Reflexions on m 27th Year

It seems like the years follow a cycle of change and stability. Last year was relatively quiet. In 2013, not much happened apart from enjoying the ride. 2014 was different and can be broken down into three parts.

The year itself started as a continuation of the theme of 2013: Enjoying experiences and the joy of life. I took my parents on a trip to Hawaii and followed it with a winter full of skiing including a trip to Park City which turned out to be an incredible skiing experience with great people.


Part 1: Leaving Instagram

Early in the year, I wrote in my journal: 

I still feel scared. For years I've wanted to start my own company. I can't sit here for another 2 years and find myself looking back in regret.

Coming into the new year, I began asking myself hard questions about where I wanted to be and what I wanted to get out of my time, and I wasn’t able to answer them within Facebook & Instagram. I had a great run of personal and career growth in my time there but it stopped, and my attempts at restarting it sputtered. Eventually, the opportunity cost of time became too great, and a choice of how I wanted to spend my time became necessary.

It wasn’t an easy decision, and took a few months of mental gymnastics, back and forth, questioning and re-validating assumptions. I’m sharing the following journal entry, also written in the early months of the year, to give you a sense of the internal struggle:

To describe the past week as a roller coaster ride would be doing a disservice to the thrill engineers of the industry. I go from the deepest, most gratifying sense of self satisfaction to a deep pit of fear, anxiety and distress. Right now I'm at the bottom. My stomach feels empty, my brain has been buzzing since 7 in the morning, unable to focus on anything but the single issue: What the hell am I thinking?

At this moment, I'm convinced I won't be able to persuade anyone to work with me. I'm convinced I won't be able to come up with a worthwhile idea. I'm convinced that even if I was wrong on the last two counts, I'll still come up short on execution. 

There are currently 3 things keeping me going: The knowledge that it logically makes sense to do it, the urging of my friends who have made similar moves, and the knowledge that failure, along with this self-doubt is as common as table salt.

From my viewpoint right now, I can't imagine that the money I'm leaving on the table would be more fulfilling for me than the lessons and stories that will ensue. I know in my heart that when I look back at this decision, I will be glad I did it, glad that I took this leap of faith into a dark abyss. And yet...

Is this what entrepreneurs refer to when they talk about the pit of despair? It certainly feels like it.

That feeling of despair hung over me for months. I share this not for pity or exhibitionism, but for two reasons: The first is purely documentarian and selfish; This is, after all, my own reflection on my year. The second is to share my personal experience with anyone who may be going through a similar experience. Knowledge that a struggle – privileged as it may be – is a shared experience, has always helped me push through. In hindsight, I can look back at that fear, and though it’s still there, I can say that it was the right decision to make.

Through this experience and others this year, I’ve resigned myself to a life of perpetual imposter syndrome. To this day, I feel the pang of anxiety as a technical conversation gets underway. Will this be the conversation that outs me as incompetent? No matter what I learn, what I accomplish, or how much I grow, it’s there, forcing me to question, re-evaluate, and challenge myself. In any endeavor, trivial as it may be, the better I become, the higher my standards, the lower my ability to meet them.

Those first few months of the year weighed so heavily on me, I stopped cycling, I stopped dieting, and I became afraid of downtime. I filled my weekends with skiing, bike rides, scuba lessons, motocross lessons, camping, and travel. I cherish those experiences now, but they were distractions. Increasingly, I spent time in Google Maps Engine plotting my road trip. I was off and running.

Part 2: Travel

In late June, I bought a 1991 VW van. A couple of trips to REI later, I had it packed and ready to go. I picked up Ben at 4 AM and we headed south. I didn’t know what to expect going in. I imagined a trip where I would spend a month of solitude in the mountains, but I chickened out, and invited friends. I ended up spending only half the trip on my own, and was glad I had friend with me for the other half. I met some great people on the trip, some of whose stories I shared on this blog already. 

Today, I yearn for the clarity of mind I had on the trip, and the simplicity of life it accompanied. The Southwest was a beautiful place to be in May, and a van turned out to be just what I needed at the time. I was forced to step out into the world in a way I had never done before, and I was forced to interact with people that didn’t come naturally to me. I grew up in Syria, where the class system was more formalized. Interactions with strangers was distant. In America, interaction with strangers is the norm, a part of daily life. It takes active effort for me to put my guard down, and living in a van was a forcing function. Bob, whom I met in Death Valley, stands out to me from my travels. His life offered a pure alternative to mine, and it was refreshing to see someone dedicate themselves so wholly to their love.

I also ended up reading quite a bit on the trip. 10 books in total, and those books helped frame some of my thoughts. Specifically, Man’s Search For Meaning, Zen and the Art of Motorcycle Maintenance, and, yes: Eat Pray Love. These books helped me think back to why I do what I do for a living, and what motivates me to do it. I think I lost sight of that at some point, and it felt good to see it again. The day took on a routine that started with breakfast, reading, cleaning, planning, packing, driving, arriving, reading, cooking, campfire, and sleep. The routine freed up time and space for even more introspection.

I arrived back in San Francisco 4 weeks later with a clear head, a slower heartbeat, and a smile on my face.

Then Ryan quit, and I had an unemployment companion. Luckily, the World Cup had just started, and we no longer had to struggle to fill our time. We both had an upcoming trip to Norway planned, and the downtime in between was spent playing pool, drinking beer, and watching soccer matches. In itself, that experience was a wonderful break from a lifelong obsession with productivity and work. 

3 weeks in however, a thought began to gnaw on me. What if my birthday blog post ended there? How would I feel about it? I decided that the story of the year ending in a bar would be disappointing. Ryan agreed, and in lieu of an actual idea, we decided to make a bet: We’d both commit to releasing an app to the app store by the release of iOS 8, and the one to make more money, wins. Clearly, neither of us released an app. However, the project that sprouted out of that bet is what keeps me busy today.

Back to travel.

We made the bet, and a week later, we picked up an Über to Oakland International Airport. 9 hours later, we landed in Oslo, and I’ll leave the recounting of what happened there to Ryan: Part 1, Part 2, Part 3, Part 4. Norway was the second-best trip of my life, second only to the van trip. The recall of what those hikes felt like sends me nostalgically back to the mountains and the grass and the snow and those ringing sheep.

A couple of weeks in Norway and Ryan headed back stateside, and I made my way to Amsterdam, Paris, then Detroit. Those last three destinations passed in a blur as I frantically worked on my project. It had been so long since I’d been so thoroughly engrossed at work, it was like rediscovering it all over again. The pride, the ownership, the challenge, and the rewards were intoxicating. I made it back to San Francisco with a working prototype. 

Part 3: Back to Work

Stay tuned.

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