At Postcard, we decided from the start that we would build the company and product as an entirely remote team. We loved the concepts of “working from where you’re happiest” and “killing the commute” (additionally, my co-founder may or may not harbour irrational feelings toward traffic ;)). We got a fair amount of feedback on this; as I recall, most fellow local founders thought it was a bad idea, while most potential hires loved it.

On the Internets, the battle for and against remote work has been well-documented: Marissa Mayer calling all Yahoos back to the offices versus Basecamp literally writing the book on remote work, among much other discussion.

I’ve come to the conclusion that this is a false dichotomy. Firstly, one person’s (or situation’s) advantage is another’s disadvantage (e.g., being alone for long stretches may be incredible for programming but terrible for bouncing ideas). Secondly, apparent disadvantages could be advantages in disguise (e.g., communication has to be mostly written and therefore verbose, which is slower, but thereby less likely to be misinterpreted and can more likely be reused).

Let’s look at a (non-exhaustive, based on personal experience) list of tradeoffs of remote work, peppered with reflective questions to ponder – then you decide which of them are positives or negatives for you.

Tradeoffs of Remote Work

  • Lots of potential for uninterrupted, productive alone time
    • Am I happiest working alone?
  • No commute (consider the impact on the environment, also, sanity)
  • Constant potential for change of scenery (work from a coffee shop, a co-working space, a friend’s place, etc.)
  • Can get lonely
    • Do I need in-person social interaction with my co-workers? Do I have other local people that I can fill this need with? Is it enough?
  • No opportunity for effortless serendipitous water-cooler or hallway conversations (though tools like Slack are making this marginally easier, with the added side benefit of murdering intrateam emails)
  • Collaborating around a whiteboard is much more difficult – in fact, collaborating in general is much more difficult
  • No instantaneous “tap on the shoulder” interactions
  • Much fewer emotional cues through body language or tone of voice
  • Verbose, and mostly written, communication is a must (along with tools to enable and manage it)
    • Can I convey my thoughts as well in writing as I can face-to-face? Am I as convincing, and understandable?
  • No absolute requirement to take time off if you need to be present at home (e.g., awaiting a delivery)
  • No beer o’clock with coworkers 🙁
    • Do I still love my coworkers sans beer?
  • Potentially easier to run errands at non-peak times (e.g., going to the gym or doing groceries at 10am instead of 6pm), though this is bleeding a bit to results-oriented work environments, not specific to remote
  • Face to face interaction still seems be tough to beat or even emulate for humans 🙂
  • Much higher need to be a self-starter (no team inertia to start work, nor social pressure to get you out of “PJ mode”)
  • More difficult to establish mentorship relationships for very junior employees
    • What is my skill level? Do I have what it takes to be productive on my own?
  • Higher levels of trust (again, social pressure to do work is or to appear to be doing work is gone, as is the ability to micromanage)
  • No need to pay for a co-located office for everyone
  • Potential costs of getting people together face-to-face
    • How much do I want to travel for work? Even once or twice a year?
  • Could be more difficult to separate work form non-work
  • Virtually unlimited talent pool
  • Building and maintaining culture and personality require conscious effort (though this may be an axiom of successful culture-building in any environment)
  • Modalities of communication require thought (is it better to write a detailed doc, to have a quick text chat, or to jump on a video call?)

I love this quote from a post on the Internet by Wade Foster, co-founder and CEO of Zapier; I just had to include it in my… post on the Internet:

One of the beauties of a remote team is that because remote work feels more like an experiment everything else feels like it can be more experimental too. So go ahead and experiment! The biggest wins aren’t usually found in a post on the internet, but in what you discover on your own.

Remote Companies

While still few, there are companies of various sizes making remote work for them. Here’s a sampling:

For a more comprehensive collection (though based on job posting activity within the last 90 days), check out this list by RemoteOK. The folks at Teleport have also put together a crowdsourced spreadsheet of companies that are distributed across multiple locations (though not necessarily remote).

Finding Remote Jobs

Traditional job search sites (like Indeed or Monster) are stuck in the <title OR keyword, location> paradigm. Thankfully, with remote work becoming increasingly popular, newcomers like The Muse and RemoteOK are catering their job search experiences to better match the mental models of today’s seekers, including searching for jobs by keyword (independent of location), by team or department, and by pay.

What Say You?

Are you all about the office? Or loving the remote life? What did I miss in the list of attributes above? Let me know, I’ll update the post with your contributions!

Over the course of the next 97 days, I’ll be interviewing people that are either looking for jobs, or hiring, and that are either all for remote work, or pretty against it. If you, or anyone you know would like to chime in, let me know! Shoot me an email to to let me know, or leave a comment below. I’d love to chat!

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