You've been on the hook for years. Maybe decades. You know every system, every donor relationship, every staff member's work style. You can troubleshoot the database in your sleep. Board members text you on weekends. You are the institutional memory, the firefighter, the one who starts big projects, and the closer.

I believe that you are diminishing your organization's accountability to its mission every single day you stay this way.

This is the accountability paradox: the leader who won't get off the hook becomes the organization's greatest liability. Not because you're doing bad work—you're probably exceptional—but because your indispensability is a structural failure pretending to be dedication and commitment.

Who in your organization is on the hook for what? And do they actually know it?

Most nonprofit leaders can't answer this question clearly. Not because they're bad leaders, but because organizational accountability is rarely mapped explicitly. We operate on assumptions, inherited norms, and "that's how we've always done it" instead of clear, documented agreements about who holds which hooks.

Getting off the hook isn't a knowledge problem. It's an identity problem, a trust problem, and a fear problem wrapped in professional responsibility. Let's distinguish between healthy disengagement and actual abandonment. Let's address the guilt, shame, and fear keeping you from stepping back. And let's get specific about what you actually owe your organization when you transition responsibilities—versus what your anxiety tells you that you owe.

Every leader leaves eventually. Retirement, new opportunity, burnout, termination, death—there are only so many ways a tenure ends, and all of them end. The question isn't whether you'll exit. It's how you'll handle the accountability of exiting well.

This is where theory meets reality. You've mapped your hooks, built capacity in your team, and practiced healthy disengagement from responsibilities you've held too long. But when you're actually leaving the organization entirely, a different set of obligations emerges—and a different set of fears, guilt, and complications.

What do you owe your organization during your final months? How do you balance loyalty to the mission with your own career needs and boundaries? What happens when the board hasn't found your replacement and you're already checked out emotionally? What about when you're not choosing to leave—when you're being pushed out?

Buffett announced in May that he'd retire December 31, 2025, giving Berkshire Hathaway seven months of structured transition planning. He’s stated that he plans to continue going into the office every day, and will become the Chairman of the Board.

While I never recommend departing CEOs and Executive Directors stick around beyond two weeks, one month at the most, Warren Buffett’s retirement announcement still holds many lessons for nonprofit board of director members!

Here's what nobody tells you: the type of interim leadership you choose doesn't just fill a gap—it shapes whether your organization exits this transition stronger or barely survives it.

Let's break down your three main options: full-time interim EDs, acting EDs from your current staff, and fractional executives. Each serves different needs. Most boards pick based on cost or convenience. Smart boards pick based on what their organization actually needs right now.

After four seasons and nearly 100 episodes, I'm closing the Leaving Well Podcast. Not because the work is done—it's not. But because seasons end, and this component of the Leaving Well library is ready to wrap..

Over the next several months, I'll release the final Season 4 episodes. These conversations with leaders and experts carry the same clarity, care, and courage that made me fall in love with hosting this podcast in the first place. But before we get to those, I want to share what this journey has taught me about the very thing I set out to explore: Leaving Well.

The math is simple. Replacing a burned out nonprofit executive director costs two to three times their annual salary when you factor in search costs, onboarding, and lost institutional knowledge. A sabbatical costs significantly less than that turnover. So why are we still having debates about whether rest is "worth it"?

Target recently revealed the succession planning question every nonprofit board needs to answer: Should the person who helped create your failing strategy be the one to fix it?

Target's board promoted COO Michael Fiddelke to CEO after 11 years of market share losses to Walmart, Amazon, and Costco. This wasn't crisis management (even though the social media posts will tell you otherwise!), this was a planned succession (however, planning doesn't guarantee success).

(Also ... the outgoing CEO will remain the Executive Chair of the board of directors ... sigh!)

Here's a strong opinion: strong Operations leaders don't automatically become strong strategic leaders / visionaries, and your nonprofit doesn't have Target's "luxury" of expensive succession experiments.

Most organizations resist getting help until they're already in pain. As someone who's spent years providing interim leadership and succession planning for nonprofits, I've heard every objection in the book. Today, I'm addressing the elephants in the room: We're fine as we are, We tried consulting before. It didn't work, We can't justify the cost, We're in the middle of too much change already, It will disrupt our operations, and We can handle this internally.

Transitions don't have to be scary. They can be beautiful opportunities for growth, clarity, and renewal. But only when you're prepared. Start where you are. Begin the conversations. Build the systems. Your future self—and your organization—will thank you.

The question isn't whether your organization will experience leadership transitions. The question is whether you'll be ready when they happen.

