I’m a retired money manager, financially comfortable, and spend 4 to 6 hours a day building my wealth.

I am not trying to grow my net worth. I have enough money.

I am focused on growing the kind of wealth that doesn’t show up on a balance sheet.

I am in the last third of my life. I want to prepare to handle aging’s relentless losses. I want to choose my path forward from a wide range of options. I want to live an exceptional life. I don’t want limited choices because I have grown weak, confused, lonely, or out of touch.

That’s why I am working on building my physical capacity, growing wiser, nurturing important relationships, and staying vibrant in our ever-changing world.

Physical Capacity

I live my life in my body. I want to walk five miles a day when I visit New York City, go for bike rides with my children and grandchildren, and feel good when I wake up. That’s a tall order. I can’t stop the natural aging process, but I can slow it down with a robust strength, cardio, balance, and flexibility routine.

Exercising has always been hard for me, so I have added a lot of support in my fitness quest. I work with a trainer. He tells me to do an exercise that seems impossible. I grumble. I give it a shot and inevitably succeed. I get regular massages to soothe my aching muscles.

None of this is cheap. What better way to spend my money?

Growing Wisdom

I am not as smart as I used to be. My intellectual processing capacity has diminished. I can’t think as fast as I used to; it is harder for me to do math in my head.

I am becoming wiser. At 67, I have a plethora of life experiences that contain hidden nuggets of wisdom. To uncover those nuggets, I read insightful people on a broad range of topics and apply what I am learning to my prior life experiences.

Here’s an example. I repressed any feelings of sadness for decades, worrying that sadness would make me weak and vulnerable. I recently read that love and wisdom can grow out of sadness. It hit me like a sledgehammer! Pushing away my sadness during tough times isolated me from close friends and kept the wisdom hidden.

Today I am working on just being with my sadness, not pushing it away. Turns out that my friends see strength in sadness, offer their love and support, and our mutual connection deepens. Nobody thinks of me as a weak and vulnerable wimp.

I’m not surprised I repressed my sadness. Many men in my generation did the same. What’s surprising is how long it took me to internalize the cost.

Nurturing Relationships

My close relationships are my most valuable asset. I have many friendships filled with love, acceptance, vulnerability, and authentic communication.

To keep my relationships strong, I call people when too much time has passed since our last conversation. Sometimes my call comes at just the right moment. They are struggling and need to talk.

I frequently enjoy lunch or coffee with friends. Having a one-on-one conversation offers the time and space to talk about personal issues. Topics range from politics to sports to investments. When something is going on for me or my lunch partner, we are able to talk about it and support each other.

Staying Vibrant

The world is changing at a dizzying pace. I want people to value what I add to the conversation; not to listen politely to the old guy who used to be successful. The last thing I want is for my children or younger friends to groan inwardly when I pull out the same old story.

Most of my friends are roughly my age. I want to build closer friendships with people who are 20 to 30 years younger. I hope that being with bright, talented, caring people in their 30’s and 40’s will help me engage with the world as it is, and not as it used to be.

Life is short, precious, and unpredictable. I don’t know what is coming my way; I do know I want options as I choose how to live my life. I hope my continuing investments to build the wealth off my balance sheet will give me the options I crave.

How about you?…

Until our next conversation,

David

Small Steps & Worthy Questions

1. What options for yourself do you want to preserve over the next 10 years, and what would it take to protect them?

2. Invest in one form of support you’ve been resisting. Maybe a trainer, therapist, or life coach will enable you to make more progress.

3. Focus awareness on one emotion you habitually push away. Don’t try to fix it. Don’t analyze it. Just notice what happens when you let it be present.

4. Consider what forms of wealth you are still actively growing–and which you have been neglecting.

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I’m often scared.

When I’m feeling frightened, I spend valuable time reading and thinking about my investments. I rationalize, telling myself I am just being responsible. I want to make sure my portfolio is positioned properly in a changing world.

I’m lying to myself—pretending this is prudence, when it’s really avoidance.

Why do I do it?

I am scared of economic realities such as our monstrous national debt, and of the deep political divisions that threaten the stability of our country.

Focusing on my investments is like giving myself a pacifier. It comforts me; it doesn’t nourish me.

Why don’t I stop? Because it is an effective way to distract myself from what is really bothering me.

I am reluctant to confront my own mortality. I am 67. The older I get, the faster the clock ticks. I am acutely aware each day is precious. I desperately want to spend my time wisely.

I fear my life is misaligned with my values and priorities. When I’m honest with myself, the problem isn’t that I lack knowledge of what matters most to me. My soul knows.

Implementing that inner wisdom is what’s challenging.

Years ago, thought leader George Kinder offered three questions to help people uncover the life they want. I find they help me tune in to my deepest yearnings.

1. The first question is deceptively simple.

If you had all the money you needed—today and for the rest of your life—how would you live? What would you do? What would you change?

For me, the answer is unsettling. I already have enough. More money would not change my life materially. Which raises a harder question: If money isn’t the constraint, what is?

2. The second question sharpens my focus.

Imagine your doctor tells you that you have five to ten years left to live. You won’t feel sick. You’ll die suddenly one day. Knowing that, how would you live? What would you do differently?

What I would do differently is spend less time preparing for imagined futures that may never arrive.

What I want to do instead is spend more time inhabiting the life I already have. More time deeply appreciating the moments that matter most to me. That means caring for my wife in ways big and small. I want to console my dearest friends in the tough times and celebrate our triumphs together. I want to encourage my children when they falter. I want to sing my favorite songs from Les Misérables or Ed Sheeran, get down on the floor with my grandchildren to play the games they love, deepen my faith through prayer and study.

Some of this may make me feel silly. What will people think? Maybe friends will misunderstand. Talking about my faith sometimes is met by silence or discomfort. Being true to myself is not always easy. But if not now—when?

3. The third question is the one I resist the most.

Imagine your doctor tells you he made a terrible mistake. You will die—peacefully and painlessly—in the next 24 hours. Looking back, what did you not get to do? Who did you not get to be?

This question strips away pretense. What remains is regret, longing, and truth. It reveals the cost of caution. The price of fear. The opportunities quietly passed over while waiting for a better time.

Sitting with these questions gives me more than answers. It gives me clarity. I can no longer pretend that shuffling my investment portfolio will quiet my fears. I cannot default to my comfort zone. I must do what my soul craves if I want to live an authentic life without waiting any longer.

I can’t go back to pretending. I’ll pay the cost.

Until our next conversation,

David

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For a long time, I thought good decision-making was primarily an intellectual exercise. Clarify the objective. Ask good questions. Gather information. Identify options. Weigh the pros and cons.

That sounds reasonable. It’s a good start. And it’s woefully insufficient.

I am an emotional, spiritual man. When I am emotionally off-kilter or disconnected from my soul, my decisions almost always end poorly—no matter how rational they appear on paper.

Early in my career, I wanted to be “successful.” I defined success intellectually as being in a prestigious, high-income profession. Becoming a high-powered lawyer fit that definition perfectly. I worked incredibly hard, graduated from a top law school, landed my dream job, and excelled. I was miserable. Twenty-two months later, I quit.

I’m an entrepreneur at heart; big law firms are not entrepreneurial. Being a lawyer didn’t mesh with my heart.

Over time, and with the guidance of a therapist, I learned to factor feelings into my decision-making. He taught me that connecting with my feelings was a good way to figure out what I really wanted. While I once considered feelings to be a nuisance and something to overcome, I came to recognize them as a source of wisdom.

Now I know that my best decisions happen when I am calm, centered, and connected. Here’s what that means.

Calm

When I am agitated, I make poor decisions. The more agitated I am, the worse my decisions become. My fears crowd out perspective. I focus on short-term relief rather than long-term wisdom.

I get worked up easily. I come from an anxious family. I live in a world saturated with catastrophic, fear-inducing messages. Health scares, political crisis, and interpersonal conflict are part of everyday life.

Now that I’ve developed more awareness of what I’m feeling, I’ve learned it’s far better for me to build the capacity to stay calm than to try to calm myself down once I’m already upset. Better—but not easy.

I’m slowly building what I think of as a calm reservoir.

How I do it:

• Limit exposure. Minimize time with people and content that push my buttons or spark my fears—especially around things I can’t control.

• Care for my body. Regular exercise, decent nutrition, and good sleep improve how I think and feel.

• Nurture my my soul. Silence, nature, and content that feed my spirit calm me in ways nothing else does—especially when these practices are built into my routine.

• Community. When I’m immersed in a community of kind people with shared values, my nervous system relaxes and my heart opens.

Centered

I have a limited amount of time, attention, and money.

Every time I say yes, it’s also a no to something else, often at the expense of my peace of mind. When I feel hurried and scattered, I make decisions I regret. I end the day depleted.

When I am centered, my decisions align with who I am and what matters most. I end the day peaceful and confident. The difference is striking.

To move from scattered to centered, I slow down. I pause. I breathe. I notice what’s happening in my body. I remind myself what matters most to me. I ask myself a simple question: What do I actually want to do?

I resist the urge to decide immediately. I need time—to process, to listen, to hear my inner voice. I’m learning to give myself that gift.

