Remote workers share their biggest challenges

Marija Kojic

Last updated on: May 11, 2023

It is old news that remote work is on the rise. But, despite the growing popularity, distance working comes with its fair share of challenges.

We’ve asked 19 experts who have experience working remotely in different positions to share their biggest challenges of remote work. 

Here’s what they told us.

Remote workers share their biggest challenges

Table of Contents

Diane Lee, Freelance Writer, Editor, and Author

The main challenge I face as a remote worker is isolation. When I worked in an office back in Australia, my colleagues were also my friends.

Diane Lee is a freelance writer, editor, and author of both fiction and non-fiction books — she’s been working remotely since 2016.

Diane’s challenge #1: Isolation 

Unless Diane makes the effort to socialize, she doesn’t — her part-time job, however, helps bring her together with other people:

“The main challenge I face as a remote worker is isolation. Although, the benefits are that I can more or less work my own hours (pressing deadlines aside) and from any location, the fact that I work alone (as a sociable person) is something that I’ve had to overcome. When I worked in an office back in Australia, my colleagues were also my friends. We would socialize often, particularly for that great institution of workplaces around the world: Friday night drinks.

I’ve found that I now have to build socializing into my daily routine because if I don’t actively seek to socialize, it doesn’t happen. Luckily, many of my friends are also freelancers, so we often meet for a morning coffee, lunch or dinner — or even a workout at the gym. I’ve also taken a part-time teaching role so I can balance up the people side of things with the freelance part of my life. Teaching also helps with cash flow!”

Diane’s advice on how to handle lack of socialization and feeling lonely

Purposely build socialization into your daily routine. 

Befriend other freelancers and go with them to coffee, lunch, dinner, or workouts. 

Get a part-time job that requires you to talk to people.

Sumit Bansal, Founder of an online platform

Initially, I found myself working all the time, as there was no clear distinction between work and home.

Sumit Bansal has been working from home with clients as a consultant on Excel-related projects since 2013.

His biggest challenges are juggling different time zones and establishing a proper work routine.

Sumit’s challenge #1: Different time zones

“Since I work with clients from across the  globe, not being in the same time zone as the client is a major challenge. There are many simple queries that can be answered right away, but since we are in different time zones, it often leads to a waste of time. Sometimes, I am compelled to work in the client’s time zone to make sure things are moving along smoothly.”

Sumit’s advice on how to handle different time zones

Try to work in the client’s time zone.

Sumit’s challenge #2: Lack of a proper routine

“While you can limit your working hours when working from an office, it takes a lot of self-discipline to make sure you’re not working all the time when working from home. Initially, I found myself working all the time as there was no clear distinction between work and home. This had a negative impact on my lifestyle and well-being.”

Sumit’s advice on how to handle a lack of a proper routine

Set up a dedicated workstation and aim to limit the time you spend in that room.

Chris Schalkx, Travel Journalist and Photographer

“While the ‘working while traveling’ thing definitely is a lot of fun, I do feel like I’m missing out on all the sights of a new destination when I’m glued to my laptop screen — which often leaves me questioning myself why I paid to fly all the way to somewhere new.”

Chris Schalkx has been working remotely since 2017, and he is an avid traveling photographer who contributes stories and photography to various brand publications such as National Geographic Traveller, The Guardian, VOGUE, and many others.

Chris’ challenge #1: Lack of personal interaction

The lack of in-person interactions that comes with remote work is one of Chris’ biggest plights:

“I’ve never seen any of my colleagues face-to-face, so everyone is simply a team chat app avatar or blurry webcam picture for me. As I’m one of the few remote workers, I miss out on office banter and inside jokes — something that’s hard to overcome if all communication is done through email or Skype. I have a weekly video catch-up with my manager where we discuss results and planning — this helps me stay on track and keep myself updated about what’s happening in the company.”

Chris’ advice on how to handle a lack of personal interaction 

Don’t miss weekly video catch-ups.

Chris’ challenge #2: Working and traveling 

Apart from working from home in Bangkok, Chris also works ‘on the go’ — he has worked from Mumbai to Taipei and everywhere in between. 

But, traveling while working isn’t what it’s cracked out to be — his work often stops him from enjoying all the new places and sights he’d want:

“While the ‘working while traveling’ thing definitely is a lot of fun, I do feel like I’m missing out on all the sights of a new destination when I’m glued to my laptop screen — which often leaves me questioning myself why I paid to fly all the way to somewhere new. Despite a very relaxed employer and flexible schedule, it’s sometimes difficult to fully enjoy a new destination when there’s a deadline looming in the back of your head.”

However, Chris has one proven travel hack that helps him have time for sightseeing:

“Since I don’t work full time, I made clear arrangements with the company. My team knows which days I’m working, and which days I’m ‘off’ (e.g. I work on Monday, Wednesday, and Friday). The ‘off’ days can be used for sightseeing and other fun stuff when I’m traveling.”

Chris’ advice on how to handle working and traveling 

Make an agreement about your working days and your days off with your company, and use days off for fun travel activities.

James Rice, SEO and Growth Marketing Professional

“If you are the only remote worker in a large in-house team, it can be tricky to integrate yourself into company culture and be visible to management. This can affect long-term prospects if not managed correctly.”

James Rice has been working remotely since 2015.

James’ challenge #1: Work hours not defined

For him, having no set work hours is where the problems begin:

“Although this is one of the best reasons to work remotely, it can be a challenge if you find yourself working too much. When you don’t have the physical cut-off of leaving an office, you can find that you work all the time and don’t take breaks as much as you should. It is always good to add some structure to your day and, if you like working late into the evening, give yourself a few hours in the day to yourself.”

