That remote lifestyle

Plan Your Next: Letter No. 11

Good morning!

I’m about to embark on a bike trip down to Long Beach and back this morning. It’s taken me too long to get the bike out and into the sun, but I finally got a tune-up and removed those fenders that aren’t needed here.


I’ve been working remotely for almost 4 years straight now, and all in all, I’ve worked over a decade from home or somewhere else, outside of the traditional office.

There is something special about working outside of a traditional office. The challenge though is to find a balance between having a dependable routine, and being flexible enough to find inspiration when you’re not really leaving the house as often.

It’s not for everyone, and much of the time it can become increasingly lonesome. To combat this, I’ve also taken several month long trips to work remotely, blending work and play as closely as possible.

When I first started out, I worked my ass off to get into an office. Years later, with equal effort, I worked just as hard to get out of the office.

If you’re at all like me, my most productive environment is where I can get a healthy dose of that Vitamin D, which is one of the reasons why I moved to the West Coast in the first place. My best work comes from sitting in front of a window, outside at a nice large table, or at home using my standing desk looking out at the flora through my windows.

I used to approach it in the complete opposite way, preferring to be in a dark room, shutting the office shades, hoping it would help me focus more. Working on your own is lonely enough, try doing it with the lights off!

In most instances, working remotely means you’re by yourself, having to find the motivation and the desire to push forward when you’re stuck, and hopefully have built in routines that you can fall back on, knowing what works for you.

My dad telecommuted for his company in the early 90’s, before internet access was a thing. I remember thinking then that working from home was the coolest thing possible.

Instead of having email to send files back and forth, he would drive to the office once a week with a floppy disk containing his design files.

His setup was considerably different, using a separate phone line and a fax machine to do most of his communication. He hardly used the phone, as scheduling conference calls with remote employees took a lot of coordination.

Currently for my day to day, I use HipChat and email for communication, Highfive for video conferencing, Google Drive for storing files in the cloud, and Jira for tickets.

Is it right for you?

It helps to have a clear understanding of who you are. If you get lonely, or get distracted too easily, it might end up being tougher than you might think.

There are also different dynamics at play depending on how the company is set up. I’m currently working with a team where less than 10% are remote, but have also worked on teams that are fully remote.

They both have their challenges, but the solutions are not all that different. Both still require that you over-communicate, and make sure you’re hitting your deadlines.

It’s much easier when everyone is remote, but I think you have to learn to be accessible and spell out your ideas so that you’re not assuming things are done. (I’m still growing in this area.)

How to find a remote job

It’s never been easier to work remotely, and according to a recent poll by Gallup, since 2005, there has been a 115% increase in the amount of U.S. employees telecommuting.

There are job sites that only show opportunities for remote workers, or freelancers, and so it’s becoming incredibly easy to seek them out. I think the biggest question is not how you can find a remote position, it’s rather: do you think you can handle working remotely? (Job links below)

What’s helped me

Communicate: I think this is always a work in progress (at least for me), but being available, being as literal as possible, and being dependable all help to make working with each other much easier to do. Slack or Hipchat are good tools to help with this.

Video conferencing: Our company has made a good effort to utilize video conferencing, especially for us remote workers. It helps to see a face, and make that connection. While it’s not always necessary, once to twice a week really helps to keep you connected to others.

Co-working: I don’t think it’s necessary, but if you’re working from home and find yourself getting lonely, then co-working can help blend the social side that you might find in an office, with the solitude you might find by yourself. Even using a lower tier “Hot Desk” option keeps the cost low, while providing similar access to a whole new network. I’m personally looking into my options out here in LA. But maybe starting a co-working space might also be in the cards?

Events: Force yourself to attend meetups or events that allow you to build your network. I think it’s dangerous to stay disconnected.

Staying healthy: I hate going to a gym, but I know that if I go to long without working out, my back can get out of whack. I have pretty good routines using just kettlebell swings plus some additional weights, and an indoor bike.

Desk: I have an electronic standing desk that is affordable and great looking. You can program different heights into the panel, so converting from standing to sitting is a breeze.

No TV: I haven’t owned a TV in over 7 years, and even though I still watch movies on my laptop, it’s helped keep my couch surfing at bay. Who wants to design their living room around a 50” black rectangle anyways?

Working remotely is a great way to find some extra free time in the day, but it really comes down to knowing yourself and whether or not you have the discipline to stay motivated.

If you’re considering it or have any questions, please reach out.

Have a great week!

Resources & job sites:

Here’s a question for you

Do you work remotely and have any tips? Or, do you have any resources for people who want to work remotely?


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