How Leaders Can Deal With The Grief That Comes After Selling A Company

Selling a company is often celebrated as a hallmark of entrepreneurial success, yet the emotional complexities accompanying such a transition are seldom discussed. Beyond the financial implications, many founders experience a profound sense of grief when parting with an enterprise they’ve built from the ground up. In 2023, the small business acquisition market remained relatively stable, with 9,093 businesses sold in the United States, a slight increase from 9,054 in 2022. The total value of these deals rose to $6.5 billion from $6.3 billion.

Although these transactions are common, the emotional toll they take is rarely discussed. They often blindside entrepreneurs with unexpected feelings of loss, grief and a profound sense of identity displacement. Kelly Bayett, cofounder of the audio post-production company Barking Owl, shares her experience selling the business and transitioning to her new venture, Love Song, with cofounder Daniel Wolfe.

“Nobody talks about the mourning part,” the cofounder shares during a phone interview. “Everybody thinks selling a company is the dream, but there’s this sadness of realizing it’s no longer yours. It’s like, ‘I built this thing, and now it’s gone.’”

The Grief Of Letting Go As A Founder

For Bayett, Barking Owl wasn’t just a business—it was her “baby,” a creation built on creativity and collaboration. The decision to sell was not taken lightly. After years of success, including accolades and a tightly knit team culture, she realized that the offer to sell the company aligned with both professional and personal circumstances.

However, selling a business doesn’t just end with signing the papers. As Bayett explains, the emotional aftermath is complex. The transition was particularly challenging when the new leadership introduced changes that altered Barking Owl’s culture. Kelly likened the process to sending a child off to college: “You’re still in their corner, but they’re on their own now.” Despite her efforts to stay connected with the team, she felt the sting of separation, particularly when realizing she no longer had influence over the company’s future.

Acceptance And Moving Forward

Acknowledging and processing grief was a critical step. The cofounder experienced moments of profound sadness, from missing daily interactions with her team to feeling replaced. Yet, she came to understand that loss often accompanies growth. “You have to lose something to gain something,” she reflects.

This perspective allowed Kelly to shift her focus to her new venture, Love Song, a commercial production company she cofounded during her transition. Love Song emerged as a side project but quickly gained traction, becoming a thriving business. Bayett poured her energy into creating a company culture at Love Song that mirrored the values she cherished at Barking Owl: mentorship, community and love.

Building the new company gave her a new sense of professional purpose. “I see what I can do here,” she explains. “I’m looking at what the culture of Love Song is, and how can I make it culturally relevant, filled with love and focused on mentorship?”

It’s Okay to Feel Sad

One of Bayett’s key takeaways for other entrepreneurs is allowing space for emotions during transitions. “It’s okay to mourn it,” she advises. While the financial and professional benefits of selling were undeniable, she emphasizes that such decisions also require emotional alignment.

The cofounder stresses the need for entrepreneurs to own their decisions fully. “You’re constantly torn by the decision you’ve made,” she admits, “but ultimately, the key is to focus on why you made the choice and what it allows you to achieve.”

Love Song: Building A New Legacy

At Love Song, Bayett has embraced her role as a leader once again, albeit with a fresh perspective. The company has already garnered acclaim, producing commercials for major brands like Adidas, Vans and Apple. Love Song’s unique model prioritizes mentorship, pairing experienced directors with emerging talent to create a supportive and innovative environment.

This approach has allowed Bayett to channel her passion for fostering creativity and community into a new arena. Her experiences at Barking Owl inform her leadership style, but she’s also grown in ways she didn’t anticipate. Detachment from her first company has given her a broader perspective.

Lessons For Entrepreneurs

Bayett’s journey offers valuable insights for entrepreneurs contemplating the sale of their businesses:

• Honor your emotions—Grieving the loss of something you’ve built is natural. Acknowledge your feelings and give yourself time to process them.
• Focus on the future—Letting go of the past opens new opportunities. Use your experience to shape what comes next.
• Stay connected to your values: Whether in your old business or a new venture, maintaining your core values ensures continuity in your leadership and vision.
• Own your decision: Selling a business is a major life choice. Embrace it fully, and ensure the decision aligns with both your professional goals and personal priorities.

Selling a business you built from scratch is more than a financial transaction—it’s an emotional and professional milestone. By acknowledging the complexities of such transitions, entrepreneurs can move forward with clarity and resilience.

“It’s okay to be emotional about it,” Bayett concludes. “Mourn it, but don’t lose sight of what you can build next.”