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The Good, the Bad and the Ugly of Remote Work (After 5 Years of Experience)


Learning about working from home and location independent lifestyle was a true pivotal moment for me. Before that, I didn’t think much about the concept of “freedom at work” or anything like that.

And even though the concept was a bit far-fetched for me at the time, I realized that it surely was something that I would like to try out.

Since then, it’s been 5 years.

My no.1 conclusion? This thing is not easy, at least not for me. However, it’s also incredibly rewarding, and, in the long run, I think that those rewards make it worth the effort.

So, here are 8 good, bad, and ugly things that I have learned along the way:

1. Create a *normal person’s* work schedule

It took me some time to understand that even though my schedule can be flexible, I can’t really expect to be able to work weird hours constantly, or stay working 24h/day.

So unless you are really sure that you can pull it off, or that you’re wired differently than others and can be more productive during the night, I would recommend sticking to “normal people” schedule. I mean, try to fit your working hours between 7am-7pm your local time.

Most of the people around you work like that, so if you don’t adjust, your social life will suffer. You simply won’t have friends to go out with when you’re finally free, or you won’t be able to take care of things like a doctor’s appointment during the day, and etc.

And most importantly, if your life partner doesn’t share the same schedule, spending time together will be hard. It turns out that 9-5 isn’t that bad of an idea after all.

2. Schedule not only your work

Lately, I’ve understood the value of having a schedule for things other than work also.

I mean, if you schedule only your work then every free time you have, you’ll quickly assign to work as well. That’s why you should schedule your personal time too.

For example, I have 10 (or so) work-related things that I want to accomplish this week, but I also have 10 personal things. To take it further, I might have an important meeting scheduled at 10-11am, but then I have a yoga class at 6-7pm, which is just as important.

Over the years, I’ve learned that I shouldn’t use my to-do list or my calendar for work only. Otherwise, like I said, I tend to use up all my free time just so I can do even more work.

3. Face to face is the new black

Being around people is becoming more and more important to me. Whenever possible, I try to meet with the people I work with. Be it my co-workers, clients or partners, I try doing whatever I can to spend time working together.

And when that’s not possible for whatever reason, I change my environment and go to a busy cafe for a couple of hours and work from there. I don’t mind the noise, and having people around me is always better.

I guess it’s an evolutionary trick that nature plays on us. I mean, for thousands of years, surviving on your own was basically impossible, so we’ve learned to always try having someone else around, and the more people the better. We’re still seeing the rewards of this, even in this modern age where there’s much less threat lurking in the dark. And don’t get me wrong, I’m not complaining. I’m just observing.

4. Insurance / taxes / business / legal stuff

Setting the benefits aside, not working like most people also brings a lot of unique challenges and problems.

Sometimes there’s just no laws in place that would regulate your situation. You can live a few months here, a few months there, but you don’t necessarily reside anywhere. Getting any sort of health insurance/pension can be tough. Not to mention paying taxes or incorporating a business.

More so, you can’t really find professional help either. It’s all still very new … and laws tend to move really slowly. So just be prepared to waste a lot of energy on figuring this all out. It is perhaps the ugliest part of being location independent.

I’m hoping that in a couple of years things will be better, but for now … well … I wish I had some advice for you. Just be aware of the situation.

5. Travel isn’t as easy as it seems

Working remotely allows you to travel more, obviously. You can work from some cool places, and even make every digital nomad’s dream come true – working from the beach (not really possible, sorry, too much sunlight, you won’t see anything on your computer screen).

That being said, after 5 years of living the lifestyle, I am getting a bit tired. I find myself wanting to travel less (changing my daily routine too often affects my productivity). Whenever I can, I try to avoid airplane travel. Airplanes are not good for me as it turns out, and I waste too much time at airports. Plus, the food is crap (at least in the economy class).

