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How Does One of Rolling Stone Magazine’s Top 500 Songs of All Time Speak to Entrepreneurs?

Sep 24, 2024 | Blog

In 1982 English rock band The Clash released their hit song Should I Stay or Should I Go?.

You’ve likely heard it, but like me may not have realized that it took ten years to reach peak popularity, and that was largely due to a Levi’s Jeans commercial. The song then topped the UK singles charts, and was ultimately listed, in 2004, in Rolling Stone magazine as one of the top 500 songs of all time. 

I’m not exactly sure what The Clash had in mind when they wrote the song, but the question Should I Stay or Should I Go? Is often in my mind as I think about many of the business owner clients that I encounter.

Although some businesses are built with an exit in mind, I would bet that most are not.

So this often becomes a clash of inner desires and emotions. On any given day, you could experience such high levels of stress that “going” might sound most inviting. Yet, on other days – hopefully most – you love what you’re doing, love the work you’re involved in, the people you work with, and of course, the clients or customers you serve.

One entrepreneur, Jan, built what had started as a small, home-based business, developed as an accompaniment to her husband’s profession. Through her focus, determination, and love of her work, her business grew to be, at one time, the largest of its kind in the country. 

As Jan approached the age at which many people dream of retiring, she was riding a wave of momentum with no end in sight. 

Business was good… life was good… and so, she kept moving forward.

The reality however is that, whether we like it or not, at some point we all must go (one way or another) and yes, that was another great song reference.

Jan still wasn’t ready to step away, but now in her 70s, she was finally ready to explore some options. 

We brought together a team of excellent professionals, which included her CPA. We helped her envision what was really most important to her. We then designed a clear succession plan that allowed her to continue to work on the few parts of her business that she really enjoyed (those aspects that utilized her genius).

The plan assured continuity so the business  would be able to continue fairly seamlessly without her.

Would you like to know what I found most interesting?

When Jan finally presented the plan to her key team members, her inner circle, many of them wept! This surprised her, and me – why were the people she had cared so much about, for so many years, crying over a continuity plan?

When asked, they were able to tell her that when it came to sleeping at night, many of them had been spending a lot of awake time wondering what would happen to the business, and their jobs, if one day suddenly she had been unable to carry the baton. 

So, an awesome by-product was that by developing a strategy and communicating it thoroughly, the inner uneasiness that had long dogged her team (unknown to her) was removed. Their occasional forays on to job boards – just in case – could end. They could focus all of their energy and efforts on continuing to grow the company, and their own careers with a long-term vision firmly in place. 

Jan now focuses all her time on the things she loves. She is also mentoring a team member with a similar skill set, so that, in the future when she wants to do less, or when “going” is now on the table, the business is well-prepared.

There is much more to this story, including how Jan was able to put a strategy in place which enabled her to keep far more of the money the business was generating away from the tax-man, and instead working for her and her family.

But for now… Should I Stay or Should I Go?

If you’re a business owner hearing this song in your head, let’s have a conversation. I’d love to hear a little about where you’re headed.

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