How I Stopped Waiting for Permission to Enjoy My Own Thoughts

I was standing in the poetry section of a used bookstore when I realized I had been talking to myself for the better part of three minutes. Not the muttering under your breath variety of self-talk, but an actual conversation about whether poets who use lowercase letters for their names are more or less pretentious than poets who use Roman numerals in their titles, conducted at what I can only describe as a conversational volume. A college-aged employee reshelving philosophy gave me a look that suggested he was reassessing whether the store needed a panic button, and I became suddenly aware of how I must appear: a grown man, alone, delivering literary criticism to an invisible companion.¹

The embarrassing part was not the talking itself (though yes, that too) but the fact that I had been genuinely enjoying the conversation. I was making myself laugh.² For several beats I had the unhelpful double awareness of being both the person talking and the audience member thinking, this guy is kind of funny, which struck me as either a sign of developing mental illness or, more charitably, something worth paying attention to.

Most of us spend an enormous amount of mental energy arranging our lives to avoid being alone, and not just in the obvious “Friday night plans” sense. We schedule back-to-back meetings, scroll through feeds, keep the television on as background noise, maintain standing coffee dates with people we do not particularly want to see, reply “sure, happy to hop on a quick call” when we are neither happy nor free, all in service of a single goal: not having to spend time with ourselves. When forced into solitude (a delayed flight, a canceled dinner, a Sunday morning with no plans), we treat it as a problem to be solved rather than a space to be inhabited. We reach for our phones with the urgency of someone reaching for an oxygen mask.³

The question nobody seems to ask is: why?

Writing in the 1890s, William James spent considerable time thinking about what he called the “stream of consciousness,” this continuous flow of thoughts and sensations that constitutes our mental life.⁴ He was interested in the texture of consciousness itself: the way our minds move from one thought to another, the associations and digressions that characterize how we actually think (as opposed to how we think we think).

What strikes me about James’s work is not his technical precision but his baseline assumption that the contents of one’s own mind might be worth sustained attention, that there is something genuinely interesting happening in there before you add podcasts or TED talks or threads explaining why your morning routine is wrong.

We seem to have misplaced that assumption. Or rather, we have replaced it with something else: the belief that our unmediated thoughts are somehow insufficient, that left to our own devices we will inevitably slide into boredom or melancholy or some other unpleasant state that requires external intervention. We treat our own consciousness the way we treat airport layovers and waiting rooms, as something to be gotten through, not experienced.

The interesting thing about learning to enjoy your own company is that it is not, despite what the self-help industrial complex might suggest, about achieving some Zen state of inner peace where you sit cross-legged and radiate equanimity at your living room furniture. It is more mundane than that. It is about developing a relationship with your own mind that is characterized by something closer to curiosity than judgment.⁵ You are not trying to become a better person. You are just trying, initially, to become a slightly less hostile audience to your own thoughts.

Aldous Huxley, in a book about vision and perception that nobody reads anymore, wrote that “change is only possible through movement.” He was talking about physical sight (about the way our eyes need to move in order to see) but the observation applies to mental life as well. You cannot think yourself into a different relationship with yourself through pure contemplation (though God knows I have tried, usually in bed at 1:30 a.m.). You have to actually do things alone. You have to take yourself places. You have to, and I recognize how this sounds, take yourself on dates.

This is where most advice about solitude goes wrong. It presents being alone as a kind of spiritual practice, something that requires intention and discipline and probably a meditation cushion that costs more than your first car. But the people who actually enjoy their own company did not get there through rigorous self-improvement protocols. They got there through the considerably less glamorous route of spending time alone and finding, to their surprise, that it was not terrible.⁶

I started small. I went to movies by myself, which felt transgressive until I realized that nobody in a movie theater is paying attention to anyone else anyway (everyone is doing their own private negotiations about whether the amount of popcorn they have eaten qualifies as “a problem”). I took myself to lunch at places with actual tablecloths, where the implicit assumption is that you are meeting someone, and I brought a book but did not always read it.⁷ I drove to a trailhead an hour away and hiked for three hours without listening to anything through earbuds, just the sound of my boots on the trail and my own thoughts circling around whatever they felt like circling around, which turned out to be an alarming amount of time spent ranking sushi spots I've eaten at.

