In about September 2025, I decided to go on a self-help kick, mostly revolving around stuff like “self-esteem”, “confidence”, and “guilt/shame”.

Basically, I wanted to no longer feel bad about myself (when unwarranted).

This has been working really well. In fact, I almost want to say I’m “done”, though I think it’s probably too early to be sure.

I wanted to log what’s been working for me, in case any of it is helpful or generalizable to other people.

Feel entirely free to skip this post if you’re not interested in the gooey details of my psyche.

On the other hand, I don’t actually believe that self-help is a shameful or uninteresting topic. How to handle your own psychology is a huge part of doing anything. And while my Substack isn’t mostly about me, it is something of a record of the things I’ve been interested in or working on at any given point, to the extent I’m free to talk about them in public. Self-help has been one of my “projects” lately, and I finally feel like I have justified, grounded opinions worth sharing about what works and what doesn’t (for me).

Thingness

A crucial heuristic I use for self-help is “thingness”, which is a bit hard to explain.

“Have you really had a breakthrough or not?” is a tough question — sometimes the feeling of “breakthrough” doesn’t last and you go right back to your old habits. But it takes a really long time to assess that you’ve made publicly demonstrable, long-term progress. So what are some early signals that something is fruitful?

Introspectively, I need to experience some kind of discrete, unambiguous change; a new thought or state, a place I can tell I’ve literally never been before in my life. “Change” doesn’t imply “permanent change”, but lots of self-help doesn’t even pass the sniff test of “whether you can prove it to a third party or not, but being 100% honest with yourself, did you feel anything clear-cut happen inside you?”

For instance, I don’t believe IFS has “thingness”, at least not for me. I went into that trance state, came up with a bunch of “parts”, wrote them down, and then even a few months later looked back at my writing and was like “what? heck no, i don’t have those as sub-personalities”. Stable sub-personalities just don’t seem like “natural categories” for describing what’s going on inside me, and nothing particularly changes or improves when I try on that conceptualization. There’s no “thingness.”

Usually, “mere intellectualization” doesn’t have that property of “thingness”. It’s “just” words and ideas and it doesn’t click into your more basic emotional, behavioral, or motivational systems. But I’ve found that if you go back and forth between intellectually analyzing and emotionally/bodily “feeling into” ideas, then even rather abstract concepts can create that discrete “click” of change, that chunky “thingness”.

Years ago, I used to think “goals” were also sort of a “wrong concept” for what was going on inside me — too abstract, too removed from the roiling chaos of raw sensation and semi-raw impulse, and thus talking about “my goals” would always be in some sense fake — but now I’ve changed so that goals are actually closer to being bona fide parts of my inner machinery, so goal-oriented paradigms work much better for me. They “have thingness” for me now, though they didn’t earlier.

The following insights and tactics, which came in part from me, in part from talking to a lot of (both customized and default) LLM bots, and in part from talking to a few friends, are, I’m pretty confident, “actual things” in the sense I’ve been talking about. How big and how long-term an impact they’ll have on my life remains to be seen, but I’m optimistic.

Insight #1: (Irrational) Guilt Is Actually Due To Fear Of Facing Someone’s Disapproval

This sounds pretty obvious, but it’s not. It’s a claim about what’s the cause and what’s the effect (and therefore what’s the right point to intervene).

One could imagine an equally plausible statement that reverses the cause and effect — “You only feel afraid of other people’s opinion because you have low self-esteem” — but I think that, at least for me, that would be false.

The causality definitely goes {fear of a bad social reaction} → {beating up myself preemptively, as a defense mechanism}.

Why am I so confident of this?

Well, first of all, the fear is a very concrete, physical flinch reaction. I get startled easily when someone comes in the room and “catches” me goofing off, for instance. That feels very concrete and basic, close to the “bare metal” of the body and mind. Whereas “self-esteem” seems a lot more complex and cognitive, and a lot more unclear what it even means.

Secondly, I can notice a certain “soothing” effect from self-condemnatory thoughts like “I’m a terrible person.” I feel a tension, which is relieved when I denigrate myself. That’s suggestive that my “low self esteem” is a strategy that I instinctively reach for to solve some other problem, rather than a “primary” phenomenon.