James’ advice on how to handle undefined work hours

If you plan to work late, save some of the hours during the day for yourself.

James’ challenge #2: Loneliness 

James also finds that remote workers miss out on the chance to form friendships with their colleagues, and adds loneliness to his list of challenges:

“Although some people can relish not having to interact with colleagues on a daily basis, it can sometimes be lonely when you are a remote worker. Work colleagues can become lifelong friends and form the basis of a lot of social activities. With modern technology, working remotely doesn’t always have to equal working alone. There are many ways to connect with people both online and face-to-face, and many co-working spaces are now available if you enjoy working alongside others in an office environment.”

James’ advice on how to handle loneliness

Try a co-working space and interact with people online or in person.

Try to get together with your colleagues face-to-face as much as possible and participate in video conferences.

James’ challenge #3: Corporate culture integration

Another pressing issue is not being able to participate and shape company culture — he believes that this can even affect your prospects in said company:

“If you are the only remote worker in a large in-house team, it can be tricky to integrate yourself in company culture and be visible to management. This can affect long-term prospects if not managed correctly. It is important to be included in important team meetings and events, and to feel a part of the team.“

However, James concludes that remote work can bring a number of benefits if managed correctly:

“Working remotely is a great way to work. It allows for a better work/life balance, often aids productivity and brings teams of the best people together from different locations. Working remotely can be a huge success if businesses or individuals address potential challenges early and look for solutions.”

James’ advice on how to handle corporate culture integration

Participate in important team meetings and events to feel a part of the team.

Leslie Truex, Author, and Founder of a website on remote work

“Many managers and workers haven’t had training in how to communicate and coordinate in a virtual world.”

Leslie Truex is the author of several work-at-home books, as well as the owner of the renowned website since 1998.

She’s appeared on or been featured in The Daily Buzz,, Woman’s World Magazine, Redbook, and a host of other media outlets.

She’s been working remotely as a social worker since 2000, starting as a telecommuter and later switching to contract work. 

She also works as a freelance writer, along with taking on her own ventures.

Leslie’s challenge #1: Communication

For Leslie, communication issues are one of the biggest challenges of remote work — issues that she believes mostly stem from inadequate remote management:

“For me, the biggest issue that comes up in remote work is communication. A lack of clarity from my home office often means extra work for me because I either didn’t do what my boss had intended and I have to redo it, or we have to go back and forth by email until I’m clear on what is wanted. While this may seem like I’m dense, the reality is many managers don’t know how to communicate in writing or other virtual options exactly what they mean.”

Leslie’s challenge #2: Coordination

Problematic coordination in remote work is an issue that is well-known to all remote workers around the world, and here is what Leslie has to say about it:

“The other issue is coordination when many people are involved. I’ve been told to deal with something in two different ways, depending on the person I’m talking to. I’ve been instructed to take care of something that managers knew needed to be done for months, but I’m assigned it days before it’s due.

While tools such as online document storage, project management platforms, video conferencing, etc, have made the potential for coordination and communication easier, many managers and workers haven’t had training in how to communicate and coordinate in a virtual world.”

Leslie’s advice on how to handle communication and coordination issues

Make use of video conferences, online storage tools, project management platforms, and similar programs. Provide proper training for both the managers and the workers on the best communication and coordination practices in the virtual world.

Melissa Smith, Virtual Assistant 

“The worst it ever was for me was in Bali, December 2017. The time difference was 13 hours ahead and there were times I couldn’t say what day it was — I was working a Monday schedule on a Tuesday.”

Melissa Smith is a virtual assistant at the PVA — she has been featured in several remote working blogs and is part of the author/mentor group for the Remote-how Academy with an individual remote work certification. 

She’s been working remotely since 2013 — she started her own company in December 2014 and became location independent in 2017.

Melissa’s challenge #1: Poor routines

For Melissa, in general, the biggest obstacle to quality remote work are poor routines:

“It is very easy to create a poor routine as a remote worker. This might include overworking, isolation, allowing too many meetings, and not enough face-to-face interaction. Routines are extremely powerful and can be a great attributing factor to success when working remotely. However, breaking a bad routine is often much harder. It takes far more effort and accountability.

I found that I was creating extreme routines — like always waking up at 5 a.m. or eating at exactly the same time of day works when I’m traveling alone or at my base home.

However, when traveling with friends or other digital nomads, having such extreme routines makes for a disastrous schedule. When I “break” my routine, it’s much harder for me to get back on course.

I overcame these challenges by creating routines of habit for a certain time of day. I run and exercise in the morning, as well as answer all my emails and then I edit my written work. In the afternoon, when I crave interaction, I schedule the majority of my calls and consultations. This is also the time I write since I’m more likely to be more creative.”

Melissa’s advice on how to handle poor routines

Stick to extreme routines while at home or traveling alone, but not while traveling in a group. Pick a time of day when you’ll tackle certain tasks — and stick to it.

Melissa’s challenge #2: Isolation and setting boundaries

Apart from the general problem of poor routines, Melissa adds that isolation and setting boundaries are the most pressing problems she faces when she works from her own home:

“In my very comfortable environment, I don’t have to travel anywhere so it is tempting to work all day and even on weekends. I find myself to be far less active because my surroundings are so familiar.

I’ve found that the best way for me to create boundaries is not to be strict with myself regarding how much to work or not work. Having somewhere to go, someone to meet, or a book you can’t wait to read makes it much easier to stop working. Often, this will solve my issue of isolation as well. Making sure you’re not isolating yourself doesn’t just mean you have to do things with others. I find that sitting in a park reading a book while others walk by, smiling at strangers, or having a casual conversation does wonders for how I feel.”

