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12 Biggest Challenges of Working from Home – How to Overcome Them


As millions of workers around the world start telecommuting for the first time due to the COVID-19 pandemic, few know what to expect. They only know the image peddled by all those “Work from home!” ads littering the Internet.

I’ve been telecommuting for over 12 years, first as an employee, then later as a freelancer and a virtual business owner. During that time, I’ve lived on three continents as a digital nomad and expat. And as much as I love my lifestyle, it comes with plenty of hidden challenges those sexy ads fail to mention.

Managers and executives don’t put “tiresome” workplace policies like dress codes and standard working hours in place because they like to vex their workers. Instead, these policies help employees work efficiently and keep companies profitable. And that work-from-home rhetoric creates misconceptions about what telecommuting is really like — misconceptions that contribute to the high rate of business failure among entrepreneurs and poorer performance among many telecommuting employees.

If you’re telecommuting for the first time or thinking about starting, beware of these risks and challenges. The better you recognize them, the easier it is to mitigate them and succeed as a remote worker or small-business owner.

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Challenges of Working From Home and How to Overcome Them

1. Managing Your Own Schedule & Time

Sounds appealing, right? No more setting the alarm for 6am. No more sitting in your cubicle all day, your only escape a measly hour for lunch. You can set your own hours and work when you feel like it. Freedom is yours!

Except it doesn’t work that way.

The concept of “normal business hours” remains in use all across the globe because it works as an efficient time management tool. When you have set hours, you know when you’re supposed to work and when you’re free to pursue other interests or spend time with your family. You can make plans days, weeks, or months in advance because you know when you’re going to be working.

Without that structure, many at-home workers find themselves in big trouble. They sleep in, they procrastinate, and they tell themselves they’ll knock it out later on. Suddenly, they look at the clock and realize their kids come home from school soon — and they didn’t do what they’d intended to do.

That leaves them with a choice: work through the evening or just procrastinate further. Many conventional employees complain about the structure of a regular schedule. But it actually serves them far better than they realize.

How to Avoid Time Management Doom

Set your workdays and hours and stick to them. In most cases, that either means maintaining regular business hours or basing your work hours on the schedule maintained by your spouse or kids. Not only does a conventional schedule make you more productive, but it also allows you to spend time with the people you care about.

For example, I work from around 7:30am to 12:30pm, then break for 90 minutes or so for a workout and lunch. I then return to work from around 2pm to 6pm. On Saturday mornings, I usually work for two or three hours as well.

But if you do decide to stick with the tried-and-true 9-to-5, you still reap significant remote work benefits. You don’t have to commute to work, so you can sleep in later. Moreover, if you need to run any important errands like doctor’s appointments, you don’t have to request permission.

2. Blurred Line Between Personal & Professional Life

On the other side of the coin, when you work from home, you no longer have a clear geographic division between workspace and personal space.

Ideally, your home is a place of relaxation, safety, and security. It’s a place where you subconsciously slip into a calm, easygoing state of mind, putting the stresses of the workday behind you.

Working from home punches a hole right through that neat mental division. Many telecommuters complain they feel like they’re never off the job. They always feel a compulsion to check email or get “just one last thing done.”

In other words, they have a hard time turning off and relaxing. Ever.

How to Avoid Blurred Work-Life Doom

You must set aside a physical space for working, separate from the rest of your home.

For many, that means a home office. My business partner maintains a home office with a door that locks and a huge warning sign never to interrupt her when the door’s closed. It took a while, but her family eventually learned to respect the rules. She doesn’t show up at their work to interrupt them, after all.

I pay for access to a coworking space and find it worth every penny. It creates a clear division between my work and personal lives, helping to maintain work-life balance.

When I do work from home, I set expectations with my wife not to disturb me unless the world is ending. I invested in a pair of outstanding noise-canceling headphones, which block out family noise and keep me firmly entrenched in my work.

If you have a spare bedroom, library, den, formal dining room, or other room in your home that sees infrequent use, consider converting it to a home office, even if only temporarily. If possible, close the doors while you work and hang a “Do Not Disturb” sign.

You can potentially take the home office tax deduction if you opt to create a dedicated home office. However, the rules have tightened in recent years, so make sure you understand them thoroughly before basing your decision solely on the tax deduction.

Ultimately, the clearer the boundaries you draw — both in space and time — between your work life and personal life, the better you can keep the two comfortably distinct.

