Supporting Local Restaurants during COVID-19

We went outside as a family the other day, a Saturday. We’d been locked in the house for a week straight, my six sojourns outside our block by far the most in the family, and the kids were driving us crazy. I had a matchbox car hurled at my head the evening before, our three year old finally deciding to give up all pretense of obeisance, and we’d decided we needed to get out of the house. 

That week prior was a whirlwind of emotions and change. The outside world was by degrees falling apart and going to be ok in two weeks, depending on the combination of my mood and whatever input I’d consumed, while the crisis in our household revolved around two issues: (1) the macro, as in how would we as a society with our fearless leader at the helm make the decision between millions of lives lost to disease on one hand and millions of lives lost to poverty on the other hand (so far outside the realm of our control, this topic was easier to discuss objectively because nobody in our house was on the hook for it), and (2) the micro, as in what did we as a company and we as a family need to do to weather the sudden elimination of the American economy.

The micro was harder. At work, our company’s executive team was cycling between developing a new strategic plan for the “new-normal”, starting to implement said plan, and then developing a new plan with the next daily news briefing, while at home Laura and I had cut expenses past the threshold of “comfortable” and into the realm of “possible,” at which point we were able to sustain the idea that we had somehow done enough. So I carried a sense of fragile solidity as I pulled our Chrysler van out of the driveway. I generally felt On Top of Things, even as the world was falling apart. 

We couldn’t go to the bounce house, obviously, and museums, restaurants, retail stores, friends houses and every other place we typically took the kids to kill a weekend morning were also off limits, but Laura had learned that a couple of our favorite restaurants were serving takeout so in the interest of helping out those worst affected by the crisis we had organized the trip around three separate restaurants-come-takeout-joints. Laura and our oldest played eye-spy for most of the drive downtown.

I took a detour down College Avenue, driving by the kids’ closed school before making our way down Monroe, driving alongside the river. Laura told the kids maybe tomorrow, when it was warmer, we’d do one of dad’s favorite things and walk along the river. I used to do that walk almost every day, as our office is (was?) right next to the river.

Even looking for it, it was jarring to see the neon OPEN sign on the door of the bakery, the lights on and a placard outside inviting us to come in. There were even a few people inside. Every other retail window on the block was dark. We pulled up to the curb. I normally parked in a lot off to the side with loosely monitored “residents only” parking signs, but figured given the circumstances who would care? I tossed the keys on the seat behind me to leave the car running while I went inside.

Over a year before, a friend’s mom had died near Christmas. She was in her fifties when she passed, unexpectedly, and they had been close. Shortly after it happened, I remember talking to her and inadvertently mentioning moms in a way that implied everyone at the table had one. It got silent and, realizing what I’d done, I looked over to her. On her face was the kind of raw pain and vulnerability usually reserved for your bedroom pillow, which transitioned by degrees to a sort of defiant resilience, determination and even anger–at the event certainly but also at being suddenly open and vulnerable in public–and then finally into a placid and wistful smile on an otherwise blank face, at which point she said “it’s ok, don’t worry about it.” I watched that specific sequence play out on the faces of the five staff members of the bakery when I walked in the door, at the conclusion of which a woman I’d exchanged pleasantries with during hundreds of previous visits said with her blank face, “Hi Ryan, how are you?” 

I told her I was fine. It was clear we were both more comfortable talking about bread. I bought a loaf of sourdough, and watched her select the loaf from the back shelf with a pastry napkin and inadvertently brush her bare finger on the crust. I pushed it out of my mind. When she returned to the counter I asked also if I might purchase a hundred-dollar gift card. She paused, a complicated flash in her eyes, and then said “thank you, yes you may.” While she got me my gift card, I asked the barista how he was doing. He took a breath and smiled, “we’ve laid off half our staff, but we can survive on 60% sales now so we should be ok,” he said. “At least until they shut us down entirely.” I said something woefully inadequate, took my gift card, and left. 

“I imagine you saw what I did,” I said when I got back in the van, thinking that Laura must have seen the alert for the $106 loaf of bread come across her phone. She nodded. I turned away, heat rushing to my eyes as the boys in back asked if they could have a piece of bread. Laura told them it was for lunch, and then asked me what happened. My explanation couldn’t quite capture what had happened, tears welling under my eyes we pulled away from the curb.  The boys asked for bread again.

After a drive we pulled up to the market. Laura handed me a discarded candy wrapper with which I covered my finger as I pushed the button and took the entrance ticket. We parked right by the door, next to the only other car in the lot, a Prius. The door that went straight to the deli had a sign on it saying it would be indefinitely locked, and to use the main entrance. Thus entering the building down a ways, I walked past rows of empty shelves that used to be a bakery, a bare space on the floor that was a spice store, and a coffee shop which, while deserted, looked like they would be back tomorrow, before reaching the deli, which in comparison looked surprisingly normal. I reviewed the cheeses displayed in front of the counter, and meandered to the wine rack where I immediately saw three bottles of Il Follo displayed, one of which I reached for before I saw the sign politely instructing me to have the staff handle all purchases. Returning to the counter, I asked the man behind the counter to select his favorite snacking cheese and an accompanying salami which, along with the Il Follo, he bagged. He put on blue hospital gloves and asked me for my credit card, apologizing that they didn’t accept Apple Pay (a statement with newfound gravity). I asked about them, how they were doing, considering. “Surprisingly well,” he said with a smile. “Our bar is closed, but the deli has been doing better than we thought.” They were five people in a market staffed with 20 across various stores. I looked around and failed to find another customer. I smiled and said something intended to be encouraging and left.

