Mark Loveless, aka Simple Nomad, is a researcher and hacker. He frequently speaks at security conferences around the globe, gets quoted in the press, and has a somewhat odd perspective on security in general.

Working Remote

Working Remote

Photo by Dylan Gillis on Unsplash

I’ve been a remote worker for two decades. I love it, and cannot stress how awesome it is.

A bit of background. In 1999 I left my job at the railroad as an infosec guy and went to work for a Houston-based company. This company had a security research position open, and the security research department was located in Framingham, MA. I had the choice - I could move to Framingham, or for a slightly lower pay rate be remote and work from home.

As most IT professionals from that decade will tell you, working from home was fairly common for the on-call person, because no one wanted to drive into the office in the middle of the night. And many security people back then (mainly the infosec pro by day, hacker by night crowd) kept weird hours, so often being a remote security worker meant you would be up and online in the middle of the night working, in part because you were in a groove and were just enjoying the hell out of your job. Having worked for large corporations and small startups, software and hardware vendors, the security folk were usually specialized enough that you could get away with working from home.

So once I took that first remote job, I decided that was it. I've haven't worked in an office since. I am on my fifth remote job, and this fifth one is the best one yet since the entire company is remote. Any future jobs will be at all-remote companies.

Of course there are pluses and minuses working remote, so for you sad office workers I've listed them for you.

Advantages

Some of these are well documented at other places on the Internet, some are obvious once you think about it, and some are from personal experience.

  • Able to handle weird home-based events. The freedom to get up and answer the door to let in the repair person instead of having to take half a day off (or longer) is amazing. Being there to give that signature for that expensive thing you ordered online is also amazing.

  • You can handle sickness easier. Kids home from school due to illness? You don't have to take a day off, and the older they are the easier it is to care for them anyway. As for myself, I've worked when ill because I wasn't that ill, just doped up on cold meds to the point I shouldn't drive. It does make for a good day to work on documentation.

  • Emergency errands. Out of cold medicine? Need to go pay some random last-minute bill in person for whatever reason? Much easier.

  • There is no commute. You save on time in traffic, gasoline, wear and tear on the car, and so on. No tolls, no parking fees, no tickets for speeding because you're trying to get to work for a meeting or home to meet the cable company before they leave and reschedule. Leaving all of that expense behind is a pay raise in itself.

  • Smaller carbon footprint. It doesn't matter whether you're into saving the planet or not, when you are commuting your vehicle is polluting (unless it's electric). But either way you can brag about how much you care about protecting Gaia and look down your nose at others and be all righteous and shit, because you have substantially reduced your carbon footprint. Sure, if you really cared you'd have a metal straw and spork for your visits to that vegan eatery and you'd go the whole nine yards, but this way you can say you're doing your part and can rub it in other people's faces - all from the comfort of home.

  • Nearly unlimited comfortable seating. If you decide you want a change of pace, you can grab the laptop and head to the couch or your favorite chair or the back patio swing. Or go to Starbucks or some other place that has beverages. Hell, you can head to a bar that has Wi-Fi, start ordering adult beverages, and relaxingly type in commands as root. All in complete comfort.

  • No pants. Everyone makes that joke, but it is true. Trust me, I work at an all-remote company. Every person there has hopped online at least once with no pants, or at least clothing choices that would not even begin to be acceptable for the most casual of "casual Fridays". Personally I do get dressed but only because I don't want to freak out the various delivery drivers or post office personnel that show up at the door.

  • No after work "bonding". You do not feel obligated to go to that after work visit to a local watering hole for a bunch of overpriced drinks.

  • Improved diet. If you wish to eat healthy, you have way more control over your food intake. No more "working lunches" or "team meetings" with least common denominator choices like cheap pizza or greasy burgers. I mean, you could still eat like shit, but you don't have to.

  • More productive hours. I remember being in an office and having people just walking up and starting a conversation about whatever, interrupting my work and throwing my thought processes off. Working remote you don't have that problem.

