A Remote Work Future May Make Freelancers of Us All

Last night I had a conversation with journalist Cam Wilson, who brought up something I hadn’t thought about - that the nature of remote work removes the specific geographic friction of changing one’s job. To paraphrase Wilson, when changing job is basically the same as logging into a new Slack, the shift when you start a new position isn’t as significant and, by that same logic, leaving a job is no longer a situation that involves uprooting your life and changing your routines to start anew.

This is a subtle yet meaningful shift in how we consider how and where we work. I’ve made the argument previously that offices exist to trap people, and I think that Cam’s point adds layers to what that entrapment actually means. When we work in an office, we change our lives to make sure that our commute is easier - renting an apartment to be closer, or getting a nicer car so that the drive isn’t as bad, becoming regulars at local bars where we go to drink with coworkers - and plan our existences around where our employers want us to be and when. We also naturally build our families around where we work - the schools our kids go to, our partners’ friends and jobs, and so on - meaning that when we change jobs, even for a better situation and pay, we also have to factor in the difficulty of uprooting our lives.

Working in an office means that your life’s center of gravity is work. Remote work adjusts that center of gravity to whatever benefits your life as a whole. While you may choose to live with access to similar metropolitan areas, that access is on your terms, and mostly has to be justified. Hell, I did the same thing for years, living in Danville, California while working remote, but traveling into the city for meetings before people realized we could do literally the same thing but on Zoom. At the time, I also know that client retention was slightly based on having a California presence, and even then I was confident it didn’t matter. It was a group exercise in unconscious denial - that having someone in California was “better,” despite the fact that the reporters you wanted were spread across the country and, well, even the California ones didn’t necessarily want (nor need!) to meet. The security blanket of geography mattered a lot, until it didn’t.

The fight against remote work by large organizations is all about control, as I’ve said a billion times, but I’d never really considered how specifically our lives are built around work, and how changing how and where we choose to live our lives changes that power dynamic. If choosing to quit your job and start another is basically changing email and Slack logins, it becomes a lot harder for companies to retain people based on anything other than compensation and workplace conditions. While there are fewer soft abuses (micromanagement, distractions, etc.) from office culture, there are fewer of the minor positives and weights that the office generates to keep us from quitting. We may genuinely enjoy parts of our commute, or the luxury of a particular office, or people we work with, or office happy hours - all things that are nice and will make us stay at a job, but aren’t actually worth staying at a job for once you consider the alternative.

Companies have put a great deal of money into having a nice office, but also into having one in a cool area with good restaurants and bars so that you build your life around where you work. While I’m sure that there’s a nice reason too - companies want to attract people and giving them a nice environment in and around work - I also believe that part of this is to intentionally anchor a person to a particular place. If you leave your job, you’re leaving behind a chunk of your life…which becomes an unconscious part of how you’re compensated for your work. Remote work removes these subtle incentives, making the company have to find ways to make you stay like “treating you well” and “paying you well.”

The Mercenary Executive

Cam’s comment around remote work basically being a change in logins is salient, but in my mind goes beyond the friction of changing jobs and into the realm of what a job is and what one’s expected hours are. While running my PR agency, I’ve often had the thought that I basically have seven or eight jobs at any given time, but I call them “clients” - while I now have staff that can help with the work, there were many years where I didn’t, and the work was still done, and the clients still paid.

This makes me consider whether the very nature of full-time and part-time work is going to be rendered somewhat moot by the move to remote. A famous (and likely fake) Hackernews thread from a few months ago was posted by a person claiming they were working 10 fully remote engineering jobs where “oversight is non-existent,” saying that they could “coast for 4-8 weeks before a given job fires [them].” While this is an extreme example, one has to wonder how many actual hours a company requires of your work a day for your work to be considered complete without an office to show that you’re “present.” While the office could show on some level whether someone was “working” due to their physical presence, remote work doesn’t really have any metric of presence beyond being on Slack, and most of the time that’s merely a sign that someone has a window open.

Not to go fully galaxy brain, but remote work on some level throws out the classical structure of working hours as a whole. While yes, you probably want to be available 9 through 5 (and companies regularly ask for more!), one has to wonder if there won’t be an evaluation of how many human beings actually work all of those hours, and, indeed, consider whether that person could have another job on top of it from another company. This could mean that people basically become full-time freelancers, taking on jobs from multiple companies at full compensation (if said companies are cool with it), assuming that the work is done and their availability is balanced.

This, naturally, leads to a few forms of abuse. There are companies that will be so terrified of this possibility that they begin using draconian software to monitor your exact output and “make sure you’re working.” There are companies that will use this as an opportunity to lean harder on contract labor, avoiding having to pay benefits to people based on whatever spurious definition of “staff” they have. Companies that are already freaking out about the prospect of people not being in the office all the time are likely terrified that they’ll be paying someone “full time” for “part-time" work, despite the fact that people are fully capable of dicking around and doing nothing on full-time hours.

This particular idea is one that is not going to catch on quickly, because it so fundamentally reconsiders what work is and when work happens. The office naturally lends itself to the “if you can lean, you can clean” mindset, but without it you’re mostly diluted to whether your work is done in the way it’s meant to. This doesn’t mean you’re expected to be in a place, nor how long you’re expected to be in said place, nor anything else other than your tasks…which is effectively a freelance career.

A sidenote: one of the biggest limiters of this movement in America is the broken, avaricious healthcare system that has tied work to healthcare. The best plans are offered through companies’ benefit programs, and without at least a public option (but realistically we need Medicare-for-all), corporations are still going to have an oversized amount of power over people’s workplace portability. And no, the Affordable Care Act plans are not sufficient.

This may all be a pipedream, and definitely isn’t something that someone new to their career could (or even should?) do. But it’s a way in which I see the substrate of work changing based on remote work - a disconnection from the classical eight-hour work day, and a move toward a valuation of a worker based on their output rather than their ability to be somewhere. A remote future is one that could create a massive debate around what exactly we pay people for - is it their time? Is it their output? While we definitely want people to be available when we need them, do we really care what they do when we don’t?

The inverse of this conversation is, of course toward how remote work creates more ability for us to spend more of our time not working. If we’re not expected to work 8 hours a day, perhaps we will simply choose to work less and do something else?