Should I Stay or Should I Go? What No One Tells You About Leaving the Family Business

If you work in your family's business, there's something worth sitting with: one day, you won't. Whether you're the one leaving or watching someone else step away, a parent, a sibling, a cousin, it's going to happen. And the emotional weight of that exit is unlike anything you'll go through in any other job.

In this Part 2 conversation, Andrea sits back down with Adam Hatcher, family business consultant, former 13-year veteran of his own family's company, and author of The Chaos Proof Family Business. They get into the question that keeps successors up at night: should I stay or should I go? Adam shares the framework he uses with families to evaluate whether the business can still give you what you need, why family meetings were the only place where his own exit could unfold as a process instead of a crisis, and what it felt like to walk down the stairs of the family company for the last time, following the same steps his grandfather once walked.

Key takeaways from this episode:

If you work with your family, your exit is inevitable. Even if the company continues, one day you won't be there
The emotional impact of leaving a family business falls somewhere between a normal job loss and a family loss, and most people aren't prepared for that
Three questions to check in with yourself: Is there a future here that excites you? Can you do your job wholeheartedly? Are you being rewarded, recognized, and developed?
Family meetings, separate from executive meetings, are where the honest conversations about staying or going can happen safely
When you leave, leave. Don't hover. The people who stay need space to figure out who they are without you
Leaving is not the opposite of loyalty. Sometimes making space is the most loyal thing you can do

If you haven't listened to Part 1, start there. We'll link it below. Adam covers how he joined, how they scaled, and what it's like working across three generations.

Connect with Adam Hatcher:

Website: https://21clear.com

LinkedIn: https://www.linkedin.com/in/adamhatcher/

Adam’s Newsletter: https://21clear.substack.com/

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com

Instagram: https://www.instagram.com/yournextgenfriend/

YouTube: https://www.youtube.com/@yournextgenfriend

LinkedIn: https://www.linkedin.com/in/andreashaver/

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