Shit You Don't Learn in School

Steph and Cal are back to take stock of a wild 2025 — the wins, the bad experiments, the money mistakes, the obsessions that stuck, and the questions that refused to go away. From health and work to travel, marriage, and what comes next, this episode is a reset and a preview of the season ahead.

Resources:

• Surferdiary.com 🌊
• Build your own apps course

Quick note: This episode was recorded in December 2025. Much has changed in ...

Technology has enabled more people than ever to support their lives via online side projects. Steph is one of the people who understands this world well, having created multiple six-figure projects over the last few years.

In this episode, Cal interviews Steph about her perspective on bringing an idea to life, managing your psychology, maintaining a reputation, how to price projects, and doing all of this while working a full-time j...

You probably spend more time at home than anywhere else. And how you feel about that time is heavily influenced by the design and functionality of your space.

But how do you create a space that you truly enjoy? Unless you're an interior designer or have the resources to hire one, you may not know where to start and default to keeping things the way they are. That's okay, but what if you could make a few simple, a...

You’ll be hard-pressed to find someone who doesn’t say their health is paramount, yet you'll be just as hard-pressed to find someone who knows what to do to "get there". While every person’s health journey is going to be unique, in this episode Cal and Steph share their experimentation across many of the major categories – from sleep to supplements and beyond. 

Of course, this podcast is for information purposes only ...

Everybody warns you that your body slows down with age, but that deterioration so sneaky, we continue to convince ourselves that we’re doing just fine.

At least, that’s what happened to Steph over the past decade, going from an athlete in her youth to waking up one day without the fitness she once remembered. This episode is a walk through that story, but more importantly, how she got back on track and just ran her first half-marath...

In part 2 of our series in Japan, we dive into the how behind planning a trip there, from what is worth seeing, how to navigate the epic train system, their unintuitive review system, and more.

After traveling to 40+ countries each, we’ve found Japan to be a unique beast, and hope this helps you navigate one of the best countries in the world.

If you missed part 1, start there!

Resources discussed:

• Ful...

We’re back with a whole new season. In our first episode back, we discuss everything from the wonderful to the wacky of Japan.

You'll hear about an epic art island, specialty coffee and konbini (AKA convenience store food), 100+ year-old businesses, the philosophical ideas that make Japan such a distinct place, and much more.

In our next episode, we get tactical and break down exactly how we would plan a futu...

This is the 10th episode back for SYDLIS, so if you want us to continue creating new episodes for the podcast, let us know by leaving a review at ratethispodcast.com/learn. 

In this episode, Steph and Cal bring a medley of half-baked business ideas to the table. They introduce the origin story of each idea, rate it on a scale of A-F, discuss modifications that would make it better, and most importantly, roast each other wh...

There is something out there that can make one person more productive and kind, while another inharmonious -- even resentful. That thing is identity.

And while we passively adopt parts of identity, we often forget that much of our identity is left up to us. In this episode, Cal and Steph explore the depths of identity and how being intentional around what parts of your identity you adopt, shed, or embrace can lead to a mor...

The internet has a treasure trove of information that you can use to generate business ideas, spot trends, and understand what the future will look like before everyone else. But to benefit from the internet's wealth of knowledge, you need to learn how to use it in the right ways.

In this episode, Cal and Steph discuss four unconventional ways that you can use the internet to find good ideas for businesses and product...

Writing is one of the most powerful tools on Earth. But few have mastered the craft.

Perhaps because success in writing often actually veers you off course, leading you to a life of talking instead of living -- the very thing that drove the quality of your writing in the first place.

One man  -- (who has written several novels, thousands of poems, and hundreds of short stories) has some merciless takes on the art ...

Few waves have hit the world quite like remote work; a wave impacting billions of people overnight due to a worldwide pandemic.

But in reality, this wave was brewing for decades and thousands of nomads had long been proving there was a different and viable way to work. Calvin and Steph were two of those people, starting in 2016.

Now that the world has caught up, they decided to reflect back on what was so special ...

Few people inspire us more than Yayoi Kusama.

Cal recently discovered this 94-year old's work while at the Guggenheim in Bilbao. Like many others, he was immediately gripped by her art – enough to be the only artist he looked up after his visit. Little did he know she was one of the world's most successful living artists, had been creating thousands of pieces across nearly a century, and has quite the storied pas...

Many people waddle through life without asking themselves a simple, but important question: What do I want? 

In this episode, Steph and Cal discuss how to figure out what you want and avoid some common traps that take you down unhelpful detours.

The episode is based on two of Cal's recent articles, which you can read here:

• What Do You Want?
• Calvinball: The Only Game Worth Playing

This episode is not aff...

Some people argue for tipping. Some people argue against. But the one thing that unites most people with an opinion on the topic is a lack of understanding of where the practice came from in the first place.

In this episode, Cal and Steph walk through the history of tip culture, how that led to vastly different norms around the world, and the confusing place we're left in today – especially in an era of Square termina...

The Master Somm test is widely recognized as one of, if not the hardest test in the world. Only 273 people have passed it since it was incepted in 1969, also making it one of the rarest distinctions out there (<0.00001% of the world!)

In this episode, Steph and Cal discuss some of the hardest human feats, from athletics to intelligence to, and whether a healthy ambition can lie behind them.

They also discuss wh...