Today we’d like to introduce you to Tyler Skinner.
Hi Tyler, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
For as long as I can remember, I’ve been drawn to people and their stories. Looking back, my mom reminds me that I was always the one standing in front of a room—whether it was giving presentations in school, speaking at leadership conferences in college, or finding any excuse to bring people together. I didn’t know then that those moments were quietly preparing me for the work I do today.
My path hasn’t been linear. I’ve worn a lot of hats—marketing, community development, nonprofit leadership, entrepreneurship, and now speaking and executive advising. Every chapter taught me something, but the common thread was always the same: helping people see what’s possible in themselves and in each other.
One of the biggest lessons in my life has been learning to take a step before I felt ready.
That idea has shown up over and over again. It showed up when I studied abroad in Spain. It showed up when I started businesses without having everything figured out. It showed up when I built Women Making Waves, not because there was a perfect blueprint, but because I saw a need for women to have deeper conversations, stronger relationships, and spaces where they didn’t have to do life or leadership alone.
It even showed up 40 feet in the air on a flying trapeze.
Standing on that platform, every instinct told me to wait until I felt more confident. But confidence wasn’t coming first. The only way forward was to let go. That experience became a metaphor for so much of my life and eventually the foundation of my keynote talks. I’ve learned that fear isn’t usually a stop sign—it’s often an invitation. The moments that have changed my life weren’t the ones where I felt ready. They were the ones where I chose to trust myself anyway.
Today, I have the privilege of working with founders, executives, entrepreneurs, and women leaders as a speaker, facilitator, and advisor. Through Women Making Waves, my podcast Mishaps, Magic & Mayhem, and my leadership programs, I help people navigate change, build meaningful relationships, and lead with greater courage and intention.
If there’s one thing my journey has taught me, it’s this: we’re all standing at the edge of something. A decision. A dream. A new season. We spend so much time waiting to feel certain before we act, but certainty rarely comes first. Growth comes from taking the next step before you have all the answers.
Ironically, the net I spent years looking for became the community I eventually built.
That’s the work that excites me most today—creating spaces where people feel seen, challenged, and supported enough to take that next step, because I’ve learned that one courageous decision can change the entire direction of a life.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Not even close.
From the outside, people often see the speaking engagements, the businesses, the community, or the leadership work and assume there was some master plan. The reality is that my journey has been filled with uncertainty, pivots, and moments where I questioned whether I was on the right path.
One of my biggest struggles has actually been leaving behind things I was good at to pursue work that felt more meaningful. That’s much harder than most people realize. It’s one thing to start something new when what you’re doing isn’t working. It’s another to walk away from something that’s comfortable because you know you’re being called toward something greater.
I’ve also spent a lot of time waiting until I felt “ready.” Ready to speak. Ready to charge what I was worth. Ready to lead at a bigger level. Ready to put my ideas into the world.
Eventually I realized that “ready” isn’t a feeling that magically arrives. It’s something you build by taking action before you have all the answers.
Like many entrepreneurs, I’ve experienced seasons where I questioned everything—financial uncertainty, ideas that didn’t work the way I expected, projects that took far longer than planned, and the emotional weight that comes with leading while trying to take care of everyone else. There were moments when I wondered if I was building too many things or whether I should just choose the safer path.
What kept bringing me back was people.
Every time someone shared that one conversation changed how they saw themselves, or that they finally made the decision they’d been avoiding, it reminded me why this work matters.
Ironically, the hardest seasons became the foundation for what I teach today. I don’t speak because I’ve figured life out. I speak because I’ve stood at enough edges to know what it feels like to be afraid, and I’ve learned that courage isn’t the absence of fear—it’s choosing to move anyway.
I still face challenges. Every new level asks something different of me. But today I don’t see struggle as evidence that I’m on the wrong path. More often than not, it’s confirmation that I’m growing into the next version of who I’m meant to become.
We’ve been impressed with Tyler Skinner , but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
At its core, my work is about helping people navigate the moments that matter most.
Whether I’m standing on a stage, facilitating an executive leadership retreat, or sitting across from a founder during a strategy session, I’m helping people move through uncertainty with greater clarity, courage, and confidence.
I work with organizations, leadership teams, founders, and high-performing professionals who are standing at the edge of change. Sometimes that’s stepping into a bigger leadership role. Sometimes it’s building a healthier culture. Sometimes it’s making a decision they’ve been carrying for months. My job isn’t to give people all the answers—it’s to help them uncover the ones they already know are true.
I’m known for asking the questions most people avoid.
The conversations people often tell me they’ve been thinking about for years but have never said out loud.
I believe the biggest breakthroughs rarely happen because someone gave us a better strategy. They happen because someone created enough trust and enough space for us to finally see ourselves differently.
That’s what I strive to create.
My work blends leadership development, experiential learning, storytelling, and strategic advisory in a way that’s both practical and deeply human. Whether I’m leading a keynote, working with executive teams, facilitating immersive experiences, or advising entrepreneurs, my focus is always the same: helping people with momentum, not just motivation.
What I’m most proud of isn’t a particular achievement or title. It’s the reputation I’ve built for creating rooms where people feel safe enough to be honest, challenged enough to grow, and supported enough to take action. Those are the moments that change careers, businesses, and sometimes entire lives.
I don’t believe transformation comes from having everything figured out. I believe it comes from trusting yourself enough to take the next step before you feel completely ready.
If there’s one thing I hope people experience after working with me, it’s this: they leave with more confidence in themselves than when they arrived. Because when people trust themselves, they don’t just make better decisions—they become better leaders, better collaborators, and more intentional humans. That’s the ripple effect I’m committed to creating through everything I do.
Do you have any advice for those just starting out?
I wish someone had told me that you don’t have to feel ready before you begin.
For years, I thought confidence came first. I believed that someday I’d wake up feeling certain enough to take the leap, raise my hand, charge what I was worth, or share my voice on a bigger stage.
That day never came.
Instead, I discovered that confidence is built through action, not before it.
If you’re just starting out, don’t wait until everything is perfect. Don’t wait for the website to be flawless, the offer to be complete, or the timing to feel right. You’ll learn more by having one real conversation, serving one client, or saying yes to one opportunity than you ever will by endlessly preparing.
I’d also encourage people to spend less time trying to build a network and more time building genuine relationships. Some of the biggest opportunities in my life have come from people who knew me, trusted me, and believed in me—not because I had the perfect pitch, but because we’d invested in a real connection over time.
And finally, remember that your greatest differentiator isn’t your credentials or your résumé. It’s your story.
The moments you think disqualify you are often the very experiences that allow someone else to trust you. The conversations I have today, the stages I stand on, and the organizations I work with aren’t built on perfection. They’re built on being willing to share what I’ve learned while I was still learning it.
You don’t have to have it all figured out. You just have to be willing to take the next step.
Looking back, I realize that every meaningful opportunity in my life started the same way: making a move before I felt ready.
Contact Info:
- Website: https://www.thetylerskinner.com
- Instagram: @thetylerskinner
- LinkedIn: https://www.linkedin.com/in/tyler-skinner-ba3b78189/
- Youtube: https://www.youtube.com/channel/UC33jbrHHrdKnUMoUOiHIm7w
- Other: https://www.women-making-waves.com
