Yes, You Can: Overcoming 3 Common Obstacles to Working Remotely

Yes, You Can: Overcoming 3 Common Obstacles to Working Remotely shares three common challenges that could possibly arise from working remotely and some best practices for crushing them.
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The way people work is changing and we here at WacoWork are excited to be a part of this evolution.

For many industries, the days of going to an office Monday thru Friday 8 AM to 5 PM are giving way to digital nomads joining coworking spaces, setting up home offices and/or hunkering down at coffee shops.

Journalist, John Kennedy, says that “remote working will rival fixed office locations by 2025.” Globalworkplaceanalytics.com statistics show that “regular work-at-home, among the non-self-employed population, has grown by 140% since 2005, nearly 10x faster than the rest of the workforce or the self-employed.” In fact, a study conducted by IWG “found that 70 percent of professionals work remotely — a phenomenon known as telecommuting — at least one day a week, while 53 percent work remotely for at least half of the week.”

Working remotely certainly has its benefits (such as decreased stress, decreased commute time and increased autonomy over one’s schedule). However, as a career professional in this new day and age, it’s important to understand and anticipate obstacles from this new reality.

Here are the three common challenges that could possibly arise from working remotely and some best practices for crushing them:

1. Out of sight, out of mind

You’ve set big goals for yourself. You are driven, focused and ready to leave your mark in your both your company and your industry. While working remotely has given you a sense of sovereignty over your calendar, it also has presented the unique challenge of literally staying in front of your boss, presenting your bright ideas and showcasing your know-how.

Let’s face it: even if you’ve never worked a day in sales, you’re still a salesperson. It’s important that you stay visible, tuned in and that people know what you’re up to and how you contribute to the company’s success. The reality is that you are the only person who really knows what it takes to do your job. You’re the one who knows what a pain it is to upload the financial model into Sharepoint or maybe you’re the one who painstakingly designs all of the company’s marketing materials. Sometimes you feel like you’re herding cats when trying to set a time that works for everyone on your team, yet you finesse it every single time.

Here’s some ways to stay visible and in tune with the direction your company is headed:

Set up a weekly touchbase with your direct supervisor.

Even if it’s just 10 minutes a week, use this time to let your supervisor know all about your wins and your progress. You can also use this time to address any concerns or challenges you’re facing, but remember to keep the overall tone of this touchbase positive and focused on moving forward.

In order to prepare for your check-in call, make sure to keep track of your wins, progress and compliments that you’ve received from colleagues throughout the week. Plan your talking points before the meeting. Preparation always helps to alleviate nerves, so stay on top of your game. Furthermore, always end the touchbase by asking your supervisor how you can improve and what you should be keeping in mind about any projects, job duties or anything in general.

Sure, it’s easier to send all of this in an e-mail and both you and your supervisor may be tempted to do this because you’re both busy. However, the point is that you are visible and you are actually speaking to your supervisor. This gives you an opportunity to practice talking about yourself and the value you add. This touchbase also gives you the opportunity to continually build rapport with your supervisor.

Try your best to conduct these meetings every week with your supervisor, so that you remain a constant source of progress and positivity for your boss.

Use technology to your advantage.

Cultivating relationships is the name of the game and it’s time to use technology to your advantage. Whether it’s Slack, Zoom, Skype, etc., stay in touch with your colleagues and counterparts throughout the company. Always offer a helping hand with any projects and think of ways to help your colleagues shine.

Best practice: Always keep correspondence professional, keeping in mind that your company probably stores (and maybe even reviews) employee conversations.

If there is a team Slack channel (that isn’t work related but rather dedicated to team culture), consistently showcase your humor by posting nerdy Excel jokes, interesting articles you’ve read, quotes that have inspired you, trivia questions. Encourage your colleagues to do the same. Remember to always keep it clean and classy. You’re a leader in everything you do. Share thought pieces that you’ve written and encourage your colleagues to give you feedback.

Seek out a company mentor.

A mentor can play a crucial role in your rise at the company. He or she can give you ideas on how to shine at work, how to navigate the political landscape and can show you how to reframe your view point. Keep in mind that your mentor does not have to work in the same department as you. In fact, choosing a mentor who works in marketing may actually work to your benefit because it allows you to get out of your Finance comfort zone.

Plan on connecting with your mentor at least once a month. Prepare for your meetings beforehand in order to maximize the time you have with him or her. Keep your questions high level, big picture and always end the meeting by asking for any additional insight or contacts that may prove beneficial. Also, always ask if there is anything you can help out with, even if there isn’t anything for you to do. This just lets your mentor know that you want to give back as much as you can.

