We’re excited to introduce you to the always interesting and insightful Diana Lee. We hope you’ll enjoy our conversation with Diana below.

Diana, thanks for taking the time to share your stories with us today We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.

I didn’t set out to build a business.

In early 2023, I had just finalized my divorce. I was a newly single mom, navigating a season of deep uncertainty—personally, emotionally, financially. My job felt unstable and soul-sucking. My identity had unraveled. I wasn’t chasing growth or some bold new vision—I just needed to breathe. To survive. To feel like myself again.

Around that same time, I opened ChatGPT for the first time. Not to build a brand. Not to create content. I just wanted help rewriting my resume.

But what happened next changed everything.

That simple action opened up a space where I could think out loud, ask hard questions, and reconnect with myself without judgment. I started using AI—not to replace my thinking, but to clarify it. It became a thought partner. A space to process what I couldn’t yet name. And it helped me start piecing together a new way forward.

I realized I could use AI to:

-Reflect on my lived experience—pharmacy, tech, corporate comms

-Rebuild my confidence and clarity

-Design systems that actually fit how I think, work, and create

-Reclaim my voice—after years of shrinking, shape-shifting, and performing

That’s when it clicked.

There were so many others—founders, creatives, leaders—going through transitions of their own. People with powerful voices and purpose-driven ideas… but who felt completely overwhelmed by AI or unsure how to use it in a way that still felt human.

That’s the gap I wanted to fill.

I didn’t want to teach people how to use a tool—I wanted to help them come back to themselves. To use AI with clarity, intention, and integrity.

The business came after. The clarity came first.

And the more I worked with people, the more I realized—this wasn’t just about digital strategy. It was about rebuilding identity. Creating systems that protect your energy. And using technology to support your voice, not drown it out.

That’s what I do now.

I help people turn chaos into clarity—using AI not to automate everything, but to reclaim their time, their voice, and their ability to lead with purpose.

And that never gets old.

Diana, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Sure. The short version?
I help people use AI to come back to themselves.

I’m a strategist, systems builder, and clarity partner for creatives, founders, and mission-driven leaders—especially those going through a season of transition. I specialize in voice-driven strategy, AI-powered workflows, and what I call “clarity systems”—the custom frameworks, tools, and language that help people finally feel seen, focused, and ready to move forward.

But I didn’t get here in a straight line.

My background spans pharmacy, military tech, and corporate communications—and I’ve always been someone who could see patterns in chaos, translate between systems and people, and turn overwhelming ideas into clear action.

Still, it wasn’t until I hit a major turning point in my life—going through divorce and becoming a single mom—that everything clicked. I opened ChatGPT in early 2023, not to build a business, but to rewrite my resume.

Instead, it helped me rewrite my life.

That one tool gave me a space to think, reflect, and create with intention. It gave me language for things I’d never been able to articulate. And slowly, I started to rebuild—not just my income, but my identity.

I used AI to reconnect all the parts of myself I had long compartmentalized:
-The systems thinker
-The deep feeler
-The nonlinear creator
-The woman who’s rebuilt more than once

From that process, I created the AI Clarity Playbook™—my signature offering. It’s a 1:1 strategy session where we distill your message, train ChatGPT to sound like you, and build a clarity system that supports how you actually work. Not what a formula tells you to do. Not what branding trends demand. But what feels honest, aligned, and sustainable.

That work has since evolved into my core offerings:

🌱 The AI Clarity Playbook™ – A 1-hour deep dive to map your voice, offers, and systems in a way that brings all the scattered pieces together

🌱 The Clarity Partnership – Ongoing, high-trust strategic support for founders and leaders navigating big decisions, pivots, or reinvention

What sets me apart?

I don’t just teach people how to “use AI.”
I help them build tools and systems that reflect who they really are—not who they think they have to be.

I work fast, but deeply.
I collapse months… years… of second-guessing into an hour of grounded clarity.
And I don’t just bring tech skills—I bring lived experience, emotional nuance, and real strategic depth.

What am I most proud of?

Honestly? That my work feels like me.
That I get to do it while raising two kids.
That I’ve rebuilt a life that’s rooted in truth—and now I help others do the same.

If you’re someone who’s in that in-between space—burned out, overwhelmed, scattered, or trying to find your voice again—I see you. I’ve been there. And I know how powerful it is to get the right support at the right time.

That’s what this work is about.

Not just building smarter.
But building truer.

Can you share a story from your journey that illustrates your resilience?

Two years ago, I was in full-on survival mode.

I had just finalized my divorce. I was a newly single mom. My job at the time felt unstable and soul-sucking, and my confidence was in the gutter. I wasn’t trying to launch something bold—I just needed to stay afloat. Pay the bills. Show up for my kids. Try to remember who I was after years of shrinking and shape-shifting in a life that no longer fit.

In the middle of that mess, I opened ChatGPT for the first time—just to rewrite my resume. But it ended up becoming something so much more.

It became a mirror.
A private space where I could think out loud, make sense of my experiences, and ask questions I wasn’t ready to ask anyone else.
It gave me language when I didn’t have any.
It gave me clarity when everything felt uncertain.

Little by little, I started rebuilding. I used AI to organize my thoughts, clarify what I stood for, and design systems that actually supported how I think and create. What began as a tool to “fix my resume” ended up helping me rebuild my life.

That season taught me something I’ll never forget:
Resilience isn’t just about pushing through.
It’s about making space to reimagine. To let go of what no longer fits.
And to rebuild something that feels like you—even when you’re still figuring out who that is.

That’s why I do the work I do now.
Because clarity is what carried me through the storm.
And now, I get to pass that clarity on to others.

One session, one system, one brave reimagining at a time.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I had to unlearn that being good at performing was the same thing as being safe.

For most of my life, I was praised for how adaptable I was. How well I could read the room. How quickly I could shift gears to meet expectations. Whether it was school, work, or relationships—I knew how to say the right thing. I knew how to be who people needed me to be.

But over time, I lost track of who I was underneath it all.

When I left my marriage and my job in the same season, it felt like the scaffolding that had been holding me up collapsed. The things I’d built my identity on—being dependable, being competent, being the strong one—no longer felt sustainable. And they certainly weren’t protecting me from burnout, heartbreak, or feeling like a ghost in my own life.

That’s when I realized:
Performing well doesn’t guarantee you’ll be seen.
It doesn’t guarantee you’ll be safe.
And it definitely doesn’t mean you’re living in alignment.

The unlearning happened slowly. It looked like:
— Saying “I don’t know” out loud, and not apologizing for it
— Letting silence be part of the conversation, instead of rushing to fill it
— Writing, creating, and building from a place of truth—not strategy
— Learning to ask: What do I actually want? instead of What do they expect from me?

And it’s still a practice. Every day.

But it’s also the reason I now help people rebuild their systems, strategies, and voice around who they really are—not who they think they need to be to succeed.

Because alignment is so much more sustainable than performance.

And the real safety?
That comes from being rooted in your truth.

Contact Info:

• Website: https://www.waggle.ai
• Linkedin: https://www.linkedin.com/in/dianaleeai/

Image Credits

Nichelle Bishop