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The 12 Biggest Challenges to Working from Home

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As millions of workers around the world begin telecommuting for the first time due to the COVID-19 pandemic, few know what to expect. They only know the image spread by all the "Work from home!" ads on the Internet.

I've been telecommuting for over 12 years, first as an employee, and later as a freelancer and 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 a lot of hidden challenges that aren't mentioned in the sexy ads.

Managers and executives don't implement "annoying" workplace policies like dress codes and standard work hours because they like to annoy their employees. Instead, these policies help employees work efficiently and keep companies profitable. And this work-from-home rhetoric leads to misconceptions about what telecommuting is really like - misconceptions that contribute to the high rate of business failures among entrepreneurs and poorer performance among many telecommuters.

When you first start telecommuting or are thinking about starting, beware of these risks and challenges. The better you recognize them, the easier it will be to mitigate them and succeed as a telecommuter or small business owner.

Own time management and time management

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

Except it doesn't work that way.

The concept of "normal business hours" is still in use around the world because it works as an efficient time management tool. When you have set hours, you know when you need to work and when you are 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 will be working.

Without this structure, many home-based workers find themselves in big trouble. They sleep in, put everything off, and tell themselves they'll get it done later. Suddenly, they look at the clock and realize their kids will be home from school soon - and they haven't done what they planned to do.

This presents them with a choice: work through the evening or just keep procrastinating. Many conventional employees complain about the structure of a regular schedule. But it benefits them much more than they realize.

How to avoid time management disaster

Set your work days and hours and stick to them. In most cases, this means either keeping regular business hours or basing your work hours on your spouse's or children's schedule. A conventional schedule not only makes you more productive, but it also allows you to spend time with the people who are important to you.

For example, I work from about 7:30 a.m. to 12:30 p.m., then take about a 90-minute break to work out and eat lunch. After that, I work again from 2 p.m. to 6 p.m. On Saturday morning, I usually work two or three hours as well.

But even if you choose to work the tried-and-true 9 to 5, there are significant benefits to remote work. You don't have to commute to work, so you can sleep in later. Plus, you don't have to get permission if you need to run important errands like doctor's appointments.

Blurred line between personal and professional life

On the other hand, when you work from home, you no longer have a clear geographical separation between your workspace and your personal space.

Ideally, your home is a place of relaxation, safety and security. It's a place where you unconsciously slip into a calm, relaxed state and leave the stress of the workday behind.

Working from home breaks this neat mental division. Many telecommuters complain that they feel like they never get out of work. They always feel compelled to check email or do "one last thing."

In other words, they find it hard to switch off and relax. Ever.

How to avoid a blurry work-life doom

You need to set up a physical space to work that is separate from the rest of your home.

For many, that means a home office. My business partner maintains a home office with a lockable door and a big warning sign to never disturb her when the door is closed. It took a while, but her family eventually learned to respect the rules. She eventually doesn't show up at their work to interrupt them.

I pay for access to a co-working space and find it worth every penny. It creates a clear separation between my work and personal life and helps maintain a work-life balance.

When I work from home, I have an agreement with my wife that she will not disturb me unless the world is ending. I invested in a pair of excellent noise-canceling headphones that block out family noise and keep me firmly grounded in my work.

If you have an extra bedroom, library, study, formal dining room or other room in your home that is rarely used, consider turning it into a home office, even if it's temporary. If possible, close the doors while you work and hang a "do not disturb" sign.

You may be able to claim the home office tax deduction if you choose to have 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 you draw the spatial and temporal boundaries between your work life and your personal life, the better you'll be able to separate the two.

Distractions

Even if you opt for a set schedule and have your own space to work, it can prove difficult to stay productive during work hours when you work from home.

Surrounded by your personal belongings and reminders of chores, it's hard to focus. Distractions like your TV, books, and laundry start calling out to you. Even though you planned to work until 12:30 p.m. before taking a lunch break, you find an excuse to get off work early. If your family members also happen to be home, they won't hesitate to interrupt you at every opportunity.

That's one of the many reasons I avoid working from home - to eliminate those distractions and maintain a solid barrier between my work life and my personal life.

How to avoid distractions

It helps to physically retreat to a separate home office. But also make sure you remove distractions from your workspace. If there's no TV or books nearby, you're less likely to be distracted.

