Reflections from Walking 400 Kilometers

“There’s nothing more human than walking.”

Tamir and I sat alone in the cafeteria as he downed another spoonful of lentils. “We’re designed to walk long distances. We were meant to journey.”

A sandstorm had turned the sky orange around us. I was 70 miles deep into the Negev desert on the Israel National Trail, and I had reached Neot Smadar just in time. Neot Smadar is one of the last remaining true kibbutzim — communal farms where each member gives everything they can and gets everything they need.

As a hiker, I was allowed to volunteer and stay for a day to experience the community. For me that meant helping in the vineyard following by washing dishes at the rest stop.

It would be another 180 miles before I could truly look back and appreciate what Tamir had said. My legs were begging for rest and my brain for indoor, sheltered sleep.


“Dude, if it’s not fun, then why are you here?”

I was done. I was totally burned out on coding, startups, Hacker News, retweets, Google Analytics… all of it. I tried to move over from being CTO to marketing, but burnout is burnout.

Coding alone, 8–10 hours a day, with ten time zones to protect me from distractions, started off as a productivity dream. But over time as I learned that is entirely unsustainable for any mind to endure. Coding to me was always a means to an end — a stimulating, interesting means — but still just a means.

Successful developers I’ve met love the journey. In contrast, I loved the destination. Rather than seek the intellectual challenge, I’d jump on the chance to do things the easy and “boring” way if it got the job done. Solving problems was fun, but my satisfaction came mostly from seeing people use (and holy smokes, pay for!) something that started in my imagination.

As in all technology startups, Ecquire hit an innovation inflection point — the idea worked and operated, and the big challenge ahead was to make it work… better. To make it more robust. To have grown-up processes. To optimize. Release features that were valuable to small pockets of users. And all along the way, the product would look pretty much the same.

Still today I I don’t know what did me in the worst. Was it the feeling that everything came down on my shoulders? That any wasted time was wasting everyone’s time? Was it that my best contribution was to simply “shut up and code”? Maybe it was the endless stream of support tickets, and that I treated each customer interaction as my personal responsibility.

I also worked wrong. I should have turned off my laptop more often rather than look for the next task. Easier said than done, but it’s no surprise one of the top deathbed regrets is “I wish I hadn’t worked so hard.”

All together it stopped being fun.

The effects were clear. I stopped waking up excited. I found myself vetoing new ideas that required work. I could clearly see I’d become less creative — less excited about the future and changing reality. Less excited about anything really.

With work no longer fulfilling, my motivation to pull through was abstract and financial. When my only motivation was money, it only took a few weeks for me to crack.

Paul and I agreed I needed out; I was doing more harm than good to the company and the culture by just being around.


It was time to walk. My gut was sending me an unusually clear message: “pack a bag and start marching.”

I knew exactly what that meant. The 621-mile Israel National Trail, a path that meanders from the Red Sea up to the Lebanese border. No plane ticket needed — just a few hours bus ride from Tel Aviv to the southern end of the trail (and the country) in Eilat. It was spring, which meant the smart choice was to start with the desert half.

The Negev Desert of Israel is a collection of geological and ecological wonders. Every 30 miles you enter a different world than the one before. It’s also some of the hardest long-distance hiking terrain around, with steep water-carved canyons, enormous craters, and slippery chalk ledges.

Water is a challenge to say the least. The average desert hiker needs 6 liters of water per day (about 13 lbs.) and at many points you have to walk two days between sources of drinkable water. Your options are either to carry 26 lbs. of water on your back, rely on the kindness of passing vehicles, or cache water ahead of time (and hope no one finds it first).

The idea of walking for days in the desert with no cell phone reception sounded like a luxury spa for my mind.


I started walking from Eilat on March 17. As did apparently, twelve other hikers that day — the first of many dozens of people I would meet on the trail. Being alone was possible — but it would take a conscious antisocial effort.

While I set out seeking to heal my mind, it was clear that meeting people along the way was therapeutic to the soul.

For the first time in a long time I was listening. Maybe it was the remote location or the abundance of time, but I caught myself acting very differently than in my daily life. I had the space and time to be genuinely interested in the people I met, the depths of their personal history, and the energy to share from my own.

Whether other long-term hikers, weekend travellers, or people I met in settlements along the way, everyone was welcoming and to me, fascinating.

I discovered something way more enjoyable than the Facebook timeline, my Gmail inbox, and the New York Times: I discovered individual people.

