Episode summary

To celebrate the launch of darrinpeppard.com, Darrin shares six quotes that have shaped his leadership—and how each one connects to clarity, systems, purpose, relationships, and the courage to take the road less traveled. Along the way, he shares pivotal stories: moving from “Captain Chaos” to intentional leader, the coaching that changed everything, trusting relationships over titles, and choosing the Road to Awesome.

The six quotes & themes

1. “Clear is kind.” — Brené Brown → Clarity is respect; clear expectations build trust and culture.
2. “You don’t rise to the level of your goals, you fall to the level of your systems.” — James Clear → Systems create freedom; move from reactive to proactive.
3. “We are uniquely positioned to help the person we once were.” — Rory Vaden → Why Darrin coaches overwhelmed leaders: he was one.
4. “People don’t buy what you do; they buy why you do it.” — Simon Sinek → Purpose drives followership; leadership begins with why.
5. “The quality of your leadership is reflected in the quality of your relationships.” — John C. Maxwell → Leadership is a people business; trust is the measure.
6. “Two roads diverged… I took the one less traveled…” — Robert Frost → Courage to choose the harder, truer path—the Road to Awesome.

Key moments & stories

• Early lesson: tough conversations and the kindness of clarity.
• From big goals/small systems to calendar discipline and true prioritization.
• Coaching that shifted Darrin from firefighter to leader.
• Purpose as the anchor for speaking, coaching, and the new site.
• A critic turned ally: trust as leadership’s true metric.
• Three “two-roads” inflection points: focusing on what’s right, leader vs. firefighter, and the leap into entrepreneurship.

Timestamps (approx.)

00:00 — Welcome & website launch celebration

02:40 — Quote 1: Clear is kind

05:30 — Quote 2: Goals vs. systems

09:10 — Quote 3: Helping the leader I once was

14:40 — Quote 4: People buy your why

18:00 — Quote 5: Relationships mirror leadership

22:10 — Quote 6: The road less traveled

27:10 — Call to action & close

Resources & links

• Explore the new site: darrinpeppard.com
• Grab the free AWESOME Leadership Action Guide (link in show notes)
• Speaking, coaching, and workshops: inquire via the site’s contact page

Call to action

If you’re ready to move from chaos to clarity and lead with intention, visit darrinpeppard.com and download the FREE AWESOME Leadership Action Guide. Book Darrin for your next keynote, retreat, or leadership team training.

Hey everybody, welcome into episode 241 of the Leaning Into Leadership podcast. Today's episode is a special one. And honestly, it feels a little bit like a celebration. It's not only that we are stepping into this new chapter at Road to Awesome, but we have just launched a brand new website, darrenpepper.com. And I'm so excited about it. It's been live for just over 24 hours and

today on the show, just want to share for you just a little bit of the journey. It's been amazing. This journey itself has been like probably many of the roads that I've traveled before in that there have been twists and turns. There have been some lessons along the way, some interesting lessons to say the least. Certainly there have been some moments of frustration, but also some great

moments of clarity as I have made my way on this journey. So today, the way I want to go about this episode is sharing something that's at the heart of the journey. And not just the journey of this next big step in Road to Awesome, but truly my Road to Awesome journey. And I want to do that by sharing six quotes that I have been profoundly impacted by.

Words that have genuinely shaped my leadership. Words that have guided me through uncertain times, through challenging times. Words that have helped me to find clarity when things were really chaotic. Words that have reminded me of the kind of leader that I want to be each and every day. As I go through each one of them, I'll share with you how it connects to the work here at Road to Awesome and

through darrenpepper.com. I'll share how that individual quote, each of them as I go through, connects to my philosophy as a leader, to the work I do as a leadership speaker, as an author, the work I do with leadership training, with leadership teams, my leadership coaching, all of those pieces and how that has led to this next step of helping leaders from

every walk of life. Find clarity, be intentional, and walk in their purpose.

To me, that's what this is all about. So with that, let's dive right in to this episode.

All right, here we go. Quote number one from Brene Brown, clear as kind. We hear this one all the time. But when I first heard it, when I first read it actually, because that was the first time that I came across these words, it stopped me in my tracks. I thought for a long time as a leader, and I know a lot of other leaders have struggled with this, but I thought being kind meant

maybe sanding the edges off of the truth. Yeah, I remember early in my principalship, I would sit down to be part of one of those tough conversations. And I wanted everybody to the table happy. You know, I mean, sometimes I just like danced around the real issue, hoping that it would go and fix itself. If I alluded to what needed to change or what needed to be done, yeah, that would take care of it.

Spoiler alert, it never did.

One day, I had to let a staff member go. Man, I was dreading it. I was not looking forward to that conversation. But I learned something prior to that conversation. And the reality is this, clarity isn't cruelty. In fact, clarity is a form of respect. When you go into those conversations, being direct

staying focused on the facts and being crystal clear.

