36 Challenges Of Working Remotely

Remote work challenges

While the conversation about remote work continues, there’s no question that employees (and employers) continue to see its benefits. True, some companies are issuing back-to-office orders, but others are making a permanent shift to remote work.

But remote work is not without its difficulties. Addressing these issues is what will help drive the next flurry of moves to remote-first, so I asked our contributor list to share some of their biggest challenges of working remotely.

All in all, I found the responses fascinating even if I don’t face the challenges myself. This list provides a good cross-section of the worries and problems a person or company may face when going remote.


36 Challenges Of Working Remotely

1. Keeping Track of Everything in Your New Environment

One of the biggest productivity killers for remote workers is just getting things done. That’s because maintaining the motivation to work in your home office (in whatever form it takes) can be tough.

Keep a regular schedule when you’re working from home, because it can be a real challenge to separate your job from your personal life when both occur in the same space. Setting boundaries will help you stay focused on your work and ensure that your personal life doesn’t encroach.

You should also use a planner and calendar to keep track of your work tasks, deadlines, and appointments. One effective time management practice you can try is Timeboxing to supercharge productivity.

– Jason Chow of WebRevenue


2. Information Security Risks

Information security is important for everyone, including people working at home. While you likely already have plenty to manage, it’s vital to do your homework on the kinds of security risks that come with the software you’re currently using (free versions, for example, probably aren’t enough). Take the time to research the best tools that will fit your security requirements.

One way to combat security risks is by using a virtual private network (VPN). VPNs provide added layers of encryption when you are accessing sensitive information online. A password manager can also help combat the risk of using less secure or repetitive credentials for remote access to company data and documents.


3. Lack of Work Structure

When you’re the master of your schedule, it can be easy to get distracted and find yourself with no time left before you need to send an important email or complete a project. To avoid this problem, plan out your schedule in advance, making sure you’ve built in time for both work and leisure. Sticking to a schedule will help you feel more organized and productive!

First, identify your productive hours. When are you most likely to get things done? Are you an early riser, or do you prefer to stay up late at night? There’s no correct answer here — find out when it’s easiest for you to focus and then block off those times in your calendar for uninterrupted work.

Next, identify your non-productive hours. When are you least likely to get things done? Is there a time of day when you find yourself scrolling through social media? Can you move that activity to non-business hours? Or limit yourself to 30 minutes (and schedule it)? The important thing is that activities not related to work break up your day in a way that helps you stay productive.


4. Backaches, Neckaches, And Coworker Headaches

Physical issues

For some, working from home can have physical health consequences if the person’s home is not configured for work. 

As someone who has worked from home for a long time, I’ve found that one of the biggest challenges of remote work is dealing with physical discomforts, such as backaches, neck aches, and all the other aches that come along with sitting in front of a computer for too long.

Emotional issues

Since there are fewer opportunities for remote workers to experience face-to-face interaction and connection, it can be difficult for employees to report harassment or discrimination. This feeling of isolation can create animosity and a hostile work environment. This could cause emotional issues between employees that are harder to notice.


5. Balancing Motivation And Production

One challenge of remote work I face is maintaining motivation and productivity. It can be hard to stay focused and productive while working remotely, as there are fewer external factors to help keep me on track. To combat this, I use tools such as to-do lists, productivity tracking apps, and regular check-ins with colleagues to stay organized and motivated.

– James Anderson of Veritas Buyers


6. Beating The Isolation Blues

Not having face-to-face human contact can lead to feeling lonely, isolated, or disconnected from colleagues and team members. To combat this, I make sure to schedule regular video calls and check-ins with my colleagues and team. Additionally, I initiated a “Friday Chit-Chat” with my team to give us all an opportunity to connect on a more social level.

– Kevin Wang of Inyouths LED Mirrors


7. Building A Remote Culture

It takes a lot more time and effort to build a remote culture. It’s easy to get lost in work and forget about the small chats that build familiarity with your team. You have to make a conscious effort to connect. Having regular 1-1 meetings and promoting banter (memes, jokes, conversation) in our business chat helps keep our team connected.

