The 5 Biggest Money Regrets of All TimeThe 5 Biggest Money Regrets of All Time
Livin the DREAM with Matt Scoletti
Matt Scoletti outlines the five money decisions people most often regret and shares real stories that bring each one to life. The conversation aims to spark awareness so you can make more thoughtful choices with your money now.
10:10•4 Aug 2026
The 5 Money Regrets That Haunt People Later in Life
Episode Overview
- Start saving as early as possible, even small amounts, to avoid long-term regret.
- Avoid high-interest "devil debt" like credit cards, as it harms both finances and relationships.
- Be honest about spending on wants and unused items that could have grown as investments.
- Learn what to do with the money you earn through books, podcasts and other educational resources.
- Seek advice sooner rather than later, and be selective about who you listen to on money matters.
“"If I just would have started saving… not even saving a lot, just started."”
What are the common struggles and victories in addiction recovery? Here, the focus shifts to one area that quietly shapes stress, relationships and long-term wellbeing: money. Matt Scoletti, a former alcoholic turned health coach and motivational speaker, breaks down what he calls the top five money regrets people carry later in life. You’ll hear Matt share real conversations that back up each regret.
A man in his 60s tells him, "If I just would have started saving… not even saving a lot, just started," highlighting how "not saving sooner" tops the list. Another couple’s story shows how carrying too much debt doesn’t just hit your bank account – it weighs on marriages and mental health.
Matt talks about "devil debt" like high-interest credit cards, the emotional sting of closets full of unworn clothes, and the frustration of working decades without learning what to do with the money earned. He’s blunt but upbeat, often shocked that people can work "40, 50, 60 hours a week" and never pick up a simple book or podcast to learn the basics. A big part of the conversation is about seeking better advice.
Matt jokes about avoiding the "broke uncle" and "broke friend" as your financial mentors, pointing instead to books, podcasts and videos as easy starting points. His energy is high, and he keeps things practical, repeatedly stressing small steps, habits and curiosity over guilt or shame. For anyone in recovery who’s now trying to rebuild their life, this episode offers a straightforward look at how money choices can turn into regrets – and how you can start sidestepping them today.
It asks you to think honestly: are you building a future you’ll actually want to live in?
Do you want to link to this podcast?
Get the buttons here!
More From This Show
The latest episodes from the same podcast.