Working Remotely: Lessons Learned

I’ve worked my entire career in tech from either a satellite office, as a remote employee, or a combination of the two. Through several life events, working remotely has been both a blessing and a curse, and this post is to highlight some of the ups and downs of working remotely as a tech employee as well some lessons learned along the way.

To set the stage, my experience has been with two of the four FANG companies (doesn’t really matter which ones, just that these are big shops), working in satellite offices, for remote teams, but in major US and Canadian cities. In both cases, the satellite offices I worked in were small at the outset but grew to exert a significant presence over time. The first satellite office was in New York. The mothership was in the Valley and I was one of the many tech kids flying the JFK to SFO circuit on a frequent basis. This brings me to point number one.

Flying back to the mothership is an essential part of your employment, especially when working in tech. Don’t underestimate regular face-time, for both social cohesion reasons as well as professional advancement reasons. There is a ton of conversation that you will miss out on, and you will miss the opportunity to influence half of the every day decisions that are made on your team. This is just how things are. In my experience, no amount of video conferencing, phone conversations, or team chat is going to change this reality. But there is an upside to this lesson. You’re already expensing, use this as an opportunity for team building exercises, drinks, food, games, etc. If your team is already good about scheduling team events once a quarter then schedule your travel around those. If your team is terrible at scheduling events (like most), then this is your opportunity to bring the fun. Which brings me to point two, though you gain in team events at work you’ll miss family events at home.

While you are away you will miss big days at home. It sucks. You don’t want to be that deadbeat dad who was too busy working to be there for the first day of school, first step, big game, etc. Seriously, don’t be that guy. But the first lesson learned should not be underestimated. The best I’ve been able to do is plan my schedule with full knowledge of my family’s schedule and avoiding big days the best I can.

The third issue with working remotely is related to the first, professional advancement. It will be significantly more challenging for you to advance in your career as a remote employee. You will miss the opportunity to influence half of all team decisions simply because you weren’t in ear shot. Furthermore, at the companies I’ve worked at, advancement is just as much political as it is merit based. If your skip levels and skip’s managers don’t know who you are or are not familiar with your work, you will have a far more difficult time landing a promotion. As a footnote to this lesson, I have zero interest in politics and self-aggrandizement. My only real interest is in learning and problem solving and I’ve put little to no effort in “reaching the next level”, so much of my frustration on this point may be self-inflicted. That said, I’d be surprised if this opinion was controversial among remote employees.

The last major downside to working remotely is isolation. There are days when I speak all of 25 words. If things aren’t going well at work it is a recipe for depression. It turns out humans need interaction, even us introverted ones. If you work too independently, you’ll often times feel like a contract worker and not necessarily part of the team. I’ve found that making shorter and more regular trips to headquarters helps with the feeling of being hired help. This issue doesn’t get the attention it deserves. This coupled with career advancement difficulties leads to feelings of discontent with team and company. And even though I have identified the issue I haven’t yet been able to ignore it. It is an issue for which I don’t yet have a remedy.

But let’s avoid smothering ourselves in negativity. Working remotely has had benefits off and on over the years. Primarily, it has allowed flexibility in my schedule when I needed it the most. For example, my oldest daughter just started school and someone needs to pick her up after school. My wife does the morning drop off so it is up to me to do the afternoons. By 3:15pm I’m in the car racing to the bus stop. After I put the kids down for bed I’m back online, finishing up whatever it was I couldn’t get done earlier in the day. Being remote has made this unorthodox work schedule possible. Without the flexibility of working from home I wouldn’t be able to keep this schedule and would very likely not be working for my current employer.

The other major upside I’ve found is related to problems one and three. Although I often feel isolated, the isolation has provided more opportunity for focus. My 7 working hours from 7am - 3pm are far more productive than my 9 hours are in an office. This is probably one of those findings where mileage will vary depending on your team, position, and individual situation.

In conclusion, I would recommend people to not work remotely unless they need the flexibility in schedule and are willing to give up professional advancement in exchange. I’d be interested in hearing different experiences on this matter.