When I first started my business in high school, I named it “Flaming Squirrel Design.” I was seventeen, designing logos and building websites. How does this tie into what I do now as a Transition Guide helping family businesses? Well… there are lots of valuable skills I learned that have come with me into my family’s limited partnership and my role as a successor in a private firm.
That’s the thing about succession journeys—they rarely follow a straight line. And whether you’re taking over your family’s business, stepping into leadership at a company where you’ve built your career, or joining an enterprise with the intention to lead it someday, there are universal truths about the successor experience that nobody really tells you about.
Identity: Who Am I, Really?
I speak with successors every week, and there’s one thing I’ve noticed: we all tend to share the highlight reel rather than the behind-the-scenes footage. We talk about our excitement for the future, our innovative ideas, and our respect for what’s been built. And while these positive aspects are real, they’re only part of the story.
What we rarely discuss openly is the feeling of being caught between honoring legacy and creating change, the frustration of waiting for real decision-making authority, and the doubt about whether we’ll ever truly be seen as more than “the owner’s kid” or “the next in line.”
For years, I questioned whether my path—graphic design freelancing in high school, working in advertising, then UX design at a large consulting firm, before eventually leaving to start my own business again—was too circuitous. Shouldn’t I have known exactly what I wanted from the beginning?
What I’ve discovered is that those “detours” weren’t detours at all. They were exactly the experiences I needed to bring a unique perspective to our my family enterprise and the Transition Strategists’ business. That outside experience gives you something invaluable: the ability to see the business through multiple lenses.
I’ve witnessed this with other successors too. Like Lisa, who took time to complete her MBA before stepping into her father’s company. Though this extended his desired timeline for retirement, the additional perspective she gained transformed their final year working together into one of their most productive and meaningful experiences.
The truth is, your journey to leadership doesn’t have to follow anyone else’s timeline or path. The distinctive perspective you bring is often what the business needs most, even when it doesn’t yet realize it.
Wealth: What Does This Mean For My Life?
When the business has been part of your life—whether as the backdrop to family dinners or as your eventual destination after gaining outside experience—questioning your place in it can feel like questioning your identity.
I’ve sat with successors who confessed, when no one else was listening, that they weren’t sure if they wanted the responsibility, the lifestyle, or the legacy they were inheriting. This doubt isn’t weakness—it’s a necessary part of making a conscious choice rather than simply following an expected path.
Ownership should never be someone else’s dream for you. It must be your dream for yourself. The successor who approaches leadership as a conscious choice rather than an obligation brings something powerful to the business: authentic commitment.
I think about Gordon, a successor with financial expertise who stepped into his mother’s engineering company. Despite initial doubts about whether his skills would translate to the technical business, his financial acumen proved to be exactly what the company needed for its next growth phase. Instead of trying to become an engineer overnight, he brought his unique perspective while surrounding himself with the technical expertise the company required.
Wealth in succession isn’t just about financial assets—it’s about the richness of perspective, the value of alternative experiences, and the capital of fresh thinking. Sometimes the most valuable thing you bring to the family enterprise is the very experience that, at first glance, seems unrelated.
Family Business: Am I Doing This Right?
The succession process unfolds like a dance between owner and successor. It begins with the owner demonstrating how they do what they do, while you observe and learn. Then comes that sometimes awkward middle period where both of you are attempting to lead simultaneously. There may be missteps and occasionally bruised toes as you figure out the rhythm together.
I’ve seen this play out numerous times. Take Ned and Adam—Ned grew concerned when Adam wasn’t arriving at the office until 9:00 am, while Ned had always been there by 7:00 am. Ned confronted Adam, questioning his dedication. What Ned didn’t realize was that Adam was actually starting work at 7:00 am—just not in the office. He was calling every project manager first thing in the morning to stay on top of projects.
This misunderstanding highlights how even well-intentioned successors and owners can struggle during this crucial transition phase. Communication breaks down, assumptions take hold, and what should be a collaborative effort becomes a source of tension.
Every successful transition requires ending mutual dependency. This means developing your own approaches to maintaining customer relationships and making financial decisions without constantly seeking approval. Janine, a retail business owner, initially believed she couldn’t transition her merchandising responsibilities because she couldn’t explain how she made those decisions. Only by observing herself in action did she recognize the patterns in her decision-making that could be taught to others.
Finding Your Community
One of the most powerful things a successor can experience is simply hearing, “Me too.”
There’s something deeply validating about connecting with people who understand what it means to grow up around a business, wrestle with legacy, or quietly question your next step.
That’s why I created Your Next Gen Friend—a space just for us. For the successors, the in-betweeners, and the quietly curious. It’s where we talk openly about identity, wealth, family business, and what it really means to lead on your own terms.
If you’re navigating this path, you don’t have to do it alone.
👉 Follow along on Instagram, YouTube, and LinkedIn for honest conversations, reflections, and tools you can actually use.
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Because being a successor isn’t about filling someone else’s shoes perfectly—it’s about walking forward in your own.
You belong here.
Andrea Carpenter is an entrepreneur, successor, and guide for next-generation leaders at The Transition Strategists. Drawing from her experience in both her own businesses and her family’s enterprise, she helps successors navigate the complex journey from “next in line” to confident leader.
