When I was 16 years old, I got the coolest job in town (or at least I thought so Reader).
I can still remember what I was wearing (a cyan blue zip-up hoodie and jean shorts) when the owner, Deb, handed me three white T-shirts with an ice cream cone on the chest and hired me on the spot.
We stood in front of the big white paper calendar on the back wall, and she put my name on the first month of shifts.
I was officially a Dave's girl (which, to me, was the equivalent of being a small-town celebrity), and I got to work at my favorite ice cream shop (because they had waffle cones with chocolate and sprinkles on them).
I was over the freakin moon.
Little did I know this job would teach me so much about running a business... and even more about what I didn't want for my future.
Or that for the next seven years, I would live by that big paper calendar in the back office.
It was a simple system that dictated my summers.
Only so many girls were allowed to take off on any given day, and it was on a first-come, first-served basis.
So most of my late teens and early twenties were spent picking and choosing a couple of concerts I could go to or a weekend I could drive up to the river - texting eight people just to try to cover one shift if something came up.
Over the years, I was able to hack the system a little. I was the first girl in in the spring, which meant I got first dibs on days off. But my life revolved around work. And although I loved my job, made pretty good money, and made lifelong friends there, it got old.
(Naturally, I got a serving and bartending job with even worse hours).
The Turning Point
Starting Cedar June meant changing all that ↑.
Finally, I got to dictate my work calendar and put life first. The calendar didn’t control me anymore - I controlled it.
I already had the vision for what i wanted my life to look like. And now I got to map that vision out on a calendar and make it happen.
Annual planning quickly became this former paper planner girlie’s favorite time of year. I could create any kind of year I wanted, any calendar, any schedule. I was obsessed.
Maybe - a little too obsessed?
I learned the hard way that planning isn’t about creating the perfect system. It’s about creating a sustainable one.
Let's dive deeper ↓
How to stop making yearly planning more work than it needs to be
(FROM SOMEONE WHO USED TO MAKE IT MORE WORK THAN IT NEEDS TO BE)
DISCLAIMER: I am a huge proponent of the fact that everyone learns differently. Different things work for different people. But when it comes to creating a sustainable and manageable strategy for the year, it is easy to make creating your calendar a lot more work than it needs to be (I should know—I’ve been there).
Here are some common planning pitfalls to avoid (+ where to start instead)
Too much detail (and not enough room for flexibility)
You’ll know you’ve fallen into this one if you’ve ever added a year's worth of deadlines and blog posts to your calendar in January in pen and realized the plan doesn’t leave you enough wiggle room by mid-February.
The perfect paper planner pit (and why it never works for you)
You’ll know you’ve fallen into this one if you buy a new planner each year, convinced it will change things, help you accomplish more & manage your time. But it’s on your bookshelf with blank weeks by March because you never actually took the time to break down the goals you have for your brand into a plan on paper.
The dry-erase calendar of doom
Maybe you’ve fallen into one of those pits from the past, so convinced (and quite possibly influenced by some big names in the online marketing space) you go DRY ERASE! The perfect year is laid out in 15 color-coded markers, and 4 hours later, you can change it! But then a month later - you realize changing one thing means changing everything - and you don’t have hours to make it all look pretty again.
Annual planning starts to feel like a fluffy waste of time that never actually helps you accomplish anything. And you would rather just take messy action and figure it out as you go than waste time on a strategy you can’t stick with.
Mid-year: You start to question that decision when you realize that you’ve only got six months left to make those ideas you had for your brand happen (ideally in a successful and profitable manner).
There’s gotta be a better way, right?
We're not just entering a new year—we're entering a new era of entrepreneurship.
With AI tools changing how we work and more people prioritizing work-life balance than ever before, having a strategic plan that prioritizes your life isn't just nice to have—it's essential.
January gives us a natural reset point, but more importantly, it gives us the space to plan before the year gets busy. Wait until March; you'll be too caught up in execution mode to think strategically.
After years of trial and error (and plenty of abandoned planners), I've finally cracked the code on creating a calendar that puts life first while still helping you reach those big brand goals (and how to make it work for you & the life you want to have off the clock).
I’m breaking down everything I’ve learned + how to make planning work for you in The Snowed In Strategy Sesh. A 2-hour live workshop where you'll walk away with:
- A life-first calendar for 2024 that YOU control
- Clear quarterly focus areas for your big brand goals
- A 30-day action plan to tackle your first behind-the-scenes brand project
- A sustainable planning system in Notion that grows with you
After this workshop, you'll:
- Feel confident about your 2024 plan (and actually stick to it)
- Know exactly what to focus on each quarter
- Have a flexible system that adapts when life happens
- Save hours of time trying to "figure it out" as you go
Lock in your spot for just $67 (regular price $107)
- Only ten early bird spots are available
- Offer ends December 31st or when spots fill
- The live workshop happens on January 15th
Here are some free resources to get you thinking about & strategizing for the new year in the meantime ↓
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END-OF-YEAR BRAND AUDIT
free brand audit mini-course
Learn how to audit your audience, content, and impact to create data about your brand that can help you make strategic decisions moving forward.
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GET CLEAR ON YOUR BRAND'S VISON FOR 2025
the rearview mirror
Closeout 2024 with clarity and start 2025 with purpose! This free 5-part email series and interactive Notion dashboard will help you reflect, plan, and create an inspiring, actionable roadmap for the year ahead.
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FROM TWDI ARCHIVES
update & align your brand's mission and vision
The 80/20 rule of branding and how your vision & mission should guide how you scale in 2025.
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