Shit You Don't Learn in School

Shit You Don't Learn in School

Formal schooling does a terrible job of preparing you to thrive as an adult. The Shit You Don't Learn in School podcast exists to make up for this societal failure. In this show, Calvin Rosser and Steph Smith share stories, insights, and resources designed to help you improve the quality of your personal and professional life. If all works out, you'll be at least 1% better at navigating the waters.


May 15, 2022 64 min

In this special episode, Cal and Steph answer audience questions across a wide range of topics including writing, relationships, finances, and even death. Listen in to find out.

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  • Essay about the nuance of privilege
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    Steph has some exciting news to share in today's episode! Listen in to find out.

    In this episode, Cal and Steph also cover the rise of the creator economy -- both its promise and pitfalls.

    They breakdown why the heightened attention toward creators, whether we can expect a creator "middle class" anytime soon, the importance of IP, and even explore what it truly means to be a "creator"...

    Is it the things they build...

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    We all know that where you live is one of the most important decisions you can make, but it may be more important than you think. And with more people working remotely, there is no more freedom than ever in deciding where you call "home."

    In this episode, Steph and Cal discuss how to think about where you should live, why it matters more than you think, and how you can make a decision when it involves two people who have dif...

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    March 28, 2022 53 min

    Life feels like a bunch of micro-decisions, yet a few macro-decisions often end up determining how you spend most of your time.

    Perhaps one of the most significant are the degree you choose and the first job you take. The decisions that follow those are inevitably pulled by their inertia.

    In this episode, Cal and Steph discuss the importance of exploring the diversity of jobs out there and how many people become fixed in a singular p...

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    We believe that the desire to give is universal, but is just as much a skill as anything else in life. In this episode, Cal and Steph discuss the how you can make a difference during your limited time on this earth, with the limited resources you have -- especially during times like these.

    They dive into...

  • Creative ways that people have supported Ukraine
  • Striking a balance between hedonism and altruism
  • Making difficult problems tracta...
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    February 19, 2022 64 min

    Language is one of the most powerful tools that humans have accessible to them.

    Don't believe us? Consider the fact that someone could walk up to you and say something that could immediately change your mental state.

    Nothing around you has changed, other than the words echoed through the air.

    In this episode, Cal and Steph discuss the power of words and how language can shape the way we think. They use untranslatable words to conv...

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    February 11, 2022 55 min

    The allure of getting rich quick is intoxicating.

    It's even more intoxicating when you're trapped inside and it seems like all your friends have cashed in big.

    In this episode, Cal and Steph discuss Cal's experience with active investing over the last 20 months and ultimately, why it's time to walk away from the casino.

    If you liked this episode, make sure to subscribe and leave a review. You can also read Calvin's...

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    February 5, 2022 60 min

    "The only constant is change", they say.

    In this episode, Cal and Steph discuss just how drastically the world has changed and will continue to change.

    From the iPhone... to the Internet... to antibiotics... to human flight... to to the sequencing of DNA... to perhaps the most important fact that humans now live more than double as long... these developments all happened within the last 100 years.

    Given that things within a si...

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    There's an endless sea of advice online.

    Whether it's from a vague Twitter thread or a clickbait blog post, the advice sounds catchy, but if we're honest... often holds little water.

    However, we all know from experience that the right lessons, sometimes even sitting in plain sight, can genuinely change the trajectory of one's life.

    In this episode, Cal and Steph discuss the few pieces of advice that they think matter m...

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    In this episode, Cal and Steph discuss the hidden side of risk: the infrequent, often unpredictable events that make the biggest differences in our lives.

    If you look around, rare, high-impact events are everywhere. 

  • A small number of days in the stock market drive the bulk of the returns.
  • Large businesses like Google, Amazon, and Best Buy have tested thousands of products, yet have a single profit puppy. 
  • Insurance companies make mone...
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    January 8, 2022 60 min

    In this episode, Steph and Cal break down the best of 2021. You'll find out the...

  • Best New Idea
  • Best New Skill
  • Best New Life Hack
  • Best New Experience
  • Best/Worst Purchase
  • Best/Worst Investment
  • Best/Worst Trend
  • Best Podcast
  • Creator of the Year
  • Best Personal Win/Accomplishment
  • #1 Goal for Next Year
  • Prediction for the New Year
  • Jumpstart 2022 by doubling down on the best activities and avoiding the worst. It's going to be an awesome year.


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    December 28, 2021 50 min

    What do airplanes, railroads, and jazz music have in common? They were all innovations that people feared.

    In fact, if you look into any key technology shift from the past, you'll find a wealth of fear, uncertainty, and doubt surrounding it. And while this shouldn't be surprising, we can still learn from the skeptics of the past.

    We can learn just how difficult it is to predict what's to come and look toward our future wi...

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    Death is universal part of the human experience. During our lives, we often must confront the painful reality of death around us, and eventually, we face that reality ourselves.

    What's odd is that despite death being at the core of the human experience, many people avoid talking or thinking about it. So when people pass away or we face a health scare that brings us into contact with the fragility of life, we often don't know...

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    In the second part of this series on the future of work, Steph and Cal dive into new products and services, alongside macro trends that they predict are in full flux.

    These include mass migration, global tax infrastructure, opportunities for services to specialize, increased isolation, UBI, and of course... the metaverse. :)

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    People say that COVID was an accelerator, forcing trends that may have taken decades to develop, to instead take hold in much less time. Remote work was one of those trends. But we're not done yet!

    The future of work is constantly evolving and it doesn't just impact whether you can Zoom without pants. :)

    In this episode, Cal and Steph discuss the second and third order effects of the remote revolution and what's to come. ...

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    October 14, 2021 35 min

    The information age gives us access to so much advice that it can be hard to see through the noise.

    4AM morning routines that don't make sense for you. Productivity hacks that hardly move the needle. Hindsight bias cloaked as success stories.

    Most advice is well-intentioned, but rarely translates to improvements in another person's life. So this week, Cal and Steph took a step back to ask the simple question: what are the 80/...

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    With the exception of a few companies like Buffer and GitLab, 99.99%+ of companies opt to keep their salaries closed. This closed nature creates information asymmetry and at times, inequity in the workplace.

    Lack of transparency gives companies a hall pass to not develop a robust compensation system, but at the same time, sharing salaries openly isn't without its pitfalls, including privacy and the tendency for people to ove...

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    September 19, 2021 66 min

    Wealth inequality has been increasing for decades, and recently, there has been a heightened focus on billionaires as we debate what to do about the concentration of large swaths of wealth in a few hands.

    In this episode, Steph and Cal discuss whether or not billionaires should exist, common proposals for dealing with billionaires, and a few policy proposals for how we can start thinking about tackling wealth inequality.

    Whether you...

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    September 12, 2021 41 min

    In this episode, Cal and Steph discuss the subjective nature of pricing. They explore how a value extends beyond utility or the physical nature of an asset (think luxury items, NFTs, etc) and use these ideas to explore new pricing models, including tiered, retention-based, and completion-based pricing.

    They also explore how our own psychology can inhibit use as consumers to spend on what's most meaningful and the importance of u...

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    In this episode, Steph and Cal dive deep into traditions, the societal defaults that shape how we think and act in the world. They start by exploring the origins of the 40-hour work week, modern alternatives, and how we can rethink the idea of retirement. In the second half of the episode, they explore how the ways in which commonly held beliefs about monogamy, love, and marriage may not set people up for the life they want to live...

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