If you're being honest, how would you say you live your life? Are you alert and aware or are you sleepwalking through the days?

When we're not aware, we adopt a passive, herd-like mentality that blinds us to what actually matters in life. We mistakenly think we have time when we don't. We think we're working on something important until we realize "that something important" is petty short-term bullshit.

I've been thinking about this ever since I wrote this week's Dossier on Mark Bertolini, the former CEO of Aetna.

In his early career, Bertolini was competitive, aggressive, and at times, ruthless. He was so well known for his bare-knuckled, iron-fist leadership that his employees had given him the moniker, "Darth Vader."

"I was tough," he says. "People used to hum the Darth Vader tune when I walked around the office. It was like, ‘Here he comes.'”

By all measures, he had made it. He was making tons of money, living in a mansion, and earning respect in his field. But it came at a cost. He was spending more and more time away from his family, and inadvertently creating a work culture that didn't necessarily reflect his values.

Then came a wake-up call.

In 2001, his son Eric was diagnosed with a rare and deadly form of lymphoma. Bertolini left his job as an executive at insurer Cigna to care for his son and donated one of his kidneys to him in 2007. Today, his son is the only known survivor of the disease.

"All of a sudden my son got sick and my money didn't matter, my position didn't matter," Bertolini says, adding that he realized that "who you spend your time with and how you spend it every day are the two most important decisions you will make."

I'm reading a great book right now called, How to Live: A Life of Montaigne, and it chronicles the life of French philosopher Michel de Montaigne. In it, he says that most people get so entrenched in their daily habits — no matter how harmful — that they fall into a world of complacent misery.

He writes:

“For in truth, habit is a violent and treacherous schoolmistress. She establishes in us, little by little, stealthily, the foothold of her authority; but having by this mild and humble beginning settled and planted it with the help of time, she soon uncovers to us a furious and tyrannical face against which we no longer have the liberty of even raising our eyes.”

Look up and look around. Are you spending your days doing something interesting with people you enjoy? Or are you simply passing the time busy getting outraged at the scandal du jour?

I'll leave you with the words of Paul Graham on the impossible fragility of life:

"If life is short, we should expect its shortness to take us by surprise. And that is just what tends to happen. You take things for granted, and then they're gone. You think you can always write that book, or climb that mountain, or whatever, and then you realize the window has closed. The saddest windows close when other people die. Their lives are short too. After my mother died, I wished I'd spent more time with her. I lived as if she'd always be there. And in her typical quiet way she encouraged that illusion. But an illusion it was. I think a lot of people make the same mistake I did."

Remember, time is an illusion. Wake-up calls are simply reminders of values we've always held but have been ignoring. They typically come in the form of something unpleasant — an unexpected death, a breakup, a sickness, or some sort of loss.

Forget status, forget money, forget the shiny stuff that doesn't actually matter. Who do you spend your time with, and how? It's that simple and that complicated.

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I would actually love to hear from you on this one. Have you had a wake-up call that shook you to your core and fundamentally changed the way you approach life? If you feel comfortable, please reply to this email with your story, and I'll compile the responses (anonymously) in a future edition of The Profile.

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THE PROFILE DOSSIER: On Wednesday, premium subscribers received The Profile Dossier, a comprehensive deep-dive on a prominent individual. It featured Mark Bertolini, the radical capitalist. Become a premium member, and read it below.

The Profile

The Profile Dossier: Mark Bertolini, the Radical Capitalist

Mark Bertolini doesn't match the image you have of a buttoned-up, clean-cut Fortune 500 CEO. Known for sporting tattoos, leather jackets, and a large skull ring, former Aetna chief Mark Bertolini is a self-described "radical capitalist." Radical capitalism refers to the actions he took in the workplace before it was cool to do so. He raised the minimum wa……

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4 days ago · 7 likes · Polina Pompliano

PROFILES.

— The bitcoin proponent provoking the government [**HIGHLY RECOMMEND**]
— Wall Street's most influential investor
— The first tennis billionaire
— The 85-year-old billionaire who wants to legalize weed
— The actor re-writing his story
— The teenage Honey Boo Boo
— Florida's python hunters
— The boxer-turned-politician

PEOPLE TO KNOW.

The bitcoin proponent provoking the government: Yes, this is yet another profile of Ian Freeman, the host of Free Talk Live, a libertarian talk radio show syndicated to 185 radio stations across the country. Although he was one of the first Americans to popularize bitcoin, Freeman has been promoting cryptocurrency less for the money and more for the libertarian ideals he believes it represents. Those very values were put to the test when the Feds went after him. (New York Magazine)

“For the first time in generations, if not most of human history, the individual can finally have control over money."

Wall Street's most influential investor: On paper, Cathie Wood seems an odd standard-bearer for young, diverse, and deeply irreverent ranks of retail investors. But Wood and her firm’s unusual approach to investing — which combines high levels of risk with high levels of transparency about her views to produce astronomically high returns — have connected with new investors in a way the financial industry had only dreamed of. Through her firm, Ark Invest, Wood manages nearly $85 billion — up from less than $10 billion at the end of 2019. (WSJ)

“The difference between her and a lot of these other folks is she legitimately believes in these things, and she doubles down."

The first tennis billionaire: Tennis star Roger Federer is one of the few athletes in history to earn $1 billion during his playing career. His two decades of on-court achievements only begin to account for that stunning total: About $130 million of Federer’s earnings has come from official prize money. The rest has come through sponsorships, endorsements, appearance fees at tournaments, and lucrative exhibition events around the world. One thing is for certain — no tennis superstar has ever built a financial empire comparable to Federer's. Here's why Roger Federer is the greatest player-mogul the tennis world may ever see. (The New York Times)

“Roger is going to have a legacy and a business that is going to live on well past his playing days."

