Could Remote — Freelancing Mashups Become The Normative Careers Of Tomorrow?

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As a six year veteran of the rough-and-tumble world of freelancing, I’ve been part of my fair share of remote teams over the years.

Which is why I’ve been delighted to observe the remote renaissance unfolding as the pandemic continues.

I pick that word deliberately. Because as any freelancer knows, the technology to support remote working has been around for years.

It’s just that we humans have finally — in fact, rather belatedly — gotten around to exploiting its full potential. (Being based in Israel, I’m also very excited to witness it widening options for fellow English-speaking expats based in this part of the world.)

However, the internet doesn’t need another article extolling the virtues of working remotely which is why I didn’t sit down this morning to write that piece.

Employers have gotten the memo. And if statistics are to be believed, most newly minted remote workers need no convincing of its merits.

But what I do think has been underdiscussed is the possibilities that are unfolding for dual-income careers that blend some aspects of remote working with freelancing. In fact, I think that such blended approaches could even eclipse both new working worlds in their own right.

Because while many of us have been ditching the morning commute for the morning shuffle into the office in the next room, the inexorable rise of freelancing and the gig economy has been going on quietly in the background. And this trend shows no signs of abating.

As our peers in the corporate world transition towards work arrangements that come close to mimicking the ones that us freelancers are already natively accustomed do — and which work around our schedules — increasingly I predict that it’s going to become normal for workers to mix and mingle between the two.

Specifically, I’m talking about:

  • Career trajectories that shift between remote work and freelancing becoming increasingly the norm. And here’s my prediction. Fluid meandering between the two is going to become increasingly normal as employers understand that the value of one’s work isn’t determined by whether you physically showed up to an office or whether you executed your workload from besides a beach. Ultimately — ideally — this would lead to something like a skills-based meritocracy in which presenteeism and one’s ability to navigate corporate politics are no longer the chief determinants of one’s career success. In concrete, and if this unfolds, it is going to be very normal for employees to jump between worlds. Hopefully, very soon, this won’t even raise any questions. “So …. why do you want to give up on freelancing?” — a question many making such a transition are fielding today (I got asked it recently) — simply won’t get asked tomorrow. As society (collectively) figures out the best way to pair those providing labor with those who need it, we’ll all understand that we’re playing an ever-shifting game called “we’re figuring out the best way to do this working thing.” And as we do, we’ll stop subconsciously lionizing the conventional way of working — showing up to an office Monday to Friday — simply because it’s what we’re familiar with and it’s what our parents did to earn a salary.
  • More and more workers hedging their bets by dabbling in both worlds. If part time hybrid and fully-remote options become increasingly the norm — and that’s prediction two, that they will — then two options are going to increasingly present themselves. Because these aren’t currently that commonplace, neither are currently major dynamics. Firstly, the ability to serve on multiple (salaried) remote teams simultaneously. And secondly the ability to be part time remote (salaried) workers and part time freelancers. If you’re the one thinking about doing this, then to your spouse/progeny/dog the optics will look essentially the same. You’ll be working from home for an office and communicating with some other humans on the other end of your webcam or email client. But the internal divisions of your working life will be different and managing your tax affairs might require a little bit more coordination. Monday to Wednesday might be dominated by Slacks and meetings with your “salary job” team. Thursdays and Fridays by client projects. Of course, there’s nothing stopping anybody from already doing this. It’s merely that it’s a lot less commonplace than it already could be. As that fades into the background, attitudes will change and so will the way employers are forced to behave to accommodate that being the norm. Hopefully we’ll see an end to ridiculous clauses in employment contracts that preclude salaried workers from drawing down any other form of employment (I’ve been offered several such contracts!). As a society, we’ll move away from the idea that offering an income entitles an employer to monopolize that individual’s available supply of labor. Ultimately, that belief will come to seem archaic.

Two Societal Re-Architectures Needed To Make These Predictions A Reality

As I’ve written here before concerning remote work, there’s an inevitable lag period between when the possibilities of remote work can realistically be achieved — that’s here already — and when they manifest. That’s down the road a little.

Given employers’ reluctance to radically shift the face of the working world overnight, there’s typically, in fact, quite a gap.

We’ve been seeing that, for some time with remote employment.Therefore, it’s unreasonable to expect that these changes will unfold in a manner that’s any different.

While the news cycle would suggest that we’re already basking in the glorious new era of remote-first working, the hiring market which many remote jobseekers encounter— and the often skeptical attitudes of employers — lay plain that that’s not quite yet the case.

In order for the above predictions to come true we’re going to need to see two changes. I believe that these will happen, but it may not transpire overnight:

  1. A move away from presenteeism. Employers are increasingly understanding that employees don’t need to physically be sitting in the office in order to add value . Quickly, in fact, that belief is starting to seem outmoded. The next realization is going to be a move away from corporate culture’s longstanding love affair with presenteeism. Not only can remote workers be just as productive from Budapest or Dubai, they don’t even need to make a full time commitment in order to bring enough value to justify their place no the team. Once this happens, we’ll see a mushrooming of part time remote and hybrid work opportunities.
  2. Acceptance of unconventional career paths as the norm. Traditionally, careers are linear evolutions as employees shift from one employer to the next, acquiring increasing remuneration and seniority in the process, until they finally call it a day, announce retirement, and live off carefully nurtured retirement savings vehicles. The careers of tomorrow — nay, today — are going to look nothing like that. Individuals — for even calling them ‘employees’ will no longer be strictly accurate — will swim seamlessly through the shifting tides of how work is normally carried out for companies. Shifting between periods of freelancing and dedicated tenures on fully remote teams will be quite normal. Many will do both at the same time. (The pension ‘stuff’ therefore requires urgent attention and it may fall to governments to ensure that freelancers are adequately contributing to prevent later destitution. It’s not a minor detail!)

The explosion in remote and hybrid working is dovetailing with the rise of freelancing which is going to constitute a substantial part of the supply of labor in coming years.

As these trends converge, we’re going to see increasingly fluid employment options becoming the norm for individuals.

This is going to lead to a more diverse and exciting array of employment options as careers increasingly take on very different contours from anything that has been commonplace to date.




Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

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Daniel Rosehill

Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

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