The Remote Employee Handbook
I’m one of the 15% of U.S. workers who are fully remote. As a software engineer, anywhere with a decent internet connection becomes my office, and I’ve tested that theory in quite a few places. I joined Jellyfish in May 2020, right as the COVID-19 pandemic sent the American workforce indoors. Our company adapted to remote work quickly, and five years later, we still don’t require anyone to go into an office. (Though for the record, there is one, in Boston’s financial district at 225 Franklin; very shiny!)
Since joining, I’ve lived in and worked remotely from Boston, Champaign, IL, and now the upper boroughs of New York City. Whether from my apartment, a train, or a coffee shop with questionably stable Wi-Fi, I’ve been able to contribute meaningfully to our codebase, and more importantly, collect a lot of opinions about remote work. My overall philosophy is pretty simple: remote work is awesome. The freedom and flexibility are unmatched. But! It’s not all sunshine and sweatpants. There are frustrations, distractions, and the occasional existential spiral (sometimes all before lunch). Over the years, I’ve built a few habits, tools, and survival rituals that help keep me productive, sane, and, most importantly, socially acceptable.
If you're a fellow remote worker looking for tips, or you're just trying to figure out what this whole laptop-on-the-couch lifestyle is about, you've come to the right place. Let's get right into it.
Chapter 1: Where to Work (and Not Work)
As a remote employee, the best place to work is wherever you can maximize three key qualities: functionality, comfort, and practicality. I’ll break each of these down briefly, but the main takeaway is simple: find what works for you.
Functionality refers to the bare essentials of a productive remote work setup, the non-negotiables. You need reliable Wi-Fi, easy access to power, and, yes, a bathroom that doesn’t require you to buy a muffin just to use it. I’ve lost more Zoom calls than I’d like to admit to sketchy café internet, and I’ve cut plenty of promising work sessions short after realizing the only outlet in the building was already taken by someone’s dying MacBook. If the core ingredients aren’t there, the work can’t happen.
Scoping out functionality is all about viability. Where you work on any given day has to support the type of work you need to do. Personally, I’m the kind of person who can drop into a coffee shop, throw on headphones, and lock in for a few hours. That works for me in NYC, where cafes are everywhere and walking to a new one is easier than restarting a router. But not everyone thrives in ambient noise and borrowed space. If you’re raising a family, need consistent quiet, or just value control over your setup, working from home might be the clear winner. Coffee shops and third spaces are great for breaking monotony or getting a change of scene, but when it comes to reliability, consistency, and full control, there’s still no place like home.
Next, comfort and focus are essential to how you’ll feel while working on any given day. This is all about sustainability; can you actually work here for more than an hour without regretting everything? This means finding a place with lots of space to sit, reasonably soft noise levels (although AirPods + Zoom are pretty effective at noise cancelling), and overall call-friendliness. Remember, just because you have work to do, that doesn’t mean everyone else around you needs to know about it. Be respectful of any space that you decide to work in, and the space will respect you back.
Finally, we have practicality: is the space convenient? Do you have to hike 30 minutes to get there, or is it right around the corner? Do you feel welcome, or are you constantly being side-eyed by a barista who knows you only ordered a drip coffee an hour ago? Is there backup seating if your usual window spot is taken? If the vibe check fails, it's probably not going to be a very good place to do work.
The perfect work environment checks all three boxes: functional, comfortable, and practical. But two out of three isn’t bad either. It’s all about balance and recognizing your constraints.
Chapter 2: The Rituals That Keep You Sane
One of the strangest parts of remote work is how invisible the lines become. When you don’t physically leave your home to go to an office, there’s no obvious moment when the workday begins, and no clear sign that it’s over. It’s just... you, and the internet, and that familiar glow of your screen. Over time, that blur between "living at work" and "working from home" can start to mess with your head, which is why I rely on rituals and personal systems. Not rigid routines, but gentle signals that help me shift gears and stay tethered to something resembling structure.
My mornings are intentionally unambitious. I’m not someone who wakes up at 5am to run a 10K and cold plunge into purpose. But I do need a soft runway into the day. That usually means making coffee, stretching a bit, and checking my calendar before I open any messages. It’s less about discipline and more about intention; a way of saying “okay, now we’re transitioning from human mode to work mode.” If I skip that little window of preparation, I feel it. I rush into tasks, get reactive, and end up chasing my day instead of leading it. There’s something surprisingly powerful about those quiet first ten minutes: no Slack, no email, and no cognitive overload. Just coffee, sunlight (when it exists), and the space to arrive at the day on my own terms.
