Shed and Shine, Episode 99: Beyond the Exit—Finding Yourself After Selling Your Business

Hosts: Gino Wickman & Rob Dube
Release Date: January 28, 2026

Overview

This episode delves into the often unexpected emotional, psychological, and cultural effects of selling or exiting your business. Drawing from personal experience and client stories, Gino and Rob explore why financial windfalls don’t necessarily fill the void, the importance of proactive planning, how to care for your leadership team and employees, and how moments of transition can serve as powerful opportunities for personal growth.

Key Discussion Points & Insights

The Reality Behind Business Exits

• Identity Loss & Depression After the Sale (02:27, 06:33)
  • Selling a business goes much deeper than financial gain. Gino repeatedly emphasizes the mini-identity crisis that can follow:

    “They have sold their identity, and so their identity has been ripped from them. And they do go into a deep depression. And I’ve seen it now more times than I can count.” —Gino Wickman [02:27]

  • Rob echoes the same sense of emptiness:

    “I always had this idea ... we’d have this big celebration. ... It was so anti-climactic, I can’t even tell you.” —Rob Dube [04:33]

• Emptiness at the Top of the Mountain (06:33)
  • Even achieving the “big goal” seldom delivers the fulfillment expected:

    “You sold your business, you rang the bell, you achieved this thing ... It doesn’t fill the holes.” —Gino Wickman [00:00 and 06:33]

The Importance of "Selling Well"

• Plan Ahead With Purpose and Clarity (06:33, 12:16)
  • It's critical to sell on your terms and with intention:

    “You decide one of two things. Are you going to stay involved in the business or are you going to move on? ... You have to decide if you’re going to stay in that business. ... Or do you want to move on and ride off into the sunset?” —Gino Wickman [02:27]

  • List your reasons:

    “The first thing I did very early on was listed the 8 reasons why I’m selling.” —Gino Wickman [12:16]

  • Gino urges potential sellers to give themselves a five-year runway, even if that feels conservative, to ensure a thoughtful transition.

The Impact on the Team

• Communicating With Employees—Radical Transparency (08:00)
  • Gino chose openness, telling his team eight months before the sale.

    “Most experts, advisors, will tell you to never do this. I didn’t care, and I did it... I stood in front of all of our people ... and said, I decided to sell the company. I gave the eight reasons why.” —Gino Wickman [08:00]

  • This led to honest, healthy conversations and allowed leaders to choose their own path within the new structure.
• Considering Team Emotions (04:33, 08:00)
  • Rob describes neglecting this aspect, resulting in staff dismay:

    “We took virtually no consideration into that. ...When we shared with them the news, they were not happy.” —Rob Dube [04:33]

• Leadership Team Transparency (13:56)
  • Rob encourages leaders to be transparent about intentions, but Gino notes that, in practice, questions about selling rarely come from heads of departments – underlining the value and rarity of openness.
• Navigating Emotions & Opportunities (14:42)
  • Fear, uncertainty, and even resentment can be byproducts of a sale:

    “An exit can create uncertainty for people. It can create fear. ... You know, if you’re on the leadership team ... you might feel... the founder’s going to have a big exit and you’re going to have a small piece of it to no piece of it...” —Rob Dube [14:42]

Personal Transition: Finding True Self

• Moving Beyond Titles and Achievements (10:34)
  • Rob suggests using the transition to “go inside”, examining motivations and purpose outside of positions and accolades:

    “Your ego has been driving you for a long time, whether it’s titles, control, or achievement ... But you realize that all those things ... aren’t you; there’s something deeper.” —Rob Dube [10:34]

• 10-Year Thinking Vision (10:52)
  • Both hosts recommend drafting a long-term, post-exit vision to ground the next phase of life.
• Shedding the Old "Stuff" (10:34)
  • The “shed your shit” theme: Using the exit as an opportunity to strip away identity layers and rediscover your true self.

Resources & Practical Advice

• Recommended Reading & Episodes
  • Gino references his earlier “Selling Well” riff episode and strongly recommends Finish Big by Bo Burlingham as an essential guide for selling well. [06:33]
• Practical Steps for Sellers (12:16)
  • Make a list of reasons for selling to clarify your motivation
  • Define the profile of your ideal buyer and stay true to those criteria throughout the sale process
• For Life After Selling
  • Consider new avenues where your passion and experience can shine:

    “Some of our best EOS implementers are EOS clients who sold their business and are looking for their next passion and want to help other entrepreneurs do what they did.” —Gino Wickman [15:49]

Memorable Quotes & Moments

• On Selling for the “Wrong” Reasons:

  "You climbed this mountain for 5, 10, 20 years, and you realize that it doesn’t fill this void…” —Gino Wickman [06:33]

• On Team Transparency:

  “As soon as I started thinking that way, I let them know that.” —Gino Wickman [14:11]

• On Self-Reflection:

  “Take this as an opportunity ... to really spend some time going inside and maybe starting with your 10-year thinking vision.” —Rob Dube [10:34]

• On Emotional Fallout:

  “I knew right away. I was like, this is a disaster.” —Rob Dube, on working for the acquirer [04:33]

Important Segment Timestamps

• 00:00 — The emptiness after a sale: "It doesn’t fill the holes."
• 02:27 — Common entrepreneur depression post-sale and the importance of planning.
• 04:33 — Rob’s story of a failed transition and neglecting the team’s emotional needs.
• 06:33 — Transparency with employees: Gino’s unique approach to sharing the plan to sell.
• 08:00 — Supporting your leaders and crafting opportunities.
• 10:34 — “Going inside”: Reconnecting with your true self and vision after an exit.
• 12:16 — Gino’s top tips: List your reasons, create ideal buyer criteria.
• 13:56–14:42 — Leadership team transparency; acknowledging fears, resentment, and finding new opportunities.
• 15:49 — Life after sale: EOS implementer pathway as an example of post-exit freedom.

Final Takeaways

• Selling your business is as much an emotional and existential event as a financial one.
• Radical honesty and thoughtful communication with your team—which often means sharing more and sooner than most advisors recommend—can make a meaningful difference for all involved.
• Take time to reflect on your purpose, both before and after the sale; your sense of self should not ride on your business alone.
• Use transitions as an opportunity to “shed” outworn patterns and more fully express your true self.