As we pulled out of the parking lot, delicately inserting the ticket without touching the machine, we decided we would grab a smoothie for the kids from a store we both liked, and swing by a restaurant I frequented for breakfast to pick up a few of the take-out lunches they had posted on Facebook. Laura instructed me to get a single smoothie, split into two cups each half-full in the way of experienced parents. I nodded and smiled. 

We pulled up to the curb and peered at the smoothie store. The lights were out and there was a white paper sign on the door. We sat in silence for a beat, then pulled the van away from the curb to go get lunch, glad the boys apparently hadn’t heard us discussing smoothies. 

After a drive, we pulled up to the restaurant and parked a safe distance from the bus stop that we decided was probably still active. The restaurant had been a landmark of Grand Rapids until its proprietor passed two years prior, after which time it transitioned into a delightful and less obscenely busy restaurant/deli which I much preferred. They had outstanding breakfast, and the servers never blinked at my frequent visits to just order coffee with my laptop (intermittent fasting being a thing I tried intermittently). Anyway, I always tipped as if I’d ordered food. 

That day, I walked into the deli-side and saw my normal server behind the counter. The lights were off in the restaurant-side of the suite, and my usual table by the window was conspicuously bare, like all the others. Tupperware filled half of the shelves in the deli, and raw vegetables had been placed on tables around the perimeter of the room, blocking benches where patrons once sat. I briefly caught the eye of the server before she busied herself with Other Things. I put my phone to my ear and listed the available tupperwares to Laura as she sat with the kids back in the car. She instructed me to get a couple soups, a couple sandwiches, and a pastry that Laura and I had agreed was the best in the city. I hung up, walked over to the server behind the counter, and reported Laura’s order. She grabbed the tupperwares, and with a flat tone apologized that their pastry chef was not in due to “lack of demand.” There were tears in her eyes.

I assured her it was no problem and asked that she pass along my compliments to him when she saw him. “Her,” she said, entering prices for our lunches on the screen. “I’ll tell her.”  Of course, I said.

While typing prices into the screen, she reported that they had laid off most of their staff, and that she expected to be laid off soon. She said the owner (pointing behind her at a bearded man in an apron) was simply going on as normal, but that they all fully expected to be shut down any day by the state government in an effort to curb the spread of the disease. She explained that they were trying to sell off the rest of their ingredients so that things didn’t go to waste when they were forced to close their doors. I purchased another $100 gift card. She thanked me but did not smile.

On our way home that Saturday, as Laura and the kids eye-spied bridges and grass and trees, I kept replaying that encounter, wishing that I would have also bought a cabbage or zucchini, or maybe more tupperware. Or something.

Governor Gretchen Whitmer issued an Executive Order asking all customers to stay home the following Tuesday, socially distancing each of us from each other and confining us to our own problems. Settling in to our new life indoors, managing two kids with tons of energy and a full time job in a confined space, at some point I forgot where I put the gift cards.


If you enjoyed this labor of love, please subscribe, like, share, or let me know your thoughts in the comments. Thanks for reading! — Ryan

When quitting is the logical decision

I went to bed crying about business once, years ago, and I remember feeling like the whole thing was fucked.

We were running out of cash, over 70 employees and their families were counting on me to find more cash, and even though the business was meeting its objectives fundraising was going terribly.

The day before it had been going well, funny enough, before the investor who had spent literally dozens of hours with us pulled out instead of offering a term sheet as he had told us he would. He explained that his partners weren’t as excited about the market as they had been, and the $10m that we had been expecting to close within the next 30 days evaporated when I hung up the phone.

I knew the next step was to open my laptop and get back to work, but it all seemed pointless. We were going to run out of money, I was going to let down everyone that had believed in me, and I personally would be branded a failure and run out of town as a response. I forced myself to look up when Laura got home, and her smile turned to concern when she saw me. We talked, and because she’s amazing she tried to mirror me in such a way that I could see my way out of the situation. She talked through alternative options, bright sides, everything, but I didn’t want to hear it. All our options sucked. We had banked it all on one investor, which I knew was a bad idea but had somehow convinced myself would work, and now it was all going to blow up. Our business was gone, my life was over, and I wanted to crawl into a hole and sleep until I died.

So I went to bed at 6:30pm.


When I woke up, the investor was still a pass. I went through my situation logically, evaluating all the options that we had, and came to the unavoidable conclusion that we still didn’t have any options. I hated that reality, but it was fact. We would run out of money, we would fail, and it would be all my fault.


I’ve found that there are choices and decisions in life, and the two are very different.

Decisions are what you make when you know where you’re going and you’re trying to optimize for the best way to get there. There is a right-est answer, so you evaluate all the data and then make a decision based on that data, trying to steer as close to the correct answer as possible. Choices, on the other hand, are what you make when there is no right answer, you don’t know where you’re supposed to go, there is no available data, or the data contradicts. You don’t evaluate anything in making a choice. You make choices based on gut (said differently: based on nothing), and if someone asked you why, you might be able to spin up some logic in support of that choice, but you’d know it was made up as you said it.


