The Case For Anti-Optimization

The phone rang and it was the front desk. In broken English, the woman on the other line told me that someone was downstairs waiting for me. I told her I’d be right down. I’d been waiting months for this day. I let my wife know who it was and that I would be right back and then stepped out into the hallway. The hotel was a time capsule. The hallways and rooms have never known anything other than early 70’s decor. Roses covered the yellowing wallpaper that lined the corridor. The old hotel made me think of that movie The Shining; at any moment I felt that a little boy on his tricycle would come flying around the corner. But I’d have to settle for a maid with eyes that looked right through me and her cart full of yellowing sheets. The elevators also wanted to showcase their age by the rattling and popping as they slid up and down the twenty-story hotel.

I held my breath on the way down. Waiting for the elevator cab to come to a premature halt and trap me inside. But like most old things in Moscow, they worked surprisingly well despite a worn outward appearance.

When I got down to the lobby there was only one person standing there waiting. He quickly made eye contact with me and nodded. I saw the manila folder in his hand. He wore a knit cap and puff coat that was just moist enough to let me know that it was snowing outside.

He asked my name, very slowly and deliberately getting the question out in English. I told him. Then he reached out and we shook hands. He snapped up the manila envelope and showed me my name printed along the side. I nodded again.

“Traffic today. Snowing very bad. Here you go. Two tickets for the Trans-Siberian.” He said as he opened up the envelope and pulled out the tickets. “My girlfriend is in the car. She wants me to ask you, why do you want to take the train? Why not just fly? It’s less money, right? Faster too?”

I didn’t know what to say to him. Why I was paying more money to take a longer trip? It didn’t make very much sense, from a logical point of view. 4,735 miles by slow rail. It did sound impractical. I can see why he wanted to ask the question.

“Because it’s about the journey.” I told him with a sly smile, trying to indicate my use of the cliche.

“How long?”

“Seven days.”

His eyes widened, but his face remained stoic as if I’d given him some grim news. Then handed me over the two tickets and we shook hands again. I’d later regret not tipping him, but I was so excited and relieved to finally have the tickets I didn’t think twice about the Rubles stuffed into my pocket for that exact reason.

That train ride across the vast country that is Russia is something of a hinge between chapters of my life. A blur of strong Russian beer and books and hot tea. Daylight doesn’t last long in January in that part of the world, and the days were filled with sharp shadows and snow-covered forests that made me question my place and the order of things in the world. The nights were numbing star-filled affairs where it looked as if the entire galaxy had decided to drop down within a few feet from our cabin window so that we weren’t traveling under the stars but were amidst them as they billowed around us in a glowing shifting light.

Movement and sound never ceased on the train; a bump here, a clack there, screeching as metal rubbed unmercifully upon metal until the constant commotion of it became as natural as breathing. And when the train did stop, I yearned for it to start back up again and break up the unbearable silence. My body needed that rattle, that random jarring of joints and limbs. The commotion of the train became as comfortable as a warm blanket that never once let me consider that a deadly cold lay just a few feet from my protected cabin. Or that I was as far away from home in a foreign land opposite the world as I’d ever been in my life before.

There was no rush on that long ride through the expanse of Asia. The train was in no rush. I was in no rush. The world outside was in no rush. Even my wristwatch seemed to take it easy. Never did the minutes run off with the hours. I could gaze out my window for ages before a minute decided to pass. Conversations with my wife during this gap in time were like rivers; some conversations meandered around lazily till they aimlessly ran dry, while others raged like floodwaters overflowing with ideas and dreams like rapids marching towards the sea.

The photos are a bit blurry. This was pre fancy camera days.

