Office Productivity Soft Skills

15 minute read

How to Work Remotely: A Beginner's Guide to Landing a Remote Job

Devan Ciccarelli

Devan Ciccarelli

Are you considering a career change to work remotely? You're far from alone. Statistics from Credit Summit indicate that over 46% of the American workforce are freelancers in an expanding gig economy, and that 79% of people currently working as independent contractors prefer freelancing to working in a traditional job.

While you probably won't miss waking up early, commuting in traffic, wearing stuffy business suits, or listening to your coworkers gossip, being a remote worker isn't all pajama parties and sleeping in.

That's why I'll be sharing pro tips and answers to the biggest questions about how to work remotely in this guide.

We'll cover topics together such as:

  • How to tell if remote work is right for you
  • Where to find remote jobs
  • Tools and skills you'll need for remote work
  • How to set yourself up for success as a remote worker

If you learn remote work is your calling, I'll be sharing all the tips you need to start as a beginner -- including what working remotely really requires.

But before we get to all that, it's crucial to figure out exactly why you want to work remotely and if you have what it takes to be successful at it first.


4 questions to find out if you have the skills needed to work remotely

You don't want to jump ship from your current job only to learn remote work isn't right for you.

So that's why it's a smart idea to lay down a few foundational items first.

Write down the answers to these four questions and you'll have a better idea of where you stand as we move on:

1. Why do you want to work remotely?

This may be the hardest or easiest question depending on how long you've been thinking about remote work.

So ask yourself if you want to work remotely to ditch the downsides of a traditional office job (i.e., hectic commutes, distracting coworkers, Hawaiian shirt Friday, etc.) or because you envision a new way of life for yourself.

While remote workers usually have a flexible schedule and more time for family, side hustles, and exercise, it doesn't necessarily mean they put in fewer work hours, which brings us to the next question.

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2. Can you manage your workload on your own? 

Working remotely requires just as much discipline -- if not more -- than a traditional 9-5 job. 

That's because without a supervisor over your shoulder, the temptation to push off your work and scramble to complete it all before a due date becomes very real.

So if you don't have the discipline to manage your own work time and develop your project management skills, this could be very challenging for you.

Not to mention you won't have your coworkers around to keep you in line or help you out.

3. Would you feel comfortable working alone all day, every day?

While your coworkers may get on your nerves, many people find the transition to remote work to be very lonely. 

So only you can predict how you'll feel about staying in touch with your coworkers remotely instead of conversing face-to-face every day. 

This is one skill many new remote workers have to develop on their own. 

But you'll also need experience with different project management tools as well.


4. Do you have the skills and experience remote employers are looking for?

Since remote workers can't run down the hall to speak with their managers or coworkers, it's essential they know how to use collaborative software like Microsoft Office and Google Drive.

If you're not yet familiar or comfortable with these tools, it pays to level up your education and certifications before looking for remote work.

You'll also want proficiency in communication and project management tools such as Slack, Trello, Asana, Basecamp, etc. 

You'll find some skills are more prevalent in a remote environment, like graphic design and coding work.

As you may have already experienced, it doesn't matter where you work in these fields which means more companies are turning to remote workers to fill these positions to help expand their talent pool.

So if you're looking to switch gears into these fields or you want to brush up or take your skills to the next level, consider taking design or development courses to strengthen or add to your skill set.

This simple step helps you stand out from other remote workers when applying to jobs and tells employers you can handle any role with ease -- even if it's your first time working remotely. 

Your learned skills will also help your transition to remote work since you'll already be familiar with the tools everyone on the team is using.

Now that you know what it's going to take to work remotely, you may think you're ready to start sending off resumes.

But there's one more big point to consider before embarking on your remote job search.

Who do you really want to work remotely for?

There are two branches of remote work: those who freelance and those who work remotely for a company.

Working remotely for a company is different than working remotely and freelancing on your own.

