Lessons Learned from 6 Years of Working in My Pajamas

The alchemy of remote work is that location becomes irrelevant; you can quite literally build a team, culture, and company without borders.

At Help Scout, I’m proud of the remote culture we’ve created. I’ll be the first to tell you we’ve made plenty of mistakes along the way, but we’ve sought to learn from each one.

Three years of freelance work and three years here at Help Scout have given me some firm opinions on the topic. If I’ve learned anything, it’s this.

1. Writing affects everything you do.

There’s a reason why "hire the better writer" is such prevalent advice: clear writing means clear thinking. The cost of confusing a teammate or a customer is high, but pales in comparison to the cost of confusing yourself. Since remote communication is built almost exclusively around writing, you need to be able to firmly grasp complex ideas and explain them in plain language.

2. You must control how you end the workday.

When working from home, it can be hard to “turn off” at the end of the day. How much work is enough when you’re mostly managing your own time? To quote Jo Bennett from The Office, “If you can put your name on this day, and be proud of the amount of work you’ve done, then by all means, you should tootle on home.”

If that means a slightly shorter, more restful Wednesday in favor of a long Thursday, so be it. Great work isn’t about hours spent but meaningful tasks accomplished. You’re done when you can proudly sign your name.

3. Leadership must buy in, or you’re sure to fail.

You can’t succeed as a remote worker if your company isn’t built around remote work. Even if you have an office headquarters, the team has to choose between a remote culture or an office culture, because there is no in-between. An office culture that makes exceptions for remote people results in second-class citizenship, putting a muzzle on your potential.

4. You gain personal productivity at the expense of collaboration.

A universal tradeoff in remote work. The focus and output to be had when you manage your own time is staggering, but you have to pay the piper; collaboration will require more effort. The trick is to balance the improved personal productivity with team productivity, or the rate at which the team completes to-dos where two or more members are working together. Time is of the essence, and success depends on moving fast, being responsive, and actually adhering to the organized practices within the company.

5. Work to control your environment.

For many people, a strict association of external stimuli helps create headspace. Here is where I work, here is where I live. When work and home collide, you need to set your own boundaries. I keep my home office door closed at all times, as if to separate it from the rest of my house; it’s sacred ground where nothing but work can be done. Without a similar practice, you’ll find “home” becomes an amorphous location where you’re unable to divide working and winding down.

6. Chat apps = shoulder taps.

While the in-person distractions of an office are gone, company-wide messaging apps are the replacement. They’re useful for keeping emails to a minimum, but many people will have pings and alerts enabled, so messaging is still an interruption. That’s okay. Interruptions are necessary from time to time, but choose wisely. A messaging hierarchy that the whole team follows is helpful. Start with defining which messages are appropriate for which channels of communication.

7. Get comfortable with asking for quiet time.

People-pleasers beware: because nobody can see what you’re doing, nobody knows the best time to interrupt you. Asynchronous communication is assumed for everything except urgent tasks and meetings, but out of the goodness of your heart you’ll probably try to respond to emails and IMs right away. Don’t. When you need to shut things down to get difficult work done, be firm (but friendly) about your unavailability.

8. Always assume miscommunication over malice.

The remote worker’s version of Hanlon’s razor. Some interactions will feel cold due to the human tendency to misinterpret emotionless text. Jokes and sarcasm don’t translate perfectly, there’s no body language to interpret, and conversations via chat can be interrupted at any time, making it laughably easy to assume a severe tone where one wasn’t intended. Stick to assuming positive intent; when working with great people, you’ll rarely be wrong.

9. Water-cooler moments matter more than you think.

Silence isn’t always golden, because small talk creates connections most of us don’t appreciate until they’re gone. Even aimless chats can influence creative input, give you early feedback, and inform you of goings-on in the company. As a substitute, opt for a mix of scheduled and impromptu one-on-ones, such as a weekly session with your team lead and casual conversations like “Friday Fika” with someone outside of your department (read more about Fika here).

10. You are responsible for giving context.

We went a few months this year without a single internal update on how the blog was doing, and that was on me. I thought everyone outside marketing wasn’t interested, but of course that was false—the best teams want to know a little about how everything works. This small sampling brings peace of mind and even helps improve your own work. I look forward to every support update, for example, because I get to learn that much more about our customers.

11. Trust begets trust.

No one wants a manager breathing down their neck. In remote work, a good manager does the opposite—you will have to be trusted to get things done. In turn, you need to trust your team lead. If you’re the manager, the moment you move from organized check-ins to obnoxious pestering is the moment you become that former boss you used to hate; if you want people to trust you, trust them first.

12. The first few days are incredibly awkward.

I had it easy since I joined early on and had previous remote experience. For many, working remotely is a seismic shift, so onboarding new people becomes especially important. One of my favorite practices that we’ve put into place is the “new work best friend.” Someone from the team always steps up to be your pal right when you’re hired—perfect for getting answers to “silly” questions, learning about unwritten rules, and feeling at ease when adjusting to a new company, new practices, and new faces, all while being hundreds/thousands of miles away.

13. I’d recommend not working in your pajamas.

The grand reveal: I don’t actually work in my pajamas. It’s a prevailing stereotype I’ll happily poke fun at, because most of us put on clothes that we aren’t ashamed to be seen wearing outside. “Look the part, be the part” is true: when you look put together you feel put together, and that affects your mood, your confidence, and your work as a whole.

Perhaps the best part about remote work is the opportunity it allows. The people you work with impact more than your career; as if those countless hours spent with them won’t rub off on you. You’d better choose wisely.

If you see a group of folks heading where you want to go, remote work gives you a chance to tag along, no matter where you are. I’m thankful for that.

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