🦊 Sketching Kauai

Hey friends,

I’m back from a long overdue break—I escaped to the beautiful island of Kauai in Hawaii, and spent a week there relaxing, eating, swimming, reading, and somewhat unexpectedly, sketching. I’m grateful I had the chance to go, as it was the first real vacation I’ve had in a long while.

At the last minute, I packed a small notebook and a Pentel brush pen. I learned about this very unique pen while watching Jess Karp’s video about pen drawing.

What I love most about a brush pen is that you can do very fine strokes as well as thick strokes, and even a bit of scratchy shading. It takes a bit of getting used to before you find a level of control you want, but the reward is totally worth it.

My first sketch was drawn in a rush and on a whim. Some friends of ours were visiting the island at around the same time, so I decided to welcome them with a little drawing. It was my friend’s mother’s birthday, so I dedicated it to her:

I did the above sketch quite quickly, and discovered how difficult it is to draw the sea. You don’t have much variation in color with a single pen—any black is very black, and so you have to be really creative to try and create different tones.

The other thing about ink-only is that once you put a line down, you cannot erase it (like with pencil), and you cannot undo it (like on the iPad). You have to be pretty thoughtful and plan a bit more with the sketches.

All that said, I still really enjoyed the creative constraint. It kept things simple: I have one pen, and everything must be drawn with it. This can be liberating, because I don’t have to worry about pencil vs pen linework, or coloring, or…

Creative constraints are freeing.

Most mornings I would hang out at the front lobby area which had a view of the beach. I wanted to sketch it, but realized I can choose to modify the sketch however I like. So I altered the perspective a bit and gave myself a chance to focus more on the details of the trees and rocks.

After a few days, I felt compelled to draw one of the lovely parrots who lived at the resort. There were four parrots for me to pick from, but something about this one’s beauty and personality drew me to them. I worried that the black-and-white sketch would do a disservice to its beautiful colors, but then again, all ink sketches are a compression to capture some essence of the real world. I accepted my constraints, and kept drawing.

I’ve never done live sketching before, so this practice was a totally new experience and challenge for me. It was particularly tricky to draw this parrot as it kept dancing and jumping around 😅 But that made it more fun, too.

I really enjoyed how meditative the experience of live sketching is. Instead of striving for perfection, I can just enjoy what I’m looking at, immerse myself into it, and before I know it an hour or two will go by. I feel really relaxed after such a drawing session.

Drawing is a meditative act.

The next day we went to the beach, and I was captured by the lifeguard’s station and surfboard. It was incredibly tricky to draw this because the wind was blowing so hard. Somehow, I managed.

I gifted the sketch to the lifeguard and had a brief conversation with them. After being there for a few hours, I realized they probably don’t have a lot of casual convos—most of their interactions are either instructions on the speakerphone yelling at people to stay away from the strong current, or running and leaping into life-and-death situations.

If you can, say hello. Talk to people. You never know the impact you might have on others.

I then visited a coffee shop called Dark Horse coffee. I really loved how big and spacious it was, and was particularly drawn to the giant fan on the ceiling. Apparently it is known as “big ass fan,” and people come just to see it 😂

I was pretty intimidated by the number of objects and furniture in the scene. How was I supposed to capture it all? So I decided first to focus on just the fan. After a little while, I realized you can’t really capture the scale of the fan without drawing everything else. And my little notebook was just too small to capture it without making everything really tiny.

So I abandoned the big ass fan, and started a fresh page. I picked a few things to focus on — the counter with the unique rock wall, the espresso machine (I’ve always wanted to draw one of those!), the door, windows, and set of table and chairs. I also added a little sign with their logo (which they didn’t have posted anywhere) as a fun addition.

I gifted the sketch to the two friendly baristas, who really appreciated the sketch. They said they’d put it up on the wall later. So if you ever visit Dark Horse coffee in Kauai, let me know if it’s up there, will you? :)

Gifting sketches is a rewarding practice of letting go.

My final sketch was of this silly sign that always made me laugh:

It was supposed to make me exercise more caution, but I always looked at that slipping dude and thought, “That guy is having a TON of fun.” I mean, just look at his hands!

When I sketched this sign, I added some important details to ensure the picture tells the truth: This man is having the time of his life.

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Quick Links

Tim Hughes – Why Stories Matter — I sat down with Tim on his podcast to talk about the story behind my book and answer the question: “Why the heck did this tech startup dude write a book of fables?” In the process, we explored the importance of stories in society, and the greater mission of fables I’m embracing.

Jack Conte - Death of the Follower & the Future of Creativity — This is a spectacular talk on the past, present and future of online creativity. I expected a bit of bias given Jack is the Patreon CEO, but I found myself coming out inspired: I need to think more about what I want to do next, and how I want to show up online. I know I want to write fables, make books, art, stickers, but how do I want to put my work out there? How do I want people to participate in it? Important questions to ponder.

Literary History - Anniversary of The Little Prince’s publication — If you know me, you’ll know The Little Prince is my favorite book. I loved this tribute to the book on its anniversary. In particular, I loved how it explored the initial reception of the book: People didn’t get it. It was mostly ignored at first. A great reminder that the best creative work is often misunderstood in its time, and only appreciated later.

Ted Gioia - The State of the Culture, 2024 — This post made the rounds back in February, and I’m still thinking about it. “The tech platforms aren’t like the Medici in Florence, or those other rich patrons of the arts. They don’t want to find the next Michelangelo or Mozart. They want to create a world of junkies—because they will be the dealers. Addiction is the goal.” … and … “Here’s where the science gets really ugly. The more addicts rely on these stimuli, the less pleasure they receive. At a certain point, this cycle creates anhedonia—the complete absence of enjoyment in an experience supposedly pursued for pleasure.” … and … “In the year 2024, this is what we do for fun. But it doesn’t bring happiness.”