Category Archives: Uncategorized

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

On Turning a Life Around. And Companies.

I had lunch last week with a guy named Kenyatta Leal. I met Kenyatta through the Last Mile program, which teaches incarcerated men to code software and, in the process, prepare them for “reentry” with skills, confidence, purpose and community.

Kenyatta was one of the first prisoners to go through the program at San Quentin. After a difficult childhood, he got into drugs and committed a crime for which he was sentenced to life in prison.

Kenyatta is now released, working for a Silicon Valley company, and is one of the most purpose-driven people I have met, especially when it comes to helping other prisoners.

Our sandwiches went untouched as we got lost in the conversation about turnarounds: what makes someone decide to turn their life around?

For Kenyatta, it wasn’t one big epiphany, but a collection of experiences that added up to a change in mindset, including…

  • Listening to counselors who urged him to take responsibility for his actions instead of blaming others;
  • Receiving the “tough love” letter from his mother while he was in solitary confinement telling him that if he wanted to get out, to start acting like it and stop complaining;
  • Realizing his Grandmother’s adage that we’re a composite of our five closest connections; thus prompting him to end his relationship with toxic friends;
  • Agreeing to become a founding member of the Last Mile program;
  • Sharing his experiences with others on a similar path.

Nothing hits the gut more than stories of turnaround, from Les Miserables to It’s a Wonderful Life to Robert Downey Jr. And that whole Jesus “rebirth” story seems to be pretty popular.

I believe it’s core to our programming as a species, not just the domain of self-obsessed Americans. We all benefit when members of the tribe are healthy and contributing. We find joy in the joy of others. So we celebrate their return to health.

I’ve had a number of friends who dismantled their lives through drugs and alcohol – anesthetizing to relieve pain and loneliness.

But some of them managed to reestablish their lives. One guy literally dug himself out of a ditch to go get help.

Seeing people overcome addiction is a testament to what we’re capable of as human beings.

We all have egoic baggage that drives us to do dumb things – inner pain mixed with circumstance that drives isolation and poor decisions. Otherwise we wouldn’t have to worry about turnarounds.

Thankfully, righting the ship is possible. But certain elements must be in place:

  1. Family and friends who care about our long term fulfillment.
  2. Awareness of our destructive tendencies and the likely result of that path.
  3. Mentors and advisors who shed light on the enlightened journey.
  4. A reason why (we must take the harder road).

Watching you and your own turnaround over the last 14 months has been nothing short of amazing. It’s hard to put into words on a public blog, so I’ll do an interpretive puppet show later.

Needless to say, your work has inspired my own turnaround – from “can’t find my way” drifting back into purpose. And perhaps by fate, my purpose has come full circle into this very idea of the turnaround.

In my professional life, I started working with companies on their death bed. I realized how much human potential is trapped in failing organizations – people with hopes and dreams who have been sucked into the machinery.

I learned that I love taking what no one else wants and breathing life into it. Like the prisoners. Working on the island of misfit companies is decidedly unsexy, but I find immense pleasure in moving an organization towards purpose and health.

Through all of this work and conversations with great people like Kenyatta, I have realized that our darkest moments are often a sign that things are about to change.  And that leaves us open to a catalyzing event, like a mother’s “tough love” letter or a daughter going away.

We then hopefully realize that the ingredients for turnaround are already in place. And we have no choice but to act. And through blood, sweat and tears, we turn it around.

And then we fall down again. We never check the box on being “fixed.” But the more we pick ourselves up, the stronger those muscles become, and the easier it becomes. And the more empathetic we are to others going through dark times.

You helped do that for me.

So thank you.

The Most Important Skill

When I was in 8th Grade (your age), I was voted “Loudest and Most Talkative.” I was what one of my favorite teachers called a “Sender” and not a “Receiver” – a one-way freight train of attention-craving prattle.

I was not a naturally good listener. Whether it was in class, meeting people, talking with friends, or even playing sports.

I remember in high school getting on a teammate’s case because he wasn’t staying to work out after practice. For weeks I lectured and guilt-tripped him about it. Then at one point one of his friends pulled me aside and said, “Dude, his Mom is really sick. He needs to help her out.”

As I aged, it dawned on me how much time I spent talking or waiting to talk. I thought I was being a good friend, but I was usually focused on me. Example:

Person 1: “I had a rough weekend. My ferret died. We had to put him down.”