Melissa’s advice on how to handle isolation and setting boundaries

Go to the park, sit on a park bench and read a book, or start a casual conversation with someone.

Schedule rewards in the future, to prompt yourself to stop working when you should, and save some time for yourself.

Melissa’s challenge #3: Working in different time zones 

Melissa sometimes lives as a working nomad, and attending meetings while in different time zones is one big problem for her — and disregarding your health to have enough time for work AND sightseeing is another:

“There are a lot of benefits to being able to travel. It’s not always problematic to work a later shift or even a graveyard shift. However, going back and forth is very hard on the mind and body and, again, makes it very hard to create routines. Often, workers will forego sleep in favor of a sightseeing or group activity. Eventually, it will catch up with them. While in the short-term it can be done (and done effectively), in the long-term it is not healthy for the worker — and ultimately results in a loss for the company.

This was something I struggled with a lot during my travels to Asia in late 2017. I learned that, while I have a desire to travel to many places I haven’t before, some are better for vacation and others for working. The idea of “having it all” is attractive, but not realistic.

Melissa’s advice on how to handle working in different time zones

Make plans beforehand, in agreement with your client and company, to find the times that work both for you and for them.

Melissa’s challenge #4: Working from home being less exciting that traveling and working

When she compares working from home and working while traveling, Melissa concludes that working from home is more challenging, especially now that she’s experienced travel — but that there are ways around this:

“Traveling creates a different sense of urgency and excitement for me. It also presents more opportunities for me to get out of the house, which forces me to define my working boundaries much more and stick to them.

Creating a new mindset is the best solution — I have to remind myself that my home base is routinely a 1–2 week visit, much like when I travel across the States or to another country. I try to act like a tourist at home now as well. There is always something fun and exciting going on if you look for it. Also, when you want to relax and reflect, I find it much easier to do it from home — so I take time to change my mindset, do nothing and enjoy it.“

Melissa’s advice on how to handle working from home being less exciting than traveling and working

Find fun new places and activities where you live and act like a tourist when not working.

Charlie Heck, CEO of a creative marketing boutique

“While I love my work/life balance and with a little planning can indeed set my own schedule, there is a common misconception that if you perform remote work from home, you can do whatever you want.”

Charlie Heck has been working remotely since 2016 — she’s the CEO of Checkmark Creative, a creative marketing boutique.

Charlie’s challenge #1: People not understanding that working remotely still means working

Charlie’s greatest obstacle are people who don’t understand that working from home doesn’t give you absolute freedom:

“My biggest challenge are friends, family members, and new acquaintances that assume I can just pop off from work whenever.

While I love my work/life balance and with a little planning can indeed set my own schedule, there is a common misconception that if you perform remote work from home, you can do whatever you want. Most of us remote workers either have to track our time or complete client projects before we can bill out for our work.

However, Charlie believes that there are ways to explain to family and friends that she isn’t always available:

“It’s important to remember that it’s okay to say “No” sometimes. It’s not my job to educate all my non-remote friends and family, but it helps to explain what my day/week looks like and illustrate that most times my projects require my full attention. When I pull up my Asana task list or Google Calendar, the look usually changes across their face. So yes, I have a fabulous life, but this is what I have to finish this week. We usually end up compromising and I’ll take the afternoon off.

Other times, I just say let’s do it! This is why I built my life this way, after all, I can bust it all out tomorrow! Just make sure your phone is charged and you check your email during this last-minute adventure.”

Charlie’s advice on how to handle people’s misconceptions about remote working

Show friends and family a list of things you have to finish by the week’s end.

Compromise, take an afternoon off and schedule your remaining work for tomorrow. 

Just remember to keep your phone close to you and check your email from time to time.

Alexandra Tran, Marketing Specialist

“I get distracted by chores that take me 5 minutes to do at home. I end up doing 5 small chores and there goes 25 minutes of my lunchtime!”

Alexandra Tran works as a remote marketing specialist for a logistics company — she’s been working remotely since 2016.

Alexandra‘s challenge #1: Distractions

While at home, distractions sometimes get the best of her:

“I usually get distracted by my dog and the ability to cook while I am working from home. We use a timing tool to keep track of our hours so that I know when lunch is over.”

Just like Melissa, Alexandra also finds remote work from home to be the more challenging option:

“I get distracted by chores that take me 5 minutes to do at home. I end up doing 5 small chores and there goes 25 minutes of my lunchtime! I prefer to travel so that I can hang out in a new cafe or restaurant. I also get to explore the city once work is over.”

Alexandra Tran’s advice on how to handle distractions

Use a timing tool to help keep you on track.

Hannah L. Miller, Senior Editor

“Traveling can be tricky and a bit stressful, especially at airports. You never know if you’ll have reliable Wi-Fi or if someone will reach out to you with a crisis you can’t solve ASAP,  because you don’t have service or Wi-Fi.”

Hannah L. Miller has been working entirely remotely since 2016. 

She works remotely between Ft. Lauderdale and Nashville — and she has experience with both working from home and working while traveling.

She considers both traveling while working and working from home to be challenging in their own unique ways — she adds Wi-Fi issues and communication issues to her list of biggest challenges:

Hannah’s challenge #1: Wi-Fi issues while traveling

“Traveling can be tricky and a bit stressful, especially at airports. You never know if you’ll have reliable Wi-Fi or if someone will reach out to you with a crisis you can’t solve ASAP, because you don’t have service or Wi-Fi. I can’t tell you how many times I’ve gotten onto a plane and received panicky texts and felt constant anxiety as I’m up in the air, awaiting the problem I’ll have to sort out when I’m back on the ground.

