For us mere mortals who still have to slave away at work – instead of living off of our investments – the idea of working from home can be incredibly enticing. You get to relax, hang out, do things around the house. Nobody’s looking over your shoulder asking you about TPS reports. You don’t have to pretend to care about office gossip. Pajamas are semi-acceptable attire for the first few hours of the day.
But the truth is, working at home is seldom as glamorous as it may seem. For some people, it’s an awesome arrangement. For others, it’s a fast path to failure. Where you land on the spectrum will depend on a ton of different factors.
How I Asked to Work Remotely
I’ve got a bit of a history with working from home. When I was at my first company, I had taken a position that required me to travel to California (LA area). I was working with six offices out in Southern California. In order to give them the time they needed, work was flying me out to Hermosa Beach for a week at a time, two weeks a month. (Check out that link for where they’d have me stay and try to tell me you wouldn’t want to live there, too!!)
Half of my time was spent in California, and I started to think about moving there full-time. Sure, the travel was nice – and work paid for my food so that was a plus – but after a year of doing it, it was getting to be exhausting. Besides, living there all the time seemed way better (and it was).
I knew I had a good argument for me moving there full-time. The offices I worked with loved having me there, and putting me out there full-time meant I would be able to help them more. I wouldn’t have to worry about catching a flight. Coming to an office two or three days in a row wouldn’t inconvenience other offices as much.
So, I asked my boss if I could move. I cited things like reduced travel expenses, increased productivity, and the fact that it snowed in May as the catalyst for the request. He agreed that it made sense, and requested we set up weekly check-ins and quarterly visits back to Minnesota.
A few months later I drove out to California with whatever I could jam into my Hyundai Sonata. It was an awesome trip.
Not even a month after moving, I got word that the structure of our team was going to change. Instead of focusing on pockets of offices, we were going to tackle larger customers and overall company processes.
My time I was planning on spending at many offices now was dedicated to me sitting at a desk in one office (coincidentally where Kristin happened to work). And let me tell you, I didn’t love it.
I wasn’t working with anyone in that office directly; it just happened to be the closest to where I lived. Slowly but surely I cut back my hours at my desk and started working from home for half days, then full days.
Eventually, a few months after moving, I didn’t come into the office hardly at all – maybe once or twice a month. Thus began my 2-ish-year Work From Home stint. In that time I learned a lot about what I liked and didn’t like. I was able to figure out what I needed in order to successfully work from home, and how I wanted future remote opportunities to pan out. Here are the big ones:
The Good Part of Working From Home
There are some great advantages to working from home. For me, three things really made the difference.
Ah yes, the office attire. Business casual is a thing of the past when you work from home. It wasn’t uncommon for me to work in my PJ’s for half the day, shower over lunch, and then wear shorts and a t-shirt in the afternoon.
If I’d kicked off my career that way I could have saved a bunch of money on clothes. But even so, it helped us keep our closet pretty organized. It also made it really easy to shop – one of my least favorite activities.
PJ’s may not be appropriate for everyone, but you can definitely be more casual at home. On my first team, we had a joke about one of the developers we worked with who lived and worked in Michigan.
Nobody ever saw him. He never did any video conferences or anything. We’d always joke that he would show up to the Christmas Party naked because that’s what he wore to the office! Hahah, maybe don’t be THAT casual, but you get the idea.
Taking a lunch break or just a coffee break when you’re working in an office kind of sucks. Sure you can maybe go for a walk, but most of the time you’ll get odd glances and maybe not even take frequent breaks.
When I worked from home, not only was it easier to take breaks, but they were also more productive. I could easily switch around laundry or pick up a few things around the house. I could walk down to the beach and just hang out for a bit, or even go grocery shopping.
I did have to keep an eye on how many I took and how long they were, but overall, breaks seemed much more satisfying when you can really do whatever you want on them.