Now and then we would stop in frozen villages to refuel and unload passengers. Each stop was like a visit to another planet. Before exiting we needed to suit up in layers and layers of clothes, just to waddle around enough to purchase warm food, pastries filled with questionable meat, beer, and cups of soup. At these stops, it was only a matter of minutes before my scarf would form ice from my breath. We’d wander around and gaze out at the Siberian forests or infinite steppe and wonder what life would be like to live in a place so remote and cold. What would happen if we missed the train departing and were stuck in this village? Where would we go? How would we communicate? For this reason we stood close to the trains and jumped aboard as soon as the crews waved us on.

When we finally entered the Gobi desert there were wild horses and camels grazing about the red landscape. And when we entered China, and man made structures again filled the windows, miles and miles of buildings, nameless city after nameless city, each filled with enough highrise buildings to cover San Francisco ten times over, I knew that I had just crossed over into another way of viewing. How could so many people live in these giant cities I’d never even heard of? Then finally we entered the biggest city yet, Beijing.

Forbidden City Beijing

Not till I stepped out of the train station and out into the hectic Beijing Central Station did I wake from the trance that the train ride had cast over my senses. It was as if I’d woken from a dream and was suddenly standing in the busiest place in the world. It may be the worst case of culture shock I’d ever experienced. Beijing is just so busy and loud. A kaleidoscope of people, color, and smell melding together and separating at every boulevard. I remember walking around in a daze, trying my best to get my bearings, holding onto a paper map as if it were a compass, constantly turning it, trying to squeeze some sense out of it. How I wished I could be back on that train and feel the gentle rocking beneath my body and the thick glass window beaming with empty Siberian countryside.

That was when I knew why I hadn’t purchased tickets from Moscow to Beijing with the purpose of being efficient. In fact, it was quite the opposite. Unbeknownst to me, till much later, I’d sought anti-optimization and loved it. I’d combined one of my passions, travel, with a slower, out dated, sub optimal method of travel.

Not everything needs to be optimized

I could easily have spent a day or two flying across Asia, saving time. This would have saved money too.

I bet if I ask a mountain climber if he or she would rather pay to have a helicopter fly them up to the peak of a mountain they’ve dreamed of one day summiting, just so they can save time and effort, they would likely laugh me off. Same if I ask a sailor if he or she would rather pay for airline tickets to cross an ocean, rather than cross by the wind alone at a measly 5 knots.

It’s not always about optimization and streamlining. In fact, I’d go further and say that optimization takes away a bit of the color of life. Is there something to be said about the space between the goal and setting out for said goal? Yes! This is where life is lived. It’s this time that separates one person from another.

There’s a joy in doing things the hard way sometimes. Especially doing things others can’t easily do. Anyone can buy a plane ticket to Europe, but not many have the skill or want to sail across an ocean to get there. The same could be said about retirement, it’s easy to coast from an early age to golden age saving 10% of an income annually for financial freedom, but not many have the want or skill to cross an Ocean by saving aggressively for a short period of time for early financial freedom.

Time and money are some of the most valuable assets one can have in life. But that doesn’t mean we need to constantly look for ways to save and hoard these assets. After all, what’s the point of an asset? In my view, the point of an asset is to have the ability to wield power over our lives and allow us to have more options to pursue the things we enjoy.

There’s a reason people choose not to optimize when passion is involved. Anti-optimization is the key to slowing down the things we love in life. It’s a way to get lost in the weeds of life.

Anti-Optimization goes against the grain of our fast consumer culture. Where technology reigns and the speed and ease at which we can do things are thrown on a pedestal and glorified as progress and working smarter not harder. It might be an easier life to streamline chores and speed up our days with less struggle. But what kind of life is that? Is saving time and eliminating challenges the optimal life for us humans?

Sometimes the least time-efficient way to go about something is the most efficient way to go about life.

What about you? Do you ever take the long way on purpose? Is there anything you enjoy doing that could be done faster and cheaper?


I use Personal Capital to track my expenses and net worth. I recommend using them if you are on your FIRE journey or just want an easy way to track your expenses. This is an affiliate link…which means you’d help me out if you click it and sign up.


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