The Checkpoint Podcast: Questions

Which part of your life have you ignored for too long?

Health. Work. Family. Relationships. Yourself. Sometimes keeping everything together can feel like trying to keep a row of spinning plates from crashing to the ground.

In this episode of The Checkpoint, Dex uses the idea of spinning plates to explore how different parts of life constantly compete for our time and attention.

Sometimes work is going well while health starts to wobble. Sometimes family needs more attention. And sometimes figuring yourself out requires so much energy that everything else temporarily slows down.

Dex also looks back at his own period of questioning his identity, work and direction in life, and how focusing heavily on that part of himself affected other areas along the way.

Maybe balance isn’t about keeping every plate spinning perfectly.

Maybe it’s about noticing which one is starting to wobble before it falls.

What happened to the person you thought you’d become?

Maybe you had a clear picture when you were younger. Or maybe, like Dex, you never really knew exactly who that person was supposed to be.

In this episode of The Checkpoint, Dex looks back at the unexpected path that took him from marketing to IT, business ownership and eventually towards the work he’s doing today.

He talks about success, failure, changing direction and how seemingly bad decisions or difficult experiences can lead to people, ideas and opportunities you never could have planned for.

The person you thought you’d become was never necessarily the finished version.

Maybe the better question isn’t, “What happened to that person?”

Maybe it’s, “Who are they evolving into next?”

What are you waiting for?

More time? More confidence? More people to show up? Or maybe just some proof that the thing you’re working towards is actually going to work?

In this episode of The Checkpoint, Dex asks himself what he’s waiting for as he tries to build The Checkpoint community.

The answer turns out to be a lot of things: people, feedback, time, results, confidence and even a little validation that he’s heading in the right direction.

But there’s an important difference between waiting and doing nothing.

Dex talks about getting comfortable in front of the camera, putting himself out there on social media, overcoming the fear of what other people might think and learning that courage can come from simply doing something repeatedly.

Maybe we’ll always be waiting for something.

The question is whether we’re still moving while we wait.

What do you want the next 20 years of your life to look like?

As Dex approaches 50, that question takes him all the way to 70 — and surprisingly, his answer isn’t about retirement.

In this episode of The Checkpoint, Dex talks about what he hopes the next stage of his life will become: continuing to help people, bringing them together, sharing experiences and creating a place where the questions we quietly ask ourselves can actually be discussed.

Because some of life's biggest questions don't have one correct answer.

Whether it’s changing careers, watching your kids build lives of their own, looking after ageing parents or simply wondering what comes next, sometimes hearing how someone else has handled it can help you find your own way forward.

For Dex, the next 20 years aren’t about having everything figured out.

They’re about continuing to show up, asking the questions and building a community where people can figure them out together.

What would make you excited to get out of bed again?

For Dex, the answer comes down to one word: opportunity.

In this episode of The Checkpoint, Dex talks about the balance between routine and curiosity — having familiar habits that keep life grounded while still waking up excited about what a new day might bring.

From journaling and gratitude to building new ideas, learning, failing and trying again, he explores why simply having the opportunity to create something or pursue an idea can be something worth getting excited about.

And after a bad day, sometimes going to sleep and starting again tomorrow can bring the clarity and fresh perspective you need.

Maybe getting excited about life again doesn’t require knowing exactly what comes next.

Maybe it starts with seeing tomorrow as another opportunity to find out.

What have you outgrown without even realising it?

For Dex, the answer might be the need for the latest, greatest and most expensive things.

In this episode of The Checkpoint, Dex talks about his changing relationship with material possessions — from expensive cars, watches and sneakers to discovering that something cheaper, older or second-hand can sometimes bring just as much happiness.

A cheaper car unexpectedly becomes more enjoyable than the expensive one it replaced. Used shoes can feel just as good as new ones. And owning something because you genuinely like it starts to matter more than owning it because of what other people might think.

It’s a conversation about materialism, gratitude, ego and how the things we value can quietly change as we get older.

Maybe growing doesn’t always mean wanting more.

Sometimes it means realising that what you already have is enough.

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?