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When Putting People First Results In Putting Yourself Last, With Kristen Hadeed

Career Sessions, Career Lessons | Kristen Hadeed | Human Leadership

 

What happens when your commitment to putting others first comes at the expense of your own well-being?

Kristen Hadeed built Student Made into a successful business known for its people-first culture. But after years of prioritizing her team and company above herself, she reached a breaking point. She had lost her passion, felt disconnected from herself, and realized that the leadership philosophy she believed in had become a source of burnout and resentment.

In this episode of Career Sessions, host J.R. Lowry sits down with Kristen, author of Permission to Screw Up and Human Leadership, to explore her journey from people-pleasing entrepreneur to a leader who understands that caring for others shouldn’t mean abandoning yourself.

Kristen shares why she made the difficult decision to close the business she’d spent years building, how deeply held beliefs from childhood shaped her leadership style, and why avoiding uncomfortable conversations can actually damage the relationships we’re trying to protect.

They also discuss practical ways to become a more effective and authentic leader, including how to recognize the beliefs holding you back, make time for self-reflection, give meaningful feedback, and have difficult conversations with courage and compassion.

Whether you’re leading a team, navigating burnout, or questioning whether you’ve outgrown your current role, this conversation offers a powerful reminder: great leadership isn’t about being perfect or keeping everyone happy. It’s about having the self-awareness and courage to lead yourself as well as others.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kristen-hadeed/.

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When Putting People First Results In Putting Yourself Last, With Kristen Hadeed

Kristen Hadeed has spent much of her career thinking about what it means to put people first. She built Student Maid into a company known for its culture, wrote a book about giving people permission to screw up, and became a sought-after voice on leadership. Along the way, Kristen discovered that there can be a dark side to people-first leadership. In trying so hard to take care of everyone else, she stopped taking care of herself.

As she puts it in her new book, she abandoned herself and called it leadership. That realization sent Kristen on a much deeper journey. Examining the beliefs that were driving her, learning to recognize what her resentment was trying to tell her, and finding the courage to have conversations that she had spent years avoiding. Her new book, Human Leadership, is the story of that journey and an exploration of what leadership looks like when we stop trying to be the perfect boss and allow ourselves to be fully human. Here is my conversation with Kristen.

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Kristen, thanks for being with me on the show.

Thank you so much for having me.

I’m really looking forward to this conversation because it is so much about your personal journey. Why do not we not start with that at the very beginning of your career? You were still an undergrad. You started your own business and, obviously, started developing your own leadership philosophy along with that. Over the years, you realized that it was not maybe everything that you wanted it to be. What was that moment where you started to realize that the leadership philosophy that you thought was making you a good leader was actually hurting you?

I was sitting in my apartment. This was probably ten years into my journey as an entrepreneur and as a leader. It was one of those nights where I just caught my reflection in the window, and I did not recognize the person who was staring back at me. I just felt so disconnected from myself, from the work that I was doing. I did not feel in a place where I was passionate and inspired and lit up, which was always how I was as an entrepreneur and a leader.

It was just this moment where I had to face that whatever it was that I was doing was not getting me to the place that I wanted to be. I needed to rethink what leadership looked like for me because so much of this I knew was tied into my business and the way I was leading. Just a quick story, when I was nineteen, I started a cleaning business, and it was never my intention. I thought that I was going to work in finance, and I started cleaning houses when I was in school, and it turned into a company. Pretty much overnight, I became a leader of a team, and I read so many books that I could find out how to be a great leader and how to build a great company.

The Trap Of Self-Sacrifice In Servant Leadership

Everything that I read was about servant leadership and putting people first, which is something I still very much believe in. What I realized that night was that I had taken it too far, and I had put my company and my team first to the point that I had sacrificed myself and everything that I needed. I had focused so much on building this great culture for others and relationships with others. Yet I felt so not taken care of in the same culture that I had built and not connected to myself at all. That was my wake-up call.

You write about it being as if you were abandoning yourself. What did that actually mean? How did that manifest for you?

