about me

Life and leadership lessons from Dungeons & Dragons

Last year I started playing Dungeons & Dragons for the first time. As a D&D newbie I was nervous. Would I have to wear a costume? I didn’t even how the game was played.

For those new to Dungeons & Dragons, here’s how it works: a narrator (the dungeon master) reads out to a group of people descriptions of a place or scenario. The group decides what to do, and the narrator unfolds the story based on their decisions. At certain moments players roll dice to determine the outcome of a decision. It’s basically a free-form, collaborative Choose Your Own Adventure story.

At the same time I started playing D&D, I was transitioning into a new job as CEO of Kickstarter. I initially started playing to hang out with the Kickstarter team. Over time the game has become much more. Here are three things I’ve learned playing D&D.

1. Know who you are

Knowing and accepting who you are is the most important thing to do in D&D and life in general.

In D&D this is quite deliberate. When building a character you’re first asked to declare whether you are Lawful, Neutral, or Chaos. My group began by declaring ourselves Neutral, but events soon revealed a darker edge. After a particularly gruesome encounter, it was obvious: we were Chaos.

Accepting our Chaotic nature was a literal game-changer. Rather than debate how to respond to each situation, it was clear how to act. Once we knew who we were, there was often only one real course of action.

2. Know what you want

In our adventure we began hearing rumors of the Master, the root of evil in our world.

One day I made a proposal to the group. We would find the Master. We would pay tribute to him as his subjects. And then we would slay him and become the new Masters ourselves. We all agreed to this audacious plan, and everything about our game immediately changed.

D&D is typically about exploration. You search rooms, open doors, and explore terrain. Once we declared our mission, things took a different shape. We explored, but with a purpose.

We began to see anything that wouldn’t ultimately lead us to the Master as a distraction. We encountered countless corridors and mountains of treasure. We ignored all but those that seemed likely to lead us to the Master.

The impact of our focus was startling. Questions of tactics and strategy continued to arise, but we approached them with an obvious purpose. Once we decided who we were and what we wanted, it was clear what to do.

After much searching, we finally found the Master. We declared allegiance as planned, and soon found ourselves in battle. After a long and difficult fight, we were victorious. We took the Master’s seat.

3. Parlay first, fight second

When we started our quest, we would engage in battle as soon as we encountered an enemy. We won these battles but they were painstaking. We had to fight enemies one at a time. Our characters were weak and inexperienced. The risk of death was real.

Over time we began to take a different approach. We would first try to parlay with the enemies and convince them to help us or surrender. We used appeals, threats, and tricks to get them to lead us to the Master.

Parlaying had much bigger rewards than fighting. By parlaying we could impact an entire group of enemies, not just ones we physically fought. Soon we began every encounter with an attempted parlay. We would fight only if that failed.

Thankfully I don’t have any literal application of this lesson to my life, but it reminds me of how important it is to scale your actions. It’s satisfying to roll up your sleeves and try to fix every problem yourself, but big picture it isn’t sustainable. There’s just too much to do.

Instead, parlay by sharing the challenge with your team. Even if the efforts come up short, the team has gotten more experience, and your performance in the next challenge will be much improved.

I’ve come to see our Dungeons & Dragons quest as more than a battle with monsters and mazes. It’s been a test of character. The obstacles we faced gave our group purpose and helped define who we are.

Who are you? What do you want? These are the questions to answer. We can’t control events, but we control how we respond to them. Who knows? With a little bit of luck, you just might find yourself the new Master.

My D&D game. From left to right: John, Taylor, Luke, Liz & George

I wouldn’t have survived to learn these lessons without my brave compatriots. Thanks to Liz Cook, George Schmalz, Taylor Moore, and John Dimatos for their wits and wit. And thanks to our incredible dungeon master Luke Crane for guiding us on our quest.