At that moment, sitting in my kitchen with everything telling me to simply pack it in, I made a choice to keep going. All the available data said we were screwed, and I maintain that the correct decision would have been to stop, were I evaluating data. If I had done a pros/cons list the piece of paper would have tipped over due to the weight of ink on the Cons side.

But I chose to keep going.

Three months later we’d secured follow on financing from a new investor just in time, and from that were able to launch the 2.0 version of our product which leads the market today. None of that was possible sitting at my kitchen table looking at the data, but all of it happened because I chose to keep going despite its impossibility. We reached second base not because we knew how to get there and were skilled navigators, but ultimately because we were willing to step off of first base despite having no idea if second base really existed.

Running a business means making thousands of decisions every day. You succeed or fail based partially on your ability to make those decisions with a high degree of accuracy. But running a business also means making at least a handful of choices, and in those moments every successful entrepreneur has consistently made the choice to keep going.

In the words of a mentor of mine, Chelsea FC Avram Grant:

If you persist, you may succeed, or you may not. But if you quit, you ensure you will not succeed.


Update: I went to bed crying about business this week, as COVID-19 shut down the economy. I know a lot of founders who did.

Corona Newswire

My son coughed the other day. It was only one cough, but Laura and I immediately looked at each other. We waited a beat, while he boxed-out his brother from the “Mickey Mouse Clubhouse” made of Magnatiles, but there were no more.

When the shit first hit the fan, I was just getting over a bug, and both our kids had runny noses. I looked it up at the time and that’s “rare” for COVID, but I still thought about it when I wiped their faces with toilet paper.

In between legos and nose wipings I spent most of my time on Twitter those first couple days. I saw a tweet that said:

  • Instagram: My life is a party.
  • Snapchat: My life is a quirky tv show
  • Facebook: My life turned out great!
  • Twitter: We’re all going to die.

and I think it’s true (update: so does Seth Godin), although maybe I’m biased because 50% of my recent experience with Twitter has been during a pandemic. I found myself retweeting things that seemed worth sharing, like people should know about them, and that’s how I, too, became a 21st century doomsday crier. I saw a side-by-side of Trump telling everyone it’s no big deal cases are already going down next to him saying he always knew it was a pandemic next to him assuring people we would win while he clutched a podium with white knuckles. A startup founder sent a link saying millions of people would die in the next three months, and another sent a link to drunk people on Spring Break in Miami. “Fuck the ‘rona,” said those people, probably. Some people posted about people losing their jobs, and some people gave those people money. The whole internet was talking about flattening the curve, but an epidemiologist who for some reason decided to publish on Medium explained that no amount of flattening would prevent hospitals from being entirely overwhelmed. While Wall Street sank into the East River, the internet filled in admirably by shouting partially informed data and instructions at one another. I felt like I was staying up to date. Laura told me to stop talking about it. I couldn’t sleep that night. Someone tweeted:

  • stay home as much as you can
  • i know it sucks but it’s necessary
  • you’ll literally save lives
  • this is the easiest it’s ever been to be a hero
  • just think on it like:
  • 1. soldiers who stormed the beaches at normandy
  • 1A. people who stay home right now and watch Netflix

The next day I remembered that I used to avoid Twitter entirely, and it felt like a good day to revive that practice. I knew enough to stay in my house, and whatever news I would miss by unplugging wouldn’t change that fact. We had a nanny come in to help in the morning, and as she walked in I nonchalantly washed my hands in the sink and mentioned how often we were all washing our hands.

I was productive, which felt amazing. Laura and I officed out of our basement, while the nanny kept our kids busy collecting pinecones at the park (she made the boys wash their hands when they got back). I spun up a new Corona-inspired business model in the morning, and spent the afternoon on phone calls telling people that all we can do is to focus only on what we can control. I knew that was right, and that leaders are forged in the crucible of pandemics, but it still felt forced. Maybe it didn’t matter.

Laura was in good spirits coming back from her first foray out of the house in days. She’d just watched the latest coming out of the White House, and commented that she was impressed by the transparency and competence the doctors showed with Trump leaning over them. They said they’d had challenges but they were taking steps, and they expected we’d get past this. Good news felt good. I called my mom later that night, and she said she felt better about things, too. Yes, hundreds had the virus, maybe thousands by now, but this was the combined ingenuity of the entirety of the American population we were talking about. Even Bezos was involved. We’d get past it, just need to lay low for a while.

After our youngest finally fell asleep Laura joined me in front of our gas fireplace, joking that we’d kicked the ass of day five. Who knows how many more to go, but it felt like a number we’d get through. I checked Twitter, skimming through tweets rapidly. Same old shit, but toned down a bit. People finally felt heard by the government, maybe? Either way the tone seemed to have shifted. I saw someone summarize an Imperial College Study which seemed like legitimate, trustworthy information, which was unique, so I read it.

My eyes glazed over. I felt my heartbeat in my chest. I sat there silently for I don’t know how long, then I put down my phone and sighed. We went upstairs after a time and I slept restlessly.


