A Tale of Two Trajectories

A couple walks into my office. The husband is a large business owner, and the wife is a doctor.

This sounds like the beginning of a financial planner-style bar joke.

They are in their late forties and want to retire at age fifty. We launch into their plans and financial situation. They have four million dollars in various investment accounts, income from the business, a large vacation home, and all the trappings of a high-income lifestyle. They love fine dining, cruises, and international travel.

A second couple walks into my office the same week. The wife is an elementary school teacher, and the husband is a cook. They are in their mid-sixties, want to retire next year, and lead a modest lifestyle. They have 350,000 dollars in the state retirement system, a small pension, a two-bedroom condo, and enjoy gardening and hiking.

Giving Money to the Kids

Many readers know Brooke and I are expecting. The idea of a little one’s arrival is thrilling, joyous, and still a little difficult to process. Of course, we want the best for our child in all the ways one might expect. We continually ask each other, how can we create an environment where children can grow into kind, resilient, empowered people? So often I hear people say they simply want their children to be happy. While I too wish happiness on my children, I have always felt that happiness is a byproduct of other things.

The Sting

Have you ever had something taken from you? It tends to hurt more than not having the item in the first place. The sense of “mine” is powerful, and that feeling of ownership sets in quickly. It makes for a particularly painful experience when we lose what we have.

In the world of finance, you hear this expressed in the form of little rules of thumb or idioms.

-“I haven’t lost money until I sell.”

-“The stock was up before—it will get there again.”

The Quiet Losers

I had just driven home from the office. As I stepped out of the car, my neighbor happened to be outside and said hello. 

“Hey, you work with investments and finance, right?” he inquired.

I do.

“Have you heard all this business about Gamestop?”

Yes, I have. 

“Man, I’ve been watching Youtube videos about it all day. Spot prices and call options and technical analysis and...!”

As I politely listened to his foray down the rabbit holes of the financial world, my wife could see me through the window. Her face said that my ear was being bent, but I did not mind.

"I don't want to mess this up."

“What if…” showcases the power of two words. They grant us a glimpse through a window overlooking the realm of possibility. We all ask ourselves and others this at some point. It is an expression of adventure, freedom of imagination, and the human spirit. Perhaps the most popular endings to that question center around wealth.

“What if I had a million dollars? What if I won the lottery? What if I was a billionaire?”

The scale might vary, but the underlying question is the same. What if I was suddenly wealthy? 

Easy Yes, Hard No

I like to think I am a nice guy. Typically, it works well: when you collaborate with others to help them achieve what they want for a living, being nice fits nicely.

Sometimes, however, you do someone a disservice by being too nice. The yes-man finds himself agreeably approving self-inflicted problems to those he serves. As an advisor first starting to give advice, it was difficult to disagree with someone. My family reading this will be shocked--I grew up loving to disagree and would argue from every point of view but the one offered to me.

Sometimes, the best thing you can do is hold someone accountable. Kicking the can down the road may be easier, but it does no one any favors in the long run. One might say we are in the business of the long run.

My favorite questions I like to ask potential new clients center around what is important to them and their families. 

The Green Shirts and Uncle Albert

I was reading about a researcher named Michael Tomasello, who has long studied what makes us human. A study he conducted compared 2- or 3-year-old children to chimps. When two children were faced with a task that yielded more toys for one than the other, the 'lucky' children in the study would, unbidden, share the extra toys with the other children. Chimps, by comparison, would not: they would keep the extra spoils for themselves.


I remember one of my first experiences working with a new client--what he said will likely tint the lens I see the world through forever. 

We both recognized there was a lot to accomplish. In my mind, it was going to be expensive to take care of it all. As one of my first experiences with a high net worth client, I was a little intimidated about telling him the cost. Advanced planning and money management takes time.  

Let me be candid; I was not a little intimidated--I was about to sweat through my clothes from being so nervous. He was an intelligent man, and understood investing quite well. There was a chance he would decide to try to do it himself. 

I Can Be Trained

I still have much to learn as a husband. Brooke and I celebrated 3 years happily married last week, and during that three years she has dutifully trained me in the fine art of being a spouse. She had a great deal of work ahead of her, but I admit she is patient. Looking back, one of the techniques she impressed upon me early on was the delicate nature of giving tactful advice.

Begin Again

I sat there, doing my best to recognize that even if just for a moment, everything was right. There was nowhere else to be, nothing to be done, and no thought or planning that had to occupy my brain.

Just the breath.

At least, according to Sam Harris, the creator of the aptly named meditation app “Waking Up.”