2 Years of Working Remotely

Yanay Prop
7 min readOct 5, 2019
In my favorite place 🗻🗻🗻

It’s been two years since I started working remotely, after getting introduced to the idea thanks to the 4HWW. I’ve worked at a startup, and now as self-employed. I’ve enjoyed the nomad’s life, working from Israel, the US, Canada, Switzerland, Germany, France, England, Czech Republic, Italy, and more. I collaborated with people working from 4 different time zones while having my schedule. It’s been a treat to unlock the world, knowing I can work and still earn money while being wherever I’ll choose. What a great time! After doing this for approx. 2 years, I’d like to share some of the reflections, tips, and advice on how to maximize productivity while enjoying remote work.

Some reflections:

  • Remote work can be as challenging as much as office work. If not harder. Finding your productivity peaks, workspace, routines, and habits can be a challenge. Sometimes no one can hold your hand, or answer your question. You have to develop your confidence at work, sometimes going with your guts and hoping for the best. Or in other words, asking for forgiveness, not permission — as I learned from the guys at AngelList.
  • Remote work is a skill, that if you master, can liberate you forever. I found it very aligned with focusing on one’s self. From my personal experiences, I found myself growing as a person, together with improving my work. They are very correlated to each other; if you think about it, your remote work can integrate into your life, as well as the other way around. It’s your decision which one to choose. Some people prioritize their remote work over their life, causing them to lose their energies faster, and destroy their productivity in the long term. I found it helpful to prioritize your life over your work so that you could work better in the long run. Building healthy work habits around your desk and schedule are the ABC for long-term productivity and happiness at work. Invest in yourself and your life, and your work will benefit from it.
  • It doesn’t matter where you’ll be; you’ll always be a lone wolf. Knowing this in advance is very important, and some people will discover it very challenging after they start. Remote life isn’t only about your location, but being surrounded by the people you work. In our case, it merely doesn’t exist outside your 13inch screen. After being hired for the first time at (a YC) startup, it took me about five months to get to the point of meeting my boss in person for the first time! Knowing how to deal with loneliness at work is always a challenge. Especially when your company’s culture is still not formed, or there’s not enough cash in the bank to organize company get-togethers. For me(as an introverted person), it’s easier to deal with it, simply because I don’t feel the need to work in the same room as my colleagues. I even prefer this “loneliness” sometimes. Moreover, I found extroverted people to suffer more from their loneliness at work, missing this physical work collaboration in the office. That makes total sense to me, given the fact most society still hasn’t exited the office. Thankfully to our fast-moving tech space, startups have started creating some cool tools to get remote working teams closer. Maybe that will help us improve.

Some tips:

  1. Have your work schedule planned. Never change your work hours boundaries(for me 9–5). Working remotely can a great cause to postpone work in favor of partying, traveling, being lazy, and whatnot. Since day 1, I’d never worked at nights because of a late start, nor postponed work because of other reasons. If there’s a special event or activity you’d like to do outside of work, plan it to adjust your schedule, or take a day off! 😎
  2. Take a break, get comfy. Since you can spend around 1600 hours a year sitting in a weak position in front of a computer screen, treat yourself! Buy that expensive MacBook, invest $300 in noise-canceling headphones, and all the gear you need to optimize convenience at work. It’s worth it! Having back pain, reduced productivity because of noise, or eye problems aren’t worth the few $$ you save. I was in that movie until I decide to treat myself, and I never regretted it. For personal equipment consulting, feel free to DM me 😉 Also, on the health department, Take breaks every 25 minutes(Pomodoro) to take your eyes off the screen and walk a few steps. If you can, go outside to inhale some fresh air, you’ll return to work feeling way better. I found this to be a 10x productivity habit.
  3. Off work — do something different. When you’re off work, try to spend as little time as possible in front of a screen. Go outside, exercise, explore your surroundings, and enjoy your possibilities as a nomad. These privileges are very easy to forget once you’re in the game, but still very important to appreciate daily. This habit is essential to keep you healthy, both your mind and body. Speaking for myself, I can’t spend the day without spending some time outside in the fresh air, preferably close to the mountains, doing things that make me feel happy. That was one of the reasons I wanted to work remotely so severely, to be able to do my thing.

To tease out a little bit, here’s how my off-work time looked like in the Canadian Rockies 😮

Some ‘Air-time’ in Whistler Mountain Bike Park

Tricks and tools I’m using:

  • Rescue your time — Remote work tends to fall to a more flexible work schedule, sometimes going off the 9–5. I found it to be essential to keep track of the amount of time I spend in front of the computer, and even more important, on which websites. Thanks to RescueTime, I can to keep track of my weekly hour hours, see on which sites I spend most of my time and get a productivity score.
  • Your communication is everything. As one working in marketing, It’s vital to me to keep track of my email’s success rate, see who opens my email and adjust accordingly. Written communication is one of the essential skills, especially when working remotely, so you better be good at it! I found it very hard to get any feedback on my communication skills. Getting to know some stats and response rates can help. My favorite tool for that is Mixmax. Not only a cool name but also fantastic features and top customer support.
  • Have a personal CRM to manage tasks. Many people talk about wanting to have such a tool to keep track of everything and everyone. The good news is that apps like Notion, Airtable, and Trello can do a great job at it when picking the right template.
  • Exercising doesn’t have to take long nor having too much equipment. Its affection on my day is gigantic. My favorite exercise to do almost everywhere and at any time is yoga. My ideal time to do yoga is at mid-day. After starting to work, having a stretch makes me feel stronger and more energized to continue the day. Sometimes I sneak another evening session. My friend Abi is creating fantastic yoga video sessions. Some only take 15 minutes. I’ve been working out with her videos for the past three years, and thanks to her I still have abs 💪 Be careful, it’s addictive! 👉 Yoga15
  • Have two laptop chargers, on you carry in your backpack, and another one for your home station, or a spare. It seems tiny, but let’s face it, it’s annoying to deal with connecting chargers and changing adapters ALL THE TIME.
  • Block blue light, from evening time on, or all the time. I’ve found it to be beneficial to avoid headaches and sleep better at night. There are a few ways to control that on your computer’s operating system. Otherwise, consider getting a blue-light blocking glasses.
  • Sleep is your superpower. Speaking of avoiding blue-light in evening times, there are other things you can do to contribute to your night sleep. I’ve found my sleep quality to be highly correlated with my energy levels and mental clarity throughout the day. That means I should pay a lot of attention to my sleep, and try to improve it as much as possible. For me, and many others, it means adjusting yourself to a “holy 8-hours sleep” every night, saying it doesn’t matter what, I’ll have to sleep for 8-hours a night. I adjust myself to a 9-hours one. Many things can contribute to your sleep, and I highly recommend reading the book ‘Why We Sleep’ to get to know them. It’ll change your life.

I have many more tricks and tools I like, but that’s it for now!

It’s been a great time, and I’m thankful for all the talented people I’ve met along the way. I’m still leveraging my ability to work remotely, and don’t plan on going back to the office. I have a lot of passion for traveling even and seeing myself as decentralized.

I try to remember:

It’s about time, Enjoy and appreciate it,

Read blogs, try to write one,

Meet many people, not only online,

Spend time in your favorite environment,
Consider it being under a tree or by the beach,
If you can, try to work from there,

Your life isn’t your work, and it should never be,
Have standards, don’t work with Assholes,

Opportunities surround you,
Everything is free for grabs,
There’s no speed limit,

Don’t forget to say Thank You 🌎

I’m currently looking to work with exciting startups working remotely and would love to help them grow. If you know someone who knows someone, I’d love to hear from you at yo@yanayprop [dot] com

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