Category Archives: friendship

The Fatal Flaw of High School Romance

My memory of dating in high school is as fuzzy as my memory of BASIC code, the computing language they taught back then. So as a way to reconnect with lost neural pathways, I combined them: my memory of high school dating, expressed in BASIC.

    • 10 INPUT “Is someone showing interest in me? “; A$
    • 20 IF A$ = “Y” OR A$ = “y” THEN GOTO 40
    • 30 IF A$ =  “N” OR A$ =  “n” THEN GOTO 120
    • 40 PRINT  “Commence awkward flirting and date at Bruce Willis / Tom Hanks movie and/or mini golf.  “; U$
    • 50 INPUT “She’s amazing. She reminds me of [insert movie star] and I am smitten. Does she still like me? “; A$
    • 60 IF A$ = “Y” OR A$ = “y” THEN GOTO 80
    • 70 IF A$ =  “N” OR A$ =  “n” THEN GOTO 140
    • 80 INPUT  “Has two months time passed yet [emotional ceiling reached and/or unnecessary drama unfolding]? “; U$
    • 90 IF A$ = “Y” OR A$ = “y” THEN GOTO 110
    • 100 IF A$ =  “N” OR A$ =  “n” THEN GOTO 40
    • 110 PRINT  “It’s me. Not you. Good bye.’ “; U$
    • 120 END

According to the folks who study brains, the prefrontal cortex, which controls our executive function and rational brain, isn’t fully developed until age 25. Teenagers are still working primarily through their amygdala, which is an almond-shaped, primitive fear-alarm buried in your brain – your emotional lizard-wiring.

It’s science. Teenagers are nuts.

In my case, high school love consisted of a week of blind infatuation followed by a month of confusing interactions, followed by a desire to move on but not knowing how. I never understood my mates and they didn’t understand why I chose to live in a turtle shell of emotional avoidance.

And it wasn’t just me. Everyone in high school had their own soap operas: from “I can’t let my partner out of my sight” to “my identity is wrapped up in my mate” to “I’m too good for any one person.”

It doesn’t help that kids in this country are raised on a “happily ever after” Disney diet of perfect relationships: find “the one” or suffer a life of misery. In my experience, the only Disney connection to actual life is that evil mustaches are awesome.

We learn the hard way that happiness with, and knowledge of, ourselves precedes happiness with another. But we also learn that self-love is an elusive beast.

Do you remember The Missing Piece by Shel Silverstein? And its sequel, The Missing Piece Meets the Big O?  I used to read them to you on my lap when you were five.

“Oh I’m lookin’ for my missin’ piece
I’m lookin’ for my missin’ piece
Hi-dee-ho, here I go,
Lookin’ for my missin’ piece.”

A key idea was that we are never “completed” by another, and that attempts at that goal are misguided. We shouldn’t try to check the box on “happily ever after,” but instead accept that humans will always want more – that it’s the journey that makes us feel alive, not the condition of being whole.

What we need are partners in growth.

But in high school, our needs for acceptance are so strong, we tend to see our mate only in relation to ourselves, and we can construct an image instead of seeing the the raw material. That, coupled with the emotional, amygdala stew surrounding the relationships make them wildly challenging. 

I say chill and enjoy the ride….to the extent possible, of course. 

Appreciate people for who they are inside and demand the same in return. Have long conversations in diners about life, hypocrisy, big ideas and the tortures and wonders of love. Instead of trying to find “the one,” let high school serve as the rich backdrop for your mind, body and soul congealing into its early adult substance.

That said, it’s okay to ride the wave of teenage love: the big feelings and drama and dopamine hits that cause judgment to fly out the window. That’s also part of the growth. And frankly, feelings of love will happen to you whether you want it or not.

Just recognize love’s messiness and have friends to catch your fall when relationships end. And do the same for them. The demise of relationships are not a reflection of you, but the necessary sandpaper of life. It’s the growth happening.

And as you get older?

Your prefrontal cortex will strengthen. I met your Mom at 25. (Or, to be clear, I was 24 and rounded up to 25 when I first met her because it sounded older.)

At that point, you know yourself better. And you can make smarter decisions on mates. And maybe, just maybe, you find someone whose strengths, flaws and quirks you find fascinating; someone who makes grocery shopping awesome.  

I believe that great relationships are driven by the “big conversation” – a long, interesting dialogue woven through life, where mutual growth explodes like a new planet being terraformed. Where mutual individuation is the core, not completing something missing in us. Where we roll together into the future…

“I think you are the one I have been waiting for,” said the missing piece. “Maybe I am your missing piece.”

“But I am not missing a piece,” said the Big O. “There is no place you would fit.”