What I discovered was not that I had some rich inner life that had been waiting to be unlocked (I did not), but that my own thoughts were better company than I had given them credit for. They were not profound, exactly. They were not the kinds of insights that would make good Instagram captions. But they were specific, occasionally weird, and they were mine. They were sufficient.⁸

Anne Lamott, who writes about writing with more honesty than almost anyone, talks about how reading and writing decrease our sense of isolation, how they “deepen and widen and expand our sense of life.” She is describing something that happens in the presence of another mind, even if that mind exists only on the page. But I think the same principle applies, in a smaller, quieter way, to spending time with your own mind. When you stop treating your thoughts as something to be managed or optimized or transcended, when you stop waiting for them to be more interesting than they are, they become better company.

This is not an argument for complete isolation (which would be both unhealthy and boring), but for a different relationship with the prospect of being alone. The goal is not to prefer solitude to connection but to reach a place where the sentence “I have to spend the day alone” does not register as a problem requiring a solution.

The practical implications of this are larger than they might initially appear. Every decision about how to spend your time, every choice about whether to say yes or no to an invitation, every question about what you actually want (as opposed to what you think you should want) becomes easier when you are not operating from a position of low-level panic about being alone. You can say no to things that do not interest you. You can say yes to things that do, even if you have to do them alone. You can make plans based on what you actually want to do rather than what will ensure you are not by yourself.⁹

There is a philosophy I have been trying to practice recently: look for reasons to say yes, and only say no when you have to. This sounds simple, but it requires a kind of baseline comfort with yourself that most of us have not developed. If you are afraid of your own company, your default mode is to say yes to almost anything that promises distraction, which means you end up doing a lot of things you do not actually want to do. If you are comfortable alone, you can afford to be more selective. You can say yes to things because they genuinely interest you, not because they save you from yourself.¹⁰

This connects to a larger principle about how change happens, or rather how it does not happen. We tend to think of personal growth as something that occurs through insight, through having a realization about ourselves that then leads to different behavior. But this is mostly backwards. Insight usually follows behavior change, not the other way around. You do not think your way into being comfortable with yourself. You become comfortable with yourself by spending time alone and discovering it is not as bad as you thought.¹¹

I have been thinking about this in terms of dreams and attempts. Not dreams in the aspirational Instagram sense, but dreams in the sense of imagining your life being different in some specific way, and then making an attempt to see if it works. The person who is comfortable alone can make more attempts, can try more things, can fail more often, because failure does not carry the additional cost of forcing them back into isolation with their disappointment. They are already okay with their own company. They can fail, go home, sit on the couch, and not have to drown the aftertaste in twelve straight hours of streaming.

This is probably why most meaningful change (in individual lives and in the world at large, though I am in no position to opine about the latter) seems to come from people who have learned to be at ease within themselves. Not because they have achieved some enlightened state, but because they are not constantly trying to outrun their own thoughts. They can sit still. They can be alone with an idea long enough to see where it goes. They can tolerate the discomfort of not knowing what will happen next without immediately reaching for a distraction.

The counterintuitive thing about all this is that learning to enjoy solitude makes connection more possible, not less. When you are not desperate to avoid being alone, you can be more present with other people. You can have boundaries. You can choose to spend time with people because you want to, not because you need them to save you from yourself. The person who is comfortable alone brings something different to friendship, something that is harder to find: the ability to let the other person be who they are without needing them to be the solution to your own discomfort.¹²

None of this is particularly dramatic. There was no moment of transformation, no sudden realization that changed everything. What happened was more gradual: I stopped treating time alone as something to survive and started treating it as something closer to neutral, and then, eventually, something closer to enjoyable. I developed a trust in my own mind, not because my thoughts became more interesting, but because I stopped expecting them to be something other than what they were.

The test, I think, is this: if someone told you tomorrow you would spend the entire day alone: no plans, no obligations, just you and whatever you decide to do. Would your first response be dread or relief? If it is dread, the problem is not that you need better solitude practices or meditation techniques or whatever else the wellness industry is selling this week. The problem is that you have not spent enough time with yourself to know whether you are good company.

