The Cost of Holding On: Why Leaders Must Master the Art of Letting Go

In business, adventure, and life, there’s an undeniable truth: growth requires endings. Yet, many leaders—myself included—resist them. We cling to relationships, projects, or strategies long past their expiration date, fearing the discomfort of letting go. But as Dr. Henry Cloud emphasizes in Necessary Endings, pruning is essential. Not just for plants, but for people, companies, and careers.

I recently learned this lesson the hard way. I stayed in a relationship—both personal and professional—that should have ended long ago. It was a bad mix from the start, but I kept compromising, convincing myself that the personal connection outside of work justified sticking it out. I ignored the red flags, made excuses, and held onto hope that things would shift. But here’s the hard truth: if someone truly values you, they won’t require a professional transaction to stay in your life.

This person kept me around because they needed my skills, not because they valued them—or me. And that’s on me for allowing it. I should have recognized that staying in that situation wasn’t loyalty—it was self-betrayal. And as Cloud says, false hope is the enemy of progress.

Endings Are Hard - But Indecision Is Costlier

One of the greatest pitfalls I see in leadership and business strategy is the reluctance to cut dead weight. Maybe it’s an employee who isn’t growing into their role, a partnership that no longer aligns, or a legacy system that’s hindering innovation. We hold on, hoping things will magically improve. But hope, Cloud reminds us, can be dangerous when it keeps us tethered to something that’s clearly failing.

High performers don’t waste time propping up things that should be left behind. They assess, decide, and act—understanding that pruning is painful but necessary. Because clarity and forward momentum are on the other side of decisive endings.

The Leadership Skill You Can’t Afford to Ignore

Leaders who struggle to make tough cuts often tell themselves:

• “Maybe it will change with time.”

• “I don’t want to hurt anyone’s feelings.”

• “We’ve already invested too much.”

But this mindset doesn’t serve you—or your team. Holding on to the wrong things robs you of time, energy, and resources that should be fueling growth.

Endings must be intentional, not reactive. Strong leaders don’t just let things fade away; they make the hard call. They:

1. Define their non-negotiables – What aligns with their mission, vision, and long-term goals? If something doesn’t, it’s dead weight.

2. Use data and patterns, not emotions – Have things improved? Or is there a cycle of unmet expectations? If nothing has changed, it won’t magically start now.

3. Take action swiftly – Prolonging the inevitable only drags down performance and morale.

Your Actionable Takeaway: The ‘Necessary Endings Audit’

This week, audit your commitments, personal and professional. Ask yourself:

• What am I holding on to that no longer serves my goals?

• Where am I making excuses instead of making a decision?

• What (or who) am I afraid to let go of, even though I know I should?

Then, act. Have the hard conversation. Make the clean break. Close the door so you can open the right one.

Because growth isn’t about holding on—it’s about having the courage to let go of the wrong things to make room for the right ones.

About Jenn - The Patriot Angler