My Parents Did Everything Right and Still Got It Wrong

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My parents are worth roughly $5 million. I think. They did everything the American Dream promised: went to college, got good jobs, saved money, bought a house, stayed loyal to their employers for decades, collected pensions. By every traditional measure, they succeeded.

And yet, when I talk to them about money, they say things that are so disconnected from reality that my wife and I just look at each other in disbelief. They accumulated wealth over their lifetimes, but they still behave like people who are not wealthy. They hoard food. They stress about expenses that don't matter. They don't understand what things actually cost in 2025. They think it's still 2010.

I have three kids: 11, 10, and 8. My wife and I talk about money constantly with each other and with our kids. And the more I watch my parents interact with wealth, the more I realize: the script they followed worked for them because the world was different. That same script will destroy my kids' financial future if I let it.

I recently came across an article by Artful Parent titled "8 Ways Middle-Class Parents Accidentally Keep Their Kids Poor" and it all clicked. The patterns I saw in my parents. The advice they gave me that I ignored. The beliefs I internalized that I'm now actively unlearning.

This is my story. And if you're raising kids right now, this might be yours too.

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If I don't break these patterns, my kids will work until they die. They'll never have the freedom to decide what they want to do or where they want to do it. They'll live paycheck to paycheck, watching money leave their bank accounts every month to fund payments they signed up for, trying to convince themselves and the world that they're rich and wealthy when they're actually broke.

That's the future I'm trying to prevent.

Here's what I'm doing differently, and why it matters.

Growing up, the script in my house was: go to college at all costs, get a good job, stay loyal to a company, collect a pension. College was the only path to success. People who didn't go to college were looked at as less than.

It worked for my parents because times were different. College was more affordable. Fewer people had degrees, so they were valued more. Companies rewarded commitment with pensions. My parents lived in that professional world and it paid off.

But here's what they don't understand: pensions no longer exist for the overwhelming majority of people. When I confront them with this, they look at me like I'm lying.

They also looked down on studying business in college. In their world, you had to specialize, become a doctor, lawyer, engineer. Business was too vague, too risky. Entrepreneurship? Forget it. When I brought up starting a business, they said I was crazy. They said I'd work myself to death with minimal reward, and that taking a day off meant not getting paid.

I'd respond: "But working a corporate job for someone else is more rewarding? Those 10 days of PTO most people get?" They had no answer.

The constant message was: stability, stability, stability. Climb the ladder. Get into management. Avoid risk.

I don't have one specific opportunity I turned down, but the damage was cumulative. The constant erosion in my brain: stay safe, avoid risk, get the stable job. It shaped every decision I made in my twenties.

If I could go back to age 22, here's what I'd do differently: move to a tech city and join a startup. Even if I failed, the life experience and the people I'd be around would have been incredible. But I was too scared to pick my own path. And that's directly my fault now as an adult. Sure, I was a kid and didn't know better. But in hindsight, I should have taken more risks when I was younger.

If one of my kids says, "Dad, I want to skip the traditional four-year route and go straight into a trade or start a business," here's what I'll say:

Go for it. Know that you'll need to find a way to support yourself, but you can do it. College isn't for everyone, and I don't think it's worth the cost today. Try new things. You have the rest of your life to earn money and work. The worst thing that can happen is you go get a job like everyone else.

Working a job for a company caps your earning potential. Starting your own business? Unlimited.

My parents drilled saving into me my entire life. I remember going to the bank with them, cashing their paychecks, and putting a lot of it into savings. Later, they told me about Roth IRAs, but before that, investing was "risky" to them.

For years, I followed their advice. I saved aggressively. I had six figures sitting in a savings account earning 0.5-3% interest while inflation ate away at it.

I started watching my Roth IRA grow. The stock market was rising, and I thought: Why is all my other money just sitting there doing nothing? Sure, the market has ups and downs, but if you're in it for the long haul, you usually come out ahead. And seeing how much we were getting paid in dividends—free money—was motivating.

So within the last two years, my wife and I shifted. We started investing aggressively. We still max out our Roth IRAs every year, but now we're also putting money into taxable brokerage accounts. Our current savings rate is around 50% of our income.

They see a years' worth of expenses in savings as smart. I see it as opportunity cost. That money should be working for me, compounding, growing. Sitting in a savings account is safe, but it's not wealth-building.

I plan to show my kids our actual net worth sometime in 2026. They need to see the numbers. They need to understand that money sitting still is money dying slowly.

I have an MBA. It was free because I had a scholarship. And honestly? It was a total box check. It didn't teach me anything that actually makes me money today, in my day-to-day life.

The skills that have made me money like writing, critical thinking, problem-solving, I didn't learn in school. I learned them by doing, failing, and trying again.

If my 18-year-old son came to me and said, "Dad, I want to learn copywriting and start freelancing instead of going to college," here's what I'd do:

I'd support him financially. But it would be structured like a real investment. I'd get a certain ownership stake in his business as an investor. We'd outline expectations and treat it seriously. He's an adult at 18, so he'll be treated as such. I'll be totally supportive, but he'll learn how the business and entrepreneurial world actually works.

My parents would never do that. To them, skipping college is failure. To me, it CAN be an opportunity.

Growing up, my parents talked about money, but not openly. They'd joke in an awkward way about things being expensive. "I'm going to need to take out a second mortgage for this," they'd say, laughing to make it less uncomfortable. But we didn't have real conversations about income, debt, or investing. Those stayed behind closed doors. (Or maybe never even happened?)