I shared a draft of this essay with the group before posting. Liz responded with her perspective. Here’s her take:

Thinking about taking down the master/becoming the new master was both hilarious and undeniably the right move. It was also very risky — and I think that risk played an important role. It made staying on task feel even more crucial. We were aware of our scrappy first or maaaybe second level brigade and that feeling of being ill-prepared propelled us to stay on target…cause we had to. Don’t you think it could’ve felt different in circumstances where we came with higher levels or more powerful spells or just knowing what to expect? I also wonder if we felt brave because we didn’t feel like we had so much to lose yet. We hadn’t leveled up a number of times. Maybe our lack of experience made us less likely to fear what we had to lose. Maybe it was the fact that we weren’t safe peddling around the caves and could die at any time regardless? I don’t think any of this takes away from our glory or bravery and certainly not our determination to reach our goal however.
Some of my all time favorite moments in the game have been the parlay encounters. A big part of why I enjoy them is the human-ness that it brings to our D&D world. Fighting is definitely fun but even when Luke does such an amazing job painting the battle scene, it can still feel very anonymous to me. A parlay invites emotion, spontaneity, and an unpredictability in outcome that just delights me to no end. This holds true in real life as well.

I couldn’t agree more.

Thanks for reading.

What was the first year at Kickstarter like?

The first first-year: 2001 — 2002

This is when Perry had the idea for Kickstarter. He was living in New Orleans, wanted to throw a Kruder & Dorfmeister concert during JazzFest, but didn’t have the means to pull it together. This led him to imagine a system where he could propose something like a concert to the public, people could use their credit cards to pledge to it if they liked the idea, and if enough people did the thing would happen.

You can read about this period in Perry’s own words here and here.

My first first-year: 2005 — 2006

Perry and I met in the fall of 2005. I was a regular at a restaurant in Brooklyn where he waited tables. Perry had continued to work on the idea for Kickstarter, and eventually he told me about it. We started discussing it over beers and ping-pong.

The idea got steadily more real for me as we shared it with our friends — many of whom were artists we hoped would one day use Kickstarter, and whose feedback we incessantly solicited.

One day we walked to Staples in Soho and bought a whiteboard. That was a moment. Perry used that whiteboard to sketch this early design.

What sticks out from my first year is the discrepancy between our enthusiasm for the idea and everyone else’s. We were constantly talking to people about Kickstarter and getting blank faces in return.

In retrospect this was valuable. Trying to explain something that doesn’t exist yet is a good way to learn what’s interesting about it. It made us understand the “why” of what we were trying to do. The fact that our creative friends got it but the business people we spoke with were baffled by it was a strong sign to us that this was something worth doing.

Charles’ first first-year: 2007 — 2008

Before Kickstarter, Perry had been an artist, day trader, recording engineer, gallerist, and pre-school teacher. I was a rock critic and writer. Ends up these are not the best qualifications to start a website.

In 2007 Perry was introduced to Charles, and things began to take better shape. Charles was a designer. He and Perry worked closely to interpret the ideas into wireframes and sketches. We actually detailed the entire design history of Kickstarter (with lots of early screenshots!) in this post. An example of a design circa 2007:

From 2007 to 2009 momentum was building. Full credit goes to Perry and Charles, who sat in Perry’s apartment in BedStuy everyday talking, sketching, and debating without pay (I still had a day job as a writer). There were many very challenging times. Perry bore the brunt of them but he refused to give up.

Kickstarter’s first public year: 2009 — 2010

On April 28, 2009 at 4:30pm Kickstarter went live. The first project was by Perry. The second was by me, Perry, and our friend Claudia. Our Moms were very excited.

Before launching, we gave about 50 of our friends invites to start projects, and five invites to give to their friends, and so on. To date this is still the most marketing we’ve ever done. By our second day people we had never met were launching projects. On our third day Drawing for dollars became the first successfully funded project, at $35.

