Am I the only one who feels like I should have life figured out by now?

Stuck. Unsure. Confused about what comes next. It can be easy to look around and assume everyone else has their life sorted — especially in midlife.

In this episode of The Checkpoint, Dex explores what happens when the identity you’ve spent decades building begins to change.

The kids grow up and need you less. Careers that once made sense might not anymore. You suddenly get some of your time back — but you may have forgotten what you actually wanted to do with it.

Dex talks about parenthood, work, identity, starting over and his own years of trying different ideas before The Checkpoint became what it is today.

Maybe figuring out what comes next isn’t about immediately finding the right answer.

Maybe it’s about trying things, changing your mind and accepting that plenty of other people are figuring it out too.

So if you’re feeling stuck, unsure or wondering what comes next, you’re definitely not the only one.

What if the job you planned to retire from doesn’t exist by the time you get there?

As Dex approaches 50, retirement is starting to feel a lot closer — but so is the impact of AI on the workplace.

In this episode of The Checkpoint, Dexter Eugenio explores what artificial intelligence and automation could mean for people in their 50s who assumed their current job might carry them through to retirement.

For many of us, the plan might be simple: work another 10 or 15 years, build up our savings and then retire.

But that plan assumes our jobs will still be there.

Dex talks about AI, white-collar jobs, career security and why reaching 50 might not be the time to start coasting. Instead, it could be the time to start thinking about what else you could do, what skills you could build and what your next stage of work might actually look like.

Because the question may no longer be:

“When can I retire?”

It might be:

“Will my job still exist when I’m ready to?”

Does change really get harder as we get older?

Or does life simply become more complicated?

In this episode of The Checkpoint, Dexter Eugenio explores why making a big change in your 40s and 50s can feel so different from when you were younger.

With kids, ageing parents, mortgages, careers and decades of identity behind us, there can suddenly be much more to consider.

But maybe change itself hasn’t become harder.

From career changes and starting again to shifting your identity and caring less about what other people think, Dex asks whether getting older makes change more difficult — or simply makes the decisions around it more complicated.

Because sometimes the hardest part of changing your life isn’t deciding what comes next.

It’s letting go of who you thought you were supposed to be.

What actually happens when you retire?

In this episode of The Checkpoint, Dex and Adele explore two very different ideas of retirement — one built around slowing down and relaxing, and another where work, purpose and contribution never really stop.

They talk about the transition from full-time work, the importance of staying mentally and socially active, volunteering, travel, friendships, identity, and what happens when a career that has shaped decades of your life suddenly disappears.

Is retirement really about stopping work — or is it simply the freedom to choose what you want to do next?

Episode 0 – The Beginning

Welcome to the pilot episode of The Checkpoint.

In this first episode, I share why I started this podcast, the journey that's led me here, and the questions I've been wrestling with as I approach the next stage of life. From running an IT business for nearly two decades to searching for more meaningful work, this is the story behind The Checkpoint and the community I'm hoping to build.

If you've ever found yourself asking, "What's next?"—whether it's your career, purpose, relationships or life in general—this podcast is for you.