My wife and I talk about money with our kids all the time. We've told them what our house costs ($410,000 for 1,500 square feet in Alaska). I'm not sure it totally sinks in because what is $410,000 to a kid who has $30 in their piggy bank? But we're planting the seed.

Here's the conversation my parents would never have had with me:

"We can afford that, but we're choosing not to buy it."

Most parents say, "We can't afford that," to get their kids to stop asking. That's a lie, and it's toxic. It plants a scarcity mindset in their heads. They internalize the message: we're struggling, we don't have enough.

When I tell my kids, "We can afford it, but we're not buying it," the message is different: We're financially okay. Don't worry. But we're not buying that for you.

My youngest sometimes gets whiny. But I think all three of them, beyond their annoyance, respect it. (As much as small kids can) They're learning that money is a choice, not a constraint.

We had a close family friend growing up who owned a carpet cleaning franchise. He never went to college and did very well for himself. My parents always said, "Look at how hard he has to work, and if he takes a day off, he doesn't get paid."

I'd say, "But the money he earns is for him, not someone else."

They never had a sensible response. They saw it as too risky.

I've tried and failed at many side hustles before this newsletter. Mostly writing-related, because that's all I have time for. I’ve yet to break even on the Ian-P&L. But this newsletter has been the longest I've stuck with anything, and after two years, it feels like a path that might work.

If it fails, I'll try something else. I have a job that pays me, but I'm not going back to "safe" as my only option. My wife and I are 100% on the same page: we're creating our own destiny and building generational wealth for our kids.

They thought business owners were reckless. Too much risk. Too much work. Not enough stability.

I've never been opposed to working hard. I just want my time and effort to reward me directly. Is that a crazy concept?

My parents drilled this into me: buy a house as soon as possible. Renting is throwing money away, they said.

As an adult who owns a house now, I recommend renting for most people around my age.

Our mortgage payment is about $2,900 per month. We qualified for more, but we chose not to. We bought a 1,500-square-foot house for $410,000 because we didn't want to be house-poor.

But here's what I'd do differently: we should have kept our previous houses and rented them out. We bought houses before that are worth a lot more today than we paid. But my parents said, "Being a landlord is too risky. You don't want to do that." So we sold them.

That advice cost us hundreds of thousands of dollars in equity and rental income. Realistically, we would be millionaires by now if we kept them.

Renting gives you options. You're not paying for maintenance. You have the freedom to leave after your lease. You're not locked into a location for 30 years.

Stability is money. Freedom is wealth.

My parents are worth roughly $5 million. Probably. They did it right by the old rules. But they have no idea how much things cost in the real world today. They don't feel the financial pain everyone else does because of their wealth.

Last year, I told my dad I could collect my pension at 49 and never work again. He said, "No, you don't want to do that. You'll go crazy. You want to get another job and get a second pension."

No. Absolutely not. NO FUCKING WAY.

He has a friend who worked two careers and has two pensions. That guy is in his 70s now. How many good years does he have left to enjoy that money?

I refuse to work until I'm 70. My goal is to be work-optional by my late 40s. My wife and I are building toward $10 million in net worth by age 50. That's the number we made up that gives us total freedom.

Here are the family money rules I want my kids to internalize:

My 10-year-old son sees other boys at school with the latest junk from YouTube or TV. He wants it too. When we ask him why, he can't give a reason. He says, "Well, so-and-so has it."

It's the clearest example of how people spend money to look like and feel like others.

I tell him: "We can afford it, but we're not buying it." And I explain why. Not because we're mean. (Well, maybe we are) Because we're building something bigger.

The hardest part of raising my kids differently is saying no when their friends have the latest junk. Explaining delayed gratification. Sometimes I feel like the mean parent. But then I remember: I'm not their friend. I'm their parent. Big difference.

Do I worry I'm being too extreme or depriving them? Not at all. They'll be ahead of their peers with an understanding of how money and the real world work. (If they have to go to therapy as adults because we deprived them of trinkets when they were kids, I can live with that. We could have done far worse!)

If you're reading this and you have kids, here's what I want you to do:

Evaluate your life. Do you have money but still act like you're poor? How were you raised? After reading this, do you recognize the signs?

Think about how you'll talk about money with your kids. Stop the cycle. Talk to your kids about money before someone else, or the internet, does.

If you're thinking about forwarding this to your parents and saying, "This is why I'm doing things differently," I hope it starts an honest conversation. Not a fight. Not defensiveness. Just honesty.

My goal is simple: so much wealth that my kids don't have to work.

That sounds gross to some people. But here's what I mean: I want them to have the freedom to run a business and take risks on themselves. I want them to be able to bet on themselves instead of taking the safe route that leads most people to professional misery.

We drive older, paid-off cars. We live in a modest 1,500-square-foot house with five people and a dog. We go thrifting. We budget our groceries. We don't buy our kids everything they want. We will not have spoiled kids.

But we will have kids who understand money. Kids who know that working for 40+ years is a miserable existence. Kids who know they have other options.

This essay was inspired by Artful Parent's article, "8 Ways Middle-Class Parents Accidentally Keep Their Kids Poor." It's worth reading in full. It named the patterns I was seeing and gave me the language to articulate what I'm doing differently.

My parents did everything right by the rules they were given. But the rules have changed. The world is different. What worked for them won't work for my kids.

And that's okay. I'm not mad at my parents. I'm grateful for what they taught me. But I'm also clear-eyed about what I need to unlearn.

If you're raising kids right now, you have a choice. You can follow the script you were given, or you can write a new one.

I'm writing a new one.

Watches mark time. The choices behind them mark intentions.

—Ian