The Problem With Side Hustle Culture And Its Champions

Celebrating callous survival mechanisms indirectly supports exploitation and perpetuates impossible financial conditions for millennials

Daniel Rosehill
6 min readMar 15, 2022


Opinion: the ubiquity of remote working has made side hustling commonplace and spawned a legion of those eager to champion it as a hallmark of industriousness. But is it really so? Photo: Pexels

Every time I see a person on the internet championing the side hustle — as if having one were something great, glorious, and the marker of rugged industriousness — I do a double take.

And they’re not exactly hard to find.

The supporters of side hustlers — as always on the internet, extremely dogmatic, highly virulent in tone— are simply everywhere.

Their preponderance doesn’t appear tied to any fluctuation in global financial conditions. Even during the present pandemic-led downturn, for instance, they’re out in force — telling us that if we’re not actively side-hustling, we’re doing it all wrong.

They host podcasts. They can be found penning inspiring-sounding posts on LinkedIn that equate holding side hustles to living the modern, millenialized version of Living The American Dream (TM). This platform — for whatever reason — attracts them like moths to a flame. You’ve probably heard it many times already. You should have a side hustle. You must have one, no less.

And the problem — I would argue — is that they’re all badly wrong.

The Problem With Side Hustles

So make it clear why I have a bone in this flight, let me take you through my own interesting employment history — unexpectedly full of pivots and shimmies.

I arrived to Israel — as a Jewish immigrant from Ireland — 6 years ago (it was actually seven, but I’ve become accustomed to calling it six because it makes me feel less bad about my progress in learning Hebrew, or lack thereof — I’m still not what I would consider adequately fluent).

There are two myths here that I’d like to play a small part in debunking. The first is that all Jews are rich and excellent at managing their financial affairs (and those of others).

While I come from a middle class background and wish to do nothing to underestimate that position of relative privilege, equally I arrived to Israel with a starting float of about €500 and my financial strategy in life has hitherto consisted primarily of placing an ATM card into a digital slot and hoping something comes out the other side. I’m pretty sure I’m behind on my pension contributions.

The second is that Israel is a war-torn land that’s highly geopolitically contentious but also (one assumes) cheap. It’s not. A pint of larger, here, costs an eye-watering sum that, in expensive parts, is now close to $10 (that’s before service, by the way).

In fact, Tel Aviv was recently named the world’s most expensive city on the planet. So let me correct that. It’s horrendously expensive here and survival — for those of us not working at the pinnacle of high-tech or the heirs to large family fortunes — is something of a gritty struggle with strong flavors of scrimping, saving, and trying to find imaginative ways to top up our incomes. If you’re reading this from a major metropolitan area in the US, our lives may have more in common than you thought.

So as an immigrant arriving to one of the most expensive places on the planet with a modest starting float, I did what any immigrant in my position would, I’d like to think, have done: I started hustling.

Hustle one — it has continued virtually to the present — was freelancing. I hold a journalism degree. I love writing. And I love technology. Fortunately, there appears to be a robust and continuing demand among tech companies, especially startups, for people who can write about their products in order to help them sell them. In other words: if you want to take it, there’s work available.

I fairly quickly found stable employment at one of these technology companies. But — albeit with less fervor — I continued my side-hustling.

Why you might ask? I hate to break it to future writers or marketing communications professionals, but this field, as much as I love it, doesn’t command the top paychecks (that’s not to say, I emphasize, that it can’t provide a middle class income).

Thus, over the course of the past few years, I’ve written probably hundreds of blogs, case studies, speeches, and even books on behalf of a miscellany of technology companies, agencies, and entrepreneurs ranging in location from Singapore to Israel to Ireland and countless places in between. Some of those authored from hotels. Many while formerly on vacation while a futile “out of office” autoresponder tried to restore some kind of calm.

Secondly .. I come back to the cost of living thing.

To give myself a realistic chance of being able to afford an occasional staycation in one of the many grossly-overpriced hotels in this part of the world — or perhaps even to leave these climes altogether for a bit — I had to earn more money. If I wanted to not have to choose between indulging in my newfound favorite hobby — videography — and buying new clothes … I needed more income. Etc, etc.

If Side Hustling Is Anything, It Ain’t Pretty. Or Glorious.

As I’ve tried to make clear, I didn’t see side-hustling as something I got into because I was an ambitious Yuppie trying to make as much dough as possible while I still could.

There are those who fit that mold, I’m sure. But I reckon that for many more enduring the side hustle isn’t a hallmark of outsized industriousness or ambition.

Rather, it’s much better described as a compensatory mechanism that’s intended to rectify, sometimes only partially, full-time incomes that just don’t stretch far enough in helping to meet financial goals, or even achieve a good quality of life.

Which is not to say that there aren’t benefits to side-hustling beyond the money generated. There are.

My years’ freelancing have probably made me better at managing my own business, developed me into a more well-rounded professional with more accrued experience than I would have got from just doing one job. It’s also boosted my professional network through doing work for companies other than my employers who have referred me in turn to more contacts (etc).

But equally, I would rather have been spending time working on boosting my network of personal contacts. Ie, hanging out on my weekends with friends. In large part, I can’t help but feel that that time was, if not squandered, spent on activities that I would rather have skipped out on.

And that’s what side-hustling unfortunately entails.

Spending your weekend mornings turning in projects for clients that you couldn’t get to during the week because you were too busy and then exhausted from your main job.

Having your weekends reduced to effectively one day rest periods because one of them has to go towards taking on extra work.

And trust me, it’s as ugly as it sounds.

It leads to burn-out. Stress. A nagging feeling that you’re never truly off the clock because if you’re not working your day job you should be either working on your side hustle or (the much harder part) doing all the stuff needed to land projects for that (marketing, holding introductory meetings, making sure the accounting is in order, etc).

So to my mind (which, admittedly, tends to be a highly opinionated one), those championing the cause of the side hustle are endorsing, effectively, a perverted version of The American Dream.

They’re probably doing so unwittingly. But I believe that that’s equally the side, or the cause, that they’re out batting for.

One rife with exploitation, suffering, and inhumane working conditions (that bypass conventional legislation aimed to stymie this because they are spread between employers and other parties).

Legislators may enforce laws designed to protect employees from submitting themselves voluntarily to inhumane working conditions that deprive them, practically, of the very opportunity to sleep.

But no legislator , government, or country — at least to the best of my knowledge — has instituted mechanisms designed to prevent those working conventional 40 hour workweeks from then spending their evenings freelancing on Fiverr, Upwork, or anywhere else. Cumulatively, those workweeks may well surpass safe and fair working limits. But it’s a form of exploitation that’s almost impossible to prevent.

The market for purveyors of freelance services may be vibrant — such that it resembles the same kind of sea of opportunity that those arriving in Ellis Island years ago encountered — but that’s about where the similarities between the two end. One many provide the starting point for a life that is indeed filled with better opportunity. The other is just a crude and desperate way of trying to get by.

I’ve spent my fair share of time immersed in the side hustle.

Rather than championing this crude compensatory mechanism designed to ameliorate underpay and impossible financial conditions for millenials and those working these jobs, let’s invest our time, instead, in working to fix the root causes of this society dysfunction: income inequality, underpay, and unequal opportunity.



Daniel Rosehill

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