In 1992, riding a skateboard up and down a half-pipe wasn’t cool. The world turned its attention to street skating. Something with more edge, more rebelliousness, less polished and less about sponsorships and money.
But that didn’t stop a scrappy kid in Carlsbad from riding his skateboard everyday. Because Tony Hawk knew that if the world decided that vert skating was cool again, he would be ready.
In 1999, Tony Hawk landed the world’s first 900.
What will you do when things get slow? Will you wait for the world to tell you what’s cool and what’s not? Or will you tighten your bearings, wax the rails, and drop in?
Recording this episode was like frolicking in a bounce house for adults.
Andrew Barry is one of the most humble and joyful people I’ve ever met. He’s completely shattered all of my previous notions about what a CEO “needs” to be: fast-talking, a phone in each hand, scheduling meetings and forgetting their child’s birthday parties. Andrew’s life is proof that no matter how busy you are, there’s always time for a little curiosity. (Or in Andrew’s case, much curiosity.)
So, who is Andrew Barry? He’s the CEO of Curious Lion – a company that helps clients scale and improve their online learning. Andrew is also an avid blogger who writes about creativity, education, decision making, and group learning.
This is a far-reaching and wide ranging conversation, much like Andrew’s own openness to the world and it’s people. We talk Zen philosophy, Aldous Huxley, meditation, writing, music, flow states, life in South Africa, and so, so much more. We could have spent hours talking about every nook and cranny about life and growth. So expect to see Andrew on the podcast again sometime in the future.
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Today I’m joined by the bold and adventurous Shelby Smith.
Shelby Smith (@CoShelbySmith) is head of user onboarding for LingQ. She’s also a writer who discusses leadership, language learning, self-development, and why it it’s important to stand up for yourself to get what you want.
Deepu Asok is the author and illustrator of the wonderful and enlightening Visual Wisdom newsletter. He’s also the host of a podcast called The Happiness Hypothesis. He’s got a serious eye for designs that pop.
Deepu and I were dming over meditation and spirituality. But he had to get going, and asked to continue our talk over zoom some time. I said sure. And of course, I asked if he wanted to record our talk for the podcast. He said yes. And so, here we are.
Please enjoy my conversation with the wonderful and wise Deepu Asok!
On different schools of meditation and yoga (3:00)
The benefits of doing yoga before meditation (11:00)
Why meditate? (14:00)
“Philosophy doesn’t transform you. Practice transform you” (21:00)
“The lion is trying to help you, but it doesn’t know how.” (28:00)
On Happiness and work (37:00)
Three types of work (43:00)
Selling on Gumroad (50:00)
The differences between drawing and writing (55:00)
“You’re paying for the organization of the ideas” / Constraints (1:00:00)
Every idea you have, every concept, every word, every utterance, every tone…all of that is influenced by those around you anyway. You’ve got to acknowledge that and embrace that and ask, ‘how can I mix those together?’ Each of us is a completely different combination.
Salman has a heart of gold. I promise that you’ll finish this podcast with more inspiration than you had when you started. He’s one of those rare souls who knows how to do what matters in life without taking himself so seriously. Every time I interact with him, I feel a radiant golden energy enveloping me in a reassurance that it’s okay to be myself. I hope you feel the same way after listening to our conversation. Please enjoy!
Giving advice on Twitter (3:00)
“Insecurity work” (5:00)
Layers in writing (8:00)
“The hardest part of writing is talking about myself” (13:00)
Aren’t we all polymaths? (20:00)
“Being yourself isn’t the most effective growth strategy” (26:00)
I know I’m late in saying this, but the Internet is 4w3s0m3s4uc3. I’m getting help for my new consulting service from an experienced consultant in Australia. A generous young teacher from India improved my resume. And I had a two hour conversation with an artist from Wichita.
For many, it seems like the biggest barrier to doing good work is “three years of experience required.” But we can work around that.
By seeking people who have the experience. By being curious enough to ask them the right questions. And by being so enthusiastic about the work it’s almost overwhelming.
It doesn’t help to start by asking, “what should I do with my life?” because you “sort of” know the answer already. By asking someone what to do with your life, you’re seeking permission to do what you’ve always wanted to do.
Instead, try, “I really like what you’re doing. I want to do the same. But I’m not sure how to go about doing this.”
And how should you express your enthusiasm without stepping over boundaries? It’s like I said before. Ask the right questions.
If you don’t have “three years of experience” yet, enthusiasm and curiosity are your greatest assets.
And if we’re making things for our amusement, does that mean we shouldn’t share anything we make?
Of course not. Experiencing art we enjoy is like looking at a mirror. And as creators, we’re making mirrors for people to look at and see something we can’t see.
Some of us look at the mirror and notice technical finesse (or error). Some of us look and see emotions we can’t put into words. And some of us hear the subtle tempo changes.
The artist knows more about their art than the audience does. That is, until the artist shares their work. It’d be overwhelming for the artist to know all the ways the audience might experience the art.
When your work is out there, it’s out there. It’s impossible to control how the audience appreciates your art. To be upset that your art wasn’t well received is to be the mother who’s upset their kid didn’t want to live the way mother wanted them to.