2. Focus, focus, focus

When you’re working remotely, it’s up to you to really own your calendar and stay on top of your duties. The same way you wouldn’t binge watch Game of Thrones at the office, you wouldn’t go down the Netflix rabbit hole while on the clock at your home office (aka your couch).

Your consistent discipline and determination is what’s going to set you apart from the rest. Here are some ideas for honing your focus and contributing your best:

Establish routines.

In his book, Uncertainty: Turning Fear and Doubt Into the Fuel for Brilliance, Jonathan Fields posits that establishing routines creates a sense of comfort, certainty and focus for the working professional. Everyone from artists, entrepreneurs and team leaders benefit from routines because they infuse a sense of familiarity into our everyday experience. Whether it’s taking a coffee break promptly at 10 AM or standing up to stretch every hour on the hour, simple routine actions can make a big difference in helping remote workers to maintain focus throughout the day.

Batch your work.

Whether you are a Social Media Manager, Financial Analyst or Director of Sales, your schedule can totally benefit from batching. Batching is a time management technique that involves doing similar tasks all at once. Joshua Leatherman, CMO of Service Express says that “every time we become distracted, it takes an average of 15 minutes to regain complete focus.


Conduct a time audit to understand what repetitive tasks you do throughout the work week. See where you can group together similar tasks and perform those all at once. For example, instead of writing Instagram captions every single day, perhaps you set aside Tuesday mornings to hammer out copy. Or instead of checking your e-mails intermittently throughout the day, check them once in the morning, once in the afternoon and once in the evening.

Try it out and don’t be afraid to make adjustments that work for you.

3. Setting clear boundaries

One of the benefits of working in a traditional office space is that usually when you go home for the day, you leave your work at the office. Not so with working remotely: your work is literally with you wherever you go. As long as you have internet service, some tablet or laptop and your smartphone, you can set up shop wherever. The temptation to keep on working abounds and can keep you from taking much needed downtime.

However, for the sake of your mental health, it’s important to set clear boundaries between your work life and your personal life. Rest from work queries gives your brain an opportunity to rejuvenate and come up with solutions. If you’re constantly on the go, putting out fires and working, you are at a higher risk of burnout and health problems.

Here are some ways that you can set and honor your boundaries:

Plan your work and work your plan.

You are the CEO of your life and it’s time to start acting like it. At the beginning of each week, analyze your calendar so that you can see the big picture in your schedule:

  • Take note of any meetings, deadlines and projects that you’ll be working on. Prioritize these based on their sense of urgency and how they ultimately contribute to your company’s bottom line.
  • Set aside time in your schedule for meals, exercise, appointments and downtime. Honor these personal times as if they were a meeting with the CEO of your company.
  • Factor in time for the unknown. You may feel the need to schedule every single moment of your day, but it’s more productive to leave in some open space. There will be things that come up that you cannot possibly anticipate beforehand and having open space allows you to move things around in the event that you’ve got to run your kid to the doctor at 3 PM.

Join a coworking space.

Not to toot our own horn, but coworking spaces like WacoWork rock. You enjoy the benefit of community AND getting sh!t done (which is our mantra).

Sure, you can set up shop at different coffee shops throughout your city, but you’ll never have consistency when it comes to amenities. One coffee shop may have limited seating and fast Wi-Fi, while the other doesn’t have enough outlets to charge your laptop. A coworking space solves all of those issues and provides you a consistent experience. Plus, you can maximize your membership and continue to climb the corporate ladder.

Even more importantly, you can set clear boundaries by leaving your work at work at the end of the day.

Overall, it’s time to reframe the way you view obstacles — they are simply opportunities for you to flex your problem solving and creative muscles. The number of people who work remotely will continue to rise as companies look to decrease expenses such as office space and employees look to decrease stressful commutes. You have a chance to set yourself ahead of the crowd and to crush any challenges that present themselves to you.

We here at WacoWork are rooting for you.

Now it’s your turn. Comment below and let us know what remote working obstacles you are faced with and how you handle them.


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LaTisha Cotto

LaTisha Cotto is a Master Life Coach + WacoWork Resident Cheerleader. She loves Jesus, her beautiful daughter and Adidas Originals. If you see her around WacoWork, feel free to say, “Hi.” For more of her feel good vibe, sign up for her Resource Library HERE.

1 Comment

  1. A Freelancer's Guide to Avoiding Burnout - WacoWork on June 3, 2019 at 11:22 am

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