Once I’m in the flow, I try to stay there, but I’ve learned the hard way that momentum has a shelf life. Around midday, I hit what I can only describe as the gray zone, where I’m still working but not really thriving. That’s when I know it’s time to unplug for a bit. I’ll take a walk, throw on a podcast, grab a snack that didn’t come out of a wrapper, or just sit quietly away from screens. These mid-shift pauses aren’t indulgent; they’re maintenance. Stepping away resets my brain, gives my eyes a break, and lets me return with a little more focus and a little less simmering dread. And look, some days I absolutely forget to do this and spiral into the 2pm scroll of doom. But I’m always better when I remember to walk away for a bit, even if it’s just around the block or to the roof.
Evenings are where things get trickiest. Without a commute or some external "clocking out" moment, it’s incredibly easy to just keep going. One more message. One more pull request. One more tab. I’ve had evenings where I meant to close my laptop at six and somehow looked up and it was nine. So I’ve learned to manufacture my own end-of-day ritual. I close open tabs, write down a few notes for tomorrow, shut the laptop with actual finality, and then I leave the room. Even a tiny shift in physical space helps. Some days I change clothes, go for a short walk, or just move to the couch with a book. I’ll often suggest happy hour plans with my friends for right around 6:00pm, forcing myself to stop working by 5 so I have time to get ready. The key is breaking that feedback loop of “still sitting in the same chair, still kind of working.”
And yes, we need to talk about clothes. The great “soft pants” dilemma. I fully get the appeal of staying in PJs all day: you’re home, you’re comfy, who cares? Over time, I’ve found that getting dressed (even a little) makes a subtle but real difference. (I’m also the type of person who would wear a button-down shirt during high school and college exams.) It’s less about professionalism and more about mindset. When I wear real clothes, I carry myself a little differently. I feel more like someone who’s here to do work, not someone who accidentally opened their laptop while watching Netflix. Plus, the occasional surprise video call has taught me the value of being at least 60% camera-ready at all times.
Ultimately, these rituals are personal. Yours don’t need to look like mine. But they do need to exist. Remote work, for all its freedom, can quietly dismantle the rhythms of your day if you don’t build some scaffolding to hold them up. The goal isn’t perfection. It’s presence. It’s drawing soft lines in a soft environment so you can move through the day with some sense of direction. And on the days when everything clicks, when the coffee’s good, when the walk helps, when the laptop actually closes on time, it feels less like you’re just surviving remote work and more like you’re designing a life that works for you.
Chapter 3: Tools of the Trade
Working remotely strips away the office scaffolding and leaves you with a simple truth: your tools are your environment now. They’re your desk, your conference room, your whiteboard, your headphones that cancel out the guy practicing saxophone outside your window. Over time, I’ve refined my setup to reduce friction. If something makes the day feel smoother, more focused, or just a little less annoying, I’m keeping it.
Hardware-wise, the basics matter more than you'd think. A good external keyboard and mouse combo is clutch for posture and comfort, especially on those days when a single task becomes a multi-hour problem. A laptop stand that brings my screen to eye level? Essential, and my neck thanks me for it. And noise-canceling headphones/earbuds are less of a luxury and more of a survival tool. I use them almost every day, whether I’m on Zoom or just trying to stay focused while the neighbor’s dog launches its afternoon bark-a-thon. As for monitors, I’m a big believer in the vertical second screen. Mine lives in portrait mode and is dedicated entirely to Slack. That way I get a longer view into channel conversations, can catch up quickly without losing context, and keep tabs on what needs my attention without toggling constantly. I’ve found that this helps me to stay grounded in the flow of communication without letting it derail my day.
For staying focused, I rely more on environment shaping than timers. I’ll block out “focus time” directly on my Google Calendar, which signals to my team and me that I’ll be heads-down for a while. This gives structure to otherwise unstructured days and helps fend off the temptation to context-switch every ten minutes. I’ve found that focus is about proactively designing space where attention feels like the path of least resistance.
Slack, Zoom, and Google Calendar form the backbone of communication and scheduling. I’ve come to treat my calendar less like a meeting scheduler and more like a boundary-setting device. I’ll mark when I’m deep working, when I’m open for quick chats, and when I need a break. It’s part workflow, part self-preservation. And with Slack always visible on that vertical monitor, I can scan channels and DMs without diving into the mental quicksand of switching tabs and forgetting what I was doing in the first place.
