My 10 Biggest Lessons & Highlights from 2020

High-Level Overview

In this year-end episode, Lewis Howes sits down with Matt Cesaratto, his business partner, friend and former college football teammate who runs The School of Greatness day to day, to look back on 2020. The first half is a behind-the-scenes list of the year's highlights for the show and the business: a cold-exposure trip to Poland with Wim Hof, a new studio, a documentary premiere, the 1,000th episode, big-name guests, conversations about social justice, a fast pivot when the pandemic hit, a new commitment to YouTube, the death of Kobe Bryant, and a doubled team. The second half is Lewis's ten biggest lessons of the year, from health and financial preparation to emotional agility, relationships, mission, compassion, positivity and play.

The tone is warm, casual and brotherly. The two finish each other's sentences, reminisce about splitting a $250 apartment in college, and are open about what they got wrong, such as neglecting YouTube for years and not being great at hiring. It is less an interview than two partners taking stock, and the conversation moves in a simple order: ten highlights first, then ten lessons, each illustrated with stories from their year.

The Discussion Explores:

• The Poland trip with Wim Hof and why it felt like preparation for the year that followed
• Building a studio, premiering a documentary and reaching 1,000 episodes just as the pandemic arrived
• How persistence over years finally landed guests like Kevin Hart and Matthew McConaughey
• The pandemic pivot, the DARES framework for products, and going all in on YouTube
• Why they chose to build an in-house team and hire for culture over skill
• Health and "preparing for winter" as the foundation for surviving a hard year
• Emotional agility, patience and deeper relationships at home
• Mission, mentors, open-mindedness, gratitude and making time to play

Deep Dive into Main Ideas

Poland with Wim Hof: the last trip before everything changed

The first highlight dates to January 5, when Lewis took a group of 13 men to Poland to train with Wim Hof for five days. Both say it now feels like it happened years ago. Lewis calls it probably the most physically challenging experience of his life: they jumped off a cliff of 20 or 30 feet into a frozen river, sat in ice tubs for 10 minutes at a time, did saunas, breathing and meditation, and climbed a mountain on the border of Poland and the Czech Republic for four and a half hours wearing only shorts and gloves.

Matt says what stayed with him was the way the group shared with an open heart and mind. It reminded him of a college football locker room, where you see both the macho side and the vulnerable side. With no Wi-Fi or cell service, they stayed up until two or three in the morning talking in bunk beds and playing music. Lewis says he does not know whether anything could have prepared them for 2020, but that the trip was great grounding, and it was the last trip most of the group took that year.

A studio, a documentary and the 1,000th episode

After running the podcast from his home for six and a half to seven years, Lewis decided at the end of the previous year to build a proper studio and office and grow a team around it. They recorded the first episode there in February. Matt, who has a three-year-old daughter at home, calls the space a saving grace, since the rest of the team was sent home and it was mostly just the two of them there. About half the year's guests still came in person, with testing. Lewis says he liked finally having a place to go and a home to return to, especially since his girlfriend moved in with him this year.

In February they also premiered a documentary they had worked on for a couple of years, selling out a screening at the Grove in Los Angeles, followed by a Q&A that Matt remembers for the vulnerability in the room. Lewis says they were among the last films shown there before theaters shut. Talks about placing it on a larger platform stalled when the pandemic hit, and they are still weighing whether to release it on their own YouTube channel.

The show also reached its 1,000th episode, seven years after launching in 2013, and passed 305 million downloads and views of its long-form audio and video. Lewis reflects that they were once 21 and 22 year old roommates paying $125 each a month, playing college football and dreaming big, and that it is striking to see where that led 15 years later.

Guests, persistence and uncomfortable conversations

Lewis names Kevin Hart, Matthew McConaughey and Rhonda Byrne among the year's notable guests. He says he had emailed Kevin Hart's publicist every couple of months for about five years and always heard no, until Hart had a self-help book coming out and the timing fit. His takeaway is that when someone turns you down, you keep following up and keep building your platform, and eventually you attract the people you wanted from the beginning. Matt points out that the rejections never derailed Lewis's consistency. Lewis adds that Rhonda Byrne's interview drew more than half a million views in under two weeks and, as he understood it, was her first interview in about 12 years.

Another highlight was the show's response to the social justice movement. Lewis says they actively invited guests to help their community understand how to be of service, beginning with Michael Beckwith, who spoke from a spiritual grounding, and then Laverne Cox, whose episode Matt calls a team favorite, and Emmanuel Acho. Lewis describes the team as constantly evolving in how it could contribute.