Me: “Yeah, we had to do that last year with our Chinchilla. It sucked. It all started when he caught a flu from our budgie….”

My Listening Stare.
My Listening Stare.

Adults do this all the time. We think we’re empathizing by sharing a related story or experience. But usually we’re redirecting the focus to ourselves without realizing it. Conversations become a mutual rush to share, like two vacuum cleaners going after the same Cheeto.

What changed for me? Two things: one was being on the other side. When I was struggling and my confessions to friends were met with redirections, quick fixes, personal anecdotes and just being blown off, I got frustrated. Second was meeting your mother, who is hands-down one of the best listeners I have ever met. A renaissance receiver.

So I started learning how to be a great listener – to turn my weakness into a strength.

It was quite the rehab, but I slowly transformed. I became a better listener. In addition to the comically intense stare I developed to support my new habit, something surprising happened: I started growing genuinely curious. Not only was I building deeper relationships and making people feel heard, I was enjoying learning about them.

I realized there is a Shakespearean epic playing out inside every person (though some are more like Michael Bay movies in their emotional nuance). And if we can get past our own stories for a moment, we can interact with these living, breathing sagas.

And by bearing witness at a deep level, people light up before our eyes. Nothing draws people to you more than fully, genuinely taking in their experience.

To be clear, it’s fine to share your own stories – it would be strange not to have a good back and forth with friends. What matters is having a genuine curiosity in others, and building the listening skills to get their stories out. As Voltaire said, “Judge someone by their questions, not their answers.”

To me, a good marriage is based on this same ability: having a deep curiosity in your mate’s experience of life and the skills and compassion to bring it out. In focusing on the “other” and supporting his or her growth, we connect with ourselves in a surprisingly profound way and are capable of being together over the long run.

I later learned that Nietzsche expressed the same idea in Human, All too Human:

“Marriage as a long conversation. – When marrying you should ask yourself this question: do you believe you are going to enjoy talking with this person into your old age? Everything else in a marriage is transitory, but most of the time that you’re together will be devoted to conversation.”

My professional life was also transformed through curiosity and listening, allowing me to develop trust and deep relationships with employees and customers. Sales is a good example: most salespeople just machine-gun their agenda to patient eye-rollers, but the curious receivers relate to their prospects, understand their needs deeply, and are remarkably successful.

Learning to be a listener was like discovering plutonium in my personal development. (Or Ruthefordium or Einsteinium. Or one of the elements that doesn’t melt your face.) But as with anything that isn’t a natural talent, I make a lot of mistakes and must keep up practicing.

I see this skill growing in you every day. The depth of your relationships with friends are a testament to it. Keep following that path and the world will open up for you.

 

Letters to Ellie: The Practice That Matters Most in Life

I saw your letter to future students, where you told them how to handle being at a treatment center:  not dwelling on what was or what could be, but to just be in the present and do good work.

I could not have been more proud of you in that moment (dumb presence joke). You innately deciphered the code to a good life: that we are capable of happiness if we let go of our attachments and feel the grass we’re standing on. 

jumping

They don’t teach this in school, or at least they didn’t when I was a kid. I didn’t even spell presence without a ‘ts’ at the end when I was your age. We were too busy memorizing rocks and battle dates, and meditation was in the realm of carob-chomping, sandal-sporting, Cat Stevens-esque groovykins. Not what you talked about with your football buddies.

Core to this ability is the knowledge that we are a conscious being wrapped in a body and mind. If we were in one of your dystopian sci-fi novels, we would be able to inject our consciousness into different host bodies (Obama, Ryan Gosling, Burmese Pythons).

The body has the thoughts, emotions and cravings that get in the way of freedom and happiness. This is what the Buddhists practice: dealing with suffering. Not denying suffering, but understanding and transcending it. The only thing certain is change, so be at peace with it.

On the one hand, suffering comes from the past telling us who we are (entrepreneur, artist, snake-lover, life of the party). Good and bad memories and patterns become our ego narrative. It’s not that we need to block out fond memories or deny our past – the problem is when our connection to history causes our suffering. Just read my old posts for a not-so-subtle nod to this “who am I?” pain. 

