Back in the Good Old Days

by | Nov 25, 2025

Changing jobs in your 50s and 60s has unique challenges younger generations likely don’t face. Going into a job interview, one normally prepares for meeting to impress your potential employer on your accomplishments, skills and presentation etiquette (manners, grooming, professional attire, etc.)

We talk about the projects we managed, the businesses we built, the teams we led and how we could do that again in a new organization. Our experience that took decades to build can be the hiring organization’s bargain of the century! We’re plug and play, right?

Imagine walking into an interview and learning your thirty-something interviewer recognized your last name, not because of you, but because your Mother was their THIRD-GRADE TEACHER! Yep, it happened.

According to recent reporting, millennials have officially become the largest group of managers in the U.S. workforce. For those keeping score, millennials are defined as people born between 1981 and 1996.

So yes, our decades of experience are being reviewed by someone born well-after you graduated. It is both humbling and hilarious.

For those of us who spent time raising children, we developed skills in people management, time-management, crisis management both at home and work. Falling on our face and getting back up to fight another day is what we had to do. There was no Google, Wikipedia or ChatGPT to help us figure it out.

What some may consider our weakness (age, for example) is actually one of our most powerful and unique strengths. The younger manager interviewing you is not your obstacle. Our mindset is.

That younger manager could be your greatest collaborator, someone you can mentor, and learn from.

Fresh, new thinking can come from both older and younger people. Sometimes the synergy of experience, technical acumen, and understanding the world through their eyes makes us unstoppable.

At The Comeback Cast, we will dig into this topic and more.

  • How to walk into an interview with a much younger potential boss

  • How to summarize decades of experience without sounding like a history lesson

  • How to frame our value not only by your experience, but by our attitude and work ethic

  • How people our age are turning those moments of awkwardness into opportunities for connection, humor and reinvention

Maybe we can teach these whippersnappers something they can leverage when they become our age. We can teach them that our later years can be a wonderful time to launch our second act, learn a new skill, stay relevant and remain vibrant. They can then do the same for the generations that follow.

Our Comeback Cast Podcast launches in late November. We will trade stories about interviews, reinventions, and rediscovering our purpose.