The Saver's Paradox

Early in our marriage, my wife Brooke came home from work in an uproar. She was just embarking on her journey as a teacher and submitting all the paperwork that comes with a new career. Among this paperwork were Brooke’s retirement benefits, where she was supposed to decide how much to save for retirement. Having financial advisors for a father and a husband, she was determined to aggressively save. She filled everything out, in her classic perfect penmanship, and proudly walked into an HR meeting where someone would review her paperwork.

She did not anticipate a struggle. The well-intentioned HR employee walked through Brooke’s paperwork, pausing at her retirement benefits.

“You are saving too much,” she said. “You should consider saving less.”

Have Your Dollar and Eat it Too

As a 7-year-old, I remember my parents decided it was time for a change. Determined to lose weight and improve their health, they latched onto Body for Life, a nutrition and exercise program. It was fun to watch the old videos of people following the program, changing their bodies, and becoming better versions of themselves. The books and videos featured people young and old, with before and after pictures and essays that were frankly inspiring. Of course, the program touted their own proprietary supplements to monetize the motivation, but the basic tenets of the program were fairly reasonable. My parents embarked on their fitness journey, and my dad went on to win a prize from one of their competitions--a trip to Cancun with my mom.

Watching my parents get up early to go to the gym before work and eating healthy, it made me want to do the same thing. My dad would humor me: he would make a little extra of his healthy breakfast and leave it for me in the morning, and he gave me a light dumbbell to do exercises when I insisted on lifting weights. Little did they know the monster they would create; 


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.