5 Habits to Break Before Working Remotely


Fred Perrotta

Before you can learn to work remotely, you must unlearn habits from your previous, colocated jobs.

My company, Tortuga, is remote. We advocate for working remotely but know that the transition from colocated to remote isn't easy.

Jeremy and I worked together on Tortuga remotely for five years before adding anyone else to the team. I spent the last four of those years also working (mostly remotely) as a freelancer for Bay Area startups. I had a lot of time to ease into remote work, experiment, create new habits, break those habits, and to generally figure things out. My productivity varied wildly during those years, but, without anyone looking over my shoulder, I had unlimited time to work through the challenges of remote work.

For people joining an existing remote team, that will not be the case.

I've observed this with our own team. A few Tortuganauts had worked remotely in the past, mostly as freelancers. No one joined the company directly from freelance work or a remote company. Everyone had to adjust.

DHH wrote Nobody hits the ground running about new hires. This is doubly true for new remote hires.

The transition is challenging. You must not only develop new, healthy remote work habits, you must also break old habits that will hold you back. Let's discuss some of those bad habits.

The Concept of "Work" as an Office You Attend from 9-5

Remote companies don't give out Perfect Attendance Awards beacuse they don't matter. You don't get anything just for showing up. Even better, there's no where to show up to.

You are now free to skip the commute, work where you feel productive, and dress as you see fit.

You are now free to manage your own time. You don't need to be at the office by 9. You don't need to stay until 5. Hell, you can take as long of a lunch break as you want.

You have reclaimed your time and location.

Here's the tradeoff: you can no longer use either as a measure of or proxy for your work. Now, your work is your work. You will be measured by outcomes, not hours.

To become a successful remote worker, you must be able to turn your newfound autonomy into results for the company. You can no longer coast by just showing up or by accruing "ass in seat" time. Are you ready for this responsibility?

Calling Meetings for Every Damn Thing

Last weekend, my girlfriend told me about a meeting at her company. The meeting was called to decide on which part to use when their original choice was unavailable. The meeting was an hour long and included 10 people. That's 10 person hours to make a single decision.

You can probably envision this meeting.

Someone calls the meeting so that if something goes wrong, they can cite the meeting in their defense. Ten people are invited because no one is empowered to make a decision or, if they are, the other 9 people will complain if they don't get to voice their opinion. Most of the time is spent on everyone taking turns talking so that their egos are stroked.

Everyone wants to say what they think. No one wants to do the work and to be responsible for the result.

The agenda and options were unclear. If it was, the necessary people could easily make their suggestion (online and asyncronously), and the decision-maker could move forward with an alternative. Instead, 10 hours were wasted on a single part.

These are the times that try men's souls.

This bullshit happens everywhere, including at Google, where I worked.

If you have to be at work for 8+ hours anyway, why not kill an hour with a meeting? If you weren't the one who called the meeting, you can probably turn your brain off for most of it until it's time to voice your opinion. These are the time waster meetings. When you start working remotely and you reclaim ownership of your time, you'll start to really resent them. Then you'll figure out better solutions.

Of course, there is a time and a place for meetings. At Tortuga, we emphasize regular one-on-ones and team meetings. Twice per year, we sub out a one-on-one for a Mid-Year or End of Year check in, known as a Performance Review at other companies. We try to avoid back-to-back-to-back meetings to keep as many people on maker's schedules as possible.

I wrote about how we make decisions without meetings here.

Constant Availability

In an office, especially an open office, your presence makes you "available" all the time. Wearing over the ear headphones can mitigate this, but you'll still get the occasional shoulder tap.

"Got a second?"

Colocation offers the upside of serendipity and in-person collaboration. The downside of this is interruptions. Does the serendipity outweigh the interruptions?

Most offices don't have norms to control for interruptions. Everyone interrupts everyone else constantly and never thinks twice about it.

We all like chatting with a friend during the day. But what about the other 99 interruptions that day that prevented you from ever getting into flow?

Colocation makes achieving flow difficult and makes doing deep work impossible.

Even if you work remotely, you can undermine your productivity by being constantly available on Slack and email. Notifications on your computer replace taps on your shoulder.

