*We are continuing our experiment with a longer form email structure. Less quick + easy, more deep + thoughtful." Would love to hear your thoughts!

---

You're reading this because you know the power of transitions. Maybe you're an ED planning your exit, a board member preparing for leadership change, or a funder watching organizations navigate the uncertainty of what comes next.

Today's conversation is about something we rarely discuss: how to give everything to work you know will end.

My guest, Wellesley Michael, managed Vice President Kamala Harris's digital communications accounts during the final months of the Biden-Harris administration. She knew her job had an expiration date—January 20th, 2025. What she didn't know was whether that date would mark the beginning of a Harris-Walz administration or the end of their work entirely.

The Paradox of Temporary Commitment

Here's what Wellesley told me that can shift how you think about endings and transitions:

"I love to know when the finish line is. That doesn't make it easier, but from an anxious person's standpoint, sometimes it is helpful. I know when the end date is, so I know I can do the work from where I start."

She's right. And she's also describing something most of us experience but won't admit: finality can be a gift.

Think about your organization:

• How many programs operate without clear endpoints?
• How many board terms blur into undefined commitments?
• How many EDs stay simply because there's no succession plan forcing them to think about what's next?

We confuse permanence with stability. But Wellesley's story reveals something else entirely.

Even in her previous role in the House, where job security was theoretically longer, Wellesley instead decided to live by intern cycles. Every few months, a cohort arrived. Every few months, they left. Pictures with the chairman. Last day celebrations. Then the cycle repeated.

Wellesley created endpoints where none existed.

For your organization, this might look like:

• Designing board terms with intentional sunsets and celebration rituals
• Building program cohorts with clear graduation moments
• Creating "passing the crown" ceremonies when leaders transition

The theater kid in Wellesley knows this instinctively—rehearse, perform, close the show, throw a wrap party. Repeat.

The Invisible Labor of Legacy

Wellesley's job was to ensure Americans understood the full breadth of VP Harris's vice presidency. Not the candidacy. Not the campaign. The four years of work that "people didn't give her credit for or know about."

She did this work tirelessly while managing grocery delivery because she couldn't figure out when to eat. While her friends held birthday dinners where she showed up with her laptop. While watching office doors in the White House marked "closed" as colleagues departed one by one.

The jump scare came when the presidential portraits changed. "Those are my parents," she'd think, waving to the wall each day. Until suddenly they weren't.

This is the work of legacy in real-time. Documenting contribution while knowing your contribution might not change the outcome. Amplifying impact while your own life becomes unrecognizable.

Sound familiar?

Every ED creating that succession binder. Every board member documenting institutional knowledge. Every program director ensuring the community understands what happened here, even if no one's watching.

The Grief Comes in Waves

Election night. The days unable to get out of bed. The quiet hallways. The portraits. The protesters outside her apartment.

But also: her friend opening her home to anyone who needed not to be alone. Her boss reviewing resumes and truly meaning "I'll be a reference." Her colleague getting the job, working one floor below her now in the Senate.

The peace revealed itself in pieces.

"There's peace that comes with endings, truly. It might not be immediate peace... but it continues to reveal itself in little ways."

Your Work as Only 50% of Your Legacy

Here's what I keep thinking about: We're only about 50% in charge of our own legacy. The rest is what others take from our time and impact.

Vice President Harris was only in charge of so much. Wellesley was only in charge of so much. The rest belongs to what we—the public, the movement, the next administration—do with it.

The same is true for you:

• The ED who builds systems that outlive your tenure
• The board member who creates the pathway for new leadership
• The funder who invests in transition planning, not just programs

You do the work. You document the impact. You create the conditions for what comes next. Then you release it.

Practical Wisdom for High-Stakes Transitions

Wellesley's advice for anyone doing temporary, high-impact work:

1. Basic life logistics matter. Where do people get food? What's the coffee shop? Where's the pharmacy? These aren't small things when you're dropped into crisis response or time-bound roles.
2. Be as clear as possible about outcomes. Even if clarity is hard, give people something to work toward so they know what success looks like.
3. Find people who will give you grace to be the version of yourself that the work demands, even when that doesn't feel authentic.
4. Remember that complacency isn't an option. The work continues. Always.

The Question For You

What if knowing the end date isn't the problem? What if instead, knowing the end date is actually the clarity that creates your most focused, most impactful work?

Your interim ED role, your board term, your program cycle—these aren't limitations. They're containers for your full presence.

The finish line isn't something to fear. It's permission to show up completely, knowing you'll Leave Well when the time comes.

Listen to the Episode

Chat with us about this on LinkedIn

​

Until next time,

Naomi

---

About Leaving Well: I provide interim leadership, proactive sabbatical policy launch, and succession planning for nonprofits ready to normalize workplace transitions. Because people leave—and it's not a crisis if you plan for it. Reach out to support@8thandHome.com