In fact, the best part of the Israel National Trail is the people you meet. And it’s not just the other thru hikers: every few days in the desert section there is some kind of town or settlement, and in nearly every place there are “trail angels” — people who are happy to give what they can to make your hike a bit more pleasant. Some can provide a couch to sleep on for a night, some a hot shower, others a cold beer and a faucet to top off your water.

These people are not wealthy, and they are generally not pursuing high powered careers; I would say they are the best of our society. They have discovered — and have the courage to act on — one of the secrets to happiness: giving. True giving — to strangers, who can give you back nothing, and personally. I was just one of a stream of hikers this spring, and they magically made me each person I met felt equally and deeply welcome. I have utmost admiration for people who can make total strangers feel truly at home.

There’s the official angels — those that published their names and phone numbers — and the people along the way that simply do angelic things. Like the drivers who picked me up off middle-of-nowhere roads, the jeep travellers who wanted to make absolutely sure I had enough water, and the families on camping trips who invited me to join their meals.

Hiking the Israel National Trail (the shvil) makes you a shvilist in Hebrew. Being a shvilist is an amazing social position. I don’t know any other point in life where you can simply join a community for a day or two, feel completely part of it, and leave the next day, no questions asked. You are instantly accepted and are legitimate given your well, appearance. People you meet on the trail who are doing day hikes will always ask if you have enough water and food, and if you want any of theirs. Communities and individuals along the way want to make sure you have everything you need and to feel completely comfortable.

And the other thru-hikers…wow. What amazing people. People from backgrounds I’d never met before, with stories and aspirations that made me see my own life differently. It’s a higher level of friendliness than any other “place” I’ve been.

Israelis are known for being warm and easy to connect with — but on the shvil it’s on steroids. Many times I’d run into can another traveller, and minutes later be sharing food, coffee, searching for water, or walking miles (or days) together. It was totally normal to walk up to someone who looked like they haven’t showered in days, ask “Shvil israel?” and dive into a conversation about their life story.

The key decision I made was to set out as an individual rather than a group. I am not exaggerating when I say that being on my own gave me superpowers. I could go with the flow, join groups, leave groups, stay a bit longer or leave faster. I could walk alone all day and still make camp with ‘old friends’ at night. Most importantly, I wasn’t just constantly “outside my comfort zone” — I entirely redefined it.

What was truly amazing was how everyone on the trail generally knew about everyone else, even those that started on different days. Everyone passed or met everyone else at some point and group nicknames became pretty consistent (The Walnuts, The Badasses, The Reds, The Klezmers…). Twice it happened that I met people for the first time, but we already knew all about each other.

Taking a step back, I realized I wasn’t just cruising across the natural landscape of Israel. I was also walking diagonally through layers of society. Hiking and living with people from age groups, ethnicities, and geographies with whom I normally wouldn’t even ride the same bus.

I could use this space to list my adventures with Bedouins, bomb threats, and military aircraft, but those stories are cheap when set next to the experience of the people of the shvil.


My time alone, however, was the luxury mind spa I had hoped for.

Each morning at sunrise, I would pack up my sleeping back, eat an apple, and start marching. As soon as I would get into the rhythm of walking, I fell into a kind of flow. It was the perfect combination of being physically busy without being mentally busy. Time would fly by — not in hours — the sun seemed to glide overhead from east to west. A kind of meditation that came far more naturally to me than sitting perfectly still or focusing on breathing.

I had no idea what was going on in the world — no access to Facebook, news, radio, email. Nothing to process out of turn except the occasional lizard darting past. Nothing to consume except a feed of wadis, cliffs, mountains, and birds. The only thing I had to remember to do was drink water.

Step after step I would march while thoughts cordially entered my consciousness in a very ordered manner. I felt a new kind of control over my attention. I could revisit memories, questions, and try to figure out the world. Once I got in shape this worked even better as I walked uphill. As long as my body was busy — but not too busy — my mind was free.

Sure, I lost the trail quite a few times this way, but the extra few kilometers were worth it.


There’s something about the tech industry that’s uncomfortably messianic. Today is a grind, goes the thinking, but one day you’ll have an exit. You’ll sell your company for millions, all your problems will go away, you’ll have total credibility and respect, and everything will fall ito place. It’s like buying a lottery ticket every day for four years. And like the lottery, it’s worse than religion because there’s actual living breathing proof of the messiah — ‘exited’ entrepreneurs strutting around, giving talks, dabbling in investments, and being treated by everyone else as prophetic.

