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.
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.
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.
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.
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.
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.
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).
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
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.
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.
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.
I did not watch the Super Bowl this year.
While the rest of the country was fixated on Payton, Cam and Beyonce, I watched Doctor Who battle weeping angels and robots with my 12-year old daughter. It was her last weekend at home before going to a residential treatment center in Utah for a few years, and I wanted to squeeze in as much time as I could with her.
Agreeing to send my 12-year old girl to an RTC is the hardest thing I’ve had to do as a parent, maybe the hardest thing in life. It kicked off a month of grieving leading up to a final, explosively sad good-bye.
I won’t go into the details of her diagnosis or what got to this point. But trust me when I say we had tried everything to keep her here with us. Her needs had gone beyond local resources. This was the best and only option, but one we had faith would help her. We can give her a loving, safe home, but not the level of therapy, training and community she needs.
The night before she left I slept in her room with her, both to keep her safe and because I wanted to breathe in as much of her as I could. I only slept a couple hours, but I was with her. My last night with her as a child that I could protect.
On her final day, we went for our last walk together, a daily practice we had gotten into over the last few months. We can either go in the direction of the park or downtown. Downtown meant seeing people I knew, so I opted for the park. I pushed her on the same swing I had pushed her on as a kindergartner. I only got a couple swings in before breaking down.
I had forgotten how physical grief was. I feel like I’ve aged seven years over this period. Nobody died – getting the help she needs is overall a positive thing – but I feel drained of life energy.
But throughout this painful process, something unexpected happened: by telling the story, I have had amazing connections with people.
Most of the time, we suffer through crappy life events alone. I’m a big believer of the phrase, “Everyone is fighting a battle you don’t understand.”
But when you crack the seal on what’s really going on, people often respond in kind. I was received with heaping gobs of support and people’s own stories of their childhood or struggles with their kids. I would watch people I barely knew shed the “everything is great, just check out my Facebook pictures” masks of daily life in a matter of seconds.
We have a big hole in our house now. A giant loss of energy that I try to fill in with reading her favorite books (Hitchhikers Guide to the Galaxy), writing long email notes to her and taking care of her snake, Neo (who got out shortly after she left, and I thankfully found him in a carpet fold after a few days).
But I am finding solace in our social fabric for the first time in awhile. People I had written off as superficial have transformed in front of my eyes. And I’m learning their backstories and why they are who they are in the world. It’s unfortunate that it takes these life events for it to happen, but I’ll take it.
I’m counting the days till we can visit her in April. In the meantime, you’ll find me on the Dr. Who fan sites.
And thanks for all the support.
Finding purpose in your work is not nearly as easy as commencement addresses would have you believe.
For me, it used to be the bed test: Do I jump out of bed to get after it? And do I go to bed bone-tired but satisfied from doing it? Or would I rather be selling mattresses?
But meaning gets deeper yet fuzzier in middle age, when competence gives way to significance in our priority list, and we wander around asking big, vague questions like, ‘Is this the life I wanted?’ and ‘Am I really going to bed at 9pm’?
Why is “the why” so important?
Viktor Frankl answered that question pretty clearly (and before him Nietzsche) in Man’s Search for Meaning where he recounts life as a prisoner in a German concentration camp and how having meaning was the best chance at survival. He then covers his method of psychology (Logotherapy) that revolves around purpose.
This is the bible of why we need a ‘why’ and one of my favorite books. It’s also one of the best “you think your life is tough?” reality checks to read while you scarf down your latte and gluten-free muffin.
“For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s personal dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself.” – Viktor Frankl
But damn, that’s hard to find. And stressful if we don’t find it, especially with all the pithy online inspirationoise telling us to follow our dreams.
Providing for one’s family is enough for a while, but at some point it’s not just about a paycheck when there are other opportunities to meet our basic needs.
I’m aware that ‘professional purpose’ is not a problem that plagues farmers in Nepal. They know their why. But our country is obsessed with it. And with good reason. Without purpose, as Frankl wrote, we get depressed, addicted and aggressive. Our inner lives become a zoo with open cages.
Last time, I tried to hack purpose by pledging half the money I made towards causes I cared about. That helped, but turned out to be too peripheral if I didn’t enjoy the daily grind.
This time, I’m jumping into stuff I love (“following my curiosity” as Elizabeth Gilbert TED’ed about) and hoping it ends up in purpose. And if not, at least I’ll enjoy the ride.
Perhaps purpose is always there, but gets drowned out by all of the useless voices in my head. Instead of being my co-passenger in a nimble sports car, purpose has been quietly reading a book in the back of a school bus full of obnoxious kids.
I’m still a work in progress, but I’m picking up a few things.
I feel closer to my purpose when…
- I get past my own whiny crap (I save that for this blog) and help others. It’s a Hallmark-worthy sentiment, but it’s true.
- I have a healthy mix of childlike joy, where I lose hours without noticing, and adult responsibility where I feel like a part of the tribe. I’m like that triumphant-faced dog going for a walk while carrying his leash in his mouth.
- I give up trying to cure cancer. I can make a valuable impact on people’s lives doing what I love and being a good person while doing it.
- I don’t worry about what others think. This is an easy thing for me to list as a self-help bullet, but profoundly difficult work. Will dig in here in a later blog.
- I crave the results. Yes, the journey is the destination, but without a fierce desire for the endgame, the work doesn’t feel as vital.