The solution is embarrassingly simple: spend more time alone. Not in any special way. Not with any particular goal or practice. Just do things by yourself and see what happens. Go to the museum alone. Take yourself to dinner. Drive somewhere you have never been. Sit in a coffee shop and do nothing. Let your mind wander wherever it wants to wander. See if you can get through an hour without reaching for your phone not because you have the discipline to avoid it but because you are genuinely occupied with your own thoughts.¹³

What you will find, probably, is that you are not as boring as you thought you were. Your thoughts are not as unbearable as you feared. The silence is not as oppressive as you imagined. You might even, if you stick with it long enough, make yourself laugh in a bookstore, and find that you do not care who sees.

¹ This happens more often than I would like to admit, though usually with slightly better volume control. The fact that I found this embarrassing probably says more about my relationship with appearing normal in public than about the inherent weirdness of talking to yourself. It is remarkable how much of adult life is just elaborate choreography to avoid looking like the sort of person who talks to themselves in bookstores. ↵

² Specifically, I was developing a theory about how the more experimental a poet's typography, the more likely they are to have an MFA from Iowa. This observation is probably unfair to both experimental poets and Iowa, but it entertained me, which at that moment was the relevant metric. ↵

³ I am as guilty of this as anyone. I have picked up my phone during a red light that lasts fifteen seconds, as if even that amount of time alone with my thoughts represents an unbearable void. The signal turns green and there I am, halfway through three notifications I will not remember having read. ↵

⁴ James's Principles of Psychology is one of those books that everyone references and almost nobody reads, which is unfortunate because it is far more readable than you would expect from a psychology text published in 1890. He writes about consciousness the way a novelist might, with attention to texture and nuance rather than just mechanism. You get the sense that he actually liked being alone with his own mind, which feels almost indecently old-fashioned. ↵

⁵ This is harder than it sounds. Most of us have been trained to approach our thoughts as problems to be solved or symptoms to be managed, not as phenomena to be observed with something resembling interest. The modern term for “spending time with your own mind and seeing what it does” is “ruminating,” which should tell you something about our baseline attitude. ↵

⁶ I realize this makes it sound easy, which it was not. The first several times I did anything alone that seemed designed for pairs or groups, I felt acutely self-conscious, as if everyone around me could tell I had been forced into isolation by some personal failing. Nobody could tell. Nobody cared. They were all busy performing normalcy for imaginary audiences of their own. ↵

⁷ The book was mostly for show, a prop to signal that I was there intentionally, not because I had been stood up. By the third or fourth time I did this, I stopped bringing the book. The staff, having now seen me multiple times, seemed to accept that I was simply the sort of person who eats food while looking at walls. ↵

⁸ This is probably the most important realization: that your thoughts do not need to be interesting by anyone else's standards. They just need to be interesting enough for you to want to keep thinking them. The bar is lower than you think. Also, the bar will move. What bores you when you are frantically distracted becomes oddly compelling when you are not. ↵

⁹ This applies to big decisions and small ones. Whether to go to a party where you do not know anyone. Whether to take a job in a new city where you have no friends. Whether to spend Saturday alone reading instead of making plans. All of these become easier when you are not operating from a place of desperation about being by yourself. “I don’t want to be alone” turns into “I could be alone and still choose this,” which is a different sentence. ↵

¹⁰ The paradox is that the more comfortable you are alone, the more genuinely social you can be. You are no longer showing up to things because you need to avoid yourself. You are showing up because you want to be there. People can tell the difference, even if they could not articulate it on a feedback form. ↵

¹¹ This is probably why therapy that focuses on insight without behavior change tends to produce people who have very sophisticated explanations for why they are stuck but remain stuck nonetheless. Understanding yourself is useful, but it is not sufficient. You have to actually do different things, ideally before you feel fully ready and self-aware and healed and optimized. ↵

¹² There is probably an essay (or a book, though I am not qualified to write it) about how most relationship problems stem from people trying to use other people to solve their discomfort with themselves. The person who cannot be alone tends to make other people responsible for their emotional well-being, which is both unfair and exhausting for everyone involved. It is hard to be a human being; it is harder when you have been unofficially hired as someone else's emotional infrastructure. ↵

¹³My phone remains an easy escape hatch from any moment that threatens to require actual presence. But I am better at it than I used to be, which feels like progress. I can now, on good days, stand in a grocery line for a full ninety seconds without checking anything. This is not heroic by any historical standard except ours. ↵