I'm a sucker for profiles on people like Conan O'Brien. The way his mind works is endlessly fascinating to me.

What intrigued me about this particular New York Times piece is his observations on agony:

Many comedians see a connection between misery and their ability to be funny, often citing humor as a survival mechanism. But after considerable therapy and reflection, O’Brien has changed his mind. He’s come to believe that not only are they not related at all, but so much stress didn’t help him be funnier. With new eyes, he has set about creating a new story. “Looking back now, I think some of my best ideas came from just goofing around,” he told me.

He points to possibly his most celebrated writing credit: the monorail episode of “The Simpsons,” which many television critics agree is the greatest in the history of the show. He describes its origins in an Olympic Boulevard billboard for a monorail, leading him to write on a legal pad: “Springfield gets a monorail. Homer likes the idea. Marge not so sure. First act: ‘Music Man.’ Second: Irwin Allen parody.”

He brought this pitch to the “Simpsons” office, writers liked it and started adding jokes. “It was like falling off a log,” he said. No agonizing at all.

I have a ton of quotes on the main page of this site¹, and one of them is from Eckhart Tolle: "Suffering is necessary until you realize it is unnecessary."

The more I agonize over my own life choices and what's next for me, the more I realize that I just need to let go. It's a constant push/pull; you have to be both unabashedly dogged in your pursuit of what you want, but you also need to be chill about it.

In my opinion, security is one of the most forgotten aspects of software engineering. It rarely gets focused on until it’s too late. Even though at least one incident lands on HackerNews every week where some data gets leaked or someone gets hacked — people still think, “Nobody cares about my little startup.” You might think you're too small to be noticed by the big, evil hackers. Wrong. Size doesn't matter. You're always a target; there’s always data to leak and ways to exploit your business.

This is a great primer for the security-related items you need to consider when you’re building software.

Some takeaways:

First, any human-built product is going to be insecure. Nothing is 100% secure, ever. The best you can do is make the bad guys earn it by making it difficult to break into.

Second, your biggest vulnerabilities are almost always human. You can build Fort Knox, but if I’m able to trick your guard into opening the door for me, then what’s the point?

Third, I’m grateful for frameworks like Ruby on Rails which handle a good chunk of the author’s “step 0” items out of the box. Picking the right tool (and keeping that tool sharpened) is the best first step.

Fourth, there’s never a moment with software when you can dust your hands and say, “ope, we’re done!”

Security is especially an area in which you can’t sit still. If you build an app and let it sit for a decade without any updates, I can almost guarantee you that there’ll be a vulnerability in one of your dependencies which I could exploit to take over your system.

Finally, if you reach a certain size of organization, you need someone thinking about this stuff full time and orchestrating all the pieces needed to keep a secure system.

[Techno-selectionism] is a perspective that accepts the idea that innovations can significantly improve our lives but also holds that we can build new things without having to accept every popular invention as inevitable. Techno-selectionists believe that we should continue to encourage and reward people who experiment with what comes next. But they also know that some experiments end up causing more bad than good. Techno-selectionists can be enthusiastic about artificial intelligence, say, while also taking a strong stance on settings where we should block its use. They can marvel at the benefits of the social Internet without surrendering their kids’ mental lives to TikTok.

As much as I personally enjoy hanging out on the cutting edge and experimenting with new technologies, I would consider myself a techno-selectionist when it comes to adopting these tools into our lives.

I am sure some people enjoy the new Google search results that are driven by AI, but when it still recommends you add glue to pizza despite the widespread mockery they received initially, maybe we should take a step back and demand better from our techno overlords.

Or, since we know that’ll never happen, maybe we need to decide for ourselves which tools are worth incorporating into our lives.

Consider the fact that most companies are unable to successfully develop and deploy the simplest of CRUD applications on time and under budget. This is a solved problem - with smart people who can collaborate and provide reasonable requirements, a competent team will knock this out of the park every single time, admittedly with some amount of frustration. The clients I work with now are all like this - even if they are totally non-technical, we have a mutual respect for the other party's intelligence, and then we do this crazy thing where we solve problems together. I may not know anything about the nuance of building analytics systems for drug rehabilitation research, but through the power of talking to each other like adults, we somehow solve problems.

But most companies can't do this, because they are operationally and culturally crippled. The median stay for an engineer will be something between one to two years, so the organization suffers from institutional retrograde amnesia. Every so often, some dickhead says something like "Maybe we should revoke the engineering team's remote work privile - whoa, wait, why did all the best engineers leave?". Whenever there is a ransomware attack, it is revealed with clockwork precision that no one has tested the backups for six months and half the legacy systems cannot be resuscitated - something that I have personally seen twice in four fucking years. Do you know how insane that is?

This whole article is a must read.

The main point: with any major leap in technology, there will be hucksters who purport to use the new hotness to solve all your problems.

The problem is that most organizations don't even take the time to solve the already solvable problems that exist within that organization.

New Javascript frameworks, database software, on-prem versus cloud-based server architecture, containerized systems, blockchain, mobile apps... unless you know how using these tools will solve a problem that your existing tech stack cannot solve, they're nothing more than distractions.