Then there are the extras, the “small but mighty” layer of tools that help remote life go smoothly. I have a solid hotspot plan as a WiFi fallback (thank you, Dad!) and a portable charger that lives in my bag just in case I decide to head out for a working afternoon. I keep a USB-C hub close by and a notebook for moments when digital feels like overkill. None of it’s glamorous, but all of it’s battle-tested.
Remote work forces you to find what keeps you focused, connected, and upright in your chair for more than an hour at a time. The best tools are the ones that fade into the background and let you get to the real work. And when that’s happening, it’s easy to forget you’re not in an office. You’re just working, fully immersed in it. Which, to me, is the goal.
Chapter 4: The Social Side
Remote work is quiet in ways that sneak up on you. You start the day with good intentions of heads down work, and by the time you look up, it’s late afternoon and the only human interaction you’ve had is a Slack emoji reaction and the voice in your head asking if it’s too early to make dinner. At first, the solitude can feel like a gift. No office chatter, no awkward small talk by the coffee machine. But over time, that isolation becomes a little too efficient. You suddenly feel like you’re slowly drifting into your own orbit. What now?
That’s why I’ve had to be deliberate about staying connected, not just to coworkers, but to the idea of a work community at all. Last spring, a coworker and I started working out of a WeWork in Chinatown once a week. It began as a logistical experiment. We have all-hands meetings on Thursdays, and we figured, why not be in the same room for them? But over time, it became something more intentional: a standing ritual, a shared space, and ultimately, a pilot for a policy that reimburses city employees for using remote office spaces. It was a way of giving people in NYC a consistent option to gather, collaborate, and feel less like they were working in silos. Those WeWork days have become a core part of my week: a chance to reconnect, reset, and actually feel like part of a team in three dimensions.
But it’s not just the co-working spaces that make remote life feel more social, it’s the tiny routines that anchor you to your surroundings. I’ve become a regular at a local coffee shop, and I can’t overstate how meaningful that’s been. The baristas know my order. I see familiar faces in the same seats each week. There’s a subtle but powerful sense of belonging that comes from being known, even a little, by the people around you. These small connections, a nod, a smile, the occasional “same time next week?”, create a rhythm that makes me feel more rooted in the city I live in. It’s social infrastructure in disguise, and it’s invaluable. (I touched on this topic a lot in my last post, which you can read here.)
Inside the virtual workspace, I’ve learned that connection takes intention. I make time for one-on-one chats with coworkers, even when there’s no agenda. I jump into the Slack channels that aren’t directly tied to work: music recs, weekend plans, the ever-essential pet pics thread. These spaces are where the remote company culture resides in the absence of the office as the “town hall”. When you see someone’s cat in a bowtie or find out they also listen to the same obscure synthwave playlist, you build the kind of rapport that makes collaboration easier, faster, and way more enjoyable.
Outside of work, I keep an eye out for meetups, low-key tech events, or just opportunities to co-work with friends for a few hours. Sometimes I don’t even need to talk to anyone, I just want to sit next to other humans doing the same thing I’m doing. That quiet camaraderie, the shared focus in a space that buzzes with intention, can be surprisingly energizing. What I’ve come to appreciate is that remote work doesn’t have to mean isolated work. You might have to work on these routines a little, but the upside? You get to build a social setup that actually fits your personality, your energy levels, your rhythms. Redesign your social life around what actually works. And when it clicks, it’s hard to imagine going back to the old way of doing things.
Chapter 5: Productivity (Or Something Like It)
One of the hardest parts of remote work, especially early on, is figuring out where the workday really begins (or ends), and how to define a “productive day” without the usual office scaffolding. It’s easy to mistake presence for progress: you show up, reply to messages, sit in meetings, keep the wheels turning. But for a lot of remote workers, especially those without clear structure, that routine can leave you feeling like you worked all day without actually moving anything forward. That feeling isn’t laziness, it’s a lack of tethering. And it’s why intentionality matters more in remote life than almost anywhere else.
The best shift I ever made was learning to match my environment to the type of work I needed to do. I block out focused time on my calendar, which are actual, recurring calendar events labeled “focus”, that let my team know when I’m deep in something. That time usually happens at home, where my setup is dialed in, distractions are low, and I can lock in without interruption. I do this to give myself explicit permission to dive into the kind of work that requires uninterrupted thought.
Lighter work like admin tasks, code reviews, anything asynchronous or reactive, tends to get done in different environments. I’ve had plenty of days where I’ll post up at a coffee shop or a co-working space, order something simple, and run through Jira tickets while catching up on Slack threads. The change in atmosphere helps shake things loose, and sometimes being around the quiet hum of other people doing their own thing adds just the right amount of structure. If you’re someone who gets restless in one space all day, rotating between locations, even if it’s just from your desk to a kitchen counter, can trick your brain into refreshing itself.