The team was very small. Perry, me, Charles, Lance Ivy, Andy Baio, and a part-time developer in Texas. Charles was in Chicago, Lance in Walla Walla, and Andy in Portland. Only Perry and I were in NYC. In June everyone came to New York for a visit. There’s an awkward photo somewhere of us standing in front of the New York Public Library by Bryant Park.

In October 2009 we made our first full-time NYC hires: Cassie Marketos to join me on CS, and Fred Benenson to join us for data and engineering. In December 2009 we got our first office, a floor of an old tenement building on the Lower East Side. Perry found it on Craigslist. I remember spending New Year’s Day putting together office chairs. This was our home until just a few weeks ago.

All of us were completely new at this. For Perry this was the culmination of nine years of dogged persistence and thinking. For me it was the culmination of a life spent celebrating art and culture. For Charles it was the culmination of years of working on a variety of creative projects. It was — and still is! — very exciting.

Kickstarter is the kind of thing that seems as natural as air — the structure of the system, how it works and feels, the fact that it exists at all. But it isn’t. It is the product of years of thinking, collaborating, building, and ultimately guessing by a handful of people. It’s been copied so many times now that the original thought doesn’t seem very original. It very much was.

The fact that Kickstarter has become what it is is remarkable. I see all of the site’s success through the lens of these years. It’s been a privilege to be a part of it.

Sunday in London

It’s an autumn Sunday in London. Walking from the V&A Museum through the white Rolls Royces’ of Westminster through Hyde Park along the lake. Families pose for pictures while five brown ducks with red raccoon eyes look both ways before crossing the path.

The sky is gray and getting grayer. It begins to rain. A drizzle at first, and then a slanted downpour. I dash underneath a tree and stand next to a cyclist and a man on a Vespa and watch the rain come down. Across the lake we hear the screams and music of a distant party. Above us the drops smack the leaves in a muted *thwack*. We sit in silence. I’m the last to leave.

An hour-long interview between me and Glenn Fleishman covering the history of Kickstarter, the relationship between artists and money, and I walkthrough our approval process for new projects in depth.

Cannon Beach

Several coworkers and I were in Portland for an event this weekend, and late on Saturday night the day was winding down. I had rented a car, and I offered to drive people home. Hayley, Liz, and Luke raised their hands, and off we went.

As we got into the car I warned everyone that I was going to make them ride around and listen to Kanye with me (more accurately, they would listen to me enthusiastically rap along to Kanye) before taking them home. “We’re going to drive across every bridge in Portland,” I said. There are a lot of bridges in Portland. Everyone liked this idea.

Liz piped up from the backseat: “You know, the ocean is about two hours away…”

I slowed the car. It was 2am. It was rainy. It was cold. It had been a very long day. I was wearing a suit.

"Let’s do it," I said.

"I’m in," Liz said.

"I’m in," Luke said.

"I’m in," Hayley said.

"So how do we get there?"

We turned left and headed West — music blasting and windows down, rain be damned. I drove, Hayley navigated, and Liz and Luke invented dance moves in the backseat. We marveled at the austerity of Oregon’s road signs: “Trucks,” “Rocks,” “Fresh water,” “Speed 50.” Cannon Beach was 80 miles away.

We climbed mountains in the darkness. We could just make out the silhouettes of the giant pines surrounding us. As we climbed higher we were doused in fog, and it became almost impossible to see. Very few cars were on the road.

Finally we arrived at Cannon Beach. It was very late — 3:30am — and the town was silent. We took a left, drove two blocks to the road’s end, and bounded out of the car. There it was: the Pacific.

The beach was long and wide. It was low tide, and the waves were breaking 100 yards from the water’s edge. From the waves to us was a shallow skim of water many yards long and many miles wide. We danced along it. Hayley shot a video of her hand touching the Pacific Ocean for the first time.

The moon was full and the sky was overcast. The world was a muffled shade of grey. To our left in the distance we could make out the beach’s giant iconic rocks jutting from the ocean. They looked like sleeping monsters. We laughed and shivered and walked in their direction.

