Not everyone feels finished when their career ends, especially people who are wired to build.

This week, I’m joined by Randy Gage, an entrepreneur, author, and speaker who retired at 40 and realized he wasn’t done creating. Stepping away from work didn’t bring the sense of completion he expected, so he returned to building businesses, writing, and teaching. Not because he had to, but because he wasn’t done.

That instinct to question what comes next started much earlier. At 15, Randy was sitting in a jail cell, facing the consequences of a life that had gone off track. That moment forced him to rethink his direction, and he’s been asking those same questions about what comes next ever since.

​Click Here to Listen​

• How a stint in jail at 15 forced Randy to rethink his life

• Why early beliefs shape how we think about money, relationships, and health

• What Randy learned after retiring at 40 (and why he went back to work)

• The difference between a finite game and a life built around purpose

• How Randy defines prosperity beyond money

• What it means to age with intention and resilience

Resources:

​https://www.randygage.com​ ​Breakthrough U​ ​Randy on X​ ​Randy on LinkedIn​

About Randy:

Randy Gage is a bestselling author and thought leader in prosperity and personal development, helping entrepreneurs and creators rethink what’s possible in their lives and businesses. His work has influenced millions worldwide through his books, podcasts, and high-level trainings.

I know many of you are involved in various projects, ventures, and endeavors of all kinds. I invite you to send me an email about what you’re doing so I can share it with the rest of the community.

If you’re writing a book or an article, I want to share it.

If you’re taking a course or doing something you find interesting, I want to share it.

If you’re creating art, volunteering, or learning something new, I want to share it.

Please send me any relevant information. If you prefer not to have your full name included or have any restrictions, please let me know. I’ll put together a monthly newsletter highlighting what’s happening in the Chapter X community.

One of the many challenges we must face as we transition from career to life after is the idea of identity. After all, we’ve devoted decades to imagining, building, shaping, and fortifying identities that center around how we wish to be seen. We’ve assembled the trappings that support the safe citadel of who we are.

Whether you’ve been a CEO, an attorney, a doctor, or whatever title has been infused into who you “are,” that need no longer exists post-retirement. Yes, I know, it’s a shock to the system and a blatant attack on your sense of well-being and comfort.

This next chapter is all about reimagining and reshaping your life in the most wondrous ways. It might not feel that way, at least not at first. It’s vital that you give yourself permission to come to grips with the fact that with any change, and you’ve lived through plenty of them, it can feel uncomfortable, destabilizing, and yes, terrible.

Your “job” is to recognize that you’ve been here before. You’ve gone through all kinds of challenges and changes, and you’ve arrived here. You’re the male version of Dorothy, battling wicked witches, flying monkeys, and all sorts of unexpected troubles.

You’ve been Major John Reisman, battling twelve convicts who might shove a knife between your ribs at any moment. (I hope you get the reference, not to mention, Army officers who just plain hate you.)

It’s time to take what you’ve learned about handling adversity, change, and uncertainty and apply it to imagining what comes next.

Who are you without your previous title?
What’s possible?
What limitations are you placing on yourself?

For many men, leaving behind a career also means leaving behind a sense of identity. And much of our response to that change is shaped long before retirement ever enters the picture.

My guest today is Brian DesRoches, PhD. He’s a psychotherapist, coach, and author whose work focuses on how the brain responds to change. Brian helps people understand why self-doubt and disorientation often show up during major transitions.

We look at how long-standing emotional patterns can surface after work ends. Brian offers a way to see these reactions not as personal failures, but as learned responses that can finally be brought into the open.

Click Here to Listen

In this episode, we covered:

• Why identity loss can feel more unsettling than we expect

• How early emotional learning shapes our response to change

• What anxiety is often trying to protect us from

• Why so many men struggle without the structure of a professional role

• The emotional barriers to forming new connections

• How awareness can create room for something new

Resources:

www.briandesroches.com
Living a Trigger-free Life

About Brian:

Brian DesRoches, PhD, is a psychotherapist, coach, and consultant with over thirty years of experience integrating neuroscience into his work with clients. He is the author of Living a Trigger-Free Life, Reclaiming Yourself, and Your Boss Is Not Your Mother. His approach helps individuals make internal changes that lead to meaningful, lasting improvements in their lives.

So you’ll probably think I’m nuts, but that’s okay. I’m used to it.

I woke up around 4 a.m. this morning. At the center of my thoughts was the idea that we live our lives like oysters. No, there were no thoughts of lemon wedges, cocktail sauce, or mignonette.

I thought about how we build shells around ourselves.

I thought about how pearls are formed from irritation and discomfort, and the incredible beauty that can come from pain. Think transformation!

I thought about how vulnerable we are without our self-created protection.

I thought about how those shells, while useful in their own way, keep us apart.

I’m still pondering this, but I wanted to offer it to you as food for thought and consideration. How does this hit you?

Feel free to send me your thoughts and, of course, all the jokes and ribbing you desire.