What’s the opposite of a winner?

Not a loser.

The opposite of a winner is someone who doesn’t know that they’re capable of being a winner.

You could finish last, and still learn something valuable. Or you could finish last, and quit because the skill ceiling is too high. It doesn’t matter if the game is too hard. It doesn’t matter if the grammar is too complex. What you measure is your reward.

You could cheat your way to first place, and become a better cheater. You could fail your Japanese class, but still know the difference between “に” and “に.” In both cases, you’re a winner: you’re still gaining something.

The question is: what are you trying to win?

Waking up on purpose

You open your eyes as the alarm shrieks you out of your dream. Or maybe you’re one of those freaks who “rises with the sun,” as if your body is in a perfect cosmic alignment with the universe. Either way, you’re awake.

On a typical day, say, on a regular ol’ Tuesday, what does the first 15 minutes of your morning look like? Do you flood your psyche with information? Do you allow buzzers, bells, and airhorns to occupy your mind? Or do you employ silence as the canvas on which you will draw the roadmap of your day?

Whatever you choose, airhorns or canvases, you’re choosing intentionally. There’s no use blaming anyone but yourself for your muddy thinking and directionless days.

The smartest people I’ve ever met are those who intend to wake up on purpose.

Thoughts on how to make newsletters better

Getting better at a game means getting better at thinking about how to play the game. It’s called meta-gaming. Even Monopoly can be meta-gamed.

If you’re a newsletter writer, it’s likely that you follow a lot of newsletter writers on Twitter. And so all you see is newsletter meta-game. This is the best platform. No, this platform is better. This is how you standout. No, that’s not how you standout anymore because now everyone is doing that. Newsletters aren’t dying. No, newsletters are dying and if you subscribe to my newsletter I’ll tell you why.

It’s as if all these newsletter writers are writing for other newsletter writers.

Your readers probably aren’t other newsletter writers.

To avoid the trap of newsletter meta-gaming, here’s a few simple questions.

Why should your readers keep reading your newsletter?

What would your readers say to their friends about your newsletter?

What’s cool about your readers?

What makes your readers different from their readers?

How can you be sure that your readers don’t become a commodity?

Remember your readers, and they’ll remember you. That’s all that matters.

The sound of crickets

is an acquired taste.

You wrote and deleted and rewrote and revised and got feedback and would not sleep before it’s done.

And then?


The good news is that crickets aren’t a tough crowd. They’ll always fill the seats if nobody else shows up. They’re easy to impress. And they’re bad at throwing rotten tomatoes.

The charlatans won’t sleep until they hear the sound of praise.

The most successful creatives work the crowd of crickets.

Hey Penguin – Week of July 20

newsletter cover 1

Hey all. Welcome to the first Hey Penguin. This is a behind-the-scenes look at what I’ve been learning and applying to the content that I make. These are the tools and ideas that I’ve been using to feed the blog, podcast, and the way that I live.

Consider this newsletter as evidence that there’s no such thing as good ideas pulled out of thin air. There’s no lottery ticket. Only process.

I hope you’ll find these resources helpful to you as well.

[note: I’d like to make this an email newsletter. See the note at the bottom for more.]

What I’ve been thinking about: Reiteration. Alleviating dissatisfaction by treating everyday (and every project) like Groundhog day. Quit doing what isn’t helping you get to where you want to go. This newsletter, like everything else, is going to go through reiterations. You can reiterate your narrative. You can adjust your story as you see fit.

You can’t become who you want to be unless you start from who you are now. You need to go through steps 1 through 9 before you get to step 10. You need shoulders to stand on. Even if they’re weak shoulders. Even if they’re step 1 shoulders.

For more on this, here’s You can walk on water – a popular blog post from last week.

Podcast that’s blowing my mind: Naval on wealth and happiness.

Every ambitious creative person needs to listen to this podcast from start to finish.

Naval Ravikant is Marcus Aurelius plus Warren Buffet. I haven’t heard one thing from this guy that I disagree with. He’s a rare prophet who knows exactly what the future of work will look like. Lean into what he says about using software to leverage creativity to build assets while you sleep.

What I’m reading and applying to my work: This Is Marketing by Seth Godin. I wouldn’t be writing this newsletter if it weren’t for this book. This Is Marketing is helping me solve several tiny questions with major implications about my work:

Who is this for? (The biggest one.)

What is this for?

What promises am I making to the people who engage with my work?

Why should my content exist?

(I also see overlap with Carl Jung’s psychology of ideas. But that’s a different post for a different time.)

Which brings me to…

The book that I’m revisiting (sort of): Essentialism by Greg McKeown. I’m not reading it now, but I’m keeping the principles in the back of my mind. The 80-20 rule. Not multitasking. Taking breaks. Sleeping. Removing clutter. Seth Godin’s book is unlocking all the ways in which I can make great content for people who care. But it’s coming at a price. I often think of dozens of ideas for content at the same time. On the outside I look calm. But on the inside it’s like I’m going to explode. So I need the 80-20 rule. I need to take breaks. I need to remove clutter. I need to create space and time to focus on “what’s meaningful, not what’s expedient.”

Also, Captain Sinbad has a great video on the feeling of creative overload.

Community I wish I had joined earlier: Indiehackers.com. This is a community for people who buy mushroom coffee because they heard about it on Tim Ferriss. It’s a community of entrepreneurs, content creators, developers and builders. There’s no hustle. It’s full of smart, conscientious people working to make things better.

The great thing about this website is that you can see what other people are working on. There’s little survivorship bias because you can see peoples pivots and mistakes, too. I hope this community is around forever.

App that I’m obsessed with: Hemingway. Writing is now solved. For the last week, I’ve been putting every blog post through this app. It’s shown me errors that I’ve never considered before. It feels like cheating. (Put other people’s writing through this app. You’ll see things you’ve never seen before.)

Strange coffee that I’m addicted to: Foursigmatic’s Lion’s Mane dark roast. This is a coffee that’s made with mushrooms, and it’s fantastic. It doesn’t taste like mushrooms. It tastes like an excellent dark roast. I don’t know if it’s placebo, but this coffee makes me smarter. At least to the extent that I don’t check Twitter while I’m writing a sentence. And no, they don’t sponsor me.

Chrome extension that’ll lower the price of the strange coffee that I’m addicted to: Honey. This extension browses a database of coupons at checkout when you shop online. I used it to get a discount on the mushroom coffee. It’s amazing. Don’t buy another product online before installing this app. And if you use Firefox, sorry. There’s no hope for you.

A note about the future of this newsletter.

I’d like to make this an email newsletter. Starting an email newsletter isn’t free. It’s a major goal of mine to make content like this for a living. So I’ll need your help. Consider supporting me on Ko-fi. It’s a small, one time donation of $3. Every bit helps me to keep showing up to serve you.

I’m also thinking of starting one on one services that I can provide to creatives who feel stuck. I’d make it personal, focusing on what’s blocking this specific person. Kind of like unlicensed therapy for stuck creatives.

Buy Me a Coffee at ko-fi.com