– James De Roche of Lead Comet

See Also: 49 Programs To Strengthen Remote Work Culture


8. Collaboration And Teamwork

Working remotely can make it challenging to properly coordinate efforts and function as a team, which can result in missed deadlines, decreased productivity, and lower morale. Additionally, it may be difficult for remote workers to establish connections with teammates and work together on projects, which may impact the quality of the work they create.

Promote a culture of open and honest communication by hosting regular virtual team meetings and encouraging team members to share ideas and opinions to address this difficulty. This enhances accountability and collaboration, aligns everyone behind shared objectives, and strengthens the sense of community among remote team members.

– Daniel Thompson of Salt Water Digital


9. Connectivity Issues Can Be An Issue For Digital Nomads

Our biggest challenge is connectivity. As a company in the travel niche, many of us are digital nomads with unreliable internet connections. There are missed meetings or latecomers due to technical issues or poor connectivity. This delays decisions and causes frustrations in meetings, and colleagues may accidentally interrupt each other’s contributions.

That said, remote work is worthwhile given the lifestyles we want to live, and investing in better internet connectivity will hopefully resolve this small issue!

– Tory Jon of Camper FAQs


10. Contributing To Company Culture Across Time Zones

One of the biggest challenges of remote working is establishing an emotional connection with your teammates in another state. You can’t chat with them by the water cooler to catch up on their weekend or lean over a cubicle to ask a quick question. Instead, you must learn to utilize the available tools to make reaching out to you digitally almost as easy as tapping you on the shoulder.

Our team has adapted to regularly using tools like instant messaging, which allows gif and emoji responses to add an extra layer of fun to the day.

– Renee McBride of Acumen Connections


11. Deciding Who Should Be Considered For Advancement

In a physical environment, you can see how people work; being around them makes it easier to see who should be considered for promotions and advancement. When you’re not around your people in the physical space, it’s harder to see output, efficiency, and attitude, which is essential for leaders to make decisions about advancement.

– Craig Goodliffe of Cyberbacker


12. Different Work Styles

Aligning the work styles of the remote workforce is the biggest challenge. This becomes a real challenge as team members have different approaches to how they prefer to work and collaborate. To combat this challenge, we focus on managing the workflow, not the people — this helps us build a workplace culture where everyone has the flexibility to perform, aligning their work styles with the company’s goals.

– Sam Chan of PiPiADS


13. Difficulty In Setting Boundaries

I have found that it can be difficult sometimes to set clear boundaries between your work and personal life. One easy way to combat this is having a set schedule and following it strictly every day. Make a designated workspace. Talk to your family and keep any distractions away while you are at work.

– Uzair Rasheed of Nureply


14. Difficulty Unplugging

When we work remotely, some of our team members have difficulty unplugging after work hours. Because we’re always online, remote work has somehow blurred the line between work and life. I recognize that we have hardworking employees, but we encourage unplugging and setting hours for work and home. However, being online all the time seems to be the default for most of us, so this is a work in progress for us to avoid burnout.

– Mark Damsgaard of Global Residence Index


15. Ensuring Your Company’s Core Values Remain Intact

One of our biggest challenges is preserving a unified company culture and values, especially with our distributed workforce. However, it is crucial to ensure that our mission, values, and expectations are consistently upheld. To achieve this, we frequently host virtual events and provide training opportunities to keep our team connected and aligned.

– Krishna Chaitanya Sri of Dilate Digital


16. Family, Pets, Or Doorbell Interruptions

Working from home lets you avoid office disruptions. The bad news is that UPS delivery personnel and in-laws will undoubtedly disturb you. Young children who don’t understand that they can see you but can’t play can make it harder.

– Tom Miller of FitnessVolt

See Also: Working From Home With Kids: Products, Tools & Advice


17. Getting Bored With A Routine

Completing the same tasks day after day becomes a struggle, and I often feel discouraged and unmotivated. I combat it by setting daily and weekly goals to complete, time blocking my day to stay on track, and having a hard stop time, so I know when my work day is over. I also practice self-care before and after work by meditating and exercising to release stress and anxiety. This helps with giving my work meaning and purpose.

