9 Principles To Better Remote Work

Because work doesn’t translate directly from the office to home.

Jake Kahana
Mar 13 · 13 min read
Cavedwellers Meet Up In Our Remote Cave For Focused Work

We’re living in really interesting (and somewhat dramatic) times. Cities are going into panic. Events are being canceled. People have to work from home.

For some of us, remote work is a luxury and a perk, for others, remote work is now a requirement and maybe not something we’re actively choosing.

In 2018, 40% of the workforce was independent and in the next 5 years will be the majority. And 95% of people who have worked remotely in some capacity want to work remotely as a part of their work. Remote work is here to stay.

At Caveday, we’ve led tens of thousands of hours of deep work for our community in The Cave– our 3.5 hour facilitated focus sessions, both in-person and remotely over Zoom.

Two years ago, we created the Remote Cave. We were researching and learning about our diminishing attention spans and wanted to help independent and remote workers make the most of their time by creating a focused work session to do their most important work, from anywhere.

The first time I ever worked remotely was in 2015, I was part of a team of 4. None of us had worked remotely before, but we all agreed it should be part of our team culture. I was in Portland, OR and the rest of the team was in New York. What ended up happening was basically I did 3-ish hours of work, and tried not to get caught. I would join calls from bed, meetings from coffee shops, and send emails from long lunches. I did work, just didn’t feel like I was working. It was a pretty unproductive week and my team had to pick up my slack.

When systems are not in place, and people aren’t clear on what’s expected, work falls apart and distrust or resentment can form. When you’re not clear about what remote work looks like, things can go wrong.

My cofounders and I have experienced (with some success and lots of failure) a range of what works and doesn’t work when it comes to remote. Here are the 9 principles to make remote, work.


Principle 1: Be Accessible from Anywhere

If we’re not going to be in an office, we need to free ourselves from having all of our things on one computer or one LAN or local server. This is table stakes at this point, but not knowing who’s reading this, I wanted to make sure that at the very least this is where I start.

Have your software, files, calendar, project management, and communications be cloud-based.

Share Calendars

Obviously what happens when we go remote is that our calendars need to be digital. Sharing your availability and being able to check your schedule from any computer will make keeping your schedule and communicating availability easier.

Share Files

Remote work only works if you can access the files you need and share them with your team and clients. Cloud storage is easy and works just like your files on your desktop. Almost all platforms even allow you to sync your desktop with the cloud.

Use Proper Communication Tools

You’ll first want a system of quick communication. Email is fine, but threads and searching and the immediacy doesn’t always translate. Finding the right instant messaging platform.

Meetings are not just in conference rooms anymore, so having a reliable video chat platform can help with connectivity and personal connection.

Track Projects and Tasks

Keeping track of assignments, to-dos, and workflows becomes really helpful as work becomes more collaborative without the same visibility. Shared project management software allows the team to know what’s going on and what needs attention.

The rule of thumb here is to click around a little bit and see what works for you. Some people like a lot of customization and complexity. Some people like simplicity. These should enable your work, not block it.

Principle 2: Tech Should Improve, Not Impair Your Work

Ultimately, we live in a world where technology is supposed to make our lives better but it often gets in the way. We’ve put together a list of tools to block distractions, keep track of your time, and help make your systems easier here.

We recommend having these applications on your phone (Chat, Email, File sharing, Calendars). But be conscious about how you’re using notifications and even turning them off completely. (Or just allowing notification from direct contact chats and messages, not email).

Microsoft did a study that showed the average focus time in the office is 40 seconds! That’s not just from coworkers interrupting or noise around you. That’s also from our own distractions. We unlock our phones on average of 80 times a day and touch it over 8,000 times. We get in the way of our own productivity. So put your phone out of reach and out of sight, and turn off notifications if you can.

You can make your phone functional and a tool for work without making it a distraction FROM work.

Principle 3: Set Team Agreements

There is a lot of uncertainty in Remote Work– what people are working on, where they are, what happens if I need to unplug and do some deep work? We talk a lot about the first day of kindergarten as a model. Kids sit around the room and the teacher asks, “what are the rules of the playground?” Together, they come up with the agreements, which are hung up on the wall and they become the regulations of the class. But we don’t ever do anything like that at work.

As your team is growing and changing and moving to remotely, sitting down and having some specific definitions will be very important.

We have a really helpful guide for gathering and defining team agreements. You can see our discussion guide here.

Essentially, we start with some personal habits and work styles. Then open up a discussion around 4 topics: 1. Communication, 2. Gathering, 3. Scheduling, and 4. Productivity.

(Note: Even if you’re not on a team, defining some of these questions for yourself is very important.)

What are working hours?
What if I need to go offline for a bit — either for work or for personal reasons?
I want to be social. Who’s up for a break?
How do we get feedback?
What happens in an emergency? How do we contact everyone?


