Episode Title: Episode #34 | I Lost My Job of 20 Years – What’s Next

Published: 6/4/2026

Episode Summary

In this personal and vulnerable solo episode of Current Thoughts, J shares something unexpected that recently happened in his life: after more than 20 years in the same line of work, he lost his job. At 53 years old, the experience forced him to confront difficult questions about financial security, career stability, retirement, and what’s next.

Rather than responding with panic, J explains why he feels cautiously optimistic about the future. Having spent the last two years learning and experimenting with artificial intelligence, he believes AI represents both one of the biggest opportunities and one of the biggest disruptions facing people today. He discusses why so many people remain behind the curve when it comes to AI, why that creates risk for workers across many industries, and how he plans to use this transition as an opportunity to build something of his own.

This episode is an honest conversation about uncertainty, reinvention, resilience, and why learning new skills may be one of the most important things we can do in a rapidly changing world.

Key Takeaways

Losing a job after decades of stability creates a unique set of emotional and financial challenges
Midlife career disruptions often force people to reevaluate their future and priorities
AI presents both significant opportunities and significant risks for today’s workforce
Most people have heard of AI but have not yet learned how to use it effectively
Learning AI today may become as important as learning computers and the internet in previous generations
Being proactive about technology is often better than waiting until change is forced upon you
Skills developed over a lifetime can often be transferred into entirely new opportunities
Teaching and helping others learn can become a valuable path during career transitions
Financial preparation and savings can reduce panic during unexpected life events
Reinvention is possible at any age when you’re willing to keep learning

Topics Covered

Losing a job after more than 20 years in the same profession
The emotional reality of career uncertainty at 53 years old
Questions about retirement, financial security, and healthcare
Why job loss feels different in midlife than it does earlier in life
How two years of learning AI changed J’s perspective on the future
Why many technical professionals still aren’t actively using AI
The opportunity gap between AI users and non-users
Plans to create beginner-friendly AI content and training
The growing role of AI in everyday life and work
Why businesses may increasingly adopt AI-driven solutions
The importance of staying proactive rather than reactive during periods of change
Turning a difficult setback into an opportunity for growth and reinvention

Connect With Us

Join the Conversation

Have you ever experienced an unexpected career setback or major life transition? How did you respond? Are you currently learning about AI, or does the rapid pace of technological change feel overwhelming?

Share your thoughts in the comments or send us a message. We’d love to hear where you are on your own journey and what questions you have about adapting to change in today’s world.

Thanks for listening to Current Thoughts. If this episode resonated with you, share it with someone who may be facing uncertainty or considering a new direction in life.

If you enjoyed this episode you may enjoy listening to episode 5 on Everyday AI: How it is Changing Our Lives or episode 32 Why People Over 40 Reinvent Their Lives (And What Finally Pushes Them).

Full Episode Transcript

Losing My Job at 53 and Facing an Uncertain Future

J: So welcome back to another episode of Current Thoughts.

J: I’m your host, Jay. If this is your first time here, welcome.

J: This is a podcast about helping you rethink your life, take back your time, and build freedom after 40.

J: And today’s episode is going to be a little bit different. It’s going to be raw.

J: Something personal happened in my life, and I’m going to open up and share it with you guys.

J: So something happened to me, and I kind of saw it coming.

J: I lost my job.

J: Now, I was an independent contractor, so basically they just terminated my contract. It’s something that I’ve been doing for 20 years.

J: And at 53 years old, it hits a little bit different than if you were, say, 25 or 35.

J: A lot of things go through your head. You start asking yourself things like, “Is anybody out there going to hire me in the job market? What does the job market even look like?” Because in 20 years, a lot of things have changed.

J: And at 53 years old, do I really want to put my financial stability in the hands of another employer?

J: So that’s a lot to sit with.

J: There are a lot of people in my situation. They might not be in their 50s yet. They may still be in their 40s or late 40s. But I have a feeling there might be a lot more coming as well.

J: So I’m not really panicking as much as most people would in my situation. And there’s a reason for that, and I’ll get to that in a moment.

The Financial and Emotional Reality of Job Loss

J: Don’t get me wrong. A lot of the normal things fester in my mind, such as, “So what are we going to do now?”

J: Because I do have a wife. We have a family. And I was the breadwinner.

J: Now, we have some savings, so we’re not under immediate pressure to find another revenue source.

J: That was one thing, obviously—the financial pressure—especially being about 10 years away from potential retirement.

J: Obviously, medical insurance and a lot of other things come into your mind.

J: Something else that made this particular termination hit a little harder for me is that this is all I’ve known for the past 20-plus years.

J: So I’m out of practice when it comes to putting together a basic resume and understanding what employers are actually looking for, if that’s the route I decide to go.

J: When you’ve been working at a job for 20 years—and I know that’s rare nowadays—you kind of learn the routines of that particular job, the ins and outs, and everything that comes along with it.

J: And now you don’t have that routine.

J: Now you don’t have that stability.

J: And so now you focus on finding the next thing, whatever that is.

Why I’m Not Panicking About the Future

J: So here’s the thing, though.

J: I’m ahead of the curve when it comes to AI because I’ve been learning AI for the past two-plus years and learning what it can do and how to use it.

J: And from my understanding, there’s a lot of people out there—just from talking to people—that really haven’t dipped their toe into the AI world.

