The Checkpoint Podcast: Questions

Do the people closest to me actually know what I want next?

You might have a close family, supportive friends and people who know you better than anyone. But does that mean they know what you're working towards or who you're trying to become?

In this episode of The Checkpoint, Dex explores why he's kept some of his biggest plans and ambitions to himself, even from the people closest to him.

He talks about avoiding judgement, making decisions without needing approval and the challenges of pursuing something new when everyone has known you as the same person for years.

From running an IT business to developing Reboot Player One and building The Checkpoint community, Dex shares why he's preferred to figure things out privately before inviting others into the process.

But as he talks through the question, something interesting happens.

He begins to realise that keeping his plans private may have helped him get started, but sharing them could be an important part of moving forward.

Because sometimes telling people what you want isn't about asking for permission.

Maybe it's about finally being comfortable enough with your direction to let the people closest to you see where you're heading.

What are the signs that you're burnt out, not just tired?

Sometimes the warning signs aren't about feeling exhausted. They might show up as frustration, resentment, anger or simply reacting to things that normally wouldn't bother you.

In this episode of The Checkpoint, Dex shares a period in his life when, after 16 years of running his own business, he became so frustrated with his circumstances that he decided to give employment a try.

What followed was nine months of working for someone else, a change that ultimately helped him appreciate the freedom and opportunities he already had.

But looking back, Dex notices something interesting about that experience.

Despite feeling angry, stressed and frustrated, he also found himself with an unexpected amount of energy, determination and motivation to change his situation.

It raises an interesting question about how negative emotions can sometimes push us into taking action, even when we're approaching our limits.

Of course, burnout isn't something to deliberately chase, and Dex isn't even certain that what he experienced was burnout.

But maybe recognising when we're no longer behaving like ourselves is an important signal that something needs to change.

And sometimes, that realisation can become the beginning of a very different direction.

How do I find my purpose in life?

It's one of those big questions that can leave us searching for years. But what if finding your purpose isn't as complicated as we make it?

In this episode of The Checkpoint, Dex explores the idea that discovering your purpose might simply come down to trying different things.

Whether it's helping others, learning something new, revisiting an old interest or stepping outside your usual routine, sometimes you need to experience what doesn't work before you discover what does.

But Dex also challenges the idea that everyone needs one clearly defined purpose in life.

What if your purpose has nothing to do with helping others or making a difference in the world? What if it's simply about being happy, looking after yourself or enjoying the life you already have?

And what if you don't need to declare a purpose at all?

Maybe life is too broad, unpredictable and full of possibilities to reduce it to one single mission.

Maybe finding your purpose isn't about discovering the one thing you were meant to do.

Maybe it's about giving yourself permission to explore everything life has to offer, without needing to put a label on it.

What do happy people do differently every day?

Is happiness something that just happens, or can the little things we do each day make a difference?

In this episode of The Checkpoint, Dex shares some of the everyday habits that help him stay happy, even when life doesn't quite go according to plan.

From writing down three things he's grateful for each morning to staying connected with friends and family, Dex explores how small actions can help him appreciate what he already has and give him something positive to return to when things get difficult.

He also talks about the importance of looking inward, recognising when his own behaviour needs to change, being willing to apologise and learning to become someone he's happier being.

And then there's exercise, meditation and those moments when a good run can help clear his head and give him a different perspective on whatever's bothering him.

Because being happy doesn't mean every day is going to be a good one.

Maybe happiness isn't about avoiding the difficult moments.

Maybe it's about building habits that help you find your way back when they happen.

How do you actually reduce stress instead of just managing it?

Sometimes stress isn't just about having too much to do. It's about feeling like everything is happening at once and you've lost control of where your attention goes.

In this episode of The Checkpoint, Dex explores the different ways he deals with stress, from meditation and getting enough sleep to talking things through and confronting the problems he'd rather avoid.

He shares his own approach to meditation, which isn't always about clearing his mind. Sometimes it's about focusing on a single thought and giving himself enough space to think clearly without everything else competing for attention.

The discussion also explores the importance of understanding yourself, questioning whether certain worries deserve the energy you're giving them and how faith or spirituality can sometimes provide a little breathing room when things feel overwhelming.

