8 Tough Questions To Ask Before Committing to a Fully Remote Job

In this guest post, Jeanna Barrett discusses the most important questions you may need to ask before committing to a fully remote job. Founder and Chief Marketing Expert of First Page, an award-winning growth marketing agency, Barrett uses her experiences of going from Silicon Valley to Belize as a basis for successful planning and transitioning to the remote workplace.

When I traded in my fast-paced corporate gig to work from the shores of Belize, I asked myself a lot of questions. Primarily, am I insane? Maybe a little. You’d have to be to give up the security and stability of the “normal” 9-to-5 office job, right? Nah. What you have to be is daring. Fearless. An out-of-the-box thinker. But what you also have to be is smart. Careful. Calculated. It takes a lot of planning before committing to a fully remote job. 

The onset of the pandemic brought working remotely into the spotlight, and now you might be thinking you’re ready to take the plunge into full-time, fully remote work. Maybe you want to travel around the world while still earning a steady paycheck. Or maybe you want a better work life balance and more time at home with the family. Maybe you just really like working in your jammies. Whatever the reason, the remote work and work-from-anywhere lifestyles are within your reach, but you have to ask yourself a few key questions before you get started.

Pop quiz time!

Question #1: Am I Actually Crazy?

I’m lobbing a softball question here because I already know the answer. No, you’re not crazy. You’re willing to take risks to pursue the life you want to live. Share your goals with those in your circle who will be supportive, but also challenge you to think through any potential hiccups. Avoid the naysayers. You won’t change their minds, and it will only lead to second-guessing yourself.

Question #2: Do I Have What it Takes?

If you’ve been working remotely this last year, you probably already have a good idea of this. But committing to a fully remote job requires some answers of its own. Are you motivated to complete your work, even when you’re not in the office? Do you get your tasks done on time without a manager over your shoulder? Do you have the tools and resources you need to excel and time management and stay productive? If so, you’ve got what it takes!

Question #3: Where and How Should I Work?

The great thing about the work-from-anywhere lifestyle is that the name is pretty darn accurate. Thanks to technology, video capabilities, and extensive Wi-Fi coverage, you actually can work from just about anywhere. Still, you have to make sure your work environment is conducive to, well, working. Here’s how to figure out exactly what you need to succeed:

  • Ideally, wherever you are, you’ll need high-speed internet access, lots of outlets (or spare batteries), and minimal distractions. 
  • Ask yourself how you’re going to get your work done. Will you be available during typical business hours? If not, can you handle completing your work after those hours? What time zone are your colleagues in, and will that work with your schedule? 
  • If you’re planning to work primarily from home, ask yourself what your backup office spaces will be. Where can you go when you need a change of scenery or a break from the chaos of family members and pets? Have a few options lined up and research their hours, Wi-Fi availability, and openness to workers who linger over a cup of coffee for hours on end. 
  • Consider coworking spaces. These shared offices are cropping up all around the U.S., and they offer numerous benefits. You’ll also get the opportunity to work with other like-minded individuals (and there’s almost always a pot of coffee brewing).

Question #4: How Will I Manage Work-Life Balance?

The great thing about going fully remote is that it allows you to work how and when you want. That can also be the terrible thing about going fully remote. When work and home blur together, it’s harder to set boundaries and compartmentalize your tasks. Protect your time. Plan ahead, and know from day to day which hours are dedicated to working time and which are set aside for downtime and family time. When you’re on “your time,” don’t be afraid to silence your phone and shut down the laptop. Remember that working from home shouldn’t mean you’re constantly on the clock.

Question #5: How Will I Stay Connected?

It depends on the job. If you’re working for a fully distributed company, they will have their own tech stack that will be made available to you. Most of them are experts in remote work, and they’ve learned what works and what doesn’t when it comes to communicating and connecting with colleagues, managers, and clients.

If your company is new to the remote world, there will likely be a learning curve, but don’t be afraid to express your needs, pitch new software and tools, and test out those you think could help you stay productive while staying in touch. Project management tools like Asana or communication tools like Slack create a virtual team so you don’t feel like you’re in it alone.

