Have you ever known exactly how you felt about someone — but when the moment came to say it out loud, the words disappeared?

In this episode of THEE BIG SWING, I sit down with a listener for a deeply honest conversation about love, timing, regret, and the emotional cost of silence.

She reflects on a moment when someone she cared about expressed how they felt — and although she felt the same way, she could not say it back. Not because the feelings weren’t there, but because fear, outside advice, past hurt, and the desire not to look foolish got in the way.

What follows is a conversation about the space between what we feel and what we are able to express. It is also a reflection on how other people’s opinions can shape our choices, especially when we are inexperienced, wounded, or afraid to repeat old mistakes.

But this is not only a story about regret. It is also a story about care, friendship, emotional maturity, and the strange ways people can remain important in our lives even after romance changes form.

Inside this conversation:

• Why saying what we feel can be harder than feeling it
• How fear of looking foolish can silence honest emotion
• The danger of letting outside voices make intimate decisions for us
• Why timing matters in love
• How some relationships survive by becoming something different
• What it means to look back and finally say the words that were once withheld

Sometimes the biggest swing is not chasing love.

Sometimes it is having the courage to say what was true when the moment was still in front of you.

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THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

When Someone Doesn't See You

Being underestimated has a way of reaching past your growth and pulling out an older version of you. In this episode, I share what happened during a lunch conversation that triggered something I thought I'd moved past.

After someone questioned my credentials — and my character — I defended myself well. Too well. And when the euphoria wore off, I had to sit with what that said about me.

This isn't really about the man who doubted me. It's about the man who answered.

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THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

Some moments stay with you because they reveal something bigger underneath them.

After traveling across states for her grandson's birthday, a mother finds herself wrestling with something many people quietly feel — the lack of courtesy, gratitude, and emotional awareness that can exist even within families.

What begins as a conversation about a difficult weekend gradually turns into something deeper. Expectations between people. Feeling unappreciated after extending yourself. Boundaries with family. And the complicated truth behind the phrase unconditional love.

At one point she says: "It's not unconditional. I wanted something back."

A deeply honest conversation about family dynamics, emotional reciprocity, parenthood, and recalibrating how we show up for the people we love most.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

Two years ago, my son was sleeping in his car in Los Angeles…
working 80 hours a week, barely showering, just trying to survive. 

Today he’s in a different place. Not perfect. Not finished. But clear.

In this episode, we sit down as father and son and talk honestly about what changed - and what didn’t.

This isn’t really about trading.
It’s about discipline, frustration, identity, and the moment you’re forced to look at yourself and decide who you’re going to be.

Because sometimes the shift doesn’t happen all at once.
It happens quietly. And then everything feels different.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

I Watched Them Let Their Guard Down

She thought she had to do it alone. Four women in my life — all very different, all fiercely independent — believed the same thing.

They resisted help. They resisted anything unfamiliar or outside of themselves.

And then, one by one, something shifted.

This isn't really about AI. It's about the moment you realize you don't have to carry everything on your own anymore.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

Some of us are not alive when we're here...

This episode came from a moment I had recently—one I didn’t plan, but couldn’t ignore.

Sitting in a movie theater, I found myself thinking about something I’ve thought about many times before: the difference between the time I’ve lived… and the time I likely have left.

But this time, it stayed with me.

And what struck me most wasn’t just that time is limited.

It’s how different life can feel once you finally arrive at something real—and realize how long it took to get there.

For a long stretch of my life… I wasn’t really living. I was just getting through it.

In this episode, I reflect on what it feels like when something you’ve known for a long time… becomes something you can’t ignore—and the quiet realization that life moves faster than you think.

This isn’t advice.

Just something I’m seeing more clearly now.

And maybe it’s worth seeing a little earlier.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

I sat down with my sister — and what she shared stayed with me.

This is a story about self-doubt, survival, and what it really means to bet on yourself.

She talks about growing up in poverty, struggling to believe she was smart enough, and becoming a young mother while trying to find her way forward.

But she never stopped moving.

From cutting classes in high school to earning her degree, raising her children on her own, and building a life across eight states — her journey is not about perfection. It's about persistence.

One of the most powerful realizations in this conversation: she was willing to bet on herself. Just not all the way.

This episode is about growth, resilience, and the quiet decision to keep going — even when you don't fully believe in yourself yet.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

Before this happened, I trusted it more than I realized.

I'd been using ChatGPT for a while — leaning on it, valuing its responses, growing comfortable with it. And then one day, during a routine exchange, it made an assumption about who I was.

It assumed I was a white man.

I wasn't outraged. I was stunned. And then I started asking questions.

This episode is me working through what that moment revealed — about AI, about identity, about pattern recognition, and about what it means to trust a tool that fills in what it doesn't know with what it thinks it knows.

I called three people about this. Two of them told me not to talk about it publicly.

I decided to anyway.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

In 2017, Lloyd took an ancestry DNA test expecting no surprises.

I was wrong.

What followed was a journey — literally — to a small island in the Dutch Caribbean where his grandfather was born, to relatives he never knew existed, to birth certificates from the late 1800s, and to a quiet but profound decision: to stop seeing strangers as strangers.

This isn't a political conversation. It's a personal one. About what happens when biology makes something plain that you thought you already understood. About belonging on a larger scale than most of us allow ourselves to consider.

And about what it feels like to finally take your place in the world.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]

What if one unexpected conversation could change the way you learn, think, and approach the rest of your life?

In this episode of THE BIG SWING, Lloyd reflects on a summer evening in Washington Square Park, where a spontaneous conversation with a young professional introduced him to a new way of seeing artificial intelligence — not as something distant, technical, or only meant for younger generations, but as a powerful tool for learning, growth, and reinvention.

At 61, Lloyd remembers when computers first entered the classroom. Decades later, he finds himself using AI to think through trading, decision-making, personal challenges, creative projects, and everyday questions with a level of speed and depth he never expected.

This episode is not about chasing technology for the sake of technology.

It is about curiosity.
It is about refusing stagnation.
It is about being willing to learn something new at any age.

Lloyd shares how ChatGPT became a kind of 24/7 thinking partner — helping him organize ideas, sharpen decisions, rethink old habits, and access information in a way that made learning feel exponential.

Inside this episode:

• How one conversation in a park opened the door to a new way of learning
• Why AI can be especially valuable for people who still want to grow, build, and improve
• How technology can help reduce frustration and turn confusion into action
• Why curiosity matters more than age
• How AI reshaped Lloyd’s approach to trading, problem-solving, and self-reflection

This is an episode for anyone who has ever felt behind, overwhelmed by change, or unsure where to begin with new technology.

The invitation is simple:

Stay curious.
Stay open.
Keep learning.

Because sometimes the biggest swing is not a dramatic life decision.

Sometimes it begins with a question, a conversation, and the willingness to try something new.

Send us Fan Mail

THEE BIG SWING is a reflective podcast about the emotional reckonings and subtle internal recalibrations that change our trajectory over time — and the possibilities still available in life.

Each episode explores the moments when curiosity, courage, accountability, or reflection opens new ways of seeing ourselves and the world.

Through personal reflections and conversations, Lloyd explores changing identities, relationships, self-trust, and the quiet decisions that alter how we see ourselves over time.

THEE BIG SWING is for people who are quietly realizing they are not the same person anymore and that there are still choices left.

The biggest swing isn't always dramatic. Often, it's the shift inside that changes everything.

If something here stayed with you, you can reach me at [email protected]