Connected

I am neither separate nor alone.

My life is a web of connections—to my wife, my family, my friends, and my community. In moments of awe, I feel connected to all living things, to the universe, to God.

When I feel connected, my perspective widens. I stop asking, What’s best for me right now? and start asking, What’s best for me as part of something larger?

I see myself as a steward of both my financial and intrinsic wealth. The crisis du jour loses its grip. My sense of time lengthens. I loosen my hold on what I have, and my kindness, compassion, and generosity grow.

Even in the best circumstances, making good life decisions is hard. It’s far harder in a fear-inducing, money-centric, and deeply divisive culture.

Staying calm under stress, recognizing the role that feelings play in decision-making, remaining centered on what matters, and staying connected to others takes consistent, mindful effort.

What’s the reward for that effort?

A more meaningful and joyful life.

Until our next conversation,

David

Small Steps & Worthy Questions

1. Before responding to a request or making a decision, give yourself permission to pause. Have you given consideration to your feelings?

2. What helps you feel calm, centered, and connected—and why do you often neglect it?

3. Limit exposure to one person, habit, or stream of content that disrupts your calm.

4. Consider what decisions in life you may be making from fear rather than from clarity.

5. Choose a small, repeatable practice that helps you return to calm—walking, silence, prayer, movement—and treat it as essential.

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I’m lucky. My children are thriving—married to caring souls who fit them well, raising my adorable grandchildren, working in jobs they enjoy, and navigating life as best they can. They are independent adults running their own lives. Still, they know that Heidi and I are here as their safety net. I have told them repeatedly, “You will never be hungry or homeless.”

Yet even with all that love and good fortune, my relationship with my adult children is complicated.

It’s complicated because of my desire to protect them. Their lives are far from perfect. Sometimes, when we talk, I hear their worries, stress, frustrations, and tiredness. My heart aches. I’ve written before about how we often find ourselves only as happy as our unhappiest child, and it is a difficult place to be. What, if anything, do I do?

It’s complicated because I have unique expectations for my kids. As Heidi and I suffer the inevitable declines of aging, our independence will wane. I hope and expect the children will help with the parts of our life we can no longer manage on our own.

It’s complicated because our perspectives are different. My Grandma Lucy quipped: “Generations can only visit each other”. We were raised in very different environments. My kids are in the busy time of life, juggling jobs, children, and marriage. I am retired, no longer climbing the success ladder. They are in the first half of life; I’ve entered the last third of mine.

Bottom line: I want a close and loving relationship with Rachel and Daniel. I want to be an important part of their lives without infringing on their independence. I want them to live their best lives as I live mine. In that pursuit, here are four tenets I keep top of mind.

1. Acknowledge You Don’t Know What’s Best

When my children were young, it was my job to decide what was best for them. Not anymore. They are independent adults in charge of their own lives, with their own inner wisdom. I’m blind to some of their hopes and fears. Their choices should reflect their values, not mine.

Letting go of the belief I know what’s best for them is a challenge for me. Old habits die hard.

2. Be A Sounding Board

When my children open up, my job is to listen. To be curious. To ask them questions to help uncover their blind spots. To give advice only when asked.

When I feel an irresistible urge to give advice, I ask for permission to offer suggestions. I remind them they can tell me “no”. If they do choose to hear my ideas, they don’t have to follow them.

When I do this well, I give my kids the space to connect with their own wisdom.

3. Allow Them to Struggle

Watching my children struggle is far harder than navigating my own challenges. I feel a giant tug to save the day, to take away the source of their angst.

I do my best to resist that pull. Rescuing them denies them the knowledge that they can navigate life’s difficulties without me. My heartache is poor reason to rob them of their resilience.

4. Focus On My Own Life

When my children were young, I was a lead actor in their life play. Today, I’m a supporting actor. It’s a role that requires us to separate our own emotional well-being from their temporary struggles, ensuring we don't lose ourselves in their drama.

When my own life is full—when I focus on my health, my relationships, my spiritual work, and the purpose I feel called to live into—I stop trying to live my children’s lives for them.

And when I stop trying to live their lives, I’m more available to love them as they are.

A robust personal life is one of the most generous gifts I can give my kids. It frees them from the burden of being responsible for my fulfillment.

Why This Matters

Money, purpose, family, and legacy are intertwined. As a Dad, I want to offer support without overstepping. I want to be generous without creating dependence. I want deep connection without imposing on my children’s autonomy.

I don’t have all the answers. As I grapple with complicated questions, these four principles help me love my children deeply, accept who they are, and tend to my unfolding life.

I hope you find them useful.

Until our next conversation,

David

If you are currently navigating a season where your child is struggling, you may also find comfort in my previous post: As Happy as Your Unhappiest Child.

Small Steps & Worthy Questions

1. Where are you still holding onto the belief that you know what’s best?

2. Consider if you are pursuing interests that give you purpose beyond your role as a parent. A fuller life for you is a lighter burden for your adult children.

3. Is your motivation about easing their struggle—or easing your discomfort?

4. Ask what they need before you offer anything. Consider their request carefully. Is it something you want to do? It’s ok to say “no”.

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Sometimes I struggle with how to spend my time. It’s easy to think about “should-do” tasks morning, noon, and night. It’s hard for me to get in touch with what I really want to be doing. Harder still to do what I want and let the “shoulds” fall by the wayside.

When I do take action on my heartfelt desires, my inner critic attacks me for wasting my time, wasting my money, wasting this precious gift of life.

I love driving a convertible. Been fantasizing about buying a luxury sports convertible for over a year. I have the money. The problem is I felt guilty every time I imagined buying the convertible.

I was caught in limbo: wanting the convertible and not giving myself permission to buy it.

Why was I torturing myself?

I grew up in a family with both spoken and unspoken rules about almost everything.

Always do your best, and doing your best meant working really hard. Use your gifts to make the world better. Be kind and compassionate. Protect and defend your siblings. They are your only lifetime relationship. Always save for a rainy day. Don’t waste money on frivolous things. Those family rules are ingrained deep in my psyche.

I am always grateful to be the son of Andy and Nancy Geller. I am proud of my parents and their rules are generally good ones.

At important decision points in my life, my impulse is to follow my childhood family rules, to do what I “should” do. When I act on that impulse, I don’t give myself the opportunity to consider and do what I want to do

I forfeit my freedom to choose how to live my life.

I purchased a plug-in hybrid Volvo sedan less than 3 years ago. Trading in a perfectly good environmentally friendly car for an all gas convertible seemed frivolous. When the sports car desire arose, I squelched it and told myself keeping the Volvo was the “right” thing to do.

The “shoulds” from my parents overrode my wants.

With the encouragement of my wife and friends, I eventually woke up to a sobering truth: time is short, and I don’t want to keep postponing joy. I have worked hard and acted responsibly my whole life. My soul craved more fun, more woo-hoo moments.

I bought a beautiful blue BMW convertible.

I love the thrill of driving with the top down. Even more, I love that I gave myself permission to do what I really wanted. That is the key. Allowing myself the space to discover what I want, and trusting my soul’s desire. It takes time and consistent effort. None of this is easy.

My inner voice, has a lot of wisdom to offer me. I just need to trust myself enough to sense into what it is telling me, and to trust its guidance.

What about you? Where in your life are you following the “shoulds” when your heart is quietly asking for something else?

Until our next conversation,

David

Small Steps & Worthy Questions

1. I imagine that your family also had spoken and unspoken rules. What were some of the most notable?

2. Give some thought to which of those childhood messages are helpful. Which ones need to be modified or just thrown out?

3. How might your life be different if you trusted your own inner voice more often?

4. Does anyone in your life encourage you to listen to your inner wisdom and ignore the “shoulds”? Consider getting more support from those people

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For most of my working life, I was a big fish in my little pond. My brother and I were the majority shareholders of our mid-size Atlanta wealth management firm. I set the firm’s direction, and worked with many of our largest clients. I relished leading the team, and being responsible for our clients and my colleagues.

I was good at my job. People appreciated my efforts and I received a steady diet of praise, respect, and gratitude.

In 2020, I sold the business. I went from being CEO of my own firm to being someone who reported to someone who reported to the CEO. I felt small. Nobody asked my opinion. Nobody sought my advice. Nobody stroked my ego.

I didn’t like it. I retired almost immediately after the last of the sale proceeds hit my account.

Retirement was a shock. For the first time in my adult life, the calendar was blank. I could do whatever I wanted. It was disorienting and exhilarating.

Then it became scary. Without all that praise, I questioned my personal value. Was I being lazy, wasting my time, talents, wisdom and treasure?

I felt the pull to go back to work or start a new venture. To be “big” again. Thankfully, I had promised myself to refrain from long term-commitments for at least a year. I really needed time to rest, explore, and see what my heart craved.

Early in my year of no commitments, a former colleague called for help in handling a challenging client. I started to engage, and then I stopped dead in my tracks. I was no longer responsible for the firm’s 400-plus clients or more than 30 employees. Not responsible for strategic decisions, potential threats, challenging clients.

I discovered the joy of feeling small.

