A need to “prove oneself” to internalized authority figures leads to things like climbing conventional status ladders, or staying in an unhappy marriage, or piling up as much money as possible to preserve the appearance of having “made it”.

What motivated Esther to do things like take a receptionist job at a film company, pick up her life and move to San Francisco, and risk her savings on her startup was something far more personal and idiosyncratic: a conception of the interests she wanted to explore, the people she wanted to meet, the products she wanted to create, the life she envisioned and wanted to build for herself—and, yes, the proof that she really could count on herself to do it.

This is super inspiring on so many levels.

It seems like life becomes a little more palatable once you figure out who you are and start leaning into that.

So then I asked him: what kind of VC does he actually want on his cap table (that is, owning a portion of his company)? What would be true of the sort of investor who really gets him and resonates with what he’s building?

The same question applies here as on a first date, I pointed out: do you want them to fall in love with you, or with a fake version of you that you now either have to maintain—at the expense of the person you actually are and want to be—or else face irreconcilable conflict and disapproval when you finally drop the facade?

You want to reach the investors in the room who want to flame-spot audacious and idealistic young upstarts like you; who’ve staked their careers and reputations on the thesis that the world needs more of just the kind of company you’re building; who resonate so hard with your story and are so wowed by your talent that they’ll be willing to invest in, nurture, and protect your agency as a founder.

One can of course relate to money in pathological ways. For those whose standard of value resides not in a conception of their fully-lived life (a la the builder), but in the impressions or judgments of others (be it God or society or their parents or some other “drill sergeant”), money means whatever it purportedly means to those others—status, in some circles, or wicked materialism in others, or in still others, “privilege” to be forgiven with obligate philanthropy. 

By contrast, a builder’s relationship to money is not mediated by any of these external intermediaries. She understands that money is a medium of value exchange, and what she values is set by the life she wants to build and the world she wants to live in. 

There are also simpler pathologies, such as when fear or insecurity drives founders to pursue short-term monetary gains over the longer-term health and durability of their business. But such financial anxieties can be diagnosed and remedied by re-orienting toward the overarching goal of building one’s best life, which presumably includes a healthy and durable version of one’s business (or whatever one is building) as part of it.

Quite a useful way to reframe money and its importance to a well considered life.

Both the “drill sergeant” and the “Zen master” mindset share a common underlying worldview on which our lives do not fully belong to us, in that we have relatively little agency over the goals we set and the means by which we pursue them.

The “builder’s mindset,” by contrast, flows from a qualitatively different and deeply countercultural worldview: one on which all of our efforts can and ought to be organized around the ultimate goal of building and enjoying our own best life.

My goodness, this hits me right in my feels.

I’ve been absolutely obsessed with reading Gena Gorlin’s work lately. Several of her articles have deeply resonated with me.

I’m gonna share this passage as well, because again, as I aim to come up with some sort of tangible list of values, this will be helpful:

The “builder’s mindset” represents a fundamentally different set of underlying core assumptions about the kinds of beings we are, what we can do, and what is worth doing, compared to the other mindsets. This includes:

1. The view that we are rational agents capable of and responsible for shaping the natural world according to our needs (i.e., of building).

2. The view that exercising one’s agency to build one’s own fully-lived life is a self-sufficient end goal, needing no further justification or permission.

3. A primary motivation by love and values, rather than fear.

4. The view that human relationships are necessarily win-win, not win-lose or lose-win.

For point number one, she even references my favorite Steve Jobs quote. I mean, come on… this article was tailor made just for me.

A lot of therapy and coaching clients I've worked with are initially very preoccupied with some issue that has been a major blocker in their life. Maybe they’re very socially anxious, or depressed, or they’ve suffered a lot of trauma. And the pattern is that they organize their lives and identities around these very real problems in a way that precludes them from actually, really living. A common example is the client who says “I can’t start dating until after I’ve fixed my social anxiety,” or “I can’t apply for these really ambitious jobs until after I’ve fixed my depression”; so they identify their dysfunctional behavior patterns and process their feelings and pick up new self-care frameworks from one therapist or self-help guru after another, all the while stalling in their career or romantic life. What they often don’t realize is how easily this “shadow work” can itself become a coping mechanism to avoid the harder work of actually going out and living their best lives. 

To their great credit, these clients are usually quick to get on board with the idea that every effective social anxiety treatment involves exposure therapy (e.g., going on a bunch of awkward dates!) and every effective depression treatment involves re-engaging in valued activities (e.g., doing challenging work!), once I present it to them. But what I often find is that there is still something subtly “off” about their internalized approach to these tasks: like they’re not going out and living their best life but rather just doing more shadow work. For instance, they might go on a date and then report back about how well or poorly they managed their anxiety or their negative self-talk; but I don’t hear much about how much they liked or connected with the other person. Or they might describe the coping strategies they used to “get through” a job interview, but I don’t get the sense that they showcased any of the passion and brilliance with which I’ve sometimes heard them riff on their most ambitious technical projects.  Not too surprisingly, they tend to get middling romantic and professional outcomes with this approach, which further reinforces their “I’m broken and need fixing” mentality. 

To really unlock their full flourishing, I find that these clients need a more fundamental paradigm shift: from “I’m broken, how do I fix myself?” to “This is my one precious life, how do I make it awesome?” Once they are looking through this lens, they may well still decide to work on their social awkwardness or their proneness to depression—or they may decide to invest their energy in other, higher-leverage endeavors, drawing inspiration from the many socially awkward and depression-prone individuals (from Ella Fitzgerald to Abraham Lincoln, respectively) who nonetheless lived unambiguously awesome lives.

I came across Dr. Gena Gorlin while doing research on the intersection of psychology and AI, but these three paragraphs from her most recent newsletter were an unexpected kick in the pants for a different problem I’ve been working on.

I don’t necessarily need to “fix” my depression and anxiety. I need to ameliorate their symptoms to the point where I can resume experiencing the joys that come with living life.

"You become more resilient, and your body learns that the anxiety and stress isn't needed because there is no threat to losing anything when there's always more ways to gain what you want or need," says Papetti. "The only thing that's certain in life is uncertainty, so embodying an abundance mindset that trusts you'll be safe in the uncertainty is the secret to living a life of greater gratitude, ease, and satisfaction." 

Great advice in here for helping you to adjust your mindset. The journaling tip and the celebrating the wins of others tip are resonating with me as of late.