On January 27, 2020, I had lunch with an entrepreneur friend. He encouraged me to share what I’d learned from scaling my bootstrapped company to over $10 million in annual revenue. I’m private and was reluctant, but I wanted to help others who were just like me when I started my company—people who didn’t know what they didn’t know. I agreed, and we began a 60-day challenge. We both posted content daily to help other entrepreneurs (see our challenge details here). That challenge began on March 9, 2020, and ended on May 10, 2020. I didn’t miss a day—and I learned to enjoy the habit of reflecting and writing every day.

That was five years ago. Since then, I’ve written and shared a post every single day. That’s over 1,825 consecutive days of sharing my thoughts. When I agreed to the challenge, I had no idea I’d still be posting five years later, but I’m glad I am.

Every March, I reflect on my writing journey. Here are a few reflections:

• Strike zone – I read a book a week, mostly biographies. I used to think of reading and writing as independent hobbies. But writing about the books I’m reading has enhanced my learning and thinking. Combining them feels like it’s put me in my strike zone.  
• Format – I’ve played with a few different formats for creating posts about biographies I’ve read. The format I like best is a deep-dive series about a biography (see examples here and here). I’m aiming to get back to that format, and I’m building software to help with the creation process.
• Luck – Bringing value to others by writing has increased my luck surface area and led to magnetic luck (more on luck types here). When I focused more on writing about biographies, it led to more magnetic luck. Entrepreneurs want to know what other entrepreneurs have figured out but don’t always want to read an entire book.
• Audio – Last year, I tested doing a solo podcast about the books I was reading. It was really an audio version of this blog. I did 100 episodes to get reps and learn. Audio is a powerful format but requires significantly more work than writing. Publishing a podcast episode daily wasn’t sustainable. I’ll revisit doing a podcast, but I’ll need more support next time, and I’ll test different formats.
• Level up – I want to take this blog to the next level and create more value for others. Adding a page detailing all the books I’ve read and creating a profile page for each book (see here) is an experiment and just the beginning.
• Annual contract – Every March, I’ve asked myself if I’m enjoying this and want to keep doing it. If yes, I re-up for another one-year contract with the option to renew. I’ve now signed through 2026.

Those are my reflections. I’m looking forward to the next year. I feel like year six will be epic!