“That is too bad,” said the missing piece. “I was hoping that perhaps I could roll with you…”

“You cannot roll with me,” said the Big O, “but perhaps you can roll by yourself.”

So enjoy, explore, ride the wave, and learn to roll by yourself alongside others. High school romances are ephemeral, but the love for yourself will never go away if you tend to it.

120 END

How to Make Real Change

I remember going to a party when you were four, and we met a guy who worked on Wallace and Gromit. Among many other things, he made the motorcycle and the helicopter.

And that Blew. Your. Mind.

Till that point, W&G was a magical landscape that existed outside of our world. Suddenly the curtain was pulled back and you were with the gatekeeper.

Me: “This is the guy who makes the magic.”

You: “You made the motorcycle?”

Him: “Well, with other people.”  

You: “You can make magic with other people?”

And like that, you were on board.


“Making magic with other people” is still a line I love. That’s what this is about.

A Startup Story

Last summer I was bored. I had just sold the startup I was working on (not a winner) and was reacquainting myself with loneliness, frustration and malaise while figuring out what to do next.  

Even my fitness regimen was the equivalent of Saltines and water. The same old workouts and no community.

So I decided to change it up – if I couldn’t figure out my whole life pie at one time, at least I could start on the health slice. And maybe help some other folks along the way.

To start with, my weight had been the same since high school. That’s a good thing for most people, but I was a meathead as a teenager, so had more pounds than I needed for trail running, emails and parenting. I had done many diets, but always went back to my “zone” like a Weeble Wobble (toy from my childhood – look it up and be thankful you are in your generation).

Fitness apps didn’t cut it. Some people may meditate or jump rope when a bot tells them to do, but not me. I love you Siri, but I need people.

So I created a little company with a friend. The idea was an online community where teams of 7-10 people would commit to their goals, log their fitness data, get support from their group and have a high end coach to answer questions and send workouts. As one of the guys said: “Workout nerds keeping each other on track.”

And it worked. Actually, it exploded. The conversations were rich and plentiful, and the changes people went through were impressive. These mini-support groups tapped into the human need to belong. It was a tribe. It was accountability.  

I lost the extra weight and kept it off, changed my diet, did my first triathlon, experimented with workouts, and even curbed my wine intake. Now they’re convincing me to dunk a basketball (or whatever sized ball I can pull off).

It wasn’t “fixing my life” but it was changing a big part of it. And it served as a reminder that it’s no good to be lonely in our struggles.  

The startup has since been incorporated into a larger startup, with more experienced hands guiding it. I’m still a participant, and was happy to see it leave the nest. Karma.

My Point? 

Accountability works. Tribe works. We can make magic with other people.

So when we decided a few weeks ago that we would help each other stay on track towards our mutual goals, I lit up. Not only is this a way to for us to stay bonded while you’re gone, but knowing you’re on the other end of my commitments is more motivation than I could ever hope for. Even if we can’t talk that frequently.

I know your aspirations are about getting home soon (clearly a goal I support). For me, it’s about finding community and purpose again. I know, I’m a broken record about these things. But it’s a lifelong journey and what matters to me now is different than even five years ago. And now having you involved puts gas on the fire to get moving.

I want to be at at my best when I’m around you. And working through my own problems is my version of “putting my oxygen mask on first.” I’m a better father if I’m living a rich and full life. But I also don’t want to hide my journey from you. I would rather you be involved.

Teammates keep us headed in the right direction, distract us from the negative voices, help us navigate, and keep us honest along the way. And hopefully we enjoy the ride a lot more.

Even though I can’t be there, I’ll always be part of your team. I’ll be like Wallace in the sidecar of your aspirations, complete with goggles and leather helmet. Off to make magic.

Letters to Ellie: The Power of Canned Spam

In my continuing series of letters to my daughter, who is away for awhile, some thoughts about why humor is vital to a good life.

I was a class clown when I was your age (12). From cartoon impressions to soap opera soliloquies to Three Stooges slapstick, I prioritized laughs over academics. Getting laughs made me feel like I belonged and could other people happy.  

I prayed early on to the comedic gods through Steve Martin and Monty Python records. The other kids weren’t really exposed to English comedy, so they just assumed I was obsessed with Spam. 

silly walk

It irritated the teachers to no end, especially since they got used to my sister’s straight-A ways before me (“Are you sure you’re Kristin’s brother?”). 

It may have been due to my parents getting divorced early on and my home life getting messy. It’s a widely-held belief that comedians all have troubled childhoods (just try Googling it), but this was the 70’s and 80’s and divorce-driven latch-key lifestyles for kids were rampant. So in theory, the whole class should have been an ensemble improv sketch. 