3. Distractions

Even if you decide on a set schedule and have a dedicated space to work, actually staying productive during your working hours can prove challenging if you’re working from home.

Surrounded by your personal belongings and reminders of chores, it’s hard to focus. Distractions like your TV, books, and the laundry start calling to you. Despite planning to work until 12:30 before breaking for lunch, you find an excuse to break early. If your family members also happen to be home, they don’t hesitate to interrupt you at every opportunity.

It’s one of the many reasons I avoid working from my home — to remove those distractions and keep a firm barrier between my work life and home life.

How to Avoid Distraction Doom

Physically removing yourself into a separate home office helps. But also make sure you remove distractions from your work area. With no TV or books around, you succumb to them less easily.

Noise-canceling headphones can help you avoid auditory distractions, such as your kids playing or your spouse watching your favorite show.

Set rules with your family not to disturb you while you’re remote working. Tell them to behave as though you were at the office.

Then read up on other ways to avoid distraction when working at home because it makes a far more significant challenge than most office workers assume.

4. Reduced Supervision & Direction

People love to gripe about their bosses. But bosses serve a crucial purpose, providing direction and supervision. They not only tell you what you need to do, but they give you feedback about your progress on it.

When you work from home, you tend to get less supervision and direction. Your boss (or clients, as the case may be) typically doesn’t give you as much guidance — guidance many remote employees desperately need to stay on track.

How to Avoid Directionless Doom

If you work for an employer, remain in close communication with your supervisor. Ask them which projects you should prioritize and when they expect you to reach each milestone.

At least once each week, connect with them to discuss your progress, your challenges, and any ideas to address those challenges. Keep them in the loop so they can provide better feedback and direction.

If you work for yourself, start with setting broad weekly goals. Then every morning, set three high-priority tasks. You can cycle in smaller tasks like keeping up with email as you get a free five minutes, but keep your eye on the larger high-impact tasks.

All of these help you answer the most critical of questions: What’s the most important work I can do today?

5. Communication & Coordination Challenges

It’s hard enough to hold productive in-person meetings to coordinate different team members’ efforts to remain aligned. When everyone works from home, it becomes all the harder to stay on the same page.

Human beings rely on nonverbal communication when they speak. But emails, phone calls, and even video calls remove much of the nuance from how we communicate. Just think back to the last time someone misinterpreted an email or text message you sent for a quick example.

This problem is so inherent in virtual businesses that an entire industry has sprung up to solve it. Team collaboration and communication tools like Slack exist specifically to make it easier for companies to stay in touch and stay organized. GoToMeeting is another popular choice for companies to stay in touch using video conferencing.

How to Avoid Communication Doom

If you’re a boss or supervisor, schedule weekly phone or videoconference meetings with your most important teams. Check each team member’s progress toward their previously agreed-upon deliverables and goals. At the end of each session, set new deliverables and objectives for each individual. Ask each responsible team member to repeat these back to make sure they fully understand them.

Team members should similarly confirm their priorities and tasks with their boss or supervisor and colleagues before setting off to complete them. Virtual communication leaves too much room for ambiguity, so verify assignments at the end of any call, conference, or email. The same policy applies to self-employed workers communicating with clients and vendors.

For daily communication, use project management and collaboration tools like Slack or nTask to keep track of all communications and ensure all team members remain in the loop using the same platform. These allow for tracked communication threads between two or more people, assignments, file sharing, private messages, and more, replacing email for more consolidated quick communication with no lost messages, spam, or nonwork distractions.

6. Unclear Performance Metrics

By what standards does your boss — even if that’s you — measure your job performance?

Mediocre managers often fail to track clear metrics for their team’s performance. In extreme cases, supervisors simply keep an eye on how long their workers physically sit at their desks.

When workers telecommute, managers can’t see if they’re physically at their desks. While sitting behind a desk doesn’t qualify as work, lazy managers often let lazy workers skate by as long as they show up to work on time and put in a minimum effort to get a little work done.

None of that flies with telecommuting. Managers and workers alike need to get crystal clear on precisely what constitutes success for every single team member. Regardless of their position, every employee should have at least one key performance indicator (KPI) that reflects how well they’re doing their job.

For customer service reps, for example, these KPIs could include customer feedback ratings to indicate the quality of their service and the total number of customers served to indicate the quantity.

