5-Minute Assessment

From Holiday Chaos to Holiday Joy: Why I Start Planning in September

boundaries fall season mental load time management work-life balance Sep 08, 2025

September hits and suddenly it feels like we're racing, fall schedules, school events, Q4 deadlines, and before we know it, we're deep in holiday chaos. Sound familiar?

For years, I thought holiday planning in September was overkill. Now? It's my sanity saver.

Let me paint you a picture of my old December reality: Two boys' birthdays (December 1st and 12th), my dad's birthday on the 2nd, my brother's on the 7th, hosting Christmas Eve dinner, coordinating with Santa, community donations, teacher gifts, and all the regular holiday magic I wanted to create for my family.

I was commuting into the city, carrying the full mental and emotional load of the season. And I mean ALL of it: budgeting, buying, wrapping, planning, cooking, cleaning, volunteering, decorating, RSVPing, showing up. My husband didn't love the holidays back then and struggled with the stress of it all, so he opted out. I felt alone, depleted, and like I was failing, not just at home, but in how I felt in my own body, mind, and spirit.

The worst part? We never made a financial plan for the holidays. Everything went on a credit card. Come January, we were thousands in debt, I was resentful, and we were already arguing about the following year.

I wasn't enjoying any of it. I was too busy doing all of it.

The Turning Point

After one especially stressful holiday season, I hit a wall. I remember saying: "I'm done doing it this way. I can't keep living in this loop."

So we sat down, and for the first time ever, we made a real plan.

It wasn't perfect at first. The shift took a few years to really feel different. But now, years later, I love the holiday season. I look forward to it. I feel grounded and excited instead of overwhelmed and overdrawn.

Why September is the Real New Year

Mel Robbins talks about how this time of year resets our routines, new school schedules, packed calendars, and a shift in energy. But I've learned that it doesn't have to come with chaos.

For our family, January through March is slow and quiet. But September through December? That's our marathon season. And if I don't intentionally plan for it now, I know what will happen: the same cycle of stress and burnout.

September, for me, is when I start preparing for the rest of the fall on my terms.

The Three Pillars of My September Reset

  1. Brain dump everything: Get it all out of your head and onto paper
  2. Set the financial foundation: Plan for spending before the spending starts
  3. Prioritize your non-negotiables: Know what matters most before the chaos begins

What This Creates

When I do this kind of planning in September, I show up differently in November and December. I feel:

  • Calm
  • Present
  • Energized
  • Regulated
  • Clear on my boundaries and decisions

It also makes it easier to say "no" to things that don't align, and say "yes" with full presence when they do.

And that, for me, is balance.

Preview What's Coming

This is just the beginning. Over the next three weeks, I'll be sharing:

  • The exact brain dump process I use.
  • My step-by-step financial planning strategy.
  • How to create boundaries that protect your peace.

With love,

Erin