Whether or not I was trying to make up for a difficult home life, making people laugh stuck with me. I was never a genius at it, but learned early on how well life flows when information exchange is wrapped in comedy. Like those peanut butter pill pockets you give to dogs. 

It can go too far, and many people use humor as an escape or coping mechanism. That’s why humor shouldn’t lead the way but play a supporting role. Just look at John Stewart or John Oliver. They have been changing the world by delivering news in a comedy pill pocket. The news is what’s important, but the delivery leads to smiles, not furrowed brows. 

Having run companies, I’ve seen how cultures can develop through humor, assuming of course that the organization is succeeding. No amount of pizza parties, “mixers” or joke emails are going to create a good culture when you’re not doing well. But if that company is succeeding AND has a wit and wisdom that surrounds its work, amazing things happen. People feel connected to something that opens up a part of them that hasn’t come out before. Everyone feels in on the joke and will do anything they can to help the company stay on top. 

I’ve been thinking a lot about this topic because, in times like this, humor can be hard to access. I certainly has been for me. The wind is out of my sails and I’m missing one of my favorite riffing partner (hint: you). 

But all the more reason to seek out those people who can help add a silver lining by being our partners in laughter. People who not only get your humor, but improve it, who make you laugh, who make you love yourself when you’re with them. The people who understand the power of “Yes, and…” That’s when life is great.  

If you can’t find them right now, that’s okay. It’s just a flesh wound. I’ll send you a coconut. 

Letters to Ellie: Being Real

The outpouring of support I got from my last post on my daughter going away to an RTC floored me. Friends from every phase of life offering love, reflection and empathy. A reminder that the connected era isn’t all bad.

What it also did was open up even more stories – heartbreaking but all-too-real situations that my friends are dealing with every day: death, divorce, mental illness, learning disabilities. And a common theme of feeling alone.


It’s not easy being a remote parent, but one of the channels for me is that I get to send letters to Ellie every day during the week. While a lot of the content is light or focused on specific areas of her interest, I also try to infuse them with what I’ve learned in my first half of life. And on the heels of that experience of reconnecting with people, I covered the topic of real conversations in one of my recent notes to her, part of which is snipped out below. 

Enjoy. And thanks for the inspiration.

One of the things that’s top of mind for me right now is real conversations. It’s one of the reasons your Mom and I are together. We both want authenticity in our life and relationships. We crave it. 

And the shorter life gets, the less patience I have for “empty calorie” conversations. 

Just to be clear, I’m not saying “I don’t do small talk.” That would be even more insufferable than publishing my blog. Light conversation serves a valuable purpose: it’s conversational warm-up and an easy way to hang with people you’re just meeting. And it’s great while doing other activities. I’m not going to wax philosophical with other parents while waiting for the bus.  

I’m talking about when long conversations and social events never get past (in my case) microbrews, vacations, workouts, humble-work-brags, remodels, and kids sports; and (in your case) Kardashians, Taylor Swift, apps and whatever else is being meme-d about these days. 

I’ve always sought out real interaction, but often forget in the course of daily life as ego and busyness get in the way. However, when I published the blog post, the response I got was amazing. It drove home how little we share what’s really going on, and how much time is spent on the useless wallpaper of life. 

If those interactions aren’t paying the bills, helping others or making me happy, what’s the point? And why is it so hard to maintain the authenticity in our lives? Do we need difficult times to make authenticity happen or can we keep it up in good and bad times? 

I was going to events because I was supposed to, because they would stroke my ego, or because I just needed to be social. It may have felt good in the moment, but only made me more disappointed in myself as I sold myself out. And I was other people’s empty calories because I was doing the same thing. 

So like other times in my life, I have become a calendar sculptor: chopping off people and items that don’t pass the filter, and seeking out the environments where I feel I can be myself and others respond accordingly. 

I known you’ve felt similarly about some of your friends – that they can be stuck in superficial territory. I think it’s okay to have friends like that, but you need to be careful. In some cases, it may just take awhile for them to open up. Or they may have different expectations of how much to share. Life teaches a lot of people not to share. It’s scary and you can get hurt easily. But we need to keep trying. 

So keep looking for your deep-peeps. And be bold in opening up with who you are inside. Not being yourself around your friends and family takes it toll as we have nowhere else to turn but inward with the built up emotions. That leads to a fun mix of aggression, repression, addiction, depression and more. And the more you open up, the more you’ll realize they’re probably struggling with a lot of the same things. 

I know you know a lot of this already. You’ve got a very good intuition in this area. But wanted to share my thoughts as it’s something I would love to have told my neurotic 12-year old self.