The One More Year Trap
For Executive Directors who can’t stop saying ‘just one more year.’”
By the time you admitted you were thinking about leaving, you’d already stayed “just one more year” at least three times.
It started out small. “I’ll get us through this federal grant renewal.” But then the grant came through, and next up, a strategic plan. It didn’t feel fair to leave without launching that either. A senior staff member resigned, and then a major funder wanted more visibility. Then the board wanted a deep dive into financials. And then, and then…
Each time you got close to saying, “I think my season here is ending,” something urgent “popped up.” So you waited. And it’s so tempting to continue because it seems so rational.
If you’re familiar with the Financial Independence crowd, you’ll be familiar with One More Year (OMY). If not, it’s that you have technically saved enough to leave work, but you keep moving the finish line ($ number) you need to feel confident in your financial plan.
In the nonprofit world, there’s a version of this as well. You know your time as Executive Director is winding down, but you keep pushing the conversation off because the organization could use improved systems, the board feels dependent, or your identity is deeply wrapped up in being the one holding all the strings.
It’s a bit like you’re working with one foot on the dock and one foot on the boat. And with almost half of current nonprofit leadership at or nearing retirement, that’s a lot of people with one foot on the dock, one foot on the boat.
So how do you know you’re actually ready?
I think you are ready to leave the Executive Director role when the facts say yes in three places:
1. Your personal life. Not perfect. Ready enough.
You know what it costs to live. You know how you’ll fund it. You know what the first version of your next chapter looks like. You don’t need to have your retirement planned out to the nth degree. Just an idea of what you want the first version to include.
2. Your organization. Again, not perfect. Ready enough.
There is a written transition path for the organization. Critical knowledge has been captured/transferred. Key relationships are more distributed. If you stepped out, the place might wobble temporarily, but it would not collapse.
3. Your spirit is ready enough.
You can talk about leaving without spiraling. You may still feel grief, but underneath it there is clarity. When you imagine staying three more years, you feel dread. When you imagine leaving well, you feel excited.
That’s your checklist. If the answer is yes in all three places, you are probably not looking at a someday question anymore. When all three are ready enough, you are standing at the starting line of leaving well. Because another twelve months of the same patterns will not magically make your departure easier. Time itself does not mean leaving well.
The question can then shift from “Should I leave?” to “How do I use this next year to hand things off with intention?”
What does it mean to Leave Well?
Leave well to me means a deliberate transition to a desired state. A transition that designs for what’s next. You can leave suddenly because you’re exhausted and something snaps. You can leave slowly, with one foot on the dock and one foot on the boat, for years. Or you can Leave Well by shaping the year so that the organization and your successor are better prepared.
A year might sound like a long time. But think back to this time last year. Does that seem terribly far away? Now imagine a succession year. A year you choose on purpose, where you and your board practice what it will mean for the organization to live well after you. A succession year is a practical container for leaving well.
When you and your board both know change is coming “eventually,” but nobody is willing to anchor it to a real timeframe, the organization doesn’t become more stable. It becomes more suspended. You start maintaining more than you’re building. You patch systems instead of redesigning them. You keep stepping into gaps instead of insisting the system carry its own weight.
Nonprofit Boards of Directors often avoid succession planning because they don’t want to lose you. They don’t want to face the work. They don’t want you to feel like they’re pushing you out.
If you wait for them to be brave first, you might wait forever. If you set a timeline and say, “Let’s plan this together,” you give them something solid to stand on. Your Board of Directors is responsible for managing leadership transition. But you are responsible for being clear about how much time is included.
Breaking the One More Year cycle starts with one decisive move. You choose a date on the calendar. Not “someday.” Not “when it feels right.” A date. Once there’s an exit date, you and the board can start shaping the work around it.
Now you can imagine milestones of:
Your board will have a clear, written succession and transition plan
Your organization will be less dependent on you in the exact places that make you most anxious now
Your successor can arrive into clarity
You see a life on the other side
If you’re looking at retiring, a succession year also has a very practical to-do list on the organizational side. You already know where the weak points are. If you left next month, you could probably rattle off exactly what would break first.
That “break first” list is a big part of your succession roadmap. Leaving Well is mostly about working that list on purpose, over time. Yet none of this has to be overcomplicated.
I’ll be sharing my full succession planning process over the next few weeks. And I keep it simple.
I think leadership succession is either Planned or Unplanned. And it can have an additional component of Founder or Crisis, which you weave into either the planned or unplanned roadmap. Honestly, that’s it from my perspective.
Importantly, and often skipped, there’s the human side of succession. Whether you execute a planned or unplanned exit. Without incorporating the human side of transitions, your successor arrives in a foggy, anxious, overfunctioning system. There’s no clear story. People are braced for impact (and not the good kind) instead of being curious about the next chapter.
This essay is about a Planned exit. But strong organizations should have a plan for an Unplanned exit. Even though that sounds redundant. How is a goal of an unplanned plan a good thing? You’ll find out in follow-on essays.
The Gift and Your Legacy
A year of succession practice offers something different for the people connected to your nonprofit organization.
They get improvement
They get the mission they count on
They get a board that has thought through what is needed next for the organization to thrive
They get staff who’ve had time to ask questions and adjust
They get a former exec who has done some of their own letting-go ahead of time
And you don’t have to wait for the work to calm down to earn your exit.
There will always be another grant cycle, another board retreat, another key hire, another crisis that makes it feel “not quite time” to go. The finish line will keep scooting just out of reach as long as you keep letting urgency, fear, or loyalty redraw it for you.
You cannot control every twist in how the transition unfolds. Boards change. Funding changes. People have feelings in all directions. But you can decide that your last year in the role will not be another year of maintaining and patching. You can decide it will be the year you share the exit date, work your plan, and leave well.
Leaving Well is how you step out of that One More Year loop on purpose. It’s how you move from living with one foot on the dock and one foot on the boat to choosing solid footing for both you and the organization you’ve given so much to.
Cheering you on!
About Me:
My first Executive Director role almost cratered me. And now I share all my hard-learned lessons of successfully leading a nonprofit organization in The Pocket COO. Through a newsletter and private membership that helps 1st-time Executive Directors lead confidently, exiting Executive Directors leave well, and Boards of Directors manage the transition.
Here I pour my love of strategy, tactics, cadence, and the magic of intentional use of your time so you rock your mission and build a workday you love. You can turn your nonprofit strategy into action, achieve consistent funding, and offer a place people clamor to work in a sector typically defined by overload.
❤ Thanks for reading :) I’m here to help you on your nonprofit leadership journey. To lead confidently, grab my made-for-you templates or book a 1:1 Office Hours session where we dig into your specific challenges and goals.
“You know what the first version of your next chapter looks like.” Love this because it’s so true. You just need the first version.