Many planes don’t come with free WiFi, and I obviously can’t take calls on an airplane. So, I try to schedule my flights outside of working hours, but often this is undoable — thus everyone has to rely on my schedule when I’m not traveling.”

Hannah’s challenge #2: Communication issues while traveling

For Hannah, it’s quite challenging to keep the communication with her team flowing when she is away on travel:

“A lot of it comes with experience and being upfront with my team about travel days. I’m a big advocate for open communication. I tell my team when I won’t be available or I’ll be in the air, so that they know not to schedule client calls, etc. I’ve learned how to use a personal hotspot on my phone (had no idea how to do this before) for when airport Wi-Fi is glitchy. I know what airports to avoid. I’ve become awesome at traveling light and only taking a carry on with me, so that I have more of my work day left and I’m not spending it at the airport! There’s a lot of little travel hacks I have for getting in and out of the airport.”

Hannah’s advice on how to handle Wi-Fi and communication issues while traveling 

Explain when you’ll be up in the air, and make prior arrangements with your team accordingly.

Schedule flights outside of working hours, when possible.

Use a personal hotspot on your phone when Wi-Fi is glitchy, for emergency communication.

Connor Mollison, Freelance Photographer, Content Writer, and Designer 

“Although I’m naturally an introvert, lack of social interaction has led to poorer mental health and not as much mental energy.”

Connor Mollison is a freelance photographer, content writer, and designer who performs 99% of his work from home since 2014.

Connor’s challenge #1: Social isolation

For him, the lack of a traditional work environment, with structured days and lots of opportunities to socialize, is the key problem:

Two of the biggest challenges for me are lack of structure and lack of social interaction. I’m still relatively new to remote working, having been doing it for the last 2 years, so it has taken some getting used to. Going into the transition, I hadn’t fully prepared myself on what working from home would be like i.e., there’s no social pressure to work and you’re not in a work environment.

Lack of structure killed my productivity. I would wake up later if I hadn’t slept as well, would have a much slower start to the day and take far more daydream breaks than I would in an office environment. On the other side of that, I would sometimes overwork or pick up my laptop to work on a few bits when I really should have been winding down for the night.

Although naturally an introvert, lack of social interaction has led to poorer mental health and not as much mental energy. I hadn’t quite realized how important it was before I worked from home. I now make sure to keep in the loop with people and often work in coffee shops to get the interaction.

Connor’s advice on how to handle social isolation

Work in coffee shops in order to socialize with people.

Hannah Kowalczyk-Harper, Freelance Writer and Social Media Manager 

“Since my family and friends know my schedule and location are flexible, everybody is urging me to visit them. While I sometimes do this, it isn’t feasible to take every trip.”

Hannah Kowalczyk-Harper transitioned into remote work by working part-time at an in-person job and having the rest of her career be freelance. 

She went 100% remote in 2018. 

Hannah works remotely as she travels — sometimes she simply travels to visit a friend in another state, and other times it’s to other countries. 

Hannah’s challenge #1: Working and traveling 

The temptations of trip invites are her biggest trial, though she also finds the time she spends in front of the computer a big issue as well:

“One of the biggest challenges I face as a remote worker is turning down trip invites. Since my family and friends know my schedule and location are flexible, everybody is urging me to visit them. While I sometimes do this, it isn’t feasible to take every trip because the costs of too many flights add up and I’m less productive when I’m visiting friends. It’s better to stay in locations for several weeks or months at a time.”

Hannah’s advice on how to handle working and traveling 

Stay in one location for a longer period of time — for example, for several months or weeks — to save money and improve productivity.

Hannah’s challenge #2: Too much screen time

Hannah is an advocate for physical activity, and she does her best to stay in shape when working from home: 

“Another challenge is that most remote work involves a lot of computer time and my work is no exception. It’s really important for me to remember to stay physical and in good health. This means taking advantage of workspaces that allow for standing and taking frequent breaks to get my blood circulation flowing. If I’m on a client call that doesn’t require taking notes, you can bet I’m walking around during it. When I need a break from my tasks, I try to do less internet idleness and more squats.”

Hannah’s advice on how to handle too much screen time

Exercise during activities that don’t require you to sit down. 

Try standing rather than sitting, whenever you can. Take frequent breaks to help your blood circulation.

Nate Gell, Digital Nomad and Founder of a website

“Some days I wake up early, ready to own the day and start work at 8 a.m. I power through the day filled with motivation and before I know it, I’m still working at 8 p.m… ”

Nate Gell is a digital nomad and founder of the website eSkate Hub. 

He’s been working remotely since 2016.

Nate’s challenge #1: Finding a daily routine that works

For Nate, and other remote workers he has spoken to, it’s most problematic to find a daily routine for when to start work and when to finish:

“Some days I wake up early, ready to own the day and start work at 8 a.m. I power through the day filled with motivation and before I know it, I’m still working at 8 p.m…

Other days I get up late or have some errands to run in the morning. I start work later at 10 a.m. Then by 3 p.m., I’m mentally checked out and need to take the afternoon off to rest.”

When asked about how he overcomes these challenges, Nate says that discipline and workouts are the answer for him:

“I think the challenge of not working all day mostly comes down to discipline. Although I understand that can be difficult for some, myself included.

What I like to do is set myself non-work tasks or activities for the end of the day. The main way I do this is by setting my workout time for 5:30 p.m. A workout is the perfect segway between work mode and relax mode because, after it, all you want to do is chill out. Doing a workout in the evening is great for clearing your mind of all the days ‘busy-ness’ and freeing yourself up for focusing on much needed ‘you time.’ Evening workouts also aid a good night’s sleep which helps you wake up fresh in the morning with the motivation to work hard all day.

