3 Things I Loved About Working From Home (and 3 Things I Hated)

Working from home lets you drink your coffee in a real cup!

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.

Everything Changes

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.

Social Interaction

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.

Constant Distractions

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.

Can’t Disconnect

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?

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  1. Well! I’m working remotely right now (and taking a break–not slacking, y’all). I LOVE working from home, but it definitely can be isolating. Sometimes I only leave the house once a week to go get groceries, and that’s it. My team has near-constant Hangout meetings, though, so I talk to people plenty throughout the day.

    A BIG component to working remotely is having a dedicated office space that is just for work. It’s much easier to disconnect that way.

    And yes to the breaks! My breaks are so much better now. Instead of staring at the coffee pot in the break room, I can load the dishwasher or sit on the porch for a few minutes to enjoy the sunshine.

    And you know what? I’m actually MORE productive working remotely than I ever was in an office.

    1. Haha, I laugh at your ‘I only leave the house once a week’ comment because I was the exact same way! Except mine was to move my car from one side of the street to the other because of street cleaning LOL.

      The productivity thing is a big hit-or-miss I think – it all boils down to the person. I think that the bad apples give the rest of the hard-working folks a bad name sometimes, which is why companies may be hesitant to allow their people to work from home. I’ve heard from a lot of people that they’re more productive working remotely, but that’s definitely not the case for everyone 🙂

  2. I recently started working from home one day a week and I really like it. One day is enough for me as I don’t seem to be as productive after a few days. I get too distracted with everything that needs to get done. The best part about working from home for me is to avoid the commute and to be able to take my dog for a walk at lunch when it is still day light.

    1. Yeah, it’s easy to get distracted a lot. Even if you have a dedicated office sometimes it can be tough. There’s always something calling. 🙂

      The commute was easily the best thing for me in CA, and would be here, too. In fact, if I ever ask my boss if I could work from home that’d be the main (only) reason. The extra drive in the morning doesn’t bug me one bit, but not having to deal with afternoon traffic on a Friday would be great.

  3. Sounds like you have a great set up with work! I think that working from home will be very difficult if you have kids (though it can be a major draw).
    I work from home a few times a week and really like it though you’re right it’s hard to disengage- sometimes I am working overtime without knowing it. I find the small chit chat around the office a waste of time (15-20 minutes of chit chat) though I’m also much of an introvert as well.
    Currently I am on maternity leave so I’m ‘working’ from home with my blog hahaha.

    1. I’ve worked with a few people who had babies and worked from home. I can tell you that sometimes it worked out great, and other times they were not productive at all, would miss calls, etc. Just not the type of situation you’d really want to be in when working from home. It started to frustrate others on our team as well.

      Maternity leave is a great opportunity to work on your blog more intently if you can! We won’t ever have that experience, but I’ve often thought about taking a couple month sabbatical to focus on the blog 🙂

  4. After over three decades of corporate work in an office I now do side gigs from home in my retirement. I agree it is nice wear shorts, take fun breaks and in my case to pick which 8 to 16 hours of the week I decide to work, or decide not to at all. I’m on my screened in back porch right now, it’s 68 degrees and the birds are singing as I look out at 800 acres of woods. It is really quite nice!

    1. Aw man that sounds awesome 🙂 Once we pay off our house, even if we aren’t in a position to fully FIRE yet, I’d love to cut back my hours and consult for ~24-30 hours a week, giving me the flexibility to focus on some other things as well. That’s pretty much how I envision retirement, really…at least a little bit of consulting work here and there to keep my brain engaged, but ideally almost all remote work would be nice.

  5. Thanks for posting this Dave, totally resonates with me. After doing contracting work with a bank here in LA, part of the negotiated perk is being able to WFH, and being that you’re familiar with LA traffic, being able to not be in it 3 times a week is a huge win, that of course if you avoid the exact pitfalls above, being in the zone, distractions, etc.; you totally hit mark on this. Bottomline, as long as we meet our deliverables, we’re good 🙂 So I still enjoy WFH 3 days a week but as you know it gets old, it helps for now though since i’m paying off debts and can use the savings 🙂

    At any rate, keep up the great posts man, really enjoy them and your perspective on life and finances.

    1. Oh man, not having to worry about LA traffic 3 times a week would be HUUGE! That’s awesome – great job on negotiating that. The key is you need to CRUSH IT on those 3 days so they know you’re still a rockstar. 🙂

      Honestly 2 days in the office though would still give me, at least, enough of that social interaction to not feel like I’ve become a hermit 🙂

      Glad you like the blog! Thanks for reading and for commenting, always nice to see a new face!

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