So before you envy that one person on Facebook who always posts cool pictures of them working from a weird location, or before buying yet another course on “living your dream by working remotely on an island somewhere,” do some research. Try talking with people who already did it. Learn about their struggles. You know the good, so now get to know the ugly too. Decide if you’re really ready for them, or if maybe your current situation is more in-tune with who you are after all.

6. Living in a different country won’t make you happy

There’s a concept in psychology (?) called the third culture kid. Long story short, living abroad for a longer while can cause a kind of an identity crisis.

What this means in plain English, and it’s not like I mean to be harsh, but in 90% of the cases, you won’t find yourself happier in a new country.

I mean, sure, if your freedoms aren’t respected in your home country, or there’s any other problem that threatens your well-being directly then moving anywhere is going to be an improvement. But if everything is just about alright, then don’t expect a huge boost in happiness.

If you want to explore and experience new cultures then sure, traveling and living in different places is one of the best ways to do so. It will give you a tremendous amount of life experiences, and it’s one of the best things you can do for yourself and for your growth as a human being.

However, it won’t necessarily be easy.

7. Get out of the house!

There are times when you are simply too lazy to get out. You might feel that you have “just too much work to do here right now,” and that you’ll get out tomorrow.

This. Is. Never. Good.

At least, this is not what I have learned from my experience.

Getting out in the morning, even just for a coffee or just to work for a few hours somewhere is always a good way to start your day.

Why? Because it sets you up for something new every morning. It forces you to take a step forward and take action.

8. Invest in yourself

You might or might not be in a place right now where someone else is investing in you. I mean, maybe your company has provided you with the best equipment possible, but maybe they haven’t.

If not, then you have to be the person that invests in your own tools. And while you’re at it, make those tools top of the line. No joke!

  • Get the best possible desk / chair. You’re using it a lot, aren’t you? Also, how about investing in some unusual stuff? Like a standing desk. With something like that, your own body will remind you when you’re spending too much time at work (standing by your desk for 10 hours straight simply isn’t possible).
  • Get the best computer that you can afford. Or rather, “afford” isn’t the word. “Invest in” – that’s the one.
  • Buy yourself the best tools available. Even if you don’t like to spend money in your personal life, this situation is different. Don’t ever compare buying a $200 bottle of wine to a $200 piece of software. Those are two completely different things.
  • Same for conferences or workshops. Do some basic math, let’s say that you make $30/hour. So if a $300 workshop or course can increase your productivity by 5% then it means that in just 1.5 months you are getting your investment back. And in the next 3 years it will get you a profit of something like $8,000. Attending to conferences like WordCamps or PressNomics helped me increase our WordPress themes business and blog 10x last year.

Okay, so that’s my 8 cents. How is your experience with things like this? Are there any specific challenges you’re struggling with while working remotely? Maybe we can figure them out here. Feel free to share.

Leave a comment

  1. I really cannot possibly agree more with your eighth point. I’ve worked for nearly a decade in IT. My time has been divided evenly between a company that made a sound investment into me, a company that made a negligible investment in me, and a company that offered no restrictions on investing in myself but provided the salary, tools, and time to do so.

    I’ll skip the details and go straight to feeling incredible at work, loving being here, and being physically able to spend longer times dedicated to my work at the current job that offers me the salary and the freedom in my own purchasing to acquire higher end peripherals. I feel more comfortable, I enjoy my time at work more, and it can sometimes be a fun competitive aspect to “have the best peripheral” in a group. It also helps to have more interesting water cooler talk. But, the difference between good peripherals and furniture is night and day in the first hour alone.

  2. I’ve been working from home for over 7 years now, and this article hits great points. Thanks for sharing your experiences, Ionut. I find myself in a rut every couple of years, and luckily my team and I are better at handling emotional challenges as we grow together and stay strongly connected. 🙂

  3. Point #8 is hugely important for anybody, working from home or in a cubicle. My 2nd boss explained the Indian rugs he had hanging on his office walls this way: “People drop $1500 on a comfortable couch that they only use for an hour each night to watch TV. I spend 8-10 hours a day here. Do the math.” Make your work environment as nice/comfortable as you can, you’ll enjoy it a lot more.