The pandemic pivot, DARES and YouTube

When the pandemic hit, Lewis says there was about a week when he and Matt asked what to do: whether they could pay people, and whether anyone would keep buying their products. They decided not to retreat or merely maintain. Although much of their material is paid, they put on a free webinar teaching people to earn money from side hustles using skills they already have, which Lewis says drew about 25,000 registrations. He notes that the brand had spent a decade teaching people to work from home, so it became a resource when the world suddenly needed that.

Lewis credits their friend and consultant Rory Vaden with a framework they had been moving toward for a couple of years: every business should be creating DARES, products and services that are "digital, automated, reoccurring, evergreen, and scalable". They shifted everything in that direction this year. Lewis also repeats a line he saw recently, "if you maintain, you're dying", and Matt ties it back to their football days: stay in the fight and in the game.

YouTube is the other big shift. They had filmed episodes for about five years, before most podcasts recorded video, but simply uploaded them and never turned on ads. Lewis says the YouTube expert Evan Carmichael had urged him for roughly three years to take the platform seriously, and that his girlfriend, Jeanette, asked why he was not monetizing it and showed him her own channel. They went all in, optimizing 800 or 900 existing videos much as one would rework old articles for search. They say subscriptions and views tripled from 2019, with most of the results arriving in the last four months, and that many new listeners now say they found the show on YouTube.

Kobe Bryant, and betting on a team

Lewis calls Kobe Bryant's death a notable moment more than a highlight. He remembers watching the news with his girlfriend and thinking it had to be a bad dream. He only spent about an hour with Bryant, but recalls arriving at his office around 6:30 a.m. to learn that Bryant had already been there alone for an hour or more preparing for his day, long after he had achieved everything. The re-released interview, with Lewis's lessons from Kobe, was the show's most downloaded audio episode of the year.

The final highlight is that they doubled the team. For years they had debated staying lean with contractors and agencies versus building an in-house team committed to the mission. An event run by Darren Hardy, where business leaders agreed that the only real way to scale is to build a team, helped settle it. Lewis admits they are not the best at hiring and that people have come and gone, and that it costs time and money, but says it frees each person, including him, to focus on their particular strengths. They also partnered with the podcast network Wondery. Both stress that "culture is key": skills can be trained, but attitude, effort and a growth mindset cannot be skipped, because one lazy or closed-minded person affects everyone around them. Matt says team members that very morning had described the environment as safe and family-like.

Lessons 1 to 3: health, preparing for winter, adapting

Lesson one is that health matters most. Lewis points to how many people were physically, mentally and emotionally unwell this year, and says the richest person in the world would give it all up to be healthy. He names four basics he believes anyone can control: sleep, which he calls "the foundation of good health", drinking lots of water, eating healthy food, and movement, which he says is scientifically proven to produce dopamine and make you feel happier. Matt extends it to mental health and describes a woman at his church whose attitude remains strong and giving while she goes through cancer. Lewis says a negative mindset will not make an illness better and that how you respond is a daily choice, while acknowledging it is not easy. They credit holding each other accountable through physical challenges, and agree that "health should never be a New Year's resolution. It should always be an everyday resolution."

Lesson two comes from a small mastermind in Fiji the previous year with Tony Robbins and Dean Graziosi, where Robbins kept repeating that "winter is coming". Lewis takes that to mean taking inventory and decluttering your space, finances, relationships and health habits. He notes many people do not know how much money they have or where it goes. Because the business had cash and was not living month to month, it could cover its team and expenses for the following months. He says this without judgment of people who relied on stimulus checks, adding that he would not have been ready ten years ago, but argues that something will always happen eventually, whether a housing crisis, a pandemic or a market crash. "Hope for the best and prepare for the worst."

Lesson three is to adapt and be flexible. Nearly everything they had mapped out for 2020 disappeared, and they watched friends who earn their living as speakers lose every booking. Matt recalls Lewis reaching out to his network to trade information about what others were doing. They had just invested in an office and hired someone, only to send everyone home a week later, which made building an in-person culture hard. Lewis says he had to be flexible in his personal relationship as well.

