How do you read?

Plan Your Next: Letter No. 5

Hello from Laporte, MN! I have no idea where that is!

I’m at a cabin in northern Minnesota this week with some good friends, and I just got back from playing golf, scoring a 74 on 9 holes. What the hell! It was about 75, and I was wearing pants and a long sleeve shirt and K-Swiss shoes. Not that preparing my attire better would have made my game any more competitive, but it was a shit show from the start. I’m at a point where I’m not sure I should just give up or keep trying.

I’ve been traveling a lot lately, but the great thing about it is that I can spend more time reading, whether it’s in a Lyft, at the airport, or while flying. My reading habits might trail off a few days before a trip because I know I can make up for lost time.

In fact, I just finished A More Beautiful Question and Storm in a Teacup. Now I’m reading The Rational Optimist.

Which leads me into today’s letter about my reading habits. Enjoy!

I haven’t always loved to read

“Human beings have been recording their knowledge in book form for more than 5,000 years. That means that whatever you’re working on right now, whatever problem you’re struggling with, is probably addressed in some book somewhere by someone a lot smarter than you.” — Ryan Holiday

I used to read a bit as a kid but struggled to make time for it. Mainly because my priorities were baseball and art.

My life plan as seen through the eyes of 10-year-old Nate: Plan A was to make it to the big leagues. If by some silly chance that didn’t work out, Plan B was to take my talents to the baseball card industry as a portrait artist for cards like these. It didn’t matter that they were the least valuable cards in the set. Art was my way out of Brooklyn Park.

But none of that involved reading.

After I moved into my first apartment—while teaching myself design—I was reading mainly design books.

One of the first books I read as an adult was called The Tin Drum. A woman that I had a crush on asked if I had read it, and so of course I spent the next 3 days reading it front to back.

During that time, my sanctuary was at a Barnes and Noble where I would sit down for hours and read the latest books on design, right up until closing time, at least 3 days a week. It was my way of finding books for cheap and spending time

“When I get a little money I buy books; and if any is left I buy food and clothes.” — Erasmus, the 16th-century scholar

The first Kindle

It wasn’t until Amazon released the first Kindle that I started to read more consistently. I was slowly picking up speed but I was still reading just a few books a year at this point.

My first impression was that it looked like something that people back in the 60’s would imagine a reading device of the future to look like.

It was incredibly clunky, white, and had all of those buttons to navigate. This was not some design feat. But it worked, and like an iPod, it could hold hundreds of books in your pocket.

The paperback

For me, you can’t beat the experience of reading a paperback. I should probably read them more, as I’m sure it’s good for the soul. But to me, it has its faults:

  1. I’m definitely going to ruin the aesthetics of the book by destroying the binding (The designer in me hates this).

  2. Reading in the dark is difficult without an attachment.

  3. I can’t read multiple books without taking up space.

  4. I don’t always have a highlighter nearby to take notes.

But when everything lines up, I can’t hate on the paperback.


Since I don’t really commute, I find audiobooks even worse than reading paperbacks. The worst is that I can’t take notes or highlight passages and easily get them into digital form.

The Kindle; because there are no other decent e-readers

Since it’s rare that everything lines up perfectly, it’s the reason that the Kindle is so useful to me. It’s definitely not perfect, but as photographer Chase Jarvis says, “The best camera, is the one that you have with you.” The best tool for reading can easily apply to that as well.

Whatever it takes to inspire you to read more, the tool doesn’t matter.

My process

“A really good book costs $10 or $20 and can change your life in a meaningful way. It’s not something I believe in saving money on.” — Naval Ravikant

My single biggest problem with reading is that I forget a lot of what I just read after a few weeks.

When I’m reading using my Kindle, I highlight a lot. Sometimes it’s quotes, entire passages, or pages. Once those are highlighted, it’s difficult to go back through and read those on your Kindle, and so the biggest hurdle I had was getting those highlights out of the book and into something searchable.

You want to be able to access those quickly and easily.

To do that, whenever I finish a book, I use the paid version of, which connects to my Amazon account and downloads all of those highlights into their web interface. Once it’s there, you can deliver it to Evernote or anywhere else that you want. I initially wanted to get everything into Evernote, which is why I started using it.

So even though I have everything in one spot, I have found some useful ways to unearth a lot of those highlights.

One of those tools is called Readwise. It also connects to your Kindle highlights and will randomly select saved excerpts and email those to you daily/weekly/monthly. It’s kind of like getting reminders about old timeline photos from Facebook, but for books.

I’ve found this workflow to be incredibly useful to keep books you’ve read top of mind, helping to make sure you don’t lose the benefits from what you just read.


Question for you

How do you like to read a book? Are there any books that you might recommend at the moment?

Have a great week!

This is Plan Your Next. It’s a conversation about being ready for what’s next. Well, because there is always a next. I’m Nate, designer and conductor of this group.

If you have something to share or add, please hit reply and expect a response!