We come into this world craving the presence of others. But a few modern trends—a sprawling built environment, the decline of church, social mobility that moves people away from friends and family—spread us out as adults in a way that invites disconnection. Meanwhile, as an evolutionary hangover from a more dangerous world, we are exquisitely engineered to pay attention to spectacle and catastrophe. But screens have replaced a chunk of our physical-world experience with a digital simulacrum that has enough spectacle and catastrophe to capture hours of our greedy attention. These devices so absorb us that it’s very difficult to engage with them and be present with other people.

The sum result of these trends is that we are both pushed and pulled toward a level of aloneness for which we are dysevolved and emotionally unprepared. Sartre said hell is other people. Perhaps. But the alternative is worse.

Ironically, this article was shared to me by one of the few people I see IRL nearly every week.

Paul, Micah, Nick, and I get together every Monday night and make music. It’s often the highlight of my week.

We get dinner beforehand and talk about the day to day goings on of our lives. Then, we retreat to Paul’s multi-million dollar recording studio ¹ and just noodle around.

We don’t have a set agenda, no prescribed musical style. One of us just starts playing something, and the rest of us join in.

No matter how depressed, anxious, or frustrated I feel walking into Paul’s house, I never leave with those feelings. Getting to spend time with three smart, talented, and caring dudes always leaves me with a filled bucket.²

Find an activity that brings you joy and go do it with other people. And if you don’t know where to find those people, just ask someone. That’s what Paul did, and thanks to him, I’ve now got two new friends and a weekly outlet for building my guitar skills and expressing some creativity.³

Upon returning from her lunch, my boss asked me to prep one more term packet.

“That poor soul,” I thought as I made my way to the HR supply closet to assemble another fateful folder.

I exited the supply closet, packet in hand, and walked over to my boss’s office in which she and the other HR manager were chatting. As was often the case.

Extending my arm, I reached across my manager’s desk to hand her the freshly prepped term kit. Her hands remained still. Folded on top of her desk.

“You can actually keep that one. That one is for you.”

This is cruelty on another level.

The main reason I’m sharing this is the suggestions Lauren makes after her layoff to find yourself outside of your profession.

It’s a big part of how I’ve spent the last two months since I got laid off. It’s really hard to undo not only 12 years of professional conditioning around the notion that “I am my job”, but also the 16 years of schooling before that which trains you to believe that other people will only value you for your profession.

In one of the job interviews I had this week, someone asked me, “how have you been spending the last two months?”

The only answer I could give was the honest one: “I’ve spent it dealing with my anxiety and depression.”

And while I can’t say I’ve beaten that stuff, things are definitely better. I also can say I’ve been enjoying playing with my kids, dating my wife, learning about AI, hanging out with likeminded nerds exploring AI, playing with new web development frameworks, making music in a band, catching up on TV, finding new ways to exercise (kickboxing and HIIT), and exploring philosophy.

It would be nice to have money coming in the door (and it would be doubly nice to have health insurance to help pay for therapy 😂), but I’m extremely grateful for the opportunity to figure out who I am again.

(For the record, my layoff story isn’t that dramatic. Layoffs are never easy for either side of the table, but they certainly don’t need to be made cruel.)

I ended my first blog detailing my job hunt with a request for insights or articles that speak to how AI might force us to define our humanity.

This op-ed in yesterday’s New York Times is exactly what I’ve been looking for.

[…] The big question emerging across so many conversations about A.I. and work: What are our core capabilities as humans?

If we answer that question from a place of fear about what’s left for people in the age of A.I., we can end up conceding a diminished view of human capability. Instead, it’s critical for us all to start from a place that imagines what’s possible for humans in the age of A.I. When you do that, you find yourself focusing quickly on people skills that allow us to collaborate and innovate in ways technology can amplify but never replace.

Herein lies the realization I’ve arrived at over the last two years of experimenting with large language models.

The real winners of large language models will be those who understand how to talk to them like you talk to a human.

Math and stats are two languages that most humans have a hard time understanding. The last few hundred years of advancements in those areas have led us to the creation of a tool which anyone can leverage as long as they know how to ask a good question. The logic/math skills are no longer the career differentiator that they have been since the dawn of the twentieth century.¹

The theory I'm working on looks something like this:

1. LLMs will become an important abstraction away from the complex math
2. With an abstraction like this, we will be able to solve problems like never before
3. We need to work together, utilizing all of our unique strengths, to be able to get the most out of these new abstractions

To illustrate what I mean, take the Python programming language as an example. When you write something in Python, that code is interpreted by something like CPython² , which then is compiled into machine/assembly code, which then gets translated to binary code, which finally results in the thing that gets run on those fancy M3 chips in your brand new Macbook Pro.

Programmers back in the day actually did have to write binary code. Those seem like the absolute dark days to me. It must've taken forever to create punch cards to feed into a system to perform the calculations.

Today, you can spin up a Python function in no time to perform incredibly complex calculations with ease.

LLMs, in many ways, provide us with a similar abstraction on top of our own communication methods as humans.

Just like the skills that were needed to write binary are not entirely gone³, LLMs won’t eliminate jobs; they’ll open up an entirely new way to do the work. The work itself is what we need to reimagine, and the training that will be needed is how we interact with these LLMs.

Fortunately⁴, the training here won’t be heavy on the logical/analytical side; rather, the skills we need will be those that we learn in kindergarten and hone throughout our life: how to pursuade and convince others, how to phrase questions clearly, how to provide enough detail (and the right kind of detail) to get a machine to understand your intent.

Really, this pullquote from the article sums it up beautifully:

Almost anticipating this exact moment a few years ago, Minouche Shafik, who is now the president of Columbia University, said: “In the past, jobs were about muscles. Now they’re about brains, but in the future, they’ll be about the heart.”