Feeling small opened my eyes. My mind wandered. I opened up to new ideas that had nothing to do with my former business. I stopped seeing new acquaintances as potential clients, and started seeing them as potential friends. I no longer meditated with the hidden agenda of recharging my batteries in order to work harder; I now meditated and prayed to connect with my inner voice, my soul.

Much more satisfying.

I felt liberated as I loosened my grip on being the dynamic leader with the right answers. I didn’t have to be perfect. I could strike a balance, do my best, and be open to whatever came my way.

I started noticing the little things. Two friends laughing. A father playing with his toddler. Striking fall colors. My dog Sophie’s unabashed delight when I walked through the door.

I spent more time being with my friends–laughing, playing, talking about what matters most, which almost never involves financial discussions. Reminiscing about our history together. Sharing our hopes for the future. Expressing our love.

Now that I am not the boss, I no longer feel a compulsion to fix the problems. Instead I offer wholehearted listening with empathy and compassion. Giving friends and family the space to navigate their own path forward. Life is filled with joys and sorrows.

I am learning to be present.

Being small helps me connect. As the boss, a power dynamic separated me from my colleagues and from my clients. That limited the conversations. Hard for people on either side to express themselves honestly and fully. Now that I’m no longer “the Man”, that power dynamic is diminished. My relationships are more candid and vulnerable.

Most of all, this new mindset opened my eyes to a reality I had been ignoring for a long time. I am smaller than small, and so are you. We are one of 8 billion people on a small planet in a vast galaxy that is a tiny piece of an almost 14 billion year old universe. We are here for a brief moment, and soon forgotten.

Thank goodness!

We are way too small to fix the world’s problems.

Our job, as individuals in a vast universe, is to be grateful for the miracle of existence, to live with love, compassion, and joy, and to leave the world a little better off than we found it.

I can do that, and it’s all I can do.

How about you?

Until our next conversation,

David

Small Steps & Worthy Questions

1. Imagine watching your funeral. How do you want family and friends to describe how you spent the time between today and your passing?

2. Block out some time on your calendar. When the time arrives, pause, take a few deep breaths, and ask yourself, “What do I want to do right now?” Don’t critique yourself, just do it. How does that feel?

3. When you peel away the veneer of business and professional success, what else makes you a valuable person?

4. Find a person in their 20’s or 30’s (child, grandchild, family friend), and share your wisdom about life, love, and meaning. What role did your business success play in your story?

5. If you had to spend a year not working, what would you do? How might you feel at the end of the year?

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I think quite a bit about the time I have left. I don’t want to fritter away my days. I want them filled with love, joy, meaning, fun, and—if I’m lucky—a deep sense of purpose. I want to dance at my grandchildren’s weddings. To do that, I have to live a long, healthy life. My grandchildren are 7, 4, and 1.

Building a rich and fulfilling life requires discipline. I am a disciplined person, and I struggle to do the things I need to do. My wife Heidi always tells me,

“If it’s hard for you, it’s really hard for most people.”

My solution is small steps. I add one thing to my routine that is helpful, and when I have internalized it, I add another. No rush. Progress is all that matters.

In my quest to build the life I desire, I contend with what I call realities to face and problems to solve. I want to be healthy. One challenge is high cholesterol and heart disease run in my family—that’s a reality to face. But it’s also a problem I can work on. I take medication, listen to my cardiologist, and work out with a trainer.

I used to criticize myself for needing that help. I now see it as an act of self-love.

Taking care of myself physically is comparatively easy. The harder challenge is managing my emotional and mental distractions. I’m easily pulled into social media rabbit holes that leave me anxious or outraged. Thankfully, my Jewish faith helps me return to center.

Each morning I feed my soul through meditation and prayer. Each week I read stories from the Hebrew Bible about flawed humans wrestling with real-life struggles—moving from slavery to freedom, anguish to hope, isolation to connection. These stories are thousands of years old, yet they feel relevant today.

On Friday nights, Heidi and I attend services and join in communal prayer. I love it. I feel connected to those around me, grateful for my blessings, and compassionate toward those who are suffering. I sense a divine light within each of us—and hope that together those lights might help heal a fractured world.

When I connect to that love within and around me, it’s easier to be generous with others and with myself. My angst softens. In its place, joy and contentment arise. I can relax and enjoy the moment.

Meaning doesn’t require a grand plan—just a willingness to notice, to show up, and to care. Meaning-making opportunities abound: telling a young father his children are adorable, encouraging a friend through a rough patch, or donating to a food pantry whose shelves are empty.

Purpose, though, is a tougher nut to crack. I define it as using your intrinsic wealth—your time, talents, wisdom, and character strengths—to do something you feel called to do. What makes your heart hurt? What might your gifts help to heal?

Purpose rests on a foundation of connection, courage, and strength. Connection reminds us we’re part of something larger—that every living being carries a sacred spark. Courage lets us step into uncharted territory and use our gifts in new ways. And strength helps us get back up after we stumble, learn from our mistakes, and begin again.

My own search for purpose is ongoing. This blog is part of it. My heart aches when I see good people who have achieved financial success yet still feel something is missing in their lives. I see others in need who would benefit from the wisdom, compassion, and generosity of those same people.

It hasn’t been easy. I hired a writing coach to help me become a better writer. The process has been both invigorating and humbling. I’ve learned that finding your voice—on the page or in life—requires discipline, vulnerability, and the willingness to start over when you lose your way.

I wake up each day trying to live the life I write about—one filled with purpose, connection, and joy. Some days I succeed. Some days I just begin again.

Until our next conversation,

David

Small Steps & Worthy Questions

1. Your path to an exceptional life will look different from mine. Ask yourself, what does an exceptional life mean to me at this stage?

2. Feed your soul daily. Set aside ten minutes for prayer, meditation, or reflection before turning to your phone or the news.

3. What makes your heart hurt—and how might your time, wisdom, or resources help?

4. Look for small moments of meaning. Each day, notice one opportunity to offer kindness, encouragement, or gratitude. Notice how that makes you feel.

5. Where in your life do you need more self-love?

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Being retired has been a joy and a jolt. A joy to celebrate a career that gave me so much, and to savor my free time and consider what comes next. A jolt to stop striving, to lost earned income, to no longer be part of a team.

I feel good about how far I’ve come in three years since retirement. I don’t think much about my former company. I have grown comfortable living off my investments. My days are filled with family and friends, growing spiritually, writing Wealth & Fulfillment, and living a healthy lifestyle.

Even with this progress, my transition is not complete. I struggle disconnecting from the chatter in my head–old success messages that once served me well. Messages like work harder than everyone else, don’t waste time letting your mind wander, avoid controversial positions that might upset clients, be vigilant against any potential threats, if it’s valuable then it must be costly.

My life has changed. Yet I have to keep reminding myself that I’m not working, I’m not responsible for employees, I’m not the largest shareholder of a $1 billion asset management firm.

I don’t have client-friends. I just have friends. I don’t need to prove myself and add value. I am worthy just the way I am.

These old beliefs, once helpful, have morphed into stumbling blocks in building my new life.

I don’t want to work hard. I want to spend time with loved ones, live a healthy life, and connect with the quiet voice inside of me.

I don’t want to focus incessantly. I want to let my mind wander and see what I discover.

I don’t want to be hypervigilant. I prefer to look for the abundant good in the world.

I don’t want to be indispensable. I want to be loved for who I am, not what I can do.

I don’t want to use money as a measuring stick. Much of what I value the most is free-- the love of friends and family, nature’s beauty and calming effect, the pleasure of sharing empathy and a smile with strangers.

My old messages are annoyingly sticky. They have been in my head for almost 40 years. I feel uneasy giving them up. Am I sure they no longer work for me? Will I be OK without them? It feels a bit like turning my back on an old friend. After all, they helped me become the man I am today.

I want to put them behind me with a loving heart. Acknowledge how much they helped me, cultivate gratitude for having them, and recognize they no longer serve me. I plan to buy a wooden box, decorate it, write each old message on its own piece of paper, and place the messages in the box. Invite some friends to join me as I bury the box–saying goodbye and offering thanks to my longtime companions.

I’ll replace them with new messages, aligned with my new life, with the life my soul desires. Here are the ones I am focusing on now.

Embrace My Faith

Build my life around the wisdom of the sages, practices to cultivate gratitude and connection, and acts of loving kindness to help people in need.

Value Quiet and Stillness

Connect with the wisdom inside of me.

Express My Love

Nurture my closest relationships; treat strangers with love, empathy and a smile.

Be Generous

Feel the joy of sharing my abundance.

Notice The Beauty

I am surrounded by so much ordinary beauty–the sun shining, a stranger’s smile, a toddler learning to walk, two friends having coffee.

Recognize My Value

I am created in the image of God, just like you.

My inner voice is powerful. It is with me all the time. I am learning that for me to build the life I want, sometimes my voice needs to change its tune.

Do you need to say goodbye to some old success messages, and welcome new ones into your life?

Until our next conversation,

David

Small Steps & Worthy Questions

• Think about the life you want to live going forward. How is it different from the life you wanted as a young adult?

