Should I Stay or Should I Go? A Question Every Owner & Leader Must Eventually Answer

In 1981, the English punk rock band The Clash wrote the song “Should I Stay or Should I Go,” which at one point made Rolling Stone’s 500 Greatest Songs of All Time. You have probably heard it in a few different commercials over the years too! While that song was originally about a guy’s relationship with a girl, it asks a question that every leader or business owner will eventually face.

For some organizations, like publicly held companies and nonprofit organizations, the question may be answered for you by a board of directors that has the authority to make such a decision. But for a privately held business, it gets a bit more complicated for the owner. Some owners stay because they feel obligated to care for their employees. Others may be uncertain regarding what they would do if they were no longer running the business. Others may still need or desire the income. And others struggle to give up control of their “baby,” the organization they built.

Eventually, every owner or leader will need to answer the question of staying or going. Over many years, our team of consultants has worked with business owners of small, medium, and large companies, nonprofits, and churches. Although many complex factors may affect the decision of “should I stay or should I go,” we have discovered that one or more of the following seven factors frequently come into play when leaders and owners are deciding if it is time to move on.

1. A critical life event.

A critical life event often serves as a trigger for owners or leaders to make the big decision of stepping down from their role. Take, for example, the case of Jonathan (not his real name, of course!). In his sixties, Jonathan received a non-terminal cancer diagnosis, discovered an additional health-related issue, and his wife had joint replacement surgery. These three major events hit at a stage of life when Jonathan did not need the income, so he decided to retire to reduce the demands in his life. Most of us will have at least one critical event in our lives that impacts us or someone close to us. These may include but are not limited to disability, divorce, disagreement, or a death. While a critical event does not always result in a career transition or sale, it sometimes does. And the pressure that comes from the event can also make it a risky time to sell a business or launch your succession since it is often done under pressure.

2. Stress and fatigue.

I knew the owner of a very successful business that had experienced significant growth. He had worked in the business since he was 14 years old, when his father was running it. He was now in his fifties, and frankly, after 40 years of working, leading, and owning, he was tired. He wanted a change. He was ready to step away from it, and he was confident that now was the time. Like freezing rain on a windshield, the stress of owning a business or leading an enterprise often builds over time until, all of a sudden, you are having trouble seeing what’s ahead, and the drive has gone from relaxing to exhausting. He had resiliently navigated the difficulties of leadership like cash flow, debt, customer challenges, and personnel issues for many years. But life changes with age, and he no longer had to do it. He had options, and one of those was to sell.

3. Boredom.

I was recently talking with someone who mentioned they worked at Disney’s Animal Kingdom. Who wouldn’t love that?! But they explained that even a job as exciting as working in the “most magical place in the world” can become routine and lose some of its excitement. Similarly, I once told a business owner I was coaching that someday she would wake up and say, “I am not having fun doing this anymore,” and when that happened, it might then be time to consider selling. This owner did an exceptional job running her business, but as the Bible says, there is a time and a season for everything, including when to hold on and when to let go. One day, she said to me, “I am not finding joy in this anymore.” And that served as the trigger to begin her successful exit.

4. Emerging challenges.

Successful leaders are used to conquering challenges. In fact, it was overcoming such challenges that energized them in the early stage of their leadership. But the wear and tear of dealing with constantly changing regulations, staffing transitions, employee conflict, and the ever-present challenges of the marketplace over many years can leave a residue of stress and fatigue. Not to mention navigating a pandemic. Owners sometimes see what is emerging, and it looks like a train is heading straight for them – a need for an infusion of cash for major equipment upgrades, a need to replace key staff who are retiring, family members in the business who do not get along, changes to the industry, growing impact from larger competitors, etc. Even when the business is healthy, future challenges may no longer match the owner’s appetite for complexity or risk and can serve as a trigger for an exit.

5. Best time for the valuation.

Several years ago, my aunt gave me a gold ring. It was quite nice, but I am not a jewelry-wearing kind of guy. So it sat in storage for years until I decided to sell it six years ago (when the value of gold was in the tank). If only I had held it until now, it would have been worth at least twice as much as I sold it for! This is true for businesses as well. There are good times to sell and less-than-ideal times to sell. If an owner wants or needs to get as much value as possible out of the business, they sometimes need to sell when the business is at its peak. Excellent contracted or recurring revenue. High growth. Modest to low debt. Exceptional profitability. Highly capable employees. A product or service that is likely to be in demand for a while. Some owners choose to sell because the best return on their investment is now, even if they would have preferred to wait a while longer. And for some, the decision isn’t just about cashing out; it’s about allowing what they have built to transition to its next logical phase in the best possible position for continued success.

6. You have the right leader or buyer.

My cousin once found a house on an awesome lake that he thought would be a nice location for his family. He is very successful, so he had the resources to knock on the door and make an offer to the owner that was too good to refuse. Then he tore the house down and built his amazing home. That homeowner may not have been thinking of selling, but when the right buyer came along with a stunning offer, it made it the right time to sell. In another case, the leader of an organization decided to step down because she had a great candidate for her job who was already working in the business and showed interest in advancing. As in both situations, the trigger for a transition can be a matter of timing – having a great successor or having a great offer. (However, business owners need to be aware that some offers may undervalue the business.) Unless the owner needs out quickly or they have a buyer that is a perfect fit at a fair price, we usually would encourage the business owner to run a competitive, professional sale process to help them get the best value for their business.

7. A greater passion and vision.

All of the above are common factors that can influence an owner’s decision to step out of their role. But there is one more factor that is a bit different than the others. It is when a leader or owner has experienced a growing passion or vision for something more fulfilling and meaningful to them. While there are owners who want to spend a lot more of their time golfing or traveling, others have a passion to serve and leave a legacy. Most of us have heard the name Viktor Frankl, the Austrian-born Holocaust survivor and psychiatrist famous for his transformational view of a meaningful life. He once said, “Life is never made unbearable by circumstances, but only by lack of meaning and purpose.” While some leaders and business owners found great purpose and passion in their business, they sometimes come to a point where it is no longer enough. They want to invest in something new and maybe even greater than what they are presently doing. It could be a philanthropic interest or a desire to encourage and support younger leaders by serving as a mentor. Or perhaps they have an aging parent or adult child who needs help due to health or other circumstances. A new or more compelling vision can serve as the trigger for making a career change in life.

Frequently, the decision to stay or go isn’t driven by a single problem or issue, but by a growing sense that the business simply no longer fits the current needs and desires of the owner.

If you would like assistance in determining when the right time is for you to transition from your leadership position or business or want help executing an exit, contact us. Our experienced team can help you create a plan for a successful transition when you are ready.

Jay Desko is the President & CEO of The Center Consulting Group and brings experience in the areas of organizational assessment, leadership coaching, decision-making, and strategic questioning. Jay’s degrees include an M.Ed. in Instructional Systems Design from Pennsylvania State University and a Ph.D. in Organizational Behavior and Leadership from The Union Institute.