Dear Financial Samurai,
I wonder if a sort of money dysmorphia is once again permeating the land with so much wealth being created in the stock market and AI companies. Personally, I feel very blessed the S&P 500 is up 100% since mid-2022, or about 60% more than the historical average. But I've talked to many people offline who say they do not feel wealthier or blessed. Instead, they feel more stretched, largely due to inflation and rising costs.
For example, I went on a Girl Scouts field trip yesterday, and a dad told me he feels like he's running in place despite owning a primary residence, a rental property, a commercial property, and stocks. That was a surprise, but maybe not, because he also said this was the first year he had to pay for two private school tuitions, amounting to about $88,000 a year after tax.
Sure, spending an extra $44,000 a year is a lot. But is it really that much compared to the assets he owns and the raises he's gotten? I'm not sure. Maybe it's the fact that cash flow feels real, while asset gains feel fake. I got that jolt myself when a Redfin valuation update e-mail showed a single family home I own was 28% higher than the number I had anchored in my head for two years.
Here's a post I shouldn't have to write, but I did, because it seems like some folks are losing their minds and hurting their happiness as a result: Of Course $10 Million Is Enough To Retire Early.
The Desire For More, More, More
I love San Francisco, but one of the reasons I want to relocate to Honolulu is to be in a more chill environment. If everybody around you is hustling, you feel uncomfortable if you are not. And then you start wondering why people are working so hard when they already have way more than enough.
This growing dissatisfaction despite having more wealth is due to endless comparison, which results in the desire for more. It simply cannot be helped. From 2005 to 2014, I lived in a single family home on the north end of San Francisco that I had bought. But it took all my liquidity at the time, so I drove a secondhand car I purchased for $8,500.
My neighbor was this 25-year-old guy who lived for free because it was his parents' home. One day, he drove back and parked a brand new Toyota 4Runner right outside. I was jealous, because I loved that car. It was also the car the rich kids at my public high school in Virginia drove, along with the Ford Explorer.
My jealousy caused me to secretly look down on him and work harder so I could one day comfortably afford a nice car, based on my 1/10th rule for car buying. Ten years later, he was still living in his parents' home, saving so much money. I had decided to rent my house out and buy a 40% cheaper home on the west side. And with those savings, I decided to upgrade to a…… Honda Fit!
By 2014, when I moved to my cheaper home, I had already been out of the finance industry for two years. As a result, it was easy to stop comparing myself to my gung-ho peers. And in my cheaper neighborhood, I was surrounded by people with less wealth, which made it much easier to appreciate what I had.
If you want to stop grinding so hard, I highly recommend moving to an area that fits your stage of life better.
See: Buying A Multi-Million Dollar Home Ate Your FIRE Number
How's Your Sentiment?
Finally, I thought it would be fitting to share the latest University of Michigan Consumer Sentiment chart. We're at the lowest level in its history. Congrats everyone!
What a contradiction to the stock market and the overall improvement in quality of life we've experienced over the decades. It was a simpler life 40 years ago, as I can remember. But I'm not sure anybody would actually trade what we have now for what we had then.
One conclusion you can draw from this chart is that money does not buy happiness. We've all heard the phrase, and now we see it showing up in the data.
On the flip side, you can look at this chart and feel even happier. If you haven't been grinding away trying to make more money and you're already content, you feel great about all that saved effort, especially since the people who do grind appear to be less happy anyway.
So yes, filling up the tank of gas still stings and you still can't get a sub-3% mortgage, but maybe the massive gains in your investments more than make up for these higher costs. Or maybe not, and the world is simply a terrible place to be. It's up to you to decide.
To your financial freedom,
Sam
This is the last month I'll be sending signed copies of my USA Today bestseller, Millionaire Milestones. If you'd like a copy, sign up for a free financial review with Empower after linking over $100,000 in investable assets. Full details and instructions are in this post.
If you enjoyed this newsletter, consider sharing it with a friend who could use a reality check on their finances. And if someone forwarded this to you, you can subscribe here to get free weekly insights on building wealth, achieving financial independence, and figuring out what “enough” actually looks like. If you want to receive my posts in your inbox as soon as they are published, ad-free for the first three hours, sign up here.
Check out the May 30, 2026 Financial Samurai newsletter for more.