For those that prefer to workout in the mornings or not at all, here are some other non-work activities you can schedule in to cut your work day off at the knees: take your dog for a walk, organize to see friends after work, call your family, have a Netflix date night with your significant other, spend time on a hobby, meditate… There’s an endless list of things you could do to help you wind down — it’s about finding what is right for you.

I think the important thing to remember is that, by taking the time out in the evening to relax and mentally recover, you’ll be far more productive the following day.”

Nate’s advice on how to handle poor daily routines

Find a non-work activity that eases you out of a working mindset. 

Exercises are a great physical activity to help do that — evening exercises help you sleep better, so you wake up fresh and motivated tomorrow.  

You can try meditation, calling your family, taking your pet out for a walk, or anything else you find right for you.

Have some evening time to relax and mentally recover for the following day.

Sireesha Narumanchi, Remote Career Blogger

“When I started working from home 8 years ago, the first thing that really hit me was the guilt of not ‘being present’ for my kids, though I was at home.“

Sireesha Narumanchi has been working remotely since 2010 — she has struggled and learned to maximize her productivity when working from home.

Sireesha’s challenge #1: Establishing an effective work/life balance

“I would say my biggest challenge of working from home was to give my best to work and yet be present for my family. For me, the essence of working from home is to manage both. When I started working from home 8 years ago, the first thing that really hit me was the guilt of not ‘being present’ for my kids, though I was at home. This is something every remote worker struggles with initially.”

Another problem that stems from an unclear work/life balance is trying to work harder than you really can:

“I have eventually learned to work in my most effective times and spend time with my family. I strongly believe in the motto ‘Quality is better than quantity’. I only work when I can work. There is no point working when you cannot focus fully on your task — this is another challenge of working from home. My ideal times of working are early mornings or late nights where I get most of my work done.”

Sireesha’s advice on how to handle a problematic work/life balance

“Quality is better than quantity”, so only work when you can work. 

Preferably, during the time of the day when you feel that you’re the most effective.

Sireesha’s challenge #2: Traveling and working

She also enjoys traveling, and often works on her travels — she believes good organization is key to an effective work routine during vacations:

“One golden rule that you need to follow if you want to be a digital nomad is to be super organized. You should be prepared for all the unplanned things that can happen. For example, I always have an extra set of laptop chargers, multipurpose plugs, power banks etc. ready in my bag. These are the first things I pack when we leave for a vacation. My phone always saves my day when everything else fails when I am out of the country. Having the right kind of utility apps can really make a big difference.”

Sireesha’s advice on how to handle traveling and working

Be a super organized digital nomad and carry an extra set of digital equipment wherever you go.

Make use of digital apps and work on your phone.

💡 Clockify pro tip:

Did you know that you can calculate the time of the day when you are most productive? Head to the link below and find out more about calculating your biological prime time:

Earl White, Real Estate Attorney

“I hadn’t anticipated one of the biggest challenges from working from home was being totally stationary. My back hurt and I gained weight — being productive with aches and pains is difficult.”

Earl White started working remotely in March 2017, when his son was born. 

Even though “real estate is local”, he manages marketing, property analysis, networking, and supervising teams from New Jersey. 

He has a partner and some staff in Florida to cover on-site needs.

For Earl, physical problems and team monitoring (which is a big part of his job), are his biggest challenges while working remotely:

Earl’s challenge #1: Physical problems

“I was employed in an office setting before working full-time from home. Although my job didn’t require physical labor, I moved around regularly with commuting to work, attending meetings, or even just walking to a local store. I hadn’t anticipated one of the biggest challenges from working from home was being totally stationary. My back hurt and I gained weight. Being productive with aches and pains is difficult. I resolved the issue by purchasing a standing desk and yoga mat, as well as a chair with lumbar support. I also go for a walk before work and after lunch.”

Earl’s advice on how to handle physical problems 

Try out a standing desk and a yoga mat, and a chair with lumbar support, to help with potential back aches caused by sitting all the time.

Go for a walk before and after lunch, to get some exercise.

Earl’s challenge #2: Team monitoring

“As a founder of my company, I supervise staff daily. Not only do I work remotely, the majority of my team works remotely as well. Our staff was becoming disjointed, unguided, and didn’t understand how their tasks helped the business. There was little opportunity to converse. I began a weekly Google Hangout and signed everyone up for the same project management/task manager program. The first thing I do each morning is review and provide guidance on the questions and yesterday’s work.”

Earl’s advice on how to handle team monitoring

Start or join a Google Hangouts group or a similar one. Sign everyone up, or join a project management and/or task management program.

Make it a habit to review and provide guidance for all your team’s questions every morning.

Jon Hayes, Online Marketing Expert 

Jon Hayes

“When working from home, you can soon find yourself feeling trapped within your house or apartment and relying heavily on the convenience of having everything you need right next to you.”

Jon Hayes has worked as a marketer for Authority Hacker since 2017. 

His job is to oversee a wide selection of marketing initiatives mostly focusing on increasing productivity and efficiency, as well as to produce high-quality content.

While working remotely certainly comes with its pros and cons, he likes to think he’s been able to adapt pretty well to such a lifestyle. Yet, having everything at hand’s reach in the comfort of his home takes its toll on how active he is during the day:

Jon’s challenge #1: Creating an active routine

“For me, the main concern has been creating an active routine. When you consider that traditional office jobs force you to leave the house to commute to work on a daily basis and often encourage you to leave your desk to grab a coffee of get some lunch at regular intervals, when working from home you can soon find yourself feeling trapped within your house or apartment and relying heavily on the convenience of having everything you need right next to you.

