INTRODUCTION
When you decide to sell your business, you prepare for financial discussions, due diligence, and negotiations. But what many owners don’t expect or aren’t fully ready for is the emotional toll the process can take.
In this article Keith Dee, President of Osage Advisors, talks about the very real stress, anxiety, and exhaustion that arise during a transaction. Known in the M&A world as “deal fatigue,” these emotions can derail even the most well-planned sale if not managed with care.
WHAT IS DEAL FATIGUE?
Deal fatigue isn’t just one emotion…it’s a combination of stress, doubt, exhaustion, and uncertainty that builds up over the course of a transaction. It often hits business owners hard because they’re managing two full-time responsibilities at once: running their company and selling it. This overlap can cause emotional burnout that spills over into both work and personal life.
And it’s not just your emotions to manage. Family members, business partners, or key employees may also be feeling the pressure, adding to the weight of decision-making and further complicating the process.
HOW TO DEAL WITH DEAL FATIGUE
One of the best ways to navigate deal fatigue is by maintaining open and transparent communication with your trusted advisors—especially your investment banker and your attorney.
- Lean on your deal team.
Your banker’s role is not just to get the best deal, but to guide you through the uncertainty and keep the process moving when it feels overwhelming. - Step in when needed.
If negotiations stall—especially over minor legal details—sometimes the best move is to take the discussion out of the lawyers’ hands and have a business-level conversation between buyer and seller. This shift can help both sides refocus on what really matters and often results in faster, more practical solutions.
STAYING FOCUSED ON THE FINISH LINE
In the example Keith shares, even after months of progress, small unresolved issues caused stress and doubt to creep back in. The key to getting past these moments was:
- Understanding what was worth fighting for—and what wasn’t.
- Trusting the advisors and legal team to find practical solutions.
- Remembering the bigger picture and staying focused on the end goal.
FINAL THOUGHTS
Selling your business isn’t just a financial decision—it’s an emotional journey. But with the right mindset and the right team by your side, you can get through the tough parts and feel confident when you reach the closing table.
As Keith says, “When you sign those papers, you should feel good about it.”
Certain Members of Osage Advisors are Registered Representatives of and conduct securities transactions through StillPoint Capital, LLC, Tampa, FL. Osage and StillPoint are not affiliated.
Osage Advisors provides a lot of guidance in the M&A market here on our blog and on our YouTube channel and Podcast.
