Lifestyle Moneyball: 10 Questions for a Better Life

“People who run ball clubs, they think in terms of buying players. Your goal shouldn’t be to buy players, your goal should be to buy wins. And in order to buy wins, you need to buy runs.” — Peter Brand in Moneyball

April 2023 included two of the most rewarding, exciting experiences of my past year.

It began with a trip to El Salvador with my dad and my grandpa to their birth country.

My grandfather is one of the most interesting men I’ve ever met. He was the first Latin American diplomat ever to be knighted by the queen of England.

Yet, my story with him is complicated, since I didn’t feel like I got to know him until I learned Spanish. The story of “meeting” my own grandfather, I covered in this essay which my university, NYU, published back in 2021.

My father, while born in El Salvador, I had rarely seen the “Salvadoran” side of him, and yearned to explore his home country with him.

From there, I flew with my two best friends from college down to the US deep south. We started in Atlanta, then rented a car and drove to…

Birmingham, AL —> Montgomery, AL —> Jackson, MS —> Memphis, TN —> Little Rock, AK.

In the summer 2020, when political tensions ran high, we talked about the idea of traveling to the South and visiting important landmarks of the Civil Rights Movement.

Our journey took us from well-known sites, like the Selma bridge, where civil rights protestors began a 54-mile march from Selma to Montgomery, to lesser-known gems, like Rickwood Field in Birmingham, America’s oldest baseball park and former home of the Negro American League Birmingham Black Barons.

I’m still digesting the depth of each experience.

As I reflect on this month, the prevailing theme in my mind is how lucky I have to have set up my life to have experiences like this.

In Ozark National Forest, in the last stop on our Civil Rights tour, I sat in a hot tub at an Airbnb with my best friend and he said, “It’s so sick you have your life set up where you can do this on a Wednesday.”

“Yes,” I told my friend (who has also built quite the life, and whose first collection of poems got published by Atmosphere Press this summer), “I think a lot of people think the goal is to buy things, but my goal is to buy freedom, experiences, and peak-energy free time.”

My friend is the type of man to reply with a timely movie quote.

“In order to buy wins, you need to buy runs,” he said, laughing and imitating the movie. “No but in all seriousness,” he told me, “you’re playing Moneyball with real life.”

Moneyball tells the story of the 2002 Oakland Athletics, who, with a different approach to baseball, were able to compete with teams despite much fewer resources. The Oakland A’s had a payroll of less than 25% of what the New York Yankees had, yet both teams won 103 games that year.

Around the same time in the film, analytics whiz Peter Brand says, “Baseball thinking is medieval. They are asking all the wrong questions.” I think often this applies to life. The right questions in this phase in my life have led me to these types of experiences, and to be able to soak them in along the way.

Tim Ferriss in The 4-Hour Workweek called his vision of life, complete with “mini-retirements,” Lifestyle Design. I would say I’m playing my own version of Lifestyle Moneyball.

I’ve been able to avoid the wrong questions, and instead look a life a little bit like I look at baseball: an arena where, by asking the right questions, I’ve been able to create a great life.

Here are 10 fun questions I love to ask myself, often in the form of journal prompts, sometimes as quick check-ins, that have helped me wind up in so many magical, inspiring, gratitude-fueling situations over the last year.

I hope one or two of these strike you and inspire you to ask your own set of questions.

1) Do I Need More Mayhem In My Life?

I’m the kind of person who, if I didn’t push myself to spend time with friends or see new places, I would stay inside 350 days a year, and be at concerts the other 15.

Moving to New York when I was 20, I learned to break away from this, as the city taught me the magic possible on any given night.

This led me to start asking myself do I just need a little more mayhem in my life?

Ryan Holiday said, “Writers lead interesting lives.” I find this prompt leads me to uncover hidden magic around me and all over this planet, to go on unknown adventures.

2) Where Are Structure and Goals Keeping Me From Great Experiences?

I think goal-setting is one of the most overrated concepts in all of personal development. Being rigid in my goals, when I was young and ambitious, closed me off to so many opportunities.

Now, setting fewer goals keeps me on the look for the beauty of spontaneous human experience. I find myself accomplishing things I couldn’t have possibly predicted if I tried to set goals.

3) Can I Take Today Off?

Often, the answer is yes. My productivity is uncorrelated to how much time I spend working.

4) How Can I Get The Most Work Done in 2-4 Hours Today?

In 1955, author Cyril Northcote Parkinson coined the now-famous “Parkinson’s Law,” which is the idea that work expands to fill the time allotted for its completion.

Paradoxically, I’ve found I can get just as much, or more done by blocking off 2-4 hours to work. This is especially true if it’s in the morning (8am-12pm), when my attention and focus are typically highest.

5) Did I Take Enough Notes?

After all the mayhem, my brain is often spinning with ideas, connections, and conversations to reflect on. I know I won’t remember it all if I don’t write it down.

While I find my best writing requires distance, often the notes I took while I was in the throes of the experience have been invaluable.

6) What Can I Get Rid of?

If you read my last newsletter about How to Be “Rich” With Less, then you understand how much having less, and learning to be content with less, has spearheaded a new period of growth and happiness for me.

I find myself turning to this question more, as I continue down cultivating a path of desiring less.

7) How Can I Read More?

Although my life this month was hectic, I started and finished six books. Reading in conjunction with experience keeps me thinking and absorbing ideas, while being able to relate these to my experience.

Often, my reading corresponds to what I’m going through. For example, in Birmingham, I bought a book about Willie Mays and the 1948 Birmingham Black Borons of the Negro American League, just after seeing their home stadium, Rickwood Field.

With this question, I find myself pausing during the day, reading as soon as I wake up on a slow weekend (or weekday) morning, and spending 3-4 hour chunks in slow evenings reading.

8) Is One of My Favorite Bands Playing There? Can I Schedule My Trip Around That?

Last summer, I planned a week trip through Italy and Switzerland around two concerts, one in Bologna and one in Zurich, to see my favorite bands. These concert dates gave structure and purpose to a

When I’m looking for the next life experience, sometimes I’ll look at tour schedules for solutions.

(This month, I planned a business pit stop in Orange County, California around a pop punk show.)

9) Can I Take The Bus?

I’ve taken transit in the most unlikely of US Cities, from Orange County, to Austin, to Phoenix. I’ve come to view the public transit quality is a litmus test for the true soul of a city, as I see how hard it is to get around without the luxury (and it is a luxury) of a car. Many places, I’ve found it to be not so bad, and I’ve done what others deemed impossible: taking trains in LA.

Every bus, tram, or train ride is an experience to learn about a place, and often, a great time to read, making even long bus rides fly by in blissful stories.

10) Will Movement, Sunlight, Caffeine, a Nap, Meditation, or Journaling Solve This Problem?

80% of the time, the answer is yes. If I feel overwhelmed or tired, I just need one of these.

Send Me Yours.

What are some of your favorite questions or journal prompts lately? I’d love to hear.