Being unavailable is technically easier and merely a matter of choice when working remotely.

Going "away" depends on your company's communication channels but may include:

  • Notifications: Turn off notifications on your computer and put your phone on 'Do Not Disturb,' or in another rooom, or both (like me)
  • Email: Keep email closed and only check it 1-2x/day at set times
  • Slack: Turn off all audio and pop up visual notifications and all notifications for anything but DMs. Set a Do Not Disturb schedule for non-work hours. Delete Slack from your phone. Set an away message and log off for as much of the day as possible.
  • Social Media: Don't. Alternatively, like email, remove all notifications and only check it at scheduled breaks.

Waiting for Instruction

If you wait to be told what to do next, you will fail as a remote worker.

Any new job has a learning curve where you aren't sure what you should be doing, what is the next thing to do, or how to best prioritize opportunities. That's natural. Talk to your team, ask your manager for guidance, and be honest about these questions. Basically, take initiative to figure this out so that, in the future, you'll be increasingly self-guided in your work.

I always found this to be a problem in less structured internship programs. Maybe internship programs at big companies were different. I was typically one of two or three interns doing mindless work in the music industry. I always hated the system that required me to finish a task, then ask my manager what to do next. Half the time they had no idea. Interns were just around for when there was annoying work to be done. I did a lot of stapling. In retrospect, I should have been more proactive or created a more interesting job for myself. But I was young, dumb, and too tentative to take initiative.

Remote workers: don't be like Intern Fred. He was useless... unless you needed something stapled.

You can't wait around for someone to fill up your to do list with tasks. You don't have a set list of things to accomplish after which you're "done."

There is no done. There is only what's next.

Take initiative. Make something happen. If it's wrong, change it. If it's working, double down. When you aren't sure which road to take, talk to your team. You'll know which road is best and have five more to consider in the future.

Falling Victim to Parkinson's Law

Parkinson's Law states:

Work expands so as to fill the time available for its completion.

Think about those days where you didn't have much on your to do list, but still needed all 8 hours to get it done. Or the days where you had to leave work early so you were super productive and got everything done. That's Parkinson's Law at work.

When you're working remotely, you own your time. Without the rhythms of an office, you must develop your own schedule and routine. Working from home makes this especially important as you will have less contact with people throughout the day and fewer signals like "now is lunchtime" or "now you should go home."

You must build your own schedule and map out your week and days. I recommend doing this at the end of your work on Friday. Plan out the next week and let your subconscious go to work on your next batch of tasks while you enjoy your weekend.

I plan my work in Asana, our project management tool. Jeremy uses OmniFocus to maange multiple jobs and his entire life. The system doesn't matter as long as you have one.

Within a given week, you must next plan out your days. When will you start work? When will you end? When will you take breaks?

I know that these questions seem simplistic, but they're important to maintaining your sanity. I really struggled with this stuff when I worked from home while living in a tiny studio apartment in San Francisco. My desk was wedged in a corner between my bed and couch. The desk touched both pieces of furniture. I had zero separation between work and life. I never "disconnected" because my computer was always within arm's reach. Don't be like me.

Establish where within your home you work. Let that area be for work and for nothing else. When you're there, you're working. Then you close your laptop to signal to yourself that you're done working.

I divide up my days into two pieces: proactive project work and writing in the mornings and reactive and admin work in the afternoons. This system lets me be "unavailable" in the mornings when I'm most productive. In the afternoons when I'm doing shallower (less deep) work, I'm more available to chat on Slack. I'm also more responsive to emails then as that's when I'm in my inbox.

To add more structure within your day, consider the Pomodoro Technique, a system of 25-minute work sprints separated by short breaks. Use an app like Tomighty to be your timer.

In Conclusion

The list of bad work habits is endless. Some are the result of the work environment but many are due to bad habits, poor organizational design, and a lack of understanding of how to do deep work.

I could go on forever about what's wrong about colocated companies, but "5 habits" works as a clickbait title. The surprise is that this listicle is 2,000 words.

Thanks for reading and sorry for interrupting your deep work.