We passed two small bonfires with a few people huddled around. We kept moving and eventually came across an unattended fire. We stopped. The fire was bright with blue and green flames. We warmed our hands and I warmed my bare feet.

Giant black birds stood in the waves nearby, and Liz and I walked into the water towards them. The shallow surf stretched from our feet to the big rocks hunched in the haze ahead. Moonlight glimmered on the wet sand. Everything was moving and perfectly still. It was a desert of grey. The world was infinite.

"This feels like death," I said. I meant it in the best possible way.

My eyes were locked on the big rocks, and they drew me ahead of the group. Even though I was freezing I walked with my feet in the water. I had to be immersed. Even the suit I was wearing was grey.

I reached the rocks and stood before them. Minutes later the others joined me, and the four of us stood and stared. They were beautiful, staccato silhouettes. Luke offered words of thanks to Poseidon. Immediately a wave burst from the ocean and rushed at our feet. We backpedaled with gratitude and laughter.

It was time to head back. The night hadn’t gotten any warmer, and we stopped again at our fire. We warmed ourselves before starting the walk back. I walked most of it with my eyes shut. The drive home would be a long one.

We piled back into the car and I took the wheel. It was almost 5am. Hayley and Liz dropped off into sleep, and soon it was just Luke and I talking. After a half-hour I pulled over and asked Luke to drive. The others woke to keep Luke company, and I dozed off in the backseat.

An hour later I opened my eyes to see the outskirts of Portland. It was after 6am and the Eastern sky ahead was beginning to fill with light. It was morning, and we were home.

The Trip — Day 8

We woke up in San Francisco on our last full day. The plan was to explore the city and then drive to LA that afternoon. Our flights were out of LAX the next day.

The morning got off to a rocky start. We had a heavy day of walking in front of us but Dylan had worn flip-flops. A half-hour into our day he was struggling. So I did the only sensible thing a New York big brother could do: take him to the nearest store and buy a pair of shoes.

Minutes later Dylan was sporting a sweet pair of Campers, but with one small problem: we didn’t get socks. Three blocks later Dylan was in searing pain that was getting worse by the second. We tended to his heels — they were bloody and blistered after just ten minutes — and bought socks. Poor Dylan.


Our comrade had fallen, and yet we marched on (in a taxi). Dylan had one request for the day: that we go to a record store. We went to Amoeba Records on Haight Street, one of the biggest and best record stores in the world. Stephen and Dylan (even with his injury) sprinted to the vinyl racks the moment we walked in.

We spent more than an hour thumbing through albums. I told Stephen and Dylan to each pick out three records to buy. I decided that I would do the same for each of them. And they on their own decided that they would each recommend an album that the other buy for themselves. It was a system of reciprocity where everyone would benefit, Amoeba especially.

Stephen got Neutral Milk Hotel, the new Boards of Canada, and Bonobo (Dylan’s recommendation). Dylan got Toro y Moi, Bonobo, and the Eraser (Stephen’s recommendation).

I had a lot of fun deciding what to get. I picked out a similar record musically for each of them, but specifically tailored to their personalities. For Stephen, I got Isaac Hayes’ “Hot Buttered Soul.” For Dylan, James Brown’s “Live at the Apollo 1962.” For Stephen, Terry Riley’s “A Rainbow in Curved Air.” For Dylan, Terry Riley’s “In C.” For Stephen, the reggae compilation “Studio One Roots.” For Dylan, the reggae compilation “Studio One Funk 45s.” In the end they were pretty pleased with their haul.


I walked us up Haight to the corner of Ashbury, and asked them to pose for a picture at the intersection. Its significance was lost on them, but I assured them that their parents would appreciate it.


It was time to leave San Francisco. We piled into the car and headed south towards LA. We were going to go through Big Sur, one of my favorite places on earth. But first we had to stop at In-N-Out, this being California after all.


