What Parenting Has Taught Me (So Far) - Lessons 1-5

Some lessons from my most important role

This post is inspired by something that Brandon Beylo posted on X. Some of the responses are so fascinating to me. But that’s not what I want to talk about today.

I often post about my experience as an investor. I remember how intimidating it felt starting out — how much I would have benefited from reading certain ideas or hearing others talk openly about the journey. The same is true for parenting.

I don’t know how many of my readers are parents or plan to be someday, but I thought I’d share a few personal reflections.

I have two boys, aged 15 and 9. While it’s not central to the lessons, for context, I’m a divorced co-parent.

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1) Your template matters more than you think.

The parenting style you grew up with inevitably shapes how you parent — often in ways you don't fully realize until you're deep in it. Some of that inherited “template” you'll want to pass on. Other parts, you'll want to change.

In my case, my father was direct. Feelings weren’t really validated — it just wasn’t his strong suit. And when I’m tired, stressed, under-carbed, or stretched thin, I notice some of that same tone coming out in me: being a little too gruff, too dismissive, or handing out consequences that don’t match the crime. It’s something I’ve had to become aware of and actively work on.

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2) Your kids are not you. They are not your do-over.

Every parent has moments where they think, “I wish I had done X when I was younger.” And it’s natural to want your kids to avoid those same missteps. But that can tip into trying to relive your own life through theirs.

I wasn’t a stellar student. I coasted until about Grade 9, when girls and part-time jobs started to matter more than school. Looking back, I wish I’d taken high school more seriously, and gone to university. Would it have made me happier or richer? Maybe not. But I do think it would’ve pushed me to grow faster — to take ownership and learn from different perspectives earlier.

Now that my oldest son is at that same stage, I have to remind myself: I can encourage him. I can set boundaries — no screens until chores and homework are done, for example — but I can’t force him to care. At some point, it has to come from him.

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3) This is not your generation.

Sometimes being a parent today feels like being on a different planet. The expectations on parents today are vastly different from a few decades ago when I was a kid. The norms have shifted. Navigating it is very challenging, at least for me. The internet and age of social media has brought us so many benefits, but it has some nuances. I will be honest, sometimes I feel that we are screwed and need to go back to “the good old days”.

Schools now expect parents to be much more hands-on. Playdates require coordination. Outside time is practically non-existent for many kids. When I was a kid, we were outside until the streetlights came on, riding bikes with no supervision. That’s not the norm anymore.

Whether that’s better or worse is debatable — but it is the reality. And as parents, we have to adapt.

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4) Their problems are big to them - even if they are small to you.

As adults, we have the life experience to know that life will demand so much of you. Many of our children (and us as kids) did not realize this until we were in the thick of a crisis. Looking back, many of those problems as kids were so minor. But to a kid they are not.

I wasn’t raised in an environment where my concerns were always taken seriously. I heard a lot of, “You think that’s hard? Just wait until you're an adult.” I’ve caught myself saying the same thing — or at least thinking it. But I try hard to avoid it.

Validating their feelings, no matter how trivial they seem, is something I’ve worked to improve. It’s not easy when life is already demanding, but I’ve found it makes a big difference in the long run.

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5) Adversity is good - even when it doesn’t feel like it.

We all know that struggling is good for growth. But it’s hard to watch your kid go through it. Whether it's bombing a test, getting cut from a team, or having trouble with friends, your instinct may be to jump in and fix it.

But often, the best thing you can do is just listen. Let them figure it out. Ask, “How can I help?” or “That really sucks. What would you like to do about it?” instead of stepping in with solutions.

Executive function is still developing in kids. They fumble. They give up. I’ve swung too far in both directions — from being overly involved to being too hands-off. It’s not easy to find the right balance. But I’ve learned that giving them agency, even if it means watching them stumble, builds resilience.

I want to make it clear that I’m not advocating for you to ignore something very serious like your kid getting bullied, but to allow them to have agency in their problems.

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Closing Thoughts

If you are a parent and have something to say on the subject, I would love to hear about it. Even if you aren’t a parent and have something to say, let me know.

Thanks for reading my work.

Dean