Abandonment in so many ways. I think first I was more than a decade into leading my company, and I had changed as a person. I had changed in what I was passionate about and what I was excited about. Instead of going after the things that I really wanted to go after in my life, I felt like I could not make changes because those changes would affect everyone in my company. Abandoning my own growth and evolution as a person. When it came to having hard conversations, I avoided that. If there were people who were not meeting expectations, I really resisted having those conversations because I did not want to hurt people.

I was abandoning what I needed, and the work was falling on me. Even though I had people on the team who wanted to help me, I did not see that. I saw me asking for help as burdensome, because leaders are supposed to take the brunt of it all. I kept it all on my shoulders. These were the ways, the micro ways every day that I was abandoning myself that then added up to this night where I do not even recognize the person staring back at me. This was someone who, in the beginning days of my company, would work until two in the morning without even trying.

Cover of the book Human Leadership: The Courage to Face Ourselves and Each Other by Kristen Hadeed.

I am not saying that should be the norm, but I was so inspired by what I was doing in building that I could not stop. Now it was this feeling of, I do not want to be doing this anymore. I feel trapped inside of this. I want to do anything but, and that was such a shift for me. It was not really about my company. What I learned as I went along this journey is that it was because I had not prioritized myself. When you do that for so long, you get to this point where you realize that you have not taken care of the things that you need, and that has to change in order for the feelings inside to change.

There is a moment you described in the book, I think, where you are asking everybody to rate on a 1 to 10 scale how they felt about the business. I’ll tell you the story.

My heart races when I think about that meeting because we had someone who was a mentor of mine who was leading my team, my leadership team, through a meeting, and he asked us to look at different parts of the business and our team dynamic and rate these areas on a scale of 1 to 10. One of the questions he asked was about our personal happiness at work. Everyone on the team went before me, and their numbers were nines and tens. My number, the truth was, was like two. I cannot remember. I said 9, or 10 or something at the moment, because I just did not feel like I, as a leader, could say I am a two.

What it really was at that point was that I had just outgrown cleaning. When I started the company, it was not something I intended, and it was an amazing company, and I learned so much in it, and I was ready for my next chapter. I was just in this place where I was working on something I was not passionate about anymore, which was an impossible dilemma. How is the leader of the company? It was so many people depending on you. Do you say that out loud in a meeting? Instead of saying the truth, I gave a number that was not true.

You decided to shut it down.

Having The Courage To Close A Thriving Chapter

That was not easy. Now when I look back, I think, what took me so long to make that decision? I thought that the most caring thing to do was to keep doing it. Now when I look back, I realise that if, as the leader, your heart is not in it, if you are not inspired, you cannot possibly build the best version of your company. It actually was not me who made the decision to close the company and transition to what I am passionate about. It was someone on my team who had the courage to say to me, “Let us go after what we are all passionate about.”

I learned that I was not alone in how I was feeling, which I think was a big light bulb moment for me in that meeting where we all rated 1 to 10. I am pretty sure I was not the only one who gave an inflated score. My leadership team also had this vision for a different future that we were all excited about, leadership development work and so much of what we were doing in the company that just was not around cleaning. Eventually decided to close it and go fully into what we were most passionate about. I do not know if I could have done it without the courage of my team giving me that permission as well.

Where does that leave you? You talked earlier about reading all these books and learning about servant leadership. Where does this experience leave you on the topic of servant leadership now?

I am still such a believer in putting other people first and caring for others. I love everything about servant leadership. I just took it too far. I took it to mean that if I am putting other people first, then I come last, or my needs are the ones that are always trumped compared to what other people need. Now I see that they are all important. I do not want to be the leader that says, “It is my needs over everyone else’s, and I do not care what yours are.”

Putting others first shouldn't mean putting yourself last. When you sacrifice your own needs, your leadership suffers. Share on X

I want to be able to be a compassionate leader who prioritizes my own needs and also makes room for what other people need. It looks like having a lot of courageous conversations. Sometimes the needs that we have are in conflict, and it is like, “This is what I need. I hear what you need.” Let us figure out a way to make this work. Maybe it does not work anymore. Having those honest conversations. When we think about servant leadership, we think about leadership. Leadership cannot be that you are not leading yourself in some way.

