Mistakes I Made as a Teen that I Hope My Children Don’t

My daughter is 13 years old and will be starting some of her pretty formative years that could affect the rest of her life. And she has a very similar personality to mine, tentative, painfully shy, and smart (if I do say so myself). Her situation is much different than mine, different family, different city, different cultural dynamics at play but I can already see some of the same challenges I faced affecting her. But I won’t use this post to talk about her, rather I’ll talk about me.What mistakes did I make that I hope she doesn’t.

Find Your Own Path… Socially

I spent a lot of time wanting to belong to the cool kids, obsessing over the pretty girls, wanting to do what the cool guys were doing. I authentically enjoyed sports, especially basketball. I’m thankful for the years I’ve played it. But I obsessed about sports for all the wrong reasons. I saw it as my path into the cool crowd. The cool kids were athletes. The athletes were dating the pretty girls. I thought that athletics could be my ticket to, well, these sorts of relationships.

First of all, which was pretty dumb. Understandably, if I was an amazing athlete it would have led to some pretty serious social capital. But if that’s all I had, I doubt it would have been enough. Second of all, I wasn’t an amazing athlete. I was too small, too slow, too weak naturally to ever really make it. I practiced, especially basketball, a lot. Dribbling the basketball everywhere I went, spending time in the gym on a shot that never really came. But I was shy remember, and timid. I didn’t spend nearly enough time on the playground, playing the game with kids bigger and better than me. When I did, I was too shy and timid to really take it to them.

And I did have friends, really great friends. That should have been enough.

My daughter’s social situation is different. She’s had friends since childhood, some are blossoming socially in ways my daughter isn’t. She can appreciate their friendships and make friends with other people as well. There will always be someone who needs a friend.

Use My High School Years to Experiment

There’s really nothing like being in high school. You grow and mature and develop physically, emotionally and mentally very quickly. A teenager’s capacity can be actually quite high. Many kids have the potential to accomplish more than many adults. But they have not yet been released into adulthood. They don’t (or shouldn’t) have to support a family or to even pay a mortgage.

I wish I would have been part of the chess team or fiddled with computers or been part of a debate team or canvased for a politician. I had other interests and definitely other, better skills besides sports. I was shy, but I could have leveraged some of natural skills to overcome my shyness sooner. I loved politics at a young age, I would have benefited from a debate time or a writing club. Yuma wasn’t a mecca of opportunity, but there were opportunities at school I could have done more to leverage.

My kids are in sports, but more for, stay well-rounded, get physical fitness, kind of reasons. Thanks to my piano-playing wife, they are all heavily involved in music. I want my kids to use high school to try a number of different things, find their interest and leverage the guts out of the resources to go as far as possible pursuing them.

With interests come like-minded friends which could also solve the social problems above.

Don’t Worry about Serious Dating Until College

I didn’t date, at all, in high school. That was a mistake. But I really wanted to date seriously in high school. I dreamed about having a serious girlfriend. I had crushes. That was also a mistake. High school is a time to develop social skills, it’s not a time to lock in exclusive relationships. High school is a time to figure yourself out, try different things, develop skills. It’s the time when your body is finally starting to develop into maturity, when we are preparing to become men and women, but do not yet have the responsibilities of an adult. It’s prime time to crank up our passions another notch. To try out for the orchestra or the swim team or the debate team. It’s not a time to waste hours of your time with a single member of the opposite gender.


I don’t think I missed anything by not dating exclusively and probably avoided a lot of painful pitfalls. I did miss something by not having regular more casual, eventful casual outings with friends of both genders. I had female friends, those were good. I should have spent more time with them, girls and boys, in groups, having fun. I didn’t go to prom. I regret that. I should have, with a girl I was comfortable with, attending as a group with other friends. I should have had fun.

I took these events too seriously. I wasn’t ready for the pressure I put on myself. I hope my daughter finds friends that she’s comfortable with, boys and girls. I hope none of them are especially cool – very few high school kids really are. They are all, mostly awkward and insecure trying to figure out life like everybody else. I hope they just feel comfortable enough to have fun with each other. Lower the stakes. High school is not the time for big decisions. It’s a time to have fun, to grow, to develop, to try new things, to discover talents.

Go Easy on Yourself, Take Risks and Learn Resiliency

This is a difficult lesson, but I’m inspired by a session I had recently with  Christian Moore about resiliency. At school, I did not want to fail. I stressed over every answer, fretted over every exam. A big part of my identity was wrapped up in getting a grade. But that was the easy part. I tended to pull back in other ways, far too often. I want my daughter to just try. Put herself out there. Offer an answer, ask a question even if the its a wrong answer or a bad question. The more they try, the more they’ll fail, the more they’ll learn to keep trying and to pick themselves up each time.

Stay in Your Lane and Appreciate The Lane Your In

This world takes all kinds. At certain times and in different contexts, we’ll all be leaders and followers, the star and the supporting cast. We need our introverts and our extroverts, our naturally born liberals and conservatives. Our religious zealots and our secular humanists. We need all of us. I hope my kids can find their lanes, know who they are, their strengths and weaknesses. Appreciate their place in the world, appreciate the relationships they have, nurture those.

It’s maybe a lot to ask. Much of this takes maturity and a lot of stumbling. But hopefully I can do my part to make more of this more likely. I’m in the middle of a really beautiful book right now, The End of the World, Plan B. There’s a section where he re-interprets the prophesy in Isaiah:

 25 The wolf and the lamb shall feed together, and the lion shall eat straw like the bullock: and dust shall be the serpent’s meat. They shall not hurt nor destroy in all my holy mountain, saith the Lord.

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The author points to this prophecy as a new kind of peace. We’re not all meant to be lions, or oxen, or sheep. We, each of us, are individuals, with individual gifts and perspectives. To achieve real peace in this world, we need to learn to love and appreciate and make peace with our differences. I think the first way to do that, is to make peace with ourselves, our gives, our perspectives. To appreciate what we have and who we are. Once we do that, we can then fit into the larger community.

A third type of peace flows from compassion. It manifests itself as an appreciation of difference. Is there a clearer, simpler definition than this? Peace is a cultivated appreciation of the ways we are different. You and I are not alike. But precisely because we are not, we contribute to each other’s well being.

The fulness of the Plan B paradigm, which requires us to push through sorrow to discover compassion, eventually brings us to this third kind of peace. Beyond the reflex for retreat and isolation, beyond the demand for uniformity, beyond the call for justice, comes an expanded capacity to appreciate difference, including the ways each of us is different from all others. This third type of peace is revolutionary without being violent. It is ancient without being old. It is new without being modern.

This is what I want for myself, of course. But I hope my children can find this kind of peace much quicker, much faster than I’m able to, as I’m still working on it.