On the other hand, we have “if only” longings for a better future or the pleasures we think will make us happy. “If only I was (thinner, funnier, had my daughter at home, better at summarizing thousands of years of spiritual history in a short blog), life would be better.” 

It’s not that we can’t enjoy the fruit of this life. The problem is when we crave those pleasures at the expense of enjoying the moment.

You’re learning on your own to be aware of these thoughts and feelings – seeing them arise, and then letting them move through us.

Remember in Cincinnati when you, Hazel and me watched the highway looking for cars of a certain color?  Then for some reason, we would tackle each other when that color came through? That seems like a better way to witness our thoughts and emotions coming through us – like cars on a highway. Or as Eckhart Tolle says in The Power of Now, watch them like a cat looking at a mouse hole.

Mindfulness has become a big industry for our oversaturated lives. And that’s a good thing. Western culture rewards bigger/better/louder, especially with a big megaphone for the whole planet to shout into. To deal with the cacophonous reminders that we’re not good enough, people need meditation in the workplace, books, internet gurus. I’m glad we’re getting it, but it took crisis mode to get us here.

As a kid now, it must be incredibly hard, especially in your situation. I remember suffering at your age: wanting a girlfriend, wanting to be younger again, wanting to be better looking, popular, funny. Much of the years 12-18 were a mix of unbridled fun mixed with self-torture for what I didn’t have. If I had more practices and teachers back then, I would have saved myself a lot of pain (or is that “if only” thinking?).

Since my 20’s, I have meditated. I’m not enlightened by any means, but I practice. And when things start to suck, I find solace in my slowly-improving abilities to connect with the moment: watching my thoughts, counting breaths, repeating a poem, and life activities like jogging on the mountain, staring at clouds or even eating (poorly) with my non-dominant hand.  

Ultimately this is applause for you. You have intuited something powerful and vital in this always-on, mostly-depressed world; something that spiritual teachers have been preaching for thousands of years: instead of running off to the woods, we can have a uniquely human utopia inside ourselves with practice.

You are choosing to be happy, one of the most important and hardest decisions we make as humans. And that is more than I could ever hope for you.

Letters to Ellie: The Biggest Predictor of Success? We all have it.

I’m still energized from a visit to see Ellie last weekend. This letter came out of discussions around having a goal and a roadmap to keep the faith during difficult times. I hope you enjoy.


A lot has been written about grit lately, the courage and resolve to keep going despite challenges and setbacks. The ability to run marathons instead of sprints. 

A TED talk a few years back by Angela Duckworth (and now a book) claimed that grit was the best predictor of success in kids, not talent or intelligence. Since then it’s become a bigger meme for the TED-regurgitating smugsters. But with good reason – the evidence showed pretty conclusively that kids who persevere go on to do big things and are happier as a result. 

I agree wholeheartedly. But in my experience, a lot of us have grit. Perhaps all of us. It’s not a binary condition that some kids have and some don’t, like being a Belieber. I think it’s more like a reserve gas tank that we all have, but only opens when the purpose switch is flipped and we journey through life deliberately. 

a_long_journey_home_-_800x600

For many “successful” people in the world, grit comes from pain. Trying to make whole what was missing for us as kids. Trying to fight that shame gives people access to that reserve tank. Kids get messages like “you’re not good enough,” “you’re not as driven as your sibling,” “you’re different from the rest of the family.” That either winds ‘em up like a toy robot or winds them down into a spiral of self-doubt, sadness, chemicals and an over-reliance on others. 

Maybe pain isn’t the ideal source of purpose, but in my experience it’s okay. It’s the movement that matters. Movement leads to experience, insights and discoveries. A lot of my early motivations were based on vanity and insecurity (now try getting the Simple Minds song from Breakfast Club out of your head). It’s not necessarily a bad thing and comes with the territory at that age. And it ultimately led to a better place. 

For instance, someone may have felt shame as a child for not being smart enough. Instead of burying her feelings, it forced her to study like crazy, graduate and go on to an Ivy League school and highly respected job. To prove herself. 

After four years of working 80-hour weeks, she starts to question why. The only people who question her intelligence now are in her own mind. She imagines herself running a race only to discover there are no competitors or spectators. 

But along the way she traveled great distances, met people, learned how to get things done in the world, and discovered a deep-rooted desire to help others. She leaves her job and starts a nonprofit, now applying that same grit to a different problem. 

