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How long can you resist the voice of the midnight hour?

Kierkegaard, Jung, and talking with yourself.

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Jonny Thomson and Big Think
Feb 20, 2026
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Hello everybody,

This week we’re looking at difficult conversations with ourselves.

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Paid members can hear my audio narration at the end of the newsletter.


There are many kinds of difficult conversations

Ben has been in a relationship for three years. His girlfriend keeps making comments about rings, weddings, and children. He keeps pretending he can’t hear them. He scrolls his phone every night, gets drunk every weekend, and laughs a touch too hard at his best friend’s weddings. It’s amazing how easily the world distracts from the conversations we need to have.

Yvette has been on the “How to have hard conversations” course. She’s even got a certificate somewhere. She has read HR’s policy on dismissals ten times in the last 24 hours. But she wasn’t ready. The second she delivered the news, Clive’s face crumpled. Banterous, bragging Clive: father of three, weekend golfer, just booked a holiday, and now crying. Not the Hollywood sob of the broken, but something subtler and somehow worse.

Lucy opens the email from the radiographers. Yan is waiting just outside her office to hear what she has to say. It’s spread. She’s always liked Yan — she likes all her patients — but she really tried this time to not get too invested. It never works. “Sam, can you tell Yan to come in?”

Conversations like this are difficult because of the emotions involved. They hurt people. And while they are difficult, they are also an unavoidable part of a life lived alongside other humans, braided in relationships.

There are all sorts of philosophical issues lurking behind these conversations, like the ethics of how, when, and why to have them. But I would argue that there is a deeper and trickier conversation we don’t often consider enough: the difficult conversation with yourself.

So, this week, we look at just that. I think it’s time that me and I had a chat.

Go well,
Jonny

Jonny (L) having a difficult conversation; Skull (R) thought death would be the end of this.

The whispering voice of the midnight hour

A conversation is between two or more people. So, you’d be forgiven for telling me that “a conversation with yourself” is a nonsense expression. You can’t play tennis with yourself, seesaw with yourself, or have sex with yourself*. You can’t have a conversation with yourself.

Fair point, fair point. If we are to go any further with this nonsense talk, I will have to make the case that we are each made up of at least two parts. We have “personas.” And, lucky for me, I think this is a fairly defensible position.

On the most psychoanalytic level, many people like the Jungian idea of a “shadow self” — or some darker, repressed aspect of ourselves that needs attention and light. Yes, all of our taboos, fetishes, and intrusive thoughts live in the shadow self, but so too do the things we say about people after they leave the room or the love we never believe we deserve. In this view, a difficult conversation with yourself means psychotherapy. It means taking a Lacanian knife to your psyche, carving away all those protective facades, and finding that buried, malnourished inner shadow or child or whatever that needs attention.

But I’d argue that an even better vision of all this comes from Søren Kierkegaard when he talks about “the midnight hour.” In his work Either/Or, Kierkegaard writes, “Do you not know that there comes a midnight hour when everyone has to throw off his mask? Do you think life always lets itself be trifled with? Do you think you can sneak off a little before midnight to escape this?”

Half a century before Freud, Kierkegaard was making the point that inside each of us there is a voice. You might call it a gut feeling, intuition, conscience, or “the midnight hour.” The existentialists might call it your “authentic self,” and the religious might call it your “soul.” Whatever name you use, the point is that this voice is always there, always whispering, always begging. It knows. It knows that you lied when you said, “I tried my hardest.” It knows that it’s not true that you had no choice. This voice tells you that you’re addicted to your phone, sugar, or the gym. It tells you that you’re unhappy in this relationship, at this job, and with this life.

There are some kinds of pain that will never go away. You ignore the slight, occasional aches, but they become less slight and less occasional every day. Over time, the pain becomes so crushingly present that you have to deal with it. Likewise, the voice will not go away. Kierkegaard argues that if you ignore the midnight hour for too long, there is at first a kind of lashing, projecting “madness” that treats the world poorly. Then, there is an utter annihilation of yourself. It “ends with your nature dissolving into a multitude.” For some, this is a kind of death. Who you are dies, and your body is shuffled onwards by the “unhappy demoniac” of society, expectations, and not upsetting anyone else. For others, this madness erupts into a crisis, breakdown, and dangerous downward spiral.

This all makes sense. It’s all very poetic. But what does any of this mean?

It means you need to take that voice seriously. See the midnight hour as a kind of pain of the soul, and as with all pain, it’s trying to tell you something important. As Kierkegaard put it, “Truly, you should not trifle with what is not only serious but terrifying.”

Sit down and have a conversation with yourself. Mute all the modern world’s clamour – no phone, no company, no distraction – and listen to your voice. This doesn’t have to be a pretentious picture of meditation. You don’t have to pull up a seat next to a fire in an ancient house. This could be in the shower, in bed, late at night, or at the bus stop as you wait drunkenly for the last ride home. Because that voice can pop up at any time, and we can either choose to listen or choose to hide it away. The advice of philosophy is to walk towards the difficult conversation with yourself.

*Counter arguments welcomed in the comments.

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Next week, we’re exploring old age and increasing your “joyspan” with Dr. Kerry Burnight. And so I’m asking:

What do you intend to do when you’re retired?

Send me your thoughts via email or comment below.

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