A week earlier we began our trip by taking the Pacific Coast Highway north along the ocean to Malibu. We were going to finish our trip by taking it south through Big Sur. There aren’t good enough adjectives to do Big Sur justice. Huge, lush mountains dropping straight into a rocky Pacific Ocean. A two-lane road winding right along the cliffs. It’s unfathomably gorgeous.

The drive was incredible. This time I was behind the wheel and Stephen and Dylan hung their heads out of the windows.

"My jaw keeps finding new places to drop," Dylan said.

"We’re so spoiled," Stephen said.

I timed our San Francisco departure so that we would drive through Big Sur at sunset. I wanted to watch the sun sink behind the Pacific while we watched from the cliffs. The sun cast its magic-hour light across us as we drove.

Ten minutes before sunset we pulled over. It was just like I imagined. We stood on a cliff and watched the sun go down. It’s something the three of us will always remember.

A mile ahead was a stretch of coast where you could get down to the beach. We stopped. A huge, undisturbed field separated the road and ocean, and Stephen sprinted across it to the water. Dylan, mangled feet and all, and I followed, running as fast as we could towards the last strips of sunset.

We scampered down the rocks, took off our shoes, and ran into the freezing Pacific. Darkness was falling but the white caps of the waves and the orange streak of the horizon lit our faces. We laughed and played in the surf. Our feet shivered but we didn’t care. It was us, the ocean, and the huge sky above.


The movie version of this trip would roll credits at this point, but there was still a little ways to go. We were four hours from LA and 12 hours from our flights home. On the drive’s final leg I shared some Big Brother advice. I asked them to look out for each another in a way that I’m not able to in New York. Be positive influences on each other. Help each other be your best selves. Do this for me and for each other. They agreed.

We got into LA late, and woke up early the next morning. We gathered our things, dropped off the rental car (that Jetta is the trip’s unsung hero), and went to the airport. Stephen and Dylan were flying to Virginia, and I was flying to New York. It was actually over.

While Stephen checked his luggage, Dylan and I reflected on the trip. “I’m coming home with a new brother,” Dylan said. I managed not to cry.

Stephen rejoined us and we stood together quietly. They hadn’t left yet and I was already missing them. How could it already be time to say goodbye? We hugged tightly, and then tighter still. I told them I loved them. And with a wave they were gone.


The Trip — Day 7

Today we woke up on the Utah-Nevada border. Yesterday we (Stephen) drove 12 hours nonstop to get here. Today’s goal was for us (Stephen) to drive another ten hours to San Francisco.

We woke up looking for breakfast, and found it in a diner that doubled as a casino. This, we soon learned, was true of everything in Nevada. Anything — absolutely anything — could be a casino if you tried hard enough. Eight new casino-somethings have opened in the time it took you to read this sentence.

Breakfast was tired and grumpy. Dylan was particularly quiet.

"What’s wrong?" I asked.

"A girl is giving me grief on Facebook," Dylan said.

"Grief over what?" I asked.


The drive across Nevada was, in a word, boring. It was a lot of nothing. Interstate 80 stretched infinitely. We’d round a smallish mountain only to see an identical valley in front of us with another smallish mountain ahead. The only entertaining sights were the signs telling us not to pick up hitchhikers near prisons.

Four hours into Nevada we stopped at a rest area. A few women were selling Native American jewelry. Stephen bought a necklace and bracelet, and Dylan bought a necklace.

"I was going to get the necklace with a bear on it, which means courage," Dylan said. "Instead I got one with a turtle." It might be the most Michael Cera-ish thing anyone has ever said.

We kept driving. Dylan slept in the back seat and Stephen and I talked up front. The world around us was covered in a deep haze, and we couldn’t figure out what it was. Eventually we realized that it was smoke from forest fires in Yosemite ahead.

