In my experience, working remotely has more benefits than challenges. I worked remotely for, gosh, about 14 years all told. I learned a few things along the way. For example:

Challenge No. 1: You’re Always Working When You Work Remotely
This is probably the number one complaint I heard about remote work during the pandemic. Since I had worked remotely long before the pandemic, I didn’t experience this challenge. That was because I had learned a few things along the way.
The first time I worked remotely, I stuck to a very rigid schedule. I clocked in at exactly the same time I would have in the office. I worked straight through without a break until ‘lunch’ time. Then I worked straight through until quitting time. Then I put away my computer and didn’t look at it again until the next day.
Seems like a good plan to avoid the challenges of remote work – you’re not always working if you clock in and out on a normal schedule – right?
Wrong. It was too rigid. There I was slaving away at my computer (or on conference calls) without a break, by myself, just me and an eyeball-searing screen. Too much alone time with a computer can be exhausting. And it was.
I never saw the sun. I didn’t have lunch companions to de-stress with, and I probably ruined my shoulders by hunching over all day.
So the next time I worked remotely, I resolved, successfully, to break things up a bit. I was still at my computer, and still on conference calls. But I took walks during the day. I had an extra cup of coffee in the morning. I did errands during the day if the inspiration struck and worked in the evening to catch up.
My life was altogether more relaxed and I liked it better than my original rigidity. Neither method damaged my productivity. I was promoted while using the rigid schedule and I was promoted while using the more relaxed schedule.
The challenge? I was maybe too relaxed during the sunlight hours and ended up working late at night or on the weekends to get stuff done. Since I didn’t plan in advance when I would be working, I ended up working at odd hours and that crowded out precious time that should have been spent with family. I regret that.
So… the third time around I kind of split the difference. I clocked in at a normal time. But then I took a couple of breaks during the day. I took a lunch break or didn’t depending on the day. If I had more to do once I hit normal leaving-the-office hour, I did it. So I worked late a bit. But once I met my goals for the day (and they were reasonable goals), I logged off. Completely. Once I was done for the day I was done. Period. Finito. No checking email or Slack or anything else. Done.
If I worked through lunch or otherwise had a very productive day, I might log off early and do my grocery shopping or whatever. But yet again, once I was logged off, I was logged off. Completely.
The third time was the charm. I loved working remotely – not too rigid, not too loose, and not always on or having to catch up during what should be non-working hours. And yeah – I did get a promotion the third time too. Remote working worked for me! And it was pleasant to boot.
So here’s my number one bit of advice for working remotely (if you can follow it and please do try): When you log off work, log all the way off.
Logging off is important because – if you can overcome the challenge of being tempted to check your email, Slack or anything else related to your work during your non-work hours – you will most likely love remote work and reap all its benefits.
By the way, this business of not completely disconnecting when you should not be working – it really doesn’t have anything to do with remote work. It has to do with technology. Because people can check in after during non-work hours, and because they are nervous and hyped up and stressed by modern work culture, they do. Back to office folks are not any less tied to their work during non-work hours than those of us who embrace the remote thing.
Challenge No. 2: Zoom Fatigue
Zoom fatigue is real. I experienced it. Researchers have confirmed it.
But let’s face it – meetings of any kind are fatiguing. In person meetings are just as tiring and you can’t even escape them by turning your screen off. Conference calls are exhausting too. Getting Slacked all day and getting a gazillion emails is downright wearying. Office gossip and watercooler chat and getting interrupted 18 million times a day by notifications, in-person drop-bys, other people’s noises and everything else that goes with working is stressful. Not to mention the exhaustion of commuting to wherever it is that your office is located. The very definition of fatigue is having a job.
And Zoom has benefits. It keeps you in touch with other person on a face-to-face basis without the travel time involved in getting to an office. You can still chat with people, socialize, get to them, vent, share random jokes, and everything else while working remotely. I know this because I did it.
The key, of course, is that old bugbear – managing your time. In essence, it isn’t any different from managing your time when you’re in an office. It’s just a bit easier because people can’t physically corral you while you’re returning from the restroom.
This business of not being able to corral you when they get an impulse is why muckety-mucks hate remote work. They are used to, and addicted to, the idea that they can demand that someone kiss their ass, answer their random question, or otherwise be available to them at an instant’s notice whenever they are in the office. In other words, muckety-mucks are of the idea that the ‘slave’ part of ‘wage slaves’ should be taken literally during their working hours.
