Selling a business in uncertain times: Why timing is about more than tariffs, oil prices and geopolitics

With trade disputes, fluctuating energy prices and geopolitical uncertainty dominating business headlines, many company owners are questioning whether now is the right time to sell their business. Economic volatility often creates the perception that buyers will retreat and valuations will fall, prompting some entrepreneurs to postpone exit plans.

However, according to mergers and acquisitions adviser Mark Herbick, founder and CEO of the firm Pursant, external events are rarely the primary factor in determining whether a business owner should pursue a sale. Instead, the decision hinges on a combination of market conditions, business performance and personal readiness.

Looking beyond the headlines

Business owners understandably pay close attention to macroeconomic trends. Tariffs can reshape supply chains, conflicts can disrupt markets and commodity price swings can affect profitability. Yet Herbick argues that these factors need to be placed in context.

“A lot of people think that because of the things going on right now — war, oil prices, tariffs — it’s a bad time to sell,” Herbick explains to Digital Journal. “But it’s not necessarily those things in and of themselves that make it a bad time. Determining the right time is more complex than that.”

This perspective reflects a common observation within the mergers and acquisitions (M&A) sector. While broader economic conditions influence transaction activity, successful deals frequently occur during periods of uncertainty. What often matters more is the specific condition of the business itself and the preparedness of the owner.

For middle-market companies especially, buyers frequently look beyond short-term economic fluctuations and focus on longer-term indicators such as growth potential, cash flow stability, market position and strategic fit.

Three factors that need to align

According to Herbick, there is an ideal scenario for maximizing the likelihood of a successful transaction. “The perfect time to sell is when three things line up,” he says. “The market is in good shape, your business is in good shape, and you personally are ready to exit.”

The first element is the state of the market. When capital is readily available and buyer demand is strong, sellers generally enjoy more competitive bidding and potentially higher valuations.

The second factor is the condition of the company itself. Buyers are naturally attracted to businesses that demonstrate growth, resilience and a clear strategy for the future.

The third factor is personal readiness. Even when financial and market conditions are favourable, an owner may not be psychologically prepared to leave the company they have spent years, or even decades, building.

Herbick notes that when all three conditions are present, owners are likely to achieve the best outcomes. When they are not, the most important consideration often becomes the owner’s own readiness to make a transition.

There is, however, an important exception: “If you’re miserable in your business, you should sell,” Herbick says. “Personal misery trumps everything else.”

Three questions owners should ask

For business leaders considering an exit, Herbick recommends three key questions.

• Is the business growing, stable or declining?

Growth remains the most attractive condition for a sale. “Growth is the perfect situation for selling,” Herbick observes. “Stable is less than perfect. Decline is not great.”

A company showing strong momentum typically attracts a wider range of buyers. Growth signals opportunity, while declining performance usually increases buyer concerns and reduces negotiating leverage.

This does not mean businesses experiencing temporary setbacks cannot be sold successfully. However, companies demonstrating consistent growth generally achieve stronger valuations and generate greater investor interest.

• What does the transaction market look like?

Owners should also assess whether conditions currently favor buyers or sellers.

Factors such as interest rates, private equity activity, lending availability and industry-specific demand can all influence transaction outcomes. As Herbick frames the question: “Am I selling my business in its current condition into an environment that is buyer- or seller-favorable or neutral?” Understanding this landscape helps owners set realistic expectations regarding valuation, deal structure and timing.

• How do you feel about running the business?

The third question may be the most revealing. “When I wake up in the morning, am I energized to run my business?” Herbick asks. “When I come home at night, am I excited to get away from it — or eager to think about the day and celebrate the victories?”

While financial advisers often focus on earnings multiples and transaction structures, emotional engagement represents a critical but frequently neglected variable. Owners who have lost enthusiasm for the business may find that operational performance suffers over time, potentially affecting value if a sale is delayed too long.

The challenge of life after an exit

One theme increasingly recognized by M&A professionals is that selling a company creates emotional challenges as well as financial opportunities. “Owners obsess over valuation and deal terms, but they underestimate the personal side of the equation,” Herbick says.

Many entrepreneurs derive a strong sense of identity from their business. The company becomes more than a source of income; it provides purpose, routine, social interaction and a sense of accomplishment. When that disappears, some former owners experience an unexpected loss of direction.

“The grass may seem greener on the other side of the fence, but it’s just as tough to mow,” Herbick remarks. To address this issue, Herbick encourages clients to evaluate the sources of meaning and purpose in their lives before pursuing a transaction. He uses a 15-question assessment designed to help owners determine whether their strongest sense of identity comes from the business itself or from other areas such as family, community involvement, philanthropy or personal interests.