Easily the biggest and best improvement when you work from home is the elimination of your commute. If you’ve got a 30-minute commute each way, that’s a full hour of your day you get back. Add in the fact that your morning routine is likely simplified from not necessarily having to shower every day, and you gain some extra sleep.
In the afternoons, I could unplug at 4 and work on something around the house, run errands, or play video games at 4:01.
Having no commute was great, especially in California! I also saved money on gas, obviously. We’d planned on going down to 1 car if our situation had stayed the same. Obviously it didn’t, but it’s a lot easier to do that when one person in a two person household works from home.
There were definitely other benefits, but those were the big ones for me.
The Bad Part of Working From Home
Of course, not everything is rainbows and butterflies. There were drawbacks at times that made working from home difficult – and sometimes downright impossible – that were just really challenging for me.
While I’m very much an introvert, I still need some degree of social interaction at work. In particular it’s helpful to really get to know the people you’re working with, and build that rapport. Nothing quite does it like face-to-face interactions.
I found a lot of times that offices would still ask me to come in and help them. It was so much easier to do some things in person with my undivided attention compared to remote. Being able to read facial expressions and body language made it easier to communicate.
And quite honestly building those friendships can be fun. Going out for the occasional beer or three can make working more enjoyable. I missed that social interaction at times.
This is where some people will have the biggest challenges with convincing their employer to let them work remotely. When you’re at home, there are constant distractions.
Remember those breaks that were great for laundry? They’re great as long as laundry doesn’t turn into laundry, vacuuming, dusting, going grocery shopping, cleaning out the fridge, and mowing the lawn.
It’s really easy to get caught up watching Orange Is The New Black over lunch. Suddenly my 1 hour lunch break turned into Netflix telling me “Dude! Get off your ass, it’s been three hours. You still alive?” Ah, crap.
Minimizing distractions however you can is crucial. Having a dedicated office would have helped immensely. My work was a bit slow so this didn’t actually significantly impact my output, but it definitely would have if I’d been tasked with more things.
Every now and then I’d get in the zone with something I was working on toward the end of the day. I’d continue working on it even past when I “should” have.
It can be really tough to totally disconnect from work when it’s RIGHT THERE. You might seek out a better work-life balance, but actually find that you achieve the opposite.
The same thing holds true for the mornings. Roll out of bed and on the computer within 20 minutes. It made for long working days that, while productive, could become exhausting if unchecked. Setting an alarm sometimes helped me check this.
If you are the type of person who gets consumed with their work, you’ll need to keep an eye on this. To be honest, though, it’d probably be better to be consumed with work at home as opposed to being in the office all night. That’d be my preference, anyway.
Working from home is definitely not for everyone. It takes a special kind of person to be able to do it successfully. Part of the reason employers are hesitant to offer it is because they understand this.
How To Ask To Work Remote
If you want to start working remotely, the best advice I can offer up is to not only be a rockstar, but suggest you do so on a trial period. Make sure you have sound reasoning for requesting to work remotely. Sure, it may be to achieve a better work-life balance, but add more to the story.
Productivity is the biggest thing most employers care about. When you ask to work remotely, productivity will certainly be one of the biggest concerns. You need to make your boss feel comfortable that you’ll still continue to produce good results.
The best way to do that is to recommend a trial period. For 4-6 weeks, work remotely for 1-2 days a week. Make sure you stay productive at home, and check in with your boss every week. At the end of that trial period, if things go well, either continue or add more remote work time.
If they don’t go well, respect your employer’s decision to have you back in the office full-time. It may suck, but unless you can prove you’re not going to let things slip, you can’t expect much.
When you can work remotely, as long as you can keep that good work-life balance in check, avoid distractions, and are okay with a bit less social interaction, it can have some great benefits to your overall well-being.
And the worst that happens if you ask is they say no. Then you’re in the exact same position you’re in, anyway.
Have you ever worked remote? What were some of the pros and cons you found from your experience? If you haven’t, do you want to?