They want you to do whatever they want the absolute moment they want it, regardless of anything else. Not having to do that is why remote workers are more productive. (Maybe we’d all be more productive if we got rid of muckety-mucks. Maybe muckety-mucks are the first employees that should be replaced by AI.)
Regardless of the addiction of higher-ups to random acts of spontaneous ass-kissing on demand, your job as a remote worker is still to manage your time.

When you work remotely, you potentially have a bit more flexibility in how you manage your time. If you feel like you have issues with time management when you’re not in the office, you can fix in this time-honored but not necessarily fun way:
Become a student of how you’re actually spending your time. Take note of what you’re doing and when and for how long. If what you’re doing doesn’t work, fix one element of your janky time management system. And then another. And then another. And so on.
No one who works has complete control over their time, no matter what management gurus say. Things happen, whether in the office or somewhere else, and other people inevitably have input into what and when you do things. But you can definitely do at least as well at time management working remotely as you can in just about any office.
Challenge No. 3 – You Have to Get Out of the House Sometimes!
This is another big complaint about working remotely. You work from home and it’s not ideal. It’s not ideal because you’re all alone and you crave some outside contact.
Or it’s not ideal because you are not alone, and you are constantly interrupted by partners, pets, and children. Either way, you want to get out of the house for a while!
Ideally, that’s exactly what you’d do. You’d get out of the house. If you have a hybrid arrangement, then by all means, go to the office when you need to. If you don’t have an office to go to, then go to a coffee shop, library, co-working space, park, or any other public place when you can get refreshed and still do some work. Libraries, by the way, are awesome work spaces, if you have one nearby.
If it’s too difficult to actually work somewhere else, then simply take a walk. It’s amazing what taking a walk can do for clearing your mind. Or run an errand. Do something different for a brief spell.
Take a real lunch. Meet up with some friends or co-workers (on a regular basis if need be). Have coffee dates.
I did all of the above, but the most effective for me were coffee dates and walks. It made a difference.
Challenge #4: Suspicious Bosses

Yeah, lots of bosses are suspicious of remote work and remote workers. I’ve seen them blame their own inadequacies on the fact that the worker they were managing the opposite of effectively was working remotely. I’ve seen them ask for insulting documentation that remote workers were doing any work at all.
I don’t know what makes bosses suspicious of remote workers or why they think they wouldn’t be working if they were working remotely, but I suspect it is this: They think they are bad bosses who give out shitty work as part of their shitty jobs and that anyone in their right mind would not do the stupid work they are asking other people to do.
Fair enough. Lots of bosses are pretty shitty and hand out bogus busy work tasks and ask for useless reports or set artificial deadlines because they do not, in fact, have anything useful to do, say, or accomplish.
That’s one of the hazards of working with other people, and it doesn’t go away if you work onsite. If you’ve got a bad boss, you’ve got to manage working for that bad boss wherever you are or the boss is. You’ve also got to actually do the work you’re paid to do if you want to retain any integrity as a human being. Using remote work as an excuse for slacking off damages your self-image in the long run anyway. Slacking off is slacking off no matter where you do it.
But if slacking off is your thing…. you may find that you can actually slack off more to your liking in an office than at a remote location (sometimes this is the case), which means you probably should opt for in-person work so you can slack off just the way you like.
If you don’t slack off, though, and you work remotely, then provide the suspicious boss with the documentation that you’re actually working. Keep in touch with your suspicious or not-so-suspicious boss, and be a decent, accommodating human being about making sure the people you’re working for understand what you’re doing, what you need, and how things are going.
Challenge #5: Being Left Out of Things

Some people find, or at least feel, that when they work remotely, they are left out of the loop or have difficulty getting or staying connected.
This business of being left out of the loop or not being connected happens with in-person work as well. Ironically, you may just not be as aware of what you’re being excluded from when you’re on site.
The freedom, and, for some people the curse, of remote work is that you as a worker have much more control over how connected and in the loop you are. You won’t have the opportunity to bump into people in the hallway or at the coffee machine, but you often have a lot more freedom to reach out to people because you’re remote. Office politics will apply no matter where you work or how big the organization you work for is, so you’ll need to follow your own office politics best practices.
