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Shit You Don't Learn in School

Calvin Rosser & Steph Smith

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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.
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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 modific…
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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 arou…
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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…
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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, a…
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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 …
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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 thousand…
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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? Calvinba…
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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 confu…
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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 whet…
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After years of being nomadic, we embarked on an experiment of living in Encinitas. That experiment lasted 3 years, but provided us with a clearer view of what we wanted next. But could we get past the multi-year stand-off around location and find a place that fit both of our needs? Listen in to find out. This episode is not affiliated with Steph's …
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ChatGPT broke records in adoption, hitting 100m monthly active users in a matter of months... faster than any other web platform prior. Even faster than TikTok! But with fast adoption comes equally swift resistance, surfacing questions around how this technology is changing the wider world. Should AI models be allowed in schools? How about the cour…
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One of the most important decisions in life is who you choose to spend your life with, yet it's also one of the hardest things to get right. Inspired by a recent conversation with a friend that may have unrealistic expectations, Cal and Steph discuss the data behind dating, but also their own very different approaches to it... and if they ever ende…
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Have you ever looked around your home and thought, "Where did all this stuff come from?!" Cal and Steph are currently going through this exercise, as they go through their first move in years. It turns out they're not alone in this feeling of overwhelm and is shared by many others who used to be nomads. The need for *things* is universal, but so is…
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Each January, Steph and Cal sit down to reflect on the prior year and this one is no different. You'll find out their... Best New Idea Best New Life Hack Best New Experience Best/Worst Purchase Best/Worst Trend Best Personal Win/Accomplishment #1 Goal for Next Year Prediction for the New Year Jumpstart 2023 by doubling down on the best activities a…
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A few weeks ago, Steph and Cal had a locksmith come in. It cost $185 and was shockingly quick... just 10 minutes! Little did they know it would also be the fodder for one of Steph's most popular tweets of all time. Perhaps it shouldn't be surprising – people love learning about new opportunities. That's why they decided to record this (hopefully) r…
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There has been a wave of recent cheating scandals, from chess to poker to fishing. But cheating is not new, nor is it a rare occurrence. In fact, some articles sport stats like "75 to 98% of college students have cheated" or "over 46% of respondents in a monogamous relationship said they had affairs." In this episode, Cal and Steph discuss when – i…
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For years, people thought that artificial intelligence would wipe out repetitive tasks, but leave the creatives untouched. But recent developments have left many people surprised and taken the creative world by storm. Tools like DALL-E, Midjourney, and Stable Diffusion gave anyone with a keyboard and a wifi connection the ability to spin up images …
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It's human nature to worry about the things that can go wrong. But often overlooked is the mentality of attraction instead of detraction, or in other words focusing on what you can bring to the table instead of what you can prevent from happening. While so many companies signal they want entrepreneurial candidates yet don't allow side projects, wan…
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Money is a leading cause of problems in relationships. It’s not just not having money, it’s conflict around money, lack of alignment, and the downstream effects of that. Money is complicated because it’s influenced by your direct circumstances, but also by your childhood, psychology, and trajectory. It's also complicated because so few people talk …
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In part 2 of this 3-part series, we decided to re-air part of our most popular episode, #35: Does Marriage, Retirement, or the 40-Hour Work Week Still Make Sense? In this segment, we share: How humans are actually not wired for monogamy What animals within the animal kingdom are monogamous The history of marriage and when marriage started to be ass…
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In part 1 of our 3-part series, we're joined be Amanda Natividad and Marissa Goldberg – two friends of the podcast – to discuss the traditions that surround love. After getting engaged last year, Steph found herself in a place she didn't expect and with emotions that she didn't feel entitled to have. That led her down a deep rabbit hole of question…
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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. Next Steps Essay about the nuance of privilege If you liked this episode, make sure to subscribe and leave a review. To receive the latest updates, follow The Sh*t You Don'…
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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 …
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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 t…
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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 exp…
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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 …
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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 word…
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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, m…
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"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 de…
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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,…
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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 test…
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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 doubli…
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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 …
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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 sca…
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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 s…
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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 we…
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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 is…
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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…
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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 i…
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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 ab…
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The big failure of most productivity advice is the focus on efficiency – getting things done more quickly. We should be focused on effectiveness – making sure we're doing the right things. In this episode, Steph and Cal explore how we can rethink productivity to get more out of how we spend our most valuable resource: time. They cover a variety of …
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We're all familiar with how to increase physical security – locking our doors, paying attention to our surroundings, putting valuables in a safe, etc. – but what about our digital security? With an increasingly digital world comes a less perceptible risk – the risk of having your information hacked and exploited by someone with whom you will never …
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At a time where several asset classes are at all-time highs, there's a lot of talk about whether we're in a bubble. That, coupled with crypto assets falling to ~half of their highs, prompted Cal and Steph to dive in to try to answer this question. In this episode, they discuss the markings of past bubbles, the innovation hype cycle, the difficulty …
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Travel is fun, but it becomes even more enjoyable once you know how to do it well. Collectively, Steph and Cal have visited over 70 countries while working remotely, learning a bunch of useful tips for better travel along the way. In this episode, they share some of the most useful learnings, including: - How to avoid getting scammed - How to choos…
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The world is run by incentives, but what happens when those incentives go wrong? In this episode, Calvin and Steph talk through the Cobra Effect, a phenomena incentives designed to improve society actually end in negative consequences, often resulting in actions counter to the original goal. They discuss several examples of the effect and how peopl…
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Drinking alcohol is embedded within the social fabric of society, but how do we take control of our relationship with alcohol? For all of the fun it supports, alcohol is a poison that causes unnecessary physical, mental, and emotional harm for many people. In this episode, Steph and Cal interview Taylor Platt, a Princeton graduate and NBA strategis…
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Whether we'd like to believe it or not, age is a signal that people judge others by. In a professional setting, it can signal your level of experience and for that reason, it can be difficult to earn the trust of a team, if they happen to be older than you. In this episode, Calvin and Steph talk through their experiences managing at a young age and…
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