How to Rebuild Your Calendar Through First Principles

Everyone loves a fresh start. A blank, clean slate to start the year.

That’s what the New Year brings. And while it’s a great time to set big new goals, it’s also a great time to rebuild your calendar for the upcoming year.

Imagine building your calendar from scratch. All the previous commitments gone. All you have is a clean, beautiful empty calendar looking back at you 📅. What would you put on there?

Today I want to show you how you can rebuild your calendar through first principles, something I picked up from Taylor Holiday.

Let’s start building.

Quick Backstory

When I was knees deep learning about NFTs, blockchains, and web3, I was listening to any podcast I could find on the topic.

One of them was episode #332 from Ecommerce Influence, an interview with Taylor Holiday, managing partner at Common Thread Collective.

In the last few minutes of the interview, Austin asks Taylor – a managing partner, husband, father of three – a question about how he stays on top of everything:

📞 Austin: “You’re a busy guy. You’ve got lots of businesses to run. You have kids. How do you maintain your health, relationships, and other things outside of work while continuing to focus on work and driving your companies forward. Are there any things you’ve found over the past year that have helped you out?

In roughly 3 minutes, Taylor shares the 3-layer calendar cleanse process he uses to stay on top of everything going on in his life, personally and professionally.

I found it refreshing and a great framework for cleansing your own calendar going into the New Year.

Build Your Calendar Through First Principles

📞 Taylor: “It’s a matter of ruthless clarity and aligning your calendar with your values. I have this saying that I live by – ‘inner peace is when your calendar aligns with your values.’

Taylor goes on to explain the calendar cleansing exercise.

Every so often I wipe my calendar blank and reconstruct it through first principles of things that matter. I try to do it every couple months or whenever I feel myself in a place where I’m dissatisfied with the allocation of my time. I stop and clear it off and start from a clean slate.”

There’s something refreshing about the idea of starting with a clean slate. A fresh start. Imagine wiping your calendar clean from all responsibilities and commitments and building it up from scratch.

How would you rebuild your calendar? For Taylor, it’s about three layers:

What I’ll build first is self care because if I’m unwell then I can’t care for anyone else. Usually I work out in the morning, I’ve got this time with friends, I’ve got this date night with my wife. I’ve got this doctor’s appointment. Whatever the first things are, those go on my calendar as immovable objects first.

Then usually my wife comes second. What are the needs that I have in my relationship with her. Same with my kids. [My family] makes up my secondary layer of my calendar.

When I get to work, which is the third thing, what are the most important tasks that I can do that, as the CEO, are my primary responsibilities.

This is how you build your calendar through first principles. You start with the most important things and work your way down the list.

Here’s where you end up:

“What you get to is that the excess space then becomes the things that maybe you get to maybe you don’t. But the cost of not getting to these things is much lower than not getting to all those things I laid on first.

I love that last sentence – the cost of not getting to the excess things is much lower than not getting to the things you value the most.

This is what happens when you know what you’re optimizing for. You have clarity on where you want to spend your time time and what sacrifices you’re OK with making along the way. Your calendar simply becomes a reflection of that. It becomes a visual representation of your priorities.

But, over time, your calendar naturally begins to undo itself. New things get added. Important things get missed or forgotten. Priorities get abandoned.

This is where it’s important to recalibrate. This is why Taylor rebuilds his calendar every couple months or whenever he feels in a place where he’s dissatisfied with the allocation of his time.

It’s a necessary iterative exercise for better work and a better life. So give it a shot. This New Year, start from scratch. Rebuild your calendar through first principles and start the year right.

And if you find yourself discombobulated a few months into the year, simply cleanse again. Rinse. Repeat. And remember that it’s never going to be perfect.

“Does that mean I don’t get overwhelmed, of course not. Are there days I don’t allocate perfectly, of course there are. Are there days my kids aren’t saying ‘hey dad we gotta go to the trampoline park where are you’, yes. I have a wife who’s incredibly gracious and willing to give me feedback and people around me willing to do the same if I’m out of whack in a way that’s not serving them.”

Taylor Holiday

Go do big things this year 💯.