Do you stop working completely, slowly wind things down, or simply find something else that gives you a reason to get up in the morning?

In this episode of The Checkpoint, Dex and Adele explore two very different ideas of retirement.

For Adele, retirement means relaxing, travelling, spending time with family and eventually leaving traditional work behind. For Dex, the idea of completely stopping is much harder to imagine.

Their discussion explores how work, identity, purpose, friendships and contribution can all change as we get older, and why retirement might look very different depending on whether work is something you have to do or something you genuinely enjoy doing.

They also talk about volunteering, staying socially connected and what happens when the routines and relationships built around decades of work suddenly disappear.

Maybe retirement isn’t simply about whether you work or don’t work.

Maybe it’s about finally having the freedom to decide what you want your days to look like.

Have you become too comfortable?

Sometimes having stability can be the very thing that slows down the change you say you want.

In this episode of The Checkpoint, Dex looks at his own journey building The Checkpoint and Reboot Player One and asks why something he cares so much about has taken years to develop.

His answer? Maybe life has been comfortable enough that there’s never been a real need to move faster.

Dex explores the difference between dedication and desperation, and why losing your safety net can suddenly make opportunities, decisions and uncomfortable actions seem much easier.

But deliberately creating a crisis isn’t the answer either.

So how do you create the urgency to pursue something that matters when your current life is actually pretty comfortable?

Maybe the challenge isn’t escaping your comfort zone.

Maybe it’s finding a reason to move before life forces you to.

What if the advice you’re following is wrong for you?

Sometimes the answer isn’t trying harder. It might be trying the complete opposite.

In this episode of The Checkpoint, Dex explores his idea that life is often Yin and Yang — and how experimenting with the opposite approach has helped him discover what actually works for him.

From running and exercise to productivity, eating habits, mornings, creativity and even the way he communicates, Dex shares examples of conventional advice that worked for others but didn’t necessarily work for him.

Instead of assuming the advice was right and he was doing something wrong, he started asking a different question: what happens if I try the opposite?

Because advice can be useful, but it isn’t universal.

Sometimes when something stops working, the answer might be waiting at the other end of the spectrum.

What does slowing down actually look like when your mind never seems to stop?

For Dex, slowing down isn’t necessarily about doing less. It might simply mean doing one thing at a time.

In this episode of The Checkpoint, Dex talks about the way he’s spent years jumping between tasks, projects, problems and ideas, often moving several things forward at once rather than finishing one before starting another.

It’s a way of working that has served him well, but he’s also becoming more aware of the cost: distractions, lost focus and those moments when you return to something and can’t quite remember where you left off.

So what happens when someone who thrives on constant movement tries to slow down?

Maybe slowing down doesn’t mean stopping.

Maybe it means giving one thing your full attention before moving on to the next.

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.