I do not like bugs. AT ALL. Given the choice between a forest trail and a comfortable chair indoors, I have always chosen the chair, and I have never felt bad about it.

So it surprised me a little when I stood in a closing circle this August and heard myself say that my intention was to spend more time in nature.

Let me back up.

In early August, I spent three days at Wingspread in Racine, Wisconsin, at a convening for leaders of Chicago nonprofit organizations. The question at the center of our time together was a big one: how do we build organizational resilience in a time of constant change? Anyone leading in the nonprofit sector right now knows that question is not theoretical. Leaders have been making hard decisions about operations, staffing, and even mission, all while supporting teams who are carrying heavier workloads and real anxiety about what comes next.

What made this convening different was how it was designed. It was intentionally spacious. There was a kickoff dinner and a closing circle, and in between, we were invited to choose our own pathway. The time was meant to be whatever we needed it to be.

If you have ever been handed open time after months of back to back obligations, you know that can feel harder than a packed agenda. When nobody tells you what to do with your time, you have to decide. And deciding requires you to know what you need.

What I needed was to be with people, and to be outside.

On Thursday, those of us who had arrived early shared a relaxed lunch. On Friday morning, I went down to the beach near the lighthouse with a few of the other nonprofit leaders. I had praise and worship music playing, and the song that sat with me that morning was “God I’m Just Grateful” by Chandler Moore. I am grateful to God for many things, but in that moment my gratitude was simple. I was grateful to be alive. I was grateful to have work that made space for me to get away, because the work we do is mentally taxing, and that kind of space is not something I take for granted.

That night, we gathered around a fire. No one gave a speech. People shared about growing up in Chicago, about high school, about why they got into nonprofit work in the first place. When it started to rain, we moved indoors and kept talking about music, art, and the work we all do. It was refreshing to spend time with other leaders simply as people, without a problem to solve or a deliverable waiting.

Then came Saturday and the closing circle. Each of us named an intention to carry forward. We had been surrounded by so much nature that mine came almost without thinking. Be in nature more. Even though I am not an outside girl.

Here is what I know about intentions set at retreats. Most of them do not survive the drive home. I have been guilty of this myself. You leave inspired, you open your inbox, and within a week the retreat feels like something that happened to someone else.

I want to tell you what happened after, because that is the part that matters most.

Since August, I have been to the beach twice. I rode a swan paddle boat in Indianapolis with my family. I spent time at Northerly Island with my team. One Saturday morning, my family and I climbed the Swallow Cliff steps and then took a short walk in the woods.

And in September, I hiked three and a half miles.

That one needs some context. At LISC, we hosted a Day of Rest and Rejuvenation for our partners in the One Chicago for All Alliance at Pulaski Woods. There was something for everyone: forest therapy, fishing, painting, journaling, hammocks, card games, or simply relaxing at the pavilion. I chose the guided hike, 3.5 miles through the forest preserve and into a former top secret World War II research site. It was the first time I had ever hiked that far. After lunch, a teammate and I took a pedal boat out on Maple Lake, with two more pedal boats from our partner organizations on the water alongside us.

Me. The woman who does not like bugs. Three and a half miles in the woods.

When most of us hear the word rest, we picture stillness. A nap, a quiet room, a day with nothing on the calendar. Those are rest, and they are good. But rest is bigger than stillness. Rest is whatever restores you. Sometimes that is a quiet afternoon. Sometimes it is a hike you never imagined taking, a song on the beach, or a conversation around a fire that has nothing to do with deadlines.

Rest also is not only something someone else designs for you. Wingspread was a gift. Someone else planned it, hosted it, and fed us. But the beach trips, the paddle boat, and the Swallow Cliff steps? Nobody planned those for me. The retreat gave me the intention. Keeping it was my work.

Rest you are given is a gift. Rest you keep is a choice.

Every time I followed through on that small intention, I was doing more than getting fresh air. I was keeping a promise to myself. I have written before that consistency is quiet courage, and that the trust we build in ourselves comes from the moments nobody else sees. A Saturday morning on a set of stairs counts. So does a swan paddle boat.

Looking back, I think the intention held for a few reasons. It was small and specific. I did not promise myself to “rest more” or “find balance,” which are goals so big they are easy to postpone forever. I promised nature, which I could act on that same weekend. It was also a little uncomfortable, and that kept it honest. And I almost never did it alone. Nearly every outing included other people, so the time restored me and connected me to the people I enjoy being around at the same time.