That is a form of respect.

When we're clear about our expectations, when we're clear about feedback, when we're clear about our purpose, we give people a gift.

we eliminate confusion. That's the gift. We let them know where they stand. We let them know where we stand. We let them know truly what it is that we're expecting of them and what they can expect from us.

That to me is why clarity became one of the cornerstones of my leadership and now all the work that I do. Because clear expectations build trust. Trust builds culture.

So when I say clear as kind, I'm not just quoting Brene Brown, I'm reminding myself and every leader I work with, kindness isn't about avoiding discomfort. It's about communicating with courage. That's the foundation of what you're gonna find on the new website. Resources and tools, opportunities to connect that help leaders with clarity and with intention.

Quote number two, you don't rise to the level of your goals. You fall to the level of your systems. James Clear. man, when I first read Atomic Habits, and I've read it, I don't know, a dozen times at this point, but man, that first time, and I read this quote, I felt exposed. I'm not kidding. I felt so exposed. I'm like, my gosh.

I mean, if I'm being honest, I used to be like big goals, little systems kind of guy and not on purpose. And I didn't even think I knew that's what I was doing, but it was all about big goals. And I was the idea guy. And I put people around me who were good at, you know, putting things in place. But the truth is your systems are what will be the difference between success and a lack of success.

Again, I was this guy who had these huge visions for our school. New programs, new initiatives, better culture, but really no system, consistent system, consistent process to make those things happen. I was what my team affectionately called Captain Chaos because I start each day with good intentions and then end up just chasing fires and missing out on the real work.

You've heard me talk about it here on the podcast. I was living in superhero syndrome.

Everything changed when I learned how to build systems that was genuinely designed to support my goals.

One of the biggest shifts for me, I've talked about it here on the show before, but when I gave my secretary full access to my calendar, full access to my email, she managed both of them with such great intention. She was incredible at scheduling priorities, not just appointments. All of a sudden, I wasn't reacting day to day. I was a proactive leader showing up.

Amazing. It's incredible when you lean into systems, what they can do. Just that one system alone became this incredible amount of freedom for me.

See, here's the thing for non-systems thinkers, and I'm one. I have to force myself. I have to force myself to put systems in place. And if I don't...

I'm gonna struggle.

But so often people think systems are about restriction. But they're not. They're about creating consistency around the things that matter most.

I mean, that's why I created the course, Take Control of Your Leadership. That's why I have put things together like the awesome Leadership Action Guide, brand new guide, by the way. Down in the show notes, hit the link, it's yours for free. But a brand new guide, the awesome Leadership Action Guide. All about systems. When you build your systems intentionally around the things that you have gained clarity around.

the things that you truly hold important, the things that you truly want to focus on, you give yourself and you give your team the structure to actually achieve your goals. But without systems, you're not going to achieve your goals. Quote number three, we are uniquely positioned to help the person we once were. Incredibly wise words.

from Rory Vaden. The first time I heard Rory Vaden say this, he was on a podcast, and I don't remember whose it was, but I've rewound it probably five times.

I was like, yes, because this quote is my story. I mean, remember, I was the guy years ago who was just this totally overwhelmed principal. I was just buried under the weight of every problem, everything happening in my school. I was running from fire to fire to fire to fire, crisis to crisis to crisis to crisis. And the reality is

They weren't even my crises. They weren't even my fires. Man, I was trying to do it all by myself.

I had assistant principals who I guarantee resented me because I sure as hell resented them because they weren't doing anything. Truth was that was my fault, not theirs. It wasn't like they didn't want to work. That was on me, not on them. Reality is I wasn't leading. I was barely managing. And honestly, I was so unbelievably exhausted.

We got a new superintendent and he came in and he told us every single leader in the district that he was going to hire a leadership coach for each and every one of us. I wasn't really sure what coaching was about, but while my peers resented this superintendent hiring coaches saying, I don't need a coach. How dare he hire a coach for me.

I was grateful because I knew that I was struggling. And the truth is working with my coach changed everything. He helped me see the difference between activity, between like busy work, between checking boxes and actually making an impact as a leader. He helped me find clarity. He helped me build systems. He helped me create space where I can actually lead instead of just

run around from crisis to crisis. And here's the thing, that experience didn't just make me a better leader. It lit a fire in me.

Because I realized once I got it kind of figured out that I was now uniquely positioned to help the person I once was. That overwhelmed leader. You don't have to just be a principal. mean, leadership is leadership. It doesn't matter what walk of life you're in. Maybe you're leading a healthcare team. Maybe you're leading a marketing team. Maybe you're part of...

a construction site and you are the general contractor and it's your job to lead the whole team. That's no different than what I experienced as a high school principal. If all you're doing is running around trying to do everything, you're not leading with clarity.