I woke up at 5am as normal. I ground coffee and made a pourover as normal. I read a bit from a spiritual text as normal, highlighting quotes I liked for a book I’ll write someday. I meditated as normal, and when the chime went off after 40 minutes I checked the NY Times. Because fuck Twitter, that’s why.

The lead article said that China had had its first day with no new local cases. They only needed 13 more consecutive days and they’d have “won,” although I wasn’t sure what that meant, exactly. The photo showed what life looked like in China, city streets empty, gated and guarded. I wondered what it took to win this war, and if we were doing enough.

I worked for 30 minutes and then got the boys up, watered down some apple juice and made them some dry Cinnamon Toast Crunch. It seemed to me that our government effectively had a choice between millions of lives and our economy. There were smart sounding people who talked between and around the President, and China was winning, and I allowed myself to hope that maybe we could actually win this thing. Something close to faith, maybe. Study be damned.

Laura coughed as she reached the bottom of the stairs. Without looking up, I told her I was ignoring that.

I finally grew up enough to read “Fail, Fail Again, Fail Better” by Pema Chodron

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

Samuel Beckett

I was putting away our Christmas lights (finally), when I ran across a book in the storage area of our basement that made me pause and look closer. It’s called “Fail, Fail Again, Fail Better,” by Pema Chodron, with a forward by Seth Godin.

I’ve owned this book for several years, having bought it in a frenzy of Seth Godin consumption, but the spine was still uncracked. It was one of those books that I’d like to HAVE read, but not enough to go through the trouble of reading it. Like learning Spanish. I want to know it, but don’t particularly want to learn it. That was this book.

But this time, looking with different eyes, the book was simply right for me. I had to read it.

I still admire Seth Godin greatly–his is one of the three blogs I subscribe to–but more importantly I’d had the opportunity to read two of Pema Chodron’s books as a part of my re-introduction to myself after leaving the CEO role at VNN. It was her name on the cover that called out to me, to that human and vulnerable part of me that is playing a much greater role in my life these days. Seth’s name then complemented that call, justifying the read with an assurance that I would be better at work for the investment. It was an utter flip flop from when I had first bought the book, funny enough.

FFAFB is for the most part a transcript from a commencement address Pema did at Naropa University in 2014. Between that and “This is Water,” by David Foster Wallace, it’s fair to say that I’m a fan of reading commencement addresses. As I think about it, they cover some of the same ground, albeit from very different perspectives. The type of advice on how to live a meaningful life that we so often simply skip in our Western education’s rush to tell us how to get and perform jobs.

I won’t spoil the read, as I highly recommend the book whether you’re a vulnerable human or a professional optimizing for results, or some combination of the two. But I will say my favorite part was Pema’s intentional use of the word “forward,” rather than “positive,” in describing the power of being intentional about your attitude on life.

“Let’s use the word forward, instead of positive, because that includes whatever might happen. Instead of going backward into trying to find these little islands of security that keep giving out on you, you learn instead to fly or float and be okay in the formlessness or the groundlessness or the open-endedness of things, which is who you truly have been all along.”

Pema Chodron — Fail, Fail Again, Fail Better

Day 3 of COVID-19 quarantine

I walked out my front door on Sunday to the mailbox to get our first delivery of the New York Times newspaper (as opposed to digital). Laura had been excited that morning to work on the crossword, and I needed to fulfill the promise of that excitement. There hadn’t been much excitement since things started closing down on Thursday, but the little things still shined through if you blew on the embers.

I caught my neighbor’s eye from across the street as he returned, clad in spandex and a helmet, from a bike ride. We nodded to one another and he went into his house. Another neighbor drove past our house and up his driveway, waving at me as he passed.

As the street cleared I felt a sadness. It was a beautiful day, and it dawned on me that I was disappointed our interactions hadn’t been more meaningful. I realized that I yearned to talk to my neighbors, to connect, although we had never been more than neighbors. Amidst all the uncertainty and chaos, the sun was shining and I longed for contact with these people I knew only generally.

I went back inside.


I walked out my front door on Sunday to greet the middle aged couple approaching our house with their labradoodle. I didn’t make a habit of watching people out the window, much less meeting visitors before they made it to the door, but today was a special day. The third day since the world changed.

They stopped about 20 feet from me, and the woman brandishing a pink envelope said, “we won’t come any closer” either because of something in her or in response to something she saw in me. She explained that the letter had showed up in their mailbox as someone had miswritten a digit, and they were simply dropping it by and figured they’d introduce themselves. I was glad to talk to these people, but was relieved all the same when they said they would put the letter in our mailbox and walked away. I went back inside.

I didn’t retrieve the letter until much later, after they were long gone.


I walked out my front door dressed in workout gear over long underwear I’d last worn to go snowboarding a few weeks prior, and before that not since my crossfit days years ago. I put my Airpods in and selected a podcast about the mind’s powerful but mysterious ability to heal the body. I began jogging down the street, easing into a motion I had avoided for years. Basketball 3-5 times weekly had kept me in shape, but after the NBA shut down our local YMCA followed suit and so it appeared that sports-as-fitness wouldn’t happen for a while.