While it may seem counterproductive at first, little things like deliberately not stocking the fridge and forcing myself outside to get lunch are a great way to improve quality of life and get active throughout the day. It encourages me to get out of the apartment for a while and get some fresh air which is great for productivity!

While you can’t deny the convenience of having everything you need right there in front of you, it’s important to remember that a little variety goes a long way in the long term success of remote work.”

Jon’s advice on how to handle poor routines

In order to encourage yourself to go outside, don’t stock your fridge: it’ll force you to go outside for lunch and get active. 

Add some variety to your daily routine.

Michael Alexis, CEO of an online team-building company

Michael Alexis, CEO of an online team building company

“With remote work, you need to be much more intentional about getting social time with coworkers.”

Michael Alexis is the CEO of with 10 + years of experience in the remote industry.

He is obsessed with page-speed optimization and ultra-light living. 

As the CEO of a company that deals with organizing unique team-building events and activities, it’s clear to say that he is an advocate of bringing people together.

Michael’s challenge #1: Lack of social interaction

Michael is another witness that lack of social interaction is one of the largest reported concerns with regard to working remotely:

“One of the most common challenges with remote work is a lack of social connection with your colleagues. When you work in an office, the social element is built in, and it can be as simple as saying hello in the morning, eating lunch together or a quick conversation around the water cooler. These connections support employee engagement, job satisfaction, lower staff turnover, and more.”

Michael suggests simple team-building activities that are easily implemented but can boost your relations with others and save you from complete isolation at work: 

“With remote work, you need to be much more intentional about getting social time with coworkers. For example, if your manager or HR Department plans a virtual happy hour or virtual team building activity, then try to attend it. You can also do little things throughout the workday to help. For example, doing a quick round of icebreaker questions during a Zoom meeting is a great way to get to know people a little better.”

Michael’s advice on how to handle a lack of social interaction

Try not to avoid team-building activities and take the initiative to start a conversation with your colleagues any time you have a chance (don’t underestimate the power of simple small talk).

Kirill Sajaev, Executive Director and Founder of a digital marketing agency

Kirill Sajaev, Executive Director and Founder of a digital marketing agency

“Employees working from home must have a similar experience to those working in the office.”

Kirill Sajaev is an executive director and the founder of since 2018. is a digital marketing agency in Santa Barbara, CA.

He states that his biggest obstacles in distance working include working across time zones, employee inclusiveness, and lack of common courtesy.

Kirill’s challenge #1: Working across time zones

As a CEO, he respects his employees’ needs and emphasizes the importance of establishing a common working time zone that suits everybody:

“While it’s difficult to schedule synchronous activities and meetings in global teams, this does not exempt us from being aware of our employees’ needs. Without a well-defined meeting calendar, the team is at risk of falling behind and having to reschedule brainstorming sessions and catching up. Even something as simple as agreeing on a shared working time zone can go a long way toward making sure everyone is present and aware of the fact that their presence is crucial to the success of many.”

Kirill’s advice on how to handle working across time zones

Agree on a shared working time zone and develop a team calendar.

Kirill’s challenge #2: Lack of common courtesy 

Distance workers sometimes forget that even though they might be scattered across the globe, that shouldn’t prevent them from being polite and respectful to each other. 

Kirill looks at this from the perspective of a CEO and tends to make each member of his staff equally important and worthy:

“People tend to overlook common courtesy when working from home. Instead of making a direct request, sending a warm greeting to your remote staff can do wonders for their spirits. A warm welcome can go a long way toward making remote workers feel more human and less like faceless worker drones. Remember to compliment them for their hard work as well. Always remember that small acknowledgements can have a significant impact. Professional relationships are strengthened when these small acts are brought together.”

Kirill’s advice on how to handle a lack of common courtesy

Treat members of your staff with respect and show kindness and appreciation.

Kirill’s challenge #3: Employee inclusiveness 

Last but not least — nourish distance work communication:

“Remote working cultures have trouble developing inclusive employee experiences. On a computer screen, remote employees feel more isolated. Businesses must use communication approaches that encourage inclusiveness and employee equality when considering a transition to more remote working practices because employee engagement is determined by a sense of belonging. Employees working from home must have a similar experience to those working in the office.”

Kirill’s advice on how to handle the feeling of being left out

Using communication tools and apps is a must to engage your staff and bring them closer together. 

Kyle Risley, CEO of a remote company

Kyle Risley, CEO of a remote company

“One of the biggest challenges is finding ways to prioritize communication with team members working asynchronously.”

Kyle Risley is a health expert and the CEO of a remote company Lift Vault since 2016. Lift Vault is an online service dedicated to offering customers workout plans.

Kyle’s challenge #1: Asynchronous communication

He states that with the mass adoption of remote work comes many challenges. One of such is asynchronous communication

“One of the biggest challenges is finding ways to prioritize communication with team members working asynchronously. If employees are used to communicating with team members who are in the same office, or the same time zone, asynchronous communication (or communication between team members who aren’t working at the same time) is a major struggle. Asynchronous communication often means there’s some down time between when a request or message is sent and when the recipient can respond. This can cause some people to feel like they’re sending letters and can’t rely on getting a swift response when they need it.”

