This week someone asked me to be on their podcast. It would be the first time someone interviewed me, so I started to think about what they might ask.

I brainstormed 22 questions that are commonly asked to podcast guests and thought about my answers to them. But instead of just thinking about the answers, I decided to write them up for myself.

This turned out to be a reflective and almost therapeutic exercise. I had never sat down and synthesized these questions for myself, but it turns out I had plenty to say for each of them.

If you've never written up your thoughts and responses to these questions, I highly recommend it. It will give you some insights into yourself and your views of the world that you have likely never put into words. Plus, it's kind of fun.

Questions

The 22 questions I came up with were:

Where are you from?
Where did you go to school?
What do you do?
What are you interested in?
What are you learning?
What are you focused on?
What are you currently struggling with?
What is your most audacious goal?
What does the first hour of your day look like?
What does the last hour of your day look like?
What book has impacted you the most?
What is your favorite book on health?
What is your favorite biography/memoir?
What is your favorite book on philosophy?
What does your content diet look like?
Which historical figure have you learned the most from?
Which current figure have you learned the most from?
What piece of advice would you give to yourself ten, five, two years ago?
If you could put one thing on a billboard, what would it be?
What have you changed your mind on recently?
What is one habit you've implemented in the last year that's improved your life?

1. Where are you from?

I was born and raised in Tampa, Florida, home of the most mediocre sports franchises in history. I went to school in New Jersey and currently live in New York City.

2. Where did you go to school?

I went to school and played football at Princeton, graduating with a degree in Operations Research and Financial Engineering. My major is a mouthful, so I usually just say Applied Math. On the football field I played Center, which, luckily, surprises people given I look less like an offensive lineman than I used to.

3. What do you do?

I work full-time as a global macro portfolio manager at an asset management firm. When asked what that entails, I say my job is to predict the global economy and react accordingly. In my free time, I enjoy exploring random topics that interest me, sharing them in my weekly newsletter Dickie's Digest, on this website as essays, or on my Twitter.

4. What are you interested in?

My specific interests change often (probably too often) but broadly fall into one of seven categories: financial markets, business strategy, productivity, philosophy, decision-making, longevity/health, and sports.

5. What are you learning?

I spend the majority of my time trying to better understand global financial markets. But you can only stare at charts for so many hours before the law of diminishing returns sets in. So I'm also learning some evergreen skills, skills that can be applied in any domain. These include online marketing, design, writing, and time-management. In the last few months I've dug into habit formation, stoic philosophy, and the carnivore diet.

6. What are you focused on?

My biggest focus right now is better leveraging my time and optimizing my energy levels. I've come to the conclusion that success is a relatively straight-forward process. Time is a fixed resource, equal for every person. Therefore the most successful individuals leverage their time more effectively. High-leverage activities are more difficult than low-leverage activities, and thus require more energy. So I’m focused on creating a flywheel of high energy levels leading higher leverage activities leading to high energy levels and on and on and on.

To better leverage my time, I am focused on taking things I am already spending time on but squeezing more value out of them. This means sharing the information with others (like this post!) and exposing myself to more opportunities. This idea lead me to starting this website, Dickie's Digest, and an weekly macro markets newsletter that I send around to my colleagues.

To better optimize my energy levels, I am constantly experimenting with different diet, exercise, sleep, and mental habits. You can only change these incrementally, but I find the process of continuous improvement in these areas very fulfilling.

7. What are you currently struggling with?

My biggest struggle is finding an optimal time-management system. I have nailed down the processes of organizing information and understanding exactly the things I should be working on, but I’m struggling to execute consistently.

My process for keeping tabs on the different project I’m working on is robust — I know at any given time what the next step is for a given project. But deciding which project to work on and focusing intensely on just that project has proven difficult. I need to be able to tune out all of the other ideas that pop into my head and focus on one task at a time.

To do this, I’m experimenting with time-blocking my calendar. The idea being each chunk of time, be it thirty minutes, an hour, or more, is assigned a single project. The goal is to execute solely on that project during that period of time. It’s going alright so far, but definitely could be tweaked a bit.

8. What is your most audacious goal?

I want to bring an NBA franchise to the city of Tampa, named the Tampa Bay Wave.

9. What does the first hour of your day look like?

For the last 500 days, my days have started almost the exact same. I wake up, brush my teeth, meditate for 10 minutes, log my weight, sleep, alertness, write one thing I'm grateful for, journal 250+ words of morning pages, then exercise.

This 60 to 90 minute routine is the foundation for everything else I do. The best part by far is having journal entries one year and two years ago for each day I write. Being able to review what I was thinking about on this day each of the last two years is thrilling to me.