  • Instant excuse to leave early. If you’re at some dinner party and the host is getting ready to start on one of those “you’ve got to see these local news blooper videos, I have links to HOURS of them” marathons, you can look at your smart watch or phone and say “Oh no, <insert region from other side of planet> is having issues, I have to go. You know that remote worker job? Yeah, they need me, kthxbye.”

  • Office visits can be special. If there is a home office and you come visit for a week, you can often expect some type of outing that you don't have to pay for. You head out to the bar and half the team buys you a drink. Maybe some new movie came out and since you're in town the boss decides that the new Star Wars film would be an excellent team building event, and bingo - free movie!

  • Invest in a stable home. Not moving for a new job every three or four years means you can pay off more of your mortgage quicker, and if you take those bonuses and cost of living raises and apply those to the back end of the loan, you can pay off your house. No rent or mortgage!

  • You can travel and still work. There's van life, there's working vacations, there's all kinds of opportunity. Your spouse wants take the kids and go to California to visit family for a week? Go with them and work like normal, you're just doing it from a different timezone. Want to attend that concert in a town 5 hours away? Drive down, working in the car while your significant other is driving, get a hotel room, and go to the show. Work on the way back.

Working while I was also getting a flat tire fixed. I even had a thermos of iced tea with me, so I was all set.

Working while I was also getting a flat tire fixed. I even had a thermos of iced tea with me, so I was all set.

Disadvantages

Everything has a trade-off. Some of these are conditional, but nonetheless a bummer if they apply to you.

  • Missing out on impromptu meetings. This is one of those conditional ones. If you work remote but there is a home office, sometimes you miss out on impromptu hallway or lunchroom meetings and a decision is made - and if you had any input to give, you missed out.

  • Passed over. Again for the remote worker not in the home office, since you're not physically there you're not being noticed as much. This means you'll sometimes get skipped on sweet work assignments, passed over on promotions and raises, and so on.

  • Office visits can suck. You arrive at the office for your quarterly or monthly visit, and you get to sit wherever there is space, like if someone out on vacation, or maybe there is an open spot at one of the three “visitor” desks. You could camp out in a conference room until you were kicked out for some meeting, or just set up in the lunch area. It won’t matter, you will not get any work done because all of your friends at work you don’t see in person every work day will find you and want to catch up. Yes that can be fun, but if you’re expected to actually get work done, you’re going to end up doing it in the hotel room that evening when you have a few hours to yourself.

  • Stealing office supplies. I've made this joke before, but if you work remote it is way harder to steal office supplies. Seriously. Office Depot presses charges, the losers, so you can’t steal them that way.

  • No treats during meetings. If you're remote and you video conference in for a lunch meeting, you get to watch all your co-workers eating in the conference room while your stomach growls. Or Alice brought in donuts and Bob brought in breakfast tacos, you get to watch them fight over delicious pastries and snacks while you sit there in your t-shirt and pajama bottoms, nursing a cup of coffee with no cream because you forgot to go by the store last night. I did have a boss that actually looked up every remote employee’s home address that was attending a department meeting, and he surprised the few remote workers by having a pizza delivered to each of us, so we could actually join in, but that is extremely rare.

  • Timezones are forgotten. The team meeting at the office was moved from afternoon to early morning, so you discover you'll need to be up and online at 6am in Seattle to conference in for the 9am Boston meeting. After you struggle to get up, you get online at 5:55am only to discover they moved the meeting back to the afternoon.

  • Out of school. If your children love being loud and obnoxious assholes during the summer break from school, well, you get the picture.

  • School fundraisers. Speaking of children, selling fundraiser candy or Girl Scout cookies becomes much harder, because you can't take a pile of sweets to work and with a simple office memo unload the lot. Nope, you're going to have to walk around the neighborhood or hang out in front of Walgreens with complaining kids.

Fun Tips

Here are a few random tips and tricks for the remote worker.

  • Change jobs. If you really like working remote, work for an all-remote company. This eliminates most of the disadvantages above, except the office supply and children issues.