But again, I realized that I am now uniquely positioned to help you, that overwhelmed leader, regardless what role you hold. I am uniquely positioned to help you because I was that leader. That's honestly why Roe Dawson exists. To help leaders get their footing back. To help move you from being reactive to proactive. From chaos to clarity.

and from exhaustion and burnout to genuinely walking in your purpose. Every time I work with a whether I'm speaking to them through keynotes, I'm directly coaching them, leading a workshop for their team.

I see my former self. I see that leader who's struggling to catch their breath. And I remember how powerful it is when somebody walks beside you and helps you find your way. You see, here's the thing about Roe Dawson. I am not the hero of the story. You are the hero of the story. I'm just your guide. That's why this quote is so important to me.

I am the guy to help you find your road to awesome. I already found mine. I want to help you find your road to awesome.

Quote number four.

People don't buy what you do, they buy why you do it. Simon Sinek. This is all about purpose. And by the way, just, I'll just say this upfront. And I can only speak specifically to the education audience here, but I have a feeling this is true in other walks. We have mutilated and bastardized this phrase to the point where people are turned off when you say, find your why, know your why.

That's not why I'm talking about this. That is 100 % not why I'm talking about this. Because I'm tired of hearing that too. Because that's not what Simon Sinek was talking about. The very first time I saw his Ted Talk about the Golden Circle.

I realized something super, super important.

And it's not about the why inside of you. I mean, it is, but more importantly, it's about as a leader, people don't follow a title. They don't follow a program. They don't follow an initiative. I follow a human being that's driven by purpose.

If you're clear about your purpose, if you know genuinely my purpose is to do this, whatever this might be, that's why people follow you. I as a principal, my purpose was always about helping people discover their greatness. We started using Road to Awesome when I was a high school principal. It was all about helping everybody find their road to awesome, whether that's a student, a teacher, a parent.

Anyone. Doesn't matter. Now, a speaker, as a coach, that hasn't changed. It's just expanded. It's gotten bigger. Now, with the new DarrenPepper.com and me stepping into that corporate space wanting to help people with all types of leadership work, it's just gotten bigger.

I want to help you find your purpose. I want to help you walk in your purpose. That's why I say that.

Whether I'm on stage or I'm in a coaching session or I'm behind this microphone right here, my purpose is to help leaders find clarity, to be intentional, to live in a space of confidence, and to remind them that leadership doesn't have to feel like chaos. It doesn't have to be overwhelming.

When leaders are clear about their purpose, their why, if you will, it's the only time I'll say it. I stopped chasing everything. I start leading with focus, with purpose, dialed in on what really matters and what they genuinely care about.

That's why DarrenPepper.com is not just a website. It's a platform built around helping leaders find their purpose. Every keynote, every workshop, every resource starts with purpose. And that, to me, is where true leadership begins.

You like that one? I barely talked about quote the why, because we've gotten away from what it really means. And what I just talked about is what he really meant.

Quote number five, the quality of your leadership is reflected in the quality of your relationships. John Maxwell. man, does this one hit home. Leadership at its core is a people business, period. It's not about programs, it's not about policies, it's about people. As a leader, you lead people, period. That's one of the hardest things about leadership, right? Because you were really good at whatever it was.

being a classroom teacher, being the HVAC installation guy, being the person who was building copy for this marketing agency. But then they tapped you on the shoulder and they said, hey, you need to be a leader. We need you to lead the department. We need you to lead the school. We need you to lead the crew.

And that's not about what that work was. It's all about people. Man, I'll never forget a moment, really late in my principalship. Man, there was a teacher who'd been one of my toughest critics. And for years, we butted heads.

Over time, we had some pretty honest conversations.

some interesting exchanges, I But there were also some things that created small steps of trust. And things began to change. We weren't building the greatest of relationships, but because I was willing to listen to her and she was willing to listen to me, because I was intentional about going and setting time aside to ask her opinion.

things started to change.

One day she stopped me in the hallway.

And just absolutely out of the air, she said, you know, I really wasn't sure about you when they hired you as the principal.

But you know what? I trust you. I really feel like we're moving in the right direction. And then she went on her way.

I'll be honest with you, I started to cry. I ducked into a classroom real quick because I was starting to cry because she had been one of my biggest critics. And now in that moment saying, Darren, I trust you and we're going the right direction. That meant everything.

That moment was way more important to me, honestly, than any of the awards, any of the recognition, because leadership's not measured in titles. It's measured in trust. Again, people business. When people believe in you, they'll follow you. If your relationships are strong, your leadership is strong. If your relationships are fractured, your leadership's gonna struggle. That's kind of the core of

of the book Culture First Classrooms that I wrote with Katie Kinder. Really, it's the heart of everything I do. You can't fake relationships. You have to invest in them. You have to make people feel seen, heard, valued, and trusted. You've heard me say that dozens of times here on the show. That's not just a phrase. It's the truth. It's because leadership is people business. It's what builds great teams. It's what...

