or… Why convincing your boss to let you go remote is probably a terrible idea.

Recently I wrote a post called Going remote: the freelance option, so today I thought I’d follow up with some thoughts on one of the many other ways people suggest for making the transition to working remotely: going remote at your current job. Why go through all the hassle of searching for a new job, rejigging your resume, running the interview gauntlet, and so forth if you can just… stay where you are?

I understand why this is a tempting idea for many people, however there’s a few things you may not have considered. I’ve never been in a position where I’ve had to try and convince my boss to let me go remote, so take this all with a grain of salt, but having worked remotely in a number of different scenarios I’d like to share a few reasons why I think you should be wary of taking the “convince your boss” route.

It’s in the water, baby

This whole issue completely depends on the company you work for. If you work for a company that’s at all forward-thinking, there’s a chance you may be able to transition your current gig to be remote without running into any serious problems. For companies that already have other people who work remotely, this could be a fairly easy thing to negotiate, especially if there’s others on your team who work remotely. Having a precedent (and colleagues who can offer you empathy and support) helps. Big time.

In places where there’s less of a precedent for remote work though, I’m sceptical of how viable it is to try and transition your role to be remote. The problem is that if the whole company isn’t committed to making remote working work (and I mean really working well not just limping along), there’s a high chance that being remote will feel like a second-class experience. For an insight into how that can make you feel, check out this post by Scott Hanselman. I’ve felt the “Looks like you’re the only one on the call” rage before, and I can tell you it is Not Fun™.

It’s almost impossible to retrofit the idea of embracing remote work onto a company’s existing culture if it wasn’t something that was there (and valued) from the outset, and this is why so many companies struggle to make being remote a good experience. In the case of GitHub, people were distributed essentially since day one, so remote is pretty firmly baked into our company’s values and habits. For companies that didn’t start off that way though, or maybe were founded before the technology existed to make distributed communication possible (let alone effective), there’s a much bigger hill to climb.

Testing the (remote) water

Often what happens is that when a company that hasn’t traditionally been distributed wants to test the water, they volunteer one person or one team to “try out this remote thing”. This person is who I call the “remote guinea pig”, and it’s important to understand that this is a natural reaction for most companies. Whenever you’re unsure how something will work, the last thing you want to do is commit everything you have, right?

You absolutely don’t want to be the “remote guinea pig” though, and here’s why. The tricky thing is that in order for remote to be successful, it’s not just the people that are going remote that have to change. Every single relationship and communication those people have with other parts of the company must accommodate this new dynamic too.

Guinea pigs are cute, but you don’t want to be one

If one person in a team goes remote, but the rest of the team that person must interact with don’t change their habits, the remote person will quickly become disconnected, feel out of the loop, and generally end up “out of sight, out of mind” no matter how productive they are, how well they communicate, or how effective they are at their work. The remote experiment breaks down through no fault of their own.

When this happens, there’s a real risk that the decision makers (likely still back at the office) take a look at how the experiment went and conclude that it was a failure. Their assessment is correct—it definitely failed—but what they probably don’t realise is that experimenting with remote work this way is doomed from the start, and it’s not the remote guinea pig’s fault.

In order for a company to make remote working work, it’s not the people going remote who have to change their habits (although that’s definitely part of it), it’s the people who are still in the office that will make or break whether remote working is successful in your company.

Of course it all depends on the company and your situation. Transitioning your role to be remote absolutely can work, but if it looks like you’re going to be a “remote guinea pig” for your company, proceed at your own peril.

The alternatives

So what should you do if you’re seeking the freedom and flexibility that working remotely brings? Well there’s a couple of options. One option that I can personally recommend is to consider going freelance. The other is to take the plunge and look for a position at a new company that perhaps has more firmly embraced remote working as the status quo.

Don’t touch that dial

I’ll be writing more on how you can make the switch to working remote soon, so if it’s a remote job at a new company you’re after, make sure you subscribe to my newsletter to get future posts in your inbox. Stay tuned!