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Breakthrough! in the DMs
or: how I help people by actually listening to them
“Good conversation can leave you more exhilarated than alcohol; more refreshed than the theater or a concert. It can bring you entertainment and pleasure; it can help you get ahead, solve problems, spark the imagination of others. It can increase your knowledge and education. It can erase misunderstandings, and bring you closer to those you love.” — Dorothy Sarnoff
By now I’ve had over a hundred conversations with people who have asked me some form of the question “how do I figure out what I want?”
I’m usually able to be helpful to people, so much so that sometimes they gush to me me afterwards about the personal breakthroughs they’ve had in their lives downstream of our conversation– breakthroughs at work, in their relationships, with their families, their finances, creative output, all sorts of things. Just from receiving a little additional clarity in their thinking, feeling, sense-making! After I received several DMs like that, I started thinking, this is crazy. I have to do something with this. This magic shouldn’t be contained in my DMs. It should be shared with the wider world. Even if it means being mocked or misunderstood by a subset of people, it would be worth it to help other people who struggled like I used to.
Those conversations were part of what inspired me to write my 2nd book Introspect – I wanted to extrapolate from those conversations to a general framework that might be useful to more people. So far, the book has resonated with hundreds of people. It was very difficult to write, for a multitude of reasons. Writing a book is a very different task than having a conversation. Conversations are dynamic. You can respond to what the other person is saying, and if something is not working you can switch things up, try something different, “rewind”, and so on. I think the odds of someone having breakthroughs from reading Introspect are still somewhat lower than their odds of having breakthroughs from having an extended conversation with me. But the great thing about a book is that once it’s written, it can be read by loads of people, and it isn’t bottlenecked by my personal time and attention. When I struggled with the process and the architecture of the book, what kept me going were those numerous anecdotes of people’s breakthroughs. I think I would likely have given up (or procrastinated indefinitely) if I wasn’t continually driven by this sense of, “think of all the breakthroughs you could help other people have.”
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So anyway let me tell you a bit about the latest conversation I had with someone about this, which was fairly typical. They start by saying that they feel like they’ve always been thinking about the image or performance of what they’re doing – how do they know what they really like, when they so often default to acting like how they think others would like? I launch into some of my usual questions: What do you do when nobody’s watching? What do you do when you have an unexpectedly free day? They say they don’t really know… reading books, maybe. Here there are several branching paths I could take. I could ask, what books? If I went down that path, I don’t necessarily know exactly what I’m looking to hear. It’s less about what they say, and more about how they say it. It’s the meta-data.
Part of how this works is I’m genuinely always curious to know about people’s desires and interests. What sort of books do you like? What do you like about them? Which have been your favorite? Do you feel like that tells you anything about yourself? Etc. The point is to get them going, and get them talking as much as possible, and there will be clues in there to something bigger. But I won’t know in advance what those clues are. “I know it when I see it.” Sometimes this alone is intensely valuable for people – it might have been a long time since they said much out loud about what they liked, and that act might reveal or clarify things to them that were not obvious when unsaid. But there’s also often something instrumentally valuable that surfaces about it, which is why I often ask this of my marketing consult clients.
An interesting thing that came up here was, they said, “ok I know I like reading, but I don’t know how to make that my ‘main’ thing”. There are more branching paths here. If someone wanted to make reading their main thing, I could ideate with them about how to do that. Sometimes it’s super-obvious that someone should make something their ‘main’ thing, because it pretty much is already running their life in some respects, and a few tweaks would make it much more potent. But I question the premise. Why does that need to be your ‘main thing’? I would hesitate to nudge anybody towards making anything their ‘main thing’ too soon. What does ‘main thing’ even mean, actually?
And here I suspect that a lot of people have been recklessly “Ikigai-pilled”. If you’re unfamiliar with Ikigai, it’s a Japanese word that technically means “reason for being”, but if you Google it you’ll find that it’s popularly depicted as part of this 4-circle venn diagram of “what you're good at, what you love, what the world needs, what you can be paid for". And the implication is that there’s something at the heart of that diagram, where all 4 of those things overlap, and that that should be your ‘main thing’. I’ve always found this to be suspicious.
Reality is rarely so tidy, with preexisting you-shaped roles for you to slot perfectly into. I’ve personally found it easier to have a good life by scratching each of those itches separately, than by forcefully trying to centralize all of them in one ‘main thing’. I believe that the centralization is something that can happen, but it needs to happen semi-organically over a long period of time, as you pave the desire paths. But until you accumulate the requisite reputation, skills, capital, savvy and so on, you’re likely going to have to compromise on several fronts.
And that’s fine! It’s so important for people to know how scrappy everything starts out, from Beyoncé to Apple. So if you’re judging yourself for not doing your equivalent of Super Bowl performances or iPhone keynotes, you’re self-flagellating unproductively in a way that doesn’t even correspond with how reality works. It’s so bananas to me. Simply pointing this out to people often brings them so much relief, when they realize they’ve been twisting and contorting themselves to fit into a hallucination of a cartoon model of reality.
Alright, there are a few things I want to say from here.
How do I help facilitate breakthroughs?
I feel like one of the questions someone would have reading this essay would be, “But so how do you do it? How do you have these breakthrough conversations with people?” And there’s two parts to this question, right, one part is “how did you get good at this thing,” and the other part is “what is the actual process of doing the thing?” The first part is easier to answer. The second part, honestly I’m still trying to articulate. I’m not confident in my own explanation of my process. (Meryl Streep once said in an interview that she’s inscrutable to herself, which I find quite a relief, because I feel like it gives me permission to say the same about my own process. I like to try to explain myself, and it can be interesting to theorize, but the actual practice is always something slightly more mysterious and dynamic than my description of it.)