Maybe she still has things to prove, but she’s accessing a deeper reserve tank and deeper sense of self, and that will only continue.

I know a lot of people just like that. 

It’s why I got sad a few years back when I lost a sense of purpose outside the family. I no longer knew how to access my tank. I worked on a lot of “stuff,” but didn’t have the reserve power to keep it going. Only upon falling down, did I realize how important it was to work with and help people I loved and respected. Falling down was its own instigator of growth and movement, though it didn’t seem that way at the time. 

Our brains get dopamine hits when we accomplish little things on the way to bigger things. We gain strength and confidence when we work towards goals that matter. I write a lot more blogs now that you are the purpose. You give me access to the reserve tank. 

That’s why I believe strongly in your desire to have a big goal and a roadmap. We’re wired for that. If you have a life where your raison d’etre is constantly known and growing, with large and small goals and the tank to keep working towards them, I would feel like a charmed parent. 

Because eventually, when we have worked through the big “missings” and pain and insecurities, we no longer need a reserve tank at all. Instead we gain access to an infinite energy source, where life is a constant, humming connection to ourselves and others. Like Neo at the end of The Matrix when he could see the Matrix for what it was and no bullets could hit him anymore. 

That’s the beauty of it all: if we channel our pain to propel us forward, we survive, thrive, and eventually find ourselves on an more enlightened plane of existence.

To wrap it up: 

  • We all have grit, including you for SURE. I’ve seen it.
  • We must use our pain and suffering to drive us forward instead of turning inside ourselves and self-destructing. 
  • When we keep moving, we get the dopamine hits along the way and we keep growing and learning. 
  • As we continue to grow, we let go of our selfish dramas and move towards a deeper energy. 

And all of this is stuff I have learn again and again. Rinse and repeat. So don’t be hard on yourself. You’re already way ahead of the game. 

Letters to Ellie: How to Know if You’re a Good Rebel

We got to visit Ellie last month (first time I had seen her in two months), and it was amazing. During one of our conversations, we talked about what it meant to be a good rebel versus a bad rebel. This letter came out of that discussion.

Last night I had a football dream. (I know…sports–groan–but stick with me.) I was playing linebacker on defense and wanted to destroy the other team’s quarterback. I could see his eyes – he was cocky and taunting me. I wanted to take him down. I maneuvered around the backfield looking for the perfect line to blitz.

But another member of my team looked at me, saw what I was doing, and pleaded for me to cover the outside, not attack the quarterback. It was like telling a starving man not to touch the cheeseburger in front of him.

As hungry as I was, I relented and did my job covering the outside. I let the other players blitz, which forced the quarterback to throw an errant pass in my direction. I dove for the interception….

In doing so, my IRL body jolted awake in bed with a racing heartbeat.

But I was psyched – I’m pretty sure I made the interception! Maybe I’ll make All-Dream-League this year.

football

Why is this relevant?

Here’s my topic: when I was your age, I thought I was a rebel. When I felt disrespected or patronized, I would lash out: yelling at refs, coaches, teachers and anyone else who would get in my way. 

Problem was, I wasn’t doing it for what I thought was right for the world. I was doing it for my own selfish interests. For what made me look good.

And I didn’t understand the consequences and collateral damage I was causing. I was alienating myself from friends and creating rifts with adults through my typhoon of rule-breaking, yelling and petty battles.

The desire and ability to stand up to people ultimately served me well. But it took a while to harness it for good.

Part of being a good rebel is to stand for something: to have a belief, a voice and the passion to see it through. From singers to artists to athletes, rebels can reshape our understanding of what can be and cause us to question our assumptions. 

The other part is to work change from within, instead of constantly fighting the power directly. Collaborate with people to get things done. Prince was a rebel. He created groundbreaking music and inspired a generation of musicians. But he also worked for Warner Brothers and Arista music to get his albums out. He chose his battles on the dance floor.

“It’s not wise to violate rules until you know how to observe them.” – T.S. Eliot

What finally changed it for me was football: working with coaches and players I respected and giving myself fully to a larger goal than my own selfish desires. I didn’t agree with everything, but I played by the rules because I believed in it. And once I was a part of it, I could influence change from within. Trying to change from the outside is like trying to force political change in a country without speaking the language.

