e were cruising down the most northern stretch of California 101 before entering Oregon. Our day began encumbered by light fog and rain, but it burnt off by lunch time, giving us clear views of the shores below. The cliffs alongside us dropped into the ocean and rocky crags jutted from the sea in the distance.
Traffic slowed to a stop. To our surprise, the road was only open during two one-hour time slots that day due to construction. We put our car into park behind a long line of others and waited for the floodgates to open.
Most people passed the time walking up and down the left side of the road where there would normally be oncoming traffic. There was a woman being dragged by her giant German Shepherd in every direction. And a middle-aged man leaning against his beaten-up pickup while having a smoke. The bed of his truck was filled with logs and sported Arizona plates.
As we sat stationary and without cell service, I reflected on the 1,000-mile journey we were about to complete, having driven along the California coast from the southern border with Mexico to the northern border with Oregon over the course of a month.
When we initially made plans to visit California, I told myself that we added The Golden State to our itinerary because it’s supposed to be beautiful and have a plethora of amazing food. It wasn’t until the end of our journey, sitting stationary on the highway, that I dug deeper into my subconscious motivations.
I realized that California has always intimidated me.
I grew up in a time where pop culture was centered around Hollywood and the many famed filming locations across the state.
I work in tech, where industry culture has told me that I’m an inferior software engineer since I don’t work in Silicon Valley.
I’ve lived in a time where California’s economy has thrived and the news is filled with stories of the state having the highest gas prices, real estate prices, startup exits, IPOs, etc.
In many ways, California has always felt more to me like an idyllic setting in a movie than a real place.
Our trip across The Golden State was my chance to demystify the intimidation factor of California and finally put myself into perspective within the great state. Is it all it’s built up to be? Am I good enough to live there? Could I fit in? Do I want to?
California, here we come.
Our adventure began skirting the Mexican border. As we crossed an endless dessert interrupted only by a few pockets of sand dunes, “The Wall” came into view. It was black, and while I know that it’s actually quite tall, power lines supported by giant towers running parallel to it made it look small in comparison.
An RV was parked in one of the unofficial pull-offs next to the east-bound lanes. They had erected a 50-foot flag pole next to their camp, which flew both a black & blue American flag and a Trump flag. I have no idea how they managed to erect such a tall, temporary flagpole in dry, sandy soil.
The monotony of the desert persisted a while longer, but the hills near San Diego came on quickly once we reached them. We skirted around downtown until we bisected Highway 1, then we turned our car north and continued up the scenic route. Each town along the coast north of San Diego felt like its own hideaway, tucked into bays and behind mountains. Most coffee shops didn’t open until 8:30am or 9:00am. Before and after work, surfers parked their cars lining every inch of the streets, then jogged down to the beach in their wetsuits.
I always thought California was called The Golden Coast because people there were rich. I knew after one sunset in La Jolla that the term actually refers to the golden color of the sky and seaside cliffs during twilight. We get colorful sunsets in Colorado, but I’ve never seen gold in the sky’s palette. It was like the entire landscape was a chameleon changing color to harmonize itself with the sand.
As we headed north, I enjoyed a sense of adventure and discovery whenever we entered new towns. Each place was unique and special—almost like it had its own cult following living within the city limits. It felt like every person had made a deliberate decision to live where they do, and that they were proud of it.
I’m from Colorado, which most people associate with the mountains. It took me driving up and down the cliffs along the California coast to appreciate how flat the Front Range really is (where most people in Colorado live). I know now that I’m from the plains, not the mountains.
A few times I could have convinced myself that we were driving on a Mario Kart track, going up, down, and around all the hills. The road would flatten as we entered a downtown strip encircled by chic bungalows and trendy restaurants, then take off again a mile later, twisting and turning toward the next destination. I liked how the geography along the coast gave each town a sense of place and seclusion. In a large and chaotic world, there’s something comforting about being somewhere and only being able to see that place rather than an endless expanse of houses and buildings that gradually disappear into the hazy distance.
We (unsurprisingly) hit traffic driving through LA in the early afternoon on a Friday. About an hour into our 90-mile, south-to-north journey across the city, we were inching forward, one tire tread at a time. Our GPS map was gashed with red lines, indicating heavy traffic in every direction.