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

Set rules with your family so they don't disturb you while you're working remotely. Tell them to behave as if you were in the office.

Then find out other ways to avoid distractions while working at home, as this is a much bigger challenge than most office workers realize.

Reduced supervision & management

People love to bitch about their bosses. But bosses serve an important purpose: they set direction and supervise your work. Not only do they tell you what to do, but they also give you feedback on your progress.

When you work from home, you typically receive less supervision and guidance. Your boss (or clients, as the case may be) usually doesn't give you as much guidance - guidance that many remote workers desperately need to stay on track.

How to avoid directionless doom

If you work for an employer, stay in close communication with your supervisor. Ask him what projects he wants you to prioritize and when he expects you to reach each milestone.

Talk to him or her at least once a week about your progress, your challenges, and ideas on how to address those challenges. Keep them informed so they can give you better feedback and direction.

When working for yourself, start by setting general weekly goals. Then set three high-priority tasks each morning. You can sprinkle in smaller tasks like getting emails done when you have five minutes, but keep the larger, high-priority tasks in mind.

All of these tasks will help you answer the most important question: What is the most important work I can get done today?

Communication and coordination challenges

It's hard enough to have productive face-to-face meetings to coordinate the efforts of different team members to stay aligned. When everyone works from home, it becomes even more difficult to stay on the same page.

People rely on nonverbal communication when they speak. But emails, phone calls and even video calls leave out much of the nuance in our communication. Just think back to the last time someone misinterpreted an email or text message you sent, to give one example.

This problem is so pervasive 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 businesses to stay in touch and organized. GoToMeeting is another popular choice for businesses to stay in touch via video conferencing.

How to avoid the communication breakdown

If you're a boss or supervisor, schedule weekly phone or video conference meetings with your key teams. Review each team member's progress against previously agreed-upon deliverables and goals. At the end of each meeting, set new tasks and goals for each individual. Ask each responsible team member to review them to ensure they fully understand them.

Similarly, team members should confirm their priorities and tasks with their boss or supervisor and colleagues before setting out to complete them. Virtual communication leaves too much room for ambiguity, so be sure to review tasks at the end of each call, conference or email. The same goes for self-employed people communicating with clients and vendors.

For day-to-day communication, use project management and collaboration tools such as Slack or nTask to track all communication and ensure all team members stay up to date on the same platform. These enable trackable communication threads between two or more people, assignments, file sharing, private messaging and more, replacing email for consolidated, fast communication without lost messages, spam or distractions from work.

Unclear performance metrics

What metrics does your boss - even if it's you - use to measure your job performance?

Mediocre managers often fail to track clear metrics for their team's performance. In extreme cases, supervisors simply keep track of how long their employees are physically at their desks.

When employees telework, managers can't see if they are physically at their desk. Although sitting behind a desk is not considered work, lazy managers often let lazy employees get away with it as long as they show up for work on time and put in a minimum amount of effort to get a little work done.

None of this works with telecommuting. Managers and employees need to be clear about what exactly makes each team member successful. Regardless of position, every employee should have at least one key performance indicator (KPI) that reflects how well they are doing their job.

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

How to avoid the demise of performance measurement

If you manage a team, think hard about how you measure the performance of each of your direct reports. 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 give 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 what your performance looks like. And without that knowledge, your job security becomes a matter of whimsy, as you can't provide hard evidence of your performance.

Social isolation

Sitting at home alone all day takes its toll.

Humans are social animals. They need interaction with other people. Without a "water cooler" to share jokes, stories and shop talk, telecommuters can get lonely.

Video conferencing helps - a little. But Zoom just isn't the same as face-to-face.

My wife works all day in a school as a counselor. She literally talks to people all day, while I have almost no social interaction all day. When I get home from work, I suggest happy hours or dinner with friends or anything to get out of the house and socialize. All she wants to do is put her feet up on the couch.

If you can't get social interaction at work, you need to get it somewhere else.

How to avoid the fate of social isolation

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

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

Working in a coworking space or even a coffee shop can also help you feel less isolated.
(Although that may not be an option right now because of the pandemic).

The "work in pajamas" trap

I'll admit it: I work in gym clothes, mostly because I work out at lunch, which helps me recover physically and mentally.

