Knowing When to Walk Away: A Leadership Dilemma
“In the process of letting go, we can begin to see what we’ve been holding on to that no longer serves us.”
– Martha Beck
We have all felt the vast difference. Leaving a meeting or dinner with customers or your friends on a complete high, your bucket is full. The other side of the spectrum is the cycle of feeling drained from the energy vampires that make it all so difficult. How do you know when it’s time to walk away? From an opportunity, from a customer, from a relationship? It’s arguably one of the most challenging aspects of leadership and personal growth.
For much of my life, I’ve struggled with this. Maybe it’s my eternal optimism or my deep-rooted belief in seeing the true potential in people and situations. I’ve always wanted to believe that, with the right effort and perspective, things will work out. But lately, I’ve found myself becoming more skeptical, questioning whether that belief still holds weight. Expectations fall short. Efforts go unnoticed. Value and energy are not always reciprocated.
And that’s when the negative rabbit hole starts calling. It’s easy to feel justified in frustration, to build a case for why something, or someone, isn’t worth our time anymore. There will always be people ready to validate those feelings, to confirm that you should give up, walk away, or demand better.
But before making that decision, I’ve had to remind myself to step back and ask a harder question: Why do I do what I do? Why am I the way I am?
If we are truly operating within our values—doing things because they feel right, not just because we expect something in return, then why the cynicism? Often, ego gets in the way. It whispers about fairness, about keeping score, about how much we’ve given versus how little we’ve received. But real leadership, real self-alignment, means giving because it aligns with who we are, not because of what we might get back.
That doesn’t mean we shouldn’t have boundaries. It doesn’t mean we blindly invest in situations that deplete us. But it does mean that when we choose to give, we do it for us, for our own integrity, not for validation.
So, does believing in people’s good intentions make it any easier to walk away when something isn’t working? Not necessarily. It still stings. It still leaves us questioning whether we should say our piece or simply take the high road. But the real question is: What is the intention behind our final words or actions? Are they to seek closure, to make a point, or to uphold our values?
For me, the answer to when it’s time to walk away has become clear: When staying compromises my own values. When I no longer feel invested. When it no longer feels right in my head and heart.
Because in the end, walking away isn’t just about leaving something behind. It’s about making space for what aligns with who we truly are.
