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Should I stay or should I go? -- Career insights from The Clash


Should I stay… or should I go? I cannot consider that question without The Clash’s 1982 punk rock anthem* ringing in my head. All it takes is a couple notes of the classic opening riff and next thing I know I’m transported back to the Sigma Chi house jumping up on the coffee table with Rob Lee, my regular dance partner/ freshman crush. We'd thrash around in as punk rock of a way as you can when you’re students at William & Mary** at the preppy Sigma Chi house. But I digress…

The song addresses the real pain of indecision. If you aren’t familiar with the song, the lyrics go:

Should I stay or should I go now?

If I go, there will be trouble

And if I stay it will be double

So come on and let me know

This indecision's bugging me

If you don't want me, set me free

Exactly whom I'm supposed to be

A relationship that was exciting at first has gotten a stale and things are at an inflection point – can they continue with this relationship or is it time to break?


Punk rock wisdom


As strange as it may seem to glean career wisdom from punk rock, this song echoes what often happens when you've been in the same role or same company for a while. When you first get a new job, you’re so thrilled. You were courted during the interview process and finally singled out for the offer from among several other candidates. You feel lucky and special. In some cases, you can’t believe we’re getting paid to do this job! Then after being in the job for a while, you start to lose that initial excitement and then perhaps after years you’ve rationalized the reasons for staying. But how do you know when it’s time to go?

I recently met Jason*** who had been in his job with a small advisory firm for nearly 20 years and had risen through the ranks to Chief Administrative Officer – the one who knows how everything works and where the proverbial bodies are buried. Yet he’d also just been informed that he was not on a partner track. That was a huge blow to him and caused him to reconsider what his next career move would be. For him at age 50, it was sobering to think about getting back in the job market, but with no growth opportunities on his current path he also didn’t think he could keep doing the same role for another 15 years or more. He had mastered his role and couldn’t find the motivation to continue if an ownership component wasn’t in the cards.

If I go, there will be trouble, if I stay it will be double


Cue The Clash song and… the clash between holding onto the boring bird in the hand vs. seeking two better birds out there somewhere... You could stay with the same old familiar routine which pays well and where you have lots of friends and a decent match on the 401(k), etc., but where you could probably do the job in your sleep. Maybe that dream job exists where you could use your skills and interests in new and exciting ways, where you continue to grow and explore, but it seems kinda risky! How do you weigh the options? Are you ready to go back to making mistakes while you learn in order to be happier and more engaged? (Admittedly tough questions, BTW.)

When I left my corporate job more than a year ago, I had not been happy for quite a while. I had been in the same industry for 21 years and with the same company for 12 years. Though I had been very fortunate to have had 8 different jobs over those two decades, in my last role I found myself placed in a position for which I hadn’t applied nor was I particularly suited for it from an experience standpoint. I felt that I had allowed myself to be painted into a corner. Sometimes in the corporate world if you simply go with the flow, you’ll find yourself in place you hadn’t intended. I was there and I asked myself, “How did I get here? And what do I want to do about it?” After a couple years of trying to contort myself to fit what I thought was required in the role and being very unhappy doing it, I ended up having a frank conversation with my boss about what I thought was required in the role and how I wasn’t the right fit.

After the conversation, I was scared because I realized that by being truthful I could have been signing my own death warrant, but strangely enough, my heart sang. It felt so good to speak my truth. For a long time, I had been waking up on Monday mornings with a feeling of dread that had to be buried in order to do my job. Obviously, that was a not healthy situation.

Um, how did I get here?!?


I was recently telling my story to a woman at a professional networking event and she quoted lyrics from another legendary 1980’s song by the Talking Heads’ "Once in a Lifetime"****:

You may find yourself in a beautiful house

With a beautiful wife

You may ask yourself, well, how did I get here?...

You may tell yourself, this is not my beautiful house

You may tell yourself, this is not my beautiful wife

Letting the days go by

I got her meaning immediately – sometimes we just let the days go by unexamined and without intentional action, and then one day we find ourselves in a place we hadn’t expected. And the question is what do you do at that point?

An excellent question… and one that only you can answer for yourself. There’s risk in leaving, but there could actually be more risk in staying. Many professionals have gotten caught unaware by a restructuring or merger and seen their boring, but cushy job eliminated. Even when they weren’t happy with their jobs, they were shell-shocked by the prospect of being pushed out. And even worse, many people have retired from a job that they didn’t like and looked back wished that they had taken the chance long ago to follow their passion rather than take the route that everyone said was the smart, safe route.

If you are unhappy or bored with your current career, and you still have time left before retirement, why not explore what path you could take to feel vital everyday when you go to work?

Be brave and live the life you deserve


If this article has resonates with you, I encourage you to think about what you get out of your current job and how many of the boxes it ticks for you in terms of job satisfaction. Are you working only for a paycheck and health insurance? Or does your job satisfy you on a deeper level? It is possible to find a job doing what you love and you’re good at while also earning a decent income doing it.

If you would like to explore what could be the next step for you in a career that aligns with who you are, please reach out to me. I offer free, no-obligation discovery calls with people who want to see if working with a life and career coach is right for them.

My motto is Life is short – be you and be happy!

* The name and identifying details have been changed to maintain confidentiality.

**Link to The Clash’s video for “Should I stay or should I go”: https://www.youtube.com/watch?v=xMaE6toi4mk

***Link to Tour of William & Mary in happenin’ Williamsburg, VA: https://www.youtube.com/watch?v=UgoFivXVmn0

****Link to Talking Heads’ video for “Once in a Lifetime”: https://www.youtube.com/watch?v=5IsSpAOD6K8

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© 2018 Terry B. McDougall