But, he relies on tools and platforms that make distance communication much easier and also puts extra emphasis on the importance of ‘communication culture’:

“However, once you know what tools your business needs to thrive with asynchronous communication, you’ll likely find your business is working better than it ever had before. To start, remote teams should prioritize a culture of communication. Be proactive when providing updates on projects, when team members encounter delays, and next steps on a given project. Proactivity will allow other team members to build strategies for how they can build their day. This can be assisted with industry-standard communication platforms. You can make this more effective by also using project management software that requires team members to routinely update their project status.”

Kyle’s advice on how to embrace asynchronous communication for remote work

Use a reliable communication tool or platform. 

Use effective project management software.

Build a culture of communication.

Brian Nagele, CEO of a digital marketing agency

Brian Nagele, CEO of a digital marketing agency

“Working from home means having to divide your attention between personal matters and business in the most unexpected moments.”

Brian Nagele is the CEO of Restaurant Clicks — a remote digital marketing agency in the hospitality industry. His team started working fully remotely since the start of the pandemic, and he states that they’ve “grown to love the transition.”

Brian’s challenge #1: Battling to stay focused and maintain regular working hours

Remote work provides much less accountability to stay committed to a fixed schedule. Working from home means having to divide your attention between personal matters and business in the most unexpected moments. It can be challenging, at times, to remain focused and enter into a flow state to streamline tasks from a remote office. On other occasions, the impulse to complete all personal tasks before anything else results in spending late nights up at work and throwing off your circadian rhythm.” 

He has an insightful proposition on how to complete tasks during working hours and also bring the team together:

Organize virtual work desks where team members can huddle together to complete tasks. This technique adds a bit of stability and organization back to the remote workspace. Although its intention isn’t to provide surveillance, virtual co-working hours can provide team members with the accountability needed to stay on top of tasks. In the long run, it also contributes to maintaining a healthy work-life balance by establishing boundaries within your schedule at home.”

Brian’s advice on how to maintain regular working hours and stay on top of your workload

Schedule teamwork sessions — Perfect for completing tasks on time and bonding with your team.

A summary of most common remote work challenges (+ tips)

To summarize, remote work offers a number of different challenges to different people: 

  • Being isolated from the team, 
  • Social isolation in general, 
  • Lack of routine and structure, 
  • Issues with family, partners, and friends, as well as health issues caused by sitting all the time, 
  • Not having the time to enjoy new places on travels, and 
  • Other miscellaneous travel issues seem to be prevalent in the lives of remote workers.

But, the creative minds of our interviewees offer great insights into how you can deal with the most common remote-work pitfalls.

Remote work challenge: Social isolation

Ranked as the number one challenge when working remotely — social isolation may be more detrimental to your health than you think. Missing all office jokes and banter with colleagues, work activities and happenings, as well as Friday night drinks makes one feel isolated — and, eventually, the lack of social interaction may lead to poorer mental health and energy.

Also, considering you’re usually just a team chat app avatar to them, making friends with colleagues can be difficult — and since you spend a lot of time working, you’ll have less time (and fewer ways) to meet friends and socialize in another way.

Tips to beat social isolation in remote work

If you make the extra effort through an online communication channel, join a co-working space, or find a group of other remote workers and freelancers you can go to lunch breaks and coffee with, you’ll get the socialization you need.

Another great option, if you feel you don’t have time for proper socialization, is going out to a coffee shop to work, or opting to read a book on a park bench. Sometimes, starting a casual conversation with a stranger, or simply being around other people is sufficient to help you feel better.

Remote work challenge: Working across different time zones

Also one of the most frequent challenges distance workers face on a daily basis — how to work across time zones as a remote team?

Staying on the same page when working with people from around the world — not to mention the difficulty in communication and diversity — may be quite challenging to balance out.

In remote work, team members communicate asynchronously most of the time, and that creates huge gaps and delays in work.

Tips to create a successful global team

What teams should do is agree on preferred work hours and define meeting calendars that everyone should stick to. This way, the whole team remains available, resolves issues as quickly as possible, and improves overall performance.

Moreover, there is another solution to this problem — as an independent freelancer, you can always choose to work in your client’s zone to avoid time wastage while communicating.

Another effective way to stay in touch with your worldwide team is to split your work day into different blocks — place your tasks into time segments that are dedicated to each block and stick to them. This time management method can help you organize every part of your day wisely — both work and private life.

💡 Clockify pro tip:

The time blocking technique will focus you on what’s important, and you will put an end to working long hours:

Remote work challenge: Distractions at home

When you work from the comfort of your home, it’s quite easy to get distracted. Sure, remote work is convenient because you are able to spend more time with kids or catch up on your favorite TV show — but if you don’t set boundaries, it can take its toll on your work.

Tips to deal with distractions at home

Just because you work from home doesn’t mean you don’t need to develop working habits. It’s even more important than working in the office since there you are ‘forced’ to work and focus. Perhaps the most important thing is to have a separate room where you can set up your workstation. Find an unused spot in your home where you will isolate yourself but also feel comfortable working. It would be perfect if you have the opportunity to set your workstation near a window. This way you can get more daylight exposure which is proven to have a positive impact on your productivity, as well.  

Remote work challenge: Building and maintaining strong company culture 

Apart from reducing your chances of befriending colleagues, remote work can cause difficulties in how you all operate as a team.

Asynchronous communication is the most common type of communication in distance work. This means you have to cooperate via email or any other online means of remote collaboration, and probably send multiple reminders and requests — this can lead to a lack of clarity, misunderstandings, delayed responses, and general disorganization.

Coordination also becomes difficult — when told to approach a matter in two different ways, by two different people, what are you to do, if you’re not personally there to voice your concerns?

In general, there seem to be too many meetings and not enough face-to-face interaction that would clarify a lot of issues.