Finally we crossed the California border, and the change was immediate. Tall mountains, regal pine trees, a beautiful river hugging the road. It was awe-inspiring. We agreed that whoever negotiated the Nevada-California border for Nevada had no idea what they were doing. 

As we crossed the border, Stephen made a very smart California joke: “Did Interstate 80 just become ‘The 80’?” I was proud.

Hours later we came upon San Francisco. Stephen navigated traffic, and suddenly there we were crossing the Golden Gate Bridge. It towered above us.

I booked us a room on the water between the Golden Gate and Bay Bridges, and we headed there. The room was very swank, with a separate living room and a big patio underneath the skyscrapers and stars. Even if we hadn’t just spent seven days wandering public parks, this was some cosmopolitan living.

For dinner we went to a tony San Francisco restaurant called AQ, which got its start via a Kickstarter project a few years ago. It was the fanciest place Stephen or Dylan had ever been, and they took full advantage of it.

Our meal started with two appetizers: peaches and ham (delicious) and swordfish and cactus (after being around cactus so much the past week I felt it was important that we eat some). For our entrees Dylan had sirloin and bone marrow, I had black cod, and Stephen had squab that the waitress warned him four times about before allowing him to order.

"It’s very medium-rare,” she cautioned repeatedly.

What she didn’t realize was that these warnings only made us more excited to see what would come. Apparently “very medium-rare” meant that it was essentially raw. Stephen — who lives on a dare-based diet — happily ate it all.

During dinner we talked about our trip and the three of us being together for the first time. Several times I had joked about something “bringing shame upon our family,” but it wasn’t clear what family I meant. They were both family to me, but what were they to each other?

This was apparent even with the simple use of nouns. Stephen and I share a mother, and Dylan and I share a father. Both parents remarried years ago, and I grew up with two step-parents who I remain close with. Stephen’s father is Tommy, and Dylan’s mother is Karen. Growing up I called them by their first names.

Whenever I’ve spoken to Stephen or Dylan about Tommy or Karen, though, I’ve always called them Dad and Mom. I’d ask Stephen how Dad is doing, meaning Tommy. I’d ask Dylan about Mom, meaning Karen. But with all of us together, this was confusing. Mom who? Families were colliding. I had to either make very direct eye-contact with the person whose Mom I was talking about, or I had to use first names. It was strange.

We walked home from dinner. I felt a palpable excitement at being in a city again — even San Francisco, a city I’ve been to many times and have never liked. We got home and sat together on our patio, laughing late into the night. The end of the trip was coming, and we were savoring every last second.

The Trip — Day 6

Shortly before we started I asked Twitter and Facebook where we should stop on our trip. The overwhelming choice was Arches National Park in Utah. Today we got to see whether you guys know what you’re talking about.

The answer of course is yes. Arches was wonderful, and reminiscent of many of our stops with its alien landscape. The huge outcroppings felt like the walls to some ancient civilization.

The park’s main attractions are — surprise, surprise — arches of rock. We pulled over and hiked to the first of these that we saw.

And as has been the theme this week, Stephen and Dylan immediately set to work climbing as high as they could on them.

They actually climbed even higher than this, but they were so high up that they don’t show up in my photos. That’s where this happened:

Maybe somethings are best left unseen… Meanwhile I chilled down below.

It was an incredibly hot day, and our next hike to Landscape Arch was a lot farther. Stephen was prepared.

Landscape Arch was worth every bit of the walk.

Nearby was another trail with signings warning of a very difficult hike. Of course we had to try. There was little in the way of a trail — more a series of boulders that led in a general direction. 

Let the record show that both Stephen and Dylan were tired long before I was, and asked that we call it off. I was ready to go on.

Still, the view was amazing.

The plan from Arches was to drive into Colorado as far as Glenwood Springs on I-70 (about a two-hour drive), and then head northwest towards Salt Lake City. We at least wanted to put our feet in Colorado even if we couldn’t spend longer than a few hours there.

