Overcoming the Challenges of Remote Work

Overcoming the Challenges of Remote Work

Remote work is a fairly new phenomenon that’s rapidly changing the work world. We have companies like Doist, Discourse, and many others who are building 100% remote companies. Not only that, but we have more companies who are letting their employees work from home, and many self-employed people now work remotely.

Being “out of the office” introduces a number of differences from regular office work, from how days are structured, conversations are had with coworkers, and emotional health is maintained.

If you’re a remote worker in any capacity, I’m interested to know:

  • What’s the #1 challenge you’ve faced working remotely?
  • How are you working to overcome that?
  • Can we help you in any way through that process?

Reply below!


Great topic!

I work from home once a week and occasionally twice if it’s helpful for some reason. In the past I worked for myself and mostly worked from home - I thought I preferred that but it turns out I don’t. I like being in an office with people most of the time and only working from home a bit.

I don’t have problems with getting work done or motivating myself when I work from home, which I find people always assume is the case if they don’t do any homeworking themselves. Oh, you must find it hard to get anything done. Not so much actually.

My actual challenges are:

Getting really hyper-focused and finding it hard to take time out. I don’t really understand how this happens. In the office I’ll take five or ten minutes here or there to make the tea round or something else that gets me away from my desk, I can find the time and I often come back having done some background thinking on whatever I’m working on.

At home, time somehow goes faster and it’s weirdly difficult to take time away. I’ll want to get up and do something, and I just… won’t.

Accessing my stuff without friction. I don’t want to carry paper notebooks backwards and forwards, or be unable to work because I was off sick the day before my remote work day and couldn’t bring home my notebook.

At the moment my approach is to use a digital task manager and - because I do need/want to use paper for various things - have notebooks at work and home. Ideally I process all notes before finishing work for the day so I can just pick up any notebook next time I need one.

My next best solution is to photograph any unprocessed pages just in case I need them. I worry a lot about needing something I’ve left in the office (and wouldn’t want anyone else going through my stuff to send it to me).

I wish there was a paper notebook that synced to the cloud - if only!

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This is my NUMBER ONE challenge working from home. I sit down to work, then I… work. And work. And work. I find it harder to take breaks at home than at the office.

Are you finding anything that’s working for you to take a break when working from home?

Yeah this is a tough one to solve when you’re working technically from two offices. Digital is definitely better in this regard. I used to wrestle with this too, and finally had to land on digital.


Would the LiveScribe pen work for you?




Not yet. I haven’t quite figured out why I can’t do it! Definitely one to work on.

The pen is a cool idea but I would need two to solve my problem. I should have said I need two notebooks to sync to one cloud :rofl:

Thanks for the reminder that they exist though, I knew about them and had forgotten! It’s on my wish list for sure.

Edit: actually that would probably be easier to carry around than a notebook. It’s a great idea - maybe one day when I have the cash spare…

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What’s my #1 challenge?

My main challenges as a remote worker for the last 7 years have been varying depending on the role I’ve had.

The first company I worked remotely for was not a remote-only company, meaning not being in the main headquarters left me feeling I was missing out on something. It was a lot harder to stay connected and get a word in edge-wise on meetings when most people were located in the same room.

My main challenge now working for a remote-only organization is the social aspect of work. I’ve adjusted to this OK, and it really helps having my family at home when I work. I never thought I’d say this but I get really lonely when my family is all gone for the day.

How am I working to overcome that?

I try to maintain regular lunches with friends and the like, but it’s still hard. I’m in my 30s with a young family, as are all my friends. So that gets challenging to maintain due to schedules and everyone being “busy”.

How can the community help me through this?

I like that we can have conversations about productivity here. Probably keeping me accountable to having social time though too! Digital relationships are great, but you can’t live off them alone.

I’ve been working exclusivelly remote for 12+ years, and for the most part it works great.

But to answer the question of hyper-focus, in my experience it’s because of two things.

1. Notifications

When you work remotely you feel like you need (or have been asked) to prove you’re always there. This comes from working with old-school managers that need proof of work (tracking hours, seeing you type at your desk, etc.).