Ok so you’ve got your systems in place. You’ve synced up your files and shared your calendar, and accessed your work from your phone, your laptop and your desktop.

But uh oh. The fridge is full of food. The couch is so inviting. Your bed misses you and your TV is calling your name. And the internet is endless! How are you ever going to get things done?

Washington State University neuroscientist Jaak Panksepp found that “seeking” is one of the fundamental impulses for all living things. The act of searching is driven by dopamine. We seek out that feel-good chemical in distractions. Dopamine also comes out of our work, but not until we’ve accomplished something or gotten into a state of “flow” which takes a bit longer than a quick check to Instagram or email. So we need to find ways to manage that desire. Especially because no one is watching you.

One theme that keeps coming up as we move on to implementing habits, is becoming your own manager. We need to develop and implement our own structure to establish habits that enforce the kind of behavior that helps us thrive and do our best work.

Principle 4: Start and End Your Day

This is going to sound painfully obvious, but most people don’t do this. Start and end your day. Create some sort of mental trigger to indicate when you are “at work” and when you are “off.”

If you don’t start your day or treat this like work, you are just at home. With work constantly distracting you from your life.

Morning rituals might be to get showered and dressed. Shoes make a big difference, too. We put on shoes to work, we take them off when we’re done. A simple cue like putting on shoes or going for a fake commute like a walk around the block creates space for us to transition.

The same goes for ending your day. It could be as simple as spending 15 minutes reviewing your open to-do items, responding to any last urgent emails and Slacks, closing tabs, and reviewing your calendar and making tomorrow’s to-do. Fake a commute home. Pick a 10-minute podcast, walk around the block and come back. Make a personal phone call. Schedule a gym class or appointment to force you to get out of the house at the same time.

These mental cues will help create better boundaries and ensure that work doesn’t bleed into the rest of your life.

Principle 5: Boundaries Create Freedom

There are some amazing benefits of working remotely, but we can only get there if we’re being responsible. The more flexible you want to be in taking breaks and working on your own schedule, the more responsible you have to be in your habits and structure. You need clearer boundaries and stricter rules for actually working, so the rest becomes easy.

Want the ability to take a short power nap? Deliver on deadlines and participate in meetings. Want to work from the beach? Better be good at communicating your availability and responding on-time.

If you don’t have any boundaries between your work and the rest of your life, you end up feeling like you’re chained to your work email and constantly “on” and available.

That’s a recipe for burnout.

So first, set up your space.
A place that feels good to work. A comfortable chair and clean desk (not a couch or bed). This area will be mentally connected with work. Every time you sit there, you’ll be working. Every time you stand up or get out, you’re done or on a break. We’re trying to trick our brain to go into “work mode” instead of conditioning ourselves that work happens all over the house. Without designating a space, you’ll feel like you’re always working.

It’ll help to leave your chargers and even your computer there. Don’t be tempted to bring your laptop to the couch, bed, or bathroom (I’ve seen it).

Block Out Your Schedule
Block time for deep work, shallow or administrative work, emails, lunch, snacks, breaks, and social time. Don’t leave your focus competing with your impulses. Be disciplined about your schedule while the habits are still being formed.

I’d recommend a small kitchen timer that you can wind up for 3–4 minute breaks. Or 45 minute deep work sprints. It will keep you out of your calendar tab and will give you the physical reminder you need to stay with whatever it is you’re doing.

As we encourage in the cave… MONOTASK!

Next, put away your phone.

The University of Chicago did a study in 2017 that showed that having your phone on your desk–even if it’s upside down even if it’s airplane mode– temporarily reduces your cognitive abilities. In other words, it makes you dumber.

One step further than just putting your phone out of reach and out of sight, close tabs you don’t need and turn off notifications, especially during deep work time.

Principle 6: If you wouldn’t do it at work, don’t do it at home

Be Present To Your Coworkers
That means turning your video on during chats, dressing appropriately, and being present enough to participate during meetings.

It’s hard, but the more you give your team your presence and attention, the more trust you build and the quicker your meetings will go because everyone will know what’s going on.

In an office, if I see you at your desk, I assume you’re working. But because we can’t see each other remotely, I need to find some other way to make myself visible. We do that remotely by communicating our status. What are you doing now? Are you working? Available? Looking for a break?

If you’re using Slack or Skype or any chat platform, set your status and be visible to your team.

Be Present For Your Work
Limit multitasking. No TV, Netflix, Instagram, or other distractions other than music. No eating at your desk. Multitasking is not a real thing. Studies continue to show that people cannot focus on more than one task at a time when it requires thinking. It’s now what tech writer Linda Stone coined “continuous partial attention.” Psychologists used this phrase to talk about how our tasks gets the least possible attention. So not only does our focus and attention deplete faster, but we’re also not ever focused on what we’re doing. Our mind is constantly somewhere else.

