Between Workaholism & Procrastination

February 2015

I was working for a startup based in Jerusalem called Curiyo. Back then I had a nice routine: I wake up around 6 am, go to the gym with my buddy, come back to my room to take a shower, eat a bowl of salad and then leave for work. I get to work around 9 am, leave around 5 to meet friends, hang out, or do whatever activity I was planning for that evening.

In September of the same year, I went on my first trip abroad. I went with my best friend from high school on a 2-week trip to Italy. And as they say, I caught the travel bug. After that trip, all I could think about was planning the next ones and when I could fly again. And since then, I started traveling literally every month.

One day, I found a blog post about digital nomads and remote work. "This is it, this is what I want!", I said to myself, and the race began to figure out how I could make that happen. A couple of months later, I landed my first remote job with Toptal and signed up for a 3-month trip around southeast Asia (SEA). And in September 2016 -a year after my first trip- I was in Thailand working remotely, enjoying the beach, drinking fresh coconut water, and calling myself a digital nomad.

"Work hard, play harder": that is the digital nomad slogan. Each day’s schedule looked different from the day before, depending on what I felt like doing or what the group I’m with is planning. In other words, it’s impossible to have a fixed routine, you have to be flexible and dynamic. Otherwise, you will either have to choose between FOMO or doing a shitty job at your work so you don’t miss whatever fun others are having.

February 2017

After my 3-month trip to SEA, it was time to go back to Jerusalem to see my family and plan the next move. I wasn’t excited to go back, I grew up in Jerusalem and till that point, it’s where I spent all my life. It was so hard and boring after what I’ve experienced, I just came back after spending 3 months in heaven.

Suddenly there were no more beaches, no more parties, or random strangers to hang out with. There was a lot of free time thatI had no idea what to do with. All I was doing every day was leaving my parents’ house, go to the university campus where I spent five years getting my computer engineering degree, and work till it’s so hard to keep my eyes open.

I filled all the free time I had with work. I created an outsource web development company with a friend and worked 14h a day 7 days a week, I became a workaholic. I was hoping that by creating a successful business I will have the means to escape my city and move elsewhere to go back to the heavenly life I had for a short period.

After 3 months of long days and restless nights mishmash, I realized that wasn’t what I wanted. Of course, I still wanted to build my own business, but I didn’t like the path I was taking. And one day I found myself writing this:

I woke up late, as usual, tried to open my exhausted eyelids. I had skipped the usual question “What’s the plan for today?” and left my bed. It has been almost 3 months since the last time I answered that question, after the first week of going back to Jerusalem it was the same day repeating itself over and over again. Wake up, go to the university campus, meet the same people, and work for 12-14 hours.

Everything was the same that day except one thing, one thought. When suddenly I found myself shouting out loud to myself “Oh shit, I’m not happy, FUCK!” after a voice inside my head asked: “Are you happy?”. The answer was obviously no. I just realized I was on auto-pilot and forgot to ask myself such a trivial question. “If you are not happy, what is the point?” I kept asking myself for the rest of the day.

Work was just my way to escape reality and fill my free time. All that made me wonder: do I have to bury myself in work and live miserably now so that my future self can be happy? 

Probably many of you will say “yes”, or maybe you will hesitate a bit before saying “no”. But that doesn’t change the fact that it is actually what we all do somehow. All of us work hard today hoping that tomorrow, next week, next month, or a year from now we will be happy, satisfied, and fulfilled.

This led me to another question that has changed everything: what is the point of chasing big dreams and goals if I'm not enjoying the way to get there? 

I didn’t have a clear answer to this question so, in a way or another, my answer was procrastination. On one side, I wanted to build a business and create great things. On the other side, I didn’t want to work (hard) on anything as long as I don’t know how to be happy while doing it!

June 2017

After several months and hustling paperwork, I moved to Germany, and my digital nomad life was on again. Since then, I’ve spent the last 3+ years, traveling around the world, exploring, having fun, and creating memories. I was living the dream that many people dream of. A was living a life with no routine whatsoever, wake up whenever I want, work whenever I want, and tomorrow is always an unplanned adventure.

