Betterment

We tested multiple AI tools for synthesizing discovery output and found the best insights come when machines find the patterns and humans connect the dots.

Verifying magic on the jagged frontier

There was a story in the WSJ (syndicated without paywall to MSN) about six friends. All Type-A. All trying to plan a more or less straight forward

The approach I've used to quickly assimilate the best advice in a domain (and actually use them to change my life)

In an oft-quoted speech, Winston Churchill said: Never give in–never, never, never, never, in nothing great or small, large or petty, never give in except to convictions of honour and good se…

Worth noting that there’s no ‘w’ in reckless. We imagine there might be, since a wreck is entirely possible. There’s the recklessness of creative generosity. This happens wh…

It’s easy to announce that we don’t have time for a new skill or a generous act. But the truth is we probably could find the time. What we don’t have is energy or motivation. Find…

A frog has no trouble grabbing a fast-moving fly in midair. But the same fly, sitting on a leaf, is safe, essentially invisible to the frog. We’re a lot like frogs sometimes. We choose to pay…

…might not be the same as making an impact. Making a point doesn’t take very long and it can be gratifying in the moment. Making an impact happens over time, and rarely brings the same …

If you’re going to build a conference, a newsletter, a podcast, an AI service or even a tennis tournament, please pause before you decide to be ad supported. (Ads are not the same as sponsors…

For Richard, a crazy idea was an opportunity to either prove it wrong or prove it right.

To understand the world today, we must see it as actors of the past did: through a foggy windshield, not a rearview mirror, facing a future of radical uncertainty.

The same technology promising to make us smarter is preventing the one thing our brains need to think.

Everyone is always doing their best. Given their situation, priorities, and awareness (the circumstances), people make choices. If we want to change how others respond, we need to change their circ…

What if we used AI to slow down, challenge our thinking, and build new tools, dashboards, and experiments?

Tags are dumb. They don't work and if you prefer them over folders, you're wrong. So I'm rewriting my blog with tags as the primary mechanism of organisation. I'm going to fix tags.

We like to think that we can do almost anything. Give me a broken piece of consumer electronics, and I’ll open it up and kick the capacitors. Give me an embedded Linux machine, and I’ll poke around…

Remember George Orwell’s 1949 dystopian novel, Nineteen Eighty-Four?  As fans will know, it centered around the Stalinist-style authoritarian regime of

Often, the things we want the most aren’t directly related to the things we need. In fact, they might be very similar to things we already have. Wants are fueled by stories, and stories come …

If you’re facilitating the daily coordination meeting (standup, daily scrum, whatever you want to call it), and you’re doing all the talking, then you’re doing it wrong.

Don’t play games you can’t win. If the deck is stacked against you, a smart option is to go to a different table and play with a different deck. The dominant system wants you to wait to…

Last month, a 22-year-old entrepreneur named Emil Barr published a Wall Street Journal op-ed boasting a provocative title:​ “‘Work-Life Balance’ Will Keep You Mediocre.”​ He ... Read more

It’s Labor day again. Beach trips, barbecues, the whole end of summer ritual.  It began as a celebration of the American worker in the 19th Century by the

Here’s a quick tactical riff about how we name things. It’s worth considering that: Sometimes there’s more than one thing we need to highlight And putting those things in a list i…

Education is distinct from learning. Organized education is a form of indoctrination and certification. Sometimes it leads to learning, but not always. You can win at education by figuring out what…

It is impossible to make a perpetual motion machine, you’ll waste your time if you try. It is possible to write a book of poetry that will sell 10 million copies. It is unlikely, it probably …

Large organizations are purpose-built to do what they do, under prevailing conditions. People are hired, assets are acquired, measurements are put in place–all to optimize what’s happen…

One sort of delusion is believing that we’re smart and skilled simply because we got lucky. This perpetuates a cycle of bad decisions that just happened to lead to good outcomes, and causes p…

When we fall behind, it’s tempting to hustle to catch up. When the competition heats up, it’s imperative we hustle to get ahead. Hustle is a particular kind of shortcut. Hustle is pushi…

I’m now entering the final month of my year-long Foundations project. This month’s focus is service. While the previous foundations have all focused on making one’s own life better, this one centers on contributing to the well-being of others. I thought service would be a good capstone for the project, a reminder that the point […]