Leadership doesn’t fall apart overnight. More often, it slowly drifts into a pattern that feels overwhelming, exhausting, and reactive.

In this solo episode, Darrin introduces The Cycle of Chaos—a framework that helps leaders name what they’re experiencing and begin interrupting the patterns that keep them stuck in survival mode.

Rather than offering quick fixes or productivity hacks, this episode invites reflection, clarity, and intentional leadership.

In this episode, you’ll hear about:

1. Why feeling busy doesn’t always mean you’re being effective
2. How constant reactivity increases cognitive load and erodes clarity
3. The five stages of the Cycle of Chaos:
4. Constant Reactivity
5. High Cognitive Load
6. Absence of Clarity
7. Overextension
8. Survival Mode Leadership
9. Why leaders stay stuck in the cycle—and why it’s not a failure
10. How clarity becomes the starting point for real change

This conversation is a reminder that leaders don’t need to work harder—they need to lead clearer.

Sponsors

This episode is brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm.

Additional support comes from DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems.

All right, everybody, welcome into episode 257 of the Leaning Into Leadership podcast. This is a special midweek edition, special solo edition of the podcast. And you know, as I'm sitting here recording this episode, I can pretty much guarantee that many of you that are listening are coming off of a day that felt really full. Not necessarily fulfilling, but full. You probably had an absolute jam-packed calendar.

I would bet your inbox is still overflowing. You probably put out a whole bunch of fires, solved a ton of problems, and answered a million questions. For that matter, you probably made a bunch of decisions. And yet, if you're honest with yourself, you ended your day thinking, man, I was busy all day, but I don't know if I actually worked on the work that makes a difference.

or for that matter the work that I showed up intending to do.

Before we go any further, let's take a moment to thank our partners who make our conversations here on the Leaning Into Leadership Show podcast. Fuck.

Before we go any further, let's just take a moment and thank our partners who make the conversations here on the Leaning Into Leadership podcast possible. This episode is brought to you by HeyTutor. One of the biggest drivers of chaos for school leaders is trying to meet students' needs without enough support in place. Now, when students struggle, teachers feel it. When teachers feel it, leaders feel it. We feel it emotionally, operationally, and strategically.

A HATE Tutor delivers customized, evidence-based, high-dosage math and ELA tutoring for K-12 school districts across the country. Their focus on in-person tutoring along with online options allows districts to meet students where they are while still staying aligned with state standards. Where HATE Tutor really stands apart is that they handle everything. They do the recruiting, the hiring, the training, and managing of the tutors. So districts don't...

have to add any more to their already full plate. Tutors work in small groups during school day or after school, and progress is tracked through an accessible dashboard so leaders and teachers can actually see results. If supporting students while reducing leadership overwhelm matters to you, I encourage you to learn more about HeyTutor and the work they're doing across the country. Hit the link down in the show notes or go to heytutor.com.

This episode is also sponsored by Digicoach. Another major contributor to the cycle of chaos is carrying too much instructional feedback and follow-up in your head. Walkthroughs happen, notes are taken, the good intentions are there, but sometimes the systems break down. Digicoach helps leaders capture real-time walkthrough data, provide meaningful bite-sized feedback, and track instructional trends over time without adding more work to your day.

Instead of relying on your memory or scattered notes, Digicoach creates clarity around what you're seeing, what your teachers need, and where coaching conversations should go next. And this matters because clarity and feedback builds trust, consistency builds growth, and strong systems reduce chaos. If you're looking for a way to be more present in classrooms while working smarter, not harder, Digicoach is absolutely worth checking out. Go to digicoach.com. and let them know you heard about them here on the Leaning Into Leadership podcast for special partner pricing. Once again, that's digicoach.com.

All right, folks, let's get into today's conversation. What I wanna share with you is a framework that helps leaders finally name the thing they're stuck in, and more importantly, gives them a path out of it. I call this the cycle of chaos. Before we go any further, let me say this clearly.

