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Ten Things I’ve Learned in a Decade of Remote Work

I qualify myself as an ‘X-ennial’. What is an X-ennial? Here’s my best description… I don’t quite fit into the category of tech savvy late twenty something year old Millennials you see travelling the world earning income from nothing but their smart phones. I also do not fit into the 9–5 job mindset that I see in many of the Gen X’ers who were born slightly before me. The first 15 years or so of my working life, however, I behaved like a career minded soldier who happily got dressed in real pants in the morning and went to work. My first job was in the hospitality industry. Name a job in a restaurant and I have probably held it… busser, food runner, server, bartender, dishwasher, cook, kitchen manager, front of house manager, general manager, and the list goes on. The thing that all of the afore listed positions have in common is that performing their job functions requires you to be in a physical location (in this case a restaurant). I worked like this for well over a decade… and then I stopped.

When I got offered my first remote job (in the telecommunications space), I could barely wrap my head around the concept of ‘working from home’. Afterall, the idea of ‘going to work’ had been ingrained in me for all of my working years. How on earth could one do their job from a computer? In my previous jobs, just being called while at home for a work-related problem was an afront. Now my entire job would be done from home.

At the onset of my remote career I was so rigid in my behavior that it was hardly enjoyable. But like anything, with a bit of practice, I got pretty good at it. Here are the most important things I have learned to be successful as a remote worker.

Set Up a Workspace

Work vs. leisure separation was one of my biggest struggles as a newly remote worker. In the restaurant business, it was quite simple: If I was in the restaurant, I was in work mode. If I was not in the restaurant, I was in leisure mode. The same delineation could not be made once my kitchen table and my smartphone became my workspace.

This constant access to ‘work’ along with my pesky case of ‘first to reply’ syndrome (more on this below) led to near burnout very quickly as I consistently found myself working from the moment I woke up to the moment I went to bed.

Regardless of the size of your living space, set up a dedicated workspace. My first remote workspace was a small desk from an office supply store set up in my bedroom. It wasn’t much, and on early work mornings, it drove my wife nuts to have our sleeping quarters double as an office. But it worked. Now, I’m fortunate enough to have a spare room which we converted to a home office.

If you are sitting at your workspace, then it is worktime. If you get up for a break, or the end of the day hits and you walk away, then leave everything there. The problems will still be there in the morning. If the problem truly needs your attention after hours, they’ll text you.

Time blocking instead of normative work hours

Ditch the 9am-5pm work hours mentality and start Time Blocking. When are you most productive (4 AM? Noon? 1 AM?)? What tasks are non-negotiable in your day, in your week, in your month? What tasks are nice to get to but frankly not going to make or break you if you don’t?

Welcome to the world of owning your day. If you use time blocking effectively, then you can get to everything and still be left with time for you at the end of the day. If you’re interested in how I approach time blocking, then check this article out: Time Blocking.

Get dressed… it matters

“No office, no pants… I’m wearing gym shorts… forever”. This is a line of thinking that most new remote workers fall into and most of their spouses could live without. I’ll never forget when I hit the 6-month mark of not putting on clothes that weren’t gym-wear. It was my wife who brought it to my attention, and quite honestly, I needed to hear what she had to say.

When you work remote, it can be very easy to go ‘full-hermit’ in your home work environment. Everything you need is right in the 4 walls of your home, so why get dressed and leave? This is novel and fun initially until it becomes very deleterious for your mental health. I encourage you to wake up each morning and get dressed as though you had to leave the house. This simple act helps to shift your mindset towards the workday ahead. It also gives you something to look forward to at the end of the day (those gym shorts never looked better than after 8 or 9 hours stuck in jeans).

Do not be the first one to answer an email

When I first started working remotely, my need to be ‘first to reply’ bordered on obsessive. I was terrified that if I was not immediately available to reply that the powers behind the screen would think I wasn’t working at all. Then I learned… I wasn’t as important as I thought, and my leaders were not sitting with a timer checking my email response times. In fact, they really weren’t thinking about what I was up to at all unless they needed something urgently (in which case they’d make it known in the subject line).

Don’t take this the wrong way. Even as a remote worker, you need to be a proactive and contributing member to your organization. However, staring at your screen for 8 straight hours waiting for an email to come in so you can reply within seconds is not the most effective way to achieve this. In fact, sometimes it could be downright detrimental as I wouldn’t take the time to think my responses through. This resulted in me being just one more person trying to prove my worth through volume of output rather than quality of output. As a remote worker, you have the luxury and privilege to think before you reply… take advantage of it and you’d be amazed at how efficiently you can learn to handle problems that arise.

Fake it Until You Make it

The last lesson (Do not be the first one to answer an email) feeds directly into the next lesson.

When you work from home, you have the gift of time. Time to think, time to respond intelligently, and most importantly: time to research and learn! If you get asked a question that you don’t know the answer to, take a moment to research it and quickly educate yourself about the topic. I can honestly say that I learned the inner workings of telecommunications technology and hardware via Wikipedia and Google, all while actively working on projects.

Taking the time to educate myself before responding resulted in me frequently sounding far more knowledgeable that I may actually have been on a topic. I’m not saying to learn the bare minimum to get ahead, you should always continue learning and educating yourself to become the most effective at what you do. However, having the time to research before responding can help you to get that edge you may need to stay relevant in a competitive environment.