One thing I’ve come to recognize: a packed calendar doesn’t always translate to meaningful output. It’s easy to feel “on” all day when you’re jumping from call to call and staying responsive without actually moving anything important forward. That’s why I build in time to plan my week at a higher level: what needs creative energy, what’s urgent, what’s collaborative, and what can wait. When I have that mental map, I can place work where it fits best, instead of reacting to whatever lands in front of me first. Remote work gives you the flexibility to choose your focus, but that only works if you use that extra time effectively.
Visibility is also a big deal, especially in a remote setup where no one sees what you’re doing unless you tell them. That doesn’t mean bragging or sending unnecessary updates, but it does mean documenting your work, sharing your progress, and looping people in when things land. In a physical office, people might notice you staying late or hear you talking through a tricky problem. Remotely, none of that ambient awareness exists. You have to advocate for your own work, and you can do it without being loud. A clear message in Slack, a link to a closed ticket, or a short Loom walkthrough all help paint a picture. A friend of mine recently described this as “The squeaky wheel gets the grease”, which I think is fairly apt.
The reality is that remote productivity looks different for everyone. Some people thrive with strict routines and time blocks. Others work in waves. The key is figuring out what rhythms match your energy, your role, and the kind of work you’re doing—and then protecting that rhythm as best you can. Distraction is part of the game. So is flexibility. But neither has to be the enemy if you approach the work with clarity.
The most useful definition of productivity I’ve come across is about doing what matters and doing it sustainably. Remote work gives you the freedom to figure out how to make that happen. You just have to decide what’s worth focusing on and build your day around that.
Chapter 6: The Travel Chapter
One of the best parts of remote work is also the one that feels the most surreal: you can do it from almost anywhere. That sense of freedom, that ability to turn a change of scenery into part of your work routine, feels like unlocking a superpower. But “work from anywhere” quickly becomes “work from nowhere” if you don’t approach it with a healthy dose of preparation and planning.
Before I travel with my laptop, I run through the same basic checklist every time (see Chapter 1). Is the Wi-Fi actually usable for video calls, or are we talking single-bar, hotel-lobby-roulette speeds? Is there a real table and chair, or am I going to be crouched over a kitchen counter for three days straight? What’s the time zone difference, and can I realistically stay synced with my team without turning into a nocturnal cryptid? The travel fantasy only works if the basics are covered. I’ve also learned to keep my backpack prepped for mobile work, just the essentials I know I’ll need if I end up working from a different city, a friend’s apartment, or a café in another state. You don’t need perfection, but you do need reliability, especially if you’re juggling meetings or trying to ship something meaningful while away from home.
The best travel work setups I’ve had weren’t the ones where I tried to recreate my home office. They were the ones where I stayed light, flexible, and left a little room for serendipity. I’ve joined daily standups from a tiny seaside café and reviewed code while trains rolled by in the background. These are the moments that remind me why remote work is worth protecting, not because it's always easy, but because it gives you the power to align your work with the rest of your life, not the other way around.
That said, working while traveling isn’t the same as vacationing with a laptop in tow. You still need to set expectations, both with yourself and your team. When I travel, I try to communicate clearly about when I’ll be online, what I’m planning to work on, and what I might need help with. And I leave a little extra room in the schedule because things will go wrong. Power outlets might be scarce. The café might be too loud. You might need to switch locations mid-day. With time, you’ll learn to stay adaptable without compromising the quality of your work.
The beauty of remote work on the road is that it changes the texture of your day. You’re still working, but the background is different. Your breaks are a little more refreshing, your energy a little more buoyant. You’re reminded that life exists outside the four walls of your apartment. And if you plan it right, sometimes it gets better. A new environment has a way of shaking loose creative energy, giving you fresh eyes on problems you’ve been staring at too long.
So yes, remote travel is a perk. But it’s also a skill. The more you do it, the better you get at balancing spontaneity with structure, freedom with focus. It’s not always glamorous. Sometimes it’s just a different chair, in a different zip code. But done right, it becomes a reminder that work is a part of life, not something that has to sit in a separate box. (Insert Severance reference here.)
Chapter 7: Remote Work in NYC, Specifically
New York City is, in my opinion, the best place in the country to work remotely. I say that without hesitation and with a healthy amount of realism. I’ve worked remotely in Boston, Chicago/Champaign IL, San Francisco, and more than a few small cities and towns in between. Nowhere else delivers the same mix of public infrastructure, creative energy, community density, and straight-up variety. NYC was built for movement, for connection, for reinvention. And when you’re remote, that mobility is everything.
