- Date: August 14, 2026
Emotional challenges of transitioning out of your business
- 6 min read

When someone asks me what I do for a living, I tell them I help business owners transition their businesses to the next generation with their family intact and their successor ready. Almost without fail, the next question is, “What exactly is a business transition?” It’s a fair question. And if you’re reading this, chances are you’ve been thinking about your own transition journey, even if you haven’t put words to it yet. Beyond Succession Planning A business transition is not a legal transaction or a financial plan. It’s

I was on a call with a business owner who had done everything right. He’d read “It’s a Journey,” worked through some of the exercises, thought deeply about his transition. He has a daughter working in the business and a strong non-family employee. Both could be part of his future plan. We were talking about my own story. Years ago, my team did a SWOT analysis and identified my lack of a transition plan as one of the biggest threats to the business. I didn’t have a successor in mind

I met Brecken Glenn through the Bailey Program for Family Enterprise, and within minutes I knew her story would resonate with so many next-gens navigating what’s next in their family business journey. Four and a half years into working at Affinity Partners—her family’s real estate development firm in Northern Colorado—Brecken is already asking the hard questions most people don’t ask until a decade in: Am I here because of my last name, or because I belong here? https://youtu.be/VNQZszrV3sw The Path She Didn’t Plan to Take Brecken grew up thinking she’d

I had a conversation with Paige Wiese recently that reminded me why some transitions fail despite perfect financials and flawless legal work. Paige is the founder of Tree Ring Digital, a Denver-based digital agency. Over her 16 years in the industry, she’s developed a framework for protecting digital assets during business transitions. “There’s value in your website. There’s value in your domain names. There’s value in your Google reviews and your social media profiles,” she told me. “But most owners don’t realize those are assets until they’re at the deal

“While the fictional Roy family on the hit TV series “Succession” and the real world NewsCorp empire might get most of the attention, the fact is that most businesses could benefit from paying closer attention to how they hand off a business from one generation to the next. Unfortunately, the statistics bear this out: The business graveyard is littered with unsuccessful generational handoffs. According to Score, 70% of businesses that are passed on to the next generation fail. That number increases to a staggering 88% when businesses are passed on

After 30 years in this work, there’s one statistic that still keeps me up at night. 60% of transitions are going to fail. When I share this number with business owners, the gut reaction is like, well, they didn’t lock down their will enough or they had a bad tax strategy. And so all the money went away and that’s just simply not true. That 60% of transitions failing is actually because the family couldn’t communicate. So it was communication breakdown, missed expectations, people not on the same page. And

What does “fair” look like when you’re buying the family business? I come back to this question often, because in family business succession, fairness isn’t just a spreadsheet. It’s an emotional equation with a constantly moving denominator: siblings, history, legacy, expectation. I recently had a conversation with Mitch Gambert, third-generation owner of Gambert Shirts in Newark, New Jersey, who just completed the full handoff from his parents. He said something that stopped me in my tracks: “There were decisions I didn’t love, but I made them so I could sit

Every business owner knows fear. It shows up differently for each person—sometimes as a tight grip on the financials, sometimes as “waiting for the right moment,” sometimes as silence where there could be conversation. In this week’s solo episode of The Business Transition Roadmap podcast, Elizabeth Ledoux explores how fear quietly stalls even the most well-intentioned family business succession plans—and what it takes to move through it. https://youtu.be/PJeFJrVqUtw Prefer to read? Here’s what Elizabeth covers in this episode. Fear Rarely Announces Itself Fear doesn’t always look like fear. It can

I’ve been working with wealthy families for over 30 years, and there’s one conversation that causes more anxiety than any other: telling your adult children about the wealth they’ll inherit.
Just this week, I spoke with a father—let’s call him Robert—who’s in his late sixties with four children in their late twenties and early thirties. He has roughly $300 million in family assets. His kids are thriving in their careers, building their own lives, finding their own way. And they know almost nothing about what’s coming.