The drive to Colorado was well worth it. It was our first time seeing the Rockies.

We got to Glenwood Springs, and then headed north on Route 13. It was by far the most beautiful road we traveled the entire week. A simple two-lane highway with a 65 speed limit and incredible landscapes.

We even drove through a town called Dinosaur.

We all left huge fans of Colorado. It’s a place we need to explore more in the future.

The real story of the day, though, was Stephen, who was a beast behind the wheel. He drove our trusty Jetta for 10 hours straight from Arches to Glenwood Springs all the way to Wendover, Nevada. This was us that whole time:

Just before our final stretch across Utah, we stopped at a 7-11 to stock up on supplies. When we told the clerk we were completely sober and buying this, she did a double-take. 

(Don’t worry Mom — everything else we’ve eaten has been vegetables.)

Finally we reached Nevada at 1am. In the morning we would wake up and drive nine hours to San Francisco. The trip is coming to a close.

The Trip — Day 5

We woke up this morning in Zion. This was the view from the balcony of our room:


We set off for a couple of hikes: Weeping Rock and the Narrows. Neither was challenging, but it was amazing to explore the canyon. It felt like we were members of some secret order, the select few who had been invited to stay there.


The hike to the Narrows took us on a trail along the Virgin River (who names these things?) sheltered by the steep rocks. We stopped by the river for some R&R:


And for walking sticks (or should that be logs?):


On the walk back we had an incredible moment. Standing right next to the path was a deer with two fawns. We stood feet away from them for about ten minutes without them looking at us once. It was beautiful.


As much as we loved Zion this is a road trip and we had to go. We piled back into the car — Stephen the day’s driving hero once again — and headed to Bryce Canyon nearby.

Bryce Canyon was beautiful and an entirely different kind of landscape.


The perfect backdrop for a triple-selfie:


Our time in Bryce was short — only 30 minutes. After Joshua Tree, Sedona, Grand Canyon, and Zion, we got it: nature is awesome.

So we drove west on I-70 across Utah, and Mother Nature quickly showed us up. The mountains of the south fell away and the Moab Desert emerged. Things began feeling very apocalyptic. As the sun was setting we pulled over to this stunning sight:


And this sunset:


Wow. We stood there quietly and took it in until the sun disappeared behind the horizon.

We kept on trucking. In the car Stephen played us dubstep mixes and bro-splained the tracks to Dylan and I. (I remain unconvinced but love his enthusiasm.) We screamed along to Tom Petty, the Yeah Yeah Yeahs, and Kanye. By the end of the day my voice was weary from all the scream-singing.

Hours later we finally pulled into Green River, our destination for the night. We sat down for a horrific meal at a diner, and sketched out the rest of the trip. The original plan had us going to Jackson Hole before making our way back to LA, but time was getting tight. 

After a lot of discussion we decided that the next day we would go to Arches National Park, briefly venture into Colorado, and then pull a U-turn back towards California. The boys wanted to see San Francisco, and so there we would go.

The Trip — Day 4

Today we traveled over mountains, through valleys, and across great plains to Zion. It felt every bit a pilgrimage, each landscape outdoing the one before. Stunning doesn’t even begin to describe it.


The day started in a foggy Grand Canyon. It was a huge, geologically crafted bowl of clouds. They billowed like liquid nitrogen from the canyon, and if you stood long enough the landscape would crack through. The depth was impossible to comprehend. I had to consciously tell myself that it wasn’t a matte background or oil painting to understand what I was seeing.


A friend in LA had told me that the north rim of the canyon was the best spot, so we set off on a four-hour drive around the south and east edges. As we moved around the canyon’s edge we would catch glimpses of its largeness. Each time we would quickly pull over and sprint to the rim for yet another look. It’s magnetic.

By the time we had reached the north rim it was getting late. We took a right instead of a left, and headed north to Zion National Park in Utah.

