My Remote Worker Journey

Finding a remote job may seem difficult or out of reach, but if you’re strategic, patient and willing to experiment with different options you can quickly find your way into a growth oriented career that allows for location flexibility.

To start off - I don’t really consider a remote career to be the same as being a digital nomad. While these terms may seem similar, the term digital nomad has evolved into describing people who use geo-arbitrage to match low cost of living and fun areas across the globe with income that provides you with a good lifestyle. There’s nothing inherently wrong with this (in theory), but keep in mind that traveling constantly and trying to be a good employee don’t often mix - as a entrepreneur who’s hired and fired dozens of employees, I can count on one hand the number of people I’ve seen pull off perpetual travel and work effectively..

When I was in my 20’s I did a lot of research into my personality type - Myers Briggs helped me tease out some of the reasons I was so off kilter in many personal, social and professional situations and give me a glide path to at least cutting myself some slack whenever possible and developing coping mechanisms for the stressors that really bothered me (and confused those around me to why they were a big deal).

I had several jobs that required long, expensive and taxing commutes like many millions of others in the U.S. I graduated college just before the great recession really started kicking off with an absolutely massive student loan that I could barely afford the payments on - I worked at these on-site jobs because I had to, not because I wanted to. To think back, remote work as a norm was not even a thing people considered as an option - but some people were able to do it.

My first job doing customer support at an enterprise media analytics company was when I realized that remote work just may be the path to go. I sat in a drab cubicle in a nondescript office in the suburbs of Boston. I liked my coworkers quite a bit at the time - all the facetime spent complaining about the nature of our bosses, the industry and cracking lots of dumb jokes created decent bonds with these people, some of whom I keep in touch with today. But even though these people accepted me as another coworker, we were really not on the same level.

I was fresh out of college with a degree in communications with no real skills beyond my ability and eagerness to express myself through writing (which wasn’t required or needed for this job). I did notice that certain people were not always in the office - I didn’t quite understand why, but I would find out that during big deployments of new software and bug fixed, there were people who had to bring home the mobile laptops with the VPN’s to be “on-call” in case something broke. Oftentimes this would lead to late and long hours throughout the weekend and whomever would be on-call was often just allowed to stay home for a day or two and work from there with the company laptop seeing as they already had it. I learned that with some SQL and Excel skills I could be among these people so I worked hard to get to the point where I was eligible to fill-in for one of the QA engineers who was taking a vacation.

At this point in my life I was just in my early 20’s with a girlfriend, no kids and not much of a social life (I couldn’t afford one). So for me the experience of getting good at something that earned me a bit of freedom made all the sense in the world. This act of subversion did not go unnoticed though and once a VP from another department noticed that I was out of the office more than I was in it I was pulled aside and told this wouldn’t fly anymore - basically I was to work nights and weekends with the remote laptop and I was still expected to be in the office after and all-nighter unless otherwise notified. I bristled at this, realized it was mostly about who controlled the situation and boiled down to a lot of organizational nonsense that I simply didn’t respect or care to engage with. I quit a week later for a job that explicitly allowed me to work from home 100% of the time (the company’s headquarters was out of state) and even got a slight pay bump.

Fast forward to today, remote work is far more normal, but there are some risks and trade-offs of being remote that people at all levels of their career should consider.

Consider Relocating or Traveling Often

Just because you don’t want to come to an office every day doesn’t mean you shouldn’t pick the area you live in carefully. If you have the ability to relocate to an area that matches your lifestyle desires, but also has other professionals that you can network with and learn from, you can better grow your career.

If you are someone that really needs and wants to live in a place isolated from city life but also want to be a remote worker, you’ll likely need to force yourself to travel to industry events and conferences often. I don’t recommend becoming a conference rat for the sake of the free swag though - make sure you’re able to meet other people in person and even add some value through giving talks, trainings and presentations.

Traveling for work too much when you don’t need to is a great way to burn yourself out and make yourself extremely unproductive. But the right amount of face-time can really boost your career.

Also, try to join remote teams that are committed to getting together in person at least a couple times a year - this strengthens your bonds and makes working together way more enjoyable.

Be Specialized In Something Useful

There’s a lot of debate about whether specializing in your career is a good for a bad thing. Some would argue that people who are too specialized become commodities and are easily replaced, however if you pick your specialty carefully and become really good at it, that’s not something you necessarily need to worry about on a day to day basis. When a specific problem calls for a specific specialty, the specialist has the leverage. The employer can be more confident than hiring a generalist, who may have blind spots or weaknesses in their skill set. Often times even companies that have a portion of their workforce in-office will be forced to hire remote workers due to the fact that they simply cannot find anyone locally that meets their needs and they don’t want to pay people to relocate, which is super expensive.

In the same vein, stay nimble and never stop learning. The specialty of today won’t the specialty of tomorrow. Getting comfortable, sitting on your laurels and expecting job security is foolish. Plus, learning new things is fun and keeps you young!

Be Thoughtful About Pay

In the same way you think about where you want to live from a lifestyle perspective, you’ll need to think about how much pay you’ll need to support your lifestyle. When times are good and money is flowing (ZIRP), maybe you can secure a San Francisco pay grade while working from Omaha and just be flush with cash. There are companies that pay the same pay rate regardless of what your cost of living area is, but others will absolutely scrutinize where you physically live versus how much they’ll pay you on a sliding scale. As mentioned above, how specialized you are will determine how much leverage you have in these negotiations, but just know that with all else being equal, “expensive” employees that are redundant are always the first to be let go.

You might consider negotiating a more dynamic compensation package where you don’t require as much cash as your salary and can earn more up front or based on performance in equity, bonuses, more vacation time, etc.

It’s Still Work

As is true in any job, the more you demand of your employer, the more you’re expected to add value. Over a long enough timeline, people who slack off from their responsibilities get noticed in ways they’d rather not. Just because you don’t have a manager physically peeking over your cubicle to see what you’re doing, doesn’t mean you should take advantage of the freedom you have. Moderate your expectations for what you need and want from your job and your employer will likely reciprocate. I’ve taken on lesser paying jobs that I had an absolute blast doing. Of course I enjoy making a good salary, but I’ve negotiated up my pay aggressively before and have seen others do the same to me when I was a startup founder - there’s a diminishing rate of return.

So, if you love where you live or simply want to avoid going to an office on a daily basis, realize that technology has made it so much easier for many (not not all) professions to be remote. Just ask yourself and whether you’re made out for it or not!