As with any job, there are pros and cons to consider with each route:

Working remotely for a company means you'll still have the luxury of a steady paycheck and a consistent workload.

The only real challenges here are managing your time, avoiding distractions, and combating feeling isolated and lonely at times as you do your work outside of a traditional office setting. 

If your reason(s) for wanting to work remotely focus on external issues such as commutes and crowded office space, this option will eliminate them so you can live as a busy worker bee.

But for those avidly trying to break free from the confines of corporate culture, a remote job working for a company will essentially be the same thing you're trying to leave.

So a full-fledged freelancing route may be a better option, despite the extra obstacles.

Working remotely as a freelancer means the added pressure of finding clients, creating invoices, and collecting payments from customers falls solely on your shoulders (it's worth learning how to use Excel for these freelance tasks).

And this doesn't always go according to plan.

Certain clients may pay you once a month while others won't send you a check until two months later and three follow-up email nudges.

For many just starting out with remote work, this is a tall order to take on and one that usually sends people straight back to a 9 to 5 cubicle if not planned for properly.

So if you don't have this internal drive pushing you to carve out your own path of entrepreneurship, working remotely for a company may be a less stressful transition for you.

But if you have that tenacity, freelancing will be the most rewarding since you'll be your own boss.

If you're still on the fence about which route may be best for you, your earlier answers to the questions about why you want to work remotely may be a great way to see which path you should explore and where you should focus your attention.

Once you make this decision, you'll be ready to move on to this next step: finding the remote job of your career dreams.

Visit these job boards for the best remote jobs

Now that you know more about working remotely, you're probably wondering where you should look for a remote job.

The usual job boards won't be your best place to start searching. The good news is there are plenty of other sites to choose from.

So once you decide whether you want to freelance or find a remote job with a company, you'll need to look at those specific job boards.

For those hoping to work remotely for a company, try these three sites:

1.  We Work Remotely

We Work Remotely connects companies with remote workers from all over the world.

You can view a list of their current job openings in a number of different fields such as:

  • Marketing
  • Development
  • Programming
  • Design
  • Customer Support
  • Copywriting
  • Business Management

2. also offers a plethora of job listings to choose from.

On top of the roles We Work Remotely recruits for, you'll also find open positions for employees in:

  • Sales
  • Project Management
  • QA
  • Healthcare
  • HR
  • Accounting
  • Teaching
  • Executive and virtual assistants

3.    Remote

Remote works a little differently than the first two in that job seekers create a profile and relevant positions are sent to them based on their matching skills.

According to the site, your profile is also passed around to any employers looking for candidates that fit your skillset, which can further increase your chances of landing your next remote job.

On the other hand, if you're looking for gigs or freelance work, it's better to find job boards solely focused on this niche.


Job boards for remote freelancers

Be careful of content mills when you first begin your freelance job search. 

A content mill is a site promising work to freelancers but when they onboard, they're inundated with low-paying jobs, fight in bidding wars, pile up unpaid invoices and deal with many other headaches.

To take home more pay while avoiding some of these problems, check out these freelance job boards instead:

  • Problogger is a job board for freelance writers
  • Authentic Jobs connects graphic designers to paying gigs 
  • Awesome Web posts jobs for freelancers in web design and development

As you start applying for jobs, there are a few more steps you can take to ensure you're ready for your first day of remote work.

How to set yourself up for success

Instead of waiting for the green light from potential remote employers, it's better to get yourself ready for remote work even before you land your next gig using these pro-level tips:

1. Create a dedicated workspace

Where you can sit and focus without being tempted by distractions such as the TV, video games, or your cat.

Even if you only have a small square of space on your dining table to work with at first, make sure you keep it tidy with everything you need right in that same location.

If you have to move junk off your "desk" every morning, you'll waste time and productive work hours. So always keep your workspace neat and free of distractions.

Try to stay off the couch and as far away from the kitchen as possible too. 

It's hard on your back to sit on the couch all day and you may find it leaves you unmotivated and too sleepy to get anything done.

