Your Calendar Is Already Full… The Question Is With What?
March 24, 2026

Let’s talk about your calendar.
Not the tool itself.
Not the app you use.
But how does it get filled?
Because for most people, calendars don’t get planned…
They just fill up.
Meetings get added.
Obligations pile on.
Deadlines appear.
And before you know it, your days, weeks, and even months are spoken for, without much thought about whether those things actually matter to you.
So today, I want to challenge you:
What if you filled your calendar on purpose?
Start With What Matters Most
When I look at my year, I don’t start with work.
I start with what matters most in my life.
For me, that includes:
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Our annual summer trip to Vermont with friends
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My son’s school schedule (finals, vacations, major milestones)
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Family priorities and important life events
These go into my calendar first.
They are not optional.
They are the foundation.
Everything else gets built around them.
Build a Life – Then Fit Work Into It
After those anchor points are in place, I look at:
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A couple of fun trips each year
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A few professional development opportunities
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Space for spontaneous moments (because those matter too)
Things like:
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A girls’ weekend
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A last-minute trip
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A show in New York
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A weekend in Newport
That flexibility is intentional.
Because a life that’s too tightly scheduled leaves no room for joy.
Don’t Forget Life Maintenance
Then there are the things we all need to take care of:
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Annual doctor’s appointments
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Home maintenance (like servicing the furnace)
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Routine checkups and responsibilities
These may not feel exciting, but they’re essential.
And when they’re scheduled ahead of time, they don’t become stressful last-minute problems.
Protect the Moments That Matter
Here’s where intentional planning really becomes powerful.
For example:
Next year, my son is graduating from college.
That’s not just another date.
That’s a moment.
So I’m not planning anything else during that time.
No launches.
No major commitments.
Just presence.
Because when you don’t plan for what matters, you risk missing it.
The Truth About Your Calendar
Your calendar is not just a scheduling tool.
It's a reflection of your priorities.
And if you don’t decide what goes into it…
Other people will decide for you.
Keep It Simple
You don’t need a complicated system.
You don’t need fancy software.
You already have everything you need:
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Your phone
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Your email calendar
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A simple planning habit
What matters is not the tool.
It's the intention behind how you use it.
The Real Question
So here’s what I want you to think about:
If you looked at your calendar right now…
Would it reflect the life you actually want to live?
Or just the life that happened to fill it?
Start there.
Because when you plan your life first, everything else starts to fall into place.
As always, what I hope for you is that you live a life you love without giving up the things that bring you joy.