WHEN YOU'RE LOVING

17. On Love, and What to Look For

"We are most alive when we're in love." —John Updike

Dear Kids,

Of everything I've written you so far — luck, risk, the small choices that compound — this is the letter I trust myself on the least, and the one I most needed to write. A disclaimer before anything else: this is a topic in which I'm definitely not an expert — as witnessed by the fact that I've yet to be married, have kids, or do any of the things that would qualify a person to write authoritatively about love. Dating, relationships, and love are enormous subjects, and there are far better resources out there. What follows is me only scratching the surface of what I'm comfortable with, based on my own limited and frequently mistaken experience.

And to all the previous exes who somehow end up reading this: I do sincerely apologize for any past wrongs my actions may have caused. Perhaps I learned many of these lessons too late. I hope you're all well.

I'll still write it down, because I'd rather hand you my honest, unfinished thoughts at thirty than say nothing and let you reinvent every mistake from scratch.

One of the most obnoxious but strangely catchy "trends" that overtook social media a while back was the "looking for a man in finance" video — a girl professing to want a man in finance, with a trust fund, 6'5", blue eyes. As a reaction, a British math professor at UCL calculated the exact number of men in the UK who actually satisfied that criteria. The grand total, wait for it: nine people.

She took some generous assumptions, of course — men aged 20 to 44 (isn't age just a number when your bank account has nine digits?), trust funds that actually pay their taxes (most professionally run, capital-efficient trust funds probably "optimize" their obligations, so her sample may have been the badly run ones), and she didn't even subtract the men who are gay, married, emotionally unavailable, or simply not interested in you. When I think back to my time at Harvard Business School — the supposed bastion of capitalism, where such financial men should grow on trees with bountiful harvests of pre-nuptial agreements and ski chalets in Saint Moritz — the answer was surprisingly similar.

The point is this: dating, and finding a mate, is hard.

Dating is hard — but it still matters more than almost anything

The difficulty isn't a reason to treat it lightly. Quite the opposite. Many studies have shown that finding a life partner is probably the most consequential decision you'll ever make — for your professional success, your personal happiness, and of course, the kids you'll one day have. Think about it plainly: at least half of your children's intelligence, their predilection to addiction, their odds of various traits, will come from your future partner.

Unlike the olden days when dinosaurs roamed the earth, divorce no longer means the end of your life — but the consequences are real. Single-parent households face higher rates of depression among kids, higher chances of trouble, and the added emotional weight of familial complexity. I'm not saying any of this is inevitable. I'm saying the odds matter, and you should know them.

And if you don't trust the statistics, take the anecdotal evidence. Read the reflections of the Harvard class of 1963 — some of the most career-successful people of their generation, looking back after eighty or ninety years on the planet — and you'll find the same refrain: choosing your life partner is among the most important decisions you will ever make. Or, if meaning doesn't move you, here's the blunt version: find a partner and have kids so you're not sad and alone at eighty.

We have less time than we think — so savor the chances

Here is the thing I've come to appreciate most as I've gotten older: the window of opportunity is far shorter than it feels when you're young and convinced you have all the time in the world.

When you actually add up the time you have to date, figure out your own life, get into something serious, get married, and then have kids — the number of real shots on goal is smaller than you'd guess. Assume you start dating around 17 and want kids by 35. Some quick (and roughly autobiographical) math:

17–19: High school sweethearts — "Of course long distance will work." Narrator: It didn't.

19–22: I have no idea what I'm doing in college.

22–28: Three rounds of roughly two years each — emotional problems, relationship trauma, self-discovery.

28–31: "Oh shit, I'm almost 30" — and the serious relationship.

31: Get engaged.

32: Get married.

32–35: Have kids, after two or three years of marriage.

In a good decade, you might have six to eight years to seriously figure out who you are and find the right person out of eight billion. Assuming each relationship runs about two years — including the traumatic breakup and the self-healing afterward — you may get just three or four good shots to find Cinderella.

And it gets harder with age, not easier. The pool of similarly minded, available peers shrinks exponentially as you leave educational institutions — where everyone is roughly in the same life stage — for the working world, where you shouldn't date your colleagues, definitely not your boss, and half of everyone on the apps could, statistically speaking, be a serial killer. So back to the trust-fund, 6'5", blue-eyed finance girl: in reality, how many potential partners are out there who are around your age, emotionally available, not already taken, intellectually capable, your type, and into you?

What I'd tell my younger self

If I could build a time machine, I'd go back and slap my 20-year-old self with this reality: you only get a handful of good chances to make one of the most consequential decisions of your entire life — so use them wisely.

I'd tell him to hold extremely high standards for anyone he spends real time with — even if marriage isn't on the table next year — because you'll share their hobbies, their friends, their habits, and you'll quietly become more like them. I'm a believer in "you are the average of the five people you spend the most time with." Show me your partner and I'll show you your future.