That said, you can reach out by phone, text, Slack, messaging, Teams, email, video conference, and yes in-person meetings if physically possible. If you already have a significant number of connections when you begin remote work, it is a matter of nurturing them and expanding them. If you work somewhere where a lot of people are remote, it is a matter of being friendly and setting up informal networks. If you’re new and an outlier, well then it is a matter of overcoming your shyness to reach out and develop relationships.
For those who don’t like initiating contact, this can make remote work seem disadvantageous or isolating or even scary. So you’ll need to decide whether you want to deal with the effort of maintaining relationships. If you’re an introvert who doesn’t want to have relationships anyway – well, then you might be in luck.
The bottom line on all work, like it or not, is that your circumstances will be built around relationships. If you’re used to going into work at the office early so you can get home to be with your kids, you might never know what kind of conversations and in-the-room type happenings are occurring amongst those who hang out after to work to chat. If you don’t come into work early, you might never know what is going on when those early birds confab before you get there. And so on.
The often unconsciously discriminatory reality is that people in offices are always leaving people out on the basis of their biases and giving more attention to some folks than others. Bros are more comfortable with other bros and they’re chatting with them and networking away behind the scenes. Bosses are giving more attention to people they like, or ignoring people who are actually working in favor of hounding the ones they think are problematic. Leaders are locked in bubbles and only talk to their usual suspects. People develop informal networks by accident and in purpose based on gender, national heritage, religious affinity, ethnic background, income level, status level, job title, love of gossip, sexual orientation, immigrant status, prior relationships, physical proximity, nepotism, shared hobbies, political affinity, shared prejudices, personal affinity, and dozens of other things.
In any normal in-person office environment, you are going to be left out of some of those networks. That can be good. Some of those informal networks can be downright toxic. Your in-the-office political alliances, even if formed accidentally, can make you chronically unhappy, discontented, misinformed, distracted, and even ostracized by other networks.

When you work remotely, you have a chance, if you choose to take it, to create your networks more consciously. It’s not just about who you happen to sit next to.
But….you have to do the work to create those networks. You have to be friendly, follow up, reach out, ask questions, schedule interactions, keep in touch, decide who you want to be close to, and how often.
Which means, the truth is, working remotely can be very good for your career if you’re an ambitious type. You can make it a habit to keep in touch with your manager, and your boss’s boss, and influential people where you work if you make the effort to figure out how to interact with them. You can actually be more accessible working remotely if that’s what you choose to do.
Or…if that’s totally not what you want to do, you can often carve out a remote work backwater where basically no one knows where you are or what you do but only that you seem to do it without drama or fuss.
The choice is yours.
Challenge #6: Interruptions in Your Remote Work Space
This one has been a challenge for remote workers since remote work began. Kids are a challenge. Spouses and partners are a challenge. Pets are a challenge. Deliveries and non-work phone calls are a challenge. And yet another challenge I’ve noticed comes from the gardeners, sirens, construction workers, road work, ice cream trucks or god knows what other urban and suburban noises take place outside your work area. Put it all together and it can be pretty challenging.
Here’s a tip: You get interrupted just as often, if not more, when you work in an office with other people.
I was able to solve the problem of interruptions working from home, mostly because I found myself to be an incredibly focused individual in my own space. It turns out I am not such an incredibly focused individual in someone else’s space. In the office, I found myself distracted by the sound of the shredding machine near my door, loud people, eerily silent people, office gossip, the need to pee, my near neighbors and on and on. In my own space, nothing distracted me.
Obviously, your mileage my vary. You’ll need to know what exactly it is that interrupts or distracts you in the various spaces that you work and whether or not those distractions are beneficial. I was so focused in my home office, I’m not sure I would have noticed if the place caught on fire! Interruptions can serve a purpose.
So, if you’re going to solve the problem of interruptions, you’ll need to gather some data and do some thinking. Keep track of what interrupts you and what purpose the interruption serves (or doesn’t serve). For me, for example, I could not resist office gossip when it was presented to me in person.
One look at the face of someone dropping by and I could tell immediately if something juicy was up. On the other hand, in my remote office, I would get notifications by phone, text, email, Teams, Slack, etc. These methods of communication turned out to not convey high emotion quite as quickly. So I could ignore a phone call, then call back at my convenience, and get the full scoop on the latest dastardly doings or high drama events at my convenience. I didn’t miss out on any gossip, but I was far less distracted by it.