This shallow work leads to more mistakes, more effort, and poorer learning and retention of information. All in all, not worth it.

In short, monotask.


Now might be a great time to take a 30-second break.
Stand up. Roll your neck slowly all the way around. Again. And reverse.
Then stretch your fingers.
Roll your wrists.
And the other direction.
Take a deep breath.

And let’s come back.


Mental health and self-care are important to keeping a healthy relationship to work. To feeling good every day, showing up, and being fully present. To sustaining focus for long periods of time and not feeling rushed when you’re taking a break or socially connecting with your team.

Principle 7: Don’t Forget You’re Human

At Caveday, when we think about wellbeing, we break that down into physical, mental, and emotional health.

Listen to your body
To do your best work, you need to be present and address your body’s needs. That means having real lunches (ie away from your computer), healthy snacks, drinking lots of water. Exercising a few times a week is very helpful for this as well.

Let Your Mind Re-Energize
Taking a break about every 45–50 minutes. Your brain can only focus at its best for up to 52 minutes. So just to stand up, walk around the room and come back can help re-energize. Unlike an office, being at home means less judgment if you need a good 15-minute power nap. That’s way healthier than drinking an energy drink or overdoing the caffeine.

Again, we believe that if you want to fully embrace some of the perks of working remotely, it requires disciplined boundaries and structured work habits.

And one huge component, often overlooked is the emotional component: social connection, feeling seen, celebrated, and rewarding wins. Which leads us to our next principle.

Principle 8: It’s Not All About The Work

We need social connection and to feel seen and heard by our peers. And remote can be really hard to connect. Technology can act as a barrier. You can’t read my tone or facial expressions or body language as I type this. Even in video chat, making direct eye contact is nearly impossible. That can be challenging to build trust and even feel connected to each other.

In order to overcome these tech barriers, we all have to put in a little extra effort into finding ways to connect, share, laugh, and get to know each other better.

You can think of it like summer camp: theme days, colors wars, book clubs, lunch & learns, remote happy hours, etc. Be creative, have fun. As long as you’re finding ways to connect and see each other as humans, not just invisible coworkers.

Building in non-work time is re-energizing to our emotional wellbeing. It makes our work better.

Principle 9: Change Is Ambiguous and Takes More Time Than You Think

Change is hard. Being adaptable and resilient in the face of dramatic change is going to take not only logistical work but emotional support. We have to acknowledge that all change is both positive and negative. There will be some benefits. There will be some challenges. It will always be somewhat ambiguous.

Adapt and Experiment
Part of the success of the next few months and getting into remote work is being flexible with HOW you work. The speed and pace may be different than in-person work. It may be faster, it may be slower. Check-in on your team, try new things. Fewer meetings and more check-ins. Block off time for no meetings a few days a week. Try daily check-ins. See what works for you and your team.

Working remotely also requires that we think differently about our output and what it means to work hard. We’re not working hard by working more hours. We work hard by delivering our work on time and by collaborating well with our team.

Evaluate based on output, not on hours.
For managers, that can be challenging– not to be judgemental about how that looks or giving people a hard time for being offline or not responding to messages on nights and weekends. For employees, it means being clear about what your task is, what is needed of you, and present with your work while you’re doing it.


Our hope is that as we dive deeper into these principles, you can learn new habits, implement new systems, or refine your current behavior to be more focused, accomplish more, and improve your relationship to work by being more effective out of the office.

We can help. Join us in The Cave.

Our remote Caves are 3.5-hour deep focus sessions on Zoom. Each one is led by a Cave Guide who divides the day into sprints to stay focused and energizing breaks to keep you connected.

We’ve used the science of productivity and the latest research to design our method to include non-work social connection to recreate the serendipity and ideation that come from casual office run-ins. The Cave is engineered to overcome loneliness while maintaining focus and productivity.

We also host Sunday nights at 7pm EST and Tuesday morning at 730am EST.

Try it out for $25 a drop-in.
Or jump right in and get an unlimited membership for only $35/month (as low as $1.25 per Cave)!

www.caveday.org/remote

caveday.org/remote
caveday.org/remote
See you in The Cave.

Caveday is a company aimed at improving your relationship to work. We write regular posts on Medium and send out monthly newsletters with productivity tips, life hacks, and recommendations. Sign up for the mailing list here.

Or sign up for Jake Kahana’s personal emails, called “The Email Refrigerator” here.

Caveday

Ideas and stories to improve your relationship to work

Thanks to Nicole Walden

Jake Kahana

Written by

Artist and teacher helping people thrive in a distracting world by leading them in unlearning. Cofounder of Caveday.org and US faculty at TheSchoolofLife.com

Caveday

Caveday

Ideas and stories to improve your relationship to work

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