Probably the most curious thing about our jobs is the work-from-home aspect. Most of us have become experts at fielding the question "But what do you do all day?" At the risk of sounding caustic... we work.

According to the Gallup Poll's 2017 State of the American Workplace report, 37% of employees would switch jobs "in order to have the ability to work where they want at least part of the time". The same poll data shows that 43% of workers already do work remotely at least some of the time (up from 39% in 2012). The poll data suggests that not only are more workers diving into remote opportunities, but also those who do are working remotely for an increased percentage of time. Between 2012 and 2017, the number of workers spending 80% or more of their time remotely increased by 7 percentage points. Given remote work is both more available and more accepted these days, we thought we'd share some things we've learned from our remote experiences – and wish someone had told us.

Know Thyself

It’s easy to boil this down to personality tests and whether or not you’re an introvert, but you should seriously consider what you want out of your work life and how much you need human interaction before diving into remote work.

“This kind of work is not for everyone. It's hard to be self-regulating in any work environment and when you know that you don't have a boss who might pop into your cubicle at any time, that means you need to have internal regulation instead of external.” Adam T, Customer Success

The reality is that working remotely probably isn’t a great idea for everyone. How are you on distractions? Do you know how to help yourself focus? Or what hours of the day you work best? (And I do mean actually work, not just your preferred hours around things you’d rather be doing.) Are you organized? Self-driven? Motivated?

Before you make the dive, think seriously about how well you know yourself. Examine especially your preferred style of communication, whether you need a certain amount of face time to be happy, and whether you need anything in particular in order to stay focused.

Actually, think about those things anyway: they’ll help you no matter where you end up.

Time Management

As remote workers, we tend to field a lot of questions about time management, tracking hours, and how we prove we’re working. Admittedly, there is less oversight when you’re working remotely, and it can be easier to slack off.

“The part I don't usually tell people is how hard it is to self-motivate and to keep the distractions at bay. When you don't feel like doing your job, it is very easy to not do it.” Chip B, Engineering

However, if the deliverables don’t appear, it will quickly become clear to everyone – including you – that you’re not pulling your weight. We track the majority of our work through tickets and estimate in advance. That helps keep you honest if you’re having a hard time doing it on your own. If you're really struggling, you can also submit daily or weekly reports to help out as you adjust.

Many of us have exactly the opposite problem:

"I think for me, it was actually a little tough to relax for the first six months, because I felt like I had to work ALL THE TIME to show PROGRESS and that I DESERVED my remote privileges." Beth S, Customer Success

If you find you're more likely to work overtime, remember to set yourself strict office hours. With any luck you’ll have a team that holds you accountable for this but if not, you need to regulate yourself. I found myself working very late when I first started because my office was in my living room; if I didn’t have plans any given night, what really was the harm in turning my laptop back on? Allow me to metaphorically slap past-me's hand. The harm is to yourself and your work/life balance. If that isn't sufficient deterrent for you, think about the harm to your social life, loved ones, or even the company you work for. You aren’t helping anyone if you burn out.

“I have an office that I can just shut the door to, both to keep the family out and to keep myself out when it's time to be off work.” Adam T, Customer Success

For most people, the main challenge is focus. You need to structure your day in a way that gives you time to dive in. Maybe you need 2 hours of uninterrupted work each day, or 4. If you move into management roles, in some ways things simplify because the job pulls you in multiple directions at once. In a way, that makes finding tasks simpler. If you're good at saying no and keeping many plates spinning at once, you should do pretty well.


No one but you is in charge of your office environment when you’re fully remote, so know what you need to thrive. For example, I can’t work in my PJs. I simply don’t feel focused if I don’t take the time to get ready for the day, but I have it on good authority that several co-workers can’t get comfortable if they’re in a button-down and it actually impacts their ability to get in the zone.

It’s worth investing in your desk. I can’t stand sitting all day and am far happier with a standing desk attachment. I’ve known people who feel trapped if they work from a desk at all. Consider carefully whether you really want your gaming rig set up just to the left of your work laptop. Just for fun, you can see some SpiderOaker desk setups below.


If working from a co-work space or a coffee shop is an option for you, great! Keep in mind what kind of work you’re doing on any given day and whether it’s conducive to a change of scenery. Several of us use location changes to snap us out of ruts, while others have found that they cannot get a single thing done at a coffee shop.

“I call it my 'dynamic work environment', the fact that I can work from anywhere. My motivation can just stagnate going into the same office every day, week after week. Being able to work remotely from anywhere –; home, coffee shop, someplace new –; helps me to stay interested and actually more focused.” Courtney D, Marketing

Privacy, PLEASE

Roommates and family can be complications to remote work. How do you explain to someone else that your physical presence does NOT necessarily entail your mental presence?

“I think family has a really hard time understanding what it means to work from home; just because you can see me doesn't necessarily mean I am available to talk or answer your questions.” Jeremy H, Customer Success

Setting office hours, having a specific office, and creating an effective ambient environment (invest in good headphones) are all useful aids.