(1) The short answer to the first question is a mix of several things, something like– first of all, I’ve always wanted to be wise. This might maybe seem somewhat tacky to admit, but it’s the truth. From a very young age, I wanted to be worldly and wise. If you ask my mum she’ll tell you this story of how I begged her to buy me a copy of the Mahabharata at a temple fair one day, and how I sat down and read half of it in a single sitting. When I was a teenager I read tonnes of advice columns and self-help books, quite possibly over a million words worth. I spent hours reading on the internet every day. I would cut my teeth arguing with people on multiple forums – and not just one-off spats, but extended back-and-forth over months. I did a lot of reflecting and reading and remixing and journalling for 15+ years. I got married young and it was important to me to have a happy marriage, and that was a lot of work that I think made me wiser still. I got lucky that my first boss at my first real job was an excellent mentor, who functioned as an uncommonly effective therapist-coach figure for me, helping me and challenging me to work through my personal problems. Our conversations over 5+ years made me both a sharper thinker and a more effective agent. I became more sensitive to constraints, bottlenecks, I sought to understand complex systems. Honestly, I watched a lot of TED talks – people are dismissive of them but some of them were really good! I read a bunch of biographies. And I talked with as many people as I could.
(2) To restate “what is the process” – I hope I demonstrated some of it above – I basically try to function as an inquisitive mirror. I ask people questions with genuine curiosity and interest, and I get them talking about themselves. And I actually pay attention, I actually listen. I look for tension, I look for hesitation, I look for confusion, I look for coercion and shoulds. And then I gently tap and touch around that, asking questions, being sensitive to how they’re feeling. If you look up a video of how people handle scared dogs, it’s kind of like a verbal version of that.
It also definitely helps that I have this vast repository of information in my mind – eg in this conversation I brought up the problem of Ikigai, and talked about Beyoncé and Apple – but I bring up different things in different conversations, depending on what comes up, whatever is relevant, whatever is interesting. I don’t plan these things ahead of time, I just feel it out and improvise. Part of why I love tweeting so much is that there’s an inexhaustible source of material for me to riff with and respond to.
The dynamism problem
The other thing I’m thinking is that I want to talk about my idea of “dynamism”. This might be better saved for the topic of another essay, but let’s just drop a couple of paragraphs about it and call it a night for now. When I talk about dynamism, I’m talking about versatility, resilience, the ability to move, to change, to drop something here and pick up something new there. Dynamic as opposed to static.
A big chunk of Introspect talks about “going from a static to a dynamic self-image”. A static self-image is a source of pain, it’s something that you have to contort to fit into. The Propaganda Department of the Self would love for you to fit a perfect static image. It’s simple, convenient, memorable, easy to communicate, and wrong.
We are dynamic beings. Even the word “human being” implies dynamism in it. Movement. We are always growing, always changing, never static. But somehow we’re not very good at it. We’re not quite educated properly. We’re conditioned and socialized in ways that are optimized for the throughput of the overall system, not for the flourishing of individuals. There are historical reasons for why this was the case, but we can and should continue to strive to do better. I’ll get into these things in more details in subsequent essays.
Here’s a relevant section from an unpublished draft (about writing good comments), where I ended up digressing and talking about the dynamism problem:
“From time to time people ask me to write something more substantial about how to do good replies, but I’ve always kinda procrastinated on it partially because, a bunch of it seems kinda obvious and trite, and a bunch of it requires dynamism— which is hard to put into words, since people will then copy the letter of your suggestions rather than the spirit of it. I think my main hesitation to write something about this has been because of the dynamism problem.
Actually maybe all of my essay drafts remain locked up behind the dynamism problem. If I can figure out how to communicate the idea of dynamism more dynamically such that people will actually follow the spirit rather than the letter, then I would be happy to publish. Huh, fuck, this might succinctly express the single main thing I have been chewing on for the past year. How to convey dynamism?? Storytelling obviously is a big part of it. But anyway this is supposed to be a draft about doing good comments so maybe the dynamism thing will have to wait for another essay.”
Maybe I’ll end up alluding to it in drips and drabs over a series of other essays. That wouldn’t be the worst possible outcome! Whatever gets me moving, I think. And that in itself is sort of the dynamic way: if the primary goal of “write a good essay about X” doesn’t work, it’s worth reorienting and asking questions like, “well, what’s the point of writing about X? what other ways can we achieve that goal?” and so on. And you see how this reorienting, rephrasing, restructuring, remixing process also applies to questions of identity, and meaning, and happiness.
Further reading / footnotes:
On “figuring out what you want”, I actually think that whole question is misframed. Thread on that here.
Here’s another thread about DMs I get from people. I talk about grandiosity and catastrophizing, and how wack it is that people feel so unheard and unseen in their lives that that they will seek out internet strangers, and entrust them with their deepest secrets.
Here’s a draft about The Dynamism Problem, that I don’t recommend reading because it’s a mess. Unless you’re interested in seeing what my unfinished messed up drafts look like. If you do read it though, leave me some thoughts, questions etc in the comments here; that would be really helpful.
One thing I’m thinking is that I should do more “maps” of these conversations. Or even just write up more essays, posts, documents about past conversations. I’m just saying that out loud right now as an intention.
I feel like I oughta say somewhere that I do take on clients – primarily for marketing consulting, but a couple of people have hired me just to talk through problems, and that’s been quite fruitful. I might write an essay soon about “how I help my clients”, which has a lot of parallels with how I help random strangers who show up in my DMs.