You can say everything was perfect, but still, the old dream was bugging me, I want to build and create a successful business, my own business. I never liked the idea of working for someone and trading my time for money. And between fun and procrastination, I was trying to build stuff and bootstrap ideas, but things were always falling between the cracks. With a lifestyle like that, it’s really hard to say no to the sunny beach outside and go work 10 hours on a side project. So as a result, procrastination became my new lifestyle.

March 2020

I left Mexico for a 2-week trip to San Francisco, I had a lot of traveling planned for this year. Things would have stayed on the same path as before for at least another couple of years if it wasn’t for COVID-19.

Two weeks into the pandemic, I found myself without work and without anything else to do. No travel, no friends around, nothing. This time, I didn’t only have a lot of free time, but all my time became free time. History got a chance to repeat itself, and I had a decision to make. Do I want to re-live 2017 all over again? Do I want to keep myself busy with side projects and endless work? 

The feeling from 3 years ago was still fresh in my memory that I didn’t want to fall into that trap again. That was an opportunity I had to take advantage of. I was living alone with no distraction of any kind, It was a chance to rediscover myself and what I really want.

My goal was to bootstrap a business while having a work life balance. I didn’t want to spend 14 hours on my laptop and feel like it was sucking the life out of me. I believed it was possible to bootstrap without falling into the workaholism swamp.

Earlier this year I was somewhere on the bottom left side. To shift toward the right I had to deal with my procrastination problem. Since nothing I’ve tried before worked for me, I decided to learn everything I can about the subject and challenge myself to write a book about it, this book! I’m trying to prove to myself (and others) that it’s possible to live in the middle, a place where you can be productive and happy.

“A bird in the hand is worth t̶w̶o̶ ten in the bush”

My best friend, who is running an online business with ~$300k ARR, is on the opposite side of the curve. He is the most dedicated hard working person I know, but he’s not happy. When I asked him about it, he said he doesn’t believe it’s possible to have that balance. For him, you can’t be productive (grow fast enough) and happy at the same time. His goal is to have a big stable business by age 40 so he can relax and enjoy life then.

I don’t want that, I don't want to build a business if my happiness is the price. I don't want to live on 30% happiness for the promise that my future self will be 100% in five or ten years. It's not only that 100% happiness is not realistic, but I also believe my future self will still be stuck on the same hamster wheel convincing himself that he needs another 5 years to get to the imaginary perfect happiness.

Workaholism will blind you, you no longer see the big picture, you have no time to think and re-think, and you work for the sake of the work itself. And without a proper system and regular stops where you pause to double-check where you are heading, the wheel will just spin faster and faster until it eventually spits you out and throws you against the wall.

I know, sometimes you have something you are so excited about and it doesn’t feel like work. But pure excitement doesn’t last forever. Eventually, you will have to work on other boring and less exciting parts of your project. And once that initial excitement fades away, you either quit or close your eyes and hit the gas pedal to become a workaholic zombie.

However, life is not easy and you can’t always accomplish things while relaxing and taking it easy. Sometimes you have no other option but to push so hard, for days, weeks, or even months. The problem starts when you have no idea when you are going to lift your foot off the gas pedal to look around and see where you are going and check if you should make a turn and change directions.

So let’s glue all pieces together. A Procrastinator has this Instant Gratification Monkey (1) who wants immediate rewards, to have fun, and enjoy the moment without giving a shit about the future. A workaholic has a Panic Monster (2) who wants to work so hard and sacrifice everything today so you can be happy tomorrow.

The answer to the question: “How do you chase big dreams and without depriving yourself happiness?” is the same answer to the question: “Where could your instant gratification monkey meet your panic monster?” You need both.The monkey is as important as the monster, we’ll see that in the chapter “The Productive Procrastinator”. While in other chapters, we try to find that meeting point, as the sole purpose of this book is not to help you just be a productive person but a happy productive person.

1,2: originally presented in Tim Urban's blog post

📕 This chapter is part of my upcoming book “TL;DR — a book about productivity by a procrastination master”. If you enjoyed this one, check out more details about the book.