When I think back to how I was leading, I do not think I was inspiring anyone on my team. What they saw was someone who was burning out, who had lost passion, who was disengaged. That is not leadership. I have learned that in order to be the best servant leader and caring leader, you have got to think about filling your own cup. It is not selfish to do that. To me, it is the foundation of truly generous and compassionate leadership.

What did you change in the way that you approach your day-to-day as a result of all of these little epiphanies, maybe leading up to a big one?

Aside from deciding to transition the entire company, which was, I think, the first step. For me, that was a huge step because I realized in making that decision that the world did not fall apart. I remember the meeting I had with my team to tell them about this decision, and all of our students. I was so worried about this meeting. I thought everyone was going to be devastated. Instead, they were encouraging. Actually, someone said, “You created Student Maid as a place for us to learn about ourselves and go pursue our dreams, and we want the same for you.”

Honest Communication Builds True Connection

That was a powerful moment because this case that I had built up in my head that everyone would be upset, the evidence showed that was not true. What else am I telling myself that is not true? If I had to boil it down to one thing, the biggest change that I made was just having honest conversations when there was something that I was feeling, actually expressing that out loud. So many times I realized that what I wanted was what my team wanted too. I just never gave them the chance to help me or support me because I was not speaking it out loud.

It made our company more honest and more transparent, and it is not just me having those honest conversations. It is my team having them with me. Often I think we avoid the hard stuff because we think it is going to hurt someone, especially if we care about people. We want to be a caring leader when, in fact, it is the thing that not only takes us to the next level, but builds more trust and connection.

Somebody said to me at one point, “A nice boss is not necessarily a good boss.” You can be too nice, and you are not taking care of yourself, or you are not really pushing your team to be better, which obviously is the role of a leader as well.

I have had to really sit with what it means to be a caring leader. Is a caring leader someone who avoids telling someone when their performance is not what you need it to be when someone has not met expectations? When we reverse it, if you were in that position, if I were in that position, I would want someone to tell me. No, it is not caring to avoid the conversation or to sugarcoat it to give it a softer landing. I have learned that you can be really caring and be really honest with people. They are not separate. They are actually connected. The more honest you are, the more caring you are.

In that conversation where you went to your team and said, “Effectively, I do not want to do this anymore. How did that conversation go? What did you say? How did you position it?

Man in glasses holding a Sorry We're Closed sign in a shop window.

Human Leadership: Walking away from a business you built isn’t failure. It’s an act of alignment and honest leadership.

 

What helped me is that I knew where I wanted to go. Without that piece, that would have been an even harder moment. I knew that I was ready to transition away from the business because I had a vision for what I wanted to do instead. Over the years, I learned that my real passion was in leadership development work, which was what the company was about. We cleaned houses, but really we developed students and helped them become better leaders. We had started doing that for organizations outside of our company and helping these organizations build more human cultures.

That is the work that my team, my leadership team, and I wanted to do full time. When I had this meeting with my team, I was just very honest about that. I said, “Along the way, I have learned a lot about myself, and I have learned that this is what I am really passionate about, and I am going to miss this, and Student Maid will always have this special place in my heart, you will, and I am ready for the next chapter.” We did not do it abruptly. We gave time for that transition. We were able to work with two different cleaning companies who offered everyone a job if they wanted it.

We really thought about how to take care of our people along the way. At that moment, my team saw me as human. They saw me as someone who has passions and dreams just like they do. For those tuning in and watching, no matter where you are in your career, whether you own a company or not, I think a lot of times we just make up these stories that other people are going to respond negatively when we go after the things we want in our lives. I am just so grateful that I confronted that because I think about what if I lived my whole life without making that decision, only to find out that they supported it? They wanted that for me too.

How many of them ended up coming along the journey with you into what you are doing now?

My leadership team did. There are four of us today, myself included, so a much smaller team. I think even when I made the decision to transition the business, I still tried to find a way to take all of our students with us. Another lesson in my leadership is that I promised maybe we could find opportunities for everyone. Those did not pan out. I had to go back and say, “No, that is not going to work out.”

Just in that transition, I learned even more about honest communication and saying, “This might look like us never working together again. That is probably what it is going to look like.” Just being clearer about that. It was a learning. These decisions are not easy. We all wish we could make them without the risk of hurting anyone. If we are going to live courageously, lead courageously, sometimes that means that people do get hurt. You get hurt sometimes.