How to Avoid Performance Measurement Doom

If you manage a team, think long and hard about how to measure each of your direct reports’ performances. If you work for a company, ask your manager directly: “What metrics will you use to measure my performance, and what are your expectations?”

If your manager doesn’t provide a clear answer, ask them to think about it and get back to you. Without clear expectations and KPIs, neither you nor your employer can know how you perform. And without that knowledge, your job security becomes a matter of whim since you can’t point to hard evidence of your performance.

7. Social Isolation

Sitting at home by yourself all day takes a toll.

Humans are social animals. They need interaction with other people. Without a watercooler to swap jokes, stories, and shop talk around occasionally, telecommuters can get lonely.

Videoconferencing helps — a little. But Zoom is just not the same as face-to-face interaction.

My wife works at a school all day as a counselor. She literally talks to people all day every day, while I get almost no social interaction all day. When I come home from work, I start proposing happy hours or dinners with friends or anything to get out of the house and rub elbows with other people. All she wants to do is put her feet up on the couch.

If you don’t get social interaction at work, you need to get it elsewhere.

How to Avoid Social Isolation Doom

It helps to simply anticipate this challenge and plan for social interaction outside of work. Normally, that means meeting up with nearby friends or colleagues for lunch, taking classes at the gym, or making dinner or happy hour plans.

Amid the COVID-19 pandemic, it means video calls with friends and family or meeting privately with a friend or two. Consider walks, hikes, or other solo outdoor activities, which offer plenty of ventilation. I find that I don’t mind working alone all day if I can interact with friends at least three or four times a week outside of work.

Working at a coworking space or even a coffee shop can also help you feel less isolated (although this may not be an option currently due to the pandemic).

8. The “Work in Your PJs” Trap

I admit it: I work in athletic clothes, mostly because I work out midday, which helps me reset both physically and mentally.

But I’ve also built rock-solid routines around my work schedule after a dozen years of telecommuting. And even I put on more professional clothes for important calls — whether they’re videoconferences or not. Your clothes impact not only how others see you, but how you see yourself and how you think and behave.

Even athletic clothes are better than your pajamas, however. People love the thought of pajama work, but in reality, it’s a terrible idea.

Pajamas and sleep are strongly connected in most people’s minds. Think Pavlov and his dogs — classical conditioning and associations. A 2012 study in the Journal of Experimental Social Psychology found that people perform work tasks better when wearing clothes with “symbolic meaning.” For example, doctors did better work while wearing lab coats.

It’s also hard to feel clean and fresh in the pajamas you slept in the night before. Hygienic benefits aside, showering and feeling clean improves most people’s professionalism and performance.

How to Avoid Dress Code Doom

While you should keep professional clothes in your wardrobe for meetings with clients and vendors, you don’t have to sit at home in a suit all day. You do, however, need a work routine that includes real clothes.

Pick out some clothes to work from home in and never worry about what to wear to work again.

Man Working In Pajama Pants Suit Jacket Tie

9. Failing to Run Your Business Like a Business

If you’re working for yourself and think you can disregard administrative work, think again. You’ll probably end up doing more mundane administrative work than you ever did at your old day job.

Ignoring business basics, like paying your bills, preparing your taxes, and invoicing clients, is a surefire way to not only ruin your business but possibly trigger an audit with the IRS in the process.

Traditional jobs tend to come with paperwork, such as work reports, time sheets, travel expense reports, and accounts payable requests for freelancers and vendors. Still, each individual worker’s administrative work pales in comparison to the total amount needed to run a business.

Beyond administrative work, businesses need systems in place to streamline all repetitive tasks. Otherwise, entrepreneurs spend all their working time on mundane work that doesn’t actually generate revenue and quickly go out of business.

How to Avoid Mismanagement Doom

Schedule a certain amount of time each day for administrative tasks. Pay your bills, invoice your clients, order your office supplies, and process your mail during this time. Do it every day at the same time so it becomes part of your routine.

Also, set aside at least a few hours of every week for working on your business itself. That could mean hiring and managing virtual assistants, automating your bookkeeping through a platform like Quickbooks, documenting your business systems, and a hundred other steps to make your small business more productive and profitable.

10. Lax Billing & Invoicing Practices

Not getting paid by clients promptly — or at all — can quickly derail your business.

