What’s Next for Us?

A free conversation starter for the partner behind the entrepreneur.

10 Thoughtful Questions to Ask Your Spouse About Life After Business

You’ve supported the business.

You’ve held the family together during the long hours, the late nights, the “just one more year” promises.

And lately, you’ve started to wonder:

When will it be time to think about life after the business?

Not just for them. For both of you.

This free guide gives you 10 powerful questions to help open that conversation—gently, respectfully, and meaningfully.

Because the future shouldn’t be something you tiptoe around. It should be something you create—together.

Inside this Free Download, You’ll Find:

  • Questions that spark reflection without pressure

  • A framework to talk about dreams, fears, and what’s next

  • A subtle way to help your spouse consider planning their exit

  • A simple starting point for deeper, future-focused conversations

WHO THIS IS FOR:

  • Spouses of business owners ages 45–60

  • Partners who’ve carried the emotional and logistical weight of entrepreneurship

  • People wondering what the “next chapter” of life could look like as a couple

About The Founder’s Transition Lab

The Founder’s Transition Lab was created by Lisa Bosse and Chris Evans to solve a critical problem for business owners: the emotional and strategic uncertainty of planning a meaningful exit. Most exit planning services focus on financial, operational and tax planning—leaving founders to navigate identity, purpose, and next-chapter clarity on their own. The Founder’s Transition Lab is different. Participants get:

  • A curated mastermind with other seasoned Founder's on the same journey

  • Executive coaching grounded in Core Energy methodology

  • A proven framework to align your personal, financial, and business goals

Lisa and Chris help founders gain the clarity, confidence, and tools they need to exit on their terms—and build a future that reflects who they’ve become. Through powerful peer support, expert guidance, and a step-by-step process, The Founder’s Transition Lab helps you turn uncertainty into opportunity—and design your next chapter with intention.