1

Part way through my second year of college, I realized that I didn't want to continue my relationship with my current girlfriend.

We had been dating for about a year. I liked her quite a bit and enjoyed her company, but the relationship was growing asymmetric: she wanted to get more serious, and I was restless.

By chance, we happened to live down the hall from each other. We shared a friend group. Breaking up would have been awkward, and continuing the relationship was quite convenient.

Perhaps most importantly, I didn't want to hurt this girl: she was a good person, I had quite a bit of affection for her, and my restlessness was not due to her flaws but to my temperament. I didn't know how to tell her the reasons why I didn't want to get more serious without deeply hurting her.

So here's what I did: I knew that I was going to study abroad in my third year of college, and partway through my second year, I made it very clear that I wanted to break up at the end of our second year. In my third year, I would be studying abroad, and saying that I didn't want a long-distance relationship was a gentle excuse. It was a fine Schelling point, a convenient way to avoid listing the reasons why she couldn't fulfill my needs. I wanted to avoid all the awkwardness and pain—and all I needed to do was pretend to enjoy a relationship for about six months.

You can probably guess how this ended.

Our relationship grew more strained. My affection started fading, so I faked more affection than I had, and this soured the affection that remained. She sensed that something was wrong, and made increasingly desperate attempts to connect. I grew disgusted with her inability to see through the charade even as I kept it going, as she struggled to heal a relationship that I insisted wasn't broken while subconsciously signalling that it was.

I told myself that I just needed to make it to the end of the school year.

The end of the school year finally arrived, and on the last day of classes—the day we were supposed to break up—she had a surprise for me.

She'd gotten accepted to the same study-abroad program as me, and would be coming along. We didn't have to break up.

What followed was one of the most difficult conversations I've ever shared. I broke up with her, and I can assure you that the pain and awkwardness that I hoped to avoid with my clever plan was realized tenfold.

On that day, I vowed to never again shy away from Forbidden Conversations.

Forbidden Conversations are those conversations that you just can't have, because they're too awkward. Think of a specific person close to you—a parent, a partner, a boss. Is there something you're hiding from them? Is there a conversation topic that you steer away from? Is there a revelation that you flinch to consider them learning? It is that mental flinch which demarcates a forbidden conversation.

Do you ever find yourself pausing a moment to remember what version of the truth you're supposed to be presenting to this person; which white lies they believe that you musn't displace? That pause demarcates a forbidden conversation.

Forbidden conversations are conversations where the very idea of having the conversation feels bad. They are the conversations that you automatically steer away from without thinking about it. Have you ever noticed yourself talking the conversation away from a dangerous subject? That's a sign of forbidden conversations. Have you ever noticed yourself supressing an urge to tell someone something? Forbidden conversation.

Sometimes forbidden conversations are small and inconsequential. In the hyperbole and a half book, Allie Brosh talks about how, after one incident involving drinking lots of hot sauce as a child, her family became convinced that she really loved hot sauce. They bought her hot-sauce-related gifts for decades. She didn't really like hot sauce, but never corrected her family, and so the misconception grew. It's easy to let those little misconceptions grow until others think that they are part of your core identity. Correcting a misconception never seems like an option, never seems like the thing to do in the moment: that conversation is too awkward, the mind skirts around the possibility.

Sometimes, these little uncorrected misconceptions can spiral out of control, and can seriously damage relationships. (I'm under the impression that this phenomenon drove many episodes of Seinfeld.) One of my friends feels like they have to pretend to be someone else when in the presence of their parents, and resents the charade—and I don't think that this experience is uncommon.

If the trivial forbidden conversations can cause longstanding relationship harm, imagine how much havoc has been wreaked by the nontrivial forbidden conversations.

I once thought it was a really good idea to sacrifice six months worth of two people's happiness in order to postpone an awkward break-up.

And I expect that, measured against the standard amount of time and resources lost in attempts to avoid awkward conversations, six months is nothing.

This is one of the primary altars upon which I see people sacrifice their agency: humans are social creatures, and it can be extremely difficult to go against the perceived social grain, even if only briefly.

2

One of the easiest ways to become more agentic is to train yourself to steer towards the forbidden conversations, rather than away from them.