But one of the more uncomfortable ideas is that sometimes the thing causing stress is the very thing we've been putting off.

Maybe reducing stress isn't always about finding better ways to cope with it.

Sometimes it's about finally facing what's causing it in the first place.

How do you stop comparing yourself to others?

The cars people drive, the houses they own, the clothes they wear and the money they make. It's easy to look at someone else's life and wonder why you haven't got what they have.

But does that comparison change as we get older?

In this episode of The Checkpoint, Dex talks about how his relationship with material possessions and other people's opinions has changed as he approaches 50.

From enjoying a relatively inexpensive car more than some of the expensive ones he's owned, to no longer caring whether his shoes are brand new, Dex explores how the things that once seemed important can gradually lose their appeal.

He also talks about gratitude, appreciating family, friends and health, and why recognising what you already have can make someone else's success feel a lot less important.

But comparison isn't always a bad thing. Sometimes a little jealousy can become motivation to work harder, try something different or pursue something you genuinely want.

Maybe we'll never completely stop comparing ourselves to others.

Maybe the real challenge is deciding which comparisons deserve our attention and which ones simply don't matter anymore.

Why do I worry about my health so much now?

As Dex approaches 50, he's becoming more aware that looking after his health isn't quite as straightforward as it used to be.

In this episode of The Checkpoint, Dex explores how getting older changes the way we think about exercise, recovery, diet and the physical limitations we might not have worried about in our 20s and 30s.

He talks about the temptation to keep up with our younger selves, the importance of staying active and a term he recently discovered: "health span", the number of years we spend living in good health rather than simply being alive.

But his concerns aren't just about getting older. They're also about being there for his kids, staying independent and having the physical ability to enjoy the next stage of life.

Because living longer doesn't necessarily mean enjoying those extra years.

Maybe worrying more about our health as we get older isn't such a bad thing.

Maybe it's a reminder to start looking after the future version of ourselves while we still can.

Why is it so much easier to get things done when you have no other choice?

Dex has noticed something about himself: desire can get him moving, but desperation seems to put him into an entirely different gear.

In this episode of The Checkpoint, Dex talks about struggling with motivation while building Reboot Player One and The Checkpoint, despite genuinely wanting both of them to succeed.

He explores why deadlines, consequences and having something to lose can create incredible focus, while having plenty of time and a comfortable safety net can sometimes make it surprisingly difficult to take action.

The problem is that deliberately creating a crisis isn’t exactly a sensible solution when you have a family, responsibilities and a life you don’t want to blow up just to become more productive.

So how do you create the urgency of desperation without actually needing your life to fall apart?

Maybe the drive is already there.

The challenge is figuring out how to access it before you absolutely have to.

Why is it so much easier to get things done when you have no other choice?

Dex has noticed something about himself: desire can get him moving, but desperation seems to put him into an entirely different gear.

In this episode of The Checkpoint, Dex talks about struggling with motivation while building Reboot Player One and The Checkpoint, despite genuinely wanting both of them to succeed.

He explores why deadlines, consequences and having something to lose can create incredible focus, while having plenty of time and a comfortable safety net can sometimes make it surprisingly difficult to take action.

The problem is that deliberately creating a crisis isn’t exactly a sensible solution when you have a family, responsibilities and a life you don’t want to blow up just to become more productive.

So how do you create the urgency of desperation without actually needing your life to fall apart?

Maybe the drive is already there.

The challenge is figuring out how to access it before you absolutely have to.

Why do I feel like I’m running out of time?

For Dex, that feeling really started when he became a parent and suddenly had a very visible reminder of just how quickly the years were passing.

In this episode of The Checkpoint, Dex explores how having kids changed his perception of time. Birthdays, school years, graduations and seemingly random memories become markers that make you stop and wonder where all those years actually went.

He also talks about putting things off until Monday, watching months disappear surprisingly quickly and how getting older brings even more reminders that time keeps moving, whether we’re paying attention to it or not.

But maybe “running out of time” isn’t quite the right way to describe it. None of us actually knows how much time we have left.

The strange part is simply realising how quickly the time we’ve already had seems to have disappeared.

Maybe the question isn’t how much time do I have left?

Maybe it’s what am I doing with the time that’s passing right now?