It’s been so hard for me to keep this episode unreleased until today. I’m so excited that I get to finally share this with you all. This is the longest conversation episode to date. Austin completely and gracefully over delivered on everything I asked him. He’s the first guest to stand up and lean into the microphone during our conversation. I could feel his energy bursting from my screen.
…What I’ve been learning about the Internet is…you can grow exponentially through these scaled networks..but to me, what that means is your real life actions just translate to the Internet. Your real life actions are essentially compounding, right? We don’t really need the Internet to do that. Real life actions in the 1960s could have compounded as well. It’s always been there….
Austin is a true artist in every sense of the word. He’s one of those remarkable individuals who knows how to express art, even when using the most crowded market for creatives on the Internet (YouTube).
If you haven’t watched his mini-documentaries about the future of technology, please do. And if you have, watch them again. I get goosebumps every time I watch one of his videos. Especially this one.
A note on audio: something happened to how my computer was receiving Austin’s audio feed through Zoom. I could have said something during our conversation about this, but I didn’t. I didn’t want to interrupt the flow of the conversation. I’ve been kicking myself over that for weeks. Luckily, Austin was such an amazing guest so everything he says makes up for my mistake.
A note on future podcast episode numbers: I’m resetting the interview episodes. All numbered podcast episodes will signify that the episode is a conversation. All unnumbered episodes will signify that it’s an Akimbo styled episode: a short reading of one of my blog posts, or an improvised riff or story.
Consistent content. Even if you don’t think it’s good.
Austin’s background (3:00)
Learning multiple skills at the same time (8:00)
How much content should creators be pumping out everyday? (10:00)
Going off on the wrong path / A bedridden depression / Living in Berlin /Austin’s travels (11:00)
Experiences with Ayahuasca (If you’ve ever heard The Tim Ferriss show, you know the risks involved with this. Do your research.) (18:00)
“As consensus turns into a form of truth…” (32:00)
Fighting back against the daily darkness (35:00)
What happened after his Ayahuasca trip? / Being relentlessly yourself in your craft (39:00)
On compounding actions without the Internet (42:00)
Why did Austin decide to start making videos? (45:00)
How long does it take Austin to make a video? (48:00)
Thoughts on newsletters (51:00)
Why every creator should see themselves on an exponential curve (54:00)
A huge discussion about the ownership economy (56:00)
Appreciating the work you’ve done so far (1:18:00)
“Speed is a poison” (1:19:00)
Where’s the finish line? (1:23:00)
David Choe (1:25:00)
Staying anonymous (1:30:00)
Leaving your audience with a feeling (1:34:00)
Go beyond the limits of your medium / Austin’s definition of authenticity (1:35:00)
David Foster Wallace – This Is Water (1:48:00)
Austin’s favorite books (1:50:00)
How information itself is transforming with technology (1:55:00)
The real darkness of self-transformation vs “struggle porn” (1:58:00)
Low quality self-improvement advice (2:05:00)
Do we need mentors? / The mass pretending phase (2:08:00)
Lying to yourself on purpose (2:11:00)
Giving back (2:14:00)
Austin convinces me to drop Evernote for Notion (2:18:00)
Hi all. Welcome to another conversation about the pursuit of creative excellence. I’m so happy that I finally get to share this episode with you! What follows is an intimate, insightful, and entertaining conversation with a true artist — Phil Desforges. I highly recommend you browse through Phil’s portfolio while you listen to this episode.
How Phil developed his color palette
The art of building a world in your art
How photography saved Phil’s life
Why men should open up about their feelings
Sensitivities to music
Why Stoicism is important to Phil
Phil’s favorite movies and directors
On Casey Neistat
Following your gut vs your reasoning
The comfort zone and consistency conundrum
The nuances of creating on certain mediums, thoughts on Tik Tok
We find the answer when we first ask, what are we?
Well, I know what we’re not. We’re not a collection of numbers.
We like to focus on growing our metrics. Get more subscribers. Get more followers than we had last Thursday. But the numbers don’t define us. The numbers are something that somebody else invented. And we’re not defined by something that exists outside ourselves. So we shouldn’t tie our self-worth to something external. Because what exists outside ourselves could be taken away from us.
Put some distance between you and what you see. Who you are isn’t what you see. You’re not your social media numbers. You’re not the number of people retweeting your latest bit of wisdom.
What’s dangerous about tying our self-worth to numbers is that a number can always be higher. And it can always be lower, too, which is why we prefer them to be higher. Lower numbers means we’re less significant. Higher numbers means we’re accepted.
You’re a collection of experiences. But, like the numbers, you don’t have much control over your experiences, either. You couldn’t have asked your mother for an abortion.
But what you always have is control over your perception. You can choose how you’ll perceive the fact that you were born.
We lose our wallet in the same place we lose our self-worth. “Oh, it’s right in front of me.”
What’s in front of us is what blinds us. What we see always hides something else.
If you’re seeing numbers all day, then you’ll unconsciously tie your self-worth to the numbers. What gets measured gets managed, right? What gets measured gets managed by our ego. It’s our ego’s job to tie our self-worth to what we’re seeing on a day to day basis.
This is why it’s healthy to disconnect and go for a walk. Put nature in front of you, and you’ll soon realize how expedient the numbers are.