This is not a checklist. This is not about fixing yourself. It's not about blaming leaders. And more importantly, this is not leadership failure. This is a cycle of chaos, a pattern that I see with so many leaders. Again, not about blame, not about you're broken and let's fix everything. Just simply, this is about naming a cycle that many

well-intentioned, hard-working leaders unintentionally reinforce. And simply because no one ever taught them how to interrupt that cycle. As we walk through this today, I don't want you to listen to fix anything. I just want you to listen to recognize. Because once you can name it, you can change it. The cycle of chaos has five parts. And together they spell exactly what it feels like to lead when things get overwhelming.

C-H-A-O-S. Chaos. The cycle is almost always.

kicked off. The cycle almost always begins with constant re-atech. Good lord.

Let's start with C. The cycle always begins with constant reactivity. Wow, I'm really struggling with that. One more time.

Okay, let's start with C.

Let's start with C. The cycle almost always begins with constant reactivity. Your day is dictated to you, not by your priorities, but by your interruptions. Those could be emails, phone calls, unexpected meetings, or urgent issues that suddenly become your responsibility. You come in with a plan and within the first 20 minutes, poof, it's gone. Right, we've all lived that day.

Somewhere along the way, many leaders start believing this, if I can just respond faster, I'll catch up. But the truth is, reactivity doesn't create relief. It creates momentum in the wrong direction. So you have to ask yourself, right now, what drives your day? What are your priorities?

Are they the things that really matter to you or you end up being pulled away by everybody else's emergencies? We often call that firefighting. Running from one crisis to the next, almost never are they your own crisis. That is constant reactivity. And that leads to the second piece in the chaos cycle, H, high cognitive load.

This is the part of the cycle that doesn't always show up on the outside, but man does it consume you on the inside. You are holding everything in your head. Things you need to follow up on, decisions you haven't made yet, problems that you haven't had time to think through. These are the things that wake you up at 2.15 in the morning and your brain is just going and going and going and you cannot go back to sleep. You find yourself

by 230 with a cup of coffee in front of your computer.

When you are stuck in high cognitive load, nothing feels finished, nothing feels settled, the brain never shuts off. This is where good leaders start to burn out. And it's not because you don't care, it's not because you're ineffective, don't think that for a moment. It's just simply because you're carrying so much more in your brain than any one person ever should. So, pause for a moment, ask yourself.

What am I carrying right now that should not be living in my head?

That, that is that high cognitive load. It's all those things stuck in your brain that you have not had the time or the capacity to get taken care of. And it's that high cognitive load that almost always leads to the A in the cycle of chaos, which is absence of clarity.

The absence of clarity really comes down to this. When everything feels important, nothing is clear. Again, back to running from fire to fire to fire. When you have way too many initiatives, priorities blur. Those of you who listen to the show regularly will remember that at a point, I worked under someone who had 13 different initiatives going at the same time. Our priorities were completely blurred. We were totally unclear of where we were trying to go.

Absence of clarity also comes from not taking a step back. Because when you don't take a step back or get up on the balcony like I like to talk about, that's when you lose sight of what actually matters the most. When you do step up on the balcony, when you do spend that time taking a step back, that's when you can actually look at and think about what your true priorities are and how well are you managing them? What evidence do you have?

But lacking that step back, you really do lose sight of what matters. You get stuck in the weeds. That's the phrase sometimes that we'll use, is stuck in the weeds. Now let me say this, because this really sits at core of my work. This really sits at the number one thing I help leaders with.

The leaders that I work with are not unclear because they're lazy or because they don't want to be clear. Oftentimes they're unclear because they've never been given the time, the space, or the permission to just take a step back and think. Just in this last week, I began work with another group of leaders, a team that

I had met a couple of times, but it was the first time I was on site with them. And the time I was on site with them this past week truly was chaos. 100%, all five pieces of the chaos cycle alive and well.

It's not that they don't want to be stuck in this. They just don't know. And we're going to have a follow-up conversation from that visit about all five pieces of the chaos theory and how it was alive and well. But the reality is, up until this point, they haven't been given the space or even the ability to name what it is that they're dealing with.

