David Brooks and Knowing A Person (and Ourselves)

My friend Sara recently sent me this text:

“I was reading this book last night – How To Know a Person by David Brooks. And I read this part and thought 'Oh! This is Jay.' You do illuminate people in such a genuine, sincere, and rare way."

Of course, I was touched. I had read Brooks’ book and found it compelling, very well-written, and insightful. You should visit your local library and reserve your copy today (though, if you’re like me, you’ll probably want your own copy - you’ll be drawn back to it from time to time). 

Brooks’ Wikipedia bio begins: “David Brooks is a Canadian-born American author and political and cultural commentator.” Why am I not surprised that he is Canadian-born? I often find that some of the brightest and best Americans were born in our northern neighbor! His motivation for sharing the wisdom in How To Know a Person is, in my opinion, to help us navigate the particularly fractured and siloed culture we are living in today and to show us a possible path to unity and healing. Though he’s addressing some of the largest and most overwhelming issues of our time, he writes from a deeply personal perspective. And that’s why it works so well. 

I think Brooks' work is unusually relevant to our advising work and, in particular, what we call the “Second Decision”: the deeper questions and insights that can come after wealth is achieved. He is not really writing about relationships - he's writing about attention. Being seen. 

Philanthropy – and the Second Decision - isn't really about giving. It's about seeing.

Most philanthropy begins with a familiar question:

What problems should I solve?

Brooks would probably argue that's the wrong first question.

The better question is:

Have I learned to truly see the people whose lives I'm hoping to change?

In How to Know a Person, he argues that most of us move through life only partially seeing one another. We categorize. We assume. We jump to solutions before understanding.

Many philanthropists do exactly the same thing.

They fund programs before they understand communities.
They measure outcomes before they've listened to lived experience.
They ask "What can my money accomplish?" before asking "What is already happening here that I haven't noticed?"

The Second Decision isn't merely deciding where to give.

It's deciding how you will learn before you lead.

Wealth often makes it harder to know people.

This feels almost paradoxical.

Brooks points out that status can distort relationships. People begin performing for one another instead of revealing themselves. (Another excellent resource that beautifully illuminates this is Dr. Paul Hokemeyer’s “Fragile Power.”)

A liquidity event often creates exactly this problem.

Suddenly, everyone has advice, everyone has an opportunity, everyone has an opinion, and everyone has their favorite nonprofit. 

Ironically, the more successful someone becomes, the more difficult it can become to know who is genuinely seeing them - and who is seeing their wealth.

The best advisors don’t simply offer technical expertise. They create a space where clients can explore questions of identity, purpose, and uncertainty without immediately being steered toward transactions.

Philanthropy is an act of curiosity before it's an act of generosity.

One of Brooks' recurring themes is that good conversations begin with genuine curiosity rather than expertise.

Many wealthy individuals believe they're expected to arrive with answers.

Experienced philanthropists often discover the opposite.

The most transformative donors become exceptional learners.

Instead of asking, "How can I fix this?"

They begin asking, "What am I missing?"

That question changes everything.

It changes site visits.

It changes board meetings.

It changes relationships with nonprofit leaders.

It even changes evaluation, because the goal becomes understanding rather than simply proving success.

The best philanthropic decisions are often made by people who remain open to being surprised. 

Every philanthropic strategy begins with an identity conversation.

Most wealth planning asks:

What do you own?

Most charitable planning asks:

What do you want to fund?

Brooks asks something much deeper:

Who are you becoming?

That's almost a perfect description of the Second Decision.

The first decision changes a person's financial circumstances.

The Second Decision changes the story they tell about why they have wealth in the first place.

In that sense, philanthropy isn't merely an expression of values.

It's a process through which people discover their values.

That's why the work cannot be reduced to tax optimization or grant recommendations. It's fundamentally about understanding who you are.

David Brooks reminds us that the greatest human gift is making another person feel seen. The Second Decision asks us to extend that same discipline beyond our relationships - to our communities, our philanthropy, and even ourselves. Before wealth changes the world around us, it changes the questions we ask about who we are and what we owe one another.

“How To Know a Person”: By The Numbers

• The General Social Survey asks Americans to rate their happiness levels. Between 1990 and 2018, the share of Americans who put themselves in the lowest happiness category increased by more than 50%. 

• The central conclusion of a Harvard Study of Adult Development, which followed participants for more than 85 years, found that the quality of close relationships is the strongest predictor of long-term happiness, physical health, and even cognitive health - not wealth, IQ, or career success. – The Good Life (2023), Robert Waldinger and Marc Schulz.

• People experiencing chronic loneliness become more likely to interpret neutral interactions as threatening. They become more suspicious, more defensive, and less trusting - not because people around them changed, but because loneliness changes perception. – John T. Cacioppo, Journal of Research in Personality, 2016.