Pete the planner: You can learn from others’ failures but consider the context

Back in the late 1980s, upon exiting my Pike Township school bus and snarfing my post-school snack, I’d often rush to the TV to tune into ABC to watch “Afterschool Special.” For those who don’t remember, or who never were exposed to this cultural phenomenon, it was a show produced for kids and teens, with the express purpose of exposing them to controversial topics and modern-day social and behavioral lessons. From the comfort of my living room, I could watch kids my age make all sorts of horrendous decisions. Then I would learn to not make those same mistakes.

I loved it.

To no surprise, I’ve spent the last 30-some years attempting to learn from the mistakes of others, so that someone else’s pain could end up being my gain. That sounds much worse than I meant it. I just don’t want to repeat someone’s mistake, and I’m absolutely OK with people learning from my mistakes, too. You know how all this works.

I often do it on the heels of witnessing or learning about a person’s failure. Then I spend 20 minutes or so putting myself in their shoes, making one or two different decisions, then coming out the other side with a success. Again, this sounds much grosser than I had imagined.

Wait, maybe this practice has become gross. Maybe I’ve been classifying a simple misfortune, or my own misunderstanding, as cautionary tales that could easily be avoided. And it’s possible you’ve been doing this, too, when you observe the financial lives of others.

There are a few different categories in which we tend to observe, judge and “learn” from others. The first, and most obvious, is spending. If a friend buys a car that’s too expensive or remodels a kitchen that seems to cost more than the home is worth, we mentally file it away. “Well, I’m not doing that,” we say to ourselves, smugly eating our microwaved leftovers in our unrenovated kitchen.

But here’s the problem: We usually don’t know the whole story. Maybe they got a massive raise. Maybe they inherited money. Or maybe—yes, maybe—they made a giant mistake. The point is, we fill in a lot of blanks that don’t belong to us.

The second category is lifestyle. I’ve caught myself assuming someone’s vacations or private-school tuition or new pool installation is a sign of irresponsibility. That’s the dangerous trap of observational finance. We pretend to be financial anthropologists, making conclusions from afar—like, “See? That’s why they’re always stressed,” or, “I bet they carry a balance on their credit card.”

What a bizarre and slightly arrogant game to play. And yet, I do it. You probably do, too. It’s the financial version of rubbernecking.

But the third category is where things get tricky: It’s when we learn from someone who seems to be winning. It’s easy to spot what not to do when someone fails, but what about the people who seem to be getting it all right? That can be just as misleading. You see someone retire early, invest in something hot, or make a big bet that pays off. And suddenly you’re reverse-engineering their decisions into a financial philosophy. “Well, if they did X and ended up at Y, maybe I should do X, too.”

It doesn’t work like that. Not always.

Their risk tolerance isn’t your risk tolerance. Their salary history isn’t your salary history. Their lucky breaks aren’t your lucky breaks. And yet we try to squeeze our own financial circumstances into someone else’s mold, because it feels like we’re learning.

Now, don’t get me wrong. Learning from others can be an incredibly effective strategy. But it only works when we add context. When we understand that what worked for one person might not work for us. When we stop interpreting mistakes or victories as a universal playbook.

So how do we still benefit from observing others without turning it into financial voyeurism?

Here’s what I try to do (on my better days):

1. Ask better questions. Instead of thinking, “Why would they spend that much on a wedding?” I try to ask, “What are they prioritizing right now?” That question feels less judgmental and more educational. And often, it reminds me that people are allowed to value different things than I do.

2. Reflect on my own values. When I see someone make a choice that feels reckless, or wildly smart, I ask myself whether it aligns with my values or whether I’m just reacting to the optics. You can admire a good decision without mimicking it.

3. Give people the benefit of the doubt. Most of us are doing the best we can with the knowledge we have. Financial mistakes aren’t always due to ignorance. Sometimes they’re born from optimism, bad timing or necessity.

When I look back at the “Afterschool Specials” of my youth, I realize now that they weren’t just teaching me to avoid danger. They were teaching me empathy. The characters weren’t villains; they were kids fumbling through tough choices. And as much as I loved the moral at the end, the real value was watching someone else struggle and knowing that messing up didn’t make them broken. It made them human.

And maybe, just maybe, the best financial lesson we can learn from others is that nobody gets it perfectly right. We’re all just trying to put together an episode that ends with a little hope, a little growth, and maybe a freeze-frame of us high-fiving in the living room.•

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Dunn is CEO of Your Money Line powered by Pete the Planner, an employee-benefit organization focused on solving employees’ financial challenges. Email your financial questions to [email protected].