Holding Both · Leadership & CaregivingLeading and loving without certainty.
I’m Maria Messer — Speaker, Writer, and Leadership Consultant for the people holding things together while figuring it out.
Who am I?About me
I’m Maria—a writer, a mother, and a leader shaped by experiences I never would have chosen. My life has been marked by love, loss, and long seasons of learning how to stay present when nothing feels certain. I write from inside those moments, not after they’ve resolved, because I don’t believe life arrives with clean arcs or clear lessons. Holding Both grew from this truth: that grief and joy, strength and tenderness, responsibility and humanity often live side by side—and that there is real courage in naming what’s unfinished.
Alongside my writing, I’ve spent my career leading in public education, working closely with complex systems, real people, and decisions that don’t fit neatly into boxes. I know what it means to lead when the stakes are high and the answers are incomplete—when children, families, and professionals are all carrying more than one thing at a time. My writing and speaking live at this intersection of lived experience and leadership, offering a steady place for those navigating complexity, leading through uncertainty, and trying to stay human while doing work that matters.
How I Can HelpHere Are 2 Ways I Can Help You
I lead and I love. I do both without certainty.
I lead and I love. I do both without certainty. For over twenty years I've worked in special education - everything from paraeducator to executive director. I'm also the adoptive mother of two boys from foster care, both with complex needs. The professional and the personal aren't separate - they teach each other. What I've learned in both is this: you don't have to be certain to be steady. You just have to keep showing up. This is where I work with the people doing the same.
For LeadersLeading When the Map Runs Out
If you lead in special education, healthcare, social work, nonprofit, or any setting where the calls are impossible and the map keeps running out, I work with you on what it actually takes to stay steady.
The work draws from three shifts:
Move from control to engagement
Hold more than one truth
Normalize the hard
We use them as a frame for the real questions you're sitting with right now.
Keynotes and Workshops
Holding Both - Leading When the Map Runs Out. For conferences, leadership teams, and organizational events.
1:1 Coaching
A six-session engagement structured around the three shifts. For senior leaders ready to stop performing certainty.
Team and Leadership Coaching
3 to 6 month engagements that build the three shifts into your team's shared language. For leadership teams burning out making impossible calls.
For FamiliesParenting Without Certainty
If you're raising a child with complex needs - disability, mental health, trauma, or some combination - I work with parents who are tired of doing this alone and exhausted by a system that won't tell them what's available
The work draws from the same three shifts:
Move from control to engagement
Hold more than one truth
Normalize the hard
Reframed for what it actually takes to parent without certainty.
Workshops
Navigating systems and securing the services your child can access.
Small Group Cohorts
For parents who need community and a framework, not another expert telling them what to do.
1:1 Coaching, Including Grief Work
For parents grieving the family they imagined while showing up for the one they have. Six sessions structured around the three shifts.
For complex leadershipYou’re In the Right Place If...
You lead people, and the situation in front of you doesn't have a clean answer.
You're raising a child whose needs don't fit neatly into the systems built to serve them.
You're tired of leadership advice that assumes the leader has it together.
You believe the hard and the hopeful can travel together - and you want language for what you're already doing.
You want to be steadier without pretending to be certain.
You Don't Need a Better Map
You need a different way of standing in the unknown.
Discover the three shifts that help leaders, parents, and caregivers move through uncertainty with greater steadiness, honesty, and confidence.
Life & LeadershipThe Space Between Certainty and Care
Holding Both is a space for leaders and families navigating complexity—where grief and joy, certainty and doubt, strength and tenderness exist side by side. I write about and speak about leadership shaped by motherhood, loss, and the reality that our lives, our work, and our kids don’t fit neatly into boxes. This work is for those learning to lead without a map and for families living in the in-between—staying present when clarity disappears, holding responsibility and humanity, steadiness and vulnerability, at the same time. If you’re leading, loving, or parenting in complexity—and feeling the weight of it—you belong here. If you’re a leader or a parent navigating a life that doesn’t fit neatly into boxes, you belong here.
The Holding Both Substack
A weekly Substack on leadership, parenting, and what it takes to stay. Essays drawn from twenty years in schools, a decade of complex caregiving, and the memoir in progress. For leaders and caregivers who want something honest in their inbox.