But I'd also tell him to savor the ones who genuinely match — and, when they don't, to have the compassion to let go, so you can both find someone better. One piece of early management advice has stuck with me: if a hire isn't working out, let them go, honestly and kindly, because keeping them caps both their potential and yours. Dating is the same — and it's something I struggled with badly.

Because here's the trap I fell into. As an extremely analytical, action-oriented problem solver, I'd enter relationships with the attitude of "I can fix you" — like a client engagement where I'd promised to add value. This does not work. You cannot be both someone's partner and their psychologist. Your partner has to be able to fix themselves; otherwise you breed an anxious, unhealthy attachment. And it does them a disservice, too. Napoleon Hill wrote, "You are the master of your destiny. You can make your life what you want it to be." Don't rob your partner of the pleasure of actualizing their own dreams.

And above all — don't rush into a relationship, or feel you need one to be whole. The savoring matters more than the hurrying.

So then — what to actually look for?

When I was younger, almost everything I was taught to look for was external: physical appearance, the Harvard degree, what looks good on paper. Only later did I understand why. It traces back to childhood and upbringing — the expectations your family quietly installs in you. My parents prioritized achievement and visible badges of success, and so, inevitably, that's what I came to value — in partners, in friends, and in myself. I "learned" that the person with the Harvard degree must be better than the one who went to community college, and I attached a human being's worth to these metrics.

This isn't to say there's no correlation — someone who strove for the Ivy League may genuinely be hard-working or capable. The danger is being blinded by the external badges at the expense of the intrinsic, moral qualities that actually determine whether a long-term relationship works: character, kindness, compatibility. As Abraham Maslow wrote, "If the only tool you have is a hammer, it is tempting to treat everything as if it were a nail." I wish someone had told me this earlier. It would have saved a great deal of time, heartbreak, and tears. The same is true of physical appearance — it fades. Inner beauty lasts.

I read David Deida's The Way of the Superior Man on a friend's couch in New York one weekend, in the gap between leaving a relationship and understanding why it hadn't worked. The book is uncomfortable in the way good books are — it argues that what people actually respond to in a partner isn't charm or pedigree or even attentiveness, but integrity: the absence of any gap between what someone says and what they do, what they value and how they live. Deida's frame turned the question inward in a way I wasn't ready for. I'd been scanning other people for external markers — schools, jobs, the legible stuff — because that's what I'd been graded on in myself. But you can't recognize integrity in someone else if you haven't built any in yourself. The work of becoming worth choosing is the slow, private alignment of word and action, in yourself, before you ask anyone else to commit to it.

Removing those Crimson-colored glasses, and learning to see a partner as a multidimensional, complex person — some of whose traits you'll prize and some you couldn't care less about — is a process almost everyone has to go through. It's the same work of self-discovery I keep coming back to in these letters: becoming an independent, critical-thinking person whose values are genuinely your own and not merely inherited. It doesn't matter whether your inherited values fixate on achievement, appearance, or self-sacrifice — you have to think through what is truly important to you, form a strong independent opinion about it, and hold to it. There's an HBS class, Authentic Leadership Development, built entirely around this exercise. It's the same question whether you're choosing a partner, building a company culture, or deciding who to hire.

One framework I've come to appreciate comes from a conversation between Simon Sinek and Steven Bartlett. Instead of drowning in a list of 367 requirements and dealbreakers, simplify it to four:

Intellectual compatibility — Does this person inspire you to learn and grow? Do they have a passion that drives them? Do you feel stimulated in conversation, constantly learning?

Emotional compatibility — Does this person show emotional maturity and stability? Can they be there for you through thick and thin? Do they make you better? Are they kind — genuinely, plainly kind?

Sexual/creative compatibility — Do you want to create something with this person — a family, a child, a shared life? Physical attraction lives in here, but this is bigger than attraction.

Circumstances — You could meet someone who fits all three and still find that they live halfway around the world, or are already married. Timing and circumstance are their own quiet, stubborn variable — and the one we'll return to in the next letters.

I'll add one more thing, because a book on my shelf in Beijing keeps elbowing its way into this letter. David Deida's The Way of the Superior Man is a strange, slightly embarrassing read — half useful, half overwrought — but the one line that landed for me, in my late twenties, was that the most attractive thing a person can carry is integrity: no gap between what they say and what they do. Not charm, not performance, not the curated version of themselves that survives a first date. Deida's framing pushed me to ask a question I hadn't been asking, which is what kind of presence am I bringing into a room before I get to the question of what I'm looking for in someone else. The math of attraction stops being a math problem the moment you realize the most decisive variable isn't who walks in the door — it's who you are when they do.

That's the foundation: dating is hard, the clock is shorter than you think, the external badges are a trap, and what actually lasts is character. The harder question — once you've found someone who fits — is how you'll ever know. That's the next letter.

Love,

Dad.