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1.

One Thousand Years of Wisdom

What Advice Would You Give to Your Younger Self?

In late 2022, I asked this question to a dozen eighty- and ninety-year-olds as part of my annual birthday ritual. Every year, I conduct a new and (hopefully) interesting exercise that will push me to think and grow. In past years, I had written gratitude letters to all my family and friends, gone on a twelve-hour silent walk, and attempted my version of a misogi challenge (a Japanese ritual that involves doing something so challenging on one day that it has lasting benefits for the rest of the year).

But 2022 felt different.

The birth of my son in May had altered my relationship with the most fundamental reality: time. Observing the passage of time—both in his daily changes and in the juxtaposition of the newness of his life with the suddenly apparent maturity of my parents’ lives—had left me wrestling with its very nature.

I decided to explore the wisdom that time has to offer by talking with those who had experienced much more of it. My younger, naïve self had sought advice from the richest people he knew when charting his life course. My older, (slightly) more enlightened self would seek advice from the wisest people he knew to do the same. I wondered how older people would reflect on what they had learned. What did they regret? Where had they been led astray? What had brought them lasting joy and fulfillment? What detours had proven to be better than the original route? What had they known for sure that just wasn’t so?

What did they know at ninety that they wished they’d known at thirty?

I had these conversations with a diverse and fascinating group. A video call with my ninety-four-year-old grandmother in India, born a princess of a small kingdom prior to her family being run out by the British colonists, yielded this beautiful insight: “Never fear sadness, as it tends to sit right next to love.” An email from a ninety-eight-year-old family friend who had spent his career as a Hollywood writer yielded a personal favorite: “Never raise your voice, except at a ball game.” His eighty-eight-year-old wife, a former soap opera star whom he had met on set and fallen desperately in love with, added, “Find dear friends and celebrate them, for the richness of being human is in feeling loved and loving back.” In a text message, the eighty-year-old father of a close friend expressed regret over his body’s deterioration over the years: “Treat your body like a house you have to live in for another seventy years.” He added, “If something has a minor issue, repair it. Minor issues become major issues over time. This applies equally to love, friendships, health, and home.” A ninety-two-year-old who had recently lost his beloved wife of seventy years said something that brought tears to both of our eyes, his poetic ode to their evening practice: “Tell your partner you love them every night before falling asleep; someday you’ll find the other side of the bed empty and you’ll wish you could tell them.” My last conversation was with the ninety-four-year-old great-aunt of one of my dearest friends, and she delivered this beautiful closing insight: “When in doubt, love. The world can always use more love.”

The responses ranged from playful and witty (“Dance at weddings until your feet are sore”) to deeply moving (“Never let a good friendship atrophy”). Some were common tropes repeated over the years (“Always remind yourself that your track record for making it through your bad days is perfect”); others were original and thought-provoking (“Regret from inaction is always more painful than regret from action”). The wisdom I gathered was the product of 1,042 years of lived experience.

I hadn’t steered the dialogue in any way—I had simply posed the question and let each of them take it as they wished. They had independently focused on a variety of things: build lasting relationships, have fun, invest in your future mental and physical wellness, raise well-adjusted kids, and more. There was certainly immense value in what I heard but perhaps even more value in what I didn’t. In all the advice, insight, and wisdom shared, there was a notable omission.

No one mentioned money.

There’s Always Going to Be a Bigger Boat

Before we go any further, I want to make an important point: This book will not argue that money doesn’t matter, that you should give up your worldly possessions, go live as a monk in the Himalayas, and spend sixteen hours a day meditating in silence. If you want to do that, great, but I won’t be joining you!

Money isn’t nothing—it simply can’t be the only thing.

Three core insights summarize the body of research on the topic of money and happiness:

1. Money improves overall happiness at lower levels of income by reducing fundamental burdens and stress. At these lower levels, money can buy happiness.

2. If you have an income above these levels and are unhappy, more money is unlikely to change that.

3. If you have an income above this baseline and are happy, more money is unlikely to drive increasing happiness.

The second and third insights point to the same critical conclusion: Once you’ve achieved a baseline level of financial well-being, more money is unlikely to meaningfully affect your overall happiness. In other words, the default scoreboard—focused on money—may be a useful asset in the earliest days of your journey, but it is a liability when you’re attached to it in the later days. Arthur Brooks, a bestselling author, a professor at Harvard Business School, and a leading authority on happiness science, agrees. “When it comes to money and happiness, there is a glitch in our psychological code.” He argues that this glitch is driven by our flawed extrapolation of the early-in-life happiness gains from increases in income—that we experience some of the positive impact of money on our well-being as children and young adults and then spend the rest of our lives, “[salivating] in anticipation of good feelings when the bell of money rings.”

The glitch keeps us on a metaphorical treadmill, always running, never getting anywhere, chasing the early-in-life happiness that money once provided.

In a 2018 paper published by Harvard Business School professor Michael Norton, researchers asked a group of millionaires (1) how happy they were on a scale of 1 to 10 and (2) how much more money they would need to get to a 10 on the happiness scale. Commenting on the results, Norton said, “All the way up the income-wealth spectrum basically everyone says [they’d need] two to three times as much.”

I decided to test this notion by asking a group of financially successful people I knew to answer those same two questions. The responses were surprisingly consistent: A technology app founder worth thirty million dollars said he would need two times more to be perfectly happy; a software entrepreneur worth one hundred million said he would need five times more; a venture investor worth three million said she would need three times more. With the exception of one enlightened investor worth twenty-five million who replied, “Honestly, I’m happy where I am” (although he added, “But if I had twice as much, I could probably fly private a lot more, which would be nice”), everyone up and down the net-worth spectrum said that two to five times more money was all they needed to reach the land of perfect happiness.

I’ll never forget a conversation I had with a friend who had recently sold his manufacturing company and made one hundred million dollars. I asked if he was happier now than he’d been, given that he was richer than most people could imagine, expecting him to say, Of course! His response surprised me. He told me that after he closed the deal, he had taken a group of friends and family for a weeklong trip on a rented yacht to celebrate. He was excited for the moment when everyone would board the beautiful vessel, which he had paid for with his hard-earned sale proceeds. But when everyone arrived, something peculiar happened. One of his friends looked over to the next mooring where an even bigger and more luxurious yacht was docked and commented, “Whoa, I wonder who’s in that one!” The happiness and satisfaction that my friend had felt around the moment quickly deflated at the comparison.

There’s always going to be a bigger boat.

Through the notable omission of money by the wise elders, the scientific research on money and happiness, and the anecdotal accounts from financially successful people, we can derive the most important lesson, the one that sits at the heart of this book:

Your wealthy life may be enabled by money, but in the end, it will be defined by everything else.