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One Hour to Dream: Making Room for Your Organization (and Yourself) in 2027
There is always something else to finish.
One more donor conversation. One more report. One more board meeting. One more thing you would love to move off your desk before the year ends.
As an executive director, you know how quickly the last weeks of the year can become an exercise in closing things out. And while that work matters, I want to invite you to make room for something that matters, too.
Somewhere in the last 45 days of 2026, give yourself one hour to dream.
Not to finalize your strategic plan. Not to build a funding calendar. Not to turn every possibility into a task with a deadline.
An hour to think about what you want for your organization, and how you want to show up to help make it possible.
Whether January begins your fiscal year or simply marks a new calendar year, this time of year is an opportunity to pause. To look beyond what needs to get done and reconnect with what you hope your work will make possible.
But before you look forward, take a moment to notice how far you have already come.
Before you dream, recognize your growth
What moved forward in 2026?
Not just what you finished. What did you learn? What conversation did you finally have? What relationship grew stronger? What did you handle differently because of the experience you have gained?
Some progress is easy to put in an annual report. Some milestones are much quieter.
Maybe you asked for help sooner. Maybe you became clearer about what your organization can (and cannot) take on. Maybe you protected your staff's time, made a hard call, brought in a new donor you had been working to connect with for months, or stopped treating every request as an emergency. Maybe you took a week off for no reason at all.
Your brain likes recognizing its progress, and the more you practice this habit, the more it will default to seeing your wins before automatically troubleshooting into solving the next problem.
Give yourself a few minutes to write those things down. And for the high achiever, no, you do not have to finish everything on your task list to recognize that you have moved forward.
Then…turn toward the year ahead.
1. Name up to three big, beautiful dreams
What do you want to see become possible for your organization and the people you serve?
Do not edit yourself.
Do not make the dreams smaller because you cannot yet see the funding. Do not turn them into SMART goals. Do not start assigning responsibilities.
Let them be big, audacious, and beautiful.
Maybe you dream of a space where your community feels welcome. A team that has the support to do its best work. A program that reaches people you have not yet been able to serve. An organization that is financially stable enough to make decisions from purpose, not urgency.
You do not have to accomplish the entire dream in 2027. For now, simply ask whether it is something you want to move toward.
Journal prompts
What are three dreams I have for this organization?
What would become possible for our community if we moved toward them?
What am I almost afraid to write down because I cannot yet see how it would happen?
2. Ask what your well-being needs
Now bring yourself into the picture.
Not just yourself as the executive director. Yourself as a person with a body, relationships, responsibilities, energy, and limits.
When you look at these dreams, what do you notice? Excitement? Exhaustion? A little of both?
You may love the dream and still recognize that something about how you are working needs to change.
Maybe you need a clearer boundary. Maybe you need rest, support, or time that is not already spoken for. Maybe you need to stop being the person who steps in every time something is unfinished.
That does not make the dream less meaningful. It gives you something important to consider as you work toward it.
The question is not, “How do I give more of myself until this happens?”
It is, “What would help me show up with the energy, creativity, and steadiness this dream deserves?”
Journal prompts
What about my current way of working supports my well-being? What depletes it?
What boundary or support would help me lead with greater intention?
What do I want to protect in my life as I work toward these dreams?
3. Consider how you want to learn and grow
Look at your dreams again. Then look at what you wrote about your well-being.
What might you need to learn?
This could be a technical skill: understanding financial reports, building a revenue strategy, or using your organization’s data more effectively.
It could also be a softer skill like learning to delegate, navigate conflict, ask for what you need, or let someone else approach the work differently than you would.
Do you see the connections?
A dream for a stronger team might connect to your need for more rest, and your opportunity to become more comfortable sharing responsibility.
We sometimes need to compartmentalize our lives. But for this hour, give yourself permission to see how your leadership, your health, and your personal hopes for the organization relate to one another.
Journal prompts
What knowledge or skill would help me move these dreams forward?
What kind of person would I need to become, or what would I need to believe about myself, to make this dream a reality?
Where might I need to lead differently rather than simply work harder?
What would growth look like if it supported both the organization and my well-being?
4. Identify the people you want alongside you
You are not dreaming for an organization that exists only in your head. You are part of a community of people who care about its future.
Who needs to help shape these dreams? Whose perspective is missing? Who could challenge your thinking, offer support, or help carry the work?
Write down names if you have them. Write down types of people if you do not.
A trusted peer. A board member. A community partner. Someone with lived experience of the issue your organization addresses. A mentor. A professional who can support your health.
Some of these connections may support the dream directly. Others may support your learning or your ability to stay well while leading.
Journal prompts
Who should help shape these dreams—not just help execute them?
Whose experience or perspective do I need to hear?
Who can support my growth and well-being along the way?
Close with a connection, not another task list
Before you finish up your hour, read what you have written.
Where do you see connections among your dreams, your well-being, your growth, and your relationships? If you used a pen/paper, bust out that highlighter and make the connections.
Choose one small step that honors those connections. A conversation. A boundary. An invitation. Time set aside to learn.
And ask yourself: How do I really want to show up as I help move this dream forward?
You do not have to become a different person to deserve a bigger dream. But you can give yourself permission to grow: to release a habit, practice a new skill, or become more comfortable leading in a way that once felt unfamiliar.
You are not here simply to complete a task list in 2027.
You have hopes for your organization, your community, and the impact you can create together. Give those hopes some room. Give yourself a place in them.
Then take a step toward them, even if it is a small one.
PDF Worksheet: One Hour to Dream: Making Room for Your Organization (and Yourself) in 2027
Related reading and research
Heller, Cathy. Abundant Ever After. Simon Element, 2024.
Heller, Cathy. “How to Allow in Abundance & Stretch Towards Your Next Level.” Podcast episode, May 6, 2024.
Boyatzis, Richard E. The Science of Change: Discovering Sustained, Desired Change from Individuals to Organizations and Communities. Oxford University Press, 2024.
Amabile, Teresa M., and Steven J. Kramer. “The Power of Small Wins.” Harvard Business Review, May 2011.
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