Steering towards forbidden conversations is difficult, but I might be able to help by providing a few pieces of information.

The first is empirical: after having a great many Forbidden Conversations on purpose, I can happily tell you that they have only ever served me well. Having these conversations was very difficult, at first: my hindbrain would scream that the conversations were BAD, and pump my veins full of adrenaline while my mind searched frantically for excuses to delay the conversation until some other time. I'd have to manually force the words ("let's talk about our relationship," or something) through my lips.

However, in almost every case, having these conversations was not only less-bad-than-expected. These conversations proved actively good. I've spent the last few years actively steering towards the taboo parts of conversations, and this has served me well.

But stories convey this better than words, so allow me a few anecdotes:

In my final year of college, I took a government contract: they paid my tuition and gave me a job, and for each course hour that they paid for, I had to work three hours at the job. I started working for them during the school year, and it was going to take me until late October of 2011 before I was contractually allowed to quit. Afterwards, I was planning to take a programming job with one of the big tech firms.

Part way through the school year, I got a job offer from one of those big tech firms. I hadn't been aware of quite how much the big tech firms were willing to pay for good programmers: they offered about double my government salary. They offered so much more money that, if I worked for them instead of the government from May to October, the difference more than covered the cost of breaking the contract.

This presented me with a choice. The government job bored me, it paid less, and while the cause was good, the job was not a place where I was having a high impact.

But the idea of breaking my contract was Forbidden. The very idea was dreadful. I thought my boss would take it as a betrayal. I was the only programmer on a team of economists, and losing me would be a large blow. I expected disapproval and disappointment, I expected others to think less of me. It would have been so easy to go with the flow, to finish out my contract, at the cost of only four months of boredom.

But I had vowed not to avoid forbidden conversations, and so I dragged myself into my boss' office and talked about it.

I told him I had another offer. I told him how much they were paying. I told him I wanted to break the contract and leave early. And you know what? He took it really well. He wasn't betrayed in the slightest. He just sighed and said "I knew we wouldn't be able to hold on to you forever," and lamented that NIST couldn't offer a comparable salary. We parted ways on good terms.

Later, I joined a tech startup.

Nine days later, it became clear that this startup wasn't for me. I brought the CEO up to the rooftop for a chat. I quit on the spot.

Again, I had dreaded the conversation. Again, it turned out to be easy. The CEO thanked me for my honesty, knowing as well as I did that it would have been poisonous for me to stay and fake my loyalty. Afterwards, he spoke highly of my honesty and initiative, and offered glowing recommendations. We parted ways on good terms.

3

The point isn't just that the forbidden conversations don't go as badly as you expect. The point is that, most of the time, they are net good.

My former employers appreciated knowing that their jobs were not for me. They may have preferred a world in which I was deeply engaged in the work they offered; but given that that was not the real world, they preferred candor to feigned interest.

In my experience, this principle generalizes: in almost all cases when I've had a forbidden conversation, my conversation partner has thanked me afterwards.

This is the most powerful tool that I can give you if you want to gain the ability to have all those forbidden conversations: to stop being slave to social circumstance, first install a part of yourself that enjoys aversive conversations.

As with many rationality techniques, steering towards forbidden conversations will require both noticing and practice. But there is a step that comes before that, and that is the part here you start wanting to have the forbidden conversations, on a subconscious level.

I still experience a sense of doom and adrenaline before having those really hard conversations. The difference, now, is that I like that feeling.

Now, having a forbidden conversation feels to me like a cross between the feeling you get right before you rip off a band-aid and the feeling you get right before getting on a roller coaster. There's still anticipation, but it's a fun anticipation, a healthy anticipation.

If you can make taboo topics seem fun and healthy at a subconscious level, then it will be much easier to notice and approach. (Don't spend conscious effort on things that you can get your subconscious to do automatically!)

The forbidden conversations are where all the fun is! Taboo topics are the fast track to connection and bonding. They are shortcuts that allow you to avoid the usual period of social awkwardness and help you get to know people better.

Sometimes, taboo topics are symmetric: everybody in the room is avoiding the same Forbidden Conversation. This is so common that we have an idiom for it: "an elephant in the room." The ability to actually point out the elephants in the room is incredibly rare, and there's a deep pleasure associated with it.

