365 Dead Drafts

Before iPhones, I used to wear my backpack wherever I biked in Boston because my brain would never stop, and I wanted to have everything necessary (laptop, notebook, and camera) to quickly capture these curiosities before their vividness because as foggy as a forgotten dream.

Not every idea was useful. Most ended up in the trash can. But many did serve as a substrate for something more. Maybe a poem. Maybe a hobby. Maybe some new creative endeavor.

Startups and Desert Island Employees

Kevin is a MacGyver-like technologist. During our five years of working together, he had this knack of pulling rabbits out of hats and coming up with solutions and workarounds that blocked others. When describing him, I would tell people that if someone were to drop him off on a deserted island, he'd find a way to build a server by the close of business that day. Now, of course, there was no real way for him to melt sandy beaches into silicon chips. Still, it was more a statement about the overall resourcefulness and tenacity by which he attacked problems.

Diamonds and Defects

What we choose to look for can significantly improve our moment to moment experience.

The ordinary person searches for and points out defects.

The effective person searches for and discovers the occasional diamond.

The extraordinary person is constantly seeing the diamonds in the defects.

Projecting "Out War"

Ducking Siri! If you get the joke, then you are probably used to the wonderful world of autocorrect fails, which can range from annoying to hysterically funny. Autocorrect fails can also offer little gems of insight for self-reflection. Take the title of this article as an example...

The Ignorant Side of History

Everyone knows the difference between right and wrong, right? Wrong. And this includes me. I have a certain level of paranoia that things I believe with 100% conviction will turn out to be utterly wrong in a decade. Only hindsight will confirm whether my sure bets were not delusional gambles. Until then, I try and live by the philosophy of Marc Andreessen of "strong opinions, weakly held." However, I'm human, and I have my blind spots. Maybe my belief systems have already been invalidated, yet I'm still unknowingly and unwittingly living on the wrong side of history.

Dying in Plain Sight

10,000 hours. This is the number made famous by Malcolm Gladwell in his book Outliers. The claim is that it's the (minimum) time necessary to achieve mastery in a subject matter. The bad news: it's not a guarantee. Without proper knowledge, strategy, and natural talent, it can be a lot of effort with minimal results.

Searching for My New Community

Leaving a tribe is painful.

No, I'm not speaking in hand-wavy metaphors. Literally, loneliness is a biological feedback loop to urge us back into a tribe. The reason being is that evolutionary wise, reliance on a tribe was a survival mechanism that we still benefit from this day. Only the most extreme introverts (and this is exceedingly rare) can truly live the lifestyle of a hermit apart from a family, a community, a tribe, or even strangers.

I know this pain. I've left or lost my tribe multiple times.

All Or None Thinking

A friend of mine recently asked if I had any experience with all-or-none-thinking. I wanted to respond, "Always! Never!" in my typical #dadjoke fashion. However, when "the stakes are high and the moment is brief" (to quote Joel Roberts), this subject matter warrants a serious, nuanced conversation.