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These days AI is constantly on the tips of our fingers, our lips, and our minds. The era of artificial intelligence has arrived in a crash, rather than a gradual descent. Six months ago I decided to take it out for a test drive–I asked ChatGPT a few questions, curious to see if I was in danger of losing my job any time soon.

It actually surprised me.

After a warm up round of good ideas for Mother’s Day (which it passed with flying colors), I started asking it about work. ChatGPT avoids giving investment advice like the plague–no surprises there. But then I asked a question about estate planning. It gave a beautiful response. Thorough, simple language, and even a small example thrown in to illustrate the point along with a reference to the law specific to Washington state.

My dad had a brief stint as a land surveyor. Even a decade later, he was still able to eyeball distances and pace out yardage with, at least to a young child, surprising accuracy. Later when I was in high school, I can also remember him pacing something out and my mother interrupting him: “Why aren’t you using a tape measure?” Strangely enough, the tape measure told a fairly different story than my dad’s pacing. In hindsight, he probably just didn’t want the trouble of digging the tape measure out of his toolbox.

Sometimes I think people take a similar approach to measuring investment performance. We look for the quick, simple answer to “How are we doing?” At first glance, measuring performance of investments is crystal clear. “How much has my account gone up?” And to be fair, that is usually what matters most to investors.

But if you are trying to truly measure performance–how you, your investments, and your advisor are actually doing–it is worthwhile to, as Rafiki tells Simba in Lion King, look harder. Otherwise, you can wind up with a skewed or incomplete understanding of how investments are doing.

I was walking back to my car last week in the early afternoon. It was gloriously warm–a little heat wave to warm Washington state’s spring bones. As I walked, the familiar smell of sun-seared asphalt hit my nostrils. The smell instantly time-warped me back twenty years, to the summer days of riding my bike as a kid. Sometimes we forget how powerful our sense of smell can be, until the right scent pulls us back to memories we thought were long forgotten.

Oddly enough, those twenty-year memories didn’t seem like very long ago. On a similar note, my wife and I were talking about the year 2000–it doesn’t seem like nearly a quarter century has passed since that time.

My older friends and clients reading this will laugh. Just wait until you are 60, they chuckle. It only goes faster from here.

Beautiful truths emerge at the crossroads of unlikely encounters. This truth is no exception: it emerges between a Grandmaster of an ancient board game, a computer program, and a legendary record producer.

Rick Rubin is that record producer–for those unfamiliar, he produced records for everyone from the Beastie Boys to Johnny Cash to Metallica to Red Hot Chili Peppers. He has literally shaped generations of music. Rick recently wrote a book, “The Creative Act: A Way of Being”, where he recalls watching something miraculous unfold on live television.

Lee Se-Dol, a world-renowned Go player, was playing Google’s famous AlphaGo computer in a game that became a battle between humanity and technology. In a surprise twist, AlphaGo beat Lee Se-Dol. The game of Go was thought to be impossible for a computer to win due to its complexity, with more possible configurations for pieces than atoms in the observable universe.

So often in my line of work, people are searching for how they can fix their finances. Usually, people fall into one of two camps. One knows they have at least one problem they need help solving. The other camp doesn’t have a problem they know of–but they recognize they don’t know what they don’t know.

I am going to focus on camp number two.

This particular crew has a sinking feeling that they could do better. They are convinced that there are special strategies they can learn about to grow and preserve wealth more effectively.

So they seek me out. Like guests at the masquerade ball, they are a classic case of FOMO hidden behind a thin facade of financial responsibility. To be fair, their gut feeling is usually right. There is almost always a way to improve returns, reduce taxes, simplify things, or reduce risk.

I don’t watch TV. However, there is an old Nike commercial I love; many of you might be familiar with it. It is titled “Rise and Shine”. It channels that grind-it-out, be-different, not-easy-but-it’s-worth-it mentality, and it maintains a special place in my heart, smack dab between the Rocky theme song and the National Anthem. Play even the first five seconds and those first couple notes drag me back to sweat-drenched wrestling workouts and memories of chasing after a national title in college.

As many of you know, I coach wrestling. Sometimes the methods are a little unorthodox. An example: in wrestling, the best way to win is to pin your opponent. When we have three kids pin their opponent in a row, you might hear me and the kids yelling “Keel!”

Opposing teams are often bewildered. There is no “Keel” in wrestling lingo. It doesn’t mean anything in the wrestling world, isn’t short for anything, and is not somebody’s name.

It is something our team randomly invented. Teams don’t know it, but our kids chase after Keels. There is nothing special about three pins or getting pins in a row. Other than scoring points for your team, we do it for fun. It gives the kids something to strive towards: something achievable, exciting, and measurable.

Goals in financial planning really aren’t so different.

Two entirely separate situations share a common thread.

My daughter Belle was diagnosed with cerebral palsy a few months ago. For those unfamiliar with the condition, it is the most common motor disability in children. Many children with CP struggle to walk or control their muscles, and it is a lifelong condition. As parents, Brooke and I had countless questions at first about what it was, what we should do, and how we could help Belle as much as possible. We still have unanswered questions.

Soon after the diagnosis, Brooke found a group of parents on Facebook navigating the same thing. They understood exactly the kinds of emotions, questions, and challenges we are facing. Brooke had coffee with an incredibly strong, kind woman from this group who had lived and breathed a decade of caring for not one, but two children with cerebral palsy. Two hours later, Brooke came back full of perspective, tips, and perhaps most important, hope. She left with a better sense of direction.