Lessons 4 and 5: emotional agility and deeper relationships

Lesson four draws on past guest Susan David and her book Emotional Agility. Lewis says that if everyone had this skill we would all be better human beings, because reacting, getting offended and getting defensive hurt relationships and personal growth. He admits patience has never come naturally to him. Matt tells him, "I've seen you more patient this year than I've ever seen you in the 15 plus years I've known you." Lewis says he got there by asking mentors, therapists and coaches why things were triggering him. He recalls asking Holocaust survivor Edith Eger how to stay patient with someone whose frustration seems irrational; he does not remember her exact words, but the gist was to smile and know that it will pass.

The friends admit they used to back each other in any fight without asking who was right, and say they now try to help each other respond more wisely. Lewis says holding on to anger and resentment mainly hurts you. He is careful to add that agility does not mean suppressing emotions after a loss; it means processing them without letting them overwhelm you indefinitely.

Lesson five is to deepen personal and intimate relationships. Lewis links the year's loneliness and breakups to a lack of intimacy, communication and boundaries. He says he and his girlfriend had ups and downs after she moved in and had to decide whether to go all in, and that learning to listen instead of fight was a key. Matt says his wife recently reminded him of a talk by Ed Mylett about not bringing his phone into the house after work. Matt checks his weekly screen time and does not want his three-year-old daughter to remember him face down in a phone. The people you share a house with, he says, come first.

Lessons 6 to 8: mission, advisors and an open mind

Lesson six is to be led by a mission that inspires you to pursue your vision. Lewis says his mission is what gets him up in the morning, and shares the company's: to inspire humanity to live greater, love deeper and leave a legacy, with a vision of being the number one place to seek inspiration and positively affecting 100 million lives weekly. He notes they have had that mission for eight years without completing it, which is why monthly, quarterly and yearly micro goals matter, and suggests writing down a handful of core values. Matt offers a saying, "be on a mission. Don't be a missionary." By this he means not living your life entirely for someone else's agenda, and being able to say no to what pulls you off course.

Lesson seven is to build a team of mentors and a personal advisory board, something Lewis says he began almost 13 years ago, when he left football and reached out to people through LinkedIn before he even had a company. "You can't do everything alone." You still make your own decisions, he says, but it helps to learn from people who have been there.

Lesson eight is to keep an open mind and be compassionate. Matt says he has tried to keep the show out of politics, but that after a heated election, divisiveness is not creating progress and leading with compassion is. Lewis says they deliberately host people of different backgrounds and philosophies and sometimes get criticism when a guest holds one belief a listener dislikes. He cites Tim Ballard's episode, which he says passed a million views within days, as having opened his eyes to how widespread sex trafficking is, including in the United States. Matt admits that as the father of a young daughter he had avoided thinking about the subject until that episode.

Lessons 9 and 10: be positive and play

Lesson nine is to be positive. Lewis argues that negativity during uncertainty does not help, and that people make better decisions from love than from fear, anger and stress. He is clear this is not about fake cheerfulness: grieve, be angry, be sad, and then lean back into your mission. Matt describes the language shift they use with the team: "You don't have to do it. You get to do it." And beyond that, you are blessed to do it. Lewis's question for a day when everything went wrong is what he would be grateful for if he were forced to find something. Their team has opened Monday calls by sharing gratitude for years, which is why they call it a practice.

Lesson ten is to incorporate play. Amid hiring, launches, family concerns and media overload, the pair would stop for 10 minutes and ride a scooter around the office, inventing obstacle courses. Lewis jokes that it was the year of the scooter. Matt says Lewis has been pulling him away from his desk to go do something fun for 16 years, and recalls the Instagram dance parties Lewis hosted early in the pandemic. Lewis says, "life without play is not a meaningful life", and points to how Matt's daughter creates joy from a string or a ball. Even dull tasks, he suggests, can become a game with music or a timer. They close by returning to Edith Eger, who Lewis says found compassion for her guards in a concentration camp, a level he says he is not sure he has reached.

Conclusion

The episode is a candid year-end review from two friends who built a media business together and had most of their plans erased within weeks. Their highlights show a pattern: the things that carried them through, such as cash reserves, a studio, a long content archive and a habit of persistence, were built before they were needed. Their ten lessons follow from that. Protect your health daily, prepare for hard seasons before they come, adapt quickly, work on your emotional reactions, invest in the people closest to you, stay anchored to a mission, lean on mentors and a team, listen to people who differ from you, practice gratitude, and make room for play. It is practical, personal and encouraging, with plenty of behind-the-scenes detail for regular listeners of the show.

This is a summary of "My 10 Biggest Lessons & Highlights from 2020" from The School of Greatness, giving you the GIST so you can decide if you want the REST. Listen to the full episode.