Abby Donnelly is the founder of The Leadership and Legacy Group, an executive coach and board director specializing in business succession planning, exit strategy, and leadership transition. She’s the best-selling author of An Insider’s Guide to Succession and Exit and serves on multiple boards including First Bank (FBNC), ABCO Automation, and Cone Health.
When Abby and I sat down for our conversation on The Business Owner’s Journey, she shared not just what’s in her book, but what most owners miss when they start thinking about succession too late. These insights come directly from that conversation and my follow-up discussions with Abby, making this an insider’s look at how to prepare for the emotional and strategic realities of leaving your business well.
I asked Abby why she felt compelled to write this book for business owners. Her answer was simple: “Because owners spend 30 or 40 years building their business and almost no time preparing to leave it.”
Her goal is to make the process less about the transaction and more about the transition. Abby helps owners get clear on what matters most - values, culture, and purpose -so the business continues to reflect their legacy long after they step away.
At its core, An Insider’s Guide to Succession and Exit tackles one of the most under-acknowledged challenges in entrepreneurship: how to prepare for the next chapter of life after ownership. Abby’s approach reframes exit planning as identity planning. She reveals that the discomfort comes not from the sale itself, but from the sudden loss of purpose and belonging if you haven’t planned for what’s next.
“Most owners think they’re planning an exit, but they’re really designing a new life. The sooner they realize that, the better their outcomes.”
The “Portfolio Life Plan” had the biggest impact on me. It’s a practical framework for designing what comes after exit - balancing meaning, flexibility, and personal fulfillment. As Abby told me, “This isn’t about filling time; it’s about creating a life that’s compelling enough to move toward.”
That shift from avoidance to intention sets the tone for the rest of the book.
Abby said the biggest surprise was how many owners profoundly regret selling within the first year. Research suggests as many as 75%. What she found was that regret doesn’t come from the deal terms; it comes from lack of clarity about purpose and direction post-exit. That discovery reinforced her belief that the emotional side of transition needs as much structure as the financial side.
Abby sees many owners treat succession planning as a last-minute negotiation instead of a multi-year leadership development process. The biggest mistake? Thinking “my number” is the finish line.
As she puts it, “A fair deal is the baseline, not the goal. What really matters is who you trust to carry forward what you’ve built.”
Start by asking three simple questions:
Abby’s book lays out how to align those answers into an intentional succession plan that’s financially sound and emotionally grounded.
Abby’s book is the one I wish more owners would read before they start thinking about an exit. It’s not just about making the best deal, it’s about designing your future with purpose.
The idea of “portfolio life” hit home for me. After I sold my company, that question of “What am I going to do now?” was harder to answer than I expected. Abby’s approach gives structure to that question. Simple, not easy, but transformative.
If you’re within five years of a possible transition, or even just curious what life after ownership could look like, this is the guide you need.
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