I’ve been sharing my thoughts daily for over three years now. I was recently asked how I’ve come up with a topic every day for 1,000+ consecutive days. It’s taken a bit of time, but I’ve developed a simple system. Here’s how it works:

• I keep in the back of my mind that I must write a post. So, I’m subconsciously on the lookout for insights and interesting information. If I read an article that catches my attention, I note it. If I’m thinking about something or have an insight, I note it.
• I capture a note in one of two ways. The first is email. I’ll send myself an email with the thought as the subject line. Sometimes I add links or additional thoughts in the body of the email. I tag these emails as blog content and archive them. The second is the Notes app on my iPhone and laptop. I have a single note with a running list of thoughts, insights, and links to other people’s writings that caught my attention. Lately I’ve been capturing more notes via email.
• At the end of each day, I review emails tagged as blog content and my Notes app. I choose the topic that resonates most with me. Then I think about it a bit more and start writing.

The most important and unexpected benefit I’ve gotten from this system is that it instilled in me the habit of capturing my thoughts. Recording my “lightbulb” and “shower” moments has been invaluable. Instead of losing these thoughts when the moment passes, I now keep them top of mind or at a minimum recall them later. This has enhanced my reflection process and ability to uncover insights I otherwise would have missed.

That’s my system. It’s simple and fairly low-tech.

This is my one-hundred-sixty-fourth weekly reflection. Here are my takeaways from this week:

• Schedule – This was the third full week of my schedule experiment. My purpose for reading something and the type of material affects how fast I read. For example, if I’m trying to understand a new, complex subject, I read more slowly (which I think is a good thing). Mornings are best for me for this kind of reading.
• Supply and demand – When supply far outpaces demand, people on the supply side will experience unwanted outcomes. In investing, this can occur when capital far exceeds quality destinations for capital. It’s better to be investing when the opposite is true.

Week one hundred sixty-four was a productive week. Looking forward to next week!

My early years were foundational for me. I had lots of energy and crazy ideas as a kid. My mom always listened to those crazy ideas and gave me the leeway to make mistakes. She encouraged me to work hard and, when things didn’t go well, reflect on it, dust myself off, and try again. Over the years I learned, became confident, and realized I love business and entrepreneurship. I’m super appreciative of her approach, her love, and most all, her patience with me!

Happy Mother’s Day, Mom! Thanks for being a great mom!

This is my one-hundred-sixty-third weekly reflection. Here are my takeaways from this week:

• Schedule – This was the second full week of my schedule experiment. This habit is having a positive impact on my knowledge acquisition. I’m starting to think about a daily goal for number of pages read.
• Insights – Developing insights from data that’s readily available won’t generate outsize outcomes. Many people can do that. Cultivating qualitative insights and making decisions based on them isn’t something everyone can do. Therefore, those insights generate outsize outcomes when they prove to be correct.
• Consistency – Someone pointed out that one of my superpowers is consistency. I am consistent, but I hadn’t considered it a superpower. I’ve been thinking more about this.

Week one-hundred sixty-third was a great week. Looking forward to next week!

This is my one-hundred-sixty-second weekly reflection. Here are my takeaways from this week:

• Schedule – This was the first full week of my schedule experiment. During week one, I was able to do significantly more long-form reading. And I had some interesting insights as a direct result.  
• Banking – The First Republic Bank failure wasn’t a surprise. Interest-only mortgages being a contributing factor was. I’ve been thinking about the impact this product likely had on high-end real estate prices. It’s also got me thinking about where we were in the credit cycle when these loans were made and where we currently are.  
• Timing – I’ve been thinking about cycles and timing of ideas. Understanding where we are in a cycle can help you understand when the time is right (or wrong) to do something. Still thinking about this and getting the perspectives of others.  

Week one-hundred sixty-second was a productive week. Looking forward to next week!

This is my one-hundred-sixty-first weekly reflection. Here are my takeaways from this week:

• Schedule – I’m excited about my new schedule. Can’t wait for next week—the first full week. I’m curious to see what impact this change will have.
• Consensus – I had a few conversations with entrepreneur friends who have a passion for investing (public and private). I noticed they’re adopting the same viewpoint and risk tolerances at the same time. They all have the same reasoning (which I must admit is grounded in logic). I didn’t hear any contrarian views, which was surprising for this group. No one is considering a new or better approach.
• Patience – Sometimes people take a different path to get to the same conclusion or insight as you. You might not agree with their path or like their pace. This week reminded me to be patient and to remember that what’s important is that you both ended up at the same place.