Some weeks you’ll put in 60 hours so don’t feel guilty about the weeks you only work 20

When I worked in the restaurant business a standard work week was 50 hours broken down into 5 shifts 10 hours each. The issue was that being ‘at work’ did not mean I ‘was working’. I’d venture a guess that at least 25% of every workday in an office environment is comprised of nonwork-related tasks such as chatting with colleagues, quick breaks, and other distractions.

When you work remote, these distractions seem to disappear. There is no cubicle neighbor grabbing your attention to show you the latest viral meme, or to chat about last night’s game, or to pull you away for just a minute that turns into 20. When you work remote, your time is your own, most distractions are self-created, and if you work efficiently then you will quickly realize that it doesn’t always take 40 hours to do your job functions.

This isn’t to say that there aren’t days or weeks that will be busier than others. And it also needs to be well noted that when your work is at home, you tend to be far more available (dinner-time emails anyone?) than you would be if you shut your computer down and left the office each evening.

It took me some time to come to the realization that in many instances I ended up being MORE available as a remote employee than I had been in my previous jobs. I would find myself feeling guilty if I had some down time in the middle of the day and would try to find erroneous tasks to do just to prove I was working non-stop. Well take my advice, STOP IT. Your employer will have no problem letting you answer emails in the middle of the night or texting you when you’re trying to eat dinner with your kids. Therefore, as a remote employee you need to learn to not feel bad if you take advantage of a quiet day or do something for yourself when things are slow. Refer back to the time blocking section for more advice on this.

Don’t forget that your family still needs the ‘undistracted you’

With remote work comes a level of availability that many in-building workers don’t experience. Your phone becomes your lifeline to work and is always in your pocket (at least in my case). My first couple of years working remote cost a large price to my relationship with my family. I thought that just ‘being home’ all the time counted for more than it actually did. My wife and kids didn’t want ‘nose buried in phone dad’. They wanted ‘phone and computer are upstairs behind a closed door while dad is downstairs fully engaged in the moment, dad’. Guess which version they got more frequently than the other?

Sadly, I see this happen all too often with remote based workers. Their need to constantly be available results in longer hours, more distractions, and less dedicated time to loved ones and hobbies. Referring back to the aforementioned lessons will give you some insight into how to avoid this trap and maintain a delineation between work and playtime as a remote worker.

When on a conference call, if you’re not talking… MUTE YOUR PHONE

This lesson falls in the category of lessons that almost every remote based employee has to learn the hard way. But take it from me the folks who are on the conference call do not want to hear your dog barking in the background at the mailman, or your landscaper’s leaf blower, or your sarcastic comments you are subconsciously making about the person who is speaking on the conference bridge. So, do yourself a favor… quadruple check that mute button and if you aren’t talking MUTE.

Break free from the one job, one income mindset

For years in my early career, I adhered to the one job, one income mindset. If I just work hard, I’ll get that 4% raise every year and I can roll it into my 401k and maybe… just maybe… I’ll be able to retire comfortably when I’m 70. I still have a retirement 401k and I contribute to it monthly. It is absolutely intelligent to think towards the future and plan for retirement. However, if this is the ONLY way you see income, then you might be missing out on a wide variety of opportunities to earn ancillary income and boost up your monthly cash flow.

Remote work presents the perfect opportunity to explore the newly emerging world of side hustles and the gig economy. If you have an extra 30–60 minutes a day, then you can likely find some way to make money online (which basically defines the phrase ‘side-hustle’).

I’ll never forget just 3 years ago when a ‘younger millennial’ friend of mine explained to me that if I got big on Instagram, then I could get companies to give me free stuff and pay me a commission for sales I brought them online (affiliate marketing). This blew my mind. To be quite honest, for those of you who know me, this was the impetus for me starting my Happy Human Healthy Living Instagram account. More on that later, an essay about deciding to become an Instagram Nutrition and Fitness Influencer in my mid-30’s can wait for another day.

Since then I’ve taken the side income game much further. I have partnered with a number of great companies as an affiliate earning commission income, have explored the Airbnb vacation rental gig-economy, real estate, gotten certified as a nutrition coach, small-cap investor, and now Medium writer. Some of these hustles barely make a dime, others provide a good amount of ancillary income. Ultimately, it lends a certain degree of security and reassurance to know that if one source of income falters there are a few others to focus more energy into. It becomes a balancing act of directing your input to the hustle that has the most earning potential in a given season of your life. What counts here is that remote work allows you the freedom to explore multiple income streams.

Keep your email addresses straight for all of your side hustles and main gig

If you do get to the point where you have a few side hustles going in addition to your main job, then this one is important. The last thing you want is your corporate leadership seeing a professional email come across from you with your side hustle’s Instagram logo on it (take it from me, it’s uncomfortable when your leadership asks what’s up with the shirtless workout video link when you meant to be emailing about a 5G multi-carrier cellular site). I have 3 separate email addresses (one for my day job, one for my investment and real estate side hustles, and one for my nutrition business). I am a huge fan of Microsoft Outlook because of how easy they make it to switch between email accounts.


There you have it, 10 lessons I have learned in nearly 10 years working exclusively remotely. I tried to order these lessons in order of pertinence for a novice remote worker to a veteran remote worker. While working as an independent contractor and side hustler in the gig economy is not without stress, it is also incredibly rewarding. With the lessons listed above, I have managed to find a level of autonomy and freedom in my day to day life that I could have only dreamed of when I was working in a restaurant. I hope you are able to implement even one of these tips into your remote workday.

Previously published on medium



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Photo credit: Joey Szolowicz

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