You Did Everything Right. So Why Does It Still Feel Harder?

My mom raised two boys on her own.

There were times she’d take my brother and me out to dinner and tell us she wasn’t hungry.

I believed her back then. Years later, I realized the truth: She couldn’t afford three meals.

She worked overtime and stretched every dollar as far as it could go. For much of my childhood, one unexpected expense could throw everything off course.

But here’s something else I remember about growing up: By her early 30s, my mom owned a home.

A place with a yard, in a middle-class neighborhood, where two boys could run around. The kind of home most people would consider a pretty ordinary piece of the American Dream.

Over the years, she owned a few homes like that – one at a time, of course.

Today, I drive around my hometown and point them out to my wife.

That’s the house we lived in when I was six. There’s the neighborhood we moved to after that. Here’s another house my mom owned later.

And we both marvel at something: Somehow, a single mother raising two kids on one income could still get into a decent house.

Now I’m in my early 30s, trying to buy my first one. And I’m discovering just how much the world has changed.

Perhaps the simplest way to see what happened is to compare home prices with incomes.

The median single-family home now costs roughly five times the median household income. In the 1990s, that ratio typically hovered around 3.2.

In the 1980s, the typical first-time homebuyer was in their late 20s. Today, they’re 40.

Those numbers caught my attention because I’d always assumed that if I earned, saved, and invested responsibly, buying a normal house would be relatively easy.

There’s an old joke that people my age would be able to afford houses if we’d just stop buying avocado toast.

So, in a way, I ran the experiment.

I started my adult life with more than $100,000 in student debt. I worked while finishing my master’s, kept my lifestyle relatively modest, saved, and invested.

Today, I’m fortunate enough to be worth seven figures. And still, when my wife and I started looking for a house in the Midwest, I was surprised by what our money actually buys.

The median single-family home in America now sells for about $435,000. So we set our budget below $500,000 – far from mansion territory in today’s market.

Again and again, the houses we’ve found come with problems I never expected at that price. Flooded basements, questionable foundations, asbestos, and tens of thousands of dollars in immediate repairs.

I’m not telling you this so you’ll feel sorry for me. I’m grateful for what I have, and I owe so much to the sacrifices my mom made.

So why do I bring it up? Because when I looked at the numbers, I realized the same pressure is showing up all around us. And maybe you’ve felt some version of it yourself.

You’ve saved. You’ve watched your budget. You’ve put money into traditional investments. You’ve done the things responsible people are told to do.

And somehow, the number that once looked like “enough” keeps getting farther away.

If that sounds familiar, you’re not imagining it.

The Financial Finish Line Is Moving