As I assessed the lamentable reality of our situation, I noticed that we were driving through Compton. I knew of Compton, but my knowledge about it boiled down to the sum of half-a-dozen rap songs. It’s supposed to be a rough town, I knew that much. I looked around, but there wasn’t much to see from the highway. Large walls obscured most of the view. Then a red convertible sports car zoomed past us with the person in the passenger seat standing out of the car, holding his phone above his head and hollering at his live-stream audience. “Ooooh, ya!,” the man shouted over their blasting radio. A few cars later, a Lambo with dark tinted windows passed, it’s engine purring with each stop-and-go tap of the gas pedal.
We emerged from traffic into northern LA, which felt like driving through a Jeopardy question—”What is a wealthy town referenced in pop culture?” Malibu. Beverly Hills. Hollywood. Bel Air. Way up on the cliffs overlooking the ocean we could see massive buildings. Shelby asked if I thought they were hospitals or universities. I told her I thought they were houses. We looked it up. The most expensive property sale in 2020 across the US was a 100,000-square-foot mansion in north LA that sold for $340M, which was below the estimated $500M the developer thought they could get for it.
I thought it was interesting that from the balconies of this $340M mansion, you could likely see Compton.
Santa Barbara came next. Compared to the congestion of LA, Santa Barbara felt rural. Houses flowed up and down the hills to the east, but the downtown strip was quiet and quaint. When I asked my friends for food recommendations in southern California, I was surprised that so many of them mentioned a place called La Super Rica in Santa Barbara. There was such a strong consensus, I knew we had to eat there.
The man who took my order at La Super Rica was a bit melancholy when I first approached the counter, but he perked up after I asked him what his favorite entree on the menu was and ordered it. Everything was delicious.
A sharp turn just outside of Santa Barbara sent us up into the mountains. I once again underestimated California and expected the mountains to be “mountains” (aka hills). I could not have been more wrong. These were steep and prominent mountains. The peaks in Colorado sit high above sea level, but they also start high. In terms of prominence, it felt like the mountains we climbed were larger than many of the peaks along the Front Range. At the top of the pass, we were greeted by one of the best sunsets I’ve ever seen. Explosive in color, mysterious and layered in visibility.
Our next stop was Pebble Beach, where we met my parents, grandparents, and uncle for a few days of golf. It’s difficult to describe what it means to a golfer like myself to play a course like Pebble Beach, but what I can say definitively is that the course itself lived up to every one of my expectations. The scenery was gorgeous, the layout of the course is unquestionably one of the best I’ve ever played, and each hole felt like I was walking through a piece of golf history. I’m so thankful I got to play the course with my family. It's a day I’ll cherish for the rest of my life.
Pebble Beach Golf Links sits on the 18,000-acre Pebble Beach property that’s home not just to Pebble Beach Golf Links, but four public courses (Pebble Beach, Spyglass, Poppy Hills, and Spanish Bay) and two private courses (Cypress Point and Monterey Peninsula). Cypress Point and Pebble Beach were both designed by Alister MacKenzie, who is considered one of the best golf course architects of all time. MacKenzie also designed Augusta National in Georgia, where The Masters is held each year.
I don’t know this from personal experience, but both Cypress Point and Augusta National are said to be so exclusive that money alone can’t buy you a membership. Even Tiger Woods can’t use the massive fortune and ubiquitous fame he’s built to make a phone call and purchase a membership at these courses. In fact, rumor has it that if you inquire to become a member, you’re almost guaranteed to never get an invite. You have to be rich, and then you have to be recruited into the club.
These courses are clubs in the truest sense. Old-fashioned clubs. Both Cypress Point and Augusta National didn’t allow black or female members until recently. In fact, in 1991 Cypress Point made headlines when they refused to change their membership rules to comply with PGA Tour guidelines and chose instead to give up their eligibility to host tournaments. They still haven’t rejoined the tour circuit.
The Pebble Beach property was first developed in 1880 when a group of railroad tycoons purchased the land and built a high-end hotel near the shores of Pebble Beach (an actual beach). Over the decades, the land was developed with half a dozen golf courses, over 100 houses, and several hotels. Ownership has passed through the hands of Twentieth Century Fox (who used profits from Star Wars to buy the property in 1978), a Japanese investment group (who bought in at the height of the Japanese asset bubble in the late 1980s), and a group of private investors including Arnold Palmer, Clint Eastwood, Richard Ferris, and Peter Ueberroth (1999).
