Should You Take A Remote Job?

Remote work is amazing, but it’s not for everyone. Is it for you?

Photo credit: Andrew Neel, via Unsplash

Recently, a friend of mine had the opportunity to take a job at a remote company. He’d never worked remotely before and wondered whether he’d enjoy it.

I get this question a lot: Should I consider working remotely full time? While it’s a great fit for me, it’s certainly not a great fit for everyone.

Another friend decided to move to a new city to be closer to his family. The company he worked for was remote friendly, so he kept the same position but worked remotely. He didn’t have a lot of friends in that city, and injured himself in the first few months, leaving him without the ability to freely walk around for a while.

“Brutal,” is how he describes his remote working experience. He moved back to work in the office within the year.

So how do you know whether remote work would be a good fit for you? I would divide this decision into three categories: You, The Opportunity, and Your Ideal Life.

You

Let’s talk about you. Are you a self starter? Are you independent, confident, and motivated at work? Do you hate micro management and thrive in ambiguous situations? Are you into using digital tools?

Where do you get your energy and motivation from? Are you a people person who loves collaborating in person because of the energy that’s generated in small groups? Look back at your friends over the years: Are most of them people you met at work?

Do you have hobbies outside of work? Do you get a lot of energy from pursuing those hobbies? Do you wish you had more time to pursue them?

Controversial bit: Do you have kids or aging parents? Do you consider commuting a drain on your time and energy…time you can much better by managing other priorities in the home (taking care of dependents, making food, shepherding kids around). Do you feel stressed by never having enough time or energy to properly manage your time because of physical constraints?

I think you know where I’m going here. The most important part of making the decision to go remote can be taken from Shakespeare. In Act 1, Scene III of the famous play, Hamlet, Polonius says:

This above all: to thine own self be true

In the context of remote work, I think about this literally all the time. Making the choice to go remote has to be a personal decision to be successful. It has to be based on introspection and self awareness. It can’t be solely based on outside pressure, family needs, or career aspirations. If you’re going remote because a spouse is moving to another city and it’s better for the family, but you are a super social person who gets energy from being around other people: You will likely be miserable in the long term. Of course, as long as you have self awareness, there are ways to counteract the loneliness, but it will have to come from you and not be structural. Now let’s move on to the actual remote working opportunity.

The Opportunity

You’ve found your dream job but it’s at a company that’s all distributed workers. You’ve never worked remotely before, should you do it?

You’ve found your dream job, but it’s a company where you’ll be joining a team as the only remote employee. Should you do it?

You’ve decided to make the leap and become your own boss. You’ll be doing (insert type of work here) on a contract basis with clients, and mostly working remotely. Should you do it?

Now let’s say that you’ve done your homework with the first step and have done a lot of introspection about the work situations in which you thrive. It’s time to evaluate the actual opportunity. There are many other questions about remote work that you need to take into account.

1. Has the company invested in or have a commitment to remote work from a structural standpoint? Great remote work doesn’t just happen. You can take a look at amazing remote friendly companies like Zapier, Buffer and Trello (sorry I’m biased!) to see how thoughtful they have been about remote work. Just like you wouldn’t show up to an empty office without chairs or desks, there has to be a commitment to setting up the infrastructure for work. For remote work, this may consist of a stipend to set up a home office, regular face to face offsites for teambuilding, or even a coworking allowance. I would ask for remote work handbooks that are specific to the company to see how much time and effort has been spent really thinking about how to optimize for remote work. One great way to really dig into a new company’s remote working structure is to see how new hires are handled. Do they just start on day one with a computer at home, or are they flown somewhere to meet their team in person? Is there a remote specific onboarding process? You get the idea (and I’ll be writing a LOT more about remote specific interviewing, hiring and onboarding processes from a management standpoint if that’s something readers are interested in…let me know!)
2. Does the company have remote first/friendly culture? Some examples of remote friendly culture are weekly remote get togethers, monthly Town Halls that are done through Zoom, and tooling that promotes people bringing their whole selves to work. For example, Zapier makes copious use of Slackbot to ask team members questions about their weekends and hobbies to encourage dialogues. Does the team get together for regular face time? One thing you’ll learn quickly about remote work is that face time is still super important, even though you just have to plan for it and use it more strategically. Lastly, an easy way to dig into remote culture is to see how often the company talks about it. Companies that commit to remote work are often thought leaders in this nascent space, whether it’s the CEO regularly being quoted in articles about remote work or how often remote work is featured on a jobs page.
3. Is everyone remote? Are you the only remote person on a team? I’ve done a ton of public speaking about remote work and invariably, the most common question I get at the end of any talk goes something like this:

“Recently, I went remote and the rest of my team is still in the office. It really sucks because I feel left out of a bunch of stuff and team members are starting to resent me. What should I do? Can this work?”

My answer is: No it will not work. Being the only remote person on a team where everyone else is in the office is a recipe for disaster. Situations like this also perpetuate the assumption that “We tried remote work, and it didn’t work.” The issue here is that all workers don’t have the same context. When everyone is in the office, people can see and hear the norms and expectations around them. People can have hallways conversations and not think twice because that’s the culture. As soon as that changes for anyone on the team, a feeling of inequity develops. Also, because everyone is human and the grass is always greener on the other side, the in office people will envy the remote person their flexibility and lack of commute and the remote person will envy the in office people for their social connections and free snacks. FOMO develops on all sides. Again, we’re all human.

So if you’re looking at a remote working opportunity, make sure to find out what kind of team you’ll be joining. An experienced manager will almost never hire someone remotely when the rest of the team is in an office.

This is not remote work. I repeat, this is not remote work. Photo credit: Dan Gold, via Unsplash.

Your Ideal Life

When I was a bright eyed college graduate, I picked up the book The Four Hour Workweek and was amazed by the contents. You could design your own lifestyle? WHAT? My peers were all working 80 hours a week at consulting and investment banking jobs knowing for sure they’d be successful (this was before “burnout” was a thing). Here was a guy telling me I could live on an island and pursue my passions all while igniting my career?

Well obviously, that’s not true for everyone, but the basic idea of designing your life to fit your ideal lifestyle stayed with me throughout my career. After a few years of working in offices and seeing how much time is wasted, I knew there was a better way.

What’s your ideal lifestyle? Now I’m asking you to be realistic here and not tell me that you just want to hang out on a beach and drink Mai-Tais all day. If you’re anything like me or my husband, that life would bore you in about a day.

So close your eyes and imagine a typical day in your ideal life: What are you doing when you wake up? What kind of desk (if any!) do you have? Are you hanging out with coworkers or are you making friends playing intramural soccer? Are you able to coach your kid’s soccer team?

Make sure whatever job you take is one that fits your introspection, is structurally set up for success, and gets you as close to your (realistic!) lifestyle as possible. This framework isn’t really specific to remote work or considering a remote job: it’s a recipe for analyzing an opportunity based on what will make you happy.