Imagine working your entire life, playing by the rules and still ending up in dire financial circumstances.

It’s a sobering reality for many Americans and it’s a problem that won’t be getting better any time soon.

But how did we get here?

My grandparent’s generation lived on a single income and managed to raise 4 children, own a home, take vacations and retire at a reasonable age.

Their children, the baby boomers, grew up assuming this would be their fate as well.

They got jobs, had children and bought their first home. They had pensions, health insurance and most importantly, they had faith in the American dream. They lived as if the dream was a certainty.

Sure, they’ll tell you they had it a little harder than their parents did. They paid high interest rates for their mortgages. They often worked several jobs over their lifetimes and had to tighten their belts to ensure the same financial stability the previous generation enjoyed.

The truth is, most were born on third base, but somehow convinced themselves they hit a triple.

Their first house was tens of thousands of dollars. Their college tuition was a few grand. Many were left inheritances from their parent’s diligent savings.

That’s not to say they didn’t work hard. They did. They followed the rules as they saw them and eventually rose to power. As they aged, they adjusted the rules to better suit their needs. Property tax breaks, increased social security and policies designed to help them keep their hard earned money.

However the boomers are living longer than even they anticipated. That nest egg they so carefully nurtured is now a drop in the bucket compared to what they thought they’d have. 

According to a 2024 study by Northwestern Mutual, only 22% of boomers plan on leaving an inheritance despite currently holding roughly 50% of the wealth in this country. 

Now enter the next generation.

The average age of a first time homeowner is now 40. When I was born, it was 29.

The average cost of a home in the US is now between $300-$400k. The median sales price in 1984 was around $80k.

It’s like we were born on first, but can’t move forward because the bases are still loaded.

Boomers are staying in their homes longer while bemoaning the fact they still have to pay property taxes. While I’m certainly not saying they don’t deserve to stay in their homes, what else can our country do to further enrich the wealthiest generation?

Keep in mind I’m generalizing a great deal. Not all seniors have piles of money or million dollar homes. But by and large, the disparity between generations is at an all time high.

I’ve saved for my own retirement since I turned 18 and I’m still wondering if I’ll ever have enough to stop working. 

How do I tell my kids they’ll grow up to own a home someday when chances are they’ll never be able to afford it?

How can they be expected to save for their own retirement when the cost of everything continues to rise?

How can we reconcile the American dream with the American reality?

I’m not blaming the previous generation. I’m not even saying that my generation won’t make it worse.

I guess what I’m saying is…

What the hell?!

I don’t have the answers, but if you do, shoot me an e-mail and let me know how I look my kids in the face and tell him they’ll be ok.

Thanks!