This is great news, because it suggests a tactic.

Tactic #1: DIY Exposure Therapy for Social Disapproval

There’s a known, evidence-based way to deal with phobias: graded exposure therapy! You start with the mildest version of the thing that triggers fear, and then sit with it until the fear goes away.

For me, this means vividly visualizing the experience of the person in front of me showing disapproval of the thing I say or do.

I’m pretty sensitive about social disapproval, so even simulated/imagined “exposure therapy” is productive for me. I can get a lot out of going through a mental “journey” where I imagine that someone whose opinion I care about has a negative reaction to what I’m doing, and simulate how I’d react and what would happen afterward, and find that it turns out okay.

“Mere” imagination is a bigger deal than most people think. Vivid, wholehearted imagination can do a lot of work towards allowing me to do new things in real life. I’ve been able to have conversations I was afraid of, simply by imagining them vividly ahead of time.

A real-life version of this exposure therapy I’ve also found useful is just making myself look at another person’s face, look into their eyes, and become highly aware of whether they seem to be “okay with me.”

Are they happy I’m here, with them, right now? Do they like what’s going on in the conversation?

The answer could be no!

Would I be able to mentally tolerate it, to not flinch away, if the truth was “actually I’m impatient for you to go/annoyed by what you just said/not a big fan of yours in general”?

The handful of times I’ve gotten into a state where I’m really prepared to see the truth whatever it may be — not defending against the worst-case scenario or bracing for it or distracting myself from it, but actually okay with it — it’s a strange, intense, hyper-present altered state, and really conducive to heightened intimacy and warmth.

It’s not possible to fully feel that someone likes you unless you are fully open to the possibility that they don’t. Once that “fluttering” of anxiety “stabilizes”, once the flinchy zapping around of your mind settles down into calm, some very odd (and good) things start to happen.

I actually haven’t done this tactic that often and I think there’s still a lot of room for improvement, but the experiences I’ve had have convinced me that it’s fruitful.

Tactic #2: Positive Exposure Therapy

There are some things — often they’re compliments people have given me — where thinking about them gives me a sense of mingled fear and excitement. Sort of like “it can’t be!!!” vibrating against “but wouldn’t it be wonderful???”

You can do exposure therapy against these things too. It’s an unusually fun and rewarding process, because you’re increasing your tolerance for an intensely pleasant stimulus. The end result is you keep the excitement but extinguish the fear.

You just keep going back and forth between your fearful “but it can’t be this good!!!” reaction and a calm “yes, it can, because XYZ, this is actually perfectly normal and comprehensible” perspective, until you can sort of hold both at the same time, and you watch the fear burning itself out like a guttering candle.

If you ever have a “special interest” that gets you so excited that you get overwhelmed and can’t talk about it, and you want to be able to “be normal” about it without losing your enthusiasm, that’s another candidate for positive exposure therapy.

Among other things, positive exposure therapy got me to:

Insight #2: It Is Good That I Have Wants/Desires/Choices/Opinions/Etc

One of the things I’ve historically felt bad about is that I’m not particularly self-effacing; I want stuff, I go after what I want, I have a lot of opinions, etc. I’ve been accused that “You just do as you damn well please,” and it’s not wrong.

And in the past, a big part of me would feel “it’s impossible for me to be a good person; I’m tainted with this willful nature!”

On the other hand, you could also describe this trait as motivation. Motivation, arguably, is essential for goodness. Anything valuable or worthwhile in this world is ultimately produced by people who are personally motivated towards it. So there can’t be anything wrong with the mere fact of having one’s own motivations!

And I have met people who thought my motivation was an admirable trait.

On some level I even have to admit that I like my will and always have. It is me, after all; how could I not?

So a few rounds of back-and-forth with positive exposure therapy got me comfortable with the idea that I’m a person with will/motivation/desire/etc and that this is a good thing.

Tactic #3: Positive Visualization

I got this one from my friend Stephen Long, who’s a life coach.

