News / Articles

Keep Dreaming

Nurtured Mommy
KEEP DREAMING

By: Denise E. Bailey | September 2, 2025

Many years ago, I wrote an article encouraging mamas to simply Trust Your Gut when choosing a preschool for your child. My original inspiration came after a tremendous amount of gratitude and relief from finding our preschool community. We had relocated from Marin to Sonoma County to be closer to family in 2017 and then ended up moving back to Marin in 2021. This same article was edited and re-published in 2024, with gratitude for finding a school community for our daughters to complete K-8th. We thought this was the place our children would live out their childhood.

Our twins were thriving in a class filled with love and acceptance by their peers, teachers, and parent community…but sadly our oldest didn’t have the same experience. I kept thinking that if I just tried hard enough, then I could find a way to help her class bond (parents and students) and this would, in turn, help her to fit in. That never happened. I tried and I tried, but I failed and in the midst of it all, she lost herself. It was the scariest thing to watch unfold as a mama. Pulling two children from a community where they are truly happy and excelling felt foolish at times. It was like I was on a roller coaster of emotions with a high of hope and wonder and then back down into regret and fear. But, we are a family and we stick together.

All of these big decisions were coming to a head shortly after I exited my husband’s company. I spent almost four years helping him launch and run an impact fund. I loved learning about the world of finance but my heart longed to be back in education. I interviewed at so many places and toured so many schools, both as a potential employee and parent. It was fascinating. Marin truly has many amazing public, charter, private, and independent schooling options. It felt like I was doing a collegiate research paper on school cultures, pedagogies, and communities but this time through the lens of a parent. And slowly, by early Spring, we started to get acceptances to schools where I also received offers.

I was scared to death to choose wrong. I was spinning because I thought that I had already chosen right. And I wondered who I was to re-enter education after so many years away. I had to quiet my mind, give myself grace, and mourn all that I was leaving behind. I also had to trust my gut, dream differently, and manifest what I knew in my heart was better for all of us. Well mamas, growth isn’t just for our babies. You are not off the hook. In fact, I would argue that motherhood sparks the biggest phases of growth we’ve ever really been through and unknowingly signed up for. We are on this journey with them, learning just as much as we are teaching.

So, here we are a few weeks into the school year. I thought I was going to be back in the classroom, but ended up in an administration role. I am working with families by helping them through the admissions process and it feels right. After helping my parents and husband with their business, I am finally back in the field which warms my soul. I am overjoyed that my babies are with me everyday. My ten-year-old self dreamed of being a teacher where my children went to school. My twenty-nine-year-old self remembered and went back to school to become an educator after working in the event industry. My forty-four-year-old self remembered that I could still make big changes with courage and be on a path I envisioned for my family even before it existed. It took me a minute to figure out when I was out of alignment but then, almost magically, it all divinely (or universally) unfolded.

You are still brilliant, confident, strong, kind, and worthy of the life you dreamed of even though I know you are holding that baby in your arms. It’s okay, keep dreaming and trust your gut.

Denise is third generation Marinite who is dedicated to vulnerably discussing the not-so-pretty parts of this beautiful role of motherhood. She is inspired by her three daughters to help women manage their expectations, let go of perfectionism, and lean into their enoughness. Denise is a certified Early Childhood Educator (ECE) with a K-8 Multiple Subject Clear Credential who has taught it all from preschool to middle school. She works in an admissions role for a Toddler-8th grade Southern Marin independent school and has been writing for The Crier since September of 2021.