Episode 16 | What have you outgrown without even realising it?

The Checkpoint Podcast: Questions · Sep 28, 2026 · 12m · transcript

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 of The Checkpoint, Dex talks about how his relationship with material possessions has changed over time, from cars, watches and sneakers to the simple question of whether spending ten times more actually makes you ten times happier.

A cheaper car unexpectedly became something he enjoyed just as much, if not more, especially because working on it created experiences with his dad and son. Buying used stopped feeling like a compromise. And…