• What success messages helped you become who you are today? Are any of them holding you back from the person you hope to become?

• What messages does your soul long to hear?

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I was the CEO of a wealth management firm for years. I understand how to build investment portfolios, interpret financial projections, and craft estate plans.

People are surprised that my wife, Heidi, and I have our own financial advisor. Why would I hire someone to do something I could do for myself, especially now that I am retired with plenty of time?

I have a financial advisor because I need one. If that is true for me, someone with more than 30 years of wealth management experience, it is almost certainly true for you.

Here’s why.

I am human. Managing my own money is different from managing other people’s money. I am more likely to make emotional decisions I will later regret.

I love my wife. I am more than a decade older than Heidi, who is not a financial person. When I pass, I want her to have a relationship with an advisor she trusts. An advisor who will help her think through important financial decisions with confidence.

I have better things to do. Superior wealth management takes time. I would rather outsource it to professionals and free up time to write my blog, spend time with friends, travel, and play with my grandchildren.

Easy for me to find an advisor, of course.

Finding the right advisor might be a challenge for you. To give you a better sense of what to look for, here is a brief description of the relationship with our advisor.

• Our advisor works with his company’s investment team and an outside consultant to build our globally diversified portfolio. He regularly rebalances our portfolio and captures tax losses.

• In turbulent markets, he proactively reminds us how our portfolio is designed to give us the money we need during a severe and long lasting market downturn.

• He prepares financial projections that guide our long-term decision making, utilizing complicated software and sometimes accessing an in-house expert when he has to model an unusual situation.

• Every three years, we review the estate plan to confirm it remains aligned with our values and desires.

• We periodically review our life, disability, and long-term care needs, and develop a risk-management plan to fill in any insurance gaps.

• His team helps us handle the daily details of our financial life such as funding our checking account each month so we can pay bills, and providing our accountant with year-to-date interest, dividends, and capital gains from our portfolio.

Unlike many of his competitors, our advisor understands what money is, and is not. He knows that money is a tool–not a metric for success, self-worth, or security. He understands the true power and the limits of our money. Money allows us to purchase the things and experiences money can buy–new cars, nice clothes, luxury vacations, college educations for grandchildren. Money can’t buy friends who love us, the self-confidence to overcome adversity, or a deep sense of purpose.

Our advisor reminds us that time is our most precious resource. We have plenty of money; we don’t know how much time we have left.

Instead of merely focusing on growing our net worth, he encourages us to use our money to grow closer with family and friends, to enhance our spiritual lives, to have more fun, and to give joyfully to family, friends, and charities.

He always has our back. He would never allow us to put our financial security at risk. He guards our precious time, helping us focus on what matters most. He helps us build a life at the intersection of joy, meaning, and fun.

You deserve nothing less.

Until our next conversation,

David

Small Steps & Worthy Questions

• Send this blog to your financial advisor to start a candid conversation.

• What does your financial advisor need to know about you that you have not yet told him or her?

• If you don’t have an advisor, network with friends and colleagues to find two or three who might be a good fit. Interview them and choose one

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I have several close friends who are struggling. Some are battling life-threatening health issues. Others are struggling with family challenges: aging parents who need support and refuse to accept it, the sudden, tragic death of a sibling, political angst driving relatives apart.

My heart aches for my friends. I want to help them. Not at all sure what to do. They don’t need financial assistance. Words of comfort seem inadequate. Platitudes like “everything happens for a reason”, or “you will get through this” are insensitive and tone deaf.

I love my friends; I can’t just sit around doing nothing. I’ve discovered that not only are they grateful for the compassion, comfort, and support I offer, but I also receive immeasurable benefits that remind me of the inner wealth I possess.

I spend time with them. Instead of assuming what they want from me, I sometimes ask if they want to be hugged, heard, or helped. I use my talent of being a good listener. When they want to talk, I give them my undivided attention. Periodically I summarize both the content and the emotion of what I heard. I want them to know I am with them, body, heart, and soul.

As a wealth manager, I developed the skill to help people think through difficult decisions and figure out the right answer for them. I use that skill to help my friends:

• Accept what I call Realities To Face (RTF)

• Focus their time and attention on Problems To Solve (PTS)

• Allow themselves to feel their fear, anger, and sadness, with a loving and compassionate heart.

If they need professional assistance, I use my network to help them find the right person or company.

As I help my friends, they help me. Helping people I love is deeply rewarding. I can’t make their problems vanish; I can ease their burden, if only for a while.

They show me how life can be beautiful and meaningful, even when it is incredibly difficult. As a man who didn’t shed a tear for almost four decades, they show me the sweet side of sadness. Their courage in the face of pain and fear encourage me to embrace my life as it is instead of wishing it was different.

Their tough times help me to accept on a visceral level that I, too, will experience hard times. I comfort myself that we get through hard times with the love and support of our closest relationships, and with our internal reservoirs of strength.

I occasionally use my money to help friends. I may send a small gift, or invite them to spend time with Heidi and me at a home we rented for a few days. Mostly, my money just isn’t helpful. Money is only good at buying things money can buy, and what they need can’t be bought with money.

All this leaves me wondering why I reflexively think of money as the most valuable aspect of my true wealth, which includes not just my money but my inner wealth. Am I buying into the mistaken belief that life continually gets better as your financial wealth grows? I somehow forget Einstein’s quip:

Truth is, I feel safe, even invincible, knowing I have enough money to provide for my family. Of course, that is delusional as my friend’s struggles demonstrate.

When times are tough we often get knocked off our feet in a tidal wave of fear, despair, and sadness. That is just how life is. When the tidal wave passes, we have the chance to love each other.

How have you navigated the tough times? How have you helped loved ones navigate their own challenges?

Until our next conversation,

David

Small Steps & Worthy Questions

• Ask a struggling friend: Do you want to be hugged, heard, or helped?

• What forms of inner wealth do you rely on in hard times?

• Journal about a time when hardship revealed unexpected beauty or connection. Name three forms of your inner wealth that you could share today.

• Who in your life has shown you the sweet side of sadness?

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I bought $500 tickets to a hot Broadway musical.

My inner critic tortured me. The voice in my head shouted:

“This is ridiculous. You could have purchased deeply discounted tickets to any number of great Broadway musicals at the ticket broker in Times Square. Maybe even to the $500-a-ticket show!”

“Are you too lazy to wait in line for an hour to save hundreds of dollars?!!!”

That’s what I call my “value voice.” The internal dialogue that says, “You can spend a lot of money on something you want, but only if it is a good value.”

My value voice tortures me. I am working hard to lower its volume. So much of what my value voice says is crazy!

How so? Let’s start with there is no clear standard for value. So this internal voice isn’t expressing facts but gut feelings – what I imagine my parents would have told me.

Here are some facts. I am 66 years old. I have been a good steward of money for my whole adult life. My wife and I can afford the tickets. Purchasing them will not change our financial future. We really want to see the play. My eyesight is not perfect. I like sitting up close so I can see the actors’ facial expressions. We are only in New York for a few days. I don’t want to waste my time standing in line to save a few dollars that won’t impact my life.

Still, the value voice is relentless: “It’s not worth it.” Hard for me to make that mental chatter go away – and stay away.

Why? I’m not sure…

Maybe I subconsciously frame each transaction as having a winner and a loser. Winners get a good value, or better yet, a bargain. Losers pay too much and are separated from their money. I’m a money-savvy person. This is a game I should win.

Those thoughts are not factual. There are no winners or losers in the Broadway show ticket market. The price is just the price. Today the tickets are priced at $500. If the tickets to the show don’t sell, the price will come down. If they sell quickly, the price for the remaining tickets will go up.

Maybe I fear I’ll need the money someday, that my fortunes will turn, and I won’t have enough money to save myself or my family. I imagine myself swimming in a sea of regret, wishing I had been less extravagant.

Another fallacy. I can purchase the tickets today without impacting my life. If my financial situation turns south, I will make different spending decisions. I have always spent within my means. No reason to expect that will change.

But what if overnight my net worth plummets 50%, 70%, or more? Won’t I then regret purchasing the $500 tickets or spending my money in other wasteful ways?

My money is invested in a globally diversified portfolio. It won’t all vanish overnight. My wife and I own our house free and clear. We have no debt. We have sufficient insurance to protect us against an unexpected, catastrophic liability claim.

I once had a client who held onto his millions tightly, just in case someone he loved needed it. I encouraged him to set aside enough money to deal with foreseeable risks, and to enjoy the rest by spending it or giving it away. He refused. When I asked him why, he looked me squarely in the eye and said, “You never know what the future holds.”

He is right. None of us know what the future holds. That is just life. All we can do is take prudent steps to protect ourselves from foreseeable risks, trust that we will do our best to navigate whatever challenges come our way, and live life to the fullest as best we can.

I wonder if all my rationales for holding onto the money are a smoke screen. Maybe what I really fear the most is that part of me believes the money I die with constitutes a scorecard for my life. The more I leave behind, the more successful I was. My inner adult knows this is ridiculous. My scared inner child has his doubts.

