Life is complicated. Every decision creates a ripple effect, and no meaningful decision is ever driven by a single factor. Few choices carry more weight for a business owner than the decision to buy or sell.
The decision to purchase often is made at a relatively young age, at a stage when there’s not much to lose. There is energy, optimism and a willingness to take risk.
The decision to sell, on the other hand, is typically made later in life – when the stakes feel higher and when the outcome may help define the next chapter, perhaps even the remainder, of one’s life. But no pressure.
The factors involved in this decision are too numerous – and too personal – for any outsider to fully define. That said, there are several broad categories worth considering. Whether preparing for a sale years down the road or facing the decision today, taking the time to reflect – ideally, well in advance – greatly increases the likelihood of making an informed choice.
Financial considerations
We might as well start here. Life requires resources and the ability to envision a future after a sale – one that provides both security and freedom of choice – is central to this decision.
Within that sits a critical subcategory – the value of the asset itself.
This is where foresight matters. Investing back into the business, building something durable and creating long-term value will impact what a future buyer is willing to pay. Simply put, stronger businesses command stronger valuations.
And finances do not stop at the doors of the business. In next month’s column, we will take a deeper look at diversification – ensuring that the entire financial future is not tied to a single asset and that flexibility and choice are preserved beyond the transaction itself.
Time, health, life outside business
Beyond finances, there is life.
It is worth asking some difficult but important questions. Will we still be able to do the things we enjoy 20 years from now? What about 15? What if something unexpected were to happen tomorrow?
I was fortunate to know a wonderful woman named Mildred who, alongside her husband, built a remarkable business. In caring for her husband’s health, she suffered a serious back injury. Despite having the financial means to travel and enjoy life, she no longer had the health to do so. Her advice was simple: Do it now.
Of course, that guidance has its limits. But it does raise an important consideration – time and health have value, which isn’t always visible on a balance sheet. When viewed through that lens, the decision to sell can look different.
Legacy, leadership, timing
Beyond personal considerations lies legacy.
This includes family – by blood or by choice – team members and the broader community. Is this a moment when the business can continue to positively impact those you care about? And what happens if that moment is missed?
Often, this conversation turns to the next generation of leadership.
Quite frankly, if a future leader is willing to wait quietly on the sidelines until age 60, they probably are not the right leader. A certain level of drive is essential to building and sustaining a successful business.
The right person may only be available for a limited window of time. You might be able to continue running and growing the business for another five years. But in doing so, is there a risk of losing that person? Or diminishing their opportunity to lead and build upon what’s been created?
Timing matters – not just for you but for the future of the business itself.
Importance of choice
You have likely heard many of these ideas before. Still, I would encourage you to pause – whether 20 years away from this decision or 20 minutes – and think through them carefully.
If further away, consider what decisions can be made today that will improve the options later – for yourself and those who depend on you.
If at the precipice of a sale, take the time to ask these questions honestly. Challenge the assumptions. In some cases, it may take an outside perspective.
Because in the end – whether it is three days, three years or three decades – you will want to look back and say: I made my own decision. I understood my options. And I am at peace with my choice.
As I have said before, one of the strongest correlations with happiness is a sense of choice.
And in a decision of this magnitude, the ability to look back with that sense of ownership may have a lasting impact on happiness for the rest of your life.
But again, no pressure.
Carey Berger is president of Business Service Resource Group.
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