Journal #2 - Not Judging Things by Their Cover

The obvious saying from childhood is commonly ignored, but a useful framework for detecting trends and become a unique person

I want to change my mindset to be an eternal optimist who absolutely loves change. I find myself naturally resisting change. Something new comes out and I by default am skeptical of it. I need to wait for someone to recommend it or tout it before I’m willing to change my mind and actually give that something a shot. This is how you discover new trends and technologies.

It almost all comes back to the saying “Don’t judge a book by its cover” which we all hear incessantly during childhood. Two nights ago, I was on my kindle browsing the top-selling fiction books. I read the title of each book, looked at the summary, and decided if I thought it was interesting. Then, I caught myself. I was almost literally judging all of these books by their covers. Instead, I picked the book at the very top of the list, the latest Lincoln Lawyer book called The Law of Innocence. I downloaded a sample and started reading it.

On the first night, I made it about halfway through the sample and was starting to get hooked. By the second night, I was looking forward to reading it before bed. I finished the sample and was so captivated that I decided to buy the book outright. I kept reading and reading. I was dying to know what would happen next and kept reading until I got to a natural breakpoint. I put the kindle down and saw that it was nearly 1:00am—I had started at 11:30pm. I had a huge smile on my face and was practically laughing at how incredible the conclusion to this particular subplot was. By far, this was one of the most exciting books I had read all year. How weird is it that a totally fictitious story could make me feel so elated and giddy? On that note, I went to bed.

Here I am, the next day, pondering how all of that enjoyment I was getting out of the book was purely because I didn’t judge the book by its cover. Now, I’m considering all of the things across my life that I judge by their covers—books, movies, new technologies, people, music, foods.


I had dinner with Jake Mor the other day. He convinced me to try a kumato tomato. This is what they look like:

Is that not one of the most unappealing tomatoes you’ve ever seen? As is, I’m not a huge fan of tomatoes. My first thought when I saw this poop-brown colored tomato was yea… I’ll pass on that. Turns out it’s delicious!

Judging things by your first impression seems like a very natural, evolutionary instinct. In practice, we’re often wrong and we liberally apply this rule across our lives subconsciously. Now, I’m consciously making an effort to not do that.

I ordered a new iPhone a few days ago. I was deciding whether to get the MagSafe charger. My first impression of it based on the Apple event demo was that it seemed unnecessary, bulky, and kind of lame. My 20-watt USB-C charger is probably faster. But you know what? Let’s give it a shot, maybe it’s really cool after all? So I tacked it onto my order.

I think this mindset is essential for being a successful entrepreneur. The most successful founders detect a new trend in society or a cutting edge technology and ride that wave of momentum to massive businesses. Imagine you were one of the first folks to start using bitcoin in 2009. I remember hearing about it back in the day and thinking that I didn’t really understand the purpose of it. Honestly, I still feel that way today. But imagine you heard about it, and just decided on a whim, you know what? I’m going to buy some because why the heck not, this new tech seems really cool. You’d be mega-rich today.

As someone who has an extremely mathematically-driven mind, I often struggle to adopt technologies that don’t have an abundantly clear use-case immediately. I need to understand exactly how using this new software will benefit me. When there isn’t a blatantly obvious benefit from a new piece of tech, I’m unlikely to try it. Instead, I want to be the one who figures out what the utility of a new piece of technology is.

I would put Notion into one of these buckets. I grew up using Google Docs and I didn’t really understand how Notion could be useful so I ignored it for a while. In hindsight, this is what I wish my framework of thinking was once Notion started becoming popular:

Step 1: Notice that people are talking about this new document-writing software called Notion

Step 2: Okay - let’s try it out. How is this useful. How can I start incorporating this into my workflow?

Step 3: Decide if it’s marginally better and more useful than Google docs and try to use it.

What I realized from my experience with Notion is that sometimes it is hard to succinctly state the benefit of a new piece of software.

Change is always difficult and uncomfortable, but embracing change is essential for business and life. All of these micro-decisions about software and other new things comprise your technological trajectory. If you on a daily basis reject change, your technology adoption trendline leads to you becoming a dinosaur—we all have a few of those in our lives (i.e. parents, grandparents, etc.).

I don’t want to become a dinosaur. Instead, I want to be at the forefront of discovery.