I know you went on an inner journey throughout this whole process. Now that you are working with other people, how do you coach and counsel them to go on that inner journey for themselves?

It is about learning to see yourself and to really spend that time with yourself. We are taught to focus so much on others, and how often do we put that same focus inward? I do not think it is enough to just be self-aware. That is the first step. For me, I could not become more self-aware without the help of others. I had coaches, mentors, my team giving me feedback, and therapists. That is one of the gifts of being human is that we need each other. We need to say, “Where do you see me getting in my own way? How do you perceive me as a leader? Where do you see me getting stuck?”

Challenging The Hidden Beliefs That Hold You Back

Having these conversations is what helped me see myself clearly for the first time. It is what do you do after that? It is this willingness to actually change your behavior and change the decisions that you make. That is hard because it is probably a habit. For me, I learned through a coaching session that I had a belief that it is my job to keep everyone happy around me. That is why I avoided tough conversations. It is why I did not ask my team for help because I was afraid to burden them. It is why I never transitioned the company when I first wanted to.

Avoiding hard conversations doesn't protect relationships. It isolates you and deprives your team of the chance to help. Share on X

In order to move beyond that belief, I had to be more comfortable with the fact that people may not be happy with all of my decisions and all of my conversations. It felt like stretching out of my comfort zone in the biggest way because I did not want to do that. The more I did it, I learned, “The world does not fall apart. My relationships actually get stronger and better.” It is different for all of us, but it is learning to see yourself, investing in the time and the relationships that can help you see yourself, and then doing something with what you discover.

You talked about beliefs a minute ago. A lot of us operate with beliefs that are formed in the early part of our lives. Was that true for you?

Yes. This belief is that it is my job to keep everyone happy. It definitely came from my childhood. It came from the fact that, as a kid, I was always the person in our house who kept the peace. If there was an argument between my parents, I would go find them. I would bring them together. I would say sorry. That was the role that I continue to have in my relationships. You add that with everything I had learned about servant leadership and wanting to put other people first. It was just this recipe for being so afraid to hurt people, but it is different for everyone. It could be a belief that you cannot fail or that you are not good enough, or that you do not belong, and it is usually what is underneath the decisions and actions where we are getting stuck.

Are you an oldest child?

I am.

That is very true for a lot of oldest children, maybe not the peacekeeping part, but certainly the feeling like you have to be the responsible one in the room when your younger siblings are all causing chaos.

Yes. When I learned my belief, I wanted to take that to my team because I wanted to see, “If I have this, what does everyone else have?” We had some of the most meaningful conversations, and I learned about everyone’s life. There is someone on my team who thought that she was not good enough. Up until that point, I could never understand why, any time we would have a conversation about feedback, she would shut down.

She would get really defensive. I realized it was because of that belief. It would just trigger this feeling that she could not do anything right. Once she worked on that, we were able to have such great feedback conversations. We all have them. A lot of times our beliefs help us get to where we are. There is a part to be grateful for, but then it is also, “Where am I being held back by this belief, and how do I challenge that and change my behavior?”

I would imagine having that conversation with your team was very difficult.

Leader in front of a whiteboard listing trust, effort, achievement and motivation, talking to a team at an outdoor table.

Human Leadership: Are you leading your team, or are your childhood coping mechanisms running the show? Unpack the beliefs driving your decisions.

 

It was definitely one of the most vulnerable we had had up to that point. We had the trust to be able to have it. That is a key ingredient for a conversation like that one. We were at the time I was hosting a monthly leadership session where we would come together and we would just spend a whole day together learning about leadership. When I did that exercise with my coach, I thought, “This will be great for this leadership day we have.”

It was very vulnerable. I am so grateful for my team’s courage and willingness to share, and we learned so much about one another’s lives. It increased our empathy because, for behaviors that frustrated us, we could understand where they came from. It was not a hall pass. It was not like, “You can just act that way because that is your belief.” How do we challenge each other to outgrow the parts that are holding us back?

