- Date: September 3, 2026
How Two Business Transitions Shaped the Second Edition of It’s A Journey
- 7 min read

Succession planning. Just saying those words can make business owners uncomfortable. Why? Because most people hear “succession planning” and immediately think you’re stepping away, handing over the keys, getting ready to retire. https://youtu.be/nozqaVVHfx0 But that belief is costing owners time, leverage, and peace of mind. Here’s the truth: succession planning does not mean you’re leaving. What it means is that you’re leading your team, your business, and your family forward. It’s about strengthening your business, protecting your options, and increasing your freedom. Not necessarily handing over the keys anytime soon.

I was meeting with a business owner last month who told me he’d been thinking about creating a succession plan for years. When I asked what had stopped him, he said something I hear often: “I’m not ready to leave yet, so why would I need a plan?” It’s a fair question. If you’re not planning to transition your business anytime soon, why invest time and energy in succession planning? The answer is simpler than you might think: succession planning isn’t about leaving. It’s about being prepared for whatever comes

What an interesting concept: thinking about building a transition strategy together. That’s what we do with this concept of Transition 3.0. You’re moving from doing it for them to doing it with them. There are a lot of benefits in doing it together, not to mention that you get to know your kids better, you get to know your family better, you get to spend time together, and you also get to transition knowledge and background and stories and experience. It’s just a wonderful opportunity to design and build a

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