And those are some of my happiest moments: being a source of strength for other people on a good, shared mission, one that’s bigger than any of us.

I know you’ll have the same moments. You’re a natural leader, a strong voice, and a great rebel.

Letters to Ellie: What I Would Change About My Younger Years

Another life-lesson excerpt from my letters to my daughter. We finally got to see her a few weekends ago for the first time in two months. Amazing.

When I was your age (12) I got into martial arts. I mean, really into it. Karate Kid had just come out, and tae kwon do studios were everywhere. I wore kung fu shoes to school, memorized the Bruce Lee movies, practiced moves on unsuspecting kids at recess, and even referred to myself as The Master (sigh). 

Bruce

Lots of seventh graders have identity issues but I was a one-kid carnival show. Karate-guy was just one of many, in between breakdancer (complete with peroxided ducktail), skate punk, survivalist and weightlifter. Probably a rodeo clown and beatboxer in there too. 

I wanted to be respected, included, loved. And if I didn’t get that love, I would go all kung fu on myself. I had the shame of not being good enough, so struggled epically to earn people’s respect and to have them as friends. I just didn’t know how to do it. So it usually backfired as I willed these ridiculous characters into existence. 

As a younger adult, that fierce desire to fit in was still there. No more ducktail or nunchucks, but I still hungered for the drug of outside validation. 

This led to insufferable traits: boasting, raging and, perhaps most destructive, assuming the personality I thought would impress people, aka the “chameleon.” 

For business people, I would channel Richard Branson; for spiritual folks, Alan Watt; for hipsters, the guy into artisanal pickles and rare records. I could be anybody I thought they would like. One time I caught myself acting like someone into auto racing. As you well know, nothing could be further from my natural interest map than NASCAR.  

Most people work hard to look good socially, but stay true to their feelings. The chameleon will shape-shift for anybody and any situation. An indiscriminate Gumby selling out their feelings for inclusion. 

Awareness of the problem is a big step. But I would still find myself swept up into social situations without seeing it happen and I’d reflect on it later like Dr. Jekyll with a Hyde hangover: “Argh, I did it again, didn’t I?”

The bigger work was understanding why it was so important for me to impress. What happened that created this fierce desire to be admired. And ultimately realizing that my ego will get in the way of my happiness, both by setting a high bar for self-measurement and by making my happiness contingent on others. 

It’s that self-excavation work that helps us enjoy ourselves. Just like in Hollywood, we learn to love the bad guys when we know why they ended up that way. From Gru to Freddy Krueger, the backstory makes them sympathetic. 

So my advice would be to get to know yourself apart from egoic images. Catch yourself when you’re trying to impress and ask why. The more you learn to love your wacky, inner self, warts and all, the more you can let that self lead the way in life. And ironically, the more people will be attracted to you. 

“I’m not in this world to live up to your expectations and you’re not in this world to live up to mine” – Bruce Lee

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.

opendoor

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. 

Why Being a Remote Startup CEO Doesn’t Work: My RipFog Story


I spent the last year trying to incubate a company in Portland from the Bay Area. It didn’t work out. It was not a unicorn (more of a gremlin). But it’s all good. Here’s the story.

Some of you may recall that, out of desperation, I set a timer for myself to start a company. My recent attempts at finding work had failed the passion test. The critical voices in my head were causing me to crack. My brain was like the stoning scene from Monty Python’s Life of Brian.

I wasn’t convinced doing another startup would be ideal, but it was movement. And staying busy is a good hack to keep the demons at bay.

Having grown a company in Portland back in “the naughts,” I knew a lot of really talented people up there. And they were all in the market for something more interesting to work on. My thought was that we could build a product in Portland, and find the people to sell it here in the Bay Area. Ergo, the name RipFog: Rip City (Portland) + Fog City (SF). For 98% people however this become RipFrog, even if they were staring directly at the written name. Apparently frogs are linguistically dominant.

So when one of my old architects from my previous company in Portland had an idea, we jumped on it. It was a brilliant, highly-technical idea, and way out of my sweet spot. But bumbling my way to knowledge was part of the fun. We raised some seed money, hired a small team and went at it – they in a cool office in Portland’s Pearl district, me staring longingly at said office through video conference on a rolling monitor, like a wistful Max Headroom.