It's great companies. It's what builds great schools. It's what builds a great culture.

Leadership is a people business. Don't ever forget that.

All right, time for the sixth and final quote.

Two roads diverged in a wood and I, I took the road less traveled by and that has made all the difference. The incredible words of Robert Frost, the final stanza of his unbelievably famous poem, The Road Not Taken. If you've ever wondered where did Roe Dawson come from, that is exactly where it came from. That line from The Road Not Taken has guided me for years because, leadership,

at its best is about courage. It's about the courage to take the road less traveled. For me, it meant walking away from what was comfortable. It meant...

staying true to what you really believe in. Focusing on what really matters instead of what's easy.

The interesting thing there, two huge, probably three huge, two road moments for me, where the two roads diverged for me. First and foremost, the culture moment, when I was in assistant principal, somebody asked, Darren, why does it always have to be about what they do wrong? Why can't it be about what they do right? Boom, two roads. Ooh, two roads. Why does it always have to be about what they do wrong?

Let's focus on what they do right. Hey, you know what? That's the road less traveled, but we're going to take it. It's the road to awesome.

Two roads, mama number two.

First day my leadership coach was on campus with me. Chaos around me. Insane, insane start to a day. It was a Monday.

I finally caught up to him a couple hours into my day. He was in a classroom, we stepped in the hallway. And he just asked me point blank, Darren, do you wanna be a firefighter do you wanna be a leader? Boom, two roads.

You can run around and be a firefighter all you want, just not being a leader.

But on this other road, this much more difficult road, the road where you find clarity, the road where you build systems, the road where you're intentional, that's the road to awesome. And that's where leaders go.

Two Roads Woman number three, shared it not too long ago on the show.

late in my superintendency, my last year, before I made the decision to jump out into what I do now, to become an entrepreneur, to become a leadership speaker and coach and author.

to become a leadership expert.

sitting on the back porch with my wife, trying to decide what's next. Because I couldn't continue with what I was doing. And she said, you know, Darren, you tell people all the time, when two roads diverge, take the road to awesome. Why wouldn't you do that yourself? Here's your opportunity.

Go do what you were called to do. Two roads.

two roads.

I really didn't know what Rhoda Austin was going to become. I really didn't. I was terrified to be perfectly honest with you. But you know what? When your spouse looks you in the eye and says, believe in you, I know you can do this. And she has said to me so many times, so many times since we made this move, that she never had a doubt.

where we would go. Man, when you got that kind of support, just know, this is where I need to be. This is where I'm called to be. What I knew Road to Awesome could be.

was a new way of leading, a new way of living. And for people to stop settling for average. I if we're all traveling the road, why in the world would you take the road to average? Take the road to awesome.

Why? Why would you settle for average? Take the road to awesome. That's what this new chapter represents, to be perfectly honest with you. That's what it's about. That's what the launch of DarrenPepper.com is all about. It's not just a new website. It's not just a place for resources and a way to find me and a way to book me to speak. No. It's another avenue for me to continue to chase that fire that is raging inside of me.

That little tiny fire that was lit back when I finally figured out how to not be a firefighter as a building principal. When I fell in love with coaching aspiring leaders, when I fell in love with coaching my assistant principals, my department heads. Man, that fire is raging inside of me right now. That's what this chapter represents.

It represents simply that it isn't just about working with one group. This is about working with every leader I could possibly impact. Because, damn it, leaders deserve to have clarity. They deserve to be intentional and they deserve to walk in their purpose. It's that simple.

This is the continuity. This is a continuation. This is the next step on our road to awesome. So.

I'll close my sermon now. Six quotes, six reminders that leadership is about clarity, consistency, purpose, relationships, courage, and growth. Here they are again, clear as kind. You do not rise to your goals. You fall to your systems. We are uniquely positioned to help the person we once were.

People don't buy what you do. They buy why you do it. The quality of your relationship, sorry, the quality of your leadership is reflected by the quality of your relationships.

And finally, two roads diverged in a wood, and I took the road less traveled.

And that road less traveled, that is the road to awesome. Thank you so much for walking this journey with me, for listening, for watching, for learning and leading. And if you haven't yet, head over to the new DarrenPepper.com, explore the new site, grab the free awesome leadership action guide. There's a link down in the show notes as well for that. See how you can take the next step.

in your own awesome leadership journey. If you're looking for someone to bring the fire, bring the passion, and bring that leadership to your event, to your team, hey, let's have a conversation. Reach out. Let's get connected. As always, don't settle for average. Get out there and travel your road to awesome.

Thanks for joining me on the Leading Into Leadership podcast. Until next time.

Have a road to awesome day.