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You’ve taken over a family business. Or you’re about to. Or you’ve technically already taken it over but still report to a parent who is “no longer involved in operations” except that they still approve every invoice. Congratulations. You’re now in charge of something with history, customers, a legal entity, possibly a factory. It exists. And it worked. For decades. Which is the problem. Because now you’re wondering if it still does. This is a conversation I’ve had roughly 41 times over the past two years, usually over coffee or in the kind of office with slightly too many binders. It always starts the same way:

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“I want to do something… but I’m not sure if I should change the business… or start something new.”

At first, I thought I was hearing different questions. Now I know they’re all just variations of the same one:

“Can I build something of my own without destroying what they built?”

Which, to be fair, is a tricky thing to do. But after working with multiple successors, I’ve come to see that almost everyone ends up going through the same cycle. It’s not a linear path where you neatly move from Step A to Step B to Glory. It’s more of a loop. A strategic orbit. A choose-your-own-mess. You start in uncertainty. You end in systems. And in the middle, you either modernize what you’ve got - or build something new. I call it the Successor Strategy Loop.

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Insight

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Step 1 - Start 

(A.k.a. The Next Chapter Sprint. A.k.a. “Please help, I have three business models and a PowerPoint with ideas.”) This phase is deceptively simple. You’re not trying to change the world. You’re just trying to answer three things:

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1. Where is the business actually at?
2. What do you want?
3. What’s the gap between those two things?

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Easy, right? In practice, this part involves realizing the P&L doesn’t tell the full story, the team isn’t aligned, and your personal ambition might involve more than “keep this running.” You might want to grow. Or specialize. Or digitize something beyond the scanner. And until you say that out loud, you’re stuck in strategy limbo. Which, yes, is a real place. This is also the phase where I used to act like a general innovation consultant. I’d run workshops, gather ideas, post sticky notes. It all looked very collaborative and hopeful - until someone asked, “So… are we actually doing anything?” That’s when I realized: strategy without decisions is just expensive therapy. So now, I go straight to the fork.

Step 2 - Choose Your Path

(Modernize vs. Rebuild. Also known as “Would you like to upgrade your existing engine, or build a rocket next door?”)

Let’s start with modernization. This is for successors who believe in the core, but also believe it’s, well, creaking a little. Maybe the offers are outdated. Maybe the sales process is powered by Outlook 2007 and phone calls. Maybe the most strategic thing the company has done in five years is switch accounting software. Modernization means tightening the ship: better offers, leaner processes, cleaner data, an actual CRM. You bring in a bit of startup thinking, but you don’t call it that, because people get nervous. Instead, you talk about “customer centricity” and “revenue enablement” and then sneak in some automation while no one’s looking. This path is usually best for smaller teams, tight-knit operations, and businesses that are still profitable - but tired. You’re not reinventing the wheel. Just rotating it.

Then there’s the rebuild path. This one’s louder. It’s for the successors who say: “I don’t want to fix the old thing - I want to build the next thing.” Sometimes that means spinning out a venture. Sometimes it means launching a new product line. Sometimes it means turning a warehouse into a SaaS platform. (Ask me how I know.) This path is chaotic. You’re pitching new ideas inside old structures. You’re hiring people with startup résumés into family-run hierarchies. You’re making decisions with market data instead of tradition. Occasionally, you’re explaining to your uncle why the new logo doesn’t have serifs. But when it works? It’s beautiful. Because now you’re building with leverage. You’re using legacy trust, existing customers, and operational muscle to launch something the market actually needs. And you’re not doing it alone - you’re just not doing it the old way either.

Step 3 - Scale 

(A.k.a. Systems, Offers, Growth. Or: “Why did no one tell me this was the hard part?”)

Whether you modernize or rebuild, eventually you arrive at this phase. You’ve made a choice. Something new is in motion. Now you need to make it sustainable. Which means you need:

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• A real offer (not just a vision slide)
• A working sales and marketing system (not just a great salesperson)
• Clear internal processes (that survive even when you’re on vacation)

This is where successors often quit. Because the exciting part was the idea. Not the SOP manual. Not the KPI dashboards. Not the “What’s our Q3 forecast” meeting on a Thursday at 10am. But this is the difference between momentum and maintenance. Between experiments and enterprises. Between “we tried something once” and “we built something that lasts.” In other words: this is where you stop looping. And start building. Every successor I’ve worked with goes through this loop. They just enter at different speeds. Some come in guns blazing - “We’re launching a new business and raising capital!” Others whisper - “I think we need a new website?” Either way, the structure is the same.

You go from uncertainty → decision → execution → scale. You orbit around legacy and ambition until they align. You mess up, adjust, and move again. It’s not chaos. It just feels like it when you can’t see the map. But once the loop is visible, it becomes a tool. A way to move faster. And a way to know where not to rush.

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Question

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Where are you in the loop?

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Opportunity

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