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The Reinvention Playbook: A Speaker’s Guide on How to Build a Speaking Career that Matters

Every year, I speak with countless people who feel a pull toward something more. They are talented professionals, often succeeding on the corporate ladder, but they have a message to share and a desire to use their voice as a tool for transformation. They want to become a speaker, an author, a coach—but the path from a stable nine-to-five to the center stage can feel confusing, uncertain, and challenging.

They often ask for tips on delivery or how to find gigs, but the truth is, building a sustainable career as a speaker is a dual journey. It’s about simultaneously mastering the Reinvention Engine—the strategic, long-term work of building a new career—and the Mastery of the Craft—the tactical, on-stage work of connecting with an audience.

I know this journey intimately because I’ve walked it. My path wasn’t a straight line. It was a series of calculated pivots: from a great corporate sales job at Ingersoll Rand to becoming an inner-city high school math teacher, and eventually to the portfolio career I have today, writing books, teaching at universities, coaching executives, and speaking to audiences around the world.

This guide is the playbook I wish I had when I started. It combines the two critical paths—reinvention and mastery—that you must walk to build a career and a life that truly matters.

Part 1: The Reinvention Engine – Building Your Career Brick by Brick

Before you can worry about what you’ll say on stage, you have to build the platform to stand on. This is the slow, often unglamorous work that happens behind the scenes, and it’s the most critical part of a successful transition.

The Myth of “More Time” and the Power of “Drops in the Bucket”

The most common trap I see aspiring speakers fall into is waiting for the “perfect time” to start. They believe they’ll pursue their passion when they have more time, but I’ve learned a paradoxical truth: we are often more productive when we have less time, and when we finally get more time, we don’t always do the things we thought we would.

The solution is to stop waiting to fill the bucket all at once. Instead, add one single drop, every single day. This “drops in the bucket” principle is about the power of small, consistent actions that compound over time. You don’t need to quit your job to start. You can:

• Join Toastmasters and practice giving speeches every week.
• Start a YouTube channel and record short, 10-minute “mini-keynotes” on topics that matter to you.
• Write three blog posts a week on your subject of expertise.

These daily drops feel insignificant in the moment, but over a few years, they will fill a bucket so heavy with expertise, content, and credibility that your transition will feel less like a leap and more like a natural next step.

The Calculated Leap, Not the Reckless Jump

When the time does come to make a bigger move, it shouldn’t feel like a scary leap into the unknown. It should be a well-planned launch. When I decided to leave my corporate sales job—a fun job where I sold beer coolers to Anheuser Busch and went to Super Bowl parties—I was facing about $100,000 in student loan debt. Jumping without a plan would have been a disaster.

Instead, I took a calculated risk. I called my banks and restructured my student loan debt to lower the monthly payments, knowing it meant paying more interest over time. I cashed in my 401(k), giving me enough money to survive for about 10 months without a full-time job. And I was willing to do whatever it took to make ends meet while I pursued my passion for teaching; I worked at a mall folding shirts, I tutored, and I even worked for a musician, setting up his gigs. It took four years from the day I quit to the day I got my first full-time classroom teaching job. Reinvention requires a plan and the humility to hustle.

Document Everything: Turn Gigs into Assets

One of my biggest professional regrets is not documenting my early speaking career properly. If I could do it all over again, the one thing I would change is this: I would have hired my own photographer for my early gigs, even the unpaid ones.

Here’s why: a photo or video clip of you on stage is not a memory; it’s a career asset. Those pictures and clips are what will get you the next, higher-paying gig. When you’re starting out, a portfolio of high-quality assets is more valuable than a small speaking fee.

This can even become a point of negotiation. When I had the opportunity to speak at the World Bank, I knew the fee would be lower than my standard rate, but the prestige was immense. So, as part of the deal, I asked them to instruct their in-house photographer to capture a lot of pictures of me while I was on stage. Those photos were worth far more than the difference in the fee because they served as powerful proof for future clients.

Part 2: The Mastery of the Craft – Connecting From the Stage

Once you start getting opportunities, the focus shifts from building the career to mastering the craft. A powerful speaker does more than just deliver information; they create an experience. It all starts with defining who you want to be on stage.

It All Starts With Identity

When I first spoke with Chase, an aspiring MC, he was looking for tips. But before we got into tactics, I asked him to describe his dream public speaking performance. He envisioned himself on stage at a comic convention, and through that visualization, we uncovered his three core goals as a speaker: to energize people, to make them feel safe, and to give them a goal for the event.

This is the most important first step. Before you write a single word of your talk, you must define your intention. What do you want the audience to feel? Once you know your identity as a speaker, every choice you make—from how you move to the stories you tell—will serve that purpose.

Creating Energy: Motion Creates Emotion

The easiest way to put an audience to sleep is to stand perfectly still behind a podium. If you want to energize a room, you must move. Motion creates emotion. The physical energy of the speaker is contagious.

To do this effectively:

• Ditch the Podium: Use it only to hold your notes, but don’t hide behind it. Stand center stage with a wireless lavalier mic so your hands are free and your whole body is visible.
• Use the Whole Stage: Walk from one side of the stage to the other. This simple act forces the audience to turn their heads and physically follow you, which keeps them from dozing off or looking at their phones.
• Come Off the Stage: My favorite technique for creating energy is to come off the stage and walk through the aisles. I’ll lock eyes with someone as I’m making a point, and suddenly the entire room feels electric. They’re no longer watching a speech; they’re part of an experience.

Building Trust: Show, Don’t Tell

Trust is the currency of a speaker. Without it, your message is meaningless. The mistake most speakers make is trying to tell the audience to trust them. They’ll say things like, “This is a safe space”. But these are just words, and an audience has no reason to believe a stranger on a stage.

You must show them, and the most powerful way to do that is through vulnerable, personal stories. Instead of just telling people a space is safe, tell them a story about a time you were scared and found safety in a similar event or community.

When I talk about creating safe learning environments, I share a rule I had in my math classroom: if a student raised their hand and got a question wrong, they got a high-five or a fist bump. Getting it right earned them nothing. Why? Because I wanted to reward the courage to try over the pressure of being correct. I tell the story of my most timid student, who was terrified of math, and the day she finally started raising her hand with confidence. That story shows what a safe space looks like far more powerfully than any command. Combine that with making real, direct eye contact with people in the audience, and you build a foundation of genuine trust.

Delivering with Intention: Internalize, Don’t Memorize

The number one fear for new speakers is forgetting their lines. This fear leads them to the trap of rote memorization. But a memorized speech sounds robotic and is incredibly fragile; if you get thrown off by an interruption, it’s nearly impossible to find your place again.

The professional’s goal is not to memorize the script, but to internalize the message. The technique is simple but requires discipline: read your script, from start to finish, at least 50 times. Practice it standing up, simulating the real thing. When you’ve gone through it that many times, the message becomes a part of you. You can deliver it with flexibility, passion, and authenticity.

I learned a valuable lesson from the ballet world: if you make a mistake on stage, you just continue on as if nothing happened. 99% of the audience will never know. Never apologize for a mistake on stage; it breaks the audience’s concentration and shatters the connection you’ve worked so hard to build. Internalize your message, and you’ll have the confidence to navigate any moment with grace.

The Journey Is the Destination

Building a career as a speaker isn’t about a single viral talk or a lucky break. It’s about the disciplined, daily work of building your platform and the courageous, on-stage act of connecting with other human beings. It’s the daily “drops in the bucket” that build your career and the vulnerable stories that build your craft.

The path isn’t easy, but it is one of the most rewarding journeys you can take. Your voice is a tool for transformation, and the world is waiting to hear what you have to say!