Finding Our Way: A Mastermind for Company Founders and Builders

Finding Our Way: A Mastermind for Company Founders and Builders Navigating Life After the Sale

Selling a business is not just a transaction. It’s not just a tactical and financial event. Selling a business is, for many owners, one of the most significant transitions they will ever experience.

Whether you are thinking about selling, actively preparing for a sale, in the middle of a transaction, or already living in the years that follow, this mastermind is designed to help navigate the deeper questions that often emerge when a major chapter of your life begins to change.

Inspired by Jim Collins’s book What to Make of a Life, participants will explore the concepts of cliffs, fog, fire, encodings, personal hedgehogs, self-knowledge, and purposeful living. This book is required reading or listening for the Finding Our Way mastermind.

Note: See the Finding Our Way Glossary

Here’s what Finding Our Way mastermind is NOT ABOUT.

It’s not about:

  • How to sell your business
  • How to retire
  • How to find purpose
  • How to create a life plan
  • How to discover your next career

It’s about discovery, awareness and self-knowledge. Questions are the pry bar.

For Those Thinking About Selling Their Company (Pre-Cliff)

  1. What will your life look like the day after you no longer own your company?
  2. What will your life look like the week, month and year after you’ve sold your company?
  3. If you didn’t sell, what would the next five years of your life actually feel like?
  4. What part of your work still energizes you—and what part drains you completely?
  5. Where is your energy now compared to high points during ownership?
  6. You are a business owner. Who are you once you sell the company?
  7. What are you afraid will happen if you sell?
  8. What are you afraid will happen if you don’t?
  9. Have you identified what you’re naturally built to do next? Or are you planning on winging it?
  10. Is this decision being driven by fatigue, opportunity, or something deeper?
  11. Are you preparing for what comes after—or only focusing on the exit?
  12. Who are you becoming as you consider this decision?

For Those In the Process of Selling (At the Cliff Edge)

  1. Are you clear on what you’re stepping into—or only what you’re stepping out of?
  2. How are you preparing for the identity shift that comes with this exit?
  3. What does success look like beyond the transaction?
  4. Are you making decisions for the deal—or for your life after the deal?
  5. What part of you is resisting this transition right now?
  6. Where are you already feeling the “fog” begin?
  7. Are you taking the time to think about life after, or are you just pushing to close?
  8. What would it mean to finish this chapter well?
  9. Are you holding onto anything you need to let go of?
  10. Who are you without the title you’ve carried for years?
  11. What are you avoiding thinking about right now?
  12. How will you know if this was the right decision a year from now?
  13. Are you reacting to pressure—or acting with clarity?
  14. What would it look like to cross this cliff intentionally?

For Those Who Have Sold Their Company (Post-Cliff / In the Fog)

  1. Now that you’ve sold—what question is your life asking you next?
  2. What part of your identity are you still holding onto?
  3. Where are you experiencing the most uncertainty right now?
  4. What has surprised you most about life after the sale?
  5. Are you trying to replace what you had—or discover what’s next?
  6. What are you doing right now that actually gives you energy?
  7. Where do you feel most lost—or most alive?
  8. What small step feels right, even if the big picture isn’t clear?
  9. What are you learning about yourself that you couldn’t see before?
  10. What responsibilities are you choosing now that everything has changed?
  11. Are you building something new—or just staying busy?
  12. What would a meaningful next chapter look like for you?
  13. Who are you becoming in this season of your life?
  14. What will you make of your life now once you sell?

Here’s what you can expect from this mastermind.

Expect to:

  • Explore the cliffs that have shaped your life, especially the sale of your company
  • Reflect on periods of fog and uncertainty in and around the cliffs
  • Examine the recurring patterns that may reveal your encodings
  • Consider what has consistently fueled your inner fire
  • Investigate the relationship between work, money, meaning, and responsibility
  • Engage with questions that help illuminate your next chapter

Invitation

Finding Our Way is a one-hour-per-week, five-week mastermind for company founders and builders who are standing on the brink of a major life transition, moving through one, or trying to make sense of life after one.

It is not a how-to program.

It is a guided exploration of self-knowledge, inspired by the major elements in Jim Collins’s book What to Make of a Life.

The Finding Our Way mastermind is an exploration of who you are, who you have been and who you may become. Together, we will examine the cliffs, fog, encodings, inner fire and personal hedgehogs that shape every life and consider what they reveal about the life you are making.

Please join us!

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