Week one-hundred sixty-one was a calm week. Looking forward to next week!

I’ve developed a habit of starting my day with physical activity. Walking, weights, etc. Getting my blood flowing and working up a nice sweat. It’s been a great way to get the day going, and it gives me energy throughout the day.

I’m a morning person. My brain is firing on all cylinders when I first wake up. I have my best ideas and clearest thoughts early in the morning when it’s quiet. Knowing this, I didn’t always feel like I was getting the most out of my most productive time, since I was exercising instead of thinking.

I want to be intentional about reading more long-form pieces as part of my daily learning habit. I usually do this in the evening. Sometimes I’m tired, which affects how much I absorb. And I tend to put off reading anything that requires deep thinking.

This week I decided to tinker with my schedule a bit. My goal is to figure out what the right activity is for my most productive early-morning hours.

I’m going to experiment with starting my day reading long-form writings. I plan to focus on things experts have written about topics I want to learn more about and on dense business materials (e.g., white papers and reports). The idea is to be able to think more and absorb more of what I’m reading because my brain will be fresh. I’ll keep reading in the evening too, but I’ll focus then on stories and autobiographies where I just need to follow along. As for my workouts, I’m aiming to do those at lunchtime.

I’m curious to see how this experiment works and what I learn from it.

I was asked about my plans for retirement recently. Here’s how Merriam-Webster defines “retired”:

Withdrawn from one’s position or occupation : having concluded one’s working or professional career.

A few years ago, I had the opportunity to take a few months off after rarely taking time off for the last decade. I gave myself permission to disconnect. I wasn’t thinking about anything that resembled work. I wasn’t thinking about how to solve problems; I wasn’t tinkering with new ideas. I wasn’t checking email (regularly). I wasn’t talking business with anyone. I focused on doing things I couldn’t do while I was leading a company, like spending a few weeks with a family member who was recovering from a life-threatening medical condition. I completely withdrew from work.

I enjoyed the time off and being able to reconnect with people. It was a much-needed respite after years of grinding. But I also felt like I was at a standstill. As a founder, I was constantly having to rise to the occasion to overcome the latest hurdle. That kept me in perpetual learning and growth mode. I didn’t always enjoy the things I had to work on or learn as a founder, but I enjoyed the personal growth. My time off felt odd because I wasn’t being challenged or growing—not quickly at least. Mental stimulation was missing.

I did learn from the experience how powerful controlling your own time can be. Other people have affected my calendar since I was a child. If it wasn’t a school schedule, it was a work schedule or a business issue or something or someone else materially impacting how I spent my time. But during my time off, my calendar was under my sole control. I wasn’t working on stuff I didn’t want to work on. I wasn’t spending time with people I didn’t want to spend time with. I was in complete control of my time. It was quite liberating.

At the end of my down period, I concluded that my goal isn’t to retire. I’ll never want to retire (in the traditional sense). I’ll never want to walk away from the professional things I enjoy and the mental stimulation they bring. Instead, I want the freedom to work on the things I enjoy and that are mentally stimulating.

My goal isn’t to retire—it’s to control my time in perpetuity. I want the freedom to work on things and with people that bring me joy (so it doesn’t feel like work). If it doesn’t feel like work, I’ll end up doing more of it. I’ll be as engaged and busy as ever!

My retirement plan is to never retire.

This is my one-hundred-sixtieth weekly reflection. Here are my takeaways from this week:

• Runway – A few early-stage founders I know are running out of runway. Founders who can’t raise more capital will have to start making tough decisions. You can’t kick the can down the road when you’re out of cash.
• Venture – I chatted this week with a few high-net-worth people who made their wealth building tech companies and invested in venture capital funds. They’re more interested now in investing in traditional companies that generate cash, not venture-backed companies or venture funds.
• Founder hunger – A founder friend told me about what he’s doing now. Even though he doesn’t have to do anything (he’s financially set), he’s a founder at heart and still has a hunger and drive to try and build new things.

Week one-hundred sixty was a good week. Looking forward to next week!

This is my one-hundred-fifty-ninth weekly reflection. Here are my takeaways from this week:

• Financial leverage – I spent part of this week thinking about leverage in the financial system. Leverage is common in business, but when it becomes excessive it can cause problems. I believe there’s a high probability that there’s a material amount of leverage in the financial system that we’re unaware of. It’s hidden for now. When it’s exposed, it may cause problems.
• Being present – I carved out time this week to celebrate with family, shutting down everything else to make sure I was present. I’m glad I did.

Week one hundred fifty-nine was a steady week. Looking forward to next week!