Four questions to ask yourself before you take the plunge

Choosing to work remotely could be the best career decision you make this year. Alternatively, you might make the move to remote work, only to wonder why you thought it was a good idea. The difference between these two paths has less to do with the type of work that you do, and more to do with the type of person that you are. Here are somethings to think about to help you decide if remote work makes sense for you.
Do You Have a Compelling ‘Why’?
There are a great many professional and personal reasons to love remote work. Many successful remote workers enjoy flexible schedules, increased work autonomy, and the opportunity to pursue outside interests. Like any job, however, this set up comes with it’s own stresses. For some, remote work is incredibly isolating. Others fight an ongoing battle to keep friends and family members from interrupting their work day.
In those difficult moments it helps to remind yourself of what you get out of remote work. Does your virtual job allow you to live in a less expensive part of the world? Can you continue to work while caring for a young or ailing family member? Perhaps you are a military spouse who moves every two years. Working remotely may allow you to stay with the same company no matter where you go.
Keeping your ‘why’ in mind will help you in at least three ways. First, it can help you endure whatever is irritating you. Your spouse might have a poor sense of what ‘do not disturb’ means, for example, but at least you get to spend more time with your kids. Your coworkers may forget that you work in a different time zone and try to message you at 6 am, but at least you can train for half marathons. Take a moment to make sure you’re clear about the benefits that remote work brings to your life.
Understanding your ‘why’ also helps you to know when it’s time to cut your losses. Your circumstances may change, and your ‘why’ may no longer apply. If you took a remote job so you could homestead in rural Canada, and discover that you hate homesteading, there may be no overriding reason to stick with remote work.
The quality or urgency of your ‘why’ will also determine how much effort you ought to expend to become an excellent, contented remote worker. The person who has to choose between working remotely or not working at all will be more motivated to excel in this environment than the person who can get a traditional office job at any time. Know where you fall on this spectrum.
This leads to another question that you should ask yourself.
Are You Willing to Adapt?

Think back to your first “real job.” For most of us, that job took place in some sort of in-person setting. Even if you didn’t particularly like that job, or the ones that followed, you learned how to navigate your environment. You learned how to look busy and productive, how to make work friends, and how to navigate office politics. You probably learned how to turn work off (even if you still have trouble actually doing so).
Switching to remote work means learning new approaches to these activities. Your boss can’t see you industriously typing away at your computer. It takes effort to figure out that your colleague loves the same movies you do. You CAN make work friends, grow in your career, and learn to turn off your remote job — but you have to be willing to learn. Are you willing to learn? Do you have the bandwidth to try new things, fail, and try again?
It’s important to be honest about your willingness to adapt. Some people really want to work in a traditional office. They may take a remote job for a short time in order to pay the bills, but would not consider such a job a long-term commitment. If this describes your situation, understand that you will still need to learn some remote skills if you wish to keep your remote job until the next in-person job comes along.
Are You Willing to Act?
All of us have a list of things we “should” be doing. I, for example, should have cleaned out and organized my kitchen pantry weeks ago. Fortunately this doesn’t affect anyone but me (and occasionally my spouse when the dried fruit packets avalanche on him, but I digress).
Are you the sort of person who gets your important things done? Your commitment to delivering quality work on time has to be stronger than your commitment to Netflix. No one is watching you. Remote work offers the unparalleled opportunity to dive deep into your task list if you are the sort of person who knows how to focus. If you can’t focus without the threat of a boss walking by or the social pressure of in-person colleagues, this may not be the right work setting for you. If you can self-regulate, then you may never willingly set foot in a traditional office again.
Incidentally, your future remote boss will also want to know the answer to this question. If you haven’t worked remotely before, think about other times when you had a commitment to fulfill with very little oversight. If you are a recent college grad, how disciplined were you in following a study schedule? If you’ve ever stared a side business, or tried to learn a new language or musical instrument, how hard was it to do the things you knew you had to do to succeed? Your answers to these questions can help you figure out how self-directed you are.
Are You Willing to Play?

Most people understand that they need to learn to focus on their work during work hours. What comes as a surprise to many remote workers is the need to focus on doing fun things after work. We all need a certain amount of human contact. A successful remote worker not only knows how much contact she needs, she takes steps to hit her weekly quota. That may mean enrolling in dance classes, going to church, or joining your local knitting group. Be the sort of person who can pick something and then actually do it.
Success as a remote worker won’t come from using the latest team building software, or learning a new skill — though both of those things can enhance your career. To really make it as a remote worker, you need a clear sense of why this lifestyle works for you, a willingness to learn new things, and the ability to have some fun along the way. Armed with these qualities, you can roll with whatever your remote work/life throws at you.