My value voice is persistent for all of these reasons. I can’t make the voice go away completely. What I can do is choose to live my life fully, trust myself to provide for those I love, and give myself permission to purchase $500 tickets to a Broadway show that I really want to see.

Is your value voice holding you back from living your best life? Is it time to tune out that voice?

Until our next conversation,

David

Small Steps & Worthy Questions

• How would your spending decisions change if you trusted that you’ve prepared responsibly for the future? If you haven’t already, define the financial guardrails that protect your future (insurance, savings, no debt) so you can confidently spend within them.

• Take some time to consider how you personally decide when something is “worth it”? What experiences are you denying yourself because of old money habits or fears? Ask whether this purchase will materially affect the family’s long-term security? If not, give yourself permission to proceed.

• Look for opportunities where spending a bit more buys back your most precious resource: time.

• Choose one experience this month that will bring joy or connection and spend freely on it.

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To help us do that, I’m launching the Wealth & Fulfillment subscriber chat.

Think of this as a digital front porch where we can hang out as a community. I plan to share quotes that resonate with me, thoughts on recent events, or questions about the challenges we all face. It is a space for us to support one another and find a little more clarity together. You can jump into the discussion when the spirit moves you.

I hope you’ll join the conversations, particularly as we approach my next topic: “The Financial Advisor You Deserve.” I am eager to hear your thoughts and experiences on that subject in the chat.

Join chat

How to get started

1. Get the Substack app by clicking this link or the button below. New chat threads won’t be sent sent via email, so turn on push notifications so you don’t miss conversation as it happens. You can also access chat on the web.

Get app

2. Open the app and tap the Chat icon. It looks like two bubbles in the bottom bar, and you’ll see a row for my chat inside.

3. That’s it! Jump into my thread to say hi, and if you have any issues, check out Substack’s FAQ.

I am a fortunate man. I’m in good health. My marriage is exceptional. My adult children are finding their way through life, with its inevitable joys and struggles. My grandchildren are adorable. I have my faith to guide me forward, and close friends and family to share in my joys and sorrows. Writing Wealth & Fulfillment gives me purpose as I weave together my life experience and insights.

All good - except I find myself struggling to cope with the flood of bad news battering our world. There is so much hate and divisiveness, leaving me angry and fearful. My blood pressure is up. My muscles are tense. I’m sleeping less soundly.

I tell myself to turn off the news. It makes no sense to focus on events I can’t influence, much less control. Still, tuning out is hard—maybe impossible for me. World events still seep into my consciousness. I ruminate over what I should do.

I know I’m not alone. Many friends share my angst. What can we do? I am beginning to discern a new direction—less like a solution and more like a compass.

I want to be the antidote to division and distrust. I want to see each person as inherently valuable. May I notice their strengths and gifts, honor their struggles, and see their humanity. I want to greet people with warm smiles and kind eyes as I listen with curiosity, ask genuine questions, and reflect back what I hear to minimize misunderstandings. I want to share my perspective with stories that are honest and balanced. Knowing both sides hold a piece of the truth, I want to seek common ground.

I want to ground myself in the present. Focus on what’s happening now - not on what I fear may happen someday. My fears rarely materialize, and my worrying never helps.

I want to bask in the good that surrounds me - mornings filled with sunshine, cool winds, and chirping birds. Loving parents raising kind children. Adult children caring for aging parents. Local nonprofits serving the lonely, hungry, and homeless. Medical research creating groundbreaking treatments allowing so many to live longer, fuller lives. I’ve seen remarkable progress in my lifetime. We live in an age of miracles my grandparents never dreamed of.

Future challenges await me. Everyone struggles with loss and difficulty. I pray for the presence to accept what is, and the strength to walk forward with wisdom, grace, and love. That’s a tall order. Thankfully, I’m surrounded by people who love me - and I’m supported by a faith that guides me.

When I feel overwhelmed by the avalanche of bad news, I remind myself:

I can’t fix the whole world, but I can make a difference in my corner of it.

I can be generous in my philanthropy, supporting organizations that tackle homelessness, hunger, injustice and more. I can bring groceries to a food pantry, check on a friend having a rough time, stand up to intolerance when I encounter it.

I can look a homeless person in the eye and treat them like someone who matters - because they do.

Doing this may feel like a tall order. How do you begin? Just start. One small act of unexpected kindness. Human to human. Eye to eye. Ask the grocery store cashier how their day is going. Buy them a candy bar. Thank them. Watch them smile. Notice how you feel.

Compliment someone on a job well done. Help them see what makes them special. Watch them smile. Notice how you feel. Then do it again and again.

Those good feelings are contagious. They motivate us to do more. They align us with what it means to be human - connected, compassionate, and alive.

And it helps. You’ll feel better. More loving. More hopeful. More human.

Will it make all the world’s troubles go away and make your angst disappear? No. It won’t. I wish it would. We can’t just ignore the afflictions of others. We all need to be part of the solution to the world’s woes. I hope my actions will create a ripple effect encouraging others to do the same.

Each of us must choose our own path. I have friends who have quit high-paying corporate jobs to become teachers or taken considerable pay cuts to work for nonprofits whose work they passionately support. Other friends are working at the grassroots level to elect leaders whose values reflect their own, and to protest against the injustices they see in the world.

None of us can fix the whole world. Each of us can be a light in the small corner that we are lucky enough to inhabit.

Until our next conversation,

David

Small Steps & Worthy Questions

• Avoid looking at the news until you have been awake for several hours. Notice how you feel compared to your usual routine.

• What’s something you are worried about that’s beyond your influence? Can you let it go, even a little?

• Find a way to take action on a cause you care about.

• Compliment someone today—make it specific and genuine.

• Take a quiet walk and name three good things you see or feel.

• Call or write a short note to someone who’s struggling or been on your mind.

• Think about whether you are living in alignment with the values you most admire? Where are you out of step?

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From the moment my daughter was born, I felt an intense desire to care for her, protect her, and guide her. When my son arrived two and a half years later, the same flood of emotion returned—to love, to protect, to guide.

It didn’t take long to encounter the parent’s conundrum. Like all young children, mine would cry when they didn’t get what they wanted. Their tears pulled at my heart. When they misbehaved, I got irritated and wanted to show them who was boss.

Still, a voice inside reminded me: my job wasn’t to make my kids happy in the moment, nor was it to dominate them. It was to help them grow into adults living lives filled with love, meaning, and joy.

That lofty goal isn’t easy amid the chaos of life. I needed a system—something to move me from knee-jerk reactions to values-based decision making.

Over time, I developed three child-rearing principles to guide me.

1. Tell Your Kids, Again and Again, How Much You Love Them

Growing up, my parents didn’t say “I love you.” I knew they loved me—they showed it—but it wasn’t spoken. Then, during my freshman year of college, I heard my roommate tell his folks, “I love you, Mom and Dad.” At first, I was shocked. Then, I started saying it too—and my parents reciprocated, for the rest of their lives.

I wanted my kids to know, beyond any doubt, how much I loved them. I constantly told them. Even when they protested, they knew I loved them unabashedly and was in their corner.

A parent’s affection is as close as it comes to unconditional love between humans. Many adults believe they have to earn love. Done right, parental love shows children that they are inherently lovable, inherently valuable. It is their birthright.

2. Help Them Be All They Can Be

Your job as a parent is to help your children grow into their full potential—and support them in building lives filled with love, meaning, and joy. It’s a big job, full of nuance.

To help them live life fully, I tried to give my kids the freedom to make their own choices and learn from their mistakes, while also protecting them from decisions that might cause lasting harm. It’s hard to strike that balance. I often wanted to step in. I imagined their missteps leading to catastrophe.

I’m a third-generation college graduate, and my kids always knew they were expected to earn a degree. Education is a core Geller family value. Thirty days before the application deadline for many colleges, I asked my son how his applications were going.

He replied: “I haven’t started.”

My stomach dropped. My mind started to race. Would he ever go to college? Would he lose out on job opportunities? How would he learn to think, reason, and argue persuasively? So many of my closest friendships were formed in college. Where would he find those precious lifelong relationships?

And, honestly, I worried what others would think of me. Would friends and colleagues see me as a failure? A dad whose son didn’t even apply to college?

I wanted to force him to sit down and complete the applications right away. But I didn’t.

He was 18. This was his journey. If he missed the deadline, maybe he wasn’t ready to go to college. He could get a job, or do a gap-year program. Both of which would give him the chance to experience new things, learn about life, grow and mature.

People take many paths. His path didn’t need to match mine.

I held my tongue. Instead of trying to impose my will on him, I simply offered to help him in any way I could.

One week before the deadline, he told me he was ready. He asked me to help him think through the essays. The next day, he worked on his applications from early morning until midnight. I hung out with him for the day, and periodically we had fun together batting around different essay ideas. Thankfully, he submitted five completed college applications just before the deadline.

The next fall, he attended a small liberal arts college and had a great experience. I’m glad he went. But I also know that his life would not have been ruined if he’d missed the deadline. It just would have been different. Maybe better in some ways, maybe worse.

I’m proud of how I learned to let go and support him in doing things his own way. Because that is what adults do. They figure out how to do the things they need to do in their own way.