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

Even athletic wear is better than your pajamas, though. People love the thought of pajama work, but in reality it's a terrible idea.

Pajamas and sleep are firmly linked 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 performed work tasks better when they wore clothes with "symbolic meaning." For example, doctors performed better when they wore lab coats.

It's also hard to feel clean and fresh in the pajamas you slept in the night before. Aside from the hygienic benefits, showering and feeling clean improves professionalism and performance for most people.

How to avoid dress code doom
Although you should have professional attire in your closet for meetings with clients and vendors, you don't have to sit at home in a suit all day. However, you do need a work routine that includes proper attire.

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

Do not run your company like a business

If you work for yourself and think you can neglect administrative work, you're thinking wrong. You'll probably end up doing more mundane administrative work than you ever did in your old 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 potentially trigger an IRS audit.

Traditional jobs usually involve paperwork, such as work reports, timesheets, travel expense reports, and accounts payable requests for freelancers and vendors. Yet the administrative work of each employee pales in comparison to the total amount required to run a business.

Beyond administrative work, businesses need systems to streamline all repetitive tasks. Otherwise, business owners spend all of their work time on mundane tasks that don't generate any real revenue and are quickly out of business.

Here's how to avoid mismanagement woes

Schedule a specific time each day for administrative tasks. During this time, pay your bills, invoice your customers, order your office supplies, and process your mail. Do this at the same time every day so it becomes part of your routine.

Also, schedule at least a few hours each week to work on your business itself. That could mean hiring and managing virtual assistants, automating your accounting through a platform like Quickbooks, documenting your business systems, and a hundred other steps to make your small business more productive and profitable.

Lax billing and invoicing practices

If your customers don't pay you on time - or at all - your business can quickly be derailed.

When you work as a W-2 employee, you typically take getting paid on time for granted. You don't have to worry about things like establishing and enforcing clear payment policies.

Business owners and freelancers can't take payment for granted. Instead, they need to create and enforce billing and payment policies.

When you send out a professional-looking invoice immediately after your work is completed, you make it clear to your client that you expect to be paid quickly. Include a big, bold "due date" on all invoices to emphasize this point.

Some freelancers even ask new clients for a deposit before they start work.

If a client misses a due date, contact them immediately - Quickbooks even has a feature that lets you send automatic reminders. Ask when payment will be made, then calmly and politely explain that you can't continue working for the client until they pay the outstanding balance. Remember that your chances of receiving payment diminish over time, so even if it feels uncomfortable, you need to draw a line early.

If you don't collect payment, your customers will assume that you either don't care about payment or that you're a sloppy businessperson who doesn't follow up on unpaid invoices. Even customers who intend to pay may give your invoices a low priority if they think they can get away with it.

Don't shy away from confronting payment because you're worried about your relationship with your customer. Like any other relationship, it will eventually fail if you don't set boundaries and expectations. You don't need non-paying customers.

Here's how to avoid customers who are unwilling to pay
Put your payment policies in writing and explain them verbally if possible. Send your clients a professional invoice immediately after completing a job or task, perhaps through a service like FreshBooks. The invoice should include the date payment is due and the payment options for your client. Offer your clients more than one payment option to make it easier for them to pay.

Failure to network

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

Yes, trade shows and industry events can be annoying. And during the COVID-19 pandemic, most will be canceled, postponed or held 100% virtually this year.

However, networking is still an important 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'll lose touch with those who have 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 via social media to contacts in your industry that you haven't spoken to in a while. Whatever you do, don't let your relationships get rusty, despite physical distance.

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

Here's how to avoid networking disaster
Attend at least two trade shows a year and spend 20 to 30 minutes each day keeping up to date on 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 how inconvenient. It takes effort, but clients are impressed with knowledge and engagement, which means more business for you.

Final Word

Telecommuting brings a number of benefits, from eliminating the daily commute to a more flexible work schedule to the ability 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 double for workers whose industries haven't yet widely embraced virtual business models, but were forced to do so during the COVID-19 outbreak. For example, many of my friends are teachers, and every single one of them struggled with telecommuting because their schools had no or limited online resources for teaching.

Without the structure that a traditional workplace provides, you have to create your own structure and routines. If you want the freedom to work from anywhere, you also need to be prepared for additional responsibilities.

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