time when the tide will turn” – Harriet Beecher Stowe

“Nothing is impossible.  The word itself says: ‘I’m possible.’” – Audrey Hepburn

I’m a big believer in this type of motivation.  A replica of the “Believe” sign from Ted Lasso hangs above my desk.  My last blog post was about the importance of developing a willingness to endure uncomfortable challenges to achieve sustained professional and personal growth. 

Last year I decided to launch my own business after thirty years in corporate America.  Lesson number one for any entrepreneur is perseverance.  If you want to make it on your own, you have to learn to fight through doubts and ignore the naysayers.


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Every entrepreneur, myself included, finds inspiration in the stories of other business owners who fought through tough times only to emerge on the other side as runaway successes.

I’ve experienced this as well in my side hustle of fiction writing.  Pursuing any artistic endeavor requires massive amounts of will and self-motivation.  Because the odds of breaking through are so long and the time required to produce work is incredibly substantial, it’s very easy to find reasons to quit.

Yet every writer can point to stories like those of Stephen King and John Grisham, both of whom were rejected hundreds of times early in their careers, as inspiration to keep going.

So, if you ask me on a given day “should I stay or should I go,” my answer is an emphatic, “Hell, yeah, I’m staying.”

But is it really true that one should never give up?

Never, taken literally, means never.  As in under no circumstances, don’t even consider it, forget it.  It’s an absolute.  That’s the point, we set our mind to something and don’t allow anything to change it.  After all, if we don’t believe in ourselves or our abilities, no one else will.

But there are very few absolutes in life. Success is more than a function of hanging on after everyone else has let go. All this never give up “rah-rah” stuff sounds great, but let’s be real, there are unquestionably times in our professional lives when continuing to bang our heads against a wall is stupid and counterproductive.

Most new businesses fail.  Sometimes it’s because the person or people behind them gave up too early.  But more often it’s because either the idea or the execution wasn’t embraced by the market. 

The same is true for those in corporate America.  The promotion you’ve been chasing, the client you’ve been pitching, the new brand campaign you’re managing; it takes grit and determination to make these things happen.  If you give up at the first sign of resistance you won’t achieve anything.  But maybe what you’re selling just ain’t good enough.  Continuing to push bad or flawed ideas could do great damage to your career.

Persistence may be omnipotent, to quote Coolidge again, but it’s also true that the definition of insanity is doing the same thing repeatedly and expecting different results.

Every successful person has quit at some point.  And for good reason.  To believe one should never quit is to believe in one’s own infallibility.  (This is one of the many problems with the other candidate running for president, but I digress.)  All of us make mistakes. Our judgement isn’t always perfect.  Our abilities or ideas aren’t always made for the moment. Fortitude and a willingness to fight through struggles are foundational to success and accomplishing hard things.  But so are humility and the ability to maintain an open mind.

How does one know whether the obstacle in front of them is meant to be plowed through or a sign to pivot?

Unfortunately, there’s no instruction manual, full-proof formula, or crystal ball for giving us the answer.  Sometimes it comes down to the moment and circumstances.  Timing, as they say, is everything in life.  For those of us in our peak years, we must rely on the wisdom and experience we’ve accumulated over the decades to make the best decisions we can.  And, yes, sometimes we need to trust our gut and believe when no one else does.

I think the key in the end, however, comes down to one thing.  We must always be willing to honestly ask ourselves the “should I stay or should I go” question.  To truly ask it with an open mind means we are prepared to accept that the answer could be “it’s time to go.”  Quitting always should be an option. 

Those who quit aren’t failures or weak-minded.  The business people, entrepreneurs and artists we see as role models of perseverance, often quit many times along the way.  They pivoted to a new idea, explored other methods or went in different directions.  They learned when to accept failure, learn from it, and move on.

There’s a great line in Should I Stay Or Should I Go, “If I go it will be trouble, but if I stay it will be double.” The protagonist in this song clearly is struggling with the question.  Joe Strummer, Mick Jones and the rest of The Clash surely did not set out to write a song about keeping an open mind about quitting.  But their classic touched upon a fundamental truth: quitting, it turns out, isn’t anathema to success, it’s an integral part of it.


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