Having this realization that you do have these biases and beliefs that shape how you think and how you react to things is a start. You talked about self-awareness being a start, but then knowing how to check yourself in the moment when it happens. The person who would get defensive with feedback because she may not believe in herself as much as she should. When she is getting feedback, it is a wholly different thing to realize that you were having that reaction and to course correct right then and there.

It does not happen if we are not willing to be curious about ourselves, to take time to get to know ourselves. It is the most important relationship of all. Something I like to think about too is how much time this week I have connected with myself. If I have a moment where my emotions are higher than they normally are, or I am feeling an emotion that is not so positive, that is a clue. That is a time to stop and reflect and think about what is happening here and to get curious about it. It is that daily habit of reflection and curiosity that I think is how you learn to lead yourself.

That is very true. Just in the sense that you do need to give yourself reflection time. Too often we just get so caught up in the heat of the day-to-day. The days are long as they are without having reflection time, but finding even little moments to have a bit of reflection can make a huge difference. Was that true in your case?

Yes. What I also realized is that when I looked at my calendar, it just showed that I was not a priority. My calendar was stacked with everything that everyone else needs. It makes sense why when I get to the end of the day, I do not want to do anything else. I just want to watch a show and not think because I have been thinking all day. I had to think about my time differently. I have a practice that really helps me. I call it my daily meeting with myself, and I start my day with it and end my day with it. Before I meet with anyone, I just have 15 or 20 minutes with myself where I reflect.

Establishing A Daily Meeting With Yourself

I reflect on the day. I reflect on how I will take care of myself today. How am I feeling today? Are there conversations I need to have today? At the end of the day, I look back, and I say, “How did I do? What can I learn for tomorrow? Also, is there anyone I need to apologize to?” Sometimes I realize maybe I did not show up in the best way as a leader. This habit of starting and ending with this connection time now is just a part of my routine. It does not happen unless we put intention behind it.

It is a great practice that you have just described. It takes discipline, obviously, but all habits take some amount of discipline until they become the habits that they are. Just giving yourself that time at the beginning and end of each day is a good way to bookend each day and help yourself get better every day. I commend you for doing that.

Thank you.

If your calendar is packed for everyone else, you aren't leading. Book a non-negotiable daily meeting with yourself. Share on X

Come back to this idea of vulnerability. We teach leaders, or leaders often believe, that they should not, cannot be vulnerable with their teams. You had a very vulnerable conversation, probably multiple vulnerable conversations, around that decision point of shutting down a Student Maid. Where do you draw the line between vulnerability and oversharing?

It is tough. Vulnerability is what makes us human. If we are not allowing people to really see us, we cannot build the kind of connection and trust that is possible. Vulnerability can look different in so many ways. Vulnerability could be, I am not sure what to do, or I failed, or I am not sure of the best path forward, but this is how I feel, and I do not know what to do about it. Sometimes, as leaders, we think we have to put on this front that we always know and we always have the answers, and that any kind of vulnerability is perceived as a weakness, but it is actually perceived as a strength because people see you as a human, and then they can help you and be a part of what you are doing.

It is about vulnerability with purpose. It is Brené Brown who says that when I am thinking about something that I want to share, what is the purpose of me sharing this? It is oversharing if there is not a purpose to it. A lot of times, some of the most vulnerable things I have shared are because I need the person on the other side to understand the magnitude of where I am and what I am feeling so that we can come to a better place together.

It is a line I have learned over time. In the beginning days of my company and Student-Maid days, I had keg parties, and I was doing a keg stand with my employees holding my legs up on it. I would say that is the line that was crossed. There is a way to be a leader of a team and have those professional boundaries, but also have these relationships that are really honest. I do not think you can do it without vulnerability.

On the other end of the spectrum is strength and being willing to have tough conversations when they are needed. This is something you have talked about struggling with, and this desire to keep the peace and keep people happy. How did you learn, or what did you learn, about how to do both well? How to keep people feeling happy or at least happy enough, while also holding them accountable?

I have something I follow that has really helped me. It is called the 24-hour guideline. It is just basically a commitment that within 24 hours of feeling something or observing something, I will have the conversation. Do I always hit that? No. Sometimes I go a little beyond. In general, it helps me to stay accountable to not avoiding and just addressing it. The other thing is, in the past, I have focused so much on almost controlling the other person’s emotional experience and trying to make sure that the message is received positively, to the point where sometimes I am not able to get the stuff across that I really need to.