Maybe you're there, maybe you're not, but here's a really powerful question you could consider. If somebody asked you to name your top one or two priorities in your current leadership role.

Could you? Could you really say, and not just say these are my priorities, but are you actually doing them? Are you actually working on them? And what if I ask your leadership team the exact same question? Would they answer the same way as you? It's always a good way to look at it, right? It's that lack of clarity that really, really is a struggle. And it leads to the O in chaos, the fourth piece of the cycle of chaos, which is overextension.

This is where essentially you end up in kind of a bottleneck. You're doing the work of others, the work that other people could do. One of my favorite questions to ask leaders that I work with, you know, why are you doing this? Is there somebody else who could be doing this? Because so many leaders end up doing things that really don't fit into what they should be doing, work that they could delegate.

end up answering questions that people should be answering for themselves because they've become so dependent on someone else that they don't think independently, they don't take risk, they don't allow themselves to be empowered in the role that they're in.

Essentially as a leader when you're in that space, you are a fixer. You're not a developer. And in many ways, you're not a leader.

It's not servant leadership, by the way. I know some of you are thinking, well, but Darren, that's servant leadership, right? I mean, as a servant leader, I'm going to do for others. I'm going to tell you this right now. Servant leadership is about empowering others to do for themselves. It is not about doing everything for them. That is not servant leadership.

There's another piece with that. A lot of times, leaders will justify that. They will say, well, it's just faster if I do it myself. Maybe it is today. But what's faster in the moment is exhausting in the long run. Yeah, maybe you could do it once and it would be quicker. But what if you taught others or empowered others to do it for themselves? How much time does that free up for you to do the work that really matters?

I'm just saying.

just saying. That is overextension. And overextension does not make you a better leader. It just makes you tired. It just wears you out. It just feeds this entire cycle of chaos.

So, just think about this one. If this is an area where you feel like, yeah, he's probably talking about me right here, then ask yourself, where are some places that you're over-functioning? In other words, where are you doing things for others that they could do for themselves? And that takes me to the S in the cycle of chaos, which is survival mode leadership. This is where your leadership is really more about endurance.

It's about making it to Friday or making it to the next break or making it through one more week. If you find yourself thinking that, know, man, if I can just get to the next break, then, you know, I can work the whole break and maybe I'll get caught up. I was guilty of this all the time. You know, I would say things like, you know, man, when, when everybody's gone at, at, at the holiday break and that's two weeks of, I get more work done in two weeks and I get done in two months.

Well yeah, because you don't have a whole lot of other people asking you to do things for them. You get to do your work. That is survival mode leadership. And the thing is, when you're in that particular mode, there's not a lot of reflection that happens. You you're not taking the time to go and get up on the balcony and think about, you know, what evidence do I have that I'm actually working on what matters. There's also very little joy in your job. It's not like you love your job in those moments. But the worst piece...

is that there's almost no strategic thinking. You're not thinking six months or a year down the road. You're thinking tomorrow. You're thinking end of week. That's not a way to lead right there. That's management. You have to have the time to take that step back. We talked about that in a previous one. You have to have that time to get on the balcony and talk about it all the time. But if you don't have that time to be a strategic leader,

We're not really leading.

We're just getting by. Survival mode leadership.

Here's the other piece. This is not why you got into the work. You did not sit in the hot seat interviewing for the role that you're in thinking, man, I just can't wait to just get by. No, you were thinking, how can I make this the best school, best district, best construction company, best.

Fill in the blank, right?

That's what you were thinking when you sat in the hot seat. You didn't get into the role you're in to just get by. You got into the role because you saw other leaders doing it, neither you strive to be like them because they were fantastic, or you saw other leaders who were absolutely not fantastic and you said, I can do it better. But when you're stuck in survival mode leadership, you're not doing it.

So be honest with yourself. Are you leading with intention right now or are you just simply getting by?

