Ep #77: The Hidden Grief of Leadership: Why Setting Boundaries Feels Like a Loss

The Reinvention Lab | The Hidden Grief of Leadership: Why Setting Boundaries Feels Like a Loss

Have you ever felt a sense of loss when setting boundaries as a leader? It’s a hidden price tag that nobody warns you about, but it has everything to do with who you become. In this episode, I reveal the real cost of becoming an authentic leader and why it’s worth every penny.

I recently found an old journal entry where I had written about saying yes to everything, even at the expense of my well-being, because I thought that’s what leaders should do. Seeing those words reminded me of my growth and the truth that boundaries are the most generous gift we give to ourselves and others as leaders.

Join me in this episode as I explore the unexpected grief that comes with setting boundaries as a leader. I’ll share why some strong leaders struggle with these shifts and how unpacking that grief makes your boundaries more sustainable and your leadership more authentic. Let’s dive into the hidden emotional landscape of setting boundaries and discover what happens after.




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What You’ll Learn from this Episode:

  • Why setting boundaries feels like a loss at first, even when they are essential.
  • How to recognize the grief of letting go of old habits and leadership comfort zones.
  • The profound identity shift that comes with setting boundaries as a leader.
  • How digital boundaries expose our fears about leadership.
  • Why the grief you feel when setting boundaries is a sign you’re becoming a more genuine leader.

Listen to the Full Episode:

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Full Episode Transcript:


What if I told you setting healthy boundaries in leadership has a hidden price tag that nobody warned you about? This price tag has nothing to do with money, but everything to do with who you become. I am revealing the real cost of becoming an authentic leader and why it’s worth every penny. Stay tuned.

Welcome to The Reinvention Lab: Where Ambitious Women Transform Loss into Legacy. Hosted by Master Certified Life Coach and fellow trailblazer, Sandy Linda, this is your space to discover how life’s biggest challenges can ignite profound transformation—where grief becomes growth, setbacks become stepping stones, and your unique story lights the way for others. If you’re ready to turn life’s challenges into opportunities for leadership, legacy, and forward momentum, you’re in the right place. Let’s dive in.

Hello, creative humans and fellow trailblazers. This time of year has me reflecting on the emotional shifts I’ve experienced. Recently, I cleaned up my home office and found an old journal entry. In it, I had written about a time I said yes to everything, even at the expense of my wellbeing, because I thought that’s what leaders should do. Seeing those words, I felt grief for my past self, but that grief reminded me of my growth. Navigating love, loss, and reinvention has taught me one truth. Boundaries are the most generous gift we give to ourselves and others.

Today, I am inviting you to explore that with me. You know what fascinates me about leadership? It’s those unnoticed moments behind closed doors, in quiet reflections, when we’re battling tough decisions. One pivotal moment came during a boundaries workshop I facilitated weeks ago. We were discussing setting healthy boundaries and trading tips and strategies when the energy shifted. A leader shares her struggle, another nods, and it became clear. It wasn’t just about boundaries. It was about grief. The unexpected ache when you realize that becoming the leader meant letting go of who you used to be.

What struck me, every time someone mentioned setting a new boundary, there was a quiet hesitation, an unspoken grief over what they had to release. So many of us carry an invisible backpack of unresolved loss, yet we never give ourselves permission to unpack it. Today, I want to change that. Together, we will explore the hidden emotional landscape of setting boundaries. Not just the how-to’s, but what happens after.

I will explore why setting boundaries feel like a loss at first, even they are essential. I’ll share why some strong leaders struggle with these shifts, and how unpacking that grief makes your boundaries more sustainable and your leadership more authentic.

Let’s start with a common challenge for leaders, the loss of old habits. This first layer of grief might surprise you, but I see it repeatedly in my work with ambitious women leaders. Consider your business right now.

You have built systems, created processes, established rhythms, and this is what I call your leadership comfort zone. It’s the familiar framework of, this is how we do things around here. And it works for a while until it doesn’t.

Here’s what happens. You are growing, evolving, ready for a bigger vision for your business. But those systems that once supported you felt like a cage. Maybe you’re saying yes to energy draining clients because that’s what you have always done. Maybe you’re working 60-hour weeks because that’s how you build your success the old habits feel safe, even when it’s no longer serving you.

Are you sad because change feels unsettling? It’s not just normal. It’s necessary. It’s a signal that you are growing beyond your old container. The most successful leaders I work with recognize this grief, not as a warning to stop, but as a confirmation they are moving in the right direction.

When you set new boundaries, like restructuring your client’s acceptance process, redefining your availability, or rebuilding your service model. You might grieve the simplicity of your old ways, but what awaits is a more valuable business that honors your ambition and wellbeing. We’re talking about real freedom, authentic flexibility, and guilt-free family time.

Now let’s talk about the profound grief that comes with setting boundaries. The shift in how you see yourself. Do you recognize the leader you have been until now? The one who prized yourself on being available 24/7, solving any crisis, and built your reputation on being the go-to person. There’s a part of you that’s attached to that identity.

I see this with the brilliant women I work with. One leader recently told me, I used to wear my constant availability like a badge of honor. The thought of not being there for my team felt like I was failing them. Does this resonate with you?

