Remote Work Interview with Nathan Smith

Remote Work Stories
12 April, 2022
Nathan Smith

Can you please introduce yourself?

My name is Nathan Smith. I am a principal software engineer at Microsoft, where I build incubation projects for the Office of the CTO. I primarily work with CSS, Node, and TypeScript. I initially obtained an MDiv degree, then meandered my way into tech as a career. I am currently pursuing a second master's degree in interaction design at the University of North Texas.

What is your profession, what do you do?

I work in a technology research and development capacity. Lately, my day-to-day responsibilities involve prototyping various UI ideas that may (not) become actual shippable products.

My team is currently in the process of building multiplayer games that can be played with friends and coworkers, to add a bit of levity to remote collaboration. I have also been partnering with the folks at Bonsai — Microsoft's AI platform — to teach AI "brains" to play against human (or other AI) opponents.

What company do you work for? Are you a freelancer or digital nomad?

I work full-time for Microsoft. I am part of a small team (10 people) that works within a larger organization called the Business Incubation Group (BIG), which reports to the Office of the CTO.

I have done freelance work in the past, but not as much since my kids were born. As for being nomadic, I guess you could say I am a bit of a homebody when it comes to my workflow. Having grown up as a "military brat" — regularly moving to a new city, and ultimately attending five different high schools — I enjoy the predictable familiarity of my home office.

Don't get me wrong, I do enjoy traveling. But when I do, I want to be able to focus on the experience without the distraction of work. When it comes to getting into flow at work I like the consistency of a "home base" so to speak.

How did you start with a remote work journey?

I first began working remotely in 2011, when I was with Hewlett Packard Enterprise. At the time, we were building HP's first cloud computing project. That eventually morphed into their "hybrid cloud" product offering. Since then, I have pretty much been 100% remote except for one in-office agency job.

I knew it was time to get back to working remotely when my youngest son asked my wife:

"If I am good this week, will daddy visit our house on the weekend?"

That broke me. Somehow, he had internalized that my presence in his life was contingent on his behavior.

We lived in the same house, but my daily commute was so lengthy that I would leave before he awoke and return home after he had already gone to bed. From a child's point of view, I was nothing more than a weekend visitor.

What do you think are the main benefits of working remotely?

These three are the most important factors for me.

Work-life balance

Each workday from 2:45 to 3:15pm, I step away from my desk to pick up my son from elementary school. My coworkers know that is a time slot I will not be at my computer, and everyone is cool with it.

Sometimes I chat with them via Teams on my phone, while I wait for the school to release all the students. My son always runs out at full speed, trying to sneak up on me if he can. Every time, he asks me: "Hey dad, how's work?" It always brightens my day. I would not want to give that up.

We work hard for our kids, but what they will remember most is the time we spent with them.


This is a big one. If you are on a team that operates with a "remote first" mentality — not only "remote friendly" — then you end up more thoroughly documenting every key decision. Whereas with in-office work, there is a tendency to only communicate verbally and not write down the outcomes of meetings.

I make liberal use of the wiki feature within Azure DevOps and strive to write thorough documentation for all of our internal code repositories. Not only is it good for one's coworkers and team cohesion, it also helps me to remember when I come back to a project after working on something else for awhile.


Having specific times when people get together on Teams (or Zoom, etc.) and the rest of the day implicitly for heads-down work is huge. Working in an office, I would often get my actual tasks completed off-hours during the evening because I would be so frequently interrupted by coworkers with questions. I enjoy helping and mentoring others, but sometimes that impromptu nature comes at the expense of focusing on one's own workload.

I think this is why some managers do not believe remote work is compatible with hiring junior employees, but I disagree. It is fine, as long as someone more senior is willing to set aside time to do the mentoring. That affords specific opportunities for sharing knowledge, as well as durations of uninterrupted focus for someone learning the ropes.

Do you think there are disadvantages or that you are missing something by working remotely?

It depends on perspective. If you are the type of person who likes the clout of saying you work in a particular location, or are dependent upon certain perks at your company campus, then I suppose one big disadvantage is not having access to those amenities.