3. They Get Upset With You–So What?!

As my kids grew, I felt the pull to be their friend. Most of the time, I resisted.

My job wasn’t to avoid conflict or win their approval, or to make my life easier. My job was to do what was best for them.

Still, it wasn’t easy. During my kids’ high school years, they would make requests that seemed crazy to me. There was the time my son became furious when I said his steady girlfriend could not spend the night in his room. I was patient, I listened carefully to his rationale, then explained myself. He retorted that all of his friends’ parents permitted such romantic sleepovers.

I said simply, “I love you more.”

He was angry; I felt sad about the distance this created between us. I soothed myself with the knowledge that I was doing what was best for my son.

Every decision has trade-offs. Eventually, I relinquished my unrealistic desire to be a perfect parent. I had to learn to make the best choice I could with the information I had.

My three principles helped me make better decisions. Not perfect, but better. I accepted that mistakes were inevitable. What mattered was showing up with love, intention, and responsibility.

These principles grounded me even when I was flooded by emotion. They were a reminder of how I wanted to parent–from a place of love, a desire to help my kids flourish, and a duty to put their needs above my own.

Until our next conversation,

David

Small Steps & Worthy Questions

• Let your children know how much you love them, again and again. If you don’t feel like you’re overdoing it, you’re not doing it enough!

• Your job is to do what is best for your child, not what makes them happy in the moment. Inevitably some of your decisions will upset them. Remind yourself it’s OK they are upset. They’ll get over it.

• When your child is struggling, ask yourself, “Do they need help, or space to grow?” Remember the power of active listening even when you’re tempted to offer solutions.

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There are perils to using artificial intelligence (AI) for wealth management. I discussed some of these drawbacks in my previous blog. But that doesn’t mean AI is of no use in this arena.

As of today, AI can’t replace your wealth manager - but it can enhance your relationship in ways that empower you to make better decisions and communicate more effectively with everyone impacted by those decisions.

That may sound like a big promise. How can AI do that?

• AI can help you communicate better with your wealth manager about the topics that matter most to you.

• AI can provide a second opinion on elements of your strategy, such as your portfolio or estate plan, giving you a springboard for a more robust conversation with your advisor.

• AI can help you understand complex financial topics that form the foundation of your financial plan, making discussions with your financial advisor more productive.

• AI can help you broach sensitive financial conversations with clarity and grace.

The best way to appreciate AI’s power is to go ahead and give it a try. I encourage you to experiment with some of your own specifics. I have created a profile of a couple whose challenges resemble many of the clients I counseled in my 30 years as a wealth manager.

Greg Baker is 62 and his wife, Sharon, is 50. They’ve been married 15 years. Each has two children from a prior marriage. Greg’s children are in their 30s, married, with three kids under age 5. Sharon’s children are single in their early 20s.

Greg and Sharon want to retire sooner rather than later, but they’re nervous about having enough money. They own a $750,000 paid-for home, hold $2.5 million in retirement accounts, $100,000 in a Health Savings Account, and $1.5 million in a taxable investment account. Their advisor has them invested in a globally diversified portfolio - 65% equities, 35% cash and U.S. Treasuries - almost entirely in low-cost exchange-traded funds (ETFs). They anticipate needing $15,000 a month to live their retirement dream.

Most of their accounts are in Greg’s name; he has been the primary wealth accumulator. Sharon comes from an affluent family. Her 85-year-old father has told her she’ll receive a “sizable inheritance.” She’s reluctant to ask him how much.

I plugged Greg and Sharon’s situation into AI and asked a series of questions. Overall, the answers were remarkably well considered and helpful. If you want to see more than the summary of my findings, you can click the associated links to read the full text of the AI responses.

Preparing for a Wealth Manager Meeting

Bakers’ Question:

We’re about to meet with our financial advisor. We want to know if our portfolio is suitable for people like us, hoping to retire within five years. We don’t even know what questions to ask. We don’t trust a second opinion, because we fear another advisor will just tell us what we want to hear to get our business.

AI’s Answer:

AI generated thoughtful questions to help the Bakers clarify their retirement goals - essential for any financial projection. It also suggested questions to ask their advisor about retirement income and investment strategies. AI even offered to run independent projections and stress tests.

The problem? Based on mistakes I have uncovered in previous experiments, I wouldn’t be confident in AI’s projections just yet. But the questions themselves were excellent. (You can read the AI’s full response here)

Obtaining a Second Opinion

Bakers’ Question:

We would like to retire sooner rather than later, and certainly no later than five years from now. What is a suitable portfolio for us? We understand that time, not money, is our scarcest resource, and we are willing to cut our expenses to $12,000 a month if it means we can retire sooner. Knowing that we can live on less, does it change your portfolio recommendations for us?

AI’s Answer:

AI offered a reasonable second opinion. It noted that a lower spending target improves their odds of retiring early. It suggested a more conservative allocation, listed specific low-cost ETFs, and highlighted some tax-saving strategies.

Would I recommend following AI’s portfolio recommendation directly? No. AI’s portfolio is a good start, and like all portfolios, has advantages and disadvantages. But it’s an excellent starting point for a thoughtful conversation with their advisor.

Understanding a Complex Topic

Bakers’ Question:

We’re worried about growing old and not having enough money for care. We’ve considered long-term care insurance, but it’s very expensive. Do we have enough savings to cover costs on our own? Are there alternatives? Please review our options and recommend a solution.

AI’s Answer:

AI helped them frame the issue. It noted that 70% of people over 65 will need long-term care, usually for fewer than five years. It showed the Bakers they could likely cover the need from their assets, though an extended need might strain resources. It reviewed two insurance options, outlined pros and cons, explored other funding sources, and made a specific recommendation.

AI’s recommendation gave the Bakers a structured way to engage their advisor in a meaningful discussion on this complicated issue. (Click here to see the detailed breakdown from the AI.)

Tackling a Sensitive Discussion

Sharon Baker’s Question:

My dad told me I’ll receive a “sizable inheritance,” but I don’t know what that means. Can you help me figure out how to ask the amount without sounding greedy? Knowing this information would help Greg and I plan our future.

AI’s Answer:

AI crafted emotionally intelligent scripts for Sharon. One framed the conversation around responsibility and estate planning. Another took a more direct - but emotionally riskier - approach. It even drafted potential responses from her father and ways Sharon could reply. It considered the pros and cons of different approaches, and recommended how she should proceed.

In short, AI helped Sharon prepare for a sensitive, high-stakes conversation with thoughtfulness and tact. (See the exact scripts and conversation paths the AI suggested in the full document.)

The Bottom Line

AI is not yet ready to replace your financial advisor. But it is an incredibly powerful tool that can help you:

• ask sharper questions

• weigh tradeoffs

• explore complex topics

• handle delicate conversations

Used wisely, AI can make you a better partner to your advisor - and a better steward of your wealth.

Have you used AI to help make financial decisions or enhance conversations with your advisor? I’d love to hear your experience - the good, the bad, and the ugly.

Until our next conversation,

David

Small Steps & Worthy Questions

• Am I open to using new tools like AI to challenge assumptions and uncover blind spots in my financial planning?

• What topics in my financial life feel too complex or intimidating, and could AI help me unpack them?

• How could AI make my conversations with my spouse, family, or advisor more productive? Test AI’s ability by experimenting with scripting a sensitive money conversation with a family member.

• Use AI to draft three questions for your next meeting with your wealth manager.

• Run a “second opinion” check on one element of your financial plan—and bring the results to your advisor for review.

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How can we tap into the power of AI to manage our financial wealth in a way that leads to a more meaningful, joyful, and fulfilling life? Over the past couple of months, I have been experimenting to see what it can and can’t do.

I used ChatGPT, a computer program that simulates human conversation and can be accessed through a web browser or via apps. I thought AI would deliver precise math models but provide stiff and off-kilter recommendations for emotionally nuanced situations. To my surprise, the opposite often happened.

What follows is my advice based on what AI can do today - not what it might do tomorrow.

Don’t Use AI for Financial Projections

I tested AI’s ability to run projections on retirement and college savings. It seemed like the kind of task AI would excel at—just give it the right inputs and let it crunch the numbers.

That’s not what happened.

Sometimes the answers were correct. Other times, they were wrong—wildly wrong. And they were always delivered with a tone of absolute certainty.

As a wealth manager for many years, I have a deep understanding of how financial projections work and clients learned they could depend on my knowledge. But without that training, you’d have no way of knowing whether AI’s projections are reliable.

Don’t Rely on AI Alone for Financial Advice

AI-generated financial advice is often problematic. Sometimes it’s needlessly complex and confusing. Sometimes it’s correct but incomplete.

Let me illustrate with a fictional example of a retired couple, both of them 70. They have a paid-off home, Social Security income, and a $3 million portfolio—$2 million in traditional IRAs and $1 million in a taxable account split among highly appreciated equity index funds, bond funds with almost no gains, and money markets.

They decide to give their son $200,000 for the down payment on a home. I asked AI where’s the best place among their investments to pull the money from. AI gave a tax-sensitive response: pull from the cash and bonds in the taxable account to avoid income taxes and capital gains taxes.

