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Matt Dailey
Matt Dailey

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Reflecting on 5 years of remote work

Let me start with what I miss. I miss seeing people in person and being able to periodically hang out with them. Everyone is feeling this now with the pandemic, but I still feel this is worth calling out as the thing that makes remote work hardest on me.

OK, let's get back on track.

Going remote

When I started working remotely, I ultimately wanted two things.

  1. To be able to work for interesting companies
  2. To live where I already lived

That was it. Articles talk a lot about perks of working remotely, but if I'm being honest, this was all I really cared about and everything else was a bonus.

At the time, I was tired of my first job and said "I don't want to work in the industry I currently am, and there aren't many other jobs around here."

It was always my wife and my plan to stay in the area so that we'd have family support when we had children. That decision has really paid off since our first was born in 2020 in the middle of the pandemic. It took 4 years, but it's vindicating to have that decision work out how we wanted it to.

So, I decided if I wanted to achieve both of my two goals, that required I work remotely. I went on StackOverflow jobs and searched "Remote, Java" which eventually landed me at Rocana, an all-remote company, which was eventually acquired by Splunk where I work now.

Remote work is a trade-off

Remote work definitely has its perks such as no commute, ability to live wherever (including somewhere with a low cost of living), the ability to reduce in-person distractions, or the ability to raid your own fridge whenever you'd like. But there are also things you miss out on like easier networking and mentorship opportunities, more difficult and missed communications, and free company swag/meals/happy hours/holiday parties.

You also can run into leaders who are less empathetic about remote work. One leader offhandedly ended a story with "and that's why I don't trust remote workers" while I was on the call (that leader has since left). Having that story ring in my ears each time I was thinking about my future and the future of my remote direct reports was pretty demoralizing.

When thinking if you want to stay remote full-time after the pandemic, these are things to think about.

What next

I see myself continuing to work remotely for the foreseeable future since my family is best suited where we are now. I definitely miss seeing people in the office, and I know that traveling to the offices will be harder post-pandemic since I have the baby at home, but I think this is still what works best for me and the family.

So, ultimately, as much as I love the flexibility and opportunities I've gotten from working remotely the last 5 years, I wanted to make sure I painted a realistic picture here. It's not completely perfect for me, but I still think it's worked out well the last few years.

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