What I’ve Learned From My First 2 Years Working Remotely

This isn’t the first time I’ve written about working remotely. I did so after my first three months and then again last year.

While I love it, I wouldn’t feel right only talking about the “epic stuff.” The highs and lows are so much more extreme and intense. That was something that caught me off guard.

I got into remote work because I was drawn to the FREEDOM and uncharted opportunities it offered.

The real truth is remote work is hard. Way harder than all those blog posts talking about working in your PJs or in a hammock make it out to be.

It also has a way of drawing out all of my insecurities. Often times, all at once.

In this post, I talked in detail about one of those insecurities: struggling with feeling like a fraud. Imposter syndrome is real and dealing with it when you work remotely is 10x harder.

The hardest part isn’t so much the actual work but the fact that it has a way of drawing out self doubt and weaknesses in painfully obvious ways.

For example, when I first started working remotely, I was amazed by how much stuff I can get done in a relatively short amount of time when you don’t have to attend like 20 meetings every week.

Early on, I felt like I was the most productive I’ve ever been.

But, productivity by itself isn’t always so great. You can be crazy productive but still be spinning your wheels and not accomplishing much of anything. Or only doing the easy repetitive work instead of the harder, more strategic work. If you are just crossing off a ton of tasks on a to-do list, it is easy to get tunnel-vision into simply being productive and lose sight of a higher-level strategy or the big-picture.

Not too mention, when you are more productive, you are going to take on more projects. You might be able to do all of the things, but the quality of the work won’t be as good as if you only did one or two of the things instead of 6.

Often times, the most productive thing you can do is to simplify and do less.

Instead of trying to work on 6 projects, choose 1 or 2 projects that have the potential to net the biggest payouts.  That could be the project with the biggest growth potential. Or simply choosing the project that solves a real, current pain point (i.e. painkiller) over a vitamin (i.e prevention).

This is way easier said than done especially if you battle with self doubt, feeling insecure from time to time or have ADD tendencies. Or in my case – deal with this unpleasant trifecta. You’ll fight hard against focusing on only a few things instead of trying to do ALL.THE.THINGS. or checking out the latest and greatest shiny object.

This ability to focus on the most important thing ties directly in with something else I’m learning a ton about communication.

Being a writer I’ve always thought I’m a pretty good communicator -especially when it comes to written communication.

When more than 90% of your work takes place online, I quickly realized I have a lot more to learn when it comes to being a better communicator.

When you think of communication in the workplace, you usually think of these four things..

-Communicating what you are working on.
-Communicating results of what you are working on.
-Playing nice with others.
-Identifying and setting priorities

The reality is communication is so much more than what you say or write. It is all about context or how you say or write it. Context is everything when most of your communication takes places in writing or over phone and video calls.

No one is a mind-reader. It is hard enough to try and understand what someone might be thinking in person. It is downright impossible through a video or audio call on Skype or in an Slack message. You have to speak up and listen so much more.

In fact, I’d argue it is pretty much impossible to over-communicate.

It is incredibly easy for even the simplest, most mundane request or comment on Slack to be taken out of context

For example, a vague message like – “do you have a minute to jump on Skype?” that comes seemingly out of the blue with no additional context can produce a million thoughts in my brain. Most of them are panic inducing.

* Like – oh shit- what did I screw up this time?
* Oh great, so and so just found out I have no clue what I’m doing on this project (cue imposter thoughts)

Of course the other person knows none of this. You hop on the call and it turns out the person just wanted to brainstorm an idea or ask a question that had too much context to type in say Slack.

Even the littlest comments can be taken out of context and lead to confusion, frustration, rumor spreading, lost productivity, etc if you aren’t willing to be open, extremely communicative and not shy away from resolving conflicts.

In addition to context, rock solid communication is also all about knowing when to keep plugging away on a project and when to ask for help or bring in more people or resources.

To do that, you have to be able to evaluate yourself objectively and know what you are strengths are, your weaknesses are and how to communicate them effectively. It is tricky and I’m not even going to pretend to be an expert on this.

All I can say is it helps to have an optimistic or positive outlook. If you go in and naturally assume that everyone you work with has the best intentions, wants to be helpful and they are just doing their best and not trying to screw you over, it is going to make your work more collaborative and way less stressful. It also becomes easier to ask for help.

As you saw from my example earlier, it is laughably easy to take something out of context or assume the worst when most of your comms takes place on Slack, email or on calls (audio and video).

Life Hack – if you want to be more positive, surround yourself with other positive people. Positivity rubs off. This goes doubly for what you consume. Watching and listening to the news can have a big impact on your world and personal outlook. 95% of the news is either drama, gossip-bait, scandals, murders or negative in tone.

Studies show that people tend to interpret written messages more negatively than they were intended. So when you have trained yourself to have a more positive outlook, more people are not only more likely to want to hang around you more but you’ll also have less issues misinterpreting these messages.

When you do read a message or interpret a call more negatively or completely out of context, you’ll be more likely to spot the trigger(s) that may have caused it.

For example, I know I am way more likely to read too much into a message or take something negatively when:

* I haven’t gotten enough sleep the night before.
* Or when I’m feeling insecure about where I stand on a project or even just in general.

When you can identify your triggers, you can do something about it.

The first trigger is easy enough to hack by trying to consistently get 7 hours of sleep a night (when I perform my best). Or if I don’t get enough sleep the night before, grab a power nap midday.

The second trigger is a bit harder. When, I’m feeling insecure, i have a tendency to overwork and tend to misread interactions and comments as more negative than they really are.

I’m not great about this, but the only reliable way I’ve found to get past this is to speak up to someone who you work with or one of my friends who is also a community pro. (Note: I used to try to just talk it out to friends and family. At least for me, it doesn’t work as well because they can’t understand the full context and their advice – while well-intentioned- isn’t always helpful. Many times, I found myself more lonely or insecure after talking to a really good friend.)

It can be scary to open up about feeling overwhelmed or stuck on a project. I’ve learned that most people don’t expect you to be perfect all the time or to have all the answers.

This is something I struggled with (and still do) early on in my career. I thought it was a sign of weakness to admit when you didn’t know something or had to ask for help.

I realize it is quite the opposite.

Most people respect people who are open and honest and good at communicating where they are at and where they may be struggling. I’ve found that most people will respect you a lot more when you are open to explaining that you don’t know something but are working to figure it out than if you tried to cover it up with some BS excuse.

In that sense, remote work has forced me to become way more open and vulnerable. Uncomfortably so for a nerdy introvert who tends to be pretty private and reserved by default.

Working remotely is a skill – just like learning how to market, write or code- and one that you have to constantly work at. If you lack communication skills or the self awareness to know what you are good at and what you suck at, you’ll constantly feel like you are moving a boulder up hill.

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