I’ve worked remotely my entire professional career. I’m probably one of the first generations to have had this luxury to do so for the past 10 years(I started when I was 19 years old).
When I started college, I got two part-time jobs on campus doing web apps & mobile apps for all the various departments. These jobs were great because they allowed me to study CS while also applying practical knowledge to build apps to help the school. It was a win-win setup for all involved.
Because the school didn’t have dedicated desk space for part-time workers (at least not for IT jobs), we had the ability to work anywhere we wanted. That could be between classes, at night, or even on the weekends. We just clocked in our 20-40 hours and got paid.
My second job was a job my brother got me as he had already graduated and worked for a 5 person software shop where he was the only programmer & needed someone like him to help out. The office was so small that our chairs would bump into each others when moving, so the logical thing to do was to work remotely from our apartments & come in occasionally since there wasn’t a meeting room or really any common areas to work.
Now I did have a short gig where I worked in a proper office environment for about 9 months. It was the worst job I’ve ever had. If you’ve ever seen the show “Office Space”, you’ll have a good idea of why I hated that job.

I already had a taste of what remote work was like after doing it for multiple years. When I worked remotely, I was in my element. Good at what I do. But then my days in the office became miserable. Daily interruptions. Constant distractions. Bullshit politics. I couldn’t even work on the things I was originally hired to do. I had somebody distracting me every 2 hours of my day to “check in” on the work I was doing because that was their sole job. This was when I realized I needed to go back and I immediately turned into this guy:
I’m not a lazy person. I just didn’t care. I had no motivation to work in an office. I didn’t even burn out because I was working on things I actually cared about at night. Those things lead to one of the best times of my life, a company called Xamarin.
Xamarin at it’s forefront was a remote first company. I was hired over skype and got straight to work after a short orientation in Boston. The way Xamarin worked as a company has largely shaped my views on remote work. They had instilled the very spirit of everything I dreamed about. This was heavily influenced from reading Spolsky, Atwood, Fried, DHH, and many more on remote work. Although it was never a perfect way of working, it focused on the people. People had everything they needed to make the most impact at work. They were given equipment, unlimited time off, and at least 2 in-person meetups a year that helped the team bond & establish lifelong relationships. Most importantly, people had complete autonomy to do their jobs to their maximum potential.
The team was fully distributed, the workers were decentralized. The most talented people for the job were hired remotely rather than the best person in a 30-mile radius of the office or relocating from the most prestigious university. The work was fully asynchronous where anyone around the globe could pickup the work on their own time & make an impact. Most importantly, everyone seemed extremely happy because they had a clear separation of work/life and everyone put an emphasis on taking care of the individual/family first.
Now shift forward to Microsoft. Because Microsoft is such a large company, it’s hard to really speak on this behalf. My experiences largely haven’t changed which has been great! Although I’m not a complete fan of all the remote policies (especially prior to COVID), I’m impressed that there has been a stand to do what’s right. This has helped push remote first to becoming normalized for the industry at large & there’s now skin in the game.
We’re well into the revolution of remote-working. Companies are allowing employees to work from home permanently, and people are refusing to even consider work if it’s in an office or requires a relocation. There’s fears about the quality of work & collaborations, but those are largely because companies are not yet remote first. Companies are going through a wake up call realizing that more output does not mean better outcomes. They are realizing that more output is bringing more people to the brink of burnout.
What I hope to see after these growing pains is a focus on the person. Working remotely is the future of working. It always has been. The remote worker still tends to be the afterthought. For many, it’s a battle to have your contributions seen in the company, challenges to have your voice heard in a meeting, not being included in watercooler talks, access to the office benefits, and much more. But ever since March 2020, the playing field has been leveled as remote work has become the new normal overnight.
Companies can do much more to help the average worker. This could be more hybrid work types (office/remote), more time-off, shifting to 4-day weeks, or even providing stipends to offset costs incurred(snacks, utilities, equipment, morale, learning, etc) that you may normally get in an office. What I think ultimately matters is that people have the choice. They can be supported in the same capacity depending on how they choose to work.
If you’re interested in what inspired this blog, see the following twitter thread.