I saw the best minds of my generation become freelance strategists
15 February, 2026
It seems like I can't turn around on LinkedIn these days without seeing an announcement that someone has decided to go freelance.
Obviously there's some selection bias at play here: if I were going freelance, the first thing I would do, suddenly panicked about paying bills at the end of the month, would be to shout about it on LinkedIn and try to get some work booked in. Still, it seems like, in the last year or so, there has been a real deluge of freelance announcements, particularly from relatively senior people in my sector with great reputations.
In fact, that's what makes the lurch towards freelance feel so noteworthy to me: these are some of the most successful people in my sector, and they're choosing at the very least to add significant financial uncertainty to their lives if not take a pay cut, at a time when the cost of living crisis has been in the headlines for years. It also strikes me, big picture, as unsustainable: clearly the arts can only support so many freelance strategists while also paying for the actual digital services about which these strategists are offering their expensive opinions. There just aren't enough arts organisations with enough grants to embark on infinite "audience and content strategy explorations".
So why choose to do it? The obvious assumption to jump to — for me, anyway, largely because it was my primary concern when I considered going freelance a few years back — is that these people are seeking better work-life balance, and the freedom to do only the projects that really interest them. They want to shape a career that's professionally and intellectually rewarding, but that still leaves time for the other stuff they want to do with their time on the planet.
This might sound utopian and socialist and wonderful: work to live instead of live to work, etc., etc. We could be witnessing a transition towards a better kind of economy, one where people get paid the wages they want for doing work they love, a true embodiment of the post-COVID, Gen Z attitude towards employment, namely, that you should put your own well-being and happiness first, and have no loyalty to any employer except yourself.
But that strikes me as the most charitable and optimistic interpretation possible. Instead I rather suspect that it's a symptom of how much worse our economy is getting. These people aren't leaving because they've realised the value of work-life balance. They're leaving because middle management is getting increasingly hollowed out, removing viable long-term career options. That, at least, is another reason why I considered going freelance a few years back: at a certain point, there's just nowhere left for someone in my line of work to go — and while I certainly never had dreams of being on some endlessly upwards career trajectory, when you reach midlife the thought of doing exactly the same thing for another thirty years, on someone else's terms, isn't the most appealing thought.
There's something else I can't help noticing either, largely because, again, it was part of my own calculus: if you're willing to take a financial risk to pursue freelance work, it's because you can afford to take a financial risk to pursue freelance work. This is not to make any assumptions about how or why you can afford it; maybe it's as simple as, you lived modestly for ten years and saved a lot of money precisely so you could take the risk of going freelance. Or maybe you're just prepared to start living more modestly to pursue that dream. But you're not just going to give up a regular income without some idea of how you're going to keep a roof over your head and a few packs of instant ramen in the pantry.
In other words, we're not transitioning towards a society where everyone gets paid the wages they want for doing work they love; we're transitioning towards one (or maybe have always been in one) where a select few can afford to get paid less for doing work they love, while many more people hover around the poverty line spending all their waking hours doing work they hate. All of a sudden it sounds a lot less utopian.
But if you've read Chavs by Owen Jones, it probably sounds pretty familiar, too. It's just the latest iteration of the classic pattern in creative work, whereby the most desirable jobs are available only to those who can afford to give their time away for free. Because all those newly freelance strategists aren't just posting on LinkedIn about nothing; they're posting about the free webinars they're doing, or the conferences they're speaking at, or the white papers they're researching and publishing themselves, or the new digital tool they've built on spec. No doubt that sort of thought leadership is also part of the appeal of the job in the first place, but it's also the clearest and most effective way to establish yourself as a Professional Haver Of Informed Opinions — which is, of course, what you want people to eventually start paying you for.
(As a side note, I realise that giving away my time for free is exactly what I'm doing right now, and so even though I never actually went freelance and am doing this on a Sunday morning so as not to eat into my salaried hours, I'm very much part of the same problem.)
I'm not even making the argument, though, that it's bad to have creative work dominated by a homogenous bunch of mostly wealthy, mostly white independent consultants — because other people, of whom Owen Jones is only one of many, have already made that argument much more convincingly. Rather, I'm asking a question, about whether freelance content strategy is the best place for all these people to channel all that economic and intellectual power. Like, you can afford to give away months of your time and energy each year, and you spend it musing about the biggest stumbling blocks in arts website procurement?
To be clear, I'm also not asking that question as a means to shame the people who choose to do these things. (After all, I do them myself.) I'm not trying to imply any kind of moral hierarchy about how people should spend their lives, as in, how can you build a theatre website when there's a war in Ukraine or nascent fascism in America or whatever. I mean, yeesh, if I could choose to do anything with my time it would be writing quiet literary novels, and the tangled ethical debate about the role or value of art in society is another one to which other people have contributed more convincingly elsewhere.
I guess the reason I'm asking the question is... well, to be honest, I'm not sure. Just because it's one I keep coming back to month after month, mostly. Because I considered going freelance, and didn't — because I wasn't comfortable with that financial risk — and that strikes me as its own societal problem, when Elon Musk could pay all our basic living expenses each year without even noticing. Because I'm watching the best minds of my generation become freelance content strategists, because I'm sitting here describing that as socialist and utopian, because I'm parroting the same old capitalist logic that got us here in the first place: that you need to "shape a career that's professionally and intellectually rewarding, but still leaves time for the other stuff you want to do with your time on the planet" — as if a career must be a part of what you do with your time on the planet.
Because, to paraphrase Marx: the content strategists have only interpreted the world; the point is to change it. And, to carry on quoting Ginsberg: if we're all sitting around content strategising on a freelance contract, then who is changing the world?
Who reappeared on the West Coast investigating the FBI in beards and shorts with big pacifist eyes sexy in their dark skin passing out incomprehensible leaflets,
who burned cigarette holes in their arms protesting the narcotic tobacco haze of Capitalism,
who distributed Supercommunist pamphlets in Union Square weeping and undressing while the sirens of Los Alamos wailed them down, and wailed down Wall, and the Staten Island ferry also wailed,
[...] and rose reincarnate in the ghostly clothes of jazz in the goldhorn shadow of the band and blew the suffering of America’s naked mind for love into an eli eli lamma lamma sabacthani saxophone cry that shivered the cities down to the last radio
with the absolute heart of the poem of life butchered out of their own bodies good to eat a thousand years.
What sphinx of cement and aluminum bashed open their skulls and ate up their brains and imagination?
In short, I suppose the reason I'm asking the question is because other people, much smarter ones, have already been asking it for a long, long time.
Previously
You might also be interested in...
The real problem with LinkedIn, according to Marxists
I recently bought a copy of *The Influencer Factory: A Marxist Theory of Corporate Personhood on YouTube*, and I can’t remember the last time a book blew my mind quite so completely.
Read "The real problem with LinkedIn, according to Marxists"