Stop Persisting and Start Quitting
By Jeremy Clopton, Managing Director at Upstream Academy
Perseverance is a leadership strength — until it isn’t.
Persistence has long been celebrated as a hallmark of success. But here’s the hard truth: not everything deserves to be finished. In today’s fast-paced profession, the willingness to strategically quit might be one of the most underdeveloped leadership skills.
I recently had the chance to present this topic at the 2025 HeadWaters Leadership Conference. That’s right — an entire session dedicated to the fine art of quitting. And no, it wasn’t just a ploy to get people to leave early. (Though if they did, their commitment to the theme was applauded.)
Here’s the key question that guided the conversation:
When does perseverance stop being a strength and become a liability?
The Case for Strategic Quitting
Strategic quitting isn’t failure. It’s wisdom.
It’s not about giving up when things get hard or walking away impulsively. Strategic quitting is a calculated, proactive decision to ensure alignment with a firm’s goals, values, and long-term success.
When leaders persist in projects that are doomed, low-value, or morale-killing, they’re not being strong — they’re stuck. And that comes at a cost to everyone involved.
Why Do Firms Keep Going Too Long?
Before firms can learn to quit well, it’s important to understand what keeps them holding on. Common traps include:
- The sunk cost fallacy: “We’ve already invested so much.”
- Fear of perception: “Nobody wants to be a quitter.”
- Emotional attachment: “This is my baby.”
- Inertia: “This is how it’s always been done.”
- Hope as a strategy: “Tomorrow might be better.”
Recognizing these traps is the first step toward a healthier mindset — for leaders and the industry as a whole.
Three Mindset Shifts for Reimagining the Firm
- Prune for Growth
Ask: What needs to end for something better to begin? - Make the Competition Irrelevant
Ask: Where is the firm competing harder, when it should be competing differently? - Build Flywheels, Not Sinking Ships
Ask: What is building momentum, and what’s slowing the team down?
Six Ways to Build Strategic Quitting Skills
If quitting is a leadership skill (and it is), it deserves intentional practice. Leaders can start by:
- Normalizing conversations about strategic quitting.
- Building “kill criteria” into every initiative and knowing when to walk away.
- Modeling it from the top so leadership sets the tone.
- Re-evaluating clients, services, and projects with a renewal mindset.
- Holding autopsies without blame so failure isn’t fatal, it’s feedback.
- Making timely decisions even with imperfect information.
These practices help firms stop what’s not working and make space for what will.
The Challenge
What will your firm quit to make room for what’s next?
Before the end of August, consider having one quitting conversation. Let go of something that no longer serves your team, your goals, or your future.
After all, the profession can’t be reimagined by clinging to its past.
Sometimes, the bravest thing a leader can do is say,
“We’re done here.”