In my explorations of “sustainable business”, I'm often wondering what these two words really mean. I've previously shared some ponderings about the meaning of the word “sustainability”, but what about the word business?

It turns out that it is exactly what it sounds like. The word business originates from Northumbria where the old English word “bisignes” meant care, anxiety or occupation. This evolved into “busyness”, meaning a state of being occupied or engaged. In other words, a state of being busy.

This puts a whole new perspective on the term sustainable business and makes it feel like even more of an oxymoron. If sustainability is the ability to sustain something over the long term, then sustainable business would be to stay busy indefinitely.

Is that viable?

And more importantly, is that what we really want?

As always, Tom’s on point with this essay.

I’m working hard to reduce my wants. Sounds a bit like an oxymoron (no pun intended here), but we’ve all been so conditioned to chase after the shiny thing that we hardly ever stop to ask if the shiny thing is worth coveting.

And it’s really hard to not want to go after the shiny new thing. Getting laid off made it easy to not insta-buy a Vision Pro, but the hype leading up to its release sure got me intrigued.

I’m glad I didn’t, in retrospect, because the reviews aren’t exactly lighting the world on fire.

But this is just one of many examples I can give about being bit by the conspicuous consumption bug.

Another thought: nothing drives me more batty about a job than when you need to track your hours.

The hardest part for me is the obligatory feeling to maximize the time you are claiming you worked.

Let’s say I write down that I spent 8 hours building your website. One of those hours included a meeting where we spent half of it talking about how our weekends went. Ethically speaking, is it wrong for me to charge for an hour of that time, or should I actually say I worked 7.5 hours on your website that day?

Of course, writing this down, it feels silly. Everybody writes down 8 hours.

But if everybody does it, then why do we do it? What gain do we get by tracking our hours? Shouldn’t the final output matter more than how much effort went into building the thing? Is time a useful representation of effort?

I dunno… every time I read Tom’s posts, it feels like there should be a better way to orchestrate our economies. It’s probably time we figure out what symphonies we should be playing before we burn our planet to the ground in the name of growth.

I’d like to use “home” as the operative analogy for my own website.

With any analogy, you choose which properties of the subject to apply to the object of comparison, and which to ignore. What I find significant about homes in this context is that they don’t exist primarily for display: rather, they’re designed around the habits and values of their occupants.

Analogously, I want to use my website to order and document my own activity, and to interact with things and people that I care about.

Still, a website and a home are importantly different in that the former is intended for public exposure, whereas the latter is grounded in private life. But maybe we can relate the public nature of websites to a public dimension of homes: hosting visitors.

Typically we don’t show our house guests everything — we keep many things private and clean up before they arrive. Moreover, we’ve made prior decisions about our furniture and decor with future guests in mind. So homes can certainly be curated for the public eye; but crucially, they maintain their function as living spaces.

I find it generative to consider websites as a similar conjunction of public and private activity: by thinking about how visitors will receive the things that I publish, I’m compelled to produce more and refine the things that I make. At the same time, the website remains my space and is subservient to no other end.

The joy I get from tweaking my personal site and sharing links like this to it seems to be the exact same joy that my kids get out of meticulously organizing their playhouses.

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.

If somebody would’ve shown me this video when I was 12 or 13, I think computer programming would’ve been way easier for me to understand, and I think I would’ve been more motivated to stick with engineering school.

That being said, I’m glad I’m at a point in my life where it all now kinda makes sense why binary is a thing.

This whole video was a pleasant way to appreciate the ingenuity of people. It also fixed a core analogy of mine: it’s not that we tricked rocks into thinking, rather it’s that we tricked atoms into moving whichever direction we want.

The YouTube algorithm got me again with this video.

I’m sharing it here because I found it helpful to frame my situation as an experience worth experiencing, and nothing more. Not to judge it, not to try and shape it, but simply to be.

Seems lofty and pretentious, perhaps, but it’s helpful as I am trying to figure out what my next move is.

I should just let things be. I can’t control whether someone will pay me to build a thing for them. All I can do is put myself out there and see what the universe brings.

So far, the universe has delivered a ton of rekindled friendships and potential new gigs.

I think it is also insisting that I stop cramming so much into a day and start spending more time with myself.

Back in the go-go 80s and 90s, one of the most massive movers of the direct market was a 14-store juggernaut that sold millions of dollars in comics, was a broad-based hobby game store, and sold tens of millions of dollars in sports cards.

Then a new owner got busted on a variety of drug and weapons charges, and the chain went through a very public humiliation and twist in the wind until it finally, mercifully, died.

So why have you never heard of Shinder’s?

For the past few years, our immediate family has gone on a trip to Sheboygan. There’s a small collectible shop in town that gives me the same feelings of joy I got as a kid visiting the Schinder’s in Edina.

I never knew the national significance or sordid history that retail chain had!

I get why we fear dreaming. It’s hard for us to get our hopes up that things will go the way we want them to. Yet and still, we need to put this worry as far away from our psyches as possible. You might call it madness, but I call it necessary.

When we are afraid of having too much hope, we’re actually afraid of being disappointed. We are anxious about expecting the world to gift us and show us grace, because what if we end up on our asses?

So we dream small or not at all. Because if we expect nothing or expect something small, we cannot be disappointed when the big things don’t happen. We think it’s a great defense mechanism, but what it really is is a liability on our lives, because we are constantly bracing for impact.

I haven’t really felt like I’ve had a dream or vision for years now.

The last month with no job has really blessed me with an opportunity to start dreaming again.

And guess what? It’s actually kinda fun to do it, even if it comes with some occasional failure and disappointment.

Because for me, the feelings that come with complacency are significantly worse than the risks that come from dreaming.

(Side topic for future Tim to explore: how are dreams and anxiety correlated?)