“What I wish had known before working remotely that it would feel better to live in an apartment complex that has some community spaces. Or really that when you are 100% remote it's really helpful to have a separate space to work in. I can't tell you how many times I've taken a call in the bathroom because it's the only door in our apartment.” Carissa G, Design

Several of us have kids and structure our day around school drop offs and pickups. If you plan for it, it’s less a distraction and more a helpful break in your day. Remote work lets you structure your day around kid things, but you need to be very careful to make sure to build your schedule in a way that gives you enough time to focus and do deep-dives as well. Remember that school breaks will throw off your carefully balanced schedule.

“Summer vacation is a whole different thing. I used to get up and start work at 4:30 or 5 am so I could get in at least 3-4 solid hours of work before [the kids] got up.” Adam T, Customer Success


At SpiderOak, we’ve found that regular meetings help us stay up to date. Our squads meet once a week, and some departments meet more frequently. Popup calls are always an option. Every project has a Confluence space and if at all possible documents are read-accessible by all employees. We also chat via Semaphor which allows us to carry out ongoing, transparent conversations with more ease than an email thread. Another way we try to stay on the same page is through clearly communicated shared goals.

Working remotely requires you to be explicit about everything. Assumptions are never your friend, but the problem is exacerbated in a remote environment. You simply do not have the luxury of walking by someone’s cubicle and hearing them mention a project you didn’t realize they were working on. You aren’t going to be able to look over someone’s shoulder and make sure you’re looking at the same screen as them. The only tool you have is to talk directly to people. On the bonus side, most of your communication will be comparatively asynchronous so if you’re hot-tempered you get a chance to think through what you’re saying before you click “send”.

I personally think the best thing you can do is to make communication expectations crystal clear. (I like this example from Doist.) Via which channels do you expect to receive communication? With what frequency? Are there any ingrained, unwritten rules for how you communicate? For example, is there a time and a place for questions, and a time and a place for quiet?

“Contact with co-workers is more limited, but it's paradoxically even more important because of the difficulty. You have to be proactive about talking to people and correcting misconceptions. Being a good communicator isn't desirable here –; it's required.” Chip B, Engineering


If your favorite spot at your office is the proverbial water cooler, you may want to think twice about a fully remote job. Even if you choose to work out of coffee shops and cowork spaces, there’s a degree of isolation from your coworkers. You certainly won’t be raising morale over inter-office softball games. We’ve found a few effective ways to combat this, but even so we have occasionally lost excellent workers because they realized they needed a more social environment to be happy.

"One thing that really helped me feel integrated and part of a team was my first meetup. There's nothing like meeting in person the people you work with.” Warren P, Quality Assurance

Meetups are game changers, especially if you can schedule them to coincide with onboarding, which takes longer when done remotely. You can’t just turn to the person next to you for help. Having at least a couple familiar faces to match to the nicks in your company chat aids in teaming, psychological safety, and general comfort with pinging someone with a request. We do find that every meetup results in a slow-down in daily output during the meetup itself – probably at least partly due to finally having an outlet for repressed social needs. If you plan for that, it’s well worth the temporary hit to productivity. We find that the heightened information exchange that happens during in-person meetups translates into a flurry of activity when everyone gets back home.

“A reccurring phenomenon for meetups is that work grinds to a standstill during the meetup but explodes afterwards.” Chip B, Engineering

If you can’t do meetups for some reason, screenshares, video calls, and regular meetings go a long way towards increasing the quality of communication, too. We have some channels in our company Semaphor team that are purely social; book recommendations, recipes, and hobbies are a great way to gain confidence reaching out to your colleagues. When writing this article, I received feedback that Pets of SpiderOak is our best channel and warrants its place on this list.


“I think remote work also shows that the company trusts its employees. We all tend to give each other the benefit of the doubt even if someone takes a bit longer to respond or if something falls through the cracks, and people jump in to help out. We trust each other because we all know what it's like to work remotely.” Courtney D, Marketing

One of our most frequently asked questions is whether remote work is as great as it seems. Despite all the warnings, if you know yourself well enough to self-mitigate any habits that will get in your way, there are a lot of perks.

“I think one major perk about working from home is being able to pick up my home deliveries from my front door.” Amber T, Quality Assurance

You’re always around for deliveries (maybe don’t tell your neighbors unless you want to run the risk of being around for their deliveries, too), the laundry is pretty much always done, you can set up your office exactly the way you like it, you can build your schedule around being a taxi service for your kids, and you can bring your laptop to the in-laws’ for a built-in escape. Perhaps best of all, your auditory environment is up to you. (We have several people on staff who favor obnoxiously loud keyboards that might be insufferable in a shared office!)

“My favorite thing about working remotely is my diet is much improved; I have a fully stocked, fully-functioning kitchen that I can use effectively.” Beth S, Customer Success

So if that seems great to you… we’d have to agree.

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