Skip to content


Escape From LA (Or SF, NYC, Seattle, or Austin): How to Know if Remote Work is Right For You

January 28, 2020
6 min read

Remote work isn’t for everyone. But in my experience, it’s highly possible that remote work is a better fit for you than you currently realize. There are also a lot of indicators that can help you predict this.

Backstory: I began my remote position as Very’s CEO after a lengthy stint in San Francisco (and before that NYC, and Hong Kong, and D.C.). All I wanted was to make enough money to move my family out to Montana to soak up drop-dead gorgeous scenery while skiing, biking, and running my heart out.

Then, I met one of Very’s co-founders, who asked me one question: what if you could have the freedom to move to Montana right now? My answer to this question is what started me down the remote path. I haven’t looked back since, but I’ve learned a lot along the way.

Here are a few things you should know about remote work to decide if it’s the right fit for you.

False Positives

First things first – let’s discuss the non-issues. These are common reservations regarding remote work and it’s normal to have them, but in reality, they don’t present as many challenges as you might think.

1. I’m too social, so I will miss the office environment. Not as much as you think you will, it turns out. I’m a social person myself, with a long history of people-facing roles in sales and leadership, but I thrive in a remote environment. When it comes to remote work, the power of tools like Slack and Zoom cannot be overstated if you use them well. Turn your video on during conference calls. Don’t be afraid to joke around or connect with people via chat. Building a great, social culture requires some effort from you and a lot from your leadership team, but it’s more than doable.

2. I’m not a programmer. Neither am I. In the U.S. alone, 97% of polled workers desired some form of remote work and they’re not all engineers. Common work-from-home job titles include everything from accountant to customer service rep to case manager.

3. I don’t want to take a pay cut to work in my pajamas. Fine, how about a raise? According to a report from OWL Labs, “Remote workers earn salaries higher than $100K/year 2.2x more frequently than on-site. We’ll also make drastic cuts to your gas bill and how much you have to spend on car maintenance. 

Quiz – Is Remote Work Right for You?

Okay, now, on to my Buzzfeed-style quiz. I’ve got green flags, yellow flags, and red flags you can check off as you go to help you decide if working from home is a good fit – or not.

Green Flags

These are really important. If you check off two or more from this list, keep reading.

1. The work motivates you. Anything worth doing is worth doing right. Which means heads-down focused attention. At a time when your mental acuity is maxed.

If you find that you are driven to be great at your craft (or at least a high performer), chances are the generic work environment someone else created, for 1,000 people who are very different than you, isn’t going to be ideally suited to you and that purpose. With remote work, you have the freedom to work the way you want to and drive great results in the process.

2. You don’t live in or would like to stop living in a large city. This one may seem obvious, but remote positions are ideal fits for non-major-metro dwellers. The modern, urban apartment is not designed for people to stay in for long periods of time. An 1890’s victorian farmhouse just outside Grand Rapids Michigan, much more so. And, as far as attractiveness to an employer goes, the Michigan candidate, who has clearly built a life around being remote, is going to appear to be – and IRL usually is – a lot more impactful in a remote role.

3. You have, or would like to build, a full life. One of the best aspects of remote work is the time you get back from eliminating the commute, the disruptions, the pointless meetings, the overly chatty coworker, etc. But not everyone values their time in the same way. If you drool over the idea of getting back 10 hours per week, you’re likely going to like working remotely.

Yellow Flags

These aren’t deal-breakers, but be on the lookout for these as potential warning signs that remote work might not be a great fit.1. Your spouse/significant other is an oak tree. If you have a spouse whose job cannot be easily moved, and you live in a major metro, you may not be able to fully enjoy a remote role (since, as mentioned above, remote work doesn’t always pair well with urban dwelling).
2. Your spouse/significant other already works from home. This is not a problem by itself, but proceed with extreme caution and make sure you both have access to separate, dedicated, workspaces.
3. Your home is less than 700 square feet per person. I will admit, I just made up this stat, but I’m willing to bet it’s pretty accurate. It’s critical that you have a dedicated workspace and that you’re not set up to go stir-crazy. It’s just more difficult to accomplish that in an NYC studio apartment than it is in something with a little more (literal) wiggle room.

Red Flags

If one or both of the below are true for you, it’s likely not a good time for you to go remote.1. You’re anchored in a major metro. If for any reason, you are in a major metro and unable/unwilling to leave, remote work is likely a poor fit for you.
2. Unsuitable dwelling/workspace. If you live in a place that cannot be made to reflect the key criteria below, and you can’t move, you’re likely to have a bad experience working remotely.

Remote Workspace Requirements

At Very, we style ourselves as Best Practitioners of Remote Work. While we have a full list of workspace requirements for employees, below is sort of a TLDR:

  • Dwelling:
    • Fail: Shared studio apartment
    • Minimum: Total dwelling size > 700 square feet per person
    • Ideal: Dedicated workspace that no one else can claim during working hours
    • Pro: A purpose-built home office, complete with a battle station.
  • Environment:
    • Fail: Windowless/low-light basement space or any public space.
    • Minimum: Access to a quiet space with a window and/or sunlight.
    • Ideal: Access to a patio or outdoors for breaks or change of pace.
    • Pro: Multiple workspaces that you can move between (e.g. primary battle station, patio, couch).
  • Connection Speed:
    • Fail: Unreliable connection or <10 Mbps up/down
    • Minimum: 10 Mbps up/down
    • Ideal: 25+ Mbps up/down
    • Pro: 100+ Mbps up/down and a phone set up to be a hotspot.
  • Battle Station:
    • Fail: Laptop, couch, and coffee table
    • Minimum: Desktop space, comfortable chair, professional backdrop, non-echo-y acoustics
    • Ideal: Minimum requirements, plus: quality peripherals, printer, sit/stand desk, Airpod Pros or equivalent
    • Pro: Ideal requirements, plus: multiple monitor setup, docking station, wired noise-canceling headphones with microphone, external camera, Herman Miller-type chair

So, what’s your score? If you have more green flags checked than you do yellow, and zero red flags, congrats! Remote work sounds like a great fit for you, and you might even want to check out our careers page if you’re looking for a change.

If you’re seeing a lot of yellow and red, that’s okay, too. Remote work may not match your lifestyle right now, and it’s good to know that before you dive in headfirst. If remote work still interests you, however, remember that things change, and there might be a time in the future where remote work is a better fit.

In either case, this list is good to keep handy as a guide to successfully working remotely. Feel free to bookmark it or share with a colleague.