That sounds good, until you realize the response gave no consideration to the couple’s portfolio’s structure. Draining their cash and bonds could leave the couple exposed, potentially forcing them to sell stocks during a downturn to meet living expenses.

Worse, AI added unnecessary complexity. It raised concerns about federal gift and estate taxes—even though this couple’s nest egg is nowhere near the thresholds where those taxes apply.

AI Doesn’t Consider the Big Picture

When clients asked me tactical questions, like how best to withdraw $200,000 from their portfolio, I’d zoom out first. How does this decision fit into the broader picture of their lives?

If this couple had called me, I would have reminded them they recently started spending $3,000 a month to support the wife’s aging parents, and they have complained about feeling financially stretched. From my perspective, they have three important and competing goals: their lifestyle and travel plans, supporting her parents, and helping their son buy a home. Giving their son $200,000 leaves considerably less money to support her parents or take that dream vacation.

My counsel would be that they need to figure out which of these three goals matters most to them. We would work through together how much money they need to set aside for each goal. After this analysis, they might still give their son the same amount, or maybe decide half as much or even nothing was more appropriate.

Those are nuances that depend on the give and take of human conversation.

AI will answer the question you ask. It won’t help you figure out the question you should be asking.

AI’s Advice May Not Be in Your Best Interest

Suppose you ask AI whether to withdraw the $200,000 for the son’s house or borrow against your investment portfolio. It might recommend a loan to avoid triggering capital gains taxes. That could be wise—or a mistake—depending on your comfort with debt, the loan’s interest rate, your available collateral, and whether you have capital loss carryforwards.

What you won’t know is whether AI is programmed to subtly steer you toward a margin loan because it’s more profitable for the brokerage firm.

You Can’t Intuit AI’s Intentions

Exceptional wealth management is a human-to-human relationship. It’s built on trust, care, competence, and nonjudgmental listening. A great advisor puts your interests first—and you can feel it.

If your advisor starts giving self-serving advice, you are likely to notice. They’ll look uneasy. Their answers will feel off. You’ll get a gut sense that something’s wrong.

With AI, those subtle warning signs don’t exist. There’s no unease to detect. No facial expression. No body language. AI has no emotions, no soul, no loyalty. It’s a tool programmed by people—and those people may or may not have your best interests at heart.

Big companies are investing heavily in AI. It’s reasonable to expect that many will design AI tools that give advice aligned with their profit motives.

Proceed with Caution

I want to emphasize that, in time, developers will solve some of the issues I highlight above, and new challenges will emerge.

Although I am sounding a warning about misleading or just plain wrong outcomes, I do not doubt that AI offers benefits for your wealth management needs. It can help you engage in more productive conversations with your advisor, better understand your investment plans, and even communicate with family around sensitive financial issues.

All of that will be the focus of my next blog.

Until our next conversation,

David

Small Steps & Worthy Questions

Have you ever trusted a tool—technological or otherwise—only to realize later that what you really needed was wisdom, not just information?

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Wealth & Fulfillment is a passion project. I feel called to write it after spending nearly my entire adult life in the wealth management world—and coming to terms with how common misconceptions about money leave a trail of anguish in many people’s lives.

I love writing from the heart, challenging our culture’s assumptions about money, success, and what makes life worth living. It’s very satisfying to me to express in words what I have learned from decades in business and many encounters with clients.

I enjoy examining the powerful, sometimes insidious, role money plays in our lives. Writing helps me live more intentionally. It’s also my attempt to leave a legacy of wisdom for my children and grandchildren, ready for them to find when the time is right.

I hope you see your own experience in mine. I hope this blog nudges you to consider how to use your wealth to build a more loving and satisfying life.

I was a business owner for nearly 30 years. Early on, I learned to pay close attention to numbers: revenue, expenses, client growth, and retention. These metrics helped my brother and me build a profitable business that could withstand hard times.

Old habits die hard.

Recently, I noticed that same business mindset creeping into how I think about the blog. I began paying too much attention to subscriber counts and growth trends. I found myself wondering: Should I write more about technical wealth management? Should I avoid topics that might upset some people?

I started thinking of the blog as a little business, with subscriber growth as my new profit metric.

But that’s not what this is. Wealth & Fulfillment is not a business. It generates no revenue. Subscriptions are free. I’m not looking to land speaking gigs or launch a coaching practice.

I write this blog for myself, for my family, and for anyone who may find it useful.

Yet, almost without noticing, my old business instincts began shaping my writing.

I started drafting blog posts that I thought would attract more subscribers, instead of writing from the heart. The result? The drafts felt hollow—more like posturing than sharing. Honestly, they were crap.

How did I realize this? I noticed how I felt. Writing those drafts left me empty, frustrated, even angry. What was upsetting me? I sat with my feelings and gave some thought to what was going on.

I got quiet, listening carefully to the part of me that’s raw, emotional, unguarded. Eventually, I heard the answer. I was putting pragmatic business concerns ahead of a deep desire to communicate my own truth. And then it clicked. This isn’t a business–it’s a passion project!

The second half of life isn’t about performance or achievement - it’s about emotional wisdom. It’s about listening to the small, honest voice inside—the one that knows what you love, what gives you peace, and what breaks your heart. It’s not about what the world wants from you. It’s about what your soul longs for.

I’ve been given an extraordinary gift—the physical, intellectual, spiritual, and financial freedom to live life on my own terms. But if I want to use this gift wisely, I need to stay close to what brings me joy, peace, and purpose. I need to listen to what breaks my heart—and what heals it.

These aren’t questions for the intellect. They’re questions for the heart. AI can’t answer them. Neither can spreadsheets. They require stillness, vulnerability, and trust.

I’m a thinker. I like to analyze problems and find the best solution. My wife often reminds me that I’m thinking all the time. It’s definitely one of my signature strengths. But thinking is not the path to discovering my emotional truth.

To access it, I rely on practices like meditation, prayer, therapy, journaling, listening to music, and walking in silence.

If you struggle with accessing your emotions, I don’t know what will work for you. But I encourage you to start somewhere. Take a small step. And if you get stuck, consider working with a therapist.

As for me, I’m stepping away from thinking about blog metrics. I don’t want to relapse into old patterns of using numbers to measure success. I’ve asked my son-in-law, who manages the blog’s social media, to keep an eye on growth and give me occasional updates. That way, I stay connected—but not consumed.

Until our next conversation,

David

Small Steps & Worthy Questions

1. Take five quiet minutes and ask yourself: What do I long for right now? Don’t judge the answer—just listen. You may have to do this a few times before learning anything. Be patient.

2. If you used your inner wisdom to guide your actions for one day, what would you do differently?

3. Keep a journal for one week noting how different activities make you feel—fulfilled, drained, peaceful, or restless?

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In high school, I had a close friend from a very wealthy family. His parents both drove Mercedes-Benz cars. Their house was huge and impeccably decorated. They took cool vacations to Europe.

I thought he had it made.

I believed the key to a great life was having enough money to do what you wanted, when you wanted, and how you wanted.

That mindset fueled my desire to work really hard so I could earn a lot of money. I wanted to live that life of luxury.

As my income grew, I put that theory to the test. My wife Heidi and I flew first class, stayed in five-star hotels, dined at Michelin-star restaurants, drove expensive cars, and bought a beautiful home. At first, it all felt amazing. But over time, the good feelings began to fade. I’d been chasing an illusion. Turns out, having enough money to live luxuriously is not the key to living a wonderful life. When that realization hit me, I felt a wave of disappointment, frustration, and sadness.

I understand why I got confused in high school. I was too young to know better. Why didn’t I figure out sooner that the relentless pursuit of luxury inevitably leads to heartache?

The joy of the luxury experience is powerful.

• That first stay at a five-star beach resort? Incredible.

• The fifth time? You start noticing the little things that aren’t perfect.

• By the tenth? You’re researching upgrades.

Psychologists call this hedonic adaptation. Our brains are wired to normalize what once felt extraordinary.

Soon, the exceptional becomes expected.

So where does that leave Heidi and me? Should we live like monks? Absolutely not. I worked too hard, for too long, not to enjoy the money we saved. But I have learned to think about spending differently.

Here are some of the lessons I learned.

Mix It Up

Pleasure fades when it becomes routine. So now, we mix it up. We still stay in beautiful places—but not every time. Sometimes we choose simpler hotels or fly coach. Oddly, those moments enhance our enjoyment of the splurges. Luxury isn’t luxurious when it’s constant. It’s the contrast that restores the magic.

Share the Pleasure

Nothing reinvigorates an experience like sharing it with someone who’s never had it. Last year, we rented a 60-foot sailboat with a captain and cook and invited three close friends who had never sailed before. We loved our week together. Seeing it all through their eyes made it feel new again. Even better, it felt deeply fulfilling to treat them to an experience they may never have chosen for themselves—and to show, in a tangible way, how much we love them.

Savoring is powerful

The more I slow down, the more I enjoy. One of my favorite trips was when Heidi and I rented a small apartment in Paris. Instead of rushing from must-see spot to must-see spot, we walked, wandered, and lived more like locals. The less we planned, and the more we allowed ourselves to savor, the richer the experience became.