Part of that though, in my opinion, is that humans tended to clump together into densely populated cities for so long that it became the norm to essentially live at work. In which case, who cares if you have a yard or how tiny your apartment is. So, companies started to provide everything they could in order to maximize that amount of time spent on-premises. That perpetuated the cycle.

For me, I would rather be "home on time."

From what cities or countries have you worked since you have become remote? What are your favorite countries or cities to work from?

I have mostly worked remotely from Frisco, TX. That is where my house (and home office) is located. In that regard, I suppose my favorite country to work from is the United States.

Bear in mind, this is simply where I found myself living when I began working remotely. My experience is not prescriptive. I am not implying that there is some sort of advantage to working remotely in the exact same way that I do. Everyone should find a workflow that suits them best.

That said, countries I have visited include: Canada, England, Estonia, Japan, and Mexico. Each of them have their own charm and unique vibe, which makes me thankful to live in a world with such diversity of thought and culture.

From what type of places do you prefer to work? Home, co-working spaces, coffee shops, or others?

I mostly prefer to work from home. Before COVID-19 hit, I would occasionally meet up with friends and former coworkers at a local coffee shop. My personal favorites are:


This coffee shop is board game themed, with lots of distractions to play with. It is a good place to host a group of people who may not know each other well, as there are plenty of icebreakers by way of gaming.

Global Peace Factory

This is more of a traditional coffee shop, and they have an upstairs area where you can reserve a table for all-day collaboration. It tends to be more quiet, and affords discussion with less distractions.

What places would you like to travel to while working remotely?

During our kids' spring break from school, my wife and I recently stayed at a cabin in Oklahoma that had decent wi-fi. While we were there, we mused about how it could make for a good weeklong getaway — she and I both work remotely — with a nice change of scenery.

I could definitely see myself doing something like that in the future. Sort of a "nature meets tech" workflow, similar in the way some of your other digital nomad interviews have touched upon.

What challenges did you face and how did you overcome them? Share your remote productivity, communication, management, etc. tips based on your experience!

One of the biggest challenges with working remotely is knowing when to metaphorically step away. It is easy to get into the mindset of always being available, because everything you need to accomplish any given task is right there. Meaning, an ideal home office can be a bit too conducive to work. So, it is important to set boundaries and specific office hours. Outside of which, guard your time.

To that end, it is helpful to remind coworkers of your time zone and set expectations for your availability. For the team I am a part of, most of them are on the west coast of the US. Whereas, I am in Texas. This means we have a two hour difference.

Generally, we shoot for about a four hour overlap of availability for meetings. After dropping off my kids at school, I typically start my workday immediately. Which means that if coworkers happen to be early risers, we can get an extra +2 hours of overlap. Occasionally, I will log some "after hours" time with coworkers if we are attempting to debug. Generally, this does not go beyond 7:00pm because 5:00pm is their end-of-business hours on the west coast.

The key is to be fluid and flexible. If someone has a doctor's appointment or a family need that arises, our team is okay with people managing their time responsibly and rounding out the level of effort in other ways. We are human, and treat each other as such.

What tools do you use to improve productivity and manage work efficiently?

We use Azure DevOps for anything and everything related to code.

  • Git repositories
  • Continuous integration deployment
  • Tracking sprints, tasks, and bugs

For iterating on design ideas, we use Figma. In fact, there are over 200+ teams at Microsoft who use it daily.

And for general communication, we of course use Teams and the rest of the MS Office suite. Our project manager is quite fond of using PowerPoint to design what she refers to as "PM art," to quickly hash out UX ideas.

How do you manage your business and taxes as a remote working professional?

Honestly, I am not sure my finances are more interesting than anyone else who is not working remotely. My wife and I do our own taxes, with the help of typical consumer SaaS tax software. We also occasionally meet with a financial advisor who helps us plan for our children's college funds, and our eventual retirement.

Some see paying taxes as a needless burden, but I think of it as a down payment on the future of our country. It is important to support public school teachers, libraries, and all the other social infrastructure that is key to a healthy modern society. I do wish our tax laws were a bit more sensible, and that we did not have so many tax haven loopholes that drain potential revenue.

