The Creeping Goalpost

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.

Make it Easy

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.

Chocolate Malt

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.

Lean on Me

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.

The Economist Who Asked Me for Financial Advice

Sometimes it is all about the little things. One of my morning podcasts on the way to work (“Freakonomics Radio”) had a title that hooked me like chicken liver on a fishing line catches catfish. It read “Are Personal Finance Gurus Giving You Bad Advice?” However, what made me cheer was not the title.

The host, Steven Dubner, mentioned hiring a CFP as a means of finding decent financial advice! Apart from a brief commercial on Hulu once that brought me to my feet, this was the first time I had seen the term CFP in mainstream media. In my strange little world, it made me cheer in my car with a little unbridled glee, not unlike the typical Washingtonian might cheer when they realized the Mariners were finally making the playoffs again. My apologies to the woman in the minivan who probably thought I was shaking my fist and yelling at her.


The dollar you have right now has more time than any dollar you will ever have. Put another way, that dollar is the most powerful dollar you will own for the rest of your life. Like Spiderman’s uncle would say, that dollar arguably has the most responsibility too. Yet, especially with people who are young, you hear things like “I have the rest of my life to make money.” 8.2 million people in the US as of 2021 with severe enough disabilities to receive government assistance might disagree with that statement. But for most, it is technically true.

That said, people can become wealthy by casting aside the idea of having the rest of their life to invest. If they simply start to invest, incredible things can happen. And it does not have to be mutual funds, stocks, real estate, or even a bank account. Investing can mean investing in oneself. Committing to a degree, a new skill, the extra time to get a promotion, exercising, developing better relationships, starting a new business…they are all forms of investment.


The Cliff You Don’t Actually Care About

When we need the answer to a question, the first stop today is the internet. We ask and our search engine of choice opens us to a world full of people ready to help. The problem: the help is contradictory. For example, a client asked this recently:

“Can I take money out of my 401(k) penalty-free?”

As a financial planner, it made me smile. I have seen dozens of answers to this question over the years. The answers could almost be organized from worst to best on a sliding scale. Here are a few of them:

The To-Do List that Will Save Your Life

I was sitting in a beautiful theater watching a broadway production of Frozen. A woman with the voice of an angel-meets-songbird plays Anna, a young princess ecstatically looking forward to the day she can be free to start the rest of her life after years of drudgery and loneliness:

“It'll be totally strange
But wow, am I so ready for this change!

'Cause for the first time in forever
There'll be music, there'll be light
For the first time in forever
I'll be dancing through the night”

Most people would think of romance. 


“Give me a lever long enough and a fulcrum on which to place it, and I will move the world.” –Archimedes

On my sixteenth birthday, my grandmother kindly gifted me her old Saturn. As a teenager who worked for gas money and drove most Saturdays around the state to compete in wrestling tournaments, gas was a prized commodity. I would squeak over hills without hitting the gas pedal, go exactly the speed limit (except when I rocketed downhill), drive with the windows rolled up, keep almost nothing in the car, and generally try to optimize how far my tank would take me.

Today, it seems a little overkill. 


Ostriches don’t actually bury their heads in the sand. They lay their eggs underground, and will occasionally rearrange the eggs with their beak to regulate the temperature of the eggs. The idea that an ostrich buries its head in the sand to hide or ignore its surroundings is actually a common misnomer, and a good thing for the ostrich and the survival of the species.

The same cannot be said of the common investor.