One of the things that annoys my family and friends is that I’m vague when it comes to details. If they ask me questions about granular details, I usually don’t have an answer. If they ask a high-level question, I likely can answer. For example, what was the keynote speaker’s main point? I can answer. What personal examples did the keynote speaker use to support the main point? I may not remember (unless I took notes).

Over time I’ve realized that I’m not wired to remember granular details or live in granularity. It takes lots of energy and sometimes frustrates me to try to remember and process granularity. Having lots of conversations about granular things can also feel challenging. I have done these things in the past, can do them now, and will likely do them in the future. But it’s not my preference. To be clear, there’s nothing wrong with granularity. Many people enjoy it. It’s just not a good fit personally.

In the past, I’ve compensated for this shortcoming by taking detailed notes. More recently, I’ve learned to embrace my wiring and focus my energy on really understanding the big picture. My notes are less detailed, and I don’t view my tendencies as a negative anymore. I’ve realized that I naturally seek to understand the big picture, to understand high-level concepts. The big picture and high-level concepts are where wisdom usually resides. As a curious person who enjoys learning, that wisdom is exciting; it’s what I seek. As I’ve shared with my friends, I enjoy seeing the forest, not each individual tree.

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

• Sounding boards – It’s helpful to have smart, credible people to get candid feedback from and share ideas with. Sometimes they can accelerate good thought processes or highlight flawed thinking.
• Knowledge costs – Knowledge is never free. There’s always a cost. Everyone pays tuition (time, energy, or money). If you want knowledge, get comfortable with the idea of paying tuition and identify the form of payment that suits you.

Week one hundred seventy-four was a week of learning. Looking forward to next week!

I’m a pretty even-keeled person. A friend recently asked how I’m able to stay so calm in most situations. Part of it is my personality and upbringing. But also, I’ve learned to quickly filter out things others may choose to worry about—specifically, things outside my control.

When I encounter something that could be worrisome, I ask myself, “Is this within my control?” If the answer is no, I simply don’t worry about it. It doesn’t make sense to waste my mental real estate or time on something I have zero control over. I can’t influence the outcome, so I shouldn’t worry about it. That doesn’t mean that I’m not aware of it or that I ignore it. I take note of the situation, but I don’t go further than that.

Not worrying about things I can’t control is a helpful mental trick that’s allowed me to allocate more mental bandwidth to what matters most: things I can control.

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

• Bubbles – This week was a reminder that I enjoy being around people with experiences and perspectives different from mine. Living in a bubble isn’t for me.
• Growth mindset – There’s a common theme among investors and entrepreneurs who achieve extraordinary success: they focus on effort, not outcomes, and apply consistent effort toward learning. They all have a growth mindset.

Week one hundred seventy-three was a relaxed week. Looking forward to next week!

One of my personal characteristics that I’m mindful of is my capacity for empathy. Seeing something from the perspective of someone else or understanding how a situation makes them feel doesn’t come naturally to me. Over time, I learned that understanding the perspectives and feelings of others is a superpower. It makes navigating the world much easier, especially for founders (it’s hard to solve a problem unless you understand the feelings and perspectives of those living the problem).

Over the years, I’ve improved significantly in this area. I’ve tried various things, but what’s had the most impact is simple: spending time with people different from me and trying to understand their perspectives and how they developed them. Doing this (in a genuine and authentic way) has enlarged the lens that I view the world through. That’s made it easier to see things from multiple vantage points. I still may not agree with their perspective, but I can see things through their lens and understand how they feel.

I’m still not an overly empathetic person. But intentionally spending time with others with different perspectives has enhanced my capacity for empathy. It’s something I want to continue doing as long as I can.

I’ve been posting daily since 2020. After three years, it’s still something I enjoy and get a lot out of. When I first started, lots of low-hanging fruit was available—I had many experiences as a founder that I could reflect on and identify insights from. I wasn’t used to sharing my thoughts publicly, though, so it took energy to crystallize my thoughts and craft a post that people could understand.

Now that I’ve been doing this for a few years, I can write a post with minimal effort. I’ve built muscle memory around writing and gaining clarity of thought.

I focus my effort now on identifying interesting things and insights to share. I’ve become more intentional about acquiring knowledge related to concepts I want to understand and attempting to develop unique insights about them.

The result of all this is that writing daily posts is still challenging, but in a different way. I began by being more intentional about developing the habit of sharing my crystallized thoughts. I’m now more intentional about understanding a concept and identifying insights related to it. Focusing on concepts is more difficult. I’ve had to adjust my habits to support the change, but I’m happy with the adjustments. I’m excited to be learning about interesting and difficult concepts. I’m even more excited by the challenge of coming up with unique insights.

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

• Decision feedback – I’m curious to try out the new technique for improving decision-making that I wrote about recently. I’m going to start asking a few people I think highly of if they’ll provide feedback.
• Jump start – Sometimes it’s good to have a change of scenery for thinking. For some reason it jump-starts my creativity and my ability to recognize insights.
• Frustration – Earlier this week, I was frustrated about a few things that were out of my control. Exercising and talking through my frustrations with others was helpful.

Week one hundred seventy-two was a frustrating week. Looking forward to next week!

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

• Adjust solutions, not people – Trying to bend customers so they can use what you’ve built doesn’t end well. The best solutions are built and scaled when you’ve listened to what customers want and adjusted the solution to meet their needs and solve their pain point. Adjust the solution to people, not people to the solution.
• Holiday – It was great to spend time with family and friends. I was able to get some good reading in, too.  

Week one hundred seventy-one was a short week. Looking forward to next week!

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

• Entrepreneurial swings – I caught up with an entrepreneur friend. Two years ago, things didn’t look good, and he wasn’t sure his company would survive. Today it’s thriving and kicking off more cash than he knows what to do with. Things can swing from one pole to another fairly quickly for entrepreneurs. The key is to persevere.
• Q2 – The quarter is officially over. It went by quickly. Hard to believe we’re halfway through the year. Looking forward to the second half of 2023.
• Workflow management – I’m optimistic about workflow management technology. Companies can’t just throw people at problems anymore and will actively be seeking software solutions. Many companies’ focus on efficiency is blowing up a strong tailwind for start-ups solving painful workflow management problems. These are B2B companies solving unsexy problems, which is a combination that can create a great foundation for a business.
• July 4th – Next Tuesday is a holiday. Looking forward to spending time with family and friends and reading a few new books.

Week one hundred seventy was a steady week. Looking forward to next week!

When I started posting daily in 2020, I had a decade-plus of entrepreneurial experience from building a company. I thought about those experiences and identified insights about entrepreneurship. Then I shared my insights in a way that people could understand (and hopefully find useful).

Lately, I haven’t been getting as much from the process of creating my posts. I thought about why I feel this way and concluded that I haven’t been as consistent in sharing insights in my posts. More of my posts have contained information but not shared deep understandings. I realized that the process of gaining an understanding of a topic and then distilling and sharing it concisely is fulfilling. It isn’t always easy to come up with insights and communicate them, but I’ve enjoyed it when I have.

I want to get back to writing more insightful posts. To do so, I’ll need to accelerate the rate at which I acquire knowledge on certain topics and come to understand them.