Money for Boomers: Richer Than Our Parents, Broker Than Our Kids Think

How we lived through recessions, 18% mortgages, and still bought avocado toast before it was cool

Money is weird. It is like oxygen. You do not think about it until you are running out, then suddenly every breath is a spreadsheet. Boomers like me grew up in a world where money was supposed to make sense. Work hard, get paid, buy a house, retire. Simple. Except it was never simple, it was a pyramid scheme with better branding.

My parents had none of it. They were lower middle class with bad credit. No checking account. Bills paid with money orders at the A&P customer service counter. I thought that was normal. You grow up thinking financial chaos is just how the universe runs. Like the sun comes up, and you hide from creditors. You learn to treat the phone like a landmine. To this day, I still get that twitch in my chest when an unknown number pops up, even though now it is just a scammer pretending to be the IRS. Trauma in 10 digits.

When I hit adulthood, I thought I would break the cycle. I went to college, joined the Navy, got a job. But here is the sick joke: no matter how much you make, money feels like it is always sprinting ahead of you, mooning you as you chase it. I would get raises, promotions, bigger checks, and still somehow end up broke by the 20th of the month. Money management felt like trying to keep a hamster alive in a microwave.

And it is not just me. It is all of us. Boomers are supposed to be the wealthiest generation in history, but we are also the most financially anxious. We are richer than our parents, sure. Our parents lived like Depression holdovers, rinsing out Ziploc bags and saving bacon grease in Folgers cans. They would rather eat Spam than go into debt. We? We signed up for 30-year mortgages like it was a ride at Disney. Credit cards? Yes please. Points, cash back, miles, perks. It all felt like free money until you realized you just mortgaged your future for a set of steak knives and a trip to Cleveland.

And then came the recessions. Plural. Every decade, some new financial plague arrived like a biblical punishment. Oil embargo in the 70s, Black Monday in the 80s, dot-com crash in the 90s, housing collapse in the 2000s, pandemic in the 2020s. We got whiplash. My first mortgage was 18 percent. That’s not a mortgage. That’s loan shark territory. You buy a house at 18 percent and you do not own it, it owns you. Every month you are basically mailing in a ransom note to the bank hoping they let you keep your own roof.

And through all of this, we bought avocado toast. That’s right, we invented it. Sourdough, avocado, a sprinkle of salt. We were eating it in the 70s before millennials got accused of killing the housing market with it. I swear, some kid on Twitter thinks Boomers had it easy, as if every one of us was living like Richie Rich. Meanwhile, I was making 16 grand a year and driving a car that shut off at red lights unless I held the gas pedal down with both feet. But sure, avocado toast destroyed my retirement account.

Let’s talk about retirement. You know that dream where you work 40 years, then coast into the sunset with a pension? Pensions went extinct right around the time we were actually counting on them. Like Blockbuster. We were halfway through the movie and the lights shut off. Suddenly it was all 401ks, IRAs, and “do it yourself” retirement. It is the cruelest trick in the book. “Here, you manage your own portfolio while raising kids, working full-time, and trying not to die of stress. By the way, if you screw it up, you are eating cat food at 72.” Thanks, capitalism.

Meanwhile, financial gurus pop up on TV like prophets with perfect teeth. Suze Orman, Dave Ramsey, that guy yelling about compound interest like it is magic fairy dust. All of them with the same basic message: you are stupid and should stop buying lattes. The latte factor, they call it. Skip your three-dollar coffee and you will retire in comfort. Yeah, because that $3 a day adds up to a beach house in Sarasota. Forget the medical bills, the job losses, the fact that your boss tanked your pension fund on a bad bet. It was the lattes. Sure.

Money paranoia never leaves. You can be doing fine, but that childhood wiring keeps buzzing in your head. I could have a thousand bucks in my pocket and still feel broke because my parents lived in a permanent state of scarcity. I check bank balances like I am defusing a bomb. I never trust a paycheck. I assume every good thing is temporary. And it makes sense. In our lifetime, we saw jobs shipped overseas, industries collapse, inflation spike, entire retirement accounts wiped out. It conditions you to think money is sand slipping through your hands.

And then there are the kids. Our kids, Gen X, millennials, Gen Z. They look at us like we are rolling in it. They think every Boomer is sitting on a mountain of property value and fat pensions. And yeah, some are. But most are just like us—paycheck to paycheck, juggling credit card debt, one medical bill away from panic. The difference is our kids have it worse. They are saddled with student loans the size of mortgages, jobs that treat them like temp workers, and housing prices that make Monopoly look realistic. They are screwed six ways from Sunday, but they think we had it easy.

What they do not get is that we are broke in spirit even if we have a little in the bank. We are rich compared to our parents but poorer than we thought we would be. It is like running a marathon only to find out the finish line moved three miles down the road. There is no resting place. There is just the hustle, until you collapse.

And yet, here is the dark comedy of it: money does not actually solve the thing you think it will. You get some, you want more. You pay off debt, you take on new debt. You save for the future, the future inflates and eats it alive. You never win. At best, you survive. At worst, you die with a Costco cart full of Ensure.

I used to think I was one lucky break away from financial security. A better job, a better salary, a smarter investment. Every time, it was the same. More money came in, more money went out. It is not just income, it is behavior, it is wiring, it is the system itself. Capitalism is a treadmill with no off switch. You are running, sweating, screaming, and the machine is just humming along, happy to grind you into pulp.

But here is the kicker: even with all the dysfunction, we Boomers pulled off something insane. We survived. We raised families through recessions, paid mortgages at gangster rates, lived without credit and then drowned in it, and still managed to keep the lights on. We are not rich, but we are resilient. We are broke, but we are not broken. We can laugh about it, because what else are you going to do? Cry into your empty Folgers can?

Money is not freedom. Never was. Money is just the ticket you buy to stay on the ride. The trick is realizing the ride ends whether you bought first class or not.