This why anyone who’s lasted more than a month in technology (and especially those who’ve hit home runs) knows that money can’t be the motivator. But even if you know this, you can’t help but fantasize a little about the happiness just a little bit of wealth might solve.

On the trail I felt like a millionaire every day. It was hot, it was hard, the food was monotonous, but I was very happy. I discovered plenty of little luxuries: showering with less than a liter of water, splurging on lentils the night before reaching town, discovering a can of tuna left by previous hikers, finding a sandy patch in a dry riverbed as a luxury mattress — and of course, peeling off my socks in the middle of the day. All those, plus the company of resilient, positive, profound people going through exactly the same thing. Who can ask for more?


I fell in love with backpacking just four years ago when a friend and I hiked the springs above the Dead Sea. It was the first time I realized I was carrying everything I needed in life on my back. I could walk in any direction I wanted, plop down and sleep wherever I ended up that day. It was a feeling of amazing personal power that no amount of money can provide. Just the opposite in fact.

On this hike too, it felt excellent to own two pairs of socks and underwear, and feel the freedom from stuff. It was an easy adjustment to living by sunrise and sunset, to eating several small meals a day, to measuring time not by money — but using water.

To be tired was to be truly physically exhausted. My body slept better than my mind. The nights were cold and the rocks uncomfortable, and I would wake up often. At the same time, I somehow dreamed harder and more vividly than I ever before.

The adjustment was so easy and natural that something about it was clearly true and right.

I can’t express how I felt other than the word healthy. In daily life sure I ran and ate well, but most of my time was spent arched over my laptop, indoors, moving very little. By medical standards I am thankfully a healthy person. But it was only now, at the end of each long day, no matter how much pain my feet and legs were in, no matter how cold or hot I felt, that I felt healthy.


Two days from Arad — the conclusion of the Negev Desert portion of the trail — I stopped in Dimona to rest. I called my girlfriend, then my dad, and then Paul. He painted a picture of where the startup was — surviving thanks to Adrian’s heroic efforts and clearly his own resilience. But surviving was not the goal — and having me pitch in alongside them would make the difference.

My gut churned a little bit over the next 25 miles.


Back in Neot Smadar with Tamir, I had long finished my food and I was just hanging around to see who would walk in. Eli sat down next to us. I had spent the morning working with Eli in the kitchen of the rest stop. I learned that Eli, a woman in her mid seventies, was one of the founders of the kibbutz in the late eighties.

Eli has no retirement plan and no assets. Not even a car. She continues to live by the principles of giving her all, and taking what she needs. Even though we’d spent half a day together, her energy level in filling orders back in the restaurant made me assume she was twenty years younger.

During my days volunteering on the kibbutz I acquired a sense of scale for what it would take to found such a place. The amount of work to set up the place — and the strength of the culture and community required to make it happen — simply dwarfed anything I know from the tech world. No matter what people say about their company culture, few if any “founding teams” could set up a successful, thriving communal farm deep in the desert.

I asked Eli, “I’m in awe. I just can’t comprehend how such a place gets started.”

Her response was quick, “That’s actually the easy part.”

What? “It’s easy to start something even if it’s physically and emotionally hard. There’s a clear goal. There’s a common challenge. There’s something to strive for and a dream to realize. It’s once you achieve the goal that the hard part starts. The challenges may be smaller but the motivation isn’t as easy to see… I think being one of the ‘founders’ is an odd title. I see everyone who lives here as founding this place every single day.”

I asked about her personal commitment to living here and everything she “gave up” by modern standards.

“You know, I don’t know what any of us really want more in life than the chance to work hard in a group with good people. What more is there?”


On the way to Arad I heard Eli over and over in my head. Tamir was right too. Humans were meant to journey — but we ultimately find meaning in working with others on something we believe in. I feel extremely fortunate to know both experiences very well.

In Arad I had three chicken sandwiches, a bottle of Negev porter, and slept about 11 hours before getting on a bus to Tel Aviv.

I’m not going to lie and say I’m excited to come back to the big city, where all my stuff is, and sit in one spot with a laptop. Catching up on new companies and tech industry news, I found myself watching from the sidelines, like in third person. For all its excitement and speed, the tech startup world felt a less important to the world, less serious, less meaningful.

I definitely had to dig a bit deeper to ask myself “why.” But maybe that’s taking the privilege too far, and I should just appreciate what I have. There’s good work to be done, and a great team to do it with.

Good team or not, I have to learn to just….work….less. My track record here isn’t very good, but that’s okay. If all else fails, I can just take a hike.