The Mindset of the Uncomfortable vs. the Comfortable Investor

By Djomas @ Adobe Stock

All the uncomfortable investor ever dreamed about was being comfortable. You know, being able to buy a fancy car and a second home. To be the big dog around town. To be able to prove to the world that he was worth something and not to be messed with.

All went well during the market melt-up, where anything he threw money at went up, and it made him happy, but he was never really happy or satisfied.

Then one day, he bet the ranch and leveraged up on a “sure thing” that turned out to be far from a sure thing. He lost more money than he could ever afford to lose.

Now, he’s blaming something or other for his failure and screams inside his head at the unfairness of it all.

This is the plight of the uncomfortable investor, always digging up what appears to be the next big thing, feeling like he discovered the golden ring, only to realize that he was a pawn in the game.

Now then, the comfortable investor doesn’t think much about the game. In fact, he’s happy doing his work, having dinner with his family, and doing it all over again the next day.

He saves but doesn’t view saving as an inconvenience at all. He’s OK deferring some more happiness into his retirement years, when he will continue to pursue happiness. He’s figured out the world and is fine with not sharing his secret way to happiness.

He’s not trying to “beat” anyone. His secret is that he is content. He doesn’t even want to beat the other guy. He doesn’t think or dwell on the other guy. He understands there’s plenty of wealth to go around for the successful.

This is the mindset of the comfortable investor.

Action Line: Your Survival Guy seeks out the comfortable investor and knows immediately who you are when we speak about your path, a path that the uncomfortable will never understand. Let’s talk. Email me at ejsmith@yoursurvivalguy.com.

Previous articleSales Taxes and the States: 2026
E.J. Smith - Your Survival Guy
E.J. Smith is Founder of YourSurvivalGuy.com, Managing Director at Richard C. Young & Co., Ltd., a Managing Editor of Richardcyoung.com, and Editor-in-Chief of Youngresearch.com. His focus at all times is on preparing clients and readers for “Times Like These.” E.J. graduated from Babson College in Wellesley, Massachusetts, with a B.S. in finance and investments. In 1995, E.J. began his investment career at Fidelity Investments in Boston before joining Richard C. Young & Co., Ltd. in 1998. E.J. has trained at Sig Sauer Academy in Epping, NH. His first drum set was a 5-piece Slingerland with Zildjians. He grew-up worshiping Neil Peart (RIP) of the band Rush, and loves the song Tom Sawyer—the name of his family’s boat, a Grady-White Canyon 306. He grew up in Mattapoisett, MA, an idyllic small town on the water near Cape Cod. He spends time in Newport, RI and Bartlett, NH—both as far away from Wall Street as one could mentally get. The Newport office is on a quiet, tree lined street not far from the harbor and the log cabin in Bartlett, NH, the “Live Free or Die” state, sits on the edge of the White Mountain National Forest. He enjoys spending time in Key West (RIP JB) and Paris. Please get in touch with E.J. at ejsmith@yoursurvivalguy.com To sign up for my free monthly Survive & Thrive letter, click here.