There is a way to be direct and clear and also be compassionate and make the person feel like you care about them. In the end, they are empowered to have their emotional experience. There is something very powerful about somebody being disappointed or frustrated or not happy with what they are hearing, and allowing them to feel that and allowing them to share with you how it is making them feel and what it is bringing up for them.

Practicing The FBI Feedback Framework

That actually builds even more trusting relationships because then you feel safe to be completely authentic with what you feel. One of my favorite methods I love is called the FBI and it is Feeling Behavior Impact. How do you feel? What was the specific behavior that made you feel that way? What was the impact of that behavior? I felt let down yesterday when you were not at the meeting, and the impact is that I fear the team is questioning your commitment to the project.

Tell me more. I am really curious about what is underneath that for you. I have learned that feedback can be a conversation, a dialogue that is really powerful when you can become curious about their emotional experience. If you are tuning in to this and you are like, “I definitely avoid tough conversations, try the 24-hour guideline.” You do not have to do it perfectly. Learn from every conversation, and each one will keep getting better.

Colleague wearing a headset leaning in to support a coworker at her desk.

Human Leadership: Feedback doesn’t have to feel confrontational. Use the FBI method: feeling, behavior, impact, to build trust and accountability.

 

Certainly, getting comfortable and practiced and developing feedback makes a huge difference, and not letting it fester. If you come to somebody three weeks later, but something it is going to feel like a much bigger deal even if it really was not a big deal.

It is almost like having the conversations about the smaller things allows you to build the trust to then have the bigger conversation. This habit of just addressing things shortly after they happen, then, when inevitably this is a place we get to in our relationships, there is something bigger. You are really frustrated with the person. Whatever it is, you have the trust built up to be able to have that conversation. If you have not had any of the conversations leading up to it, then that is a really hard one. I also just want to say that I do not find these conversations comfortable.

As somebody who writes about it and teaches it, I still want to throw up a little bit every time right before the conversation. I have butterflies in my stomach, but I think I have learned that fear is a sign of caring. It is because I care about the connection with this person, and I know that avoiding the conversation is the very thing that will threaten that connection. It really is about courage. I do not think we want to wait until the fear is gone because it might not ever be gone. It is really about learning to move forward and have the conversation even when that fear is so strong.

Avoiding it takes a toll on you, and it cheats the other person out of an opportunity to get better.

It risks trust because on the other side, the person is like, “Wait a minute, we have had so many conversations. I never knew that anything was wrong. Now I am learning this. How can I trust you next time when you say everything is fine?” Maybe it is not. It can really do a lot of damage when we avoid it.

Do you give a lot of positive feedback as well?

I do. I am intentional about that because I think that is important too. It gives people the puzzle pieces to know what to do again. If someone is only receiving the critical feedback, then they might not receive it very well because they are not also getting the positive side. With the positive, I just want it to be really genuine. I try to avoid the great work or love having you on the team. Actually, I use the FBI to be really specific about what it was they did and the impact it had. If you do that, you can actually recognize people less, but because it is more intentional, it means more.

All of this, you brought together a new book, Human Leadership. You want to tell us a little bit about it and how it builds on your prior book as well?

Yes. Human Leadership is really the story of learning to face myself and other people. It starts with the night that I looked in the window and could not recognize the person staring back at me, and the journey I went on to get to the place where I look in the window and I love the person staring back at me. I would say it is a book of all of my failures and all the things I avoided, and how they went wrong and how I learned through those moments. It is the most vulnerable thing I have ever written. To be very honest, it is a little scary to put it out into the world. I also know it was the book that I needed to read. If I had read it, it could have probably saved me a lot of heartache and maybe given me some courage to address what I was avoiding.

How does it build on your prior book?

You can't let new opportunities bloom if you won't prune what's holding you back. Embrace endings to spark real growth. Share on X

My first book is called Permission to Screw Up. In some ways, it is just a continuation of screwing up, as it is to be human. The first book was very much about Student Maid, the story of building Student Maid and learning how to be a leader and learning that the only way that you can really learn is by failing. It picks up right where Permission is corrupt left off and everything that has happened between the two books. There have been almost ten years between those two books. It is a journey of learning to walk away from the company that started it all and really taking ownership of the life and the career that I wanted.

