Students need to struggle

Good morning!

Inside this Sunday:

  • I’m reading about how humans and companies grow at different rates.
  • I’m working on speaking in San Diego, a new website, and a writing challenge!
  • I’m thinking about the Pareto Principle.

Recently I’ve been thinking about how incredibly hard learning is.

Especially learning that leads to real transformation.

It’s more than just “The Dip” we experience when learning something for the first time.

You know that feeling where you hit a wall and it doesn’t feel like you’re learning anything?

Then something clicks, you get a breakthrough in understanding, and you keep going.

That’s the Dip.

I’m talking about the evolutionary realization that to transform, a part of you must be left behind.

Why is this so hard to do?

We’re attached to our identity, thanks to our ego.

We are comfortable with who we are.


We resist change.

And that’s exactly what learning is.

So we tell ourselves that it’s too hard, or too complicated.

“I don’t understand bitcoin, so I’m not going to waste my time on it.”

What we’re really doing is resisting leaving an old part of ourselves behind (the part that isn’t familiar with bitcoin) and embracing a new identity (#LaserEyes?).

My creator friend Karaminder reminded me of a great Paulo Coelho parable, The Lesson of the Butterfly, which reminds us that “sometimes, a little extra effort is precisely what prepares us for the next obstacle to be faced.”

This is a good reminder for us as teachers: students need to struggle, and we should resist the urge to give them the answer.

Till next time,



The most popular link two weeks ago was my first ever viral tweet – 211,000 impressions and counting.


Humans Grow Linearly, Companies Grow Exponentially

Khalid Halim is an executive coach to CEOs of venture-backed companies. He thinks deeply about human performance, emotion, and interaction.

I recently re-read a feature on him in First Round Review – Hypergrowth and the Law of Startup Physics.

He explores the idea that companies and people grow at different rates — and what this tension means for how both will break while scaling.

In Khalid’s experience, even incredibly talented people at fast-growing companies fall behind. He cites ego and company structure as two possible barriers to someone’s growth and proposes a few interesting approaches to solve this.

My 3 favorite ones:

  1. Talking about your last day first – this involves sitting down with a new hire to make a pledge. You, as a leader, actually make two promises: one to the continued growth of your new hire and the other to the company (and investors) for its continued growth. You pledge to your new hire that when, at some point, those two promises don’t connect, you’ll enter into an honest conversation about what’s next.
  2. Peak positive emotions – we operate at our best when we have peak positive emotions, and these come from outside your work – connecting with others, sleeping well, taking a vacation. Seek more of this out.
  3. Repair mode – related to the above point, our body has two modes on a cellular level: growth and repair. “It doesn’t go into repair mode if it has an unlimited supply of growth and fuel.”

Full 15-min read


Conference Speaking

By the time you read this today, I may already be on a flight to San Diego. My first flight since December 2019. I’m off to speak at the ASU+GSV Summit!

On the first day, I’ll be on a panel with some impressive guests. We’ll be discussing the rise of community-based learning. I’ll also be moderating two panels – on lifelong learning and the unbundling and re-bundling of education.

On the second day, I’m leading a workshop with my good friend and Curious Lion client, Phylicia Jones. Together we’ll unveil a new product to the world – the Curious Lion Learning Flywheel.

It’s not technically new, as we’ve been piloting it at PagerDuty, Pinterest, and Bolt. But this is the first time I’ll be sharing it publicly.

I cannot wait.

New Website

To prepare for the conference, we performed a makeover on the website, creating clear pathways for companies and creators (the two audiences from which I get clients).

Check out the new homepage and follow your pathway of choice – company or creator?

Ship 30 For 30

Starting next week, I’ll be taking part in a writing challenge to publish 30 essays in 30 days.

Writing online is perhaps the highest leverage skill I’ve developed in the past 1-2 years.

As I mentioned a few weeks ago, I didn’t write much for the first 6 months of this year.

While I’ve gotten back into it, this challenge is going to really kick it up a notch.

Join me and get $100 off

How Did You Learn That?

In ep 38, I soaked up the experience of a YouTuber with almost 6 million subscribers. Marina Mogilko’s journey from St Petersburg to Silicon Valley is wild. She shares her knowledge on how to build an audience, how to balance work and life, and how to use the power of leverage to be a superwoman.

More on episode 38

In ep 39, I bonded with recovered addict turned internet marketer Tim Stoddart. This conversation starts out by answering the question that anyone unhappy in their job often has – “How do I get started?”

More on episode 39


What are the minority of your actions that drive the majority of your results?


This email newsletter was originally shared with subscribers on August 8th, 2021. To receive the latest newsletters twice a month, sign up below!

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