We Didn't Turn Out OK with Jennie Monness

60: From School Admissions to Building Life Skills


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In this episode, I sat down with my friend Brooke Parker, someone who started as an Instagram connection and quickly became one of those rare, deeply trusted mom friends.
We met in the most “New York mom” way possible - sitting across the hallway from each other after having our second babies. Fast forward four years, our kids ended up in the same preschool class and became incredibly close… and so did we.
Brooke is an early childhood educator turned consultant, helping families navigate the often overwhelming (and very imperfect) private school admissions process in NYC. Through her work, she not only guides parents toward the right fit for their child, but also works directly with kids to help them feel confident, capable, and prepared.
But beyond her professional lens, Brooke is that mom friend - the one everyone texts about everything. From products to transitions to “what do I do in this moment?” - she somehow always has an answer. It’s what led her to create her platform, @justaskbrooke, where she shares practical, thoughtful guidance for every stage of childhood.
In this conversation, we get into:
- Why she believes preparation (not perfection) is the foundation for confidence
- Her biggest “no’s” (including no wipe warmers, skipping sippy cups, and ditching the stroller earlier than you think)
- How to introduce a new sibling in a way that actually supports both children
- The small, intentional choices that build real-life skills over time
We also talk about something I find so compelling about Brooke, how she approaches parenting and life with a level of thoughtfulness and organization that feels grounding, not overwhelming, making sure to share the imperfections with her children as teachable moments.
This episode is full of tangible takeaways, but also something deeper: a reminder that when we prepare our children (and ourselves), we give them something much more lasting than ease - we give them confidence.

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We Didn't Turn Out OK with Jennie MonnessBy Jennie Monness

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