The Questions We Forget to Ask Ourselves

Last month, I was sitting with a couple, the Hughes family, working through their financial plan. Their oldest was heading into his senior year of high school, and we were talking through the numbers for college.

At some point, the dad said something that caught me off guard. He said, "We just want him to have the same opportunities we had."

It sounds so reasonable. Of course, you want that for your kids. But I couldn't stop thinking about it. What does that actually mean? And more importantly, is it even possible?

It set off a series of questions I recently read by Morgan Housel.

1.      Which of my current views would I disagree with if I were born in a different country or generation?

2.      What haven't I experienced firsthand that leaves me naive to how something works?

3.      What is a problem that I think only applies to other countries/industries/careers that will eventually impact me?

It's the kind of question that sounds philosophical at first. Something you'd debate in a college seminar. But the longer I sit with it, the more I realize it's one of the most practical questions you can ask yourself, especially when making decisions about money, your career, or your kids.

The Script We Inherit

The Hughes had a script. Four-year college, professional degree, corporate career. That's what worked for them. That's what their parents did. That's what everyone they knew did.

But their son wanted something different. He was interested in the trades. Electrical work, specifically. And they were having a hard time with it.

Here's the thing. When I ran the numbers, the financial case for a skilled trade was actually really strong. Good starting pay. No student loan debt. Job security in a field where demand keeps growing. But that wasn't really what they were wrestling with.

They were wrestling with a script that said success looks a certain way. And that script wasn't based on data or even on their son's specific situation. It was based on where they grew up, when they grew up, and what was normal in their world.

I asked them a simple question. If you were starting out today, with today's student loan debt, today's job market, today's housing costs, would you make the same choices you made? They didn't have an easy answer.

What We Don't Know We Don't Know

The second question is the one that humbles me: What haven't I experienced firsthand that leaves me naive to how something works?

For most of my career, I thought I understood job loss. I'd helped clients through layoffs. I'd seen the numbers. I knew the playbook. I had even been through a job loss myself.

Then I walked away from my own twenty-year corporate career. I'd been a CFO at a private equity firm. I'd managed large teams. I had all the right credentials. And even though leaving was my choice, even though I knew it was the right move, I wasn't prepared for what it actually felt like.

The identity piece. The way people looked at me differently. The quiet panic at 2 AM, wondering if I'd made a massive mistake. None of that was in the playbook.

Now, when I work with someone going through a career transition, I'm a little more careful about what I claim to know. I can help with the financial pieces. I can help think through options. But I don't pretend to have all the answers about what that experience is actually like for them.

I think about this a lot when I'm working with widows. I've helped many families through the death of a spouse. I understand the financial complexities. I know what needs to happen with accounts, beneficiaries, and estate documents. But I haven't lost a spouse. I don't know what that grief actually feels like from the inside. All I can do is meet them where they are and help with what I can help with.

The danger lies in forgetting the limits of our own experience. When we assume that because we understand something intellectually, we understand it fully. We don't.

The Problems That Don't Apply to Us (Yet)

The third question might be the most important for busy parents: What is a problem that I think only applies to other countries, other industries, other careers, that will eventually impact me?

Five years ago, when I talked to families about their careers, artificial intelligence was barely part of the conversation. It was something happening in tech. Something happening to other people. Now it comes up in almost every planning meeting. People in fields I never would have expected are asking, 'Will this job exist in 10 years?'

Healthcare costs are another one. I work with many young families who know healthcare is expensive, but haven't yet experienced what it's like to pay for it entirely on their own. They haven't seen what a chronic illness does to a financial plan. It's a problem they know exists, but they haven't felt it yet.

Housing affordability. The cost of eldercare. The way work itself is being restructured. These aren't problems that only affect other people. They're headed for all of us, in one form or another.

Theresa and I talk about this with our kids. The triplets are fifteen. Mackenzie is thirteen. The world they're going to graduate into looks different than the one we entered. I catch myself sometimes wanting to give them the playbook that worked for me. Go to school. Get the degree. Build the career the way I built mine.

But that playbook was written for a different game. The rules have changed. Some of what I learned still applies. A lot of it doesn't. And the hardest part is figuring out which is which.

Values vs. Scripts: A Quick Filter

Here's where I want to get practical. Because if you're anything like the families I work with, you don't have time to question everything. You're already making a hundred decisions a day. Adding "but what if my entire worldview is wrong?" to every choice isn't helpful. It's paralyzing.

So here's the distinction that helps me, and that I use with families often.

There's a difference between values and scripts.

Values are yours. They're the things that actually matter to you, that don't change based on what other people think. Wanting your kids to be self-sufficient. Wanting financial security. Wanting to be present for your family. Those are values.

Scripts are different. Scripts are inherited instructions about how to achieve those values. And here's where it gets tricky. We confuse them constantly.

"Self-sufficient" becomes "must have a four-year degree." That's a script.

"Financial security" becomes a specific net worth number you saw somewhere. That's a script.

"Being present" becomes "never miss a single event, ever." That's a script.

The value underneath is solid. The script is just one way to get there, and it might not even be the right way for your family.

Values are worth protecting. Scripts are worth questioning.

The "Says Who?" Test

Here's the quick filter I use. When I feel strongly that something should be a certain way, I ask myself two words: says who?

If the answer is "because that's what my parents did" or "because everyone I know does it this way," I pause. Not to reject the belief. Check whether it still applies.

If the answer is "because I've thought about this and it aligns with what actually matters to my family," I trust it and move on.

This takes five seconds. You can do it in the car, in the shower, in the gap between meetings.

And if you want to focus on this work, here are the three places where I see inherited scripts cause the most damage:

What your kids should do after high school. The college-or-bust script is probably the most expensive inherited belief most families carry. If you feel strong resistance to your kid's path, run the "says who?" test before you push back. You might find you're protecting a script rather than a value.

What "enough" money looks like. If your savings target keeps moving, if you hit a number and immediately feel like it's not enough, that's a sign you're chasing a script, not pursuing actual security. Real enough is based on your life. Scripted enough is based on comparison.

How you define a successful career. Title. Salary. Prestige. Office with a window. These metrics came from somewhere. Before you push them onto your kids or chase them yourself, ask whether they're actually yours.

Seeing Our Own Stories

Here's what I've come to believe. Every financial plan is built on a story. The story you tell yourself about what's possible, what's realistic, what success looks like, and what "enough" means.

And most of those stories, we didn't write ourselves. We inherited them. From our parents. From our neighborhoods. From the time and place we happened to grow up.

That doesn't make them wrong. But it does mean they're incomplete. And it means some of them might not fit the life you're actually living.

Asking these questions isn't about second-guessing everything you believe. It's about sorting the values worth protecting from the scripts worth questioning. It's about holding your beliefs with a little more openness. A little more humility. A little more willingness to consider that your perspective is just one perspective.

The Work This Week

So here's what I'd invite you to do. This week, notice when you feel a strong "should" about money, about career, about what your kids need to do. Just notice it.

Then ask one question: is this my value, or is it someone else's script for achieving it?

If it's your value, trust it and move on. You don't need to defend it or explain it. It's yours.

If it's a script, give yourself permission to write a different one. One that actually fits your family, your circumstances, your life.

Money is a number. Enough is a story. The question is whether you're writing your own story or just repeating the one you were handed.