Pause Before Purchasing

Whatever I own, owns me. A bigger house might be beautiful—but it comes with more maintenance, more decisions, more responsibility. If your goal is freedom, ownership can get in the way. Before I buy something now, I ask: Would renting give me the same joy with less stress? Often, the answer is yes. Not always—but often.

Spend on Personal Growth

One of the best decisions I’ve made in recent years was enrolling in a one-year fellowship focused on mindfulness and spiritual growth. It wasn’t cheap—in time or money. But it was life-changing. Spending on personal growth brings a kind of satisfaction that doesn’t fade. If anything, it deepens. Want to disrupt hedonic adaptation? Grow. Stretch. Evolve.

Heal a Small Corner of the World

When luxury fades and growth feels slow, giving has a way of grounding you. Not giving from obligation—giving from connection. Find a nonprofit doing work that you care about. Learn what they need. Offer your time, your skills, your perspective. Then give targeted gifts that help solve real problems. It’s not about being a hero. It’s about being useful. It’s about knowing that your money, wisdom, effort really matter.

You Have to Try Stuff

None of this comes easily. The options are vast. The path isn’t always clear. You’ll try things that don’t work. You’ll spend money on experiences that fall flat. That’s okay. The point isn’t to get it perfect. The point is to keep learning—about yourself, your values, and what brings you alive.

For me, this is the heart of fulfillment: Spending money in ways that align with who I am, what I care about, and the life I want to lead. It’s not about denial, it’s about design. Designing a life where money isn’t just spent—but well-spent.

Where joy lasts a little longer.

Where meaning doesn’t fade.

Where you look around and think, this is what I worked for.

Until our next conversation,

David

A Note on the Image: The art of Kintsugi is a Japanese practice of mending what's broken with gold. It's a reminder that our healing and past experiences don't need to be hidden; they can become a beautiful and strong part of our story.

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Our 7-year-old granddaughter, Olivia, is a Girl Scout for the first time, and cookie season had arrived. When my wife, Heidi, and I were visiting recently on a Sunday afternoon, Olivia asked,

“Poppy and Savta (the Hebrew word for grandmother), would you buy some Girl Scout cookies?”

“Absolutely,” I said. “We would love to buy 90 boxes.”

At $6 a box, I had just committed to purchasing $540 worth of cookies. My daughter, Rachel, looked at me with a mix of bewilderment and irritation. She replied:

“Over my dead body! Olivia is not going to be someone who wins the prize because she has a grandfather who spoils her. Absolutely not.”

I replied, “What if I told you that we want to take Olivia with us as we deliver 30 boxes each to the Atlanta Food Bank and two charities that serve the homeless? My hope is that Olivia will start to understand how fortunate our family is—and that helping others is a Geller family value.”

Rachel said, “If that’s the plan, you can buy the 90 boxes.”

Heidi and I are grandparents, not parents. Our role is to support our children as they raise their own kids. Although our intention—to donate the cookies to charity—was carefully considered, I should have discussed the plan with Rachel before making the offer. She may have had different ideas about how to use the Girl Scout cookie experience to benefit Olivia. Without her consent, I risked derailing her approach, undermining her authority, or putting Rachel and her husband, Felipe, in an awkward position.

Fortunately, Rachel wasn’t shy about setting a boundary. And once she understood our motive, she embraced the plan. Still, the experience reminded me that even with the best intentions, communication and consent matter.

Our outing with Olivia to deliver the cookies went well. She saw firsthand that some families struggle to get enough food, and that some children don’t have a safe place to sleep. At one shelter, she drew a picture and taped it to the wall of a couple’s room, hoping to brighten their day. She got a small taste of what it feels like to make a difference.

One experience won’t be enough, of course. Like all of us, Olivia lives in a culture that falsely teaches that our responsibility ends with our own family—and that happiness is found in what money can buy. If those messages go unchallenged, they can take root.

This cookie outing was just one step in a lifelong process. We modeled a belief that all people are precious—that all people matter. As grandparents, Heidi and I—with the blessing of her parents—want to reinforce the message that being part of our family means using our time, money, and talents to help others. We showed Olivia that generosity is a Geller family value that spans generations.

Working together with Rachel and Felipe, Heidi and I play an important role in helping to raise Olivia and her younger sister, Hailey. Knowing that multiple people love you and care for you is a good thing. Rachel and Felipe lead busy lives—juggling work, home, and parenting. We help fill in the gaps. We care for our grandchildren regularly, giving their parents a much-needed break.

And our initial disagreement over buying 90 boxes gave Olivia something else: exposure to a model for navigating conflict. She is learning that family disagreements are a normal part of life. When they arise, she sees her parents and grandparents resolving them with candor, respect, and love. She begins to understand that it’s okay to disagree—and that love is never in doubt.

What started as a simple idea to buy cookies from my granddaughter and give them to those in need turned into a life lesson not just for Olivia but also for me. Family is at the center of my life, as it is for most of us. And family is complicated.

Until our next conversation,

David

Small Steps & Worthy Questions

1. Do you let your children know that you recognize they are in charge of their kids? Ask if there’s anything they’d like you to do differently next time you babysit. Give some thought to how you can be supportive without interfering.

2. When disagreements arise with your adult children, respond with curiosity, not control. Listen first instead of leading with your opinion. Maybe even take some time to consider their perspective before you respond.

3. Identify three family values you hope to pass on. Choose one and take a small action this week to reinforce it. Do you model your values for the next generation?

4. Involve your grandchildren in age-appropriate acts of generosity: donating food, helping a neighbor, contributing money for people in need.

5. Write a short note to your children or grandchildren expressing what you admire in them. It can go a long way.

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Until recently, my morning routine consisted of taking out my adorable, fluffy, white dog Sophie, making a great cup of coffee, and watching the news. Almost always, I became agitated. I find much of what is going on in the world disturbing. I was left feeling sad and helpless.

What a crazy way to start the day! I was focusing my attention on things I don’t like and can’t control.

Once agitated, it’s hard for me to settle down. For the rest of the day, I found myself becoming frustrated and irritated more readily.

Clearly, I needed a new morning routine that set the stage for better outcomes. It took me a while to figure it out.

This is something I experiment with, and what works for me may not work for you.

I also have learned that my routine needs to be adjusted to reflect my frequently changing life, hopes, and concerns.

Sophie still needs to go outside and I still need my coffee. Then on most days, I spend about an hour in meditation and prayer. I love to listen to some beloved Jewish prayers, set to music. I make it a point to focus on gratitude. I remind myself I have the freedom to choose how I live my life. I think about how to use my time, talents, and wisdom to make a positive difference. I ask for peace and healing for myself, the people I love, and the world.

I usually end my session with a simple breath meditation. I hope those 10 minutes of breathing will give the prayers time to sink into my soul before the day’s activities distract me.

On other days, I try to pause, be still, and sense into myself what I need today. The answers are widely varied. I go for a walk in the neighborhood, or read something inspirational, or listen to music, or write in my journal, or sip my coffee on the porch while looking at the trees and listening to the birds. I try to follow my instincts, and avoid being rigid about it.

There is no one-size-fits-all routine despite what’s recommended on social media. I’m a practicing Jew, and your faith tradition may differ, or perhaps you find inspiration and encouragement outside of traditional prayer and practice. I expect it will take you some time to figure out what works for you. What I wanted was a morning routine that cultivates a sense of gratitude and empowerment. A routine that helps me live in the present, shift my focus to that which is within my sphere of influence or control. I want to be reminded that:

Try a variety of things, and expect that some will not be useful. Just get started.

• Sit in silence for five minutes, an hour, or anything in between.

• Go for a walk in nature or around the block.

• Take a yoga class, go for an early morning run, or find an exercise class you’ve been wanting to try.

• Begin a regular gratitude practice.

• Listen to music that leaves you feeling good.

• Read an inspirational book. (If you can’t find one you like, feel free to reach out to me for suggestions.)

• Grab a cup of coffee with a friend. Instead of talking about the news, catch up on what is going on in each other’s life.

Since switching my own routine, I am feeling less anxious, less agitated, and less overwhelmed. I am more likely to accept the things I cannot change, and to remind myself that today’s challenges often provide the fuel that leads to tomorrow’s progress.

More importantly, I am much more likely to do what I can to make the world a bit better. To greet people with a smile, to listen to others with curiosity and compassion, and to engage in small acts of random kindness.

Until our next conversation,

David

Small Steps & Worthy Questions

1. How is your morning routine working for you? Have you reconsidered recently what parts are helpful and which may be harmful?

2. What are a few things for which you are grateful? Experiment with focusing on the gifts in your life for a few moments each day. Does it improve your experience of life?

3. How might you take a small step to shift your focus from things outside your control to those within your control?

4. Much of the news leaves me feeling terrible about the state of the world. I understand democracies depend on the civic engagement of informed citizens. How do I fulfill my civic duty and maintain my equanimity? Please let me know your thoughts on how you are coping with this question, and any others this blog provokes. I’d love to hear from you.

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