When Leadership Means There Is No Win on the Horizon
Leadership often gets painted as a game of wins and losses, but the truth is messier. Sometimes, no matter what choice you make, you walk away with bruises.
Enter Disney and the ongoing Jimmy Kimmel Live saga.
Disney pulled Jimmy Kimmel Live off the air after FCC Commissioner Brendan Carr threatened a new investigation over comments Kimmel made about the death of conservative activist Charlie Kirk, according to Variety reporters Selome Hailu and Cynthia Littleton.
If you’ve been living under a rock:
- Nexstar, the largest TV station owner in the country, announced it would pull Jimmy Kimmel Live from 32 ABC stations unless Kimmel apologized for his comments.
- Sinclair Broadcast Group joined the chorus, leveraging its influence over dozens of affiliates.
- Protesters gathered outside Disney’s Burbank headquarters, ABC’s Hudson Yards offices in New York, and the Hollywood Boulevard theater where Kimmel tapes, chanting “Down with the FCC” and “ABC bent the knee.”
Disney’s dilemma was brutal: keep Kimmel on air and risk losing affiliates and government retaliation, or bench him and risk appearing spineless, fueling protests and damaging brand credibility. There was no clear win.
And that is the reality for leaders today. Whether you are running a company, building a personal brand, or leading a team, there are moments when every path feels like loss. But these moments—painful as they are—are also defining.
Tactical Leadership Principles for No-Win Moments
So how do you lead when the scoreboard says there is no win in sight? These five tactical principles offer clarity.
#1: Choose the Option With the Best Story
When outcomes are murky, narrative becomes your compass. The My First Million podcast host Shaan Puri sat down with “Side Hustle King” Chris Koerner to discuss this very concept. When you reach a fork in the road, choose the option with the best story.
Why? Because when the dust settles, people rarely remember the details. They remember the story of who you were in that moment.
For creators and entrepreneurs, the same applies. Turning down a lucrative brand deal that does not align with your values may sting financially, but it strengthens your long-term narrative of integrity.
When there is no win in sight, ask: Which decision will make the best story five years from now?
#2: Reframe the Problem
No-win situations feel suffocating because they force binary thinking. Option A or option B. Both are bad. Disney’s internal debate was likely framed as: Do we anger affiliates and risk FCC retaliation? Or do we pull Kimmel and face accusations of censorship? Both are poison.
Great leaders reframe the problem. A better question might be: How do we reaffirm our commitment to free expression while acknowledging diverse perspectives? For creators, reframing might look like this: instead of asking, “Do I risk losing followers if I speak on this issue?” ask, “How can I deepen trust with the followers I most want to keep?” Reframing shifts the focus from survival to strategy.
#3: Anchor to Core Values
When every decision looks bad, values are the compass. Core values guide you when strategy fails. If your non-negotiable is authenticity, hiding behind polished statements erodes trust. If your non-negotiable is fairness, choosing convenience over justice corrodes credibility.
A tactical leader asks: Which option best reflects my values, even if it costs me? Sometimes the only way to “win” in a no-win situation is to stay true to yourself.
#4: Optimize for Long-Term Trust, Not Short-Term Applause
In crisis, the temptation is to choose the path that quiets the noise. Disney’s decision to bench Kimmel may have offered short-term relief from affiliates and regulators, but it fueled louder, longer-lasting backlash.
Quick fixes rarely outlast their costs. Leaders who emerge stronger from crises optimize not for applause in the moment, but for trust over time. This means resisting the urge to play it safe just to silence critics. Speak in a way that builds credibility, even if it earns fewer claps in the moment.
#5: Communicate the Journey, Not Just the Decision
In no-win moments, silence is costly. People will fill the vacuum with their own assumptions, and those assumptions are rarely flattering. Disney’s lack of transparent communication about Kimmel left critics to control the narrative. Protest chants like “ABC bent the knee” became the story.
Contrast that with leaders who narrate the journey. Creators who share openly about burnout, pivots, or failures often find their audiences more loyal. If you cannot offer a clean win, offer transparency. Say what you considered, acknowledge the tension, and share your reasoning. People will forgive imperfection, but not being left in the dark.
Three Lenses for High-Stakes Situations
The Strategy Lens: Define the field before you play. Step back and ask: Is this really the hill to die on? Or is it a distraction? Strategy distinguishes between the urgent and the ultimate.
The Story Lens: Consider how this will be remembered. Audiences rarely recall details, but they remember your stance. Leaders must ask: What headline will define me when this is retold later?
The Stewardship Lens: Protect what outlasts the moment. You may lose money, followers, or goodwill in the short run. But if you preserve trust, credibility and influence, you are still ahead.
Final Thought: Leadership as Narrative Stewardship
The Disney–Kimmel–FCC showdown shows what happens when leaders face a no-win scenario under public scrutiny. The ultimate outcome is still in the works, but the lesson is timeless: when victory is evasive, narrative stewardship is your best tool.
When your next no-win moment arrives, do not just ask, “How do I win?” Ask, “Which story do I want told about how I led through this?”
