Shows / The Checkpoint Podcast: Questions
The Checkpoint Podcast: Questions
Somewhere around your late 40s or 50s, the questions change.
Not "what's next on the to-do list?" but "what's next, period?"
Who am I now that the kids need me less? What happens when work stops being the whole story? Is this actually it — or is there another level to play?
The Checkpoint Podcast: Questions is where Dex Eugenio sits with the questions that show up in midlife — career changes, identity, relationships, health, money, purpose — the stuff nobody really prepares you for. Some…
Episodes
- The Checkpoint Podcast: Questions
Episode 38 | When was the last time you stopped and appreciated the life you're living?
When was the last time you stopped and appreciated the life you're living? Between work, family, raising children and keeping up with everyday…
- The Checkpoint Podcast: Questions
Episode 37 | Why Is It So Hard for Men to Ask for Help?
Why is it so hard to ask for help as we get older? As we get older, we're supposed to have things figured out. We've gained experience, built careers, raised…
- The Checkpoint Podcast: Questions
Episode 36 | Have You Mistaken Stability for Happiness?
Have I mistaken stability for happiness? Having a steady routine, knowing what to expect and feeling comfortable with how life is going can be reassuring. But…
- The Checkpoint Podcast: Questions
Episode 35 | Would you want to know the exact date you're going to die?
Would you want to know the exact date that you're going to die? Would knowing how much time you have left help you make better decisions, or would it take away…
- The Checkpoint Podcast: Questions
Episode 34 | Are You Still Growing or Just Getting Better at What You Already Know?
Am I still growing, or have I just become very good at what I already know? After years of doing the same things, gaining experience and becoming confident in…
- The Checkpoint Podcast: Questions
Episode 33 | When did you last change your mind about something important?
When did you last change your mind about something important? Sometimes changing your mind isn't the difficult part. It's admitting that you were wrong in the…
- The Checkpoint Podcast: Questions
Episode 31 | If you could bring one thing back from your 20s or 30s, what would it be?
If you could bring one thing back from your 20s or 30s, what would it be? The music, the cars, the fashion or simply the freedom of waking up on a weekend with…
- The Checkpoint Podcast: Questions
Episode 30 | Do the people closest to me actually know what I want next?
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…
- The Checkpoint Podcast: Questions
Episode 29 | What are the signs that you're burnt out, not just tired?
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…
- The Checkpoint Podcast: Questions
Episode 28 | How do I find my purpose in life?
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…
- The Checkpoint Podcast: Questions
Episode 27 | What do happy people do differently every day?
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…
- The Checkpoint Podcast: Questions
Episode 26 | How do you actually reduce stress instead of just managing it?
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…
- The Checkpoint Podcast: Questions
Episode 25 | How do you stop comparing yourself to others?
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…
- The Checkpoint Podcast: Questions
Episode 24 | Why do we start worrying about our health more as we get older?
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…
- The Checkpoint Podcast: Questions
Episode 23 | Why Is It Easier to Give Advice Than Take Your Own?
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…
- The Checkpoint Podcast: Questions
Episode 22 | Why Do I Only Get Things Done Under Pressure?
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…
- The Checkpoint Podcast: Questions
Episode 21 | Why do I feel like I’m running out of time?
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…
- The Checkpoint Podcast: Questions
Episode 20 | Am I chasing the wrong things?
Am I chasing the wrong things? As Dex approaches 50, he feels pretty confident about the big thing he’s chasing: helping people, building a community, sharing…
- The Checkpoint Podcast: Questions
Episode 19 | Are You Actually Happy?
Am I happy? It sounds like a simple question, but happiness isn’t necessarily about every part of your life going perfectly at the same time. In this episode…
- The Checkpoint Podcast: Questions
Episode 18 | Will You Be Healthy Enough to Enjoy Retirement?
What if living longer isn’t the number we should be paying attention to? Dex recently came across the term “health span”, and it completely changed the way he…
- The Checkpoint Podcast: Questions
Episode 17 | What have you learnt that you wish you’d known at 30?
What have you learnt that you wish you’d known at 30? For Mish, getting older has revealed something she didn’t fully realise when she was younger: she’s more…
- The Checkpoint Podcast: Questions
Episode 16 | What have you outgrown without even realising it?
What have you outgrown without even realising it? For Dex, it might be the need to always have the latest, greatest and most expensive things. In this episode…
- The Checkpoint Podcast: Questions
Episode 15 | What do you want people to remember about you?
What do you want people to remember about you? Your career? Your achievements? The things you owned? Or simply how people felt when they were around you? In…
- The Checkpoint Podcast: Questions
Episode 14 | What actually happens when you retire?
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…
- The Checkpoint Podcast: Questions
Episode 13 | Have You Become Too Comfortable?
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…
- The Checkpoint Podcast: Questions
Episode 12 | What If The Advice You're Following is Wrong?
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 Podcast: Questions
Episode 11 | How To Slow Down When your Mind Never Stops?
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…
- The Checkpoint Podcast: Questions
Episode 10 | Which Plate Are You About To Drop?
Which part of your life have you ignored for too long? Health. Work. Family. Relationships. Yourself. Sometimes keeping everything together can feel like…
- The Checkpoint Podcast: Questions
Episode 9 | What Happen To The Person I Thought I'd Become?
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…
- The Checkpoint Podcast: Questions
Episode 8 | What's Stopping You?
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…
- The Checkpoint Podcast: Questions
Episode 7 | What Do You Want the Next 20 Years of Your Life to Look Like?
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…
- The Checkpoint Podcast: Questions
Episode 6 | How to Get Excited About Life Again?
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…
- The Checkpoint Podcast: Questions
Episode 5 | Does Buying More Actually Make You Happier?
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 Podcast: Questions
Episode 4 | Why So Many People Feel Lost After 50
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…
- The Checkpoint Podcast: Questions
Episode 3 | Will AI Take Your Job Before You Retire?
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…
- The Checkpoint Podcast: Questions
Episode 2 | Why Change Feels Harder After 50?
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…
- The Checkpoint Podcast: Questions
Episode 1: What Happens When You Retire?
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…
- The Checkpoint Podcast: Questions
Episode 0 - The Beginning
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…