“Hectic, but great”

I find it challenging to decide how to answer when people ask me how I’m doing. I try not to be superficial, so I give my answer some consideration. I want to strike the balance of respecting that a person may be just be making small talk, or they might be asking out of a desire to really connect. So I want to keep it brief, but open to further conversation. I often end up saying some variation of “hectic, but great”.

“Person juggling all the things” — generated by Stable Diffusion
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Expand Your Mind With One Weird Trick

In some ways, the story of my career is taking stretch opportunities that require me to jump into the deep end of unfamiliar territory. At this point, one of my key skills is knowing how to navigate situations where I have a lot of unknowns. I want to share a technique I have developed, which has been immensely powerful for me. Let’s call it mental model rewriting.

Roll Safe meme picture: a guy tapping his head, looking smug, as though he's got secret knowledge
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The AI Big Bang

Image generated from stable diffusion from the prompt: big bang happening in someone's brain

I generated this image with the prompt “big bang happening in someone’s brain” using Stable Diffusion

2022 has been an astounding year in AI. I don’t think anyone needs a recap (and I’m not the guy to provide one), so I’ll namedrop Stable Diffusion and GPT as examples of what I’m talking about.

While only the most jaded person could see what’s going on in AI and not be completely blown away, there is debate around exactly what the socioeconomic implications of this new phase of AI will be. On one hand, you have people already predicting that we’re in the end game for white collar workers, such as artists, writers, and software developers. Other folks, perhaps more attuned to the limitations of the AIs we’ve seen, are urging a much more sober outlook. I see massive change on the horizon, but along a different axis than some of the more simplistic predictions.

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11 Principles of Engineering Management

More than 2 years ago, I decided to try to create a brief, digestible manual on the expectations of management for senior engineers at my company who are considering making the shift. At the time, I had about 3 years of management experience, including two prior companies. Enough to feel like I knew how to do the job, but not enough to feel like I should be some kind of authority on management. After letting this marinate for a couple years, I’m ready to share what I have learned.

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Employee Equity: Understanding “qualifying disposition” is a must

If you have worked for a tech startup, you have probably earned incentive stock options (ISOs) as part of your compensation. ISOs are notoriously difficult to understand, let alone to strategize. In most cases, it frankly doesn’t matter, because most startups will not become spectacularly successful, and therefore, the options will never become a dominant part of the money you made during your stint. But, if you are lucky enough to hitch a ride on a unicorn 🦄, it can get very complicated, indeed.

The tax treatment of ISOs encourages employees to take financial risks, in return for potential tax advantages. If there were no tax advantages to be gained, it would be advantageous in all cases to exercise options as late as possible—either just before expiration or when you want to sell the stock—because you would have maximal certainty of the value of the shares. But because there are holding periods for tax advantages and triggers for taxable events, there is pressure to exercise earlier. This means locking up cash for years, before knowing when, or even if, the shares can be sold for profit.

The one thing you must understand about ISOs is the concept of a qualifying disposition. I’m going to first explain what that means, and then present a brief case study from my own situation.

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Ableism: the sneakiest “ism”

Fighting the prejudice within myself is a lifelong battle. One of the -isms I struggle most with is ableism. It comes through in my language, and as I’ll explain, I believe it underlies a stubborn prejudice in my heart. It is completely normalized to demean things and people as “stupid” or “crazy”. If you want to know why this is a bad thing, this article does a good job of explaining. Please read it, and do try to suspend the voice in your head that thinks it’s maybe being a bit excessive. Just for a minute.

All done? Great, because instead of stating the point they’ve made so well, I want to talk about why I accept it.

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Why does the world want index investors?

I have no financial training or credentials. This article represents my understanding from synthesizing many sources of information, but I am likely misusing terminology, and I may be factually incorrect on some points. Apply this information at your own risk.

Don’t invest in anything you don’t understand.

This is the first rule of investing. In a world where people want your money, it’s a good way to avoid becoming mark, swindled out of your life savings. In other words, it’s important to understand:

  • What your money will be used for
  • Where the new money to pay your return-on-investment will come from
  • What the risks are

If investing for building personal wealth has a second commandment, it is to continually pump excess income into low-cost index funds that track a large chunk of the US stock market. It’s not the purpose of this piece to justify this, but mountains of research indicates that this almost absurdly simple strategy—when executed with discipline and an iron stomach—has historically outperformed pretty much every complex investment strategy implemented by active traders, especially once fees are accounted for 1.

I have found these two pieces of advice to be in conflict. This piece is my attempt to sort this out.

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The kindest things anyone has ever done for me

Recently, I’ve gotten into a podcast called Invest Like The Best. The host ends every episode by asking his guest “what’s the kindest thing anyone’s ever done for you?” To be honest, this didn’t stick out to me until I heard a couple guests answer with some pretty trivial shit. I won’t say which guests, but imagine it’s something like “someone lent me $100 the other day”. And, I must admit, I felt pretty judgy. Like, how privileged must your life be to have something so trivial be the kindest thing anyone’s ever done for you?

To be fair, maybe they were just put on the spot and didn’t have time to think deeply about it. And really, I don’t really know their life, so whatever it was they actually said really made a difference.

Anyway, it got me thinking: what would I say? I’ve got two answers.

Trigger warning: severe depression is discussed.

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Screening developers should be easy

I’ve been thinking about programmer hiring for several years now, and I have a new theory for how to do it:

Make it clear what it is your software team does, and hire people who can make a compelling case for why they want to join your team.

That’s pretty much it. Class dismissed.

I guess I should justify this theory. The remainder of this piece describes my journey to this radical realization.

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