What to Expect When You're Expecting to go Remote

San Francisco, California on a Friday in March

You’ve ordered an ergonomic chair, selected the coffee shop you’ll spend occasional afternoons at, and committed yourself fully to dressing each and every day. You’re ready for your new life as a remote employee. Right?

You will need to retune

If you’ve worked professionally for years in a typical office setup, recognize that your current behaviors and routines have been finely tuned around that environment to work well for you.

When you start working remotely, you’ll encounter a very new environment that you aren’t tuned to at all. The cat will scratch at the door while you’re on a call, you’ll find yourself in the kitchen for a snack more often than you’d like, you’ll jump online too soon after waking up.

When you compare remote work to office work, or consider how the transition is going, entertain that what you may be comparing is an untuned lifestyle to a tuned one. It’s going to take some time; patience will see you over the ridge.

You will miss the happy accidents

Some of your old routines may have had positive side-effects you never realized until they went away. Maybe your morning commute was a sacred rite that armed your mind for the challenges to come. Maybe the timing of your lunch yielded the perfect blood sugar levels for an effective hiring council.

Be thoughtful of these; recreate their ceremony. A walk to the park and back is a pleasant commute indeed.

Your entropy will decrease

Offices are a wonderful source of randomness (it may require some distance for you to admit it to yourself). No longer will you serendipitously take the elevator with a new hire and discover you love the same pop punk band. Put your mind against this task and find other ways to bring dice rolls back into the fold.

One trick: budget 30 minutes for a random 1:1 each week. Start with your best office pal. At the end ask, “who do you think I should chat with next?”. Take their suggestion as gospel.

Another: spontaneously ask people how they are. No agenda, and regularly. It’s cool to hate on chat apps in the workplace; don’t forget they’re still good for chat.

A final: shift your hours. Rituals executed between 7am and 3pm will have a different halo than between 9am and 5pm.

You won’t see the horizon

When you get to the office in the morning and walk to your desk, you collect an amazing volume of data. Alice and Bob are at the whiteboard arguing over modular arithmetic, or something. Something is deeply furrowing Seymour’s brow as he stoops over his email client. Lenny is unusually chipper sounding, a few rows over. Samantha has been putting in an awful lot of late nights…

A vibrant pastiche of emotional temperatures; a map you’ll use to navigate the choppy waters of the day.

But obfuscated to the remote soul. At your disposal is a chat application or the designed words of an email, betraying no dimension deeper than the bytes on the wire.

Know this blindness. Send waves and listen carefully for their reflection.

You will need to manufacture accountability

It will be too easy to peep the haps on twitter. You will self-justify: “part of my job is staying informed”. You will know this to be hogwash.

Seek an environment that will stimulate the embarrassment you’d feel if a coworker caught you e-shopping for winnie the pooh memorabilia.

The library perhaps. Live stream to your team on twitch while you groom the backlog.

Train this muscle. Overload it and recover. Reward good behavior liberally with treats.

You may see your partner a lot more

This is especially the case if you both work remotely. This is wonderful: we should spend gluttonous amounts of time with those we love.

Also wonderful (and healthy and natural): time apart. Identify what you like to do alone and prioritize it. Learn how to explain that to your partner with tenderness.

You will still loathe tough conversations

The necessity to have tough, private conversations will not go away. Instead of the smooth, “hey Carl can we grab a coffee this afternoon?”, you will have some clumsy meeting invite / video conference alternative.

This is not an excuse to shy away. Prove to yourself that you won’t slide into the easy default setting of passive malaise. Engage and participate. You will feel better and the work will show it.

Another good opportunity for positive reinforcement through treats.

You will need some easy wins

A lot of transitioning to remote is identifying and replacing all the behaviors and techniques you used in person to be productive.

Whiteboarding and coffee walks have their remote equivalents, but it’ll take you a little while to figure them out. The tuning we discussed earlier.

In the meantime, front-load your schedule with some tasks that are just as easy to accomplish remotely as they are in person, even if they’re not the most important: fix a bug, ship a modest feature, write a design doc.

Little snacks like this will help stave off some of the existential listlessness that decorates any transition.

You won’t understand things

Startups exist in a mire of ambiguity. Strategy, roadmaps, and projects can only be expressed in confidence intervals.

You alone in your quiet outpost may perceive the ambiguous, confused, or just poorly communicated with startling clarity. Perhaps it’s the lack of distraction—that balm for everything deeply unsettling but also true.

You will feel alone with this demon. It will stare back at you with abject stillness and infinite patience. It will be unpleasant.

But your dread is also your superpower. It is the instinct and motivation to be an opposing force, a beacon for your teammates drowning in distraction. This is your privilege and responsibility.

To create light you must engage and participate, generate productive friction, resist until your sensibilities are satisfied.

You will be inherently unavailable

You will effusively suggest otherwise, but it will remain the case. Welcome the steepening grade; you too will overcome this.

You will send emails, make announcements, letting people know you’re around if they need help or guidance and shiver noxiously at the implied self-aggrandizement. Few will take you up on it.

Be available in spite of it, when you have something to add. Lurk in chat rooms and contribute unprompted. Comment on code changes that aren’t assigned to you. Backoff if you get called out for overstepping, and silently congratulate yourself: you’re becoming present.

You will have an opportunity

Adaptation to a changing environment is as fundamental a process as life knows. In moving from the old to the new you’ll find a novel set of constraints against which to respond.

There is, after all, nothing special about the remote environment. It will just be a new stimulus, a vector towards growth and maturity, if you choose to see it that way.