For our audience tuning in or watching, for you, Student Maid was not just a company as it is with a lot of founders. It had become a big part of your identity and your public persona if you want to think about it that way. For somebody tuning in or watching, what advice would you give them about how to know whether they have hit a point where they have outgrown something that has, up until then, defined you, or whether you are just going through a tough season and you need to push your way through it?

There are definitely moments where we can be working on something we love and still feel overwhelmed and burned out. We unplug for a little bit, we take a break, we get a few things off of our plate, and we come back, and we are passionate and excited to be working at it again. For me, just the underlying spark was missing. It was not something loud, which I think is important. It was like this whisper that I would just always hear that I meant to be doing something else.

Pruning Necessary Endings To Allow New Growth

I could feel my heart pulling me in a different direction, and I was trying so desperately to ignore it because I did not want to think about what that would mean. There is a great book that helped me a lot. It is called Necessary Endings. written by Dr. Henry Cloud. He talks about a rose bush, and he says, “We all have these roses, which are the things in our lives that we want to bloom, but the roses can never bloom if we do not have the courage to prune the bush.”

In order to have beginnings, you have to have the courage to have endings. I just knew that Student Maid was ending. I think we know. We just have to trust ourselves. It is also okay to not rush it. I needed to give myself time to really make that choice. The day when I knew I was ready. Be gentle with yourself and maybe think about the thing that is tugging at you, a rose in your life that really wants your attention.

Thank you. Thanks for sharing your story in your new book. I am sure a lot of people will see themselves in aspects, if not a lot of your story, because a lot of us go through this journey, particularly when we are in the early parts of our career, about who we are and who we really want to be and whether what we are doing aligns with that. The sooner you can figure that out for yourself, to really know yourself as you have worked hard to do, the happier and more fulfilled you are going to be from there on out.

A hundred percent. Thank you so much for having me, and thank you, everyone, for tuning in and watching.

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To wrap up my conversation with Kristen just now, here are a few ideas that I hope you will take with you. First is this idea that putting people first should not mean putting yourself last. Great leadership requires caring deeply about others, but when that care consistently comes at the expense of your own needs, values, and well-being, it can become self-abandonment rather than service or servant leadership.

Second is this idea that better leadership starts with understanding what is driving you, and that needs to go beyond just the idea of self-awareness. We all bring deeply held beliefs, fears, and patterns into the workplace, often without realizing it, things that might have developed in our childhood. Doing the inner work to understand these forces and to know how to respond to them and deal with them in the moment really can change how we handle conflict, make decisions, set boundaries, and lead others.

Third is that human leadership takes courage, not perfection. Sometimes the most caring thing we can do is have a conversation that we have been avoiding, tell uncomfortable truths, and make a decision that disappoints someone. Being human does not mean being soft. It means being honest, compassionate, and willing to face difficult things rather than avoid them.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with someone who is looking to become a better leader, build a stronger career, or better understand themselves. You can also look to us for corporate workshops, events, and speaking, or if you are an individual, join our membership community, which is called PathWise. Information on both is available at Pathwise.io. Thanks.

 

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About Kristen Hadeed

Kristen Hadeed, guest on Career Sessions, Career LessonsKristen Hadeed is an entrepreneur, author, and leadership speaker who helps leaders, teams, and organizations build trust, belonging, and wildly engaged cultures. At 19, she founded Student Maid, a student-powered service company that grew from a college side hustle into a globally recognized business known for developing the next generation of leaders. She is the author of Permission to Screw Up, which has sold more than 50,000 copies worldwide. A sought-after leadership speaker, Hadeed works with organizations ranging from small businesses to Fortune 100 companies and is an Optimist with Simon Sinek, Inc. She created the Human Leadership Program, which has more than 4,500 alumni. Her work has been featured in TIME, Forbes, and Inc., and on PBS, FOX, and NBC’s TODAY . One of her two TEDx talks has surpassed 3.3 million views.

 

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