You don't need a garage full of tools to get a job done. Getting the fundamentals right is so much more important than making another trip down to Home Depot to buy your sixth version of a hammer.

Bob Marley (supposedly) said that “some people are so poor, all they have is money.” What he meant was that there are people that mistake the pursuit of wealth for their purpose, and when they realize that they’ve conflated the two, they understand that they’ve missed the point of why life is so worthwhile in the first place.

This is why purpose must be discovered without the promise of incentives or monetary rewards. It can only come from conducting an honest audit of what makes you feel wonderment (i.e. childlike curiosity) or a sense of duty (i.e. parental responsibility), and then directing your attention to making the most of those endeavors.

The sense of self-worth that can be derived from purpose is free from money’s clutches, so keep this in mind whenever you feel discouraged by how much you have. Money is simply not a variable here, and the knowledge of that goes a long way.

I’ve spent the past six months of unemployment conducting the audit described above.

And I’ve learned that what brings me wonderment is learning how technology works¹, and my sense of duty is in teaching others how to use it.²

It’s not so much that I forgot those things about myself. What brings me such shame is the fact that I’ve suppressed the urge to pursue those activities in the name of making money.

Ultimately, love is the thing that matters most, but it’s often overlooked and disregarded as a cheesy emotion. In the minds of many, skepticism signals intelligence, whereas love signals naivete. After all, you garner respect by sounding the alarm on humanity’s problems, and not by pointing to love as the answer to them.

This is precisely why love is taken for granted. Even if love is felt between you and another person (be it a friend, partner, family member, whomever), it’s often left unarticulated because saying “I love you” means that you’re fine with seeming naive and aloof. And if this fear goes on long enough, you’ll feel that the best way to express your love will be through ways that act as surrogates for it.

Another thing I’ve learned about myself is that I am a naturally trusting person.

The majority of people I’ve encountered professionally appear to be the opposite. In particular, those playing the entrepreneur game seem especially skeptical or fearful of leaning into love.

Skepticism and fear drive those folks to make decisions about their business which ultimately lead to their demise.

I’ve sat in countless meetings with teams of executives who are frantically trying to come up with an idea for how to get more people to buy their thing.

At some point, an obvious answer emerges which involves building something that genuinely helps people.

But that obvious answer is almost universally looked at the same way you’d look at a plate of boogers because of financial concerns.

This general feeling is why I’ve struggled so hard to find a job. I’m tired of building software which only serves the purpose of making money.

Instead of jumping into another job where the culture is driven by money, I’m waiting until I come across a culture that is driven by love.³

Money’s a great tool, granting me a level of freedom that I may not have experienced had I pursued any other career.

But money is also the primary reason why I am dealing with severe anxiety and depression. It’s why my heart constantly feels like someone is squeezing it like a strongman squeezing an orange.

The only thing that causes the grip to be released? Doing things that lift the “purpose” and “love” levers. It’s when I trust others and spread as much love as possible when I feel the most alive.

Using the analogy in this article, I’ve spent the last 12 years of my life optimizing for the money-receptive levers. I’m gonna spend the next few in pursuit of lifting the money-negligent ones instead and see where that leads me.

Because of my experience with Remini — and despite my natural and deep-seated antipathy toward tech solutionism of all sorts — it’s impossible for me to dismiss or decry grief tech out of hand. At present, at least half a dozen high-profile start-ups claim they can train interactive chatbots or video avatars to mimic the personalities of the dead; tech-savvy mourners have also turned several general AI apps, such as Remini and Paradot, to grief tech applications. 

These services — marketed under names like Project December, You Only Virtual, HereAfter AI and Seance AI — raise pressing, significant questions around issues like privacy, predatory marketing and consent. What happens if grandma doesn’t want to “live” forever? Or her platform ups the cost of a premium subscription? Other commentators and ethicists — including, just last week, the prominent sociologist Sherry Turkle — have voiced concerns that grief tech blurs the boundary between the living and the dead and locks the bereaved in a sort of limbo. Such critics assume that the bereaved cannot spot the illusion of AI chatbots for themselves, and, moreover, that the bereaved should not indulge themselves in any comforting fantasies about death.

But people take comfort in all sorts of stories; I no longer feel wise enough to judge them for that.

First off, huge respect to Caitlin Dewey for sharing this story. It takes guts to be vulnerable and share something this intimate.

Second, consider me privileged, because I would have never considered miscarriage grief as a use case for artificial intelligence.

People grieve in all sorts of ways. It’s not up to me (or you, or anybody) to judge, but it is up to us to show up for each other and be helpful.

I know how important journaling is to my mental health. There’s something cathartic about forcing yourself to stare directly at your thoughts, putting words to the vague feelings that gnaw at you incessantly.

I can only imagine how cathartic it may feel to someone to see a rendering of what could have been. To give yourself some closure on the possibilities you dreamed for yourself and your future family.

Again, I’m not here to judge or endorse. I find myself once again just impressed at how people are able to figure out how to take technology and use it to deal with their problems.