- I am surrounded by people who give me energy, who push me and make me laugh. It makes the ditch-digging parts okay.
- I just start doing stuff. The “What Color is Your Parachute” tests are interesting, but jumping in and doing the work is more enlightening.
Well, it’s not like Indiana Jones using his staff to find out where to dig. It’s more like a kid discovering a big, open playground near his house. By opening myself up to curiosity, I found a bunch of new places to play for awhile – “life experiments.”
Just breathe. Start small. Follow my gut. Find good people.
And then occasionally I step back from it all.
And I’m reminded that maybe I’m relying too much on my professional life for purpose. Like a lot of Americans, I’ve been consumed with one section of a jigsaw puzzle that is much larger than I imagined.
As Frankl writes, we also find purpose in the love we have for others and in how we give meaning to our suffering.
I love my work, but maybe the process of finding purpose there is what leads us to other parts of that puzzle that we never would have discovered.
And that’s all good work.
Mosquitoes were feasting on us. Dusk was flirting. We were sweaty, hungry and ready to call it quits. When we started the hike early that afternoon it was all laughter and TV theme songs. But spirits had since declined to murderous looks and mumbled obscenities.
Sophomore year in college I did an Outward Bound course in the Everglades. And halfway through the 22-day program of canoeing through alligators and bumping into manatees, our teachers left us to navigate eight treacherous backpacking miles from a pristine beach to a remote, decommissioned airstrip – the only flat, dry place on the island to camp – using plastic compasses and bandanas on sticks. Not an easy task. Kind of like hitting a three-pointer from the stands.
It was clear we were lost. Our newly-minted orienteering skills weren’t up to snuff. I wanted to go back to the beach and eat gorp.
Going through life transitions feels like that: a long, uncertain slog that doesn’t seem to go anywhere. Going back to the safety of the known is tempting.
I’m in that transition stage again. And it’s as hard as I remember.
I know I need a change. But getting to the “new you” means navigating through a dark forest full of fear, doubt, identity issues, practical and financial considerations, and the gravitational pull of your old life. And there’s not even a plastic compass.
In short, limbo sucks.
Big life changes come slowly (midlife, kids growing up) or hit you like a gut-punch (getting fired, losing a loved one). Or you could just be cleaning your gutters when some inner-voice tells you your life isn’t working.
There’s a great book called Transitions by William Bridges that describes the process of life changes. I’m over-simplifying, but the basic model is:
- Death of the old self: Often after an incident (good or bad), we are forced through the emotional train ride of letting go of the old life/self/ideas.
- Neutral Zone (the creative stage): The limbo state where we lick our wounds and ask what the hell just happened while slowly understanding our new potential.
- Rebirth of the new self: Sometimes without even noticing, our new life takes shape with new energy and focus.
The big challenge for most people is getting stuck in this middle stage. We get scared and want to go back to the known – our pretty little beach with snacks. Limbo means loss of identity, and that’s frightening. If we’re not that person anymore, who are we? Just a ghost in a void. (And if you’re like me, an annoyingly chatty ghost who talks about the struggle with anyone who will listen.)
So we retreat to our old selves in an effort to belong and be on familiar ground again. “This identity worked for me before, so I’m sure it will again.”
It’s why our country loves plastic surgery and trophy spouses – we can’t seem to stop trying to be 27. But that identity no longer serves the same purpose and mostly leads to more pain, and 45-year old men dressing like extras from Jersey Shore.
Doing this last startup was “grasping for the old me” – it was the comfortable enterprise-software-CEO identity, and the team was even in Portland. I got halfway into the Neutral Zone, got scared, and jumped back under the warm blankets of old Dave.
Problem was, that identity isn’t me anymore. I’m still entrepreneurial, but where I get my energy from has changed dramatically, and being in a different location from the team was terrible. Plus, I no longer own khakis.
I don’t regret it though. I had to do something. And I felt what it was to go back to the old. The important thing was to keep moving. Stasis was much more painful. It’s why I now have a (for some reason 80’s-styled) plaque in my office that says, “Keep Making Decisions.”
It was also important to be open. It’s like that joke about the guy who is looking for his lost keys under a random streetlight he’s never been to because there’s more light there. I was looking for clues in the wrong spot. When I removed those limited assumptions, it became more of a scenic hike with panoramic views and no tourists with selfie sticks.
Speaking of hiking, back to my 19-year old self….
After another hour of drudgery, it was my turn up front with a bandana on a stick to mark the sight line. At that point, I was looking longingly at tree branches as potential beds.
I finally got about 75 yards ahead of the group and stopped to mark the line. In order to get my placement though, I had to move out of the way of a man-made sign that read (I kid you not), “Please Stay Off the Runway”.
I was so tired and convinced we were lost, I wrote off the sign as random human detritus in the forest. I was literally standing on the runway but couldn’t accept it. I read what the sign said to the group because I thought it was funny and they exploded with high fives and hugs. I was confused for a good 90 seconds until it finally dawned on me that we might actually have made it.
Going through a transition again, it’s clear that life is a lot more tasty when I embrace the process fully – to get past the fear and love limbo, to go from bashing myself in the head to enjoying my own company, being open to whatever and to just keep going.
Not only is the destination worth it, but it turns out the hike is pretty sweet if you can keep singing. And you can leave the khakis at home.
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.