The Pebble Beach golf course was great, but the vibe of the resort it lives inside of felt like a “prestige onion.”
On the outside of the onion were the people who buy a day pass onto the property for activities such as coasting down 17-mile drive, peeping at the famed Lone Cypress, eating lunch at one of the resort restaurants, and swimming at one of the beaches. The next layer inward are the golfers like us, who fork out >$1,000 per night to stay at the hotel (required to play the public courses) and ~$500 per round of golf. Peel another layer, and you get to the people who are invited onto the private courses by friends and business partners. Then there are the Monterey Peninsula members, the less prestigious of the two private clubs. Then the people who also own one of the many gated mansions with supercars lining the driveways. And at the core of the onion are the veritable individuals with not just the money, but the status to be invited to join Cypress Point.
I felt uncomfortable being encircled by so many layers of access and status. I was constantly unsure of where I was allowed to be, and never felt like I belonged wherever I was. When I interacted with people, I found myself analyzing which layer of the “prestige onion” we each fell into. Perhaps this is a personal issue—an insecurity rooted in the intimidation factor of California that I was confronting. I don’t think it was entirely me, though.
Back to the fun…
We had all the iconic, bucket-list moments you hope for when you visit Pebble Beach, but there were three stories that stand out as unique and interesting to read about.
There was the time we were walking Skutull after dinner and a doe started following us. At one point, she approached to within ten feet and was aggressively chasing us off. I assumed she had babies nearby because I’ve never seen a deer behave like that before. The funny part was that despite Shelby and I picking up our pace and constantly looking over our shoulders, Skutull remained blissfully unaware of the deer throughout the entire experience. We can hide his toy under down comforters, behind couch cushions, and even inside the refrigerator and he’ll sniff them out in seconds, but he had zero perception of the wild animal threatening to attack us.
Then there was the motley crew of teenagers in the pro shop as I was checking in for our round. They each purchased a Pebble Beach branded scally cap, then swaggered toward the first tee box wearing their new hats and puffing their chests. “Pebble-mother-fucking-Beach mother fuckers,” the scrawny kid at the front of the crew said to his friends in a forced deep voice. Their undirected scowls made them look like a crew of English gangsters.
The funniest moment came on hole 9 at Pebble Beach. My grandpa is hard of hearing, can’t see out his left eye, and often falls short of breath because of his emphysema. Hole 8 was hilly, so after he made it back to his handicap-flagged cart and parked it near our tee box, he took a moment to catch his breath while the rest of us hit. Grandpa didn’t notice when a ball from the group behind us settled in the rough behind his cart. The golfer approached his ball and tried asking Grandpa to move, but Grandpa didn’t see or hear him. The guy smiled at us when we told him that Grandpa’s hard of hearing. “I’ll get a little closer!” the golfer said with a wave.
Then from fifty yards across the fairway one of the groundskeepers started yelling belligerently at Grandpa, waving his arms in the air, “Move! Get out of the way! What the hell are you doing!”
The golfer froze.
When Grandpa didn’t respond, the groundskeeper dropped his tools and began stomping towards him, continuing to yell. He had white hair, but got around pretty well. I’d guess he was in his sixties.
“I can’t hear you!” Grandpa told him when he finally noticed the man shouting.
“Do you speak English! Get out of the way!” the man yelled.
“Kiss my ass!” Grandpa yelled back, engaging the gas of the cart and steering toward the man.
“Come over here and I’ll kiss it!”
As Grandpa chugged down the cart path at the absolute minimum speed you can make a golf cart travel, one of the other course employees ran over to the angry groundskeeper. There was some shouting, and then the groundskeeper jumped in his cart and drove off. By the time Grandpa made it to the other side of the fairway, the groundskeeper was gone and the other employee got to have a piece of Grandpa’s mind.
“Don’t mess with Gramps,” the golfer from the group behind us said laughing.
“Sorry!” we told him.
At least he could hit his shot now.
Skutull visited the beach sporadically throughout the southern segment of our California adventure, but it wasn’t until we stayed a week near Santa Cruz that he leaned into the Beach Dog vibe.
We lived walking-distance from a beach, which Skutull and I ran on every morning. Our house was located outside of town and the beach near us had signs everywhere warning us not to swim because of strong rip currents. The combo of rural and unswimmable water made this beach nearly private—most mornings we didn’t see anybody else.