I keep coming back to that morning at the lighthouse. In the Gospel of Mark, after the disciples returned from pouring themselves out in ministry, Jesus told them, “Come ye yourselves apart into a desert place, and rest a while.” (Mark 6:31 KJV) The scripture notes that so many people were coming and going that they did not even have time to eat. The invitation to rest came while the work was still unfinished. Rest was not the reward for finishing. It was part of the work.

That is worth remembering for those of us who lead. Hosting the day at Pulaski Woods reminded me that rest is not only personal. When we make space for our teams and partners to step away, we are telling them their restoration matters too. And it is hard to offer others something we have not learned to practice ourselves.

In It Was Never About the List, I wrote about stepping away from work without finishing everything first. This is the other half of that lesson: what you step toward when you step away.

So here is my invitation for you this week. Think back to the last time you felt restored. I do not mean the last vacation you planned. I mean the last time you came back to yourself. Where were you? Who was with you? Now name one small, specific way to bring a little of that back into the next two weeks. Put it on your calendar, and invite someone to join you if that will make it more likely to happen.

What is one small intention for rest you can set over the next 10 days, and who will you invite to keep it with you?

One more thing before you go.

Later this month, I’m a Featured Speaker at the Top 100 Most Powerful Black Women Summit, a five day virtual summit running October 19 to 23. My masterclass is called Own What You’re Building: The Work That Holds It Up. Through me, you can receive complimentary access, valued at $97, with replays included. When you register, enter Jennifer McClain where the form asks which speaker invited you. You can register here. I’ll share more in the coming weeks.

Not a normal list. A long one. Everything I could think of that still needed handling before I stepped away went on it. Emails I had not gotten to. Loose ends from the week. And then I would push myself to get through every line of it.

Working later than I meant to, on my last working day before vacation started. Staying at my desk past the point I had already told myself I would leave. Trying to check every box, one more, one more, until I got through a good chunk of the list.

And even on the times I finished the whole list, walking out that door never felt the way I thought it would. I expected relief. What I actually felt was tired in a way rest was not going to fix right away.

No matter how much I got done, there was always a reason to keep going. One more email that could still be answered before I logged off. One more task that felt important in that exact moment, even if it had not felt important an hour before. One more thing I told myself I could squeeze in, just this once, before I let myself leave.

It was not really about the list. Lists end, eventually, one way or another. This did not.

It was about how I was making decisions in that moment. Everything felt urgent. Everything felt like it needed me right then, before I could possibly step away and leave it alone for a week.

I know part of where that comes from. I have spent most of my career being the one who follows through. The one who handles things. The one people can count on to make sure it actually gets done. I am not saying that like a complaint. Most of it, I am proud of. But it also means I learned how to keep going long before I ever learned how to ask myself whether I needed to.

The Question I Started Asking

At some point, I had to stop and ask myself something more honest than whether I had finished the list.

Is this actually urgent? Or is this just how I have trained myself to respond?

Because the truth is, no matter how much I got through, there was always something else waiting behind it. Something else I could have added. Something else that could have been wrapped up if I had just stayed one more hour.

The list was never actually going to run out. I was going to run out first.

And I think that is the part that is easy to miss when you are the one who always follows through. You start to believe the urgency is coming from the work. Some of the time, it is coming from you.

Not Just a Vacation Problem

I do not think this is only a vacation problem. I think it is a low hum underneath a lot of ordinary days, for a lot of us.

You do not need my particular circumstances to know this feeling. You just need a life that is full enough, in whatever shape that takes for you, that most things start to feel like they cannot wait. That is most of us, more days than we would like to admit.

It is rarely about the list itself. It is about how many things have learned to speak in that same urgent voice, until we stop trusting ourselves to tell which ones actually mean it.

So I made a different decision. I still make the list. I do not think I will ever stop doing that, and I do not think I need to.

But now I actually look at it before I start working through it, instead of starting at the top and pushing until I run out of time. I ask myself which of these things actually needs to happen before I leave, and which of them just feels like it does because it has been sitting on the page long enough to seem important. And then I leave the rest there. On purpose. Without finishing it first.

That part is still not easy for me, even now. Some of what I leave on the list still nags at me a little, even once I have already decided to leave it there. But nagging is not the same as necessary, and I am learning to tell the difference.

Because here is what I finally let myself believe. The work will still be there when I get back. It always is. But my energy is not going to just be there waiting, however I happened to spend it. That is something I have to lead. On purpose, not by accident, and not because a list told me it mattered.

I still feel the pull some days. The one more email. The one more thing. I do not think that voice goes away completely, and I have stopped expecting it to.

What is different is that I do not automatically believe it anymore.

What is on your list right now that feels urgent, even though it might not be? And what would it actually cost you to leave it there, just this once?