Before you do a high-stakes or difficult thing, you literally visualize it going as well as possible. Vividly. In detail.

This helps a lot with coming into meetings with the kind of attitude that makes them more likely to go well.

It also helps with motivation issues. When I procrastinate, often it’s simply because I haven’t taken a moment to think through how I want/intend the thing to go, or because I anticipate something going wrong. (“I’ll show up at the DMV and there’ll be some kind of mysterious bureaucratic snag that keeps me from getting my ID card” → I never get around to going to the DMV). If instead I visualize “I’m going to do A, then B, then C, and they’re all going to go smoothly and painlessly” then I often find I’m eager to get started.

Positive visualization isn’t magical thinking like “if you imagine winning the lottery, you will win the lottery.”

It’s more like planning, but in the sense of “motor planning”, the kind of vivid inner simulation that connects directly to behavioral output.

I find it entirely believable, for instance, that if a basketball player vividly imagines shooting the ball into the hoop, he’s more likely to make the next basket. He has real-life experience with both making and missing baskets, and he’s choosing to simulate (and prepare for) the motor path that in his experience actually leads to making more baskets.

Likewise, if I vividly visualize a meeting going well, I’m visualizing myself behaving in ways that, in the past, I’ve behaved when meetings did go well. If I visualize myself going to the DMV, I’m drawing from experiences when going to a new location and filling out forms did go smoothly. If you do it in a well-grounded way, derived from your own real-world experience (and vividness will help with that), imagining good outcomes is effectively planning to behave in ways that, in your experience, tend to lead to good outcomes.

This post is also a good woo-free explanation of why “manifestation” can work. People help you more, and you are more motivated and creative, when you know what you want and focus on it.

Positive visualization is arguably the generalization of both “positive” and “negative” exposure therapy; if you’re habitually too pessimistic, you force your imagination to engage with the possibility of things being really good — or the possibility that they’ll go “wrong” in some way you’re afraid of, but that you’ll survive just fine.

Insight #3: The God’s-Eye View Is Fake; Only The First-Person Perspective Is Real

In order to fix emotional and practical problems, sometimes I think you have to venture into the philosophical realm.

I’d historically had a problem with being overly dependent on external validation (praise and criticism). And when I introspected about it, it was because I didn’t feel I had access to what was “really” good or not, but other people might. It was if I were trying to peer into some invisible realm that was akin to “what God’s opinion would be” or “the universe’s-eye view”: an inherent, eternal judge of what “counted” as sufficiently good or not. But I couldn’t see into that “realm” of Platonic essences myself, so I could only hope that other people had access to it.

Now, if you don’t believe in the supernatural, and you don’t believe that other people are somehow fundamentally or ontologically superior to yourself, then this doesn’t make any sense.

Why should someone else’s opinion of me matter, while my own opinion is meaningless? What have they got that I haven’t?

And if ordinary logical thinking is insufficient to access the True Universal Right Answers, why is trying to “peer into the void” with intuition any better?

How do I know that anybody has access to the True Universal Right Answers? Or that they even exist?

But there’s a real psychological need here, which I don’t think people can do without, for non-arbitrary, non-trivial, reachable standards.

On some level I wanted my standards to be non-arbitrary — for instance, I’d only want to feel pride if I had really done something worth being proud of.

On the other hand, no standard I came up with seemed “legit” enough to qualify as “really worth being proud of” — since it was tainted with my choices, my judgment calls, and of course I’m fallible.

But on the other other hand, “then you just never get to fully feel proud of yourself; everything is provisional” was unsatisfying. There are people, I know, who believe in this sort of eternal dissatisfaction on principle; and I don’t envy the unhappiness and chronic exhaustion that tends to build up in their lives.

I’ve always needed a “win condition”. I need to know it’s possible, even if only someday at the end of my life, to be confident and secure in the feeling that I’ve done a good job. I’m fond of triumph, of trumpet fanfares and celebrations, and I need to believe that under some conditions, if I did certain sufficiently awesome things, I’d have earned a triumphant celebration. A glorious state, free of worry, completely exultant. And, as a more immediately practical matter, I need conditions under which I’d let myself completely physically relax — constant straining literally hurts my back.

