Episode 2 | Why Change Feels Harder After 50?

The Checkpoint Podcast: Questions · Sep 3, 2026 · 14m · transcript

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…