And here's the other piece, I wanna say this, don't think of this in a moment, think of it in a period of time. We're all gonna have moments. All of us are gonna have moments where a crisis comes up and boom, we are just getting by. But I'm talking about in general, are you thinking, I just wanna make it to Friday? Man, I just can't wait till the next break.

Here is the most important thing I want you to hear from this podcast, from this particular episode.

This is really all about that cycle of chaos and leaders don't stay stuck in the cycle because they lack skill. Not at all. Leaders don't stay stuck because they don't care. Not at all. Probably they care too much. Leaders don't stay stuck because they're bad leaders.

I stay stuck because the chaos doesn't disappear on its own. It's not going to simply go away. You have to interrupt the cycle of chaos. Plain and simple. To get out of the cycle of chaos, you must interrupt the cycle. Because here's the thing, you don't just go through the five pieces and you're done. no, no, No. When you've made it all the way to that survival mode leadership,

odds are pretty strong that then you continue constantly reacting, which creates even more high cognitive load, which creates even more lack of clarity or absence of clarity, and it creates even more overextension to which you're even further into survival mode, and it continues and it continues and it continues.

You have to break the cycle. That's how you get out.

You don't though have to fix all five parts. Not all at once. If you want to interrupt the cycle, if you want to break the cycle, you don't have to overhaul your entire leadership approach. You don't have to work harder. Please, please, please don't think for a second you have to work harder. The number one thing that you can do to interrupt the cycle of chaos is to find clarity. Clarity is what creates your capacity.

Start by clarifying your priorities. Just take that step back. What are my priorities? That will help to reduce what lives in your head. If it's not one of your priorities, let it go. Allow it to sit. Start delegating with intention. Don't feel guilty about it. Start to delegate a little with intention. What are some things that other people can and should be doing?

that can come off your plate. Just make small shifts, small shifts, and then momentum will start to work in your favor again.

So before you move on to the next task, before you move on to your next meeting, just pause. Which of the five parts of the cycle would you say you are in the most right now? Again, those five. Constant reactivity, high cognitive load, absence of clarity, overextension, survival mode leadership. Where are you spending the most time? Where do you think you

Awareness, bottom line, that's the first step towards creating that change. Name the part of the cycle you're in, write it down, acknowledge it, not with judgment, just acknowledge it and say, you know what, I am really stuck in one of the five.

And then just take a small step. What's one small step you can take to gain some clarity and to start to interrupt that cycle of chaos?

If you want support in this work, whether that's through the leadership guide, which you can get at darrenpeppert.com, or a coaching conversation, or you just want to simply carve out some intentional reflection time this week, know this. I am here to help you. I am here to support you. Send me an email, darren at roe.awesome.net.

Just send me quick email. It doesn't mean you have to hire me as a leadership coach. Just want a couple minutes, reach out. Let's have a conversation.

Just remember, you don't need to work harder. You just simply need to work clear. Man, thank you so much for spending this time with me today. Thank you for letting me walk you through the cycle of chaos. If this resonates with you, if this is something that you're saying, man, that is exactly where I am. That's exactly what I'm struggling with. Share this with somebody else. If you were listening to this episode today and you're thinking of somebody else, like, my gosh, you just nailed so-and-so.

Send them this episode. Tell them, hey, you gotta listen to this episode. Check out Leaning Into Leadership and maybe that'll help them break the cycle of chaos as well. As we continue into future episodes, we'll talk more about how you break that cycle of chaos. This is a core piece now of my leadership clarity keynote. So if you happen to be in a place where you get a chance to hear me speak, you're gonna hear me talk.

this. Where am I going to be next? I will be in Oklahoma City or just north of Oklahoma City at the Oklahoma Secondary School Principals Conference. I'll be keynoting their conference on I believe it's the 13th of February. Really looking forward to that. We're going to talk about clarity. We're going to talk about intentionality. We're going to talk about breaking the cycle of chaos. So thank you guys so much for joining me here on the Leading Into Leadership podcast for this special midweek edition. Until next time.

Get out there and have a Road to Awesome week.