Also, stricter oversight and actual enforcement of insider trading within our own government would be nice too. I definitely feel that the proletariate are held to a different set of rules than the politicians, which is sad.

What advice would you give to people looking to work remotely?

I would offer these tips.

Perhaps most importantly, invest in a comfortable chair. It is where you will spend quite a bit of time, so it may be worth the extra expense to get something a little more high-end. It will pay dividends later, and your back will thank you.

If a standing desk is more your style, that works too. The main point is to make sure that you are physically comfortable, so that work does not feel like a drudgery. One of my developer friends walks on a treadmill throughout his workday. Find what suits you.

  • Carve out a place that is specifically for work. I know it seems silly, but it is good to mentally separate: "This area is for work" as opposed to the rest of one's dwelling. Preferably somewhere quiet where you cannot be easily distracted.
  • Take regular breaks. Seriously, it is fine. Sometimes I find my attention waning, where I am mentally stuck on a logic problem. In those occasions, I will go into the kitchen and cut up an apple. Or, I will pour a small bowl of mixed nuts and take it back into my office. Sometimes a healthy boost of blood sugar can help stimulate the mind. Maybe even go on a brief midday walk to clear your head. Switch it up, and I think you will find that you have increased clarity when you return to the task at hand.

If you work for a company that — in spite of all the supporting evidence shown during the COVID-19 lockdown — is still reluctant to allow for remote work, I think my first suggestion would be to constantly keep a lookout for another job.

Any employer still dogmatically insisting on rigid in-office workflows (especially for "knowledge workers") is stuck in the past and/or willfully ignorant about how to best utilize their staff.

Whether or not a manager allows for remote work says a lot more about the efficacy of their own administrative skills than it does about a team. I mean, if one cannot trust employees unless they are within the same building… Is that boss actually any good at interviewing and hiring? If not, the solution could be entirely different leadership.

Do you work on any side projects?

Not as much lately, since my kids are at an age where there are lots of extracurricular activities to keep up with as a parent. However, I did recently build a "best in class" (in my clearly biased opinion) call-to-action modal. You can play around with the interactive demo here.

It is available as an open source NPM package. It is somewhat unique because it only requires authoring HTML to use. Many other third-party modal approaches involve writing a fair bit of additional JavaScript in order for things to work.

Here is a list of a few projects I have made over the years.

There is a more extensive list on my GitHub profile.

Would you like to share earnings from your side projects? Please share.

I run a single, small ad (via Carbon) on the sites I have built for my various open source projects. Before the advent of ad blocking browser plugins, I used to make roughly $10k a year in passive income from those ads.

However, now that most people use an ad blocker — either as a plugin, or a native browser feature — that has dwindled into a trickle of (at best) maybe $30.00 per month. One might assume I would be upset about that, but honestly I think the web is probably better off with less obtrusive advertisement. So, I am okay with it.

Would you like to share any interesting stories while you worked remotely? Please share if you can.

Having spent a month in Manhattan a few years ago — sitting at a physical desk, within an investment bank's overcrowded office — connected to a cloud based PC remotely… I could not help but wonder.

"Why do any of us need to be here?"

We were all in the same building, but communicating across different floors. I met other full-time employees who would fly in from various midwest states — four days per week, several weeks per year — just to have in-person meetings that could have been an email. That blew my mind.

They would drop heavy hints about how I was integral to their dev team, and that I really ought to become full-time instead of a contractor. I was polite, but felt like this.

"You know what is cooler than a skyline view and kombucha on tap? Not having to commute to any office."

Ultimately, having proven ourselves on the project — and after showing the FinTech client how much they were spending on reimbursing airfare and hotel costs — our agency was able to negotiate having our out-of-state folks work remotely. With the money saved, we were able to have another principal level developer on the project as well.

We ended up becoming their preferred "agency of record," nudging out another company that was actually located in the same city. Our work was that much better, because we could hire top-notch people from anywhere.

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