How to Work Remotely Like a Boss

Jan 22, 2016 · 4 min read

Everyone wants to work remotely, and it’s not hard to see why. Remote work is synonymous with freedom. The freedom from being tethered to a cubicle, the freedom from having to wear pants. It’s a life goal that a lot of us share because (whether it’s true or not), remote work seems to make work-life balance all that much easier to attain.

I’ve been working remotely for the past 18 months at Outside Magazine’s travel company, Outside GO. I’m nowhere near an expert on the subject, but I have learned a handful of things about working from afar. I’ve taken take full advantage of some of the obvious benefits (avoiding Sunday traffic back from the mountains! Folding laundry between emails!), but I’ve also learned a few of the challenges. Like how in addition to needing strong communication skills, you also need something often overlooked — a completely portable office.

Consider what you normally have in your space: a Thunderbolt display, maybe a printer, an external hard drive, some potato chips. Now strip it all away. None of that is coming with you to the beach bungalow, or even to your couch. The items below are what I’ve narrowed down to carry every day, and would recommend for anyone trying to hack the mobile lifestyle.

I’m a proponent of the written word. You know, the pen-to-paper kind. Every day I keep track of assignments this way. Because I’m going tactile here, I’ve opted for the leather-bound Bull & Stash notebook with a Karas Kustoms aluminum pen. This upgrade from a 10-cent ballpoint and spiral-bound notebook makes me look like I know what I’m doing, which helps with the fact that I’m wearing yoga pants.

Another necessity is somewhere safe to put my cash. The Bellroy Note Sleeve wallet is slimmer than any I’ve carried before, and is handsome enough to earn its keep. Lastly, I always keep a multi-tool handy so I can rip into boxes of gear or whatever comes my way. You never know when you’ll be the only guy in the room with a Leatherman.

It’s not the twentyfirst century unless you’re packing a laptop. I lug around the heavier option, a 15” MacBook Pro that I’ll be exchanging for something lighter on my next go-round. In order to captain the thing as efficiently as possible, I use an Apple Magic Wireless Mouse. Headphones are also tucked into my pack to drown out terrible tunes at coffee shops or to get in the zone in the middle of busy airports. Of course, the power cord commandeers a pocket in my pack.

The most important and the most difficult item to find for your roaming office is the messenger bag or backpack you’ll use to carry everything. I went through three (they basically all fell apart) before settling on the Lael messenger bag. It’s got leather reinforcement points and sturdy hardware, but most importantly, it’s not too big. That reminds me to keep my essentials light and lean, just the way I like it.

Building your remote work bag is an iterative process, and as you continue to fine-tune your tools, that same clarity will start to rub off on your work. Have a hard-earned tip? I’d love to hear it in the comments below. [H]

Whitney does marketing at Outside GO, loves donuts, and is a total endorphin junkie based in Boulder, CO.

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