Helping founders discover their next passion project.

“Who will I be?”

This is the burning question many founders face when considering stepping away from their life’s work. It’s not just about leaving the company; it’s about leaving behind a piece of their identity. “What will I do?” pops up next, if they’re willing to even encounter the question “Who will I be?” and not blow up.

As part of succession planning, advisors must dig into the identity losses that creep into family conversations. Then they must help founders feel secure about their next exciting stage of life. This, in large part, is about helping them envision a new life passion. They already have the skill sets to move on. In fact, the successful founder is uniquely prepared for the task. They just don’t realize that all they have done in their life has prepared them to leave their comfort zone and move into the unknown.

Embracing the Lessons from Range

I recently read David Epstein’s book, Range: Why Generalists Triumph in a Specialized World. In short, Epstein explores how generalists, those with diverse experiences, often find greater success than specialists. Specifically, their skill set is developed through:

  1. Diverse Experiences: Generalists often pursue diverse experiences and interests rather than following a single, narrowly defined career path. This variety exposes them to different problems and solutions.
  2. Cross-Disciplinary Learning: By engaging with multiple disciplines, generalists learn to apply concepts from one field to another, fostering innovative thinking and problem-solving.
  3. Adaptability and Flexibility: Their broad knowledge base makes generalists highly adaptable. They can pivot between different tasks and roles, making them resilient in the face of change.
  4. Analogical Thinking: Generalists excel in analogical thinking, which involves making connections between seemingly unrelated fields to solve problems. This skill is crucial for navigating complex and novel challenges.
  5. Long-Term Learning: Generalists tend to engage in lifelong learning, continually expanding their knowledge and skills. This ongoing education helps them stay relevant and innovative.

Epstein argues that this breadth of experience allows generalists to excel in complex, unpredictable environments, as they can integrate and apply diverse insights to new situations.

As I read the book, I began to make connections between the entrepreneurial journey (or a founder’s journey) and what Epstein describes as the “wicked world”—one filled with novel challenges that require creative problem-solving. When a founder creates a business, they encounter things never encountered before. Despite their uncertainties, despite their undeveloped skill set for the specific job to be done, and despite the quickly changing landscape, they adapt and move forward. That’s range.

Embracing the Entrepreneurial Spirit

For founders to find significance—and not feel like they’ve lost their identity—they must apply this range to new endeavors. Throughout their career, founders likely encountered things that they knew weren’t right but didn’t have the time or inclination to address. Now, they have both the time and the wisdom to tackle these issues head-on. There are things that they’ve seen in the course of their career that they know aren’t right. But for the fact they simply didn’t have the time or the inclination to make that other something right, they passed on it.

After succession, not only will they have the time, they already have the inclination. More importantly, they already have the range—or skill set that they developed throughout their career. This is the moment for founders to revisit those passion projects with the insight and experience they’ve accumulated.

Of course, there’s the fear factor. Can I really contribute in this area I know nothing about? But think about it: When founders started their business, how much did they really know about managing, financing, strategizing, or all the other skills necessary to run a complex organization? The answer usually is they did not know all of what would be required of them.

They had an idea and wanted to find out if it would work. It did.

Over the years, founders have developed critical problem-solving skills and resilience. These aren’t just business skills; they are life skills. They’ve spent the proverbial 10,000 hours and more developing a skill set that is not just about running a business but about navigating life’s complexities. From a reservoir of experience, they have learned to create analogies and make associations for the purpose of problem-solving. This experience and wisdom are invaluable. They are what make founders uniquely qualified to face this new challenge of redefining their identity.

The key is to help founders remember the excitement that each day presented to them. Remember how charged up they were. Those early days were filled with unknowns, challenges, and a sense of adventure. That spirit, that drive, is still within them. It’s about tapping back into that energy and applying it to this new phase of life.

The Importance of Emotional Understanding

One of the most critical aspects of this transition is understanding the founder’s emotions. It’s not just about the technicalities of stepping down or handing over the reins; it’s about how they feel during this process. Engaging in conversations about their feelings and future aspirations can help deescalate fears and provide clarity on their next steps. Trusted advisors and family members can talk to the founder about those days and what it was like starting out. Talking about the past can be therapeutic and enlightening. It reminds founders of their journey, their struggles, and their triumphs. This reflection can be a powerful tool in navigating their future.

As founders move forward, remember that this is not about replicating past successes but about creating new ones. They need to be reminded they have the tools, the experience, and the spirit to tackle this next chapter. It’s about being brave, embracing the unknown, and finding excitement in the possibilities ahead. The entrepreneurial spirit that got them to this point is the same spirit that will carry them forward.

Founders are not starting from scratch. They are starting from experience. Their journey is far from over, and the best is yet to come.

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