Dear Businesslady: Remote Possibilities

Photo by Gerson Repreza on Unsplash.

Dear Businesslady,

I recently had a major career change that has been great for my life. One of the ways it’s better for me is that there are opportunities to work from multiple locations, including from home, which offers me some flexibility I didn’t have before. I have three small kids, so this is a very welcome change from before, when I basically spent all day locked inside a mountain.

The problem is, I have no idea how to be productive when I work from home. Do I work whenever the feeling strikes me? Do I drop the kids off at school/daycare first and then shower? Wake up early to shower before they go, like I would if I were going into an office? If I get stuck on something, do I let it go and go do a load of laundry, or will I just end up procrasti-cleaning my house and doing no work? What about grabbing coffee with a friend? In the mountain it was basically a butt-in-seat equation, so it didn’t matter as much, but I don’t want to be dishonest (or over-specific).

Basically, HELP.


Freed from the Mountain

Dear Freed,

In some ways, I’m uniquely well qualified to answer working-from-home questions because that’s been my life for more than five years now. But it took me a while to learn how to conduct myself as an offsite employee, and that’s made me aware of how idiosyncratic remote work routines can be (something I never thought about at all before it became part of my own reality). You hear “I’m working from home today” and it’s easy to imagine your colleague in some kind of technological either — a laptop and a chair in an otherwise empty void filled with those green lines of code from The Matrix. But in truth, they’re somewhere, and that somewhere is either enhancing their productivity or entirely undermining it.

Of course, people form their own noticeable, work-adjacent habits in traditional offices too. There’s the “make oatmeal in the breakroom” crew, the folks who never show up without their latte and bagel, the early risers who are always the first to arrive. And that’s just a small sampling of examples from the very beginning of the day.

Yet however successfully you manage to carve out your own little world in an office setting, you’re always beholden to the physical realities of the space and the the litany of human interactions happening within it. (“Work is other people,” you might say — and if you could use some help navigating the fraught interpersonal relationships in your office, I’d encourage you to sign up for this professional development workshop I’m doing in November. As always, it’s free, and you can attend remotely or in-person in Chicago.) Whatever feelings you might have toward your coworkers, you do have at least one concrete thing in common: you’ve all converged on the same location and (at least ostensibly) you’re all there to do your jobs. Both the space and the people act as subtle prompts to stay on task.

The social dynamics of the home office, by contrast, don’t have that unified sense of shared purpose. Instead, they’re defined by your domestic situation. If you’re lucky, your cohabiter(s) will leave you alone and keep things quiet (supportive partners, respectful roommates, well-behaved children and pets). If you’re not, you’ll have to find a way to eliminate or at least minimize inevitable interruptions — from clueless partners, boisterous roommates, children clamoring for your attention, and pets who are drawn to your lap and keyboard like magnets.

It’s worth remembering that “home” isn’t a monolithic category either. Ideally you want your own dedicated office — with a comfortable workstation, a door you can close, and (if there’s any chance you’ll ever need to conduct a Skype meeting) at least one wall that serves as a suitably professional backdrop. I realize that not everyone has the luxury of retreating to their private chambers, so if you’re short on space, find a way to work with what you have — and consider whether or not your setup is conducive to a long-term work-from-home arrangement. Similarly, consider whether or not your temperament is conducive to being a remote employee. It’s not for everyone, and that’s okay.

My most crucial advice for remote workers is this: be your own manager. With no onsite boss or colleagues, it’s on you to evaluate your to-do list, figure out your schedule, and keep yourself focused amid an entire household of potential distractions. If you’re like me, the little voice in your head will take care of this for you — my interior monologue is usually trying to convince me that I’m one poky email reply away from getting fired in spectacular fashion, regardless of how obviously untrue that is. (To be clear: it’s definitely not true.) While I may wish my own brain could be a little bit easier on me, it does ensure that I always prioritize my work over whatever else might be going on around me.

Everyone’s inner voice is different, though, and yours might be trying to sabotage you. “Turn on the TV,” it might say, “Let’s Make a Deal is on, and you love that show.” Don’t listen to it! Or at least, be suspicious of its seductive claims until you’re certain that a short break-time sojourn into the world of daytime television can fit seamlessly within a larger system of highly productive habits.

Your ideal work-from-home routine will depend on the nature of your job, the particularities of your environment, and your own personal proclivities. It also depends on a thousand little choices that you make in the course of each day. Over time they’ll aggregate into a set of established patterns, even as you need to remain ready to adapt to your job’s situational demands. On the one hand, you’re at home, and responding to your immediate surroundings. On the other, your mind needs to stay connected to your workplace, imagining the rhythms of your coworkers’ days and anticipating what they’ll need from you. Even if you “always” take a walk at 11 a.m., for instance, that’s not a great reason to force 15 other people to reschedule a conference call.

Given all the variables in play, there’s no single Right Way to Work From Home. Instead, I’ve taken all the options laid out in your letter and gone through them Pro and Con style, with a little blurb to summarize the best- and worst-case scenario for each.

Working whenever the feeling strikes you

Pros: Cons:
  • Triage tasks so that you can handle them most efficiently
  • Your availability and contributions are out of sync with what your local colleagues are doing
  • The feeling does strike you — often! You’re taking care of business before dawn and on into the night when necessary
  • Temptation to procrastinate until you really feel like working (which may be… never?)
  • Maximize your personal productivity by aligning your micro-breaks with your chores
  • Never know when you’re allowed to quit for the day
  • …and that’s where the “pros” end from your employer’s perspective, since any job will require you to work at times that are inconvenient to you
  • End up having to work long hours or through weekends because you haven’t budgeted your time properly
Sweet, I just sent six emails from the bathroom! Ugh, I worked through dinner and also bedtime.