The drive was poetic. We drove along the steppe, beautiful red cliffs building a wall between us and the north. We crossed huge plains. Every inch was majestic.


The drive was also silly. We listened to music as loud as we could bear and played along in ridiculous ways. Dylan and I played both air bongos and air trombone out of our windows and toward the mountains. We hung our heads out of the windows like dogs, lapping up the fresh air and freedom.


Soon we crossed the border into Utah, tiny cowboy towns and gun-related slogans greeting us. And then we were there: Zion.

Zion first greeted us with pale, softly rounded rocks spotted with trees. The road serpentined between them in a way that presented them to us. “Look what I have brought you to,” it said. We craned our necks and pointed in every direction. “Look at that!” “Over here!”

Suddenly we arrived at a long tunnel, a mile long at least, and we emerged into a sight that I will never forget. Towering mountains of rock circling us like a protective huddle. They were colorful and textured. Reds, oranges, and grays. Smooth surfaces, grottos, rocky crags. Everywhere we looked was something we had never seen before.


Dylan and I hung our entire upper bodies out of the car as we crawled along the switchback road. We kept looking from the sky to the mountains to each other with slack-jawed grins. Zion. "Ten out of ten," Dylan said. "No, twelve,” replied Stephen.


We took a bus deeper into the park, and the landscape kept getting crazier. It’s the only time in my life I’ve been some place where I wouldn’t have been surprised to see a dinosaur. It would have completely made sense.



Because of the rain we were limited in how much we could explore, so we decided to stay in Zion for the night and see more in the morning. We were hooked.

The Trip — Day 3

Sunday, August 25th

Last night we drove from Phoenix to Sedona in darkness. This morning we opened our curtains to see Sedona for the first time. This is what we saw.


Incredible. Suitably awed, we sat down for breakfast. Stephen and Dylan spent most of it talking about video games, as you can see from Dylan’s blissed-out face:


We decided to go on a hike. Stephen came across a trail called Devil’s Bridge, which immediately settled all arguments for what to do next. The trail was amazing. In every direction there were huge mountains soaked in a deep red clay. The ground was the same deep red, and it was covered in cacti, trees, and other desert details.


The trail took us up one of the mountains, and each step gave us a better view of the valley below.


We didn’t even get lost.


Finally we reached Devil’s Bridge. Victory!


Stephen and Dylan celebrated.


And Stephen found time to play in puddles, which makes him happy.


The trail conquered, we hit the road for the Grand Canyon. We took 85 north, a beautiful road that winds up and down huge mountains and through a thick forest. It felt surprisingly like the Pacific Northwest. Arizona: who knew?


Out of the forest, we stopped for a late lunch in a town called Williams. The restaurant was straight out of Guy Fieri’s horrifying dreams. The bathroom used a car door to separate the urinal. Classy.


After lunch Stephen took over driving. Dylan sat shotgun. I marveled at what a weird world this is. We sang along to “The Funeral,” “Maps,” and a bunch of other songs. Dylan played “Where Is My Mind” and we all yelled “STOP!” at the right moment. I was a proud big brother.

Hours later we arrived at the south rim of the Grand Canyon. We parked the car, none of us having any idea what to expect. We rushed ahead. We were immediately overwhelmed. Wow. Even full of clouds, it’s stunning.



We decided to stay at the Grand Canyon lodge nearby. After checking in we visited the lodge’s college-style cafeteria for a game of Cards Against Humanity. The game’s most exciting moment came when a mouse suddenly ran along the railing next to us and others. But rather than try to trap or kill the mouse, everyone — us included — reached for their iPhones to film it. Sadly we were unsuccessful (and the mouse got away too). Rodents will thrive in this post-iPhone era.

It was a long and exhausting day, and we were more than ready to turn in. Tomorrow will bring more of the Grand Canyon and maybe even Utah. Wish us luck.