Imagine you've gotten in trouble at school, and your parents know it, but they don't know that you know they know it. Imagine the dinner conversation where they're treading lightly around the topic, but acting all flustered. Imagine watching all their concerned bustling and saying, "so, want to talk about [that prank I pulled]?" The immediate sense is one of relief.

Or imagine three people in a room, all somewhat unsure of where the sexual tension lies, all darting furtive glances at each other, none of them daring to address the topic: there's a delicious anticipation associated with this scenario, if you know how to spark the Forbidden Conversation in a way that doesn't kill the tension. Being able to point out the elephants in the room is a service, and a valuable one at that.

Even when Forbidden Conversations are asymmetric—such as when someone has deep misconceptions about your person—it's usually the case that other people have their own taboo topics that their minds refuse to notice until you set up a conversation context where forbidden contexts are allowed. More than once, after broaching a forbidden topic, people have reacted with relief, thanked me, and then cleared up half a dozen important misconceptions that I had about them that they'd been unable to tell me about beforehand.

Sometimes, when faced with a forbidden conversation, I like to think of my life as a story. You know those times when a character in a drama is avoiding a crucial conversation? When a miscommunication has occurred, and the character is too stubborn to have the simple conversation that will prevent a whole lot of suffering?

Think of a moment where you've wanted to shout at a character for avoiding a conversation, where you've wanted to cry something like "just tell them!" Think Kvothe & Denna in the Kingkiller Chronicles, Simon & Kalee in Firefly, Ginny Weasley talking about the diary in Chamber of Secrets, and so on. (See also the Can Not Spit It Out trope.)

This is what a forbidden conversation looks like from the outside.

The conversations that you dread, that you're sure will hurt someone, that seem far too awkward, that your mind ignores so thoroughly that the conversation becomes difficult to think about: those are the conversations that readers of your life would be shouting about.

And I don't know about you, but I get a kick out of being genre-savvy, about avoiding mistakes that all readers of my life would be yelling at me to avoid.

The forbidden conversations are where the plot advances. They are the parts where you get to leave a job you don't like, or where you get to forge the strongest friendships, or where you get to expose a relationship to the light of truth and see what happens. The forbidden conversations are the parts where you tell someone what you really think of them, where you drop the façades, where you finally get to say what you've been dying to say for all those months or years.

They're the fun parts.

So I've installed a part of myself that sits in one corner of my mind, and keeps an eye out for the forbidden conversations. Then, when I feel the impulse to flinch away from a conversation, this part of me says "Ah, yes. Yes, this is going to be one of the good parts. I'll go pop the popcorn."

4

By default, people tend to shy away from taboo topics. Before I actively decided to steer towards hard conversations, I avoided them without even thinking about it. This sometimes happened to an absurd degree: people would misinterpret me, and I'd feel a compulsion to go along with the misinterpretation instead of correcting them. They'd mishear me and think I said I was born in New York, and it would feel too awkward to correct them, and then next time they were travelling to New York and asked me for suggestions about what to do, I'd feel compelled to find travel recommendations consistent with me growing up there, and the whole thing would snowball. I was slave to social dynamics: not because I explicitly decided that that was a fine plan, but because avoiding awkward conversations was reflexive. There were small notes of dissonance, but the answer was always "it's too late this time; I'll do better next time."

It took conscious effort to turn those small notes of discontent into powerful attractors. But now, my subconscious steers towards those awkward conversations, and this has proven valuable.

Brains are strange artifacts: I once thought it was a really good idea to sacrifice six months worth of two people's happiness in order to postpone an awkward break-up. Countless human hours, months, and years have been sacrificed in order to avoid those awkward, forbidden, taboo conversations.

So take the weakness, and make it your strength: There is a mental signal that occurs when you encounter a forbidden conversation, a flinch, an impulse tinged with dread. You can learn to notice that signal, and turn it into an attractor. You can flinch towards the forbidden conversations, you can anticipate the taboo topics with pleasure.

This will take effort and practice, but the first step is noticing that forbidden conversations are where the fun is.