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Leading Through Heartbreak: The Balance of Holding On and Letting Go

9/30/1989

I’m happy, and I’m extremely sad. I am happy because I’m home and I saw my brother. I’m sad because my brother seems to be deteriorating with the neighborhood. My brother was once big and muscular, and he looked like my big brother. He resembled a football player with the gear on.  Now he’s frail and little. I couldn’t believe my eyes when I saw him. I saw him on the street, and I didn’t want to make it obvious how shocked I was, so I just smiled and hugged him. Even his hugs didn’t feel the same. How could he do this to himself? I don’t understand, and I guess I never will. All I know is that I love him no matter what, and it hurts like hell to see him that way. I hope to God he sees himself and looks inside to try and find himself because he is in desperate need. I’d really love to sit down and talk to him, but I’m afraid I’d break down and cry in front of him, and I don’t want to do that. I guess I have to deal with it the best way I know how. Just sit back and put it in God’s hands.


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Let’s talk about the collision of emotions we often navigate in leadership—the space where happiness and sadness coexist, where you’re hopeful yet hurting.


I was reminded of this when I revisited a personal journal entry from years ago. In it, I reflect on the painful moment of seeing my brother, once strong and vibrant, slowly becoming a shadow of his former self. That mixture of joy and sorrow—being happy to see him but heartbroken at his condition—is something that has stuck with me, even today.


How does this connect to leadership?


It’s all about the balancing act. In that journal entry, I didn’t realize it at the time, but I was learning an invaluable skill: how to sit with discomfort, how to hold both joy and pain in the same breath, and how to keep going without allowing either to dominate. This balancing of emotions is so critical in leadership. There will always be tension between celebrating successes and recognizing where things are falling apart. It’s a skill that needs intentional practice, and if we don't learn to balance these opposing forces, we’ll burn out, or worse, lose touch with our core.


Balancing Work and Emotions in Leadership

In the same way I had to navigate my feelings about my brother’s decline, leaders must also navigate their internal emotional landscape while managing their external responsibilities. Leadership isn’t just about driving change and getting results. It’s also about managing the weight of hard truths, seeing people you care about struggle, and sometimes not having all the answers.


It would have been easy to either completely break down or pretend everything was fine in that moment with my brother. But neither would’ve helped the situation. Instead, I had to let myself feel the sadness while still holding onto love and hope for him. In leadership, this duality exists all the time. You can’t be in denial of what’s going wrong, but you also can’t let it consume you.


That journal entry helped me realize how important it is to acknowledge what’s happening without letting it paralyze you. And that’s the balance you have to strike as a leader too. You have to know when to push forward and when to take a step back, reassess, and put things in their proper place.


Intentional Practice in Balancing Work

Balancing emotions is not a passive skill; it requires daily, intentional practice. It’s like flexing a muscle—if you don’t work on it consistently, it won’t strengthen. The same way I was learning to manage my personal feelings with my brother, leaders must practice this balancing act daily. It starts by acknowledging the emotions you’re feeling—whether it’s frustration over missed targets or joy over a staff member’s growth—and then deciding how you’ll carry those feelings into your leadership decisions.


It’s easy to get caught up in work, allowing either the highs or lows to dictate your mood and, in turn, your actions. But the real strength comes from balancing the two. If we get too wrapped up in the highs, we become complacent. Too absorbed by the lows, and we lose our drive. It’s the balance that keeps us moving forward—able to handle both the wins and the losses with grace.


Putting it into Practice

When you’re faced with your own “brother moments”—whether it’s a staff member who isn’t performing, or a student struggling despite all your efforts—remember that balance is key. You’re going to feel the tension between wanting to solve it all and realizing some things are beyond your control.


What matters most is that you don’t allow those feelings to overwhelm you.


Sit with the discomfort, but don’t let it anchor you.


Feel the joy, but don’t let it make you forget the work ahead.


Just like I wrote in my journal all those years ago: sometimes you have to step back and trust that things will align the way they’re meant to, even if it’s hard to watch.


As leaders, that means not just trusting your team but also trusting yourself to manage the weight of the role you’re in.


In leadership, balance is the silent skill that defines how effectively you’ll lead through the ups and downs. It’s the intentional practice of holding both success and struggle in the same space and finding your stride.


It’s not easy, but if you commit to practicing balance every day, it’ll make all the difference.


Keep going.


 
 
 

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