I love the Christmas holiday. It’s a great opportunity to spend time with family and friends and eat amazing food. Historically, the week between Christmas and New Year’s is slow, business-wise, which I enjoy. It’s usually a week when I don’t have to worry about emails, calls, or any other fire drills. I’ve enjoyed spending this time reflecting on the past year and thinking about the future from a high level.

I’m looking forward to the rest of the week.

With the year ending soon, today I spent some time reflecting on the last twelve months. If I had to sum up 2023, I’d characterize it as a year of learning.

At the beginning of the year, I knew I wanted to learn a complex, difficult topic as rapidly as possible, so I spent time fine-tuning my approach to learning. I then used those newly refreshed learning skills to learn as much as possible about my target topic from people who’ve mastered it. I reflected on their wisdom and looked for insights they and others weren’t aware of. Knowing something and applying it are two different things. I tend to know I’ve mastered something when I can apply it successfully. I applied what I learned from the masters, slightly modifying things based on my insights, in an iterative testing approach. Most tests were successful and showed I understood the concept well. Some failed, and I learned even more from them.

I feel good about what I learned this year. It may have a material impact on the rest of my life. I’m excited about 2024. I can’t wait to apply what I learned in 2023 and start the learning process again with a new topic!

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

• Project – This week I began collaborating on a project I’ve been considering for a few months. We’ve started some testing with ChatGPT and had some interesting results. It’s been fun and a great learning experience so far. I’m excited about the possibilities if we’re successful.  
• Christmas – I’m looking forward to spending quality time with family and friends . . . and eating some amazing Louisiana cooking!
• Countdown – There’s one calendar week left in 2023. Looking to make the most of it on the personal front.

Week one hundred ninety-five was another week of learning. Looking forward to next week!

Last month I challenged myself to read an 800-page book over the Thanksgiving holiday. Yesterday, I shared my takeaways from that challenge.

Today I’ve decided what I want to read to meet my Christmas reading goal. I’ve purchased two books on a new topic I’m interested in understanding—one roughly 500 pages, the other about 200. So, 700 pages total. My goal is to finish both books over the Christmas holiday and go into the new year with a better understanding of the topic.

Looking forward to this challenge. Wish me luck!

Last month, I set a Thanksgiving reading goal. I’d been putting off reading an 800-page book for months. I didn’t want it to sit around any longer, making me feel guilty, so I challenged myself to read it during the Thanksgiving holiday. The goal ended up being a stretch goal. It was more aggressive than I realized. I didn’t factor in enough time for holiday activities, so I didn’t finish the entire book by my November 26 deadline. But I got close and did so shortly after Thanksgiving.

Overall, the challenge was a success, and I learned a lot from it. It ended up being a great motivator. I was excited to absorb the wisdom in the book but, even more so, motivated to accomplish my goal. This ended up being a great combination to prompt me to read a book I otherwise might not have gotten around to reading and to do it relatively quickly. The challenge also let me scratch the itch of accomplishing something difficult—something I enjoy but don’t normally experience during a holiday. Last, it forced me to be more intentional about using some of the reading techniques I learned about this year.

The holiday reading challenge was a success and something I want to do more consistently. I’ll start thinking about what I want to read during the Christmas holiday. If my experience then is as positive as it was at Thanksgiving, I’ll consider making this a habit.

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

• Shopify – Chatting with the Shopify CEO this week was amazing. His focus on helping people achieve independence through entrepreneurship stuck with me. Entrepreneurship is a force for economic mobility, and there’s a big opportunity to build products that help other entrepreneurs succeed.
• Events – I met some impressive people at events in Atlanta this week. I want to be more thoughtful in 2024 about attending interesting non-tech events.
• Countdown – There are two calendar weeks left in 2023. With essentially one business week left, everyone’s making a mad dash to get anything still open wrapped up.

Week one hundred ninety-four was another week of learning. Looking forward to next week!

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

• Fundraising – I chatted this week with two founders who are finalizing fundraising rounds. They’re wrapping up diligence and have target close dates in the next week or so. I suspect most investors and lawyers are aiming to get most deals done by December 15.
• Serendipity – I ran into someone I haven’t talked to in years. We caught up, and I learned that he has expertise that will be helpful with something I’m actively working on. He even offered to help. I’ve benefited from serendipity many times, but I’m still surprised by its power.

Week one hundred ninety-three was another week of learning. Looking forward to next week!

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

• Home stretch – It’s December. We’re in the last leg of the year. I want to make these last few weeks count. My intention is to focus on only the highest-priority things for the rest of the year. 
• Daily habit – I’ve been intentional this year about learning something new every day. This week I noticed that I felt unsettled one day when I hadn’t learned anything new. It was a welcome feeling because it meant this habit had been formed and my mind was expecting something new. Before the day was over, I cracked open a book on a topic I’m interested in.

Week one hundred ninety-two was another week of learning. Looking forward to next week!

In 2022, I realized the power of a foundational habit. Identifying and committing to a daily foundational habit greatly increased the probability of my sticking with other daily habits. When I consistently complete all the things that I decided need to be daily habits, my chances of reaching a desired destination or objective increase drastically. I like focusing on habits and systems over results and goals.

With the new year approaching, I want to start working on my 2024 habits. Before the new year begins, I want to crystallize where I’d like to be by the end of 2024, identify the new habits that align with that destination, and identify the foundational habit that I need to focus on.

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

• Thanksgiving – It was great to have time off yesterday to spend time with family and friends and eat amazing food.
• Reading – I’m using my downtime during this holiday to hit my reading goal.
• VC firm origin stories – Company origin stories are always interesting. This week I stumbled upon a podcast on which the origin story of a successful VC firm was shared by one of the firm’s founders. It was great and got me thinking about a few ideas. I’m going to look for more origin stories of unorthodox investment firms.   

Week one hundred ninety-one was another week of learning. Looking forward to next week!