Tips to build and maintain a sustainable work culture

This is where various tools and apps come in handy — storage and project management tools, as well as video conferences, are the way to start. Making an effort to train the workers and management on the best coordination and communication practices in the virtual world is the next step.

Not being able to participate in company culture may lead to you being overlooked by management, which can hurt your job prospects in the long run. To make yourself known and visible to management, participate regularly in the company’s online communication channels.

A whole new level of team issues when working remotely is team monitoring — how do you monitor if you’re not physically present on site? Well, one effective solution is to provide guidance and reviews to your team on a regular basis.

Remote work challenge: Lack of routine and time-management

When you live where you work, and work where you live, setting work/life balance and boundaries is troublesome — some have issues staying accountable and responsible with their work, others find they work all the time.

What’s more, time management becomes an issue — you have the freedom to decide when you want to work, but this freedom makes it harder to find a routine that works. 

Tips to create routines and stick to them

One great solution is to choose and practice an activity that will signal your body that work time is over — exercising is one great tactic, though you can choose any activity that helps you unwind, and stirs your mind away from work.

Another great solution is to use a timing tool to keep you on track — and remind you when it’s time to end one activity and move on to the next.

💡 Clockify pro tip:

Track time spent on tasks and improve your focus with the Pomodoro Timer:

Remote work challenge: Poor work/life balance 

Being at home, but not being present for one’s family is a problem for anyone living with a family. People opt to work remotely so they could tweak their schedules and spend more time with loved ones — but this doesn’t mean they can accomplish this all the time.

Family, friends, and partners sometimes ask for your company even when you’re working — and how do you explain that you’re not free to get off work whenever, just because your office is at your home?

Failing to establish a good work/life balance may even lead to burnout.

Tips to set clear boundaries between work and personal life

Here, objective proof you have to work stands out as your best option — inform your loved ones of your schedule, and when you’ll be free to socialize with them. You can do this by displaying to-do lists or schedules depicting what you have to accomplish by the end of the day, or week, for tangible proof you do have to work.

Alternatively, compromise — re-arrange your schedule, take the afternoon off, and take part in whatever activity your loved ones proposed.

In general, the solution is to work only when you can work, and dedicate the rest of your time to your family — opt for quality, rather than quantity, and work only at the times when you feel effective.

Remote work challenge: Working and traveling but having no time to enjoy new places

People work and travel to be able to enjoy more new places — but the reality of digital nomadism often requires you to work a lot while staying in this new destination, so much so that you miss out on many great sights. Also, it’s harder to enjoy your trip if you have a deadline looming over you.

Tips for saving time to enjoy the travels while working and traveling

Scheduling your travels so that you parse the time you spend there on work days and days off, is likely to help you balance out your workload and appetite for sightseeing. Another great option is to prolong your stay — several weeks or months staying in one place is bound to leave you with enough time to visit everything you want, and finish your assignments.

Time-zone logistics, such as having a double-digit time difference compared to your company and clients, usually calls for many meetings, delayed responses, and wasted time. Also, in general, mixing travel and work may put a strain on your mind and body — to such an extent that you’re unsure what day it is.

The best solution is to compromise with the client and company and reschedule meetings for a time that fits everyone. As an alternative, you can opt to work in the client’s time zone.

Remote work challenge: Traveling too much at the expense of productivity

Considering that fun is only half of the work-while-traveling equation, and that you must spend a part of your travels working — you’ll have to find the strengths to turn down trip invites from friends. If you’re constantly visiting friends and traveling around with them, you’re less productive — though the temptation is understandable.

Tips for those who travel too much at the expense of productivity

Bare in mind that not all locations are equally suitable for you to work there — so, once again, it’s best that you parse your travels into:

  • Places where you’ll work and go sightseeing in your free time, and
  • Places you’ll merely go for vacation, and not work at all while there.

Remote work challenge: Health issues

While working at home, you’ll have everything you need nearby, and won’t have to endure a commute — which means you’ll be totally stationary. And this may cause health issues, like backaches and weight gain.

Tips to remain healthy while working from home

To encourage yourself to get out of the house, don’t leave everything within hand’s reach. Leave the fridge half-empty, to prompt you to go out to buy groceries, or for lunch. Walking is also a great form of exercise to help reduce the risk of weight gain.

If a work activity doesn’t require you to sit still in front of your computer (as is the case with client calls), get up, stretch, and move around. Or, alternatively, try a standing desk — yoga mats and a comfortable, ergonomic chair will further improve your potential back issues.

While traveling, forgoing sleep in favor of sightseeing and participating in group activities is tempting — but you shouldn’t do it. If you believe a place will be interesting enough that you’ll want to fully enjoy it, don’t let sleep suffer — this is another reason to opt to visit some places during vacation time when you won’t have to work at all.

Conclusion: Overcome the challenges and enjoy the perks of remote work 

Whatever challenge you might be facing as a remote worker, remember that — as opposed to office workers — you have the freedom to create your own routines and habits that work for you. True, it takes time and effort to win the battle with yourself, but when you do, you break new ground in finding a work routine that you will never be able to have in the office environment.

✉️ What type of challenges do you face in remote work? Do you have any valuable tips to share with us? Write to us at and we will consider featuring your opinion in this or one of our future blog posts. Also, if you liked this article, share it with someone else you know will find it useful.

Author: MarijaKojic

Marija Kojic is a productivity writer who's always researching about various productivity techniques and time management tips in order to find the best ones to write about. She can often be found testing and writing about apps meant to enhance the workflow of freelancers, remote workers, and regular employees. Appeared in G2 Crowd Learning Hub, The Good Men Project, and Pick the Brain, among other places.

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