I don’t think I’m unique here. People need it to be possible to “win”, and they need the “win condition” to be a real challenge that really means something, something they can take seriously as deserving of pride and celebration; if it’s too much like a “participation trophy” it won’t work.

But I’d wound up with some implicit beliefs that made it impossible for me to judge on my own that anything attainable in the real world “counted as a win” for me.

So I had resorted to the much less rigorous default “strategy” of feeling elated when other people praised me and deflated when they criticized me, almost regardless of how credible I actually found them.

The big insight was deciding that I could do better by deciding on some halfway reasonable criteria for what I care about, and then observe empirically whether I’m meeting my own standards.

And then, I could just choose not to worry any more about the “God’s eye view” and whether I’m congenitally “blind” to it. I could just take a first person perspective, a Sarah’s-eye view, all the time; go about my business, pursue my goals, measure my success by whether I’m meeting them.

Sure, I’m the one picking my goals, so I could have just picked trivial ones. But I’m not going to do that. I’m going to pick goals that reflect my best judgment and whole self, such that I wouldn’t later on expect to regret “letting myself” fully relax and celebrate after completing them, or “letting myself” fully believe they’re a big deal.

“Your own best effort at making reasonable judgment calls” isn’t infallible, but it’s clearly better (and more grounded in reference to reality, i.e. genuinely closer to truth and objectivity) than the patterns you’ll fall into if you insist that your own best effort can never be good enough.

This leads into a new tactic.

Tactic #4: Self-Evaluation

Yes, it’s possible to do an honest self-evaluation, that is actually more credible, to you, than pretty much anybody else’s evaluation of you.

You evaluate “am I a good parent?” or “am I a good person” or “am I brave?” or “am I a good writer?” with pretty much the same procedure.

1. Think of some examples, of other people, and decide how you’d classify them. Would I say that, on the whole, George Washington led a good life? My mother? Think of clear-cut “yes” and “no” examples, and ambiguous cases.

2. Based on these examples, notice what sub-criteria you’re considering as important to your understanding of “a good person”, “a good piece of writing”, “good parenting”, etc.

3. Identify what population it seems reasonable to compare yourself to.
   For instance, as a writer, I’m comparing myself to the set of people who have blogs, or who write a substantial amount for work; it would be cold comfort to know I’m a “better writer” than a five-year-old or someone who never had access to an education. As a parent, I’m primarily comparing myself to my friends and acquaintances with kids, my kids’ classmates’ parents, and to some extent my own parents and my peers’ parents.

4. On each sub-criterion, try to think fairly about how you stack up compared to your reference population.

On each of these steps, you’re necessarily making debatable judgment calls. You don’t know you’re getting the “right answer” in the same way you know 2+2=4. It’s not a turn-the-crank algorithm.

But it’s also a structured process. You’re building a narrative that hangs on a number of facts. You’re sincerely trying to give a measured best-guess estimate of your performance, and you’re breaking that down into enough small pieces that you can think about them somewhat concretely.

It’s a lot better than “I’m in a bad mood and I just saw a negative Internet comment so I think I’m a bad person.”

In fact, it’s probably a lot better — stabler, more grounded in knowledge about your life, more consonant with your long-term priorities — than most other people’s impressions of you can possibly be.

Having done self-evaluations and knowing they’re possible, I no longer feel at all like there’s an open question or anything mysterious about “am I any good?” or “do I deserve to be proud of myself?” I have justified opinions of my own about the matter.

I can still be surprised by other people’s evaluations of me — e.g. when an expert says I’m qualified for some kind of job that I had honestly believed I wasn’t — but even when that happens, my old opinion wasn’t based on nothing, it was just based on a limited set of facts that apparently didn’t include the full picture.

I doubt I’m immune yet to emotional (over)reactions to praise and criticism, but something feels like it’s fundamentally changed here. Other people are no longer my only source of trusted guidance about how I’m doing. My closest approximation to “ground truth” is, instead, something I build myself.