#8 | Carrying It Alone: The Weight Every Leader Feels

Leadership is heavy — and most leaders are carrying that weight in silence. In this episode of The Executive Thought Partner Podcast, Dan Freeman gets honest about the internal burden that comes with being in charge: the constant decision-making, the isolation, the subconscious patterns driving choices you think are strategic, and the deafening silence from people around you who are too afraid to tell you the truth. The weight isn't the problem — not knowing how to identify it, sit with it, and reflect on it is. Dan unpacks why reflection is the missing practice for most leaders and what it actually costs to keep leading without it.

If you're reading this and you're in the higher ed, collegiate athletics, or general nonprofit field, I'd love for you to take my survey.

Dan also introduces the power of horizontal leadership — building structures where knowledge flows across teams rather than just top-down — and makes the case that emotional stability at the top creates clarity all the way down the org chart. The episode closes with a simple but disarming challenge: this week, sit with one question for ten minutes without trying to answer it. Because if you're never looking back, you can't truly move forward — and the leaders who learn to process the weight are the ones who stop passing it on to everyone else.

Connect with Dan

Available for Speaking I'm selectively available for keynotes, leadership retreats, and executive panels on decision-making, organizational culture, and leadership identity. If you're building a lineup for your next event, I'd love to be in that conversation. 

→ Reach out at dan@fsgventures.biz or  YourExecutiveThoughtPartner.com

If you made it this far, I want to offer you two limited time discounts. 

• Executive Thought Partner 3-Month Commitment 
• 8-Week Fundraising Intensive Program

View this form to see the discounts:https://forms.gle/ngxwgS6sjCpyppuA8

Connect with Dan

📝 If you're reading this and you're in the higher ed, collegiate athletics, or general nonprofit field, I'd love for you to take my survey.

Available for Speaking I'm selectively available for keynotes, leadership retreats, and executive panels on decision-making, organizational culture, and leadership identity. If you're building a lineup for your next event, I'd love to be in that conversation. 

→ Reach out at dan@fsgventures.biz or  YourExecutiveThoughtPartner.com

If you made it this far, I want to offer you two limited time discounts. 

• Executive Thought Partner 3-Month Commitment
• 8-Week Fundraising Intensive Program 