Question #6: Do I Have to Say Goodbye to Workplace Culture?

Giving up an office is more than bidding farewell to your cubicle. It’s operating day-to-day without seeing your coworkers, chatting around the water cooler, or popping out for a long lunch. It’s no more awkward-but-sweet birthday celebrations. No more goofy team-building exercises. Giving up our traditional notions of employee culture can be bittersweet. But the right remote company will understand how valuable culture is to their distributed team, and will work to ensure it doesn’t take a backseat to business as usual. Video apps and communications tools still allow you to be in contact with your coworkers, and a good manager will know how to encourage conversations and build relationships that aren’t centered around work.

Question #7: What if I Hate it?

I’ll be real with you: there will be hard times. There will be days you don’t want to put on real pants, and days the commute from the kitchen to the second-floor home office feels like too much. And that’s okay. Just like any job, going fully remote comes with its own challenges and hardships. It’s how you respond to them that matters. Some days, it’s okay to leave your camera off for a meeting. Some days, it’s okay to work from the couch while a true crime documentary drones in the background. If those days start to outnumber the days when you make your deadlines, get your tasks crossed off and otherwise kill it, then there may be a problem. Here are some ways to troubleshoot before you decide the remote life isn’t for you:

  • Starting out, give yourself a trial period to adjust, and don’t give up before you’ve really started committing to a fully remote job. 
  • Establish a routine and stick to it. Set your alarm, then complete your morning ritual just as you would if you were going into the office. Take a shower, eat a good breakfast, squeeze in a workout; whatever you need to do to feel ready for the day ahead.
  • Stretch your remote wings. One of the best things about being able to work from anywhere is to actually work from anywhere. Plan a short getaway that gives you a new view, both literally and metaphorically. Remember, a midweek workcation wouldn’t have been possible in your traditional office job.
  • Identify what’s holding you back. Make a list of the pros and cons as you’ve experienced them. Which cons can you address and overcome? Which pros outweigh the negatives? 
  • Define your “why.” Do you want to be home more for your kids? Do you want to travel and see the world? Or do you simply want the freedom and flexibility that remote work offers? Think about your answer carefully, and once you have your top one or two “whys,” write them down and put them up where you can see them. Put a sticky note on the bathroom mirror, or print it out and hang it on the fridge. Repeat it to yourself like a mantra. When you remember your “why,” the “why not” won’t feel so overwhelming.

Question #8: What Do I Have to Lose?

With the growth and acceptance of remote work post-COVID, the risks you’re taking aren’t as big as they would have been five years ago. Remote work is more accepted, jobs are becoming easier to find, and the demand for skilled remote workers is growing. The more important question is: What do I have to lose if I don’t give this a shot? The answer to that is…a lot. You’ll miss out on opportunities to travel or on gaining experience in your career, on your terms. Flexibility to craft a life that suits your needs, feeds your spirit, or helps you gain insights into yourself that you wouldn’t otherwise have learned will go by the wayside. And doing great work the way you want to achieve the goals you desire may be left behind.

You have everything to gain by committing to a fully remote job. It won’t always be easy, but it will be an experience that will shape your career and your life, well into the future. Use these tips to ask yourself the tough questions to get you started, and good luck on the journey!

Author Bio

Jeanna Barrett

Jeanna Barrett is the Founder & Chief Marketing Expert for First Page, an award-winning, fully distributed growth marketing agency. Jeanna has a combined 17 years of inbound marketing experience at venture-backed startups, digital agencies, and Fortune 500 companies, with an expert focus on business and tech. She’s been named ‘Top 40 Under 40’ of brand marketers and ‘Best in the West’ for financial technology marketing. In 2016, Jeanna left the U.S. to lay roots and build her business in Belize, and in 2021 First Page was named #43 in the fastest-growing private companies of Inc. 5,000 Regionals: California.


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