The Dallas Cowboys Cheerleaders have choreography for the kick line—but not for the goodbye. I unpack the Netflix docuseries and explore what it reveals about leadership transitions, legacy traps, and the danger of having no plan for "what’s next." Whether you're leading a nonprofit or sitting on a board, you need to hear this breakdown: why “churn” is not the same as “transition”, how legacy leaders without a succession plan risk collapse, what it means to evaluate performance without care, and how Leaving Well can help your organization do it differently.

Glitter doesn’t cover grief, and turnover without care is just change in sequins. If you’re a nonprofit leader or board member, this is your call to rethink succession before it becomes a crisis.

 A CEO steps down after a viral scandal, and within 72 hours, a new interim leader is named. While the world focused on the drama, we’re focusing on what really matters: how Astronomer’s board pulled off one of the fastest leadership transitions we’ve seen.

Nonprofit leaders: this is your wake-up call. Learn why internal leadership benches matter more than dream candidate lists, why speed is more important than perfection during a crisis, how to craft crisis communications that inspire confidence (not chaos), and why your mission must stay front and center, even in moments of disruption. Whether you’re an Executive Director or on a nonprofit board, this is your playbook for succession readiness—before a crisis hits.

Portland's WNBA team has a chance to model what interim leadership done right looks like with Clare Hamill. Success will be measured not just by hiring a permanent president, but by:

• Building organizational systems that prevent future leadership crises

• Establishing the cultural foundation necessary for long-term success

• Creating sustainable talent development and succession planning processes

• Restoring stakeholder confidence in the organization's competence

For nonprofit leaders watching this unfold, the lesson is clear: Your next leadership transition is coming whether you're ready or not. Portland's $125 million learning experience doesn't have to be yours.

The question isn't whether you'll face leadership transitions—it's whether you'll manage them strategically or let them manage you.

Anna Wintour just announced she's "stepping down" as Vogue Editor-in-Chief after 37 years ... except she's not really leaving. As Condé Nast's Chief Content Officer and Vogue's Global Editorial Director, she's created the perfect example of succession planning gone wrong.

In this article, I break down why Wintour's transition is actually "succession theater" - and why this leadership mistake is costing organizations millions across every industry.

At its core, my Leaving Well work is about creating a world where leadership transitions aren't organizational emergencies but expected moments of transformation handled with intention and care. Where leaders can be fully human – arriving, contributing, and eventually departing without trauma. Where the handoff of responsibility strengthens rather than weakens our collective impact.

Because the truth is simple: how we leave matters just as much as how we lead.

The concern that an interim leader "won't know the culture or mission" isn't a limitation—it's precisely where the value begins. As an intentional outsider, I bring fresh eyes unclouded by organizational history or internal politics.

This external perspective allows me to:

• Surface hidden opportunities that have become invisible to those immersed in daily operations

• Address long-standing challenges that may have been normalized or worked around

• Ask the questions no one internally feels safe raising

My Interim ED / Interim CEO approach isn't about imposing external solutions but rather serving as a "method actor" who quickly absorbs and adapts to your organizational context.

Black holes are often compared to feelings of anxiety–the closer you are to its center, the more it draws you in, and nothing can escape from it. We can’t even observe anything that enters the black hole. It absorbs everything, even light. 

Nothing can travel faster than the speed of light, so once something is pulled into the gravity of a black hole, it’s never going to get out again. The boundary–the line that once crossed cannot be escaped–is called the event horizon. 

Put in simple terms, nothing that enters a black hole can be observed from outside the event horizon.

A connected concept known as the “Anxious Event Horizon” provides important and necessary understanding when dealing with uncertainty that lies ahead. At its core, the anxious event horizon represents the juncture at which the unknown meets human apprehension. As we approach this boundary, this line to be crossed into the uncertain future, we may experience a surge of anxiety, triggered by impending change, ambiguity, or potential risk. This surge can manifest as stress, fear, or overwhelm. 

The term "horizon" emphasizes the boundary between what is known and what lies beyond, a space where anticipation and unease often intersect.

In a professional context, the anxious event horizon can arise during significant transitions, mergers, leadership changes, or shifts in organizational strategy. Individuals grappling with changes in job roles, organizational restructuring, or shifts in industry trends may also encounter this horizon. This phenomenon is not limited to the workplace; it extends to personal life changes such as relocating, pursuing higher education, or embarking on new relationships.

Navigating the anxious event horizon requires a multifaceted approach that blends psychological awareness and practical strategies.