And unlike working in an office where everyone can see you snacking in the break room instead of working, you'll be more tempted to graze your vending machine (i.e., fridge) during the day when no one is watching.

In keeping with separating your personal and work life, consider getting a dedicated business phone number. This will keep you organized and looking professional to your prospective clients.

On top of setting up your workspace for a productive day of remote work, you'll also want to figure out your most productive work schedule. 

2. Establish a schedule and stick to it

Start paying attention to your work habits and most productive hours, then try to only work during that time to increase your efficiency and accomplish more.

Without a commute, you may want to work earlier and finish your day when most people are leaving for lunch.

Or you may want to squeeze in healthy activities like working out, meditating, or meal prepping for the day and shift your work hours to a later time slot.

As long as your remote position doesn't require you to be at your computer for a set schedule during the day, you can experiment with what works best for you.

Try mapping out a new schedule to include when you want to work, when you'll take a break for lunch, and when you'll take breaks in between to see how a typical day might play out.

You can practice this updated schedule on weekends or as you start to transition to working full-time remotely.

Watch how you feel and make any adjustments before getting locked into a rigid schedule that doesn't work for you.


3. Outline an agenda with priorities

It also helps to have a clear outline of what your month, week, and day will look like work-wise.

Since there's no one looking over your shoulder to micromanage your work, using a to-do list will help you stay on track and focused on the tasks at hand.

A good rule of thumb is to prioritize your tasks with the most important ones first.

Make the top task your sole priority and don't complete any others until this one is officially off your plate.

Keep track of your progress to see if you're adjusting to remote work or if you need to make a few additional tweaks to get it right, such as your work method.

4. Experiment with different productivity techniques

You may notice your productivity start to wane as your legs get numb and stiff from sitting at your desk for too long.

That's why you need breaks built into your schedule.

Breaks aren't just important to give your eyes a rest and increase circulation in your body, they're also critical for staying sharp and concentrated on your work so you don't burn out. 

One productivity method called The Pomodoro Technique is quite popular with remote workers because it mimics what happens when you're working in a traditional office.

Similar to taking water cooler and lunch breaks, you'll:

  • Work for 25 minutes, then take a 5-minute break. 
  • Work another 25 minutes, then take another 5-minute break. 
  • Repeat this process for a total of four 25-minute work increments and you'll earn a 30-minute break.

During your break time, you may choose to stretch, get lunch, walk your dog, or catch up on messages.

Bonus: Learn from productivity pro, Francesco D'Alessio about the best Pomodoro apps.

If you're working from home or a co-working space, you may run into people or your Chatty Cathy neighbor who will want to talk your ear off.

Do this enough times and you'll become their go-to time waster, which won't help you make any progress work-wise.

If this is the case, you may want to try running in place, having a quick dance party, or doing a few jumping jacks during your breaks to get your heart rate up and blood flowing to your extremities (as long as your doctor says it's okay).

Without getting stuck in distraction quicksand, you'll combat the effects of sitting too long and wake up your brain if you're feeling sluggish -- both of which can easily happen when you work from home.

So now that you know more about how to work remotely, our final question is: will you?

Are you ready to work remotely?

If, after reading this guide, you still feel remote work is right for you, awesome! 

Your next steps are to set yourself up for success and apply to remote jobs.

Then it won't be long before you're able to quit your traditional 9 to 5 office gig and begin the transition of working remotely like you've always wanted.

And if you love the thought of working remotely but lack the skills or confidence to compete with candidates from all over the world, you may want to consider enrolling in online training courses to get yourself up to speed faster.

Once you do, you'll put yourself in a better position to land your next dream (remote) job and work happily ever after.

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Devan Ciccarelli

Devan Ciccarelli

Crafting fluff-free content is Devan’s jam. When she’s not writing for GoSkills, you’ll find her outside reading, soaking up the sun, or hiking her next adventure.