10. What does the last hour of your day look like?

The last hour of my day is more inconsistent than my first hour. I have much less control over my evenings than my mornings, so I allow myself some leeway here.

In an ideal world, I shut off my screens an hour before bed, write down the best and worst parts of my day, plan my to-do list for the next day, and then read fiction or biography for 45 minutes.

11. What book has impacted you the most?

The best part about books is your world view changes forever after reading the best ones. For me, it was Awareness by Anthony De Mello. It’s hard to explain the book, but it’s one you just have to experience. It’s the book I’ve recommended the most to anyone looking to better understand themselves and their emotional state.

12. What is your favorite book on longevity and health?

The book that most positively influenced my energy levels was Atomic Habits by James Clear. Forming habits is a a crucial meta-skill for building anything, because building anything requires consistency. It's the book I most recommend to anyone looking to improve.

13. What is your favorite biography/memoir?

I’ve been reading more and more biographies and memoirs lately. I prefer memoirs or autobiographies to regular biographies, as I believe the personal flair of the subject writing about themselves helps us better empathize with them.

The two I’ve enjoyed the most are completely different but both uniquely their own. They are The Ride of a Lifetime is a memoir from Disney CEO Bob Iger and What I Talk About When I Talk About Running by Haruki Murakami.

14. What's your favorite book on philosophy?

The three classic books on Stoicism — Meditations from Marcus Aurelius, Letters from a Stoic from Seneca, and Enchiridion from Epictetus are my favorites on philosophy.

15. What does your content diet look like?

Having a healthy information diet is crucial to learning efficiently. I have certain creators in every topic I'm interested in whose posts I never miss.

Scott Galloway
Ben Thompson
Nat Eliason
David Allen
David Perell
Taylor Pearson
David Cain
James Clear
Tim Ferriss
Shane Parrish

16. Which historical figure have you learned the most from?

Without a doubt, Marcus Aurelius. Reading Meditations was my introduction to Stoic philosophy and philosophy in general. The wisdom and insights from his journal changed the way I approach life. If you're going to read it, I highly recommend the George Hays translation.

17. Which current figure have you learned the most from?

I have listened to every episode of the Tim Ferriss show. So while I've learned more from his guests than from Tim himself, his podcast and books have been massive resources for me. The fact that his podcast is still free is truly unbelievable. If you've never listened, I highly recommend just starting from episode one. You won't regret it.

18. If you could put one thing on a billboard, what would it be?

In five years you'll be glad you started today.

19. What piece of advice would you give to yourself ten, five, and two years ago?

Ten years ago, I would be 14, heading into high school. My advice would be stay the course, but spend more time reading and writing and less time playing Call of Duty.

Five years ago, I would be heading into my freshman year of college. My advice would be to sign up for a philosophy, a history, and a writing class. Almost every class I took at Princeton was math or computer science, because I really enjoyed them. But you can learn those skills outside of college easier than you learn about philosophy or history.

Two years ago, my advice would be take everything you plan on starting in six months and start it now! I started Dickie’s Digest and this website at the beginning of 2020, but wish I would have started sooner.

20. On what have you changed your mind recently?

I used to think that sharing things you’re learning or working on in public would be strange. There used to always be the voice in the back of my head saying no one would find it interesting or people would find it annoying. But what you learn when you start to share things like this is just how unique your perspective is.

Sharing exposes you to serendipitious encounters that would never have happened otherwise. I’ve made a bunch of friends and met quite a few thoughtful individuals in the last few months, just because I’ve put things I’m interested in out there. If you’re thinking about starting something like a newsletter or website, I can’t recommend it highly enough.

21. What is something you believe that most others don't?

I think Twitter will be one of the most valuable tech companies in the next five years. I’ve been a $TWTR shareholder for the last five years and it has been a bumpy ride. Clearly Wall Street does not believe this will be the case with the stock down 25% from its IPO price five years ago.

I could spend hours talking about why I believe Twitter is so undervalued, but I’ll save that for another post. If you haven’t used Twitter in the last few years, the product has evolved tremendously.

22. What is one habit you've implemented in the last year that has improved your life?

Since the start of 2020, I’ve committed to creating one piece of content every week. I set a low bar to begin with because there are few things more difficult than sitting down to write week in and week out, at least at the very beginning. As I’ve written more and more, writing has become less daunting and more natural. It’s a subtle shift, but you start to feel it a few months in. You feel more comfortable reading something and either summarizing it or crafting your own opinion on it. Your thoughts and words begin to flow more naturally, both when writing and when speaking.