When you work as a W-2 employee, you usually take getting paid on time for granted. You don’t have to worry about issues like setting and enforcing clear payment policies.

Entrepreneurs and freelancers can’t take getting paid for granted. Instead, they need to create and enforce billing and payment policies.

When you send a professional-looking invoice immediately after you complete your job, you make it clear to your client that you expect to be paid, and fast. Include a large bold “Due Date” on all invoices to emphasize this point.

Some freelancers even ask new clients for deposits before agreeing to begin work.

If a client misses a payment due date, contact them immediately – Quickbooks even has a feature where you can send automatic reminders. Ask when they will deliver payment, and then calmly and politely explain that you cannot do any further work for them until they pay their outstanding balance. Remember, your chances of receiving payment decrease over time, so even if it feels uncomfortable, you need to draw a line in the sand early.

When you don’t follow through on demanding payment, clients assume you either don’t care about being paid or you’re a sloppy businessperson who won’t follow up on unpaid bills. Even clients that intend to pay might make your invoices a low priority if they think they can get away with it.

Don’t shy away from confrontation over payment because you’re concerned about maintaining a relationship with your client. Like any relationship, if you don’t set boundaries and expectations, it will eventually go sour. You don’t need nonpaying clients.

How to Avoid Deadbeat Client Doom

Put your payment policies in writing and, if possible, verbally explain them as well. Immediately after you finish a job or complete a task, send your clients a professional invoice, perhaps through a service like FreshBooks. The invoice should state the date on which payment is due as well as your client’s options for payment. Offer your clients more than one payment option to make it easy for them to pay you.

11. Motivation & Long-Term Vision

When you’re not surrounded by the career-driven energy of ambitious colleagues every day, it’s all too easy to slip into a rut.

Telecommuters often get comfortable, earning enough money to get by and losing sight of their long-term career goals. They don’t walk by the corner office every day, don’t chat with co-workers about the new promotion available, and lose sight of all the reminders they could do more challenging and rewarding work.

Not everyone feels driven to advance their career and pursue promotions. But when you never leave your house, even those with an inner fire often feel it dim quickly.

How to Avoid Motivation Doom

Write out your long-term financial goals and career goals. At least once a quarter, ask your boss about advancement opportunities within your company.

You can also listen to motivational and personal development audiobooks (or read the print versions) or attend motivational events and conferences. And most important of all, continue networking in your industry.

12. Failing to Network

Working from home, whether as an entrepreneur or telecommuting employee, makes it easy to disappear into your own little cocoon.

Yes, trade shows and industry events can be tedious. And during the COVID-19 pandemic, most are canceling or postponing or going 100% virtual this year.

Yet networking remains an essential way to stay relevant for employees and small-business owners alike. If you don’t budget time and money for trade shows, professional association memberships, masterminds, and other industry groups, you lose touch with those holding the power to make your career or business a success.

Stay involved in your professional community, stay relevant, and stay top-of-mind so no one forgets who you are. Participate in industry-specific social media groups. Email or reach out through social media to contacts in your industry you haven’t spoken to for a while. Whatever you do, don’t let your relationships grow rusty, despite physical social distance.

After all, more people find jobs through their personal networks than any other channel, according to a 2019 study by CivicScience.

How to Avoid Networking Doom

Go to at least two trade shows per year and spend 20 to 30 minutes each day keeping up with your industry. Program your newsreader to send you industry news and blog posts. You can also volunteer for professional association committees and projects.

Follow networking best practices no matter the discomfort. It takes effort, but clients are impressed by knowledge and commitment, which means more business for you.

Final Word

Telecommuting comes with a slew of benefits, from ditching the daily commute to a more flexible work schedule to being able to live and work anywhere in the world. But don’t believe the hype — it still requires work, and with every benefit comes a challenge.

That goes doubly for workers whose industries haven’t widely adopted virtual business models but were forced to during the COVID-19 outbreak. Many of my friends are teachers, for example, and every single one is struggling with telecommuting since their schools had no or limited online resources for teaching.

Without the structure imposed by a traditional workplace, you need to create your own structure and routines. If you want the freedom to work from anywhere, be prepared for additional responsibilities too.

G. Brian Davis is a real estate investor, personal finance writer, and travel addict mildly obsessed with FIRE. He spends nine months of the year in Abu Dhabi, and splits the rest of the year between his hometown of Baltimore and traveling the world.