I got to know the problem space, then polished up my wingtips to pitch it a hundred different ways to a hundred different potential users. I flew my cofounder down from Portland to the Bay for marathon days of feedback meetings.

Early signs were positive, partly due to it being a new domain. Plus we were talking to friendly folks who tell you what you want to hear. But as we got further into it, we realized it was going to be a tough road. Developers loved it, but they’re notoriously cheap. The people with money didn’t get it: the product wasn’t solving a deep business pain point yet, just a technical one. It’s possible to build a business around developer needs, but not the business I wanted to run.

After five months of building and pitching, we took stock and decided that it wasn’t going to work. Over the holidays in a hotel room in Ashland, OR, I even put together a plan to merge the company into another startup that was starting to get traction.

I thought the merger was a great plan, but the Portland didn’t share my enthusiasm. This was for a Bay Area company so a merger would make them the remote Max Headroom group.

But we still had some cash in the bank and a lot of ideas. So they were keen to take another swing at the plate. I went along with it.

That kicked off a process of ideation and product iteration. I would come up with ideas, meet with experts in the Bay Area to test those ideas, and then fly up to Portland to further refine the concepts with the team so they could prototype.

Ideation is normally a really fun process: whiteboarding big ideas and open space for how you can change the world. But doing that much of it by yourself and/or remotely sucks. You need the collaboration and whiteboard time. My team was amazing and I loved being up in Portland, but it wasn’t feasible to be there full time given my family and Bay Area-native wife.

After four months of grinding my brain, and meeting with anyone I could for idea feedback and frequent trips to the Rose City (maybe we should have been RoseFrog), we finally honed in on an interesting idea that had legs. And we built out an initial product with 20 different companies trying it out. Problem was: we were running low on money.

While I could have raised more money and kept it going, I didn’t want to run it remotely anymore. The team needed direct, collaborative leadership if it was going to succeed, especially in this “figure it out” stage. I was exhausting myself AND doing a bad job.

It’s one thing if the product ideas are coming out of Portland (like the original idea) and I can focus on selling it. But when it’s on my shoulders to bring new ideas for them to go build, it just didn’t work. If we could have been in the same office, it would have been different.

I thought of finding someone in Portland who could lead the team. We talked to a few CEO folks and even had a great candidate lined up. But the team didn’t want someone else. And the new product ideas were getting further away from the engineers’ passions.

So rather than raise more money and keep going down this uncertain road, we decided to find a good home for the company. Sad for me as I loved the team and felt like I let down them down. But it was the best decision.

My big takeaway: it’s okay to be remote if it’s a known category and everyone knows what to build and sell. But for a new idea, you need to be in the same room. That, and stay away from “Fog” in your name.

While not the ideal outcome, it wasn’t a bad one. And we had a good time, met a ton of amazing people, found a great company in Portland to acquire the team and IP. And we didn’t raise a lot of money so we were able to keep our investors chips on the table (i.e. they got equity in the acquiring company).

And those voices in my head? Much quieter now. More like the “Always Look on the Bright Side of Life” scene.

Most importantly, I learned a lot about myself and what makes me happy. The experience has been the catalyst for a few new passion projects. Stay tuned on that.

 

Craftwork: How Building a Dollhouse Made me a Better Boss

I’ve always been jealous of people with hobbies. I aspire to have one, but my overly-linear “does it move the ball forward?” filter for life has held me back from an all consuming passion for baseball cards, stamps or old daggers (seriously–Angelina Jolie collects them).

So I was out of my league when I went to a hobby store a few years back on the hunt for a doll house. My daughter was obsessed with doll houses and wanted a “real one” to be her big Christmas gift.

In a split second decision that would haunt me for the next year, I decided to go with the kit instead of the pre-built house as a “fun project to work on together.”

If you haven’t been through this before, a doll house “kit” is something only the guy from A Beautiful Mind could love: a giant box overflowing with thousands of tiny, unidentifiable, easily misplaced pieces of wood, all of which need to be organized, inventoried, sanded, painted (in a specific order), trimmed and varnished, all before you assemble anything.

Sundays over the next year became a mess of paint, glue, obsession, frustration, and trips to the hobby store, where the kind and crafty older women looked at me like a 5-year old who planned to build a car.

Continue reading at Inc.com.