So I jogged. My side hurt almost immediately, but I pushed through and the pain soon subsided. The guy on the podcast explained that pain was simply a miscalibration of chemicals in our brain. The guest, a neuroscientist, said that the evidence showed that people lived with all the pain we’d ever experienced throughout our lives, but that the brain kept us from feeling much of it with a cocktail of chemicals purpose designed to neutralize old pains. To bring us back to normal, tare out the scale. An old ache in my hip and in my knee flared, and I wondered when my brain would neutralize it. I wondered if the world’s brain worked the same way for global pain.

I passed people walking, people in their front yards and in their cars as I ran. I made eye contact with many of them, and returned wistful smiles even as one or the other of us crossed to the other side of the street.

After about an hour run the podcast ended and I rounded the corner into our cul de sac. I saw another neighbor outside with his sons, tinkering with a car. I stopped about 10 feet away, took out my Airpods and said hi to him, as his son glided around on a hoverboard. He explained that they’d be heading to a cabin in North Carolina in the next few days, because he figured if everything was going to be locked down he’d prefer to be in a warm climate. “Trying to make memories out of all this, ya know?” he said. I said I thought we’d all remember this no matter what we did. He agreed, and clarified: “well, good memories. As much as I can, at least.” He went back into his house and his sons followed.

As they walked away I felt that yearning again, a sense that there was something more to say. But I didn’t know what.

I stood alone on a street normally filled with kids playing with rockets and bikes. Cars were in every driveway, lights flickered from every house, but even though we were all here, each of us was alone. Everyone hunkering down in their home with their families and their interpretations.

I thought of Laura and my boys. I thought of what might happen to them, what I needed to do to keep them healthy. I thought of trying to get a 3-year old to stop touching his face, never mind explaining “social distancing.” I thought of mortality statistics, of 14% for old people and 0.02% for young people, and how nobody seemed to really know. I thought about the world and about all the people who relied on gatherings over 50 people. I thought about my basketball team, many of whom thought the media was blowing things out of proportion and were simply angry they couldn’t play. I thought of the day I spent in bed the week before, which at the time seemed like only a “gastro thing.” I thought about my mom, over 60, but relatively healthy. No respiratory issues. I thought about how easy it was to get swallowed up by all the grey area in the world.

And then I saw Laura through the window, in the living room assembling a puzzle with my son. I saw a smile on his face. I smiled.

I went back inside.

Clothespin – or – When I took the red pill

“We’re going to prove to you that you don’t exist,” the teacher told us with a twinkle in his eye. “At least not in the way that you think you do.”

At a younger age I would have geared up to prove him wrong. But at 34, having just hired my replacement in my company and in so doing unknowingly abdicating the crux of my identity, sitting in lotus position in the main Gompa of the Vajrapani Monastery at the end of a dirt road two hours drive zigzag up a mountain from San Francisco, about 30 minutes beyond where Uber’s maps don’t go, I was open to listening.

“Think about this clothespin,” he said. “It’s a clothespin, plain as day. Nobody would say that it does not exist, right?” The Brit in our group, Amy, caveated to say it was actually a ‘clothespeg’, explaining that she and her brother used to launch them at one another as children. Regardless, everyone agreed the wooden clothes-hanging utensil did, in fact, exist.

“But I simply do this,” he took one of the wooden sticks from the clothespin, hiding the other stick and the still-attached metal spring behind the lectern, “and tell me, what is this now?”

It was a wooden stick, shaped with divots that would enable a clothespin to be formed if joined with an identical mate and fitted spring. But while it still had a hint of clothespin, kind of, I wasn’t sure it would have been any more than a stick from the distance I was sitting, had I not seen it in its previous condition a moment before.

“What about this?” He held up the other side of the clothespin. “Is this a clothespin? Would you be happy to purchase a bag of these?”

No. Just another stick. And a spring.

He prodded, “is the spring a clothespin?”

We shook our heads.

“So a moment ago we all agreed we were looking at a clothespin, and nobody would argue that it did not exist,” he said. “You didn’t have to think about it, or consider it at all. You simply knew innately what it was called, and what it was for. It had ‘CLOTHESPIN’ written all over it, as if its very essence was that of clothespin.

“But now, I only have to look at it a little closer–I have moved my hands and that is all–and now you say it’s no longer a clothespin. Well then, I ask you, what is it?” He held up the two sticks and spring.

Someone answered it was two sticks and a spring.

“Hmm… I think you are right,” he said. “No use to hang clothes.”

He put the sticks next to one another, and wrapped the spring around them to once more create a single object. “And again, what is this?”

A clothespin. Its essence returned as if by magic.

“So this clothespin now exists once more, but a moment ago it did not,” he said. “So now we have agreed that a thing can both exist, and not exist, at the same time. In other words, a thing can be what it is, and also be only its parts, its causes and conditions as one might say, at the same time.

“So what makes this, then, a clothespin?”

Someone said that we labeled it so. Someone else said that it could hang clothes.

“I see,” the teacher said. “So we are saying that there is nothing about this object that makes it internally ‘clothespin’, apart from our giving it a name and a purpose. Is that right?”

We nodded.

He bowed his head. “I would like to suggest to you, humbly, that you exist in the same way, and in only the same way.”

I felt numb.