  • Befriend a barista. Running down and working from the coffee shop is nice. However there is always the danger of sitting there, downing beverages, filling your bladder, and needing to visit the restroom. During the restroom break, someone could steal your laptop. Instead of shutting everything down and taking the laptop with you into the toilet like some kind of weirdo, get your befriended barista to physically watch over it. It does require effort to befriend though - a combination of both tipping and actually being a friendly and engaging human being for more than five seconds at a time seems break the ice. Side benefit, you've made a cool friend. Same goes for waitstaff at a restaurant you frequent. To this day I have really good friends that I first met when they were waiting tables or pouring coffee. We've even vacationed with them, and some are as close as family.

  • Mobility. Being mobile is key to working remote. If you can work from home, then a coffee shop or doctor's office waiting room should be a breeze. Don't worry about Wi-Fi - in fact get an unlimited data plan on your phone and tether. It's safer anyway. About once every couple of months I'll run into someone playing around with hacking tools at the local coffee shop, messing with the Wi-Fi. This is especially true at the Starbucks near the local university in my town. So learn to tether. Additionally, carry a laptop or at least a tablet with a keyboard with you. You can be out to lunch or on an errand and someone needs something pronto. I’ve pulled onto the side of the road or into a parking lot and tethered, updated, and sometimes immediately solved the problem at hand. Less work for you later, the people on the other end are pleased, so it is win-win.

  • Clue in wait staff. If you're out to eat during lunch but need to get back to work in a timely manner, let waitstaff know when you order. I mean you're wearing a death metal band shirt, cargo shorts, and cowboy boots - you don't look like you have a job to get back to. This way the snooty business suit losers who have to go back to their sad cubicles don't get all of the timely attention of waitstaff and you can get the check quickly. For me, I go out to lunch with my wife nearly every day. Since i have grey hair, often wait staff assume I am retired. Like I said before, you befriend people, they get to know you, but you clue them in. Sure, no one is going to complain if your lunch is 65 minutes instead of 60 because if you’re keeping on top of your game no one will care. But still, you don’t abuse it. Just remember to be nice to wait staff and tip well.

  • Calendar up to date. A good friend of mine gave me a great tip - keep your calendar up to date. Block out time on your calendar for your lunches, what your normal working hours are, and make sure you block out appointments to things like the dentist or doctor. It really helps preventing a few of the less urgent items your co-workers need from interrupting you.

Quick Funny Remote Stories

Fun things sometimes happen that are related to working remote.

  • At one employer, we were on a conference call, and the boss was telling our team some weird explanation about a new and somewhat controversial company policy. Some of the team was in a conference room in the office with him, the rest of us were remote. He was trying to convince us it was going to be okay. Now we had a private company IRC server and a team channel and all that. Using IRC, a fellow remote co-worker sent me a private message asking me "do you think he's full of shit on this one?" Before I could answer him, several co-workers including my boss started laughing. By accidentally typing a period instead of a slash, the private question went to the team channel, and everyone including my boss read it. Fortunately our boss was wicked cool, and was completely ok with this.

  • I was in a team meeting during one of trips to HQ where all of the remote employees joined the rest of the team that worked at HQ for various meetings. During one part of the meeting our boss made some comment, and at this point I don't even remember exactly what he said, his comment just meant that the meeting was going to last longer. This was something that happened frequently enough that I knew from what he said the meeting was going to delay lunch. Very loudly, I let out an exaggerated and eye-rolling moan out of habit. The room went immediately silent, and everyone including the boss was staring at me. I said, "oh, sorry, I'm used to being on mute."

  • Finally, a quick office supply story. I was complaining on one of the work IRC channels about not being able to steal office supplies except when I showed up for meetings in person about once a quarter. The office IT guy saw this, and the next day I received a FedEx from the office, and when I opened it out came about a hundred ballpoint pens. I have no idea how much this cost the company, but he had sent it late in the day for early next morning delivery.

If you don't work remote, you're missing out. Trust me, totally worth it and I wouldn't have it any other way. And if you're already working remote but there is a home office you have to visit every once in a while, take the next step and work for an all-remote company.

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