I’ve never lived close to a beach. It was relaxing. The waves were much louder than I remembered, but they weren’t loud in a disturbing way like a jet engine. They were soothing. Every time Skutull and I stepped off the trail into the sand, it felt like the beach took control and told me that there was no need to say anything, just be.
I found a driving range near our house in Santa Cruz. It wasn’t anything fancy, nor was it attached to a golf course—just an old-school driving range lined with giant nets.
To the average person, I probably look like a pretty good golfer, but among good golfers, I’m not that good. I didn’t play in college, nor did I ever have even a remote chance at going pro. I say all of this because on two separate trips to this driving range, I had multiple people film me practicing and ask if I was a pro. Even though the praise was unwarranted, I’ll always remember the driving range where I was famous.
We visited family and friends in Palo Alto on our way further north, which was a lovely area. Near perfect weather. Tons of great food. Stanford. Lots of good jobs. Not too crowded, but close to SF if you want to do city things. I can’t comment on the affordability issue I’ve heard exists since I don’t know much about it, but removing cost considerations, the area around Palo Alto seemed like an incredible place to live.
Next, we landed in Sonoma for two weeks, where we found ourselves in the thick of utopia—beautiful landscapes, amazing food & wine, friendly and laid back people. If it weren’t for the wildfires, Shelby and I might live there.
One interesting thing we learned in Sonoma is how challenging the wildfires are for vineyards. Obviously it’s an issue if the vines themselves burn, but I had no idea how sensitive grapes are to smoke. We did a private tour with a winemaker and got to ask her questions about the wine-making process and lifestyle . She told us that grapes can only withstand a few hours in smoke before they’re tainted and the entire year’s harvest is lost.
We lived in Sonoma in mid-April and there were already several small wildfires nearby. In fact, we stayed in a house that looked out over a vineyard and one of the mornings we woke up to smoke that had settled into the valley. It must be stressful living with both your craft and livelihood perennially at risk of not just fire, but smoke, hail, frost, drought, and a million other ways Mother Nature can destroy what she grows.
One of the biggest challenges we had to tackle during our time in California was getting our second COVID vaccination. We stopped in Cortez, CO on our way to California to get our first shot, but the vaccination system wasn’t set up for nomads. Most places (at least at the time) required that you get both doses at the same location. I spent a lot of time unsuccessfully attempting to book our second shots at various pharmacies across California. At one point, I almost gave up and looked into how we could get back to Cortez, CO from Northern California. It didn’t look cheap or easy. Especially considering the fact that Skutull can’t fly easily, so Shelby and I would have had to go separately while the other stayed back with Skutull.
Then I had a breakthrough with the help of one of my friends. At the time, Eureka, California was one of the counties in the US where a disproportionate number of people were declining the vaccine compared to the supply. It was the same story in Cortez. When I spoke to people in the pharmacy at both locations, they said they were throwing out unused doses most days and were happy to vaccinate anyone even though the official guidance from the CDC was still “60 and older.” I’m not convinced we didn’t get lucky with a glitch on the CVS website, but we managed to book our second shots, lifting a monumental weight off my shoulders.
The biggest downside was that the pharmacy we booked our shots at only administered one second dose per day, which meant Shelby and I had to go on back-to-back days. We shortened our stay in Sonoma by a night, booked a room in Eureka, and drove North. It felt like a chance to put not just our own vaccination stress behind us, but hopefully the beginning of the end of the pandemic.
We took advantage of our night in Eureka by visiting the nearby Avenue of the Giants. The white noise of the ocean near Santa Cruz crashing into the shore made the beach peaceful, but the total silence of the redwood forest had a similar effect on me.
The size of the trees was impressive, but that’s not what I’ll remember most about the redwood forest. I’m the type of person that’s always in my own head—thinking, planning, having conversations with myself—my mind wakes up racing and doesn’t stop until I crash at night.
The redwood forest was a rare spot where my mind naturally quieted. Where I instinctively connected with my surroundings and couldn’t do anything but feel the Earth beneath my feet and appreciate the indescribable connection we humans occasionally feel with nature.
If only I could feel that way every day.
I wrote recently that Santa Fe felt like a place I could go to hide.
California felt like a place I could go to be noticed.
