I found both of these posts and realized that I have also crossed a decade of remote work recently. 99% of that time was spent working for myself with no official “boss”.

Let’s pull some highlights, first from Tom’s article.

It takes a certain type of person to be able to work remotely for long periods of time. Are you comfortable in your own company? Do you enjoy putting everything into a specific task for a few hours? Can you do that without being distracted? These are the sort of questions I ask people when I’m quizzed about remote work avenues.

Are you that person? Can you focus or do you need someone else to set deadlines for you? What about interaction with people? Do you need a bunch or not much?

At one point my wife worked from home alone, and she needs lots of contact. Then I’d come home from a construction job and she’d want to go out and enjoy the hot sun with me, but I just spent the day sweating in the sun. It was not the best arrangement.

Whether you’re working from home or on a beach, you need to be productive. This can only happen with periods of intense focus in my opinion. Remote work often does not lend itself to this.

I disagree with Tom on this one. You’re at home you have the option to not answer the phone. No one can swing by your desk to “chat”. You just have to be focused instead of only thinking about the freedom that can come from working at home.

Put your phone on do not disturb. Use an app to mute social media. Get the game consoles out of your office.


A common attraction to remote work jobs is flexibility. No one looking over your shoulder, make your own hours up as long as you get the work done, go for a pub lunch, take an early finish if you need it.

Flexibility is a definite perk, but I’m also a firm believer in baselines routines. What I mean by this is how a standard work day should typically go.

I work from Starbucks the same day at the same time every week. I do the same tasks there every week for the same clients. Routine is awesome.

Remote workers often miss out on the end of week drinks and the Christmas parties. So with that said, extra effort is usually required to be social.

I try to head out every Friday afternoon to talk with people that I like. Coffee with a friend is awesome.

As a remote worker with a home office, there is always that temptation to carry on working. It’s like reverse distraction.

It took a while for me to stop heading back to do just one more thing. Now my wife can’t remember the last time I worked on a weekend or headed back to the office at night for a bit of work. Conversely, vacations are still a sticking point with us. I don’t do those well, yet.

Now to Viktor, which Tom’s post above pointed me to.

The first thing that I would like to point out is that remote working is not for everyone. Over the years, we have had a few team members that could not work remotely. In some cases these people discovered this themselves and chose to leave, and in some other cases it became clear that it was not a match.

I worked for a big WordPress agency, as employee 6, and found out that I was a terrible employee. I discovered this and initiated the call to figure out how I didn’t work there anymore. It wasn’t the remote part, it was the boss part for me.

Hiring remote means a larger talent pool. I’m hardly the first to point this out, but one of the major reasons why it makes sense to be remote-only. You are no longer limited to hiring in your geographic area.

Can’t count the number of times an interesting opportunity has come up but they say I have to commute to Vancouver (at least an hour each way if traffic is good) or worse, move into the US to some big tech area. Hard nope on both of those, not worth the life trade-off.

If I commute to Vancouver, I don’t get to see my kids. Way too much paperwork to move to the US.

Perhaps not related to remote work itself, but more the startup culture. VC used beat it in to young and naive early 20-something kids that it was cool (and even expected) to frequently pull all-nighters and sleep under their desk. I feel like the tide has finally turned on this.

Have I mentioned that I finish work at 3pm most days of the week and hang out with my kids. I have about 6 working hours a day and I focus on work during those hours. The rest of the time is for running, and family.