This episode of A Good Pour was a little experiment.
Instead of our usual format, I let AI guide the conversation with Amy Gleaves. Amy was on the podcast back in June 2024, and so much has happened since then. So I uploaded the transcript from her last visit and asked AI to reflect back what it noticed about her growth.
What came out was thoughtful. Honest. Surprisingly accurate.
And honestly, it gave us language for things many of us feel but haven’t quite put into words yet.
This is Part 1 of our conversation because there was simply too much good here to rush.
Let’s start in the middle.
From Guide to Witness
AI summarized Amy’s shift this way: she’s moved from guide to witness.
Two years ago, Amy focused on helping people move forward. Now she speaks as someone who has walked through disruption herself. Divorce. Rebuilding. Identity shifts. Letting go. Beginning again.
She agreed with that description.
“I think everything I speak on, I’ve lived through.”
That’s what makes her work resonate. It’s not instruction from a distance. It’s lived experience. It’s someone standing in the middle and saying, “You’re not crazy. This part is hard. And you’re not alone.”
There’s credibility in that.
Speaking From the Middle, Not the Outcome
One of my favorite parts of this conversation was the idea of the middle.
Not the beginning.
Not the polished ending.
The middle.
Amy said something that stuck with me: we’re not chasing an outcome. We’re growing every single day.
So many of us want clarity before we move. We want the bow on top before we share the story. But Amy’s work now reflects something different. She’s willing to name the uncertainty while she’s in it. The grief. The rebuilding. The choice to keep showing up.
The middle is where the growth actually happens.
And maybe we don’t need to rush past it.
Confidence Rooted in Truth
Another shift AI noticed was this: Amy’s confidence used to sound like answers. Now it sounds like honesty.
That’s powerful.
She talked about how people used to say she made hard things look easy. But the truth is, they weren’t easy. She was just learning tools. Learning to sit with hard things instead of avoiding them.
Life is not 100 percent joy. It’s not 100 percent struggle either. It’s both.
The work isn’t to eliminate the hard. The work is to stay present when it shows up.
That’s a different kind of strength.
Who She Serves Best
When we talk about marketing at Good Circle Marketing, we talk about knowing who you help and how you help them.
Amy’s work has become clearer over time. She primarily serves women in transition. Women rebuilding. Women shifting identity. Women asking bigger questions about who they are becoming.
She still coaches men. She loves coaching men. But she knows who most naturally resonates with her message.
And there’s freedom in that.
You don’t have to serve everyone.
You don’t have to dilute your voice.
You can trust that the right people will lean in.
Rest vs Avoidance
We had a really honest moment about rest.
When is rest healthy?
And when is it avoidance?
Amy said something that hit home. Rest is an action when it’s intentional. But sometimes we call something “rest” when we’re really avoiding the uncomfortable thing in front of us.
Her personal example was powerful. During a busy season of moving houses and preparing for her daughter’s wedding, she gave herself a 7 p.m. cutoff every night. She planned her rest. She protected her energy. She didn’t wait until she was burned out.
Rest wasn’t accidental. It was chosen.
That’s accountability.
And she believes accountability starts with ourselves. The people we admire most in business and in life are accountable to themselves. They do the hard work, even when no one is watching.
Self-Trust Over Self-Improvement
This might be my favorite theme from Part 1.
Amy’s work has shifted from self-improvement to self-trust.
Earlier in her career, growth meant action. Now it also means listening. Honoring internal signals. Choosing alignment over performance.
She said something so simple and so profound: a lack of action is still action. It just might not be aligned action.
We are always doing something. The question is whether it’s moving us toward who we want to become.
Self-trust changes everything. When you trust yourself, you’re not afraid to take a day off. You’re not afraid to say no to a client who isn’t a good fit. You’re not afraid to try something new and not love it the first time.
You trust that you’ll get up tomorrow and keep going.
Good Work Is Becoming, Not Fixing
I asked AI to reflect specifically on good work.
It responded that Amy now treats good work as becoming, not fixing.
That stopped me in my tracks.
So many people come to coaching feeling broken. Not enough. Behind.
Amy pushes back on that. She believes who you are right now is worthy. The season you’re in, even if it feels unresolved, is shaping you.
You don’t have to wait until you “arrive” to begin.
You don’t have to fix yourself to do good work.
You start where you are.
This was only the first half of our conversation. In Part 2, we’ll continue unpacking growth, alignment, and what it looks like to trust yourself when the next step isn’t obvious.
For now, here’s what I’ll leave you with:
- You’re allowed to be in the middle.
- Rest can be strategic.
- Accountability starts with you.
- You don’t have to be fixed to be valuable.
You’re becoming.
And that’s good work.
If this resonated, share it with a friend who’s walking through transition. And if you haven’t yet, go listen to Amy’s podcast, Unquiet You. It’s thoughtful. Honest. And exactly the kind of conversation we need more of.
Part 2 coming soon.