  4. Been working remotely for 10 years across 2 different companies: one that was not structured for remote workers, and one that was.

    I would add a 9th point and it borders on the ugly: If the company doesn’t have the right tools and structure for communication with a remote workforce, there is a lot of frustration. Either miscommunication or people walking away in the middle of an IM conversation to talk to someone in the office without informing you.

    If you are working remotely, focus on communicating with your colleagues. Use video chat, phones, etc instead of IM when possible, especially if it’s a conversation that can’t be interrupted.

  5. You are right at the base point… but there are always ways to do this better for you and for your clients… Just try to thinking more about all positions.

  6. You hit the nail on the head, working remotely is massively overrated and find a balance between work and your own life can become impossible. Getting out and away from the desk is important to me, keep weekends to yourself and turn the screens off also helps.

  7. Can you be more specific on the business/legal/tax issues that you face? Does it mostly just revolve around not having residency anywhere? Asking as someone in the accounting/tax world wondering what kind of professional help would be good for remote workers…

  8. Very interesting to read your views after working remotely for 5 years. I have just begun my travelpreneur journey and I know it isn’t all rainbows and unicorns, but compared to an office cubicle, it is a helluva lot better! The challenges and struggles are exciting, as I am constantly learning new skills that will not only help me in my business, but also in my personal life. Thanks for sharing!

  9. Consider adding language study into the travel mix. Language schools are everywhere and generally provide inexpensive, safe, comfortable and wifi-enabled environments for longer term stays. Classes only require a short-term commitment for part of the day. This provides a lot of human interaction and reason to get dressed in the morning. You also meet both highly-supportive locals and other travelers and remote workers from all over the world. And, if you focus your travel in locations where a particular language is spoken, you get better at speaking that language, and the world that you comfortably inhabit gets a lot larger.

  10. Hey,
    I am a co-founder and employee of a company so while salary stuff is clear, things like dividends + fiscal residence + tax treaty makes you crazy to be short.
    Just working remotely for a company and being in a specific location all the time is certainly way easier to handle.

  11. You’ve brought a very important thing Derek: remote readiness. I’ve been working remotely for only 3 months now, but the company is remote first. Frankly speaking it has no office at all. This is a great enabler as the only way you can interact with other staff members is actually… remote 🙂
    In my opinion, companies are either remote, or not. I think I’ve never heard of example of a company that is strong enough to do not differentiate remote & collocated staff members.

  12. I do agree with sticking to a schedule. For me, having a morning routine including exercises, doing shopping in a local store works perfectly. Instead of spending this time in a public transport I spend 1 hour on things I need/want to do. Going out before going home, I meant, the office;), helps a lot.

  13. I agree with most of this if you let it seep into your mind. There are two different options; work form home or live on the road. This post kinda straddles that line. If you are not an independent individual then you will find it hard to work alone. Digital pomading is definitely a lifestyle choice and as such isn’t for everyone.

    I love being able to visit almost anywhere at anytime. Such a freedom out do not ever get to experience. Read about my Vespa ride while working across the US

  14. What a great post. Thanks. I am finally living my dream of living and working on a Sailboat. I have to say, the challenges are many and you list some good ones. Connectivity was not so bad in Port, I have High Speed Comcast and that works well. However, I am still trying to find a viable solution at sea, maybe in another 5 years. Ergonomics are another major bummer. whether I am working inside or out in the cockpit, I find that I really have to stay aware of my posture. It is easy to hump over or slouch. Also, #7, So important. I find that if I am not careful, days can pass before I realize I live in the tropics and live like a Hermit. Just going out to lunch and running errands can make a whole lot of difference. Thanks goodness for the Pool and Tiki Bar at the Marina to get some socializing in.

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