– Samantha Kaiser of The Lifestyle Travelers


18. Fostering A Sense Of Belonging In A Distributed Team

One of the biggest challenges we face is making sure everyone feels connected and part of the same team, even though we’re in different time zones and cultures. Good communication is the key, and we use a bunch of tools like video calls, chat apps, and project management software to keep everyone on the same page.

– Krishna Chaitanya Sri of Dilate Digital


19. Inadequate Furnishings & Work Equipment Are Huge Remote Work Challenges

Employers frequently consider the software and hardware tools that employees require to perform their jobs. Less discussed are, however, equally important issues like the environment and the workplace. Not all employees will have access to sufficient space or even basic furnishings like desks and chairs. Although it may seem a little absurd to think about, it can make tasks more difficult to complete.

– Steve Pogson of FirstPier

See Also: My Final Home Office Equipment List


20. Inconsistent Team Performance Due To Indirect Supervision

When you have an entire team of remote workers, it takes time to keep track of their performance relative to each other. When you’re in a different physical space, knowing if your team is effectively completing work tasks or struggling is challenging. This can cause misalignment in the quality of work and overall team performance, leading to a negative company culture. This can easily be addressed by the manager by providing the employees with clear goals and expectations.

– Warner Quiroga of Prestige Homebuyers


21. Pacing The Workday

As a remote worker, I try to be more productive by simply pushing myself to work at full tilt for hours on end. Unfortunately, this leads to not only exhaustion and burnout, but also diminished productivity.

I’ve since learned to break up my work sessions into 90-minute blocks with 15-minute breaks in between blocks. By being intentional about how I pace myself during the workday, I can accomplish more in less time and with a lot less stress.

– Shawn Plummer of The Annuity Expert


22. Lack Of Direct Communication

As the owner of a company that operates entirely based on remote work, the lack of direct communication is a common issue that pops up, which isn’t present when everyone is working at an office. We can’t just walk up to someone and ask them how their work is progressing.

Thankfully, we are using communications channels like Brosix, which we use for real-time messaging. And since we’re a relatively small team, it’s easy to stay current with what everyone is doing.

– Nikola Baldikov of InBound Blogging


23. Limited Space

Many homes, mine included, were not designed for remote work. I had to convert my guest room into an office. But now when people visit, I am left with no space for them, and my couch and family room turn into sleeping quarters for them. I need more space to accommodate my work life that has moved into my personal life.

– Carrie Longmire of The Christopher Group


24. Loneliness

It is worse than being alone, and there’s no quick remedy available for loneliness at work. Loneliness can sometimes lead to anxiety, depression, and/or mental health issues. To combat it, I make sure to find time for activities outside of work and strike a balance between the two.

– Doug Mitchell of Argenta Field Solutions


25. Building & Maintaining Strong Relationships With Customers

Coming out of the pandemic, more people grew accustomed to virtual meetings and work. I frequently meet with customers virtually, and I find it more challenging to create strong relationships with them. Trust in my business is extremely important, and that is harder to achieve in a virtual setting.

– DJ Parker


26. Maintaining Focus

A challenge of remote work that I face is maintaining focus. When working remotely, it can be difficult to stay on task while at home because there are many distractions or obligations competing for my attention. I set specific goals each day to ensure that the most important tasks get done first; by doing so, I’m able to maintain focus on the task at hand instead of getting distracted.

– Kacper Rafalski of Netguru


27. Preserving Team Relationships

Working remotely presents a challenge when creating relationships with co-workers. Without water cooler chats and casual conversations around the office, conversations become solely work-related. To avoid a stiff work environment without a positive culture, a company needs to create spaces to encourage team-building. Things like ice-breaker Slack channels, bi-monthly coffee chats, and quarterly happy hours are simple and cost-effective ways to promote better work culture for remote teams.

– Lily Zay of HiHello


28. Maintaining Team Morale

Since we switched to a remote work setup, I have found it challenging to keep team morale high. The lack of face-to-face communication leads to decreased productivity, more miscommunications, and a general feeling of detachment. After noticing such issues, I began implementing weekly team meetings, one-on-one check-ins, and remote team-building activities to help keep everyone motivated. These activities have helped increase productivity and foster a stronger connection among my team members.