“I would further suggest,” he continued, gesturing toward Amy. “That it could as easily be called ‘Clothespeg,’ and be used as a projectile, if you so chose.”

How leaning in to my greatest fear enabled me to make better decisions

Fear drives much of our lives. Neutralize your fear by leaning into it, and free yourself to make better decisions.

I’m convinced that everything I do is either to A) steer myself toward feelings that I interpret as positive or good, or B) avoid feelings I interpret as negative or bad. There really isn’t more too it than that.

I will go to incredible lengths to curate the feelings I’m exposed to. I have ended relationships rather than face my own failings within them. I have blamed others or the world rather than confront something I’ve done wrong. Most often, I will imprison myself and everyone around me in my own personal tunnel-vision, diminishing everything that is not the Goal with a wave of dismissal in an effort to avoid my deepest fear: shame, stemming from my deep recognition that I’m Not Good Enough.

Usually this means making knee-jerk, fear based decisions in reaction to feeling Not Good Enough, that seem right in the moment but that I often regret later on. I’ve sent so many emails that enabled me to check a box, get that dopamine hit of productivity in the moment, but that actually did more harm than good in the long run (sometimes I see this as quickly as 5 seconds after hitting send–#grateful for the ability to un-send these days).

It took me forever to realize what was going on, and develop an alternative.


I learned that I wasn’t good enough early in life, sometime before I can remember, and when I learned that I made the decision that I would do anything, literally anything, to prove otherwise. My whole life from that point forward has been one long series of achievements without end, each one seeming like the most important thing in the world until I attained it, at which point it was and had always been irrelevant. I was still not enough, and only the next achievement would prove otherwise. Etcetera, ad infinitum.

It wasn’t until I stopped achieving, forced through failure (providence?) to slow down, that I had the amazing opportunity to really take stock of the operating system through which I was living. I wouldn’t have chosen to stop achieving, because frankly it pays well, offers tons of positive feedback (the US consumer culture reinforces your worth as a function of your possessions / achievements), and it was painful as all hell to confront the feeling of my own inadequacy head on, rather than continuing to run away from them with the next gold star. But I’m so glad I gutted through it because through that process I was able to see the pattern of my mind’s machinations in a way that demystified it, and offerred me a choice I never knew I had:

Rather than achieving to run faster away from my own inadequacy, I could simply stop. I could stop putting myself through such ambitious hell, and simply deal with what was there.

Moreover, by dealing with what was there rather than running, I could avoid making the kinds of fear-based decisions that I usually regretted. By simply looking at reality without trying to fix it, I could see more clearly what there was to do, and make better decisions.


The thought of confronting my fear and my shame was terrifying, but so was the prospect of jumping back on the treadmill of achievement and simply pretending that I still thought hitting that next milestone would make me happy. So I did it. I simply stopped, taking two months off of work (not all of us are so fortunate, I recognize), and confronted it.

And crazy enough, I didn’t die.

Oh it hurt, for sure. There’s a reason I was subconsciously pushing so hard to avoid these feelings. Swimming in inadequacy was a kind of exquisite torture that I could never have prepared for, but thanks to many psychological and spiritual tools and mentors I was able to stay with the emotions, negative as I perceived them to be, and simply be. And in that, there was a freedom.

I didn’t have to reflexively jump into action and check an item off my to-do list. I didn’t have to mentally diminish myself or someone else in an effort to right-set some mental social hierarchy to make myself feel better. I didn’t have to do anything, in fact. I could just do nothing, and as Trungpa Rinpoche says, “Lean into the sharp points.” Feel what there was to feel, what I had been running from for so long, and let it pass.

By sticking with the feeling without succumbing to the intense urge to do something productive in response, I was able to develop a familiarity with it.

For me, fear of not doing enough feels like:

  • Tight chest, like when I smoked too much. I can’t get a full breath
  • Eyes feel wired, like I haven’t slept
  • My heart beat is audible, particularly when I see success in others
  • My mind spins, playing a loop of how my achievements compare to those who are more accomplished than me
  • Intense feeling that there is something wrong

I have no way of knowing if that’s the feeling for others, but now that I’ve stuck with it a number of times, really made it a point to taste the flavor of the feeling rather than running from it, I know the characteristics of that particular fear for me. I can recognize it when it comes, enabling me to actively avoid jumping into action as would be my reflex. And I know from experience that it always goes away, even if it feels like this time it’s going to last forever (it always does).


I’ve become familiar with my primal fear, that I’m existentially Not Good Enough, and will never be Good Enough. Certainly I’m not friendly with it, but I’m acquainted enough to recognize it for what it is. The fear that I’d jumped through hoops of fire to avoid, when you really boil it down, is simply a series of bodily sensations combined with a reflexive urge to achieve.

For a long time I’d unknowingly let that feeling drive so many of my actions, forcing me into suboptimal, fear-based decisions, and unproductive, repetitive patterns (and also, to be fair, into some success, albeit at the cost of relationships and consciousness).

The feeling still comes up regularly, but now when it does I’ve learned that there’s a choice. Most of the time, when I’m at my best, I simply sit with the feeling and appreciate how its intensity reminds me that I’m alive.

Then look at the situation with a clarity of mind that used to be inaccessible, and do the next right thing (HT my 3 year old).

