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.

NEWS FLASH: Most employers and organizations do NOT handle resignations well. Sometimes it’s for security reasons. Sometimes a manager is just petty. Sometimes it’s somewhere in between. 

But most organizations have prioritized hiring and onboarding… while not doing much to prepare for offboarding and departures. So this process can be a pain for EVERYONE involved. 

Alison Green’s Resignation Checklist (10 Things to Do Before You Resign) article in The Cut was a smash in 2023, outlining ten ways for employees to protect themselves during their departure, including pre-emptively saving contact info and performance reviews, deleting personal files and emails, and more. 

I found that I had more to add to her advice, so I created my own resignation checklist with a Leaving Well twist. Read more to learn more!

The Catholic Church's papal conclave – the intriguing smoke-signaled process of selecting a new pope – represents history's most enduring succession system. Whatever your feelings about Catholicism itself, there's something remarkable about an organization that has weathered 2,000 years of transitions.

So what can we learn from this process? Quite a lot, as it turns out. This is the first article in a series of six, with this first article exploring the foundational structure and process elements of the conclave, as well as examining how having pre-established processes, deliberative space, and clear closure rituals benefit succession planning.

The papal conclave, despite its dramatic flaws, creates conditions for relatively healthy succession politics. It doesn't eliminate human ambition, factional interests, or information asymmetries – but it channels them in ways that typically prevent catastrophic outcomes.

What if we designed succession processes that acknowledged political realities instead of pretending they don't exist? What if we created structures that channeled political energy toward institutional health rather than factional victory?

This isn't about importing red hats and secret ballots into your boardroom. It's about learning from a system that has managed succession politics – however imperfectly – for two millennia.

The conclave represents perhaps the world's most extreme example of gender exclusion in succession planning. No woman has ever cast a vote in a papal election. No woman has ever been considered as a candidate. No woman has ever been present in the room where it happens.

This isn't just an interesting historical quirk, it's dangerous and harmful. It also lets us into the reality of uncomfortable truths about succession planning in organizations far beyond the Vatican.

In papal transitions, the ceremonial destruction of the previous pope's ring – the "Fisherman's Ring" that served as his personal seal – symbolizes a clean break between pontificates. This dramatic act communicates unmistakable transfer of authority but also represents an institutional commitment to discontinuity rather than knowledge preservation. In the movie Conclave, someone is shown removing the top section of the pope’s ring, using some tools to detach what looks like a seal from the ring itself. 

Most organizations don't literally destroy symbols of previous leadership, but many create similarly abrupt transitions. The departing CEO cleans out her office on Friday; the new one arrives Monday morning. The founder makes a dramatic farewell speech and disappears from the organization entirely. The executive director hands over keys without sharing the unwritten knowledge that makes those keys useful.

The papal conclave offers valuable lessons in both directions. Its procedural clarity, supermajority requirement, and crisis resilience demonstrate remarkable strengths. Its historical episodes of legitimacy crisis, political capture, and knowledge transfer failures reveal vulnerabilities that even sophisticated systems sometimes experience.

By learning from these cautionary tales across sectors and centuries, we can develop succession approaches that anticipate common failure patterns rather than simply hoping they won't occur in our organizations.

"Leaving Well" means approaching departure with the same care and intention as arrival. It means recognizing that how you leave profoundly shapes your leadership legacy. It means understanding that your final act of leadership may be your most consequential – the graceful transfer of authority to those who will carry the mission forward without you.

The papal blessing "Urbi et Orbi" (to the city and the world) offers a fitting metaphor for the dual responsibility that succession represents. Leaders owe thoughtful succession both to their specific organizations ("the city") and to the broader purposes those organizations serve ("the world"). When we approach succession planning with this expansive sense of responsibility, we transcend individual ego to serve something larger and more enduring than ourselves.

"Norman doesn't have an exit strategy. We just take one day at a time. We hope that if anybody would take over the store, they'd keep the same employees. He's built up a reputation of honesty, trust, fairness, and trust. People rely on him."

Sound familiar? This statement from Norman's Rare Guitars documentary reflects what I hear constantly in my work with nonprofit leaders. The denial and refusal to prioritize any form of succession planning remains remarkable. Leaders build incredible organizations, develop deep expertise, and cultivate decades of relationships—yet leave their legacy to chance.

Every person’s experience is different when it comes to leaving a job, but I’ve seen a lot of people try to make a job work long after they realized it wasn’t a good fit–mostly because they didn’t want to disappoint anyone or let people down at work. 

But your first priority must always be your own wellness, so this article is all about how to protect your heart before and during the decision to leave a job, especially if you want to Leave Well.

81 percent of workers say they will be looking for workplaces that support mental health in the future. Transitions are part of that support. When we ignore how people leave, we are also ignoring how people stay well.

Have you ever noticed how much energy we pour into beginnings like onboarding, welcome lunches, and new initiatives, but how often we overlook the endings?

Most of us don’t stay at our first job. We’ve left roles. We’ve stayed behind after a colleague moved on. So why are we still so uncomfortable talking about departures?

Strategic planning gets filled with what’s urgent, while the important work of preparing for transitions falls lower and lower on the list. Until a moment comes and it will come when you’re suddenly navigating grief, confusion, and a thousand unanswered questions.

Here’s the truth: interim leadership doesn’t just buy time. It offers clarity. And succession planning isn’t about predicting the future. It’s about stewarding it.

We can use practice and ritual to help address burnout in the workplace. If your gut is telling you that you need something different, what practices and rituals can you start working on today to help support that future decision?

The number one topic I’m asked to speak on is values. Yet, more times than I can count, when I ask organizational leaders about their values I often receive blank looks in response. 

Values are not just words up on the wall–they are essential to a nonprofit organization’s operations, along with a mission and vision that speaks to what we’re here to do, how we do it, and how we’ll know when we’ve accomplished our goals.

Leaving a job is hard enough for those of us with healthy coping skills and boundaries. It can be a minefield of emotional navigation for folks with a history of people-pleasing. People-pleasing isn’t just being a “yes man” and volunteering for more than one’s fair share. It’s often based in long-seated trauma. You’ve probably heard of the “fight or flight” response, but there are two other possibilities when facing danger–freeze and fawn.

When it comes to Leaving Well, I help organizations prepare for leadership gaps, but still feel strongly that you can Leave Well even when you’re an individual who has been fired or made redundant. 

Losing your job is one of the most stressful things we can experience–whether you are fired, laid off, or in some other way dealing with a loss of income and benefits. This is a time that brings up an immense spectrum of reactions big and small. You may feel depressed and disappointed. You may have intense worry, fear, or grief. You may also feel a sense of failure, confusion, and anger. All of them are valid! 

Unfortunately, many of us never learned how to acknowledge, process, and talk about difficult emotions. And if we can’t speak about what we’re going through, we can perpetuate the stress and grief of job loss rather than working through it.

I recently spoke with author Dr. Jaiya John about the individual ways that people connect in workplaces and our global obligations of mutual care between all living things. His book Your Caring Heart: Renewal for Helping Professionals and Systems and his work centers indigenous teachings about mutuality, care, and community. As a social psychologist, he has spent years visiting organizations and institutions that reached out to him for support with staff morale, burnout, and an overall sense of unwellness–this is the work that led to Your Caring Heart.

I know enough to be dangerous: When someone, typically in a position of authority, has basic competency in doing something, but they are unwilling to admit they don’t have the necessary knowledge or expertise for the task at hand.

Not only is this phrase a load of nonsense that showcases a dangerous knowledge gap, I believe that “I know enough to be dangerous” is actually a tool of weaponized incompetence.