Getting outside-world-ready first-thing in the morning

Pros: Cons:
  • Feel like you’re going to a “normal” job; don’t have to live in fear of surprise Skype calls
  • Delays the start of your workday — checking email in your PJs allows you to “get in early” (especially if you’re a time zone ahead)
  • Gives your brain time to wake up before you officially start working
  • Don’t get to enjoy the sublime comfort of being a schlub
  • Zero chance that a busy day will mean you’re still in pajamas with unbrushed teeth at 6 p.m.
  • Can’t use hygiene routines as opportunities to decompress/take breaks
Oh, yikes, it’s time to head to game night. Good thing I’m already dressed! All of my best work ideas happen in the shower… at like 2 p.m.

Doing laundry, procrasti-cleaning, and other domestic distractions

Pros: Cons:
  • Manual, intellectually undemanding tasks can help you puzzle through problems or get unstuck
  • Risk being in the middle of something/unavailable when colleagues need you
  • Folding clothes (etc.) allows you to actually listen during conference calls instead of focusing on your computer
  • May not feel mentally present or like you’re truly “at work”; could get distracted and miss emails or calls
  • Makes your day as productive as possible — domestically and professionally
  • Shockingly easy to piss away the day if you’re not careful
That meeting made me furious but then I cleaned all my grout and got over it. I don’t feel like writing… maybe I should reorganize my entire wardrobe. Wait, how is it already 4 p.m.?

Dipping out for coffee/errands or otherwise “leaving work” during business hours

Pros: Cons:
  • Freedom! Sweet, sweet freedom! (But once again, this is a perk for you, not necessarily your job, so be cautious.)
  • Miss a few calls and your coworkers will think you’re flighty. Which will be entirely justified.
  • Makes the most of your schedule flexibility — seeing parent friends while their kids are in school, avoiding rush hour while running errands, etc.
  • Might cause serious problems if you’re gone when a crisis emerges — and extra-ultra-serious problems if it happens more than once
  • Getting out and being around people reminds you that you’re not the last human being on Earth
  • Could make you feel irresponsible/less committed to work — or worse, might legitimately be a betrayal to your employer
Do you know how quiet the grocery store is in the middle of the day? Going after 5 p.m. is a literal fool’s errand. “You need those reports now? I’m …um …not at my desk. …I didn’t want to bother you about it but I’m kinda …at a baseball game? …Yes, I understand why you’re upset.”

That brings us to your last worry — about dishonesty versus excessive specificity — which requires a different treatment. While generally speaking my stance on dishonesty is to file it under “con,” the person you really need to be honest with is yourself. Especially in these early days when you’re trying to establish an effective routine, conduct regular self-evaluations: Are you available when your manager(s) and colleagues need you? Are you turning projects around quickly enough? Is whatever you’re producing up to an appropriately high standard? If you find yourself falling short on any of those metrics, you need to adjust accordingly.

Similarly, you need to be honest about your own work style — your proficiencies as well as your flaws. Recognize that you’re responsible for structuring your day in a way that makes you most productive. I’m weirdly adept at switching between disparate tasks and immediately giving them all of my focus, and that informs how I organize my time. But if you’re someone who needs to slowly settle in to things, don’t pretend that’s going to change when you’re working remotely.

Traditional in-office jobs have a certain degree of built-in accountability: your manager may not know exactly how much you’re doing while you’re sitting at your desk, but they at least can see that you’re there (or notice if you seem to be away for inexplicably long stretches of time). Plus the panopticon of a shared workspace means you’ll probably start feeling self-conscious if your “quick dip into Twitter” turns into a 45-minute meme-creation project.

At home, no one can see you slack off, but you’ll know if you’re falling behind… at least eventually. That realization (whenever it hits) will come packaged with unpleasant side effects like guilt and heightened stress, so do yourself a favor and prevent it from happening. You’re still developing your instinct for what your workday should feel like, so err on the side of completing assignments extra-fast, doing additional proofs on everything, and responding promptly to emails and calls. Going above and beyond isn’t indefinitely sustainable, but it will ensure that you don’t let your newfound freedom interfere with your work. That — coupled with ongoing, active contact with your colleagues and especially your boss — will help you make sure you’re not being too casual with your work time.

As I got accustomed to being remote, I realized that I was way overcorrecting, to the point where I was working far harder than anyone expected me to. That’s its own problem (with its own solutions) but ultimately it’s a good problem to have! You can always dial back, but if you start out by blowing off work then you may not get the chance to redeem yourself.

I don’t say this to scare you — except insofar as a little bit of fear will keep you honest and on-task. Discipline and a sense of personal responsibility will be your biggest assets while working offsite. But as long as you’re meeting your goals, then the specific structure of your workday is immaterial. Likewise, falling behind is something that can happen just as easily if you’re plopped in a cubicle for nine-plus hours a day. The evergreen hallmarks of a healthy professional environment — clearly communicated objectives, regular check-ins, and forthright, actionable feedback — will help you calibrate your work-from-home practice as it evolves and make whatever corrections are necessary to keep you in management’s good graces.

In the meantime, you can revel in the comfort of wearing exactly what you want, commuting for zero hours per day, and exercising complete control over your environment (at least as far as your domestic compatriots will allow). If you can make it work, it’s a pretty sweet gig.

Got your own magic formula for being a remote employee? Let me know in the comments!

Courtney C.W. Guerra is an editor and writer who started giving advice as Dear Businesslady on The Toast in 2014. She’s the author of Is This Working?, a career guide that she personally guarantees is at least as funny and entertaining as one of her columns. Keep in touch via Twitter, Facebook, her TinyLetter, or her website.

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