Start with the transit. You can get almost anywhere without a car, and that matters more than people realize. One of the challenges of remote work is falling into geographic ruts: same desk, same apartment, same four walls. In New York, you don’t have to fight your environment to break that pattern. You can hop a train and be in a completely different neighborhood in 20 minutes, with a different vibe, new energy, and a whole new slate of work-friendly options. That kind of fluidity keeps you unstuck. When I first moved here, it felt like it turned the whole city into an extension of my workspace.
The sheer number of cafés, libraries, and coworking spots means you’re rarely short on choices, though it should be said that doesn’t mean you’ll always find a seat. Some days, the city is just... full. Full of laptops, full of noise, full of people doing the exact same thing you’re trying to do. That’s the trade-off. The abundance is real, but so is the competition for space. If you’re someone who thrives on spontaneity, you’ll adapt. If you need total predictability, it might drive you a little nuts.
Then there’s the money. New York is expensive, and that includes remote work. If you’re not careful, your “break from the apartment” becomes a $14+ detour: subway ride, coffee, maybe a snack if you forgot breakfast. That adds up quickly, especially when you’re already paying New York rent just to have a place you barely use during the day. If you can afford the lifestyle, the city opens up in incredible ways. If you’re scraping by, you’ll start to feel the tension between loving the freedom and resenting the price tag that comes with it.
Even with those trade-offs, crowds, costs, and the occasional pigeon-related incident, New York still wins. The density of people doing interesting things, the constant churn of ideas, the way the city pulls you outside of your own bubble. It all adds up to a kind of productive energy you can’t fake. On days when I’m dragging, just being around people who are clearly building, creating, pushing toward something acts like fuel. And not the hustle-culture kind. The curiosity kind. The I-don’t-know-what-that-guy’s-working-on-but-I-hope-it’s-awesome kind.
This isn’t the city for everyone. But if you can find your rhythm here, it’s the best place to build a remote life. You can stay connected without being tethered. You can move through the day with momentum. And you can do meaningful work in a city that’s constantly reminding you why life outside the screen still matters.
Chapter 8: Long-Term Remote Life
After a few years of working remotely, the novelty fades. What you're left with is something much more interesting: the shape of your actual life. No more experimenting with whether you can work from a café or whether sweatpants count as business casual. By this point, you know what works and what doesn’t. You’ve built systems. You’ve dropped others. Remote work stops being an exception and starts becoming infrastructure. And with that shift comes a new kind of responsibility. I also think the ideal setup isn’t purely remote; it’s a hybrid model where the company has an office but no one’s required to be there. The office should offer enough perks, focus space, and social momentum that going in once in a while feels genuinely worth it. That kind of setup gives you the best of both worlds: psychological safety and autonomy, with just enough structure to stay connected.
The biggest challenge over time isn’t distraction, but drift. You start taking fewer breaks. You respond to Slack later into the evening. You stop logging off when you said you would. Not because anyone asked you to, but because the edges between work and life wear down without you noticing. Burnout doesn’t always arrive as a dramatic crash. Sometimes, it’s a slow leak. That’s why I now have calendar events that literally say “Stop Working.” It sounds silly, but the mental act of drawing a line has saved me more than once. There are exceptions to this rule, and I truly love what I do to where I could be spending my whole day writing code, but healthy boundaries are part of a healthy lifestyle.
The long-term remote life is less about finding hacks and more about designing habits. Not every day will be productive. Some weeks will be weird. But with the right rituals, the right tools, and a clear sense of what you want your work to support, not just in your job but in your life, you can build something that actually lasts. And maybe even feels good while it’s happening.
There’s no single right way to work remotely. Anyone who tells you otherwise is probably trying to sell you a desk lamp or a course. This guide isn’t meant to be definitive. It’s just what I’ve learned from a few years of trial, error, tiny victories, and a handful of missed Zoom calls. It’s for anyone trying to build a rhythm that feels sustainable or trying to do great work without burning out. It’s only human to want to stay connected to your team, city, and own attention span, even when your job doesn’t come with a cubicle.
If you take anything from this, I hope it’s the idea that remote work isn’t something you master. It’s something you keep tuning. You try new rituals. You switch up your environment. You recognize when something stops working, and you change it. The beauty of this setup is that it’s flexible by design. Protect that.
If nothing else, may you always have strong coffee, decent lighting, and pants that pass the Zoom test.