In the context of nutrition, we’re comfortable deciding to largely avoid ultra-processed food for health reasons. In making this choice, we do not worry about being labelled “anti-food,” or accused of a quixotic attempt to reject “inevitable progress” in food technology.

On the contrary, we can see ultra-processed good as its own thing — a bid for food companies to increase market share and profitability. We recognize it might be hard to avoid these products, as they’re easy and taste so good, but we’ll likely receive nothing but encouragement in our attempts to clean up our diets.

This is how we should think about the ultra-processed content delivered so relentlessly through our screens. To bypass these media for less processed alternatives should no longer be seen as bold, or radical, or somehow reactionary. It’s just a move toward a self-evidently more healthy relationship with information.

This mindset shift might seem subtle but I’m convinced that it’s a critical first step toward sustainably changing our interactions with digital distraction. Outraged tweets, aspirational Instagram posts, and aggressively arresting TikToks need not be seen as some unavoidable component of the twenty-first century media landscape to which we must all, with an exasperated sigh, adapt.

They’re instead digital Oreos; delicious, but something we should have no problem pushing aside while saying, “I don’t consume that junk.”

Brilliant analogy from Cal Newport.

I was recently part of a big parenting discussion group about whether a parent should allow her tween to have a smartphone with Snapchat. It produced a lot of stories and anecdotes and feelings and opinions, including a few tales of teens finding ways to circumventing parental controls or even picking up burner phones in order to be able to do things like keep up streaks. There were also some anecdotes of real-life consequences around location tracking, hazing, content getting shared and saved without consent, etc.

It was eye-opening and terrifying, because my kids are too young for this sort of thing today, but I’m sure the options will be even more overwhelming and difficult to manage by the time they’re this age. The social pressures in their and your peer group will influence what’s considered appropriate, regardless of any age listed for any terms of service, and there are so many things that are technically permitted but not exactly good for us in this world.

I wanted to take the time to formulate the long reply I had composed into a more publicly shareable blog post – which will likely come back to bite me in the ass! I’m sure things will shift between now and when my eldest hits iPhone age, but for now, my perspective on giving a 13yo a smartphone with Snapchat is a hard NO, and this is my reasoning why.

My daughter is already asking me for a phone for her eighth (!) birthday, and right now, it’s an easy no.

I understand that social media is obviously where all your friends are and you don’t wanna feel left out, but to me, there is no difference between using social media and using drugs or alcohol.

The thing I keep telling my kids with stuff like this (swearing, adult themes, etc.) is that it’s all about context.

There will come a time when you are able to fully understand the context of when to deploy an F-bomb.

There will come a time when I can’t shelter you from the maelstrom of crap that rains down on you from every direction on social media. I hope if you choose to engage with social media, you do so with the knowledge of both the benefits of these platforms (connectedness, sharing your life) and, more importantly, the detriments (data privacy, mental health struggles).

But yeah, for now: no phones. Sorry, gang. My number one job as a parent is to keep you safe, even if you aren’t happy with me.

Once you do things quietly you become selfish in the best way – using money to improve your life more than you try to influence other people’s perception of your life. I’d rather wake up and be able to do anything I want, with whom I want, for as long as I want, than I would try to impress you with a nice car.

It always seems to come back to your vision, no?

As soon as you have a vision, you can set your own scoreboards, play whatever game you want with whoever you want.

I am still working on improving my horrible relationship to money, but I’m glad I have a partner who constantly reminds me that it’s important to not put your entire life on hold because you’re stressed out about finances.

From what I’ve experienced so far in life, there’s never a point at which you dust your hands and say, “welp, I did it. I won the money game, and I’ll never need to stress about money ever again.”

So as long as you’re being smart with squirreling away money when you can, you should feel empowered to buy things that make your life better.¹

Fathers have a direct, positive impact on the social, emotional, and cognitive development of their children, and this shows up in measures of educational achievement, social skills, and long-term mental health. While fathers do more paid work, and perform less childcare overall than mothers, they play a unique and complementary role in child raising.

While they play an essential role at all stages of a child’s life from infancy to adulthood, their presence seems especially influential as they grow older. A father’s closeness to his child in middle childhood and adolescence protects against loneliness and depressive symptoms, particularly in girls. Sixteen-year-old girls who are close to their fathers have better mental health at 33. Controlling for many other factors, the adolescent delinquency rate for boys is lower when they have involved fathers.

First off, a happy belated Father’s Day to my fellow dads, cool uncles, and other father figure-types out there. It isn’t just biological dads who need the shout outs; if there’s a kid in your life that you care about, then you should get your flowers as well.

Second, ever since we had our first child, I have looked forward to the current stage that both of my children are at.

I’ve never been one to see a baby and melt into a ball of baby talk and snuggles.

But I sure am down for teaching my kids how to apply the ultimate chinlock, ride a bike, catch a ball, step outside of their comfort zone, and cope with tough feelings.

I’m just glad that I found some empirical evidence to validate my unsubstantiated thoughts around fatherhood.