• JP

I thought I Understood Communications. Then I Took a Job at a Remote Company.

Updated: Jul 13, 2020

Life Lesson #4,698

Working at a company that has been fully remote since it's inception sounds inciting. Gaining an additional hour of sleep and additional family time in the evening is an obvious win. Not having to dress up for board meetings is a dream. Prepare dinner during lunch? Yes please. Going for a run on the local trail or to the grocery store is such a win for efficiency that I'd be crazy to go back to office life. Have you smelled the bathrooms on the MetroNorth? You get it.

This setup does come with it's fair share of ups and downs and isn't for everyone. What surprised me the most is what I learned about myself working at one of the fastest growing start-ups in the US. Not only fastest, but one that raised the most Series A in the history of remote companies! I wrote this short story about this company's personality and success to date here.

Defining the pros is easy, it's the cons that require an introspective look and an in-depth understanding of company culture. Are you an introvert? Extrovert? ISTJ? ISFP? Enneagram Type 4? Adobe The Innovator? Your personality and the way you achieve results play a more significant role at a remote company as opposed to the typical office set-up, bad lighting and all.

I like to think I excel at creating personal connections. Why send an email when you can walk down the hall? Perhaps this is my southern upbringing, waiving to every stranger along the long and narrow roads, but having conversations in-person allows you to read body language, better control the flow of the conversation and digest context. You lose the majority of this in a remote environment. What surprised me the most was how this impacts company-wide presentations on Zoom! It's hard to read the room when there is no room. I found myself second-guessing every word, bullet point and head turn because I had lost those in-person X-factors.

I moved from NC to NYC in 2001, nine days after 9/11. I arrived with a U-haul trailer, no job or no place to live in a city that would still be covered in the ashes of the World Trade Centers for the following two weeks. My cousin, who I adore and is the epitome of a New Yorker, gave me a simple piece of advice that I never imagined would translate so well to #remotelife:

"Don't look anyone in the eye and get ready to have the thickest skin imaginable."

Okay, maybe the first half doesn't apply as much, but then again, it does speak to the dynamics of physicality. I can honestly say that being part of a fully remote company requires thicker skin than living and working in NYC. Let that sink in. When you post opinions, especially at a company like TaxJar that prides itself on transparency, you open yourself up to the scrutiny of your direct reports, the CEO, CFO, CRO, COO, CIDUNNO and even your grandmother.

There's More Good Than Bad.

I've always valued collecting as much feedback as possible. Different points of view make projects better. This is true in work and in life. While in Manhattan, I soaked in all the art, culture, and religion as possible; I'm better for it. My advice is to jump in and start posting questions and opinions from the very start. This will speed up the learning curve and help paint a picture of how to optimize navigating, socializing, and learning in a remote environment.

This experience also taught me I did not communicate enough in my previous roles. Oversharing is good if approached thoughtfully. If you work in a vacuum, you won't last. It also taught me that 1:1s were even more important and that using the Five Whys technique will help uncover ways you can make an impact.

And lastly, it forced me to be more social in my personal life. Working in a silo 9-5 requires a healthy work-life balance and for me this means socializing after work or on the weekends with friends and family. Having a reason to brush your teeth is a good thing.


All I can say here is that it takes a dedicated effort to stay positive and healthy. Exercise is my silver bullet. As is voting in November. Here's to making things better and brighter through change. This may be beyond the scope of this blog post, but in today's world, I find myself seeking hope and connecting everything I do with how to make the world a better place for our son. John Lennon said it best:

Imagine there's no countries It isn't hard to do Nothing to kill or die for And no religion too Imagine all the people living life in peace, you
You may say I'm a dreamer But I'm not the only one I hope some day you'll join us And the world will be as one
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