J: They may have heard about it. They may have even tried it out once or twice and weren’t too impressed, maybe because of the way they were using it.

J: But either way, the vast majority of people are either ignoring AI or not understanding AI.

J: And I think that potentially could be a big opportunity and a big risk.

The Opportunity I See in AI Education

J: A big opportunity for someone like me and my situation because I can teach people how to use it.

J: I think a lot more people are going to need to learn AI and develop the skills to understand how it works and how they can best implement it in their lives.

J: That’s something I want to pursue.

J: While I was on my contracting job, I used to interact with a lot of IT professionals.

J: Because I was learning so much about AI, I would constantly ask them what they thought of it, whether they were using it, and how they were using it.

J: Of the IT people I talked to, 100% of them were not using it in their work.

J: Some of them said they had dabbled with it a little bit in their personal lives.

J: And I don’t know if that’s just because, as an IT person, you tend to be extremely busy, putting out a lot of fires, and maybe they just don’t have enough time in the day to learn AI.

J: So that was a big surprise to me when I didn’t see IT personnel using it.

J: Even my younger brother—he’s an IT person—and he’s just now started using it.

J: I’ve been pushing him for at least six months that he should be learning as much as he can about it because it’s going to make his job a lot simpler, and it might end up replacing his job at some point.

J: So he better start paying attention.

Most People Still Aren’t Using AI

J: But for the most part, most of the people in my life—my family and my friends—whenever I bring up AI and ask if they’ve heard about this or that, I get a lot of glazed-over looks.

J: And some of them, the ones that have heard of it, again, they’re not using it or they don’t understand it.

J: And so that’s kind of led me to an opportunity: I’m going to share what I’ve learned with AI.

My Plan for Creating AI Content

J: I’m probably going to take two different routes because, again, I’m ahead of the curve by two years.

J: I don’t want to start from the very beginning of what I learned and work my way up because there are new AI tools coming out daily.

J: It’s a lot to keep up with.

J: I’m going to have two tracks that I’m going to be making content about.

J: One route is going to be content for complete beginners to AI.

J: Then I’m going to have another route where I’m sharing what I am currently learning.

J: That’s going to be for people who have potentially been trying to keep up with AI already.

J: I think if we can learn how to use it properly, it’s going to help us in all aspects of our lives.

J: I might as well share my experience and let you guys benefit from it as well.

Teaching Technical Concepts to Non-Technical People

J: So here’s the thing, though. I’ve always been a technical person.

J: I’ve also had to train non-technical people on technical things.

J: So I think that’s going to translate well into this transition of me creating training videos and answering questions for those of you who are interested in learning about AI.

J: And maybe somewhere down the road, I will put together an organized course and either do an online course or an in-person course for anybody who wants that.

J: But that’s down the line.

Why Learning AI Matters Now

J: Right now, I just want to try to get as many people as I can up to speed on AI.

J: Because here’s the thing: whether you choose to use AI or not, choose to learn AI or not, AI is going to be a part of your life.

J: It was already a part of your life before ChatGPT, Claude, Gemini, or any of these other major AI tools came out.

J: You just didn’t know it.

J: If you’re on social media—Facebook, YouTube, Netflix, or any of those platforms—their algorithms use AI to suggest content to you.

J: It’s just going to become more and more a part of our lives.

J: So I think that’s something we definitely need to be proactive about instead of reactive when it comes to learning more about it and finding out how we can actually use it to our benefit.

Choosing to Build Something of My Own

J: So this isn’t going to be a long episode.

J: I just wanted to share something personal that happened to me and share my plan going forward.

J: I don’t plan on looking for another job.

J: I plan on actually creating something for myself.

J: So if this is something that you might be interested in learning, ask the questions you’re interested in.

J: I’ll do my best to answer those questions either in videos or in future podcast episodes.

Will AI Replace More Jobs?

J: And someday you may be in a position like me. Probably not, but I have a feeling that AI is going to cause a lot more people to lose their jobs.

J: Because if you think about it from a business standpoint, if you can hire an AI agent to do the job of a paralegal, a secretary, or any other administrative job that uses a computer to accomplish tasks, you don’t have to pay benefits.

J: You don’t have to pay unemployment.

J: You don’t have to pay a salary, an hourly wage, or overtime.

J: It makes a lot of sense if you think about it from that perspective.

Share Your AI Experience

J: I’m going to be putting out training material for AI.

J: If you’re interested in something like that and you’re interested in learning about it, I need some feedback from you guys.

J: I need you to let me know what it is you’re interested in and where you are on your AI learning journey.

J: Have you never used AI at all?

J: Have you used it a little bit?

J: Have you tried using ChatGPT, Gemini, or Claude? Those are the three major ones.

J: If so, what did you think?

J: Because a lot of times I’ve had that experience as well. I’ve had a couple of family members try ChatGPT, and they weren’t impressed.

J: There’s a reason for that, and I’ll get into it in one of my future videos.

Closing Thoughts

J: Like I said, I want to keep this short, so I’m going to go ahead and wrap it up.

J: I thank you guys for taking the time to listen to this.

J: This wasn’t easy for me to come out and explain everything that just happened about me losing my job.

J: It’s never something that you want to broadcast to the world once you lose your job.

J: Thank you guys for letting me be raw this episode, and I will catch you guys next time.

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Episode 34: I Lost My Job of 20 Years – What’s Next