Hey, it’s Ryan…
In this issue, I’m sharing the simple annual planning ritual my wife and I complete every year to “save the date” for what matters most before the craziness of the New Year creeps in.
Here’s what you’ll learn:
How I plan our year without starting with goals
The simple way I decide what gets first claim on my calendar
Why “save-the-date-calendar-blocking” beats perfect planning
How we make room for family, work, and rest without overthinking it
The one question that instantly reveals if your priorities are out of whack
Let’s get into it…
P.S. I’m looking for 5 business owners who want to work 1-on-1 with my team and me to install a custom “operating system” in 2026, so your business can scale and so you can exit the day-to-day. Click here for the details.
Quick Hits
Here’s some other content from the Scalable network, plus some other cool stuff I liked and thought you might like, too:
🧰 Tool of the Week: This free “CEO Dashboard” template allows you to manage your entire business in just 14 seconds from a single spreadsheet.
🎓 27-minute MBA on how to build a business that can run without you. (a.k.a. I was on the My First Million Podcast)
❌ Your team is NOT your family. (If you make this mistake as a CEO, your best people will run for doors.)
👶 60 seconds on how to NOT raise entitled kids as a successful entrepreneur.
Every December, my wife and I repeat one simple ritual that sets the tone for the entire year.
We don’t set goals.
We don’t align on projects.
We don’t make “resolutions.”
We pre-load our calendar.
Because here’s what I’ve learned the hard way: If you don’t decide what gets first claim on your time, everything else will.
That’s why we follow what I call the Pre-Loaded Year…an annual planning ritual designed to save the dates for what matters most before the year fills up.
It’s built around a simple way of thinking about time:
Rocks are the can’t-miss days you’d regret losing.
Pebbles are important, but flexible.
Sand is everything else that expands to fill whatever space is left.
Let’s get into it…
BONUS: Here’s a walkthrough video showing exactly how we do this and breaking down my “Pre-Loaded Year” for 2026.
Step 1: Pre-Load Your Family Rocks
For me, family gets first dibs on my calendar, because how can I say my family is my “#1 priority” if all they ever get are the leftovers?
For us, that means blocking the non-negotiables first:
A 30-day family vacation every year
A shorter Spring Break trip
Multiple 1–2 week trips with just my wife and me
Major holidays and family traditions
Birthdays, anniversaries, and graduations
Sports tournaments, dance recitals, and other “can’t-miss” moments
I don’t need to know where we’re going or every detail yet. I just save the dates…because if I don’t, those days will get taken by something else.
Step 2: Pre-Load Your Work Rocks
Next comes work…but only the work that actually matters.
These are things like:
Strategic planning days
Major events or conferences I’m attending (or hosting)
Big product launches or campaign rollouts
Key hiring pushes
Board or investor meetings
Interestingly, some things most founders treat as “rocks” are pebbles for me now. Our quarterly planning sessions, for example, don’t require me to run them anymore, but yours might.
There’s no right answer. The rule is simple: block the days where your presence truly matters.
Step 3: Pre-Load Your Fun & Rest Rocks
This is the part most founders skip (and then pay for later).
Fun and rest aren’t optional extras…they’re fuel.
For me, this includes:
Golf trips
Personal travel
Fully unplugged days
Recovery time
Fitness events
For example, I want to play 50 rounds of golf this year. That’s basically 50 days, so if I don’t save those dates now, they won’t magically appear later.
Step 4: Pre-Load Pebbles and Sand
Once the rocks are in place, you can add pebbles:
Standing meetings
Focus days
Content days
Hobby days
Short trips
Sand—things like errands, admin, and inbox cleanup—doesn’t get scheduled upfront. It fills the gaps as time allows, which is exactly the point.
IMPORTANT: The goal is not to pre-load every day. Open space is part of the plan.
The goal is to save the dates for the things that truly matter.
Step 5: Check Your Ratios
Finally, I review my calendar and manually count the number of days committed to:
Family
Work, and…
Fun/Rest
Then I ask one question:
How does this feel?
There’s no perfect ratio, but if I say family matters more than work, I should see more days blocked for family rocks than work rocks.
In other words, my priorities should be reflected on my calendar.
That’s the ritual.
It’s not about perfection.
It’s not about micromanaging.
It is about intentionality.
Because in the end, show me your calendar…and I’ll show you your priorities.
⚡️ Action Step: Open your calendar and save the dates for one family rock, one work rock, and one fun/rest rock in the next 90 days. You don’t need details…just protect the time.
P.S. I’m looking for 5 business owners who want to work 1-on-1 with my team and me to install a custom “operating system” in 2026, so your business can scale and so you can exit the day-to-day. Click here for the details.