Sit with the question

My mind is an answering machine. It comes up with answers, meanings, conclusions, theories all day, every day. It’s automatic.

It likes the solidity. To feel like, in the immortal words of the narrator of Fight Club, that whatever else happens, I’ve got that sofa problem handled.

Humans like solidity in general, I think. We build things constantly, taking ephemeral things like trees and people and making them into solid things like houses and businesses, each time answering an unspoken question. Each time we do this, we take something alive and full of potential–a question–and stamp an answer on it.

My brain tries to stamp my life solid as well. What am I? Well, I’m an entrepreneur. There, answered. Don’t like that? Well, I’m a basketball player. A leader. A good looking guy (with a growing bald spot). My brain can do this forever.

It stamps other people with labels, too. This woman is good, this one is mean. This guy is more successful than me. This one is not interesting. Over and over, all the time.

But none of that is real. All the answers are made up, and only exist to limit my experience. Humans (and all of reality) are really one big question, and we’re just trying to make ourselves less anxious with all our stamping answers on everything. Stamping someone with a label doesn’t change the person, only limits our relationship to them to a relationship with their label.

I find the alternative, when I remember to do it, much more rewarding (not to mention fundamentally, unavoidably, more accurate). I find I pay much closer attention to the amazing, detailed, massive, changing aliveness of my life, and all the people in it, when I simply sit with the question.

How to build a sandcastle (or anything)

1990

I woke up slowly to the sun shining through the sheets, and pulled my blanket up over my face to bring back the darkness. I was settling back into my dream when I remembered. I jolted awake.

The sandcastle.

My dad and I spent all day building it, while my mom sat on the beach reading her book. My dad said the trick was to start by making the sand wet so it was strong. We filled my blue bucket with water and sloshed it over the sand, making a wet spot partway up the beach. Then we went back to the water and filled the bucket with wet sand. We packed it down tight and brought it back up to the wet spot, and when we flipped the bucket over on its head the sand that came out was shaped like a castle. But you had to lift it up so quietly. Otherwise the sand falls apart and you have to do it again.

We made four castles like this, and then my dad showed me how to make the walls connecting the castles. We smooshed sand into tall walls, and then we carved windows in them so the sand soldiers could shoot arrows at the bad guys. We had to make sure that the walls were flat on the top, too, so the people could walk across them without falling down. I did a wall all by myself, but it wasn’t as flat as the other ones.

Then we did a trick. We took wet sand in our hands from the water and ran so fast back to the castle and dribbled the sand in our fists and made spikes on the top of the castle. Every spike we did special like this. These were for protection. We made little windows in the spikes too with a stick, just like the castle in the beginning of movies. This way the townspeople could see out.

My dad never made a sandcastle with me before. It was perfect.

I threw on my clothes from the floor, dirty from last night but that’s ok, and ran downstairs. My dad was eating breakfast. He was usually gone when I woke up, but at our vacation house he didn’t have to go to work so he was there and he smiled when I came down. I told him I wanted to see the sandcastle we made, and he said he’d come with me down to the beach. We ran down the stairs and took off our shoes and ran onto the sand. My dad couldn’t keep up with me because I’m so fast.

But it was gone. Our sandcastle was gone, and the sand was wet everywhere around where it was, not just in the one spot. I cried and cried, and my dad hugged me. I hated the sandcastle. It was perfect, but it was gone.


2020

I thought of that day so long ago with my dad, when I built a sandcastle with my son at the beach in Northport last summer. We wetted the sand and used a bucket that looked almost like the one I remember to create the turrets. We crafted the walls just so, and added the spikes that were my favorite part when I was young. My son lit up when he saw how the dripping sand stalagmited into spikes on the corners of the castle. That was the best part. Well, that and when I showed him how to draw the windows. I told him we had to make it just perfect, so the townspeople could live there. He found two pinecones and put them inside the castle, and said they were the mayors. He was so proud. It was perfect.

I told him it wouldn’t last, that it would be gone by tomorrow, but even though he acted like he understood then, it still hit him hard when the tide came in and washed everything away. He said he hated it, and he wished we had never made it. He cried so hard, I almost wished we didn’t make the sandcastle. Well, maybe not, but at least I understood.

I’m so glad we made the sandcastle, but I’ve stopped caring about sandcastles long ago. I’m so glad because I got to spend time with my son, and see the gleam in his eye when we dribbled those spikes for the first time. I can still see it now.

It’s gone, but it was perfect.

Every rose has its thorns

The deeper I go into the nature of things, the more I see paradox.

Where there is light, there is darkness. Where there is good, there is bad. There’s a reason that the Yin/Yang symbol has withstood the test of time. It’s a map of reality. I’m learning there is no such thing as Good or Bad, really. It’s perspectival, in that one man’s food is another man’s poison (I think that’s how the Bible puts it), or one being’s poop is another being’s fertilizer, if you like. It’s also a blend, in that everything good has within it something bad, and everything bad has a redeeming aspect within.

As deep as I can dig, this seems to be always true. There is nothing purely good, or purely evil. Purely light, or dark.