That in turn creates fear of not missing any important emails, messages, etc. which makes you stay in your chair longer than you should.

2. Time management

What works for me is to block time for work AND time for other tasks, like lunch, or coffee, or breaks. So I would write them down in my bullet journal and have them in front of me all day.

It’s innevitable that you gloss over the journal and notice you need to take a break.

Two things that make it easier

It helps if you have a social group to share those breaks with. It helps you unfocus from work tasks. So you might have coffee with your family, or share a co-working space. Whatever works for you.

The second thing is to take work less seriously. This might come easier the more experience you have, but in general, feeling confident in your expertiese allows you to give fewer fucks about bossy colleagues/managers and helps a lot with stress and anxiety (which is another very important aspect of working remotely).

I hope this helps. And feel free to ask anything.

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My Samsung Gear S3 watch does a great job of bugging me to take a break, get up, stretch, etc.

Cheers! That’s been my finding too.

I agree. When you’re remote, all work is digital, therefore, all work for the most part is available at your fingertips at any time of the day. Trimming notifications plus setting good boundaries is key to not working all the time. I’m finding I struggle with this since I changed roles, actually, since the culture is different. It’s really odd when you realize that your coworkers work across all time zones so someone is working at any point of time!

I’m glad this works for you. Unfortunately I can time block all I want but unless something holds me accountable to it, I have a hard time maintaining it myself. [quote=“chalmagean, post:8, topic:5065”]
The second thing is to take work less seriously. This might come easier the more experience you have, but in general, feeling confident in your expertiese allows you to give fewer fucks about bossy colleagues/managers and helps a lot with stress and anxiety (which is another very important aspect of working remotely).

All I can say here is, “Amen!”

Welcome @mtrifro! Great! I used to have an Apple Watch and I got desensitized to the standup taps every hour after about a year of wearing it. Glad this works for you though

Interesting topic for sure!
I work from home 3 days a week, and am in the office other other 2 days (2 hour commute each way).
I work for a company that have been quite happy for people to telecommute. I have colleagues who haven’t been into an official office for over 5 years, but are still the person that everyone knows, who will give jobs to if they want to make sure they are done, etc etc. He fits that in around dropping his kids to school and picking them up/making dinner (his wife is up at 4:30am every day to commute), and when he’s done with dinner, his wife’s usually home, and he heads downstairs for another few hours of work…

Having a dedicate working space is crucial I have found… If you don’t, its too easy for work to encroach on your personal time. I’m still bad at making time to do exercise, etc (3 kids under 5 makes it hard to do that outside of working hours), but due to a health scare that happened earlier this year (and another one that happened a week or so back), I’m being more strict and making time for me…
I have a sit stand desk, and nabbed one of the office chairs that was being thrown out because the material was torn on it, so I have a decent chair, decent desk… Just working on seeing if they’ll get me one of the new 30" 4k monitors that I’ve just had put on my desk at the office, for home… :slight_smile:

What’s the #1 challenge you’ve faced working remotely?
Without a doubt its switching off, or taking time to just get out and do some exercise, when theres people who are in the office that will go down the gym every day…

How are you working to overcome that?
Due to the health scare, it’s forcing me to change my priorities. I want to be around long enough to be a nightmare for my kids when they have children of their own, so I’ve taken stock and am working on getting healthier.

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This is the beauty of having flexible work hours for working remotely. It’s so much easier to take care of life stuff when you’re not chained to a desk at an office hours away. Or in the case of your colleague, help family out when your spouse is in that boat.

Yeah this is true. You do have to have really good boundaries if you don’t have one. And even so, the smartphone can suck you in if you’re not careful.

I’ll be in that boat soon with 3 kids under 5. I’ve been trying to take thinking breaks in the afternoon where I go for a walk, but that doesn’t fix sitting at a desk all day, either. It’s a tough problem to solve, especially on a limited time budget.

Feel free to create a topic under #personal-updates if you want to bring us along on the journey! It encourages all of us and can be a way of holding yourself accountable. But no pressure there, either!