our modern obsession with freedom

The Freedom Paradox

Freedom has become our new religion, our new status symbol. Or so it seems in my circle of Western-centric millennials who’ve tasted the bountiful options made possible by technology, mobility, and connectivity.

When we talk about freedom, we usually don’t mean freedom in the civil liberties sense (freedom of speech, freedom of press, freedom of religion etc). We’re probably a bit too privileged to know what the lack of those things look like. Instead, we mean things like: financial freedom; time freedom; even psychological freedom.

In the world of work, it’s “free yourself from wage slavery”, “escape the rat race”, choose entrepreneurship as the antidote to oppression and the path to financial and time freedom. In lifestyle design, it’s digital nomads with laptops positioned perfectly against turquoise water or cobblestone streets. In personal finance, it’s being asked: “why not move to Dubai where taxes are so much lower?” as though Dubai were a casual new restaurant to check out next Sunday. In our emotional lives, it’s freedom from frustration, freedom from failure, and freedom from feeling we’d rather not face.

All of this has left me auditing my own freedom. It’s a strange kind of social pressure I didn’t expect. Am I a sucker for staying in a 9-6, especially when I’ve seen around me make a success of the entrepreneurial path? Given that I have a remote job, am I boring for choosing to work from the same grey-wall facing desk for most days of the year? Am I financially stupid for not escaping UK tax rates, especially if this is not my country of birth?

Maybe.

But I can’t help but feel that this modern obsession with freedom has sometimes become misguided. When I consume content telling me to free myself from "wage slavery” (trust me, it’s been a trending term on YouTube for a while), I catch myself equating freedom with escape. And I wonder if in that rush to escape, we end up missing the thing that we’re actually looking for.

My hunch is that we think we want freedom. But what we actually want is meaning and purpose.

In 1941, social psychologist Erich Fromm distinguished between two kinds of freedom in “Escape from Freedom”. There’s “freedom from” (e.g. external constraints) and “freedom to” (e.g. to live authentically and aligned with your desires/values). Fromm’s core thesis was that “freedom from” by itself is not enough for a fulfilling life. If someone is free from “external” constraints but doesn't have meaningful “freedom to” to guide them, they'll end up feeling disorientated and distressed.

Fromm was writing in the shadows of WWII, the atrocities of the Third Reich, and the rise of totalitarianism. Fortunately, the world looks quite different today. But I think his theories are still very relevant in this age of maximal choices.

You can quit the 9-6, but be trapped by the hustle or paralyzed by the anxiety of unstable cash flow. You can move to Dubai for zero income tax, but be emotionally and socially stranded. You can retire early, but fall into nihilism because you’ve focused on freedom from work rather than freedom to pursue projects you care about. You can pursue freedom from anxiety/frustration/failure, but that might stop you from experiencing the hard things that make you resilient.

I think that freedom has an internal paradox, much like happiness. The happiness paradox says that chasing happiness directly can make us miserable. When you go hunting for happiness, your attention fixates on its absence. So we measure, we compare, and then we spiral down.

Assuming a baseline level of civil liberties, I’d say that “the freedom paradox” is the phenomenon that the more we chase freedom, the more we feel trapped. When we make freedom the goal, we’re constantly chasing the next escape: the job, the city, the partner, the tax rate. We become obsessed with getting away, rather than building toward.

In his poem “On Freedom” (published 1923), Kahlil Gibran writes

“...I have seen the freest among you wear their freedom as a yoke and a handcuff

... you can only be free when even the desire of seeking freedom becomes a harness to you, and when you cease to speak of freedom as a goal and a fulfilment.”

I’ve messed up his poetic spacing here, but I hope his point is clear: doing everything you can to remove interference doesn’t make you more free if that pursuit becomes all-consuming, like handcuffs. At best, we end up living a life defined by not what we're choosing, but by what we're trying to avoid.

A final thought: I value my freedom and autonomy a lot. But there are many other things I value - belonging, security, meaning, family, truth. I think part of getting older is recognizing the inevitable trade-offs between values we care about, rather than acting as though we can maximize everything at once. Philosopher and political theorist Isaiah Berlin spoke of this in his 1958 essay “Two concepts of liberty” (where he makes a similar distinction as Fromm between “negative liberty” - freedom from - and “positive liberty” - freedom to). Berlin said that freedom is only one value among others. It’s not the only value and certainly not the highest one.

And so, for now, I haven’t escaped wage slavery or ditched the structures of a 9-5. I still work from the same desk for most days of the year. I still pay undesirable UK tax rates and complain about it. I still surround myself with the same people every day. And no, I don’t feel trapped and, no, I’m not doing these things because I’m afraid to leave. It’s because I really like it.

That doesn’t mean it won’t change. But if they do, I hope it won’t be in pursuit of some abstract notion of freedom or some desire to escape, but towards something more specific. I don’t think I need more freedom. What I need is more clarity about what to do with the freedom I already have and more courage to put it to good use - for myself, for the people I love, and for the world.