The 85-year-old billionaire who wants to legalize weed: Depending on whom you ask, Charles Koch is a titan of industry, dark money political bogeyman, or the Marcus Aurelius of the libertarian movement. But soon Koch might be known as the billionaire who persuaded Republican and Democratic holdouts to legalize cannabis at the federal level. Here's why Koch is putting his name, and nearly $25 million of his $45 billion fortune, to influence criminal-justice reform and legalization by the end of 2021. (Forbes)

“It should be the individual’s choice. Prohibition is counterproductive. It ruins people’s lives, creates conflict in society, and is anti-progress. The whole thing never made sense to me."

The actor re-writing his story: It's hard to describe this profile of actor Owen Wilson because it's all over the place in a good way. He eats warm pancakes made with squash. He loves hydration therapy and movie fight scenes and something called "magical realism." He's thriving. But Wilson is human after all, and he got to this place after battling depression and attempting to take his own life. He recovered and now cherishes the love that friends and family had for him and his well-being. This is an amazing profile. (Esquire)

"Once you’re an adult, you think childhood was so innocent and beautiful, but you forget."

The teenage Honey Boo Boo: Remember Honey Boo Boo, the rambunctious child beauty queen? Well, she's now 16 years old, and she'd prefer it if you used her real name: Alana Thompson. Thompson is attending high school, saving to buy her first car, aspiring to become a neonatal nurse, and trying to get straight A's. Here's how Thompson is trying to shatter the stereotypes of her child star days and transition into a young adult forming her own identity. (Teen Vogue)

“I guess people still expect me to be little Honey Boo Boo, and I'm not anymore."

Florida's python hunters: In the last decade, pythons in South Florida have eaten practically everything else in the area, including rabbits, foxes, and raccoons. In response, the state started two python elimination programs. In 2017, it hired 25 people apiece and paid them minimum wage to prowl for snakes. The programs have helped to remove thousands of snakes, but now, Governor Ron DeSantis has doubled down and put twice the ­number of contractors on the state payroll and has gotten experimental. Meet the hunters trying to fix Florida's python invasion. (Field & Stream)

“We got the reputation for being arrogant, but we’re probably the top-producing contractors in the program."

The boxer-turned-politician: Manny Pacquiao recently emerged from a two-year boxing hiatus to fight Yordenis Ugas. He suffered a blistering defeat, which marked what could be his final fight as he has increasingly turned his attention to politics. As this profile notes, Pacquiao's life has been a series of small miracles: "Abject poverty led to unfathomable success which led to self-destruction which led to repentance and a remarkable second act." Here's who Pacquiao is outside the ring. (ESPN)

"This is the toughest fight of Manny's life."

✨ This installment of The Profile is free for everyone. If you would like to get full access to all of the recommendations, including today’s audio and video sections, sign up below.

AUDIO TO HEAR.

Cathie Wood on why innovation thrives in crisis: Cathie Wood has undergone a total of 10 financial crises in her investing career — two of which were complete shocks to the system. “Innovation gains market share at an accelerated rate in a crisis,” she says. Wood is already in the pantheon of top money handlers over any period in the past five years, and has been the most persuasive — and so far prescient — champion of Tesla. Her actively managed Ark Innovation ETF is the best performer among 584 funds with at least $1 billion of assets in the global equity market. This is a fascinating conversation. (Link available to premium members.)

Franklin Chang Díaz on developing a passion for space: Astronaut-turned-entrepreneur Franklin Chang Díaz credits his youth and imagination for helping develop his passion for space exploration. "At that young age, our minds were not contaminated with fears and uncertainties, and that's when people tend to be bold and exploratory," he says. In this podcast, he explains how parents should encourage young kids to take well-calculated risks. "Failure is really a requirement for success," he adds. (Link available to premium members.)

Jimmy Wales on the power of design: Wikipedia founder Jimmy Wales has an analogy he calls, The Steak Knives Analogy. It goes like this: Imagine you're designing a restaurant and you think, "I'm going to serve steak in my restaurant because I like steak, and I'm going to give everyone steak knives. And one thing we know about people with knives is they might stab each other. So therefore, I’m going to build a cage around every table so that no one can stab each other." That would never work. Here's what Wales learned about the design of social networks and how that informed his belief that it's better to design for the benefit of nice people rather than for the deterrence of bad people. (Link available to premium members.)

VIDEOS TO SEE.

Shane Parrish on using mental models in everyday life: The best way to make intelligent decisions? Use mental models like Hanlon’s Razor, first principles thinking, and inversion. These different frameworks help us simplify complex situations and make better choices. In this conversation, Shane Parrish explains that the quality of our decision-making is of utmost importance in times of chaos. “You can often break big decisions into smaller decisions and gather information that could change the path,” he says. (Link available to premium members.)

Tory Burch on building a fashion powerhouse: Fashion designer Tory Burch climbed the corporate ladder before she set out on the entrepreneurial path. She saw an opportunity in the “accessible luxury” space, but she didn’t have design experience nor did she have a business background. “I was putting myself out there, and my parents said, ‘Thicken your skin, and think of the negativity as noise,’” she says. In this interview, Burch talks about what she’s learned about power and leadership over the years. (Link available to premium members.)