– Andrew Pickett of Andrew Pickett Law


29. Organizing And Overseeing Initiatives

I find that the most difficult aspect of remote work is coordinating the efforts of a team that is geographically dispersed. Deadlines and goals must be monitored and achieved by managers regardless of whether their workforce is entirely remote or consists of in-house and remote personnel. In the absence of a physical meeting place, team members may find it harder to convey their ideas and stay on top of their respective responsibilities, particularly when dealing with large, complicated projects.

– Jeff Romero of NovoPath


30. Quality Assurance For Remote Employees

As a manager, it’s often hard to let go and trust your team members, especially if they’re working with clients under your name. Since you can’t directly observe them, you don’t always know if they’re giving the best information or working within your standards.

Building confidence in your team starts with great onboarding and training, so you know they have the skills to portray your company in the best light. Next, implement randomized observations, you can see just how they work with customers, and feel comfortable in knowing they’re representing your company well.

– Erny Peibst of Inside Bodybuilding


31. Employee Learning

Online learning cannot replace the daily learning that is an unspoken part of in-office job roles. We learn a lot by observing and interacting with others — something that is impossible to do when the team is working remotely. Video interactions may be a way of life now, but they got nothing on the kind of education that comes from sharing the same workspace with others.

– Keren Dinkin of Epic Owl


32. Separating Work And Personal Life

The biggest challenge in working remotely is separating home life from work life. It’s easy to fall into the trap of doing “just one more thing,” which often leads to hours of additional work.

I combat this challenge by setting clear boundaries for myself, creating a work schedule and sticking to it, and not working more than eight hours each day. I also make sure to take regular breaks throughout the day.

– Oluchi Taylor of Simply Holistic Wellness Coaching

See Also: Work-Life Balance: Complete Guide


33. Squirrel!

If you’ve seen Pixar’s movie “Up,” you know that “squirrel” is about Dug, the dog, being easily distracted anytime he sees a squirrel. Like Dug, it’s easy to get distracted when working from home. Kids, pets, the TV, and more, can contribute to not getting your work done. Having a designated work area and freeing yourself from any known distractions (if possible) can help you stay focused.

– AJ Silberman-Moffitt of Tandem


34. Technical Difficulties In A High-Tech World

Not everyone is technically savvy, and not every company has an internal tech team that can assist someone having issues with their internet, router, computer, or other technical equipment. It helps to create a plan to rectify computer issues if something breaks or technology doesn’t work properly. Consider a backup computer to use in an emergency. Broken tech can result in a loss of time and possibly your job.

– AJ Silberman-Moffitt of Tandem


35. The Battle Of Bed Vs. Desk

Working from home means that sometimes it’s hard to distinguish between when it’s appropriate and when it’s not to be in bed. This can lead to feeling sluggish, unproductive, and even depressed due to a lack of motivation or engagement with colleagues.

I made a “work zone” in my apartment, which allows me to create a dedicated workspace. I also make my bed every morning so that I associate it with sleep and relaxation instead of work.

– Thomas Simon of Monitask

See Also: How To Set Up A Home Office In A Bedroom


36. Unplugging After Work

My home office is just a few steps away, and I feel that it is easy to just go and get more work done even after the work day is over. I believe there is also a feeling in the back of my mind that I must overcompensate to show that I am getting more work done since I have the advantage of working from home.

How do I deal with this? I set boundaries and ask my husband to keep me accountable. I also set an alarm to remind myself that in order to recharge for the next day, I must unplug.

– Jasmin Diaz of Smoky Mountains


Yes, There Are Challenges When Working Remotely…

Thirty-six issues may seem like a lot of barriers to remote work…but the truth is everything above can be overcome. Investing in the right training, processes, and technology will go a long way in the current problems surrounding connectivity, team relationships, and office setups.

Did we miss one? What challenges of remote work do you want us to talk about? Contact us here and let us know!


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One Comment

  1. I found this article on remote work challenges quite informative. It’s essential to address these issues for a successful remote work setup.

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