The Penguin Latte Podcast #12: Shelby Smith on Lessons From Failures, Language Learning, and Having the Courage to Get What You Want

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.

Listen on Spotify | Apple Podcasts | Watch on YouTube

Talking Points

  • Shelby’s backstory with the entrepreneurial spirit (2:30)
  • “I’m a day one listener of The Tim Ferriss Show” (6:00)
  • Action is the missing ingredient / Life in Ecuador (9:00)
  • Learning from having a failed business (15:00)
  • “I wrote that I was psychic” / How to handle job interviews if you never went to college (18:00)
  • Suggesting what companies do wrong (35:00)
  • What it was like to go for a year without social media, and all the unexpected changes that came from doing that [I can’t believe this is even a talking point] (41:00)
  • “Build a personal relationship with your ideas” / Experience with Write of Passage (1:00:00)
  • Shelby’s guiding principles (1:07:00)
  • On learning languages (1:15:00)
  • How we elicit meaning in language (1:25:00)
  • What’s the work you do that feels like play? (1:30:00)
  • When was the last time you were in flow? (1:35:00)
  • When do you feel dissatisfied? (1:38:00)
  • The final question (1:42:00)


The Four Hour Workweek

The Art of Learning

Deep Work


Discipline Equals Freedom


Tim Ferriss

Jocko Willink

Josh Waitzkin

Samuel Hulick

Cal Newport

Ray Dalio

Richard Turner




One click forward (and six steps back)

How long does it take to build something that lasts? Something evergreen? Something like…

A blog worth reading everyday?

A podcast worth sharing not only with your coworkers, but with your family and friends as well?

A piece of code that makes our lives a little less lonely?

A book that makes us feel emotions that we can’t name?

Awhile, I guess?

And how long does it take to delete something? A few seconds. Poof.

Every word processor and photo editing suite has a delete button. Even the analog world has delete buttons. (Trash cans for some people. Flamethrowers for others.)

Everything has a “new project” button, too. But clicking the “new project” button is not the same thing as building something remarkable. Building something remarkable takes brutal dedication, planning, and enough money to cover years of therapy. Starting a new project takes a single click (the same amount of clicks it takes to delete it). Anyone can take a single click forward. But who can take one click forward and six steps back? Who has that kind of humility? (Perhaps, you.)

The “build” button is a myth, a joke. There can’t be a button that aligns you with a clear goal. There can’t be a button that does away with your habit of going nowhere fast.

It takes one click to start a new project. It takes thousands of steps backward and sideways to build something that lasts.

More respect to the builders, please.

More respect to those climbing the mountain instead of causing an avalanche.

Penguin Latte Podcast 18: The Tyranny of Expertise

The impostor is right. It’s right because it knows that we’re not good enough. But the impostor wants us to stay where we are. So the trick is to realize that it’s only half right. Yes, we’re not good enough yet. So what are we to do about that?

Here’s a riff about impostor syndrome and the tyranny of expertise.

Episode Notes

The Art of Learning: An Inner Journey to Optimal Performance

The opening riff, Beginner’s mind

p.s – I’ll be releasing episodes once per week. I’ve had a few people say that they’ve been trying to keep up. (I can’t keep up, either.) I hope this new schedule will help.