I have done things that, depending on who you are, may make you think I’m a downright bad person. Probably many people I happened upon in college, during the throes of my drinking days. We won’t go into specifics on this post, but suffice it to say I didn’t much care about other people, except in as much as they could help me get what I wanted. I sometimes do that even now, but people who know me now can (I hope) attest that at least I’m not PURELY an asshole. Most people who know me now, I think, think I’m quite a good person. This would no doubt shock some people in my earlier lives.

Depending on which part of me you are familiar with, you think I’m mostly good or mostly bad, but either way it’s nuanced. Which brings me to today.

Today I was confronted with how one of the things I like most about myself, the aspect of my personality which has gotten me so much, which I’ve always found so positive, also has a dark side.

And it’s because of that dark side that, after publishing a post every weekday for some time now, I’ve decided to ratchet down the pace of this blog to 2x/week.


One of the things I know about myself is that I keep my word. When I say I’m going to do something, I do it. End of story. It took a lot of work to develop that relationship, a lot of trying to keep my word, failing, confronting that failure, trying again, pushing past whatever is in the way, succeeding, trying again, etc., but for the last 10 years or so I’ve been enjoying a relationship with my word which is essentially iron clad. When I tell myself that I’m going to do something, then I will move heaven and earth to do it. It’s even more effective when I tell someone else, because then there’s the social pressure of letting them down as well. Can’t chance looking bad in someone’s eyes, so better hustle and get it done.

This is probably the single biggest character trait responsible for whatever success I’ve had in business. Once I say I’m going to do something, it doesn’t matter what life looks like, that thing gets done. I’ve tried to pass that trait down to our employees because it’s been so valuable to me, and for the most part I think we do a great job, and our business has flourished on our collective commitment to DWYSYWD (do what you said you would do). From my experience, developing a habit of giving and keeping your word is among the most powerful things you can do for your career and life, hands down.

It’s from this framework of unquestioning DWYSYWD that I started writing a month ago. I didn’t really know if there was a point to the writing, as I had nothing to accomplish by being open online. I didn’t have a goal, and in fact resisted the idea of a goal out of principle. I just liked to write, and something deep inside me made me feel like now was the time, after 10+ years, to finally get back on the horse. So there was really no outside reason for me to write so much, but it didn’t matter. I had told myself I was going to write every day, so everything else beyond that was immaterial. I would simply write every day, and life could work its way around that fact.

And, as per usual, I did. Every damn day, including many inconvenient days waking up earlier than 4 in the morning. And now I have a bunch of writing, some of which might be ok, and more importantly than that I have gotten back into the swing of the writing, which in retrospect was probably the point.

But like everything, there’s a Yang to this Yin. There’s a downside. And for me, I have recently learned that one of the reasons I’m so black-and-white about my relationship with my word is tied up very deeply in my habit of measuring my self-worth based on my accomplishments (which I’ve written about here and here). As I’ve peeled back the layers of my thinking, I’ve seen that in the same way I valued myself by the success of my business, I also valued myself based on my ability to stick to my word. In the case of this blog that manifested in the belief that I was somehow unworthy if I missed a day.

Ah crap, I thought when I recognized it. That’s that same pattern again.

As effective as I know that framework to be as a means of getting shit done, I have over time become unwilling to consciously anchor my mental, emotional and spiritual well-being to my accomplishments. It’s not worth it, because I know the end of that story. You do and get a lot, but there is never, and can never be, enough accomplishment to satisfy that craving. So you chase gold stars your whole life and die feeling unworthy. No thanks. Self worth can only come from inside, not from any amount of gold stars (even though America would have you believe otherwise).

So, as I’ve started doing when I notice my mental machinery in action, I am letting go. I still very much like writing, and imagine I’ll continue to do it a lot. I still very much like that it’s normal for me to keep my commitments to others and myself, and I imagine I’ll continue to do that as well. But it’s become unavoidable to me that the framework of “I will write every day,” while effective, has become toxic for me at this point in my journey.

So I’m letting go.


What does this mean? Well, due to my nature to overachieve I’m already writing weeks ahead of the present date, so I’ll let those run their course coming out every Tuesday and Thursday, instead of every day. Or maybe Monday and Wednesday. Who knows. And we’ll try the 2x/week pacing and see if it works. Or maybe three times per week, or one. We’ll see. I can feel a weight being lifted in writing that.

I’ll continue writing, and my hope is I find myself in a spot where I do so not because I’m committed through a structure that has become a proxy for my sense of self, but because writing is simply an expressive action that I am called to do.

That’s why I started writing a month ago, after 10 years letting the habit languish. To express things, not to get somewhere. And I think that’s where the work I’m meant to do–maybe even the words I’m meant to write–will come from as well. There’s no end to a life built on achieving, despite what media tells us. There is always someone with more.

As Thomas Merton put it, “the life of riches, ambition, pleasure, is in reality an intolerable servitude in which one lives for what is always out of reach.” I want off that treadmill, and that means giving my writing space to become something organic (again), even at the risk of “success.”

My word is my bond, I’ve always thought. And I’ve always been proud of that. But I’ve seen that my word can become my prison as well, every bit as much as the mental patterns through which I interpret the world.

More than any amount of success, I want to be free.


So henceforth, look for a post around twice a week from me. I’m guessing subscribers’ inboxes will be better for it anyway.