View this form to see the discounts:https://forms.gle/ngxwgS6sjCpyppuA8

Transcript

SPEAKER_00 0:00

Welcome to the Executive Thought Partner Podcast, where leadership, strategy, and growth intersect. I'm Dr. Daniel Freeman, Executive Thought Partner. This isn't just a podcast about fundraising. It's about how leaders think, decide, and build systems that scale impact across nonprofits, higher education, athletics, and mission-driven enterprises. Here we explore major gifts, governance, culture, and the quiet decisions that determine long-term momentum. If you're leading something that matters and you want clarity with conviction, you're in the right place. Let's get into it. The weight that all leaders feel. I've spoken about that today with another leader. And it was really interesting. All leaders feel the same way, but they don't always know how to say it, how to explain it. That's what we're going to talk about today in the Executive Thought Partner podcast. So I want to ask you a question when I start here today. When did you last sit in silence long enough to hear what you're actually thinking? Sometimes I find that if we don't have the time to reflect, then we're not giving ourselves enough time to process. Now, here's the thing reflection can definitely make our ego uncomfortable. Reflection is a challenge. You have to challenge yourself to be able to sit in space long enough to think about your situations where you're at, right at that moment, to feel in your body if there's any stress. Now, this really ties into kind of my my phrasing from one of my mentors, which is, what am I called here to learn? For us to be able to ask that question as leaders, we need to feel the weight of our decisions. We need to sit in that and reflect. Because if we're not reflecting and we're not assessing and processing, we're never going to be able to move forward because we're always going to be making a new decision without direction from previous decisions and having reflected on the outcomes of those decisions. If fundraising is your job, this show is your edge. Practical insights you can use before your next campaign or conversation. Hosted by fundraising experts like myself and my guests, backed by the team at Donorbox. Subscribe wherever you listen for the Executive Thought Partner podcast. You'll thank yourself later. So the hidden cost of leading without having a thought partner is that the silence can be deafening. There's so many people around you as a leader who are afraid to tell you the truth. Sometimes that can be because they know that you, the leader, might be snippy with them because you, the leader, may not be consistent with them for them to be able to think, I can tell them this every day. Well, maybe I can tell them this every second or third day. Well, I certainly can't tell them on a Monday because they're going to be stressed out. I can't tell them on a Friday. Wednesday, they're usually doing this so they want to relax. So when are your people supposed to talk to you and be honest? Can they? The silence is deafening. There are subconscious patterns driving the decisions that leaders believe are strategic. Those subconscious patterns, those are the patterns that you should be trying to break and challenge by using reflection. That reflection can really help you from burning out because of the amount of decisions you're making in a reactive fashion. And making those decisions reactively versus with reflection and knowledge and being informed, that's when misalignment occurs. And it's not just you, because if you're feeling that way, you're telling other people that report to you, whether indirectly or directly, that that's how they should feel too. You know, I had a conversation today with a friend of mine who was in a leadership role in athletics, and we caught up the last time we had caught up was before my career transition. And one of the first things he said to me was, You look so happy. You just you look so different. You look like you want to be here and you're excited. And that wasn't a reflection on him and I spending time together, but it was a reflection on the energy that I was putting into the universe. Him and I got into these conversations about vibes and energy, and it's true, you can feel it. Just like in philanthropy, just like when you're working with donors, just like when you're around leaders, if you're really trying to be in tune with the leaders that you report to, you will feel the vibe. You will feel the energy from them, whether you have the ability to separate it and separate what you're feeling from how they're acting, or vice versa. I remember on many interviews interviews I've been on and people I've been around. I can always tell when someone's anxious. I can tell in their words, I can tell in the way that they walk, I can tell in the way that they talk, and I can tell in the way that they're just interacting with the world around them. And I call that awareness. This reflection, this processing, this challenging of how we've always done everything, and the opportunity and the ability for us to move forward and to work that muscle so it becomes consistent. Those things they all tie in to awareness. You need to be aware of how you're coming across, you need to be aware of how you're acting, you need to be aware of your employees, you need to be aware of how the decisions you make affect more than just you and your direct employees. How do they indirectly affect people around your network? And how do you use that awareness to be able to move yourself forward in leadership? Now, when we think of this weight, because I'm going to keep coming back to how we started this, when you think of this weight, the need to have awareness of everything around you, of what's going on, and then to not be able to react on that, even though you're keenly aware of it, that takes time. It takes a lot of time because when you're hyper-aware of everything going on around you, everything feels urgent. So there's this line that you need to find where you need to be aware, but it doesn't mean you need to act on that awareness and what you're seeing and what you're feeling. When I'm around leaders who are angry, or I can tell that they're anxious, or I can tell that they're being way quieter than usual. I don't always call that out. I don't. You don't need to. But there's the strength in being aware of all this, but then not having to act on it. Because as a leader, you have to separate yourself from those emotions sometime, because those emotions, that emotionally unstable space is where bad decisions are made. That's when everything's heightened. And in my work, I always talk to leaders about how do you create an emotionally stable space while still being aware of everything around you. And here's how this really plays into the framework that I have and how I like to work with leaders to combat urgent and reactive decisions. How I like to help the leaders reflect by being thoughtfully challenged in a way that doesn't feel judgmental. To have that awareness and to not react on it, it requires something else. It requires something a lot of people don't talk about. And what is that? That's creating a structure below you that reports to you that has task and autonomy. I want you to take a second and think. If you're aware of everything, but the goal is to not react to everything, how does the job get done? Think about that. Who is getting the job done if not you? And that is how I work with my leaders, and then I work with them and their teams. Because if the leader can be aware but not be reactive, then they can use that emotionally stable space to communicate with their employees, to continue to work on this horizontal leadership structure, this multiplier structure where knowledge is disseminated across versus down. And what that does is when you can create that horizontal leadership structure, the middle managers or the senior leaders below you, depending on what role you're in, they know what you need. Because they can see the pattern, you're aware of it, you're acknowledging it, you're asking them to hold themselves and their team accountable for it. But here's the key you're doing this from an emotionally stable place where you can be clear, you can clearly communicate with those individuals and tell them exactly what's needed to be done. And by doing that, you can then help those senior leaders or middle managers to also work from a place of emotional stability because they're not running around with their heads cut off. They're not thinking, I don't know what to do, I'm getting all these emails, all these text messages. No, no, no. They have clear communication from you, from the leader, from the CEO. So, what does that do for them? They now have that clear communication. They can take that, they can go to their employees, and they can say, Okay, I got it. I I pick up what you're saying. You're telling me you just need me to do this. And then you're telling Charlie they need to do this, then you're telling Dawn they need to do this, and then you're telling Andrew they need to do this. So we all know what we need to do, which is exactly what our middle manager or our senior manager wants, or senior leader, which is what the CEO or the top leader is looking for. So not only have you created horizontal leadership, you've disseminated information clearly, and then you've also delegated with task and autonomy. And if you're looking for buy-in and growth for your employees that are not middle managers or senior managers, you've got to give them the autonomy too, so that they will take that and run with it. And it's okay, they're going to feel okay if they mess up because you've come to them an emotionally stable place. And then the real test is if they do mess up, you need to have a debrief reflection, just like we talked about before, to figure out was there a breakdown in communication? Did they just not know how to do it? And they need a little bit more direction than what you gave them. Or did they just miss? They struck out. That's okay too, because that's how we learn. So it's really important to understand this weight of all leaders. Everyone has it. A lot of it comes from reflection, a lot of it comes from awareness, a lot of it comes from loneliness, being the only person to think about it and not feeling, and I say feeling, not feeling like you have time to thoughtfully reflect and assess and process. If we are not looking back, we are not able to move forward. If we are always present, we're not reflecting, and we're not assessing for the future. We've got to be in the present, learn from the past, and then assess for the future. Now, as we get to the end of this Executive Thought Partner Podcast number eight, where we've talked about the weight that all leaders feel, I want to ask you this. This week, can you sit with one question for 10 minutes without trying to answer it? I want you to think in all of your situations, big decisions, scenarios, ask yourself, what am I called to learn right now in this scenario? Is it triggering me as a leader? And is there a way that if I take 10 minutes to not shoot back an email or a text message, if I sit in this and just breathe for 10 minutes, or I go for a walk, if I do that, does that change how it feels? Thanks for listening to the Executive Thought Partner Podcast number eight, the weight that all leaders feel. Thank you for listening to the Executive Thought Partner Podcast. If today's conversation helped clarify your leadership or expand your thinking, share it with someone navigating meaningful decisions. Until next time, think clearly, lead intentionally, and build what lasts.