You may be the opposite. At home, you may jump at every single notification on your phone, Slack or email, in a desperate attempt to distract yourself from your boring regular workload, while in an office you may feel like you are there to be productive, so you are.
If you’re going to work remotely at least part of the time, you’ll need to look closely at exactly what interrupts you, whether it’s a welcome and helpful interruption or the opposite, and you’re going to need to decide on how to mitigate the bad interruptions.
This is self-management 101 and it applies no matter where you work. The question will ultimately come down to whether you’re motivated to figure out and apply any necessary fixes (e.g., when the home office door is closed that means no interruptions from kids, partners, or anyone else who lives with you, including pets).
Call to Action
In cases where remote work is feasible, the benefits of remote work outweigh the challenges. Not everyone has to work remotely (or wants to), but as a society, we should encourage and adopt remote work to the extent possible.
Why?
It’s better for the environment. Not commuting has mega-benefits for air pollution, carbon emissions, urban heat islands, and gobs of stuff. Commuting sucks, it’s expensive, it wastes energy and time, creates gridlock and urban wastelands, and is a general buzzkill. JUST SAY NO TO COMMUTING!
It’s the way of the future. Old-fashioned everyone-in-the-office is so 20th century. Cubes, open office plans, high-rise buildings, endless in-person meetings, business travel, etc. – they are all based on a factory model of economic output. Mass production involving masses of people massing in large locations.
Maybe that all seemed cool when Henry Ford was first automating the assembly line, but technology has evolved soooooo much since then. So has the economy, and so has society. Now there is video conferencing for pete’s sake. You can literally have a meeting with people in China via video conference. Not only is a huge amount of work done by phone (which is not in-person), but by various other technologies, such as messaging, email, Slack, etc. It is downright ridiculous to group people together in a single space (at great expense) so that they can interact with people who are nowhere near them by phone, Zoom, etc.
Or to interact with no one, as they pound furiously away on their computer. The reality is – people will literally message people sitting next to them to avoid talking out loud to them, and they will literally put on headphones to avoid hearing or interacting with the people in the office they supposedly came in to see.
It’s ridiculous. It’s old-school, and it’s being held in place by old white guys who think the key to business success is exactly what they learned coming up the ladder – lick the ass of the person above you as frequently and in as buddy-buddy a manner as possible by being at their physical beck and call all the time.
Okay that’s a bit of a harsh generalization, but… the more time you spend with rich white business guys, the more frequently you see that behavior.
And that behavior does not breed competence. It breeds group think (what old fashioned business leaders like to call ‘collaboration’), endless office politics and rivalries, discrimination, and epic fails. It’s an insular way of doing business, and society could be doing so so much better. Which leads me to…
Better outcomes. The world is facing a number of existential crises today, such as climate change, rampant inequality, creeping authoritarianism, simmering wars, invasive technology, and general worldwide discontent with governments and institutions. The current structures aren’t working.
The wide-ranging discontent isn’t new. The 20th century was full of upheavals, such as two (count ’em two) world wars. World wars are not a good sign. Nuclear proliferation is not a good sign.
We desperately need better structures and better paradigms. Sticking to the old-school business way of looking at things might have seemed great post-World War II, but it ain’t any longer. Hell, AI is going to take everything over anyway. We need to broaden our ideas of work and work culture stat.
Way better labor market. Slotting people into jobs based on where they happen to be geographically located is pretty weird, when things don’t have to be that way. Businesses can literally take advantage of talent no matter where in the world it is located if they embrace hiring remote workers.
This not only increases the diversity of perspectives, experiences, and talents available to business, but also opens new opportunities for parents, disabled folks, and others who are pushed out of the labor market to participate meaningfully and contribute to the economy.
It’s a win for workers and it’s a win for business. Society is leaving money on the table by excluding people in rural areas, mothers with young children, people with mobility disabilities, and so on.
It’s time to break free of old models. Advocate for remote work in your enterprise, if not for yourself, then for others who could benefit from it.
Or… do as so many others are doing, and just stay out of the office regardless of what your company’s policy says. Commercial real estate investors will hate you, and so will the politicians who support (and, ahem, are supported by them), but we don’t care about that, do we? ?
JUST SAY YES TO REMOTE WORK!
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