Are You Ready to Be a Remote Worker? 5 Signs You Should Take the Leap

Not confident enough to leave your soul-crushing cubicle job for a remote position? These telltale signs you’re ready to make the jump say otherwise.


Why haven’t you ditched your terrible cubicle for the remote work life you’ve been jealousy eying?

If you’re nervous about successfully making the transition from office employee to remote employee — especially if you’ve been working for the same company for several years — this guide should put your fears to rest.

We’ll be sharing five surefire ways you’ll know you’re totally capable of going after the remote job you really want.

You Know You’re Ready to Become a Remote Worker When…

These warning signs become less subtle and more substantial:


#1. You’re SO Over Office Life

From long, stressful commutes to sharing a desk with a mouthbreather who never stops gossipping, office life can be a major drag and roadblock to getting your work done.

Yet over 90% of employees who start working remotely dig it so much they plan to work that way well into retirement — if they even choose to retire.

That’s because the ability to work where you’re most productive, during your most focused hours, and away from distractions makes for a better, more accomplished work life.

And if you’re already the most productive member of your team right now, you’ll do amazing as a remote employee, as you’ll see next.


#2. Your Time Management Skills are Fire

Do you constantly finish tasks on your to-do list before everyone else in your department even starts them?

Are you tired of slowing down your real work so you’re not inundated with time-wasting tasks just to fill your mandatory eight-hour shift?

Unless a remote position requires you to be available during a specific window, many remote workers have the flexibility to create their own schedule and fit in other activities they wouldn’t get to accomplish with traditional 9–5 set hours.


Here’s where the super productive get rewarded: you may not need to clock in a full eight hours of work every day if you accomplish everything in half the time thanks to your killer efficiency.

This leaves you open for a side hustle or part-time gig (if you’re not already juggling parenthood).

Solid time management skills also extend to knowing how to establish a work/life balance to avoid burnout.

Since one recent study shows 32% of remote workers have a hard time switching off from employee to personal time at the end of the day, you’ll want to master this skill too.

If you’re yearning for a work schedule that better fits your lifestyle, you’re in agreement with 41% of remote employees who do so solely for that reason — and the ability to work wherever they want.


#3. You See Everywhere as a Potential Workspace

When you start taking inventory of all the outlets, comfy chairs, and Wifi passwords at your local library, coffee shop, and brewery, your heart wants to work remotely.

And if you’ve already envisioned an area in your abode for your home office, with total confidence you can work there without your cat or the dishes distracting you, add a plus one to your win column too.

Because while certain types of people need the structure a traditional office setting provides to tell them when they need to get to work, others with self-motivation and discipline like you need your environment to inspire your energetic juices.

Not working so close to your teammates also helps you grow closer to them.


#4. You’d Rather Communicate with Your Coworkers Via DM

Remote employees work in teams made of coworkers living in different time zones all over the world.

So while there may be virtual meetings once a week, remote employees more commonly rely on project management tools and communication channels like Slack, Trello, and Skype to stay in touch.


If you’re pro-level with these and others like them — and you prefer using them to conference room meetings and emails — you’re already a step ahead of the game.

Spotting this final sign on our list means you’re definitely ready to leave your desk job in the dust.


#5. Adulting Officially Doesn’t Scare You

Many remote positions offer their employees all the perks of working for a corporate giant; other jobs may require you to sign on as a freelance contractor.

That means you’ll have to adult on your own by taking care of chores normally designated by your employer, such as:

  • Outlining clear goals and expectations. Many new remote workers feel they have to compensate for being able to work on the beach by overworking. Defining clear objectives and using project trackers from the start will help you know when you’ve done your job and when you can relax.
  • Payroll and taxes. Some remote employees receive their paycheck via direct deposit with all their taxes handled appropriately. Others may have to invoice for their time, get paid monthly instead of bi-weekly, and file a 1099 instead of a W-2 for their taxes.
  • Medical insurance and disability. You may be entitled to medical and disability benefits through your remote employer. But if your position doesn’t guarantee this, you’ll need to ensure you have a plan in place before you leave your current position to avoid a gap in coverage.
  • Vacation time. Though you may be able to take your work on the road, you also deserve unplugged time away from your day job. Contract remote employees very rarely receive paid time off so your vacation days may be days you won’t earn any money.
  • Expenses and write offs. This will also depend on your employer designation. If you’re incurring work expenses as a 1099, you’ll be able to write these off when you file your income taxes.


However, if you’re a company remote employee, these office needs may be reimbursed so you won’t have to pay for them out of pocket.

Many companies will provide a monthly stipend to pay for your home office or coworking space and cover supplies, setup, phone and internet, etc. to make your transition as easy as possible.


If you can handle these challenges on your own, you’re officially prepared for what most people consider the biggest downside to remote work.


The Hardest Part Is Just Starting

Don’t ignore these five signs you’re ready to work remotely.

Instead, it’s time to check out the available remote positions over at We Work Remotely, the best place to find listings for jobs not restricted by commutes or a particular geographic area.

You’ll join more than 160,000 monthly users who post and apply for remote jobs in:

  • Programming
  • Design
  • Customer support
  • Marketing and writing
  • Business/Executive management
  • Logistics
  • Finance
  • And so much more

When you find the virtual job of your dreams, check out this guide on everything you need to know before applying for remote work next.

And don’t worry, these five signs prove you’ve got this!