From the glamour of Hollywood’s entertainment industry, to the dominance of Silicon Valley’s technology sector, to the prestige of Napa Valley’s food & wine—there is a way to make a name for yourself in just about any way you can imagine.
Now that I’ve spent time living in California, I can understand the draw of the state. It is truly beautiful and the lifestyle you can achieve seems utopian.
I don’t think anyone can argue that California lacks opportunity, but there are two types of opportunity I’ve observed in my life:
The first type is internal. This is when the universe gives you an opportunity to explore, express, or share a part of yourself.
The second type is external. This is when the universe gives you an opportunity to alter the external forces that affect your life.
One type is not better than the other, and if internal opportunity is black and external opportunity is white, then the world exists in shades of gray.
The surgeon who feels fulfilled by saving people’s lives (internal) is also regarded highly within their community (external).
The songwriter who finds purpose expressing their emotions through music (internal) may also become famous (external).
The business person who acquires evermore wealth and prestige (external) also wants to ensure their family will always be safe and cared-for (internal).
This is a self-assessment, not a blanket statement: in California I felt disproportionately pushed by external opportunity over internal. I wanted the mansion in Pebble Beach. I yearned to tee up on the links at Cypress Point. I pictured myself walking down a red carpet in Hollywood as fans cheered in awe. I dreamed about a company I founded building an idyllic campus in Silicon Valley. I browsed online real estate listings in Napa looking for a vineyard.
I know that external opportunity is what drives capitalism, and I’m not against capitalism, but by the end of our time in California, I felt stressed and exhausted by my perceived excess of it. External opportunity can be incredibly motivating, but it also sows pressure. Especially when such a small percentage of people make it all the way to the top of the ladder, yet the top is always in view, taunting you to push harder.
I’ve decided to call this observation The California Grind.
The Grind can be rewarding. There’s evidence of wealth and fame all over the state, from the cliffs of La Jolla, to the bungalows of Santa Barbara, to the hills of Los Angeles, to the tech valleys near San Francisco, to the vineyards of Napa/Sonoma. If you make it to the top, paradise awaits. But you have to face The Grind to get there. And not everybody that deserves to conquer The Grind succeeds.
My observation of The Grind also helped me demystify the intimidation factor of California by humanizing it. I realize now that most people in the state weren’t born inherently rich, successful, or abnormally intelligent. They battled The Grind and got lucky enough with timing, collaborators, etc. to climb to the top. In that regard, California intimidates me much less than it used to because it makes sense—if you excel at what you do, California is where you’ll earn the largest external rewards.
When the line of cars on Highway 101 finally started moving toward Oregon, I was surprised that the feeling I had as we departed California was one of relief. I had a lovely time in the state. I truly did. But I was eager to escape The Grind.
I think it would be fair to call me weak in that regard. It felt a little like I was running from a fight. If I learned one thing about myself in California, it’s that external opportunity motivates me, but I’m happier with a balanced mix of external and internal opportunity.
I’ll be a repeat visitor to the gorgeous, diverse, and (mostly) friendly state of California, but I can’t decide if I’d ever live there. I think I could survive The California Grind. My career might even thrive in it. But I’m not sure it’d make me happy. I worry I’d get sucked in too far and swallowed whole.
According to Skutull
Skutull discovered the Beach Boy inside of him during our stay in California. He still probably prefers a nice lake to the ocean because it’s easier to swim in, but the beach was unquestionably a hit. He thought the sand was fun to run in and liked to chase the waves up the beach after they crashed.
Skutull also got to check an item off his bucket list—ordering off a menu at a restaurant. The Stationæry in Carmel by the Sea had a dog menu. Skutull ordered the Puppy Chow—a medley of ground beef, brown rice, and multi-colored carrots—with an egg on top. Skutull has good manners at restaurants and has never been given food, so he was pleasantly surprised when the waitress set a bowl of food down in front of his face. He ate laying down with his tail wagging and paused several times to look up at Mom and Dad and double check that what he was doing was okay. He finished his food, got up and gave Dad a single kiss right on the lips, then plopped himself back down on the sidewalk for a nap.
To Skutull’s dismay, Mom and Dad insisted on giving him a California name, Sku-vino, which he liked more than his Southwestern name—Sku-tija. He’s hoping they don’t continue this naming habit for every leg of the trip…