Tom Haslett spent years in the investment management industry, climbing the ladder, doing everything right. Then one day he looked around at the people in positions above him and realized something uncomfortable. There was nobody there he actually wanted to become. That realization changed a lot. Today, Tom spends his time thinking about questions most people avoid. What is money actually for? How did accumulation become the same as worth? What would it mean to be in right relationship with money instead of trying to be right about it? This fall, I sat with Tom in his backyard in Massachusetts. We built a fire, talked about money, fear, love, and what it means to separate your worth from your bank account. What came out was an honest conversation about wealth and disconnection. An Uncomfortable Thing I Need to Name Before we go further, I need to acknowledge something that’s sitting with me. Two extremely privileged white men, born in the US, who have significant means and by most standards would be considered financially wealthy. Sitting around a fire talking about how people need to change their relationship with money. There’s real irony here. Neither of us is worrying about meeting our survival requirements. We’re not worried about a roof over our heads, food, heat, or water. We have our core survival needs met and we’re trying to thrive. So, is this just privileged navel-gazing? Two guys who have financial success saying, actually, it’s not what you want? I’m holding that tension. Because there’s another side to this. We are in positions of privilege and power. And we’re doing the actual work of examining our relationship with money, not taking it for granted, thinking about how to use what we’ve accumulated in ways that create equity and returns that aren’t just for our financial benefit but for community benefit. We’re working to disassociate our worth from the numbers in our bank accounts. Some people might look at this conversation and say, yeah, it’s easy for you to talk about changing your relationship with money when you’re not living paycheck to paycheck. They’re right. And I think that’s part of why these conversations matter. If people with resources don’t examine how money shapes us, how it disconnects us, how it controls us. If we don’t do that work and then share what we learn. The system that creates those conditions doesn’t change. Because fundamentally, we control and perpetuate those systems. So yes, this is uncomfortable. And yes, I’m naming it. Because pretending the tension doesn’t exist feels worse than having the conversation at all. I Don’t Want to Die Alone and Cold About 24 minutes into our conversation, Tom named something that I think drives a lot of our relationship with money. “What I’m hearing loud and clear is fear. And the culture of fear that is part of, particularly here in the United States, our shared condition. And I’ll invoke Jay, who I think said it for the first time: I don’t wanna die alone and cold. So, what are you gonna do about that? And in an American context, there is a somewhat ridiculous tradition of self-reliance, which manifests itself to be, don’t count on anybody or anything to be there for you.” The fear that if we don’t hoard enough money, accumulate enough wealth, protect ourselves with enough financial armor, we’ll end up alone and suffering. And what makes it complicated is this. The very things we do to protect ourselves from that fate, the accumulation, the disconnection, the prioritizing of money over relationship, those things actually push us toward exactly what we feared. We isolate ourselves trying to avoid isolation. Money is Boring. Relationship is Wealth. One of my favorite moments was when Tom just said it plainly. “I think it’s really simple, really basic, and at the heart of it, kind of boring—money. As a thing. And it distracts me and a lot of other people from that which is bigger, more complicated, more interesting. More wealth creating. Which is relationship.” Money is boring. This from a guy who spent his career in investment management. Who understands markets and portfolios and all the complexity we build around wealth. And his conclusion after all that? Money is boring. Relationship is wealth. But we’ve built an entire society around the boring thing while starving the wealth-creating thing. Counting My Wealth on a Vipassana Retreat Tom shared a story from 25 years ago. He was on a 10-day Vipassana meditation retreat, surrounded by silence and contemplative practice. And where did his mind go for comfort? “The voice, the quality that brought me the greatest solace was counting my wealth. Surrounded by the purity of a Vipassana retreat, the place where I spent the first three or four days was just thinking about what was in the savings account, what was in the investment portfolio. And it fascinated me that in this moment of clinging to anything that would offer me stability, I went to money.” I appreciate Tom’s willingness to share this. It shows how deep money’s pull goes, even in spaces designed to help us let go of everything. The Faustian Bargain of Investing Tom’s years in finance gave him a clear view of something most people don’t see. Conventional investing is built on disconnection. “By investing, I am explicitly aligning myself to a system of extraction which is completely devoid of relationship. Every part of the capital market is an abstraction, and it is a dislocation of relationship. So that’s the Faustian bargain of meeting my self-interest, assigning for myself a dependency on a market system, a capital market system, not the eggs and bread system. That is inherently inhuman because it divorces us from each other.” This landed for me. Because I’ve done the “smart” thing. I’ve invested in index funds. I’ve followed conventional wisdom. And Tom is naming the cost. By doing the rational thing with my money, I’m participating in a system that divorces me from people and place. The system we’re told will keep us safe is also the thing keeping us isolated. Risk is Fear. Return is Love. But the conversation turned here. Tom didn’t just critique the current system. He offered a different lens. “Wall Street has played the fear card brilliantly. All of the fixation and focus is on risk. And very little of the focus and fixation is on return. And I think it’s in return that we find love. So, if money is energy and I can flow money to things that I love to make those things that I love better, have more energy, places, environments, biodiversity, solving for diseases...” Risk is fear. Return is love. This reframe connects directly to what the Heart-Strong framework is exploring. What if we stopped organizing our financial lives around protecting against risk, which is fear? What if we started organizing them around return in the fullest sense? Including emotional return, community return, environmental return? What if we measured wealth by what we’re tending instead of what we’re hoarding? What is Enough? Tom brought up a question I keep thinking about. What is enough? “I think what is enough is a foundational question for every person who has degrees of fear around this subject of who will be there to care for me. And if you can succeed in answering that and following the thread of relationship, what is enough for my community, that circle of people who for whatever reasons I include with me, what is enough for them creates a beautiful lens.” The question expands. It’s not just what is enough for me? It’s what is enough for my community? Because if I’m asking what’s enough just for me, I’m still trapped in the isolation. But if I’m asking what’s enough for the people I’m in relationship with, suddenly money becomes a tool for connection instead of a wall against it. Tom shared three questions from Sherry Mitchell and Mia Birdsong. * What is enough? * What is enough for my community? * Who in your community knows and loves you, and who do you know and love in your community? That third question feels like the real wealth assessment. Because if the answer is not many, then you’re not wealthy. No matter what your bank account says. Being Right vs. Being in Right Relationship Tom offered a framework that I keep coming back to. “I was raised, I was educated, I was trained and conditioned to be right. And what I’m learning at this point in my life is to forfeit some of that rightness to be in right relationship with the understanding that I will be a wealthier person if I am able to lift up right relationship versus right. Money is in the right space as opposed to the relationship space in my construction.” From being right to being in right relationship. Our entire financial system is built on being right. Right investments, right strategies, right risk avoidance. But none of that tells you if you’re in right relationship with money, with community, with the earth, with yourself. Tom is choosing the harder path. Letting go of being right to be in relationship. And he’s honest that it’s ongoing work, not a destination. Why This Matters This conversation is part of my Heart-Strong Adventure, a year-long exploration of where love and fear show up in our world, especially in the lives of men. Tom’s journey isn’t finished. He’s wrestling with these questions in real time. He tried to build a different model of investing and admits he “failed” in market terms. But the questions remain. The work remains. I think that’s part of why this conversation matters. We need more people willing to examine how money controls us, disconnects us, and shapes our fears. Even when we don’t have easy answers. We need people in positions of privilege asking what that privilege is for. What does it mean to be in right relationship with wealth? How do we tend each other’s fires instead of ho
