P29: The Investment Portfolio You Didn't Know You Needed

Welcome to Just One Pivot, where we explore how a shift in perspective can change everything. If someone shared it with you, you can subscribe here.

Welcome back!

And if you are here for the first time, I’m thrilled you are here.

Quick question: How are you feeling about your investments these days?

Frankly, I’ve chosen purposeful ignorance. Don’t judge.

But one upside of the recent financial turbulence? It reminded me of an investment that continues to outperform.

One of my all-time, most profitable assets didn’t live in a brokerage account or on a plot of land. It was a story. Not just in having it, but in honing it and using it with intention.

This week, I invite you to see your stories, and your story portfolio, not as casual conversations or sentimental keepsakes but as strategic assets you own.

And I hope I can convince you that when crafted and practiced, they can make you the luckiest person in the room. And by luck, I mean this:

PIVOT POINT

The most impactful leaders don’t just tell. They show—through story.

And in case you're thinking, “What about showing through actions?” I’d argue that your actions are a story. The question is whether you’re shaping it with intention.

THE SHIFT

In 1997, I read a quote that rewired my thinking:

That quote changed everything I thought I knew about stories. I had just returned to college after a long break and began writing and rewriting a story for a scholarship application.

The $100K Story that Started It All

That was the opening line of my college application essay. I used it again and again to apply for scholarships and fellowships.

I imagined the people reading my application (my audience), sorting through stacks of students with identical stats.

So, instead of starting with achievements, I began with a moment: My father turning our guest room into a school because I said I wanted to be a teacher. A classroom of stuffed animals. My sister, one of my students, learning to read and write at age five.

That one story—simple, honest, vivid—opened doors.

It helped me earn enough scholarships to graduate with two degrees, debt-free. In today’s economy, that story is valued at over 100K.

PIVOT CHALLENGE

I want to challenge you to think of yourself as a Story Portfolio Steward—someone who increases the value of a living asset over time.

With this frame, storytelling isn’t just charm or entertainment.

It’s how you build trust, shape perception, and spark change. But only if you treat it like a craft and know the value of what you have in your hands.

How one story turned into a portfolio:

I had just launched my consulting practice and was preparing for a pitch. I knew I was the underdog. But I had just read Annette Simmons’ The Story Factor, and I was inspired to build my Signature Story Portfolio.

Instead of leading with tactics and frameworks, I opened with a piece of one story to make a point.

We were nearly out of time when one of the VPs leaned in and said, “Wait—you have to tell us what happened next!”

The pitch turned into a conversation. The conversation became a contract. That story opened the door.

Whether I’m writing a speech for a university president or working with leaders looking to expand their influence, I always start with a Signature Story Portfolio—developing six story types inspired by The Story Factor:

1. Who I Am Stories. Reveal your humanity and lived experience.

2. Why I’m Here Stories. Clarify your intentions.

3. Vision Stories. Help others see and feel the future.

4. Teaching Stories. Make ideas memorable and real.

5. Values in Action Stories. Show what matters most.

6. I Know What You’re Thinking Stories. Anticipate and disarm resistance.

These aren’t scripts. They’re connection points. They make your leadership more human and more credible.

If you want a deep dive on the evidence behind why Strategic Storytelling works, check out my longer article here.

Start with One

1. Choose One Story. Pick a signature moment that reveals who you are and what you stand for.

2. Know Your Audience. The story isn’t just about you; it’s about how you connect with the people in front of you.

3. Structure It. Begin with a hook, build the tension, resolve it clearly. Make sure there’s one clear takeaway (moral of the story).

4. Practice It. Deliver it. Ask for feedback. Refine. Repeat.

Of course there’s more to the craft, but mastery starts one small step repeated again and again over time. So start.

A FINAL WORD

When you become a steward of your stories, they become more than memories. They open doors. They build bridges. They multiply impact.

So, what will the ROI of your story be?

Let’s find out.

If this resonates, share this with someone who needs to hear the message.

Until next week,

P.S. I’m celebrating the ROI of a few stories! 🎉

Two of the stories I published on Medium are having a bit of a viral moment: over 7,000 reads since April 12. One of them, on the power of leading with curiosity, was cited in Medium’s global newsletter just yesterday.

But there’s more!

The connections have been the best part: senior leaders across industries are not only reading and resharing these stories on LinkedIn, we’re having virtual coffee conversations and exploring how The Structural Skills Project (the umbrella for these stories) aligns with their leadership goals and industry needs.

So far, I’ve connected with remarkable individuals from the U.S., UK, South Africa, France, Spain, and India—and early collaborations are already taking shape.

One story at a time.

Fall Calendar Now Open: I’m scheduling speaking and coaching engagements for the fall. If you have a group I can help inspire or want help building your Signature Story Portfolio, send me a note and let’s chat.

Note: Book links are affiliate links, which may support this issue at no cost to you.