How to Build a Calendar You Can Trust Completely

1: Getting better at getting better is what RiseWithDrew is all about.

Monday through Thursday, we explore ideas from authors, thought leaders, and exemplary organizations.

At the end of each week, I’ve been sharing an idea from Tynan’s book Superhuman by Habit about how to install specific, positive habits into your life.

So far, we’ve covered:

2: “The problem with trying to keep appointments and events on a calendar is that unless every single one is on there, you can’t rely on your calendar,” Tynan writes.

“If you can’t rely on your calendar,” he notes, “then there’s no point in actually keeping one, because it’s taking up time and not relieving you of the mental load of having to keep track of things.”

Start by putting every meeting, appointment, and commitment on your calendar. No exceptions.

“Only once you reach that state,” Tynan observes, “will having a calendar be more of a benefit than a burden.”

Two important advantages follow.

First, it “drastically reduces the chance of missing and being late to appointments,” he explains.

Second, and maybe even more important, you free yourself from the mental stress of trying to remember everything.

“The key with a calendar, like emails,” Tynan writes, “is focusing on the first step and aiming for perfect adherence.”

Whenever you make a commitment, add it to your phone’s calendar immediately.

Always. 100% of the time.

“Later you can work on syncing with your laptop,” he states, “but since you know you’ll always have your phone on you, it’s a good place to start.”

When in doubt, add it to your calendar. It’s better to enter too many things than risk missing something.

Why? Because “you will only use your calendar if you trust it completely,” Tynan emphasizes.

3: As with any new habit, this may initially feel difficult, or even like a waste of time. At first, you’ll probably remember most of your commitments without checking your calendar.

But once “your brain trusts that your entire schedule is on your calendar,” he notes, “you will notice that you start referring to it more.”

It may take a month or two, but eventually you’ll begin relying on your calendar instead of your memory.

If you travel frequently, Tynan also recommends TripIt to organize flights, hotels, and rental cars. You can connect your travel plans to your calendar so they’re easy to find.

The bottom line? A reliable habit doesn’t just save time. It frees your mind to focus on more important things.

More next week!

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Reflection: How much time and mental energy do you spend trying to remember appointments and commitments instead of trusting your calendar?

Action: For the next seven days, immediately add every new appointment and commitment to your calendar. No exceptions. Begin building a calendar you can trust completely.