I am an overthinker. That shouldn't come as a surprise to anyone who knows me reasonably well. These days that counts as a problem. Overthinking is something to overcome, the thing standing between you and a freer, easier life. So let me come to the defence of my fellow overthinkers.
When you think about freedom, you'll often come to some version of having options, and nobody stopping you from picking one. Political philosophers call something close to it negative liberty, see also Positive and Negative Liberty.
Yet I often feel overwhelmed by the sheer breadth of possibilities, and who doesn't? In the moments when I had full freedom (setting aside debates about free will), with no one stopping me, and x as available as y as available as z, I didn't feel relief or joy. Mostly I felt anxiety. It's a phenomenon sometimes labelled in psychology and marketing as choice overload. "Stop overthinking. Get out of your head", as they say.
Now I can't be a wannabe philosopher without mentioning Descartes. And while most know him for his cogito argument, he also has an interesting conception of freedom. He would have found that advice against overthinking half right. What he finds wrong is where things get interesting.
In his fourth Meditation, Descartes calls indifference, the state in which nothing pulls you one way or the other, the lowest grade of freedom. Not because choosing is bad, but because hesitation is a symptom that you don't yet understand enough to see what to do. The highest freedom he calls spontaneity.
For in order to be free, there is no need for me to be inclined both ways; on the contrary, the more I incline in one direction... the freer is my choice.
True knowledge can make a choice so clear and distinct, like a mathematical truth, that you feel irresistibly drawn to it. As irresistibly as the urge to fill in the dots of 2 + 3 = … Nobody experiences that urge as a limit on their freedom. And refusing to assent that 2 + 3 = 5 is hardly an act of freedom; it's closer to an act of stupidity.
On this view, the anxiety of open choice isn't the price of freedom but a sign that it is incomplete.
The usual advice is to turn off the mind. But thinking isn't the problem; a particular kind of thinking is: weighing the same options again and again without learning anything new. Thinking that actually gets to the bottom of a problem reduces options instead of looping over the same set, until you understand the situation well enough that most alternatives stop being options at all. It then becomes not a matter of having more doors to choose from, but seeing which one to open.
The paradox is that Descartes' highest freedom involves no deliberation at all. But you only get there by thinking first. A mathematician doesn't hesitate over 2 + 3, yet she didn't reason her way there as a pre-schooler. She took it on authority and drilled it into memory. We all start on authority. Often it's only in a foundations course, years later at university, that we go back to the basics and understand why. From then on, her answer rests not just on memory but on insight. And this is the core idea, that with enough clarity, you make the right choice not out of reflex or habit, but because you feel its pull.
Descartes knew we rarely reach that clarity in everyday life. Like lacking clarity when choosing between two jobs, or taking a shortcut to your destination. For those cases his advice was different: once you've decided, be firm. Travellers genuinely lost in a forest shouldn't wander in circles but walk straight in one direction.
Earlier this month OpenAI released GPT-6 Astra, which it bills as state of the art at computer use: operating software, browsing and completing multi-step workflows on your behalf, down to filling out your tax returns and making 3D models in Blender. In one of the launch demos, it simply books a tennis court. If the standard cure for overthinking is to get out of your head, the ultimate cure is to let something else be in it for you. Hook up Astra to a pair of smart glasses, and highly capable models take the front seat of daily life: seeing what we see and acting on our behalf. I won't just ask whether there's a tennis court free this afternoon, or whether to order Greek or Italian. I'll ask it to book the court. And eventually, to decide when I should play, and against whom, given the week I'm having. The answer will already be there, in my field of view.
Will we feel freer, piggybacking off frontier models? The short-term anxiety would certainly fade. But for Descartes, spontaneity is also personal: a great light in my intellect followed by a great inclination in my will. Someone else's insight can't do that for me. He also warned about sensory impressions that come with a judgment already built in, judgments we never actually made. Advice that arrives through your glasses with the immediacy of seeing looks a lot like that.
Checking whether a tennis (or padel) court is free is harmless though; that's just trivial information. And where clarity is genuinely out of reach, letting the glasses pick a direction is arguably just the forest maxim, outsourced. The harder case is where insight was possible but we outsourced it. There the agent removes the hesitation without giving the clarity. Will it feel like spontaneity? Maybe it's the relief of walking out of the dense forest. But we were never truly lost, and relief isn't the freedom of seeing the right path.
For Descartes, error arises when an infinite will reaches beyond a finite understanding. Where we affirm what we don't actually grasp. An agent that always has the answer makes that reach easy. Will a Claude Max subscription make that will more brazen still? Mine probably has.
We can't be blamed for our ignorance, but we are responsible for what we assent to. Mistakes happen, as my lecturer once elegantly put it, when we don't control our will sufficiently to keep our mouths shut. Letting the glasses decide is still an act of assent. As far as negative liberty goes, nothing is lost: every door stays open. We just stop looking at them.
So the lesson isn't to think more about everything, or to stop being so dependent on language models. Prompt in a way that draws out insight rather than answers. Where understanding is possible, think it through until the options fall away on their own. Where it isn't, choose and commit.
Don't stop overthinking. Just make sure you are in fact… thinking.