We’re all just learning how to let go

The plan is rarely the reality. Here’s how I’m coping.

If you’ve seen my Instagram Stories this week, you know our first Kindergarten drop-off did not go how I pictured it.

It was intense. No cute first day of school sign pictures. My son instead was full-on sobbing, clinging to my leg, and it took three adults to pull him off me once inside the classroom.

I walked away trying not to cry myself, and honestly, I felt like I’d totally failed him despite feeling like we prepared as best I could.

But that’s how parenting is, right? It almost never goes the way you planned.

After that first day, I leaned hard into what I could control: my morning routine. Each morning felt like a full day by 7:50am. I got up on time (no snooze), did my workouts… even with little bodies climbing on me mid-plank, and made sure I got dressed and did my makeup so I could flip into work mode when I got home.

And that walk to school every morning got a little easier each day (with just one set-back).

On that walk, there was this one house we passed every day. Same scene each morning: a mom in sweats and oversized sweatshirt, hair undone, trailing behind her teenage daughter who was getting into the driver’s seat of their car. And the mom would just sort of hang there for a second, waive and watch her leave.

Monday, we exchanged a look. I was holding my crying son’s hand, and she gave me this kind of “I’ve been there” smile. Tuesday, when my son was all smiles and totally fine, she smiled again like, “you made it through.” And Wednesday, we finally said hello.

Turns out, her daughter just got her license. This was the first week she was driving herself to school.

It hit me. Two moms in totally different chapters, but both doing the same thing in our own way: figuring out how to let go a little.

This week reminded me that change always stretches us. Whether it’s the first day of Kindergarten or the first time your kid drives off on their own, it’s still that same mix of pride, nostalgia and discomfort.

I’m reminding myself not to rush through the hard parts just to get to the easy ones. That tough Monday made the calm, happy drop-off on Friday feel like a real win. The tears made the smile even sweeter. And learning to let go is what makes room for what’s next.

Seasons shift. Our routines change. But there’s something special about noticing it all as it happens and deciding to roll with it instead of resist it.

Currently

WATCHING The Hunting Wives I was skeptical, but ended up binging this show our first two weeks home. It’s a yes for me.

COOKING KaleJunkie’s Marry Me Chickpeas this is going to be on our rotation, great for an end of week, low grocery inventory meal since its almost all pantry staples

BUYING BeautyPie Tubing Mascara restocking, love how this removes in tubes, my eyes are watery and it doesn’t smear

LISTENING Aspire with Emma Grede feat. Allison Ellsworth Allison says “It’s so hard when you have momentum, if you pull back because… you’re having to fundraise, to get that momentum again. It’s probably one of the most difficult things in business.” This is sticking hard with me.

SHARING 5 Things I’m Doing So Back-to-School Doesn’t Suck If school is about to start, read this.

All The Things

I’m spotlighting work bags that will take you from school drop off to the office (whatever that looks like for you). These are vetted to fit a 14in MacBook Pro laptop. Shop many more in the full edit here.

• 🐫 Camel: Cuyana Oversized Linea Bag Cuyana is my favorite workbag brand, I wish I could own the whole store

• 🍫 Chocolate: Mango Suede Shopper roomy, soft, and chic enough to carry everything (snacks, laptop, etc.)

• 🫒 Green: Massimo Dutti Split Suede Bucket the perfect slouch in the dreamiest shade of green

• 🖤 Black: Madewell Soft Grain Tote classic, versatile, and under $200, an everyday win

New Modern Mom Podcast Spotlight

It’s my husband’s podcast debut and you don’t want to miss this behind-the-scenes episode, the first of many, talking about our financial plan that ultimately led us to quit our tech jobs and scale a Pilates business.

TLDR, here’s what you’ll take away from this episode:

💬 Redefining Financial Freedom as a Couple — Why creating your own definition matters more than following trends

🔥 FIRE, But Make It Realistic — How to adapt Financial Independence principles without losing joy today

💡 Bridging Money Mindsets — Practical ways to align when you and your partner have different financial habits

📈 From Reactive to Proactive — The apps and systems that make financial planning actually doable

🛠 The Money Date Blueprint — A 4-step guide for calm, productive money talks (even if budgeting isn’t your thing)

❤️ Don’t forget to give this a little love

This takes 1 sec, helps the newsletter grow, and motivates me to keep writing! And if you found this valuable, I’d love if you also…

• 💬 Leave a comment to share your back to school experience… did it go well? was it tough? Did you try any strategies I shared last newsletter?

• 📤 Hit ‘Share’ to send to your group chat

Thanks for joining me on this journey,

Barbara