Here’s the truth. When you start setting boundaries, you’re not just changing what you do, you are changing who you are. And yes, that brings up grief. You’re grieving the identity of the leader who could do it all. You’re grieving the story you told yourself about what makes you valuable.

Let me share something powerful I have witnessed. Every time a leader in my community set honest boundaries, something remarkable happens. Initially, there’s fear, worry that they are somehow becoming less than. But then something shifts.

They discover that their worth isn’t tied to their availability. Their value isn’t measured by how many fires they can put out in a day. Instead of being the always present leader, you become the purposeful leader. Instead of being the problem solver, you become the wisdom holder who empowers others to find solutions. Your identity expands rather than diminishes.

Think about it this way. When you first learned to swim, you had to let go of the pool’s edge. It felt scary, maybe even like a loss of security. But only by letting go, could you discover your ability to move freely through the water. Setting boundaries is similar. It’s not about becoming less, it’s about discovering how much more you can be.

Remember why you started this journey of reinvention. The boundaries you’re setting are not walls. They are foundations. They are not holding you back. Creating space with boundaries lets your true leadership shine. Yes, You might grieve the old identity that felt safe and familiar, but what you’re building is far more powerful. A leadership style that honors both your strength and humanity.

Now that we have discussed how our identity as leader shifts when we set boundaries, let’s dive into something in your hands right now, the complex relationship between leadership, technology, and boundaries. And yes, there’s grief here too.

Consider your typical day as a leader. Your phone buzzes with Slack notifications during dinner with your family, emails pile up during your daughter’s dance recital, a client sends a quick question via text at 9 p.m. Sound familiar? We have created an always-on culture where responsiveness is mistaken for responsibility.

An audience member from our workshop shared her pride in being available 24/7. She said, “I keep my phone on my nightstand because what if someone really needs me?” Her identity was so tied to being the always available leader that disconnecting felt like abandoning her team. Maybe you can relate.

Digital boundaries expose our fears about leadership. When I asked her what would happen if she didn’t respond immediately, She paused. “I guess I’m afraid they’ll think I don’t care enough,” she admitted. “Or that I’m not committed enough.” There it was, that familiar thread of worthiness we talked about earlier.

The truth is our relationship with technology has created a new kind of grief in leadership. We’re grieving the loss of clear work-life boundaries, he simplicity of leaving work at work, and the illusion that constant availability make us better leaders.

Here’s what I have observed in leaders who have mastered digital boundaries. True leadership presence isn’t about being always on. It’s about being fully present when you are on. One leader in my community started presence hours, times when she’s fully available for her team, but fully unavailable during protected time.

The result, her team became more resourceful, her decisions more thoughtful, and her leadership more impactful. This isn’t just about turning off notifications. It’s about reimagining responsiveness versus responsibility. It’s about understanding that instant responses train your team, clients, and yourself to expect that norm. And let’s be honest, no one does their best strategic thinking in the middle of a constant stream of interruptions.

Remember, your phone has an off button and your email has an auto responder. These aren’t signs of weakness. They are tools of wisdom. And yes, there might be some grief. Letting go of that always on identity might be tough, but you’re gaining something more valuable. The space to be a leader who leads from clarity rather than chaos.

When I started this conversation today, I wanted to highlight something we don’t discuss enough in leadership. The connection between grief and boundaries. We have explored how setting boundaries touches every part of our leadership journey. The comfort of familiar systems we need to let go. The identity shifts that challenge our sense of self, and even our relationship with technology in this always-on world.

But here’s what I want you to take away today. The grief you’re feeling when you set boundaries, it’s not a sign you’re doing something wrong. It shows you’re becoming a more genuine leader. Think about it. Every time you feel a discomfort when you say no to a project that doesn’t align with your vision. Turning off your phone during family dinner. Stepping back from being everyone’s go-to problem solver. You’re not just setting boundaries, You are choosing to lead with intention rather than habits.

Here’s your invitation for this week. Choose one boundary you have been reluctant to set. Maybe it’s declaring meaning-free Fridays, establishing special hours for client communication, or simply giving yourself permission to take a full lunch break. Write it down. Then write what you might need to grieve as you implement this boundary. What are you letting go of? What identity are you shedding? Remember, every strong leader before you have gone through this process.

They’ve learned that setting boundaries isn’t about building walls. It’s about creating space for what matters. They had to trust their own worth isn’t measured by their availability, but by their impact.

As you leave this conversation today, know this. You can miss the old ways and choose the new. You can feel the grief and move forward. You can be a strong leader and still need support. Understanding and embracing this makes you a good transformative leader.

Your boundaries aren’t just about protecting your time and energy. They are models of sustainable, authentic leadership. In a world that needs more fully present and connected leaders. Your boundaries serve you and everyone you lead.

Thank you for joining me today. I hope this conversation gave you some inspiration and keep leading with courage, with boundaries, and most importantly, with self-compassion. Have a great week, everyone. Bye!

Thanks for joining us on The Reinvention Lab. If today’s episode inspired you, don’t forget to follow and share it with someone who’s ready to turn their challenges into opportunities. Want to take your journey to the next level? Visit sandylinda.com/program and apply for coaching today. Together, we’ll turn your story into a legacy. Until next time, keep moving forward with purpose, passion, and power.

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