How to Organize Your Calendar - The Ultimate Guide

- This video is sponsored by Skillshare.

If you wanna make better first impressions with people you meet,

build good relationships over time, and in general live a more successful life,

one of the simplest things you can do is be punctual.

Be where you're supposed to be when you're supposed to be there.

Of course that's easier said than done,

because most of us live pretty complex lives.

We've got class, we've got work, we've got meetings,

we've got secret backroom deals to get to.

So it's not always the easiest task to keep a perfect record of your

schedule up in the three pounds of mushy cranial material inside your head.

And honestly, you shouldn't even be trying.

As David Allen, the original productivity guru, once wrote:

"Your brain is for having ideas, not for holding them."

So today you, my friend, are entering calendar bootcamp.

Now, your calendar is a part of what I love to call the productivity

system,

which is the combination of external tools

that come together kind of like Voltron robots to form this cohesive,

real world source of truth for everything going on in your life,

and that includes tasks, ideas, contacts, and of course events.

So today I'm gonna teach you how to set up the calendar part of

that system so that it never fails you,

and accomplishing that goal means following three simple rules.

Number one, set up your calendar in a way that suits you.

Number two, add events and relevant information to those events.

And number three, get information out of your calendar at the right time.

And the right time might not be what you think it is.

So let's kick this off with rule number one:

set up your calendar in a way that suits you.

And that starts with choosing a calendar system in the first place,

leading us to the inevitable age-old question, what kinda calendar is best?

Physical or digital?

And if the answer is digital, what's the best calendar app?

Well, in the world of fitness there's this old adage.

"The best workout program is the one that you will actually stick to."

The most hyper-optimized program for Olympians is gonna be useless to you

if you don't enjoy it,

or if you don't have time to stick with it.

That's actually why I work with a lifting coach.

If I have a super busy week, or if I'm traveling,

Matt can just adjust my programming accordingly and I stick to my workout.

And the same is true for calendar apps and productivity apps in general.

The best one is the one that you'll actually use and stick to.

Now, personally, I like Google Calendar.

Some of my friends like Apple Calendar better.

My mom actually sticks with an old school wall calendar.

That works for her.

These are all legitimate choices,

because a calendar is really a personal tool that has one main job;

acting as that external source of truth for your life's events.

So as I mentioned earlier, Google Calendar is my personal calendar app of choice.

That's because it is free.

I can pull it up on my computer and my phone,

which is always with me, and that's nice.

Even my watch.

And it also has some integrations with other apps like SavvyCal,

which I use for scheduling meetings with other people and not doing email tag.

So for that reason,

we're gonna be using Google Calendar as the visual example in this video.

But I do wanna mention that there are some other great apps out there.

I've got a companion article for this video, and you'll see them listed there.

And in general, I will note that, again, for me,

I do think that digital calendar apps have some very compelling advantages over paper

calendars,

namely recurring event support and reminder support, which is very nice.

But if you wanna use a paper calendar,

or a paper planner like this one, that's totally cool too.

And there are some advantages to paper calendars

as well. - Do you always carry

that calendar in your pocket? - Yes. - For one,

it's pretty hard to get sucked into Instagram

or TikTok when you're adding an event into your paper calendar,

and also you can use markers and highlighters to make your paper calendar "aesthetic."

Now, one thing that I like to do

when I'm setting up my calendar is divide the different types of events in

my life into groups

that I call it "life buckets."

And this was especially helpful

when I was a student

and had a much more chaotic life,

'cause I had work shifts, I had class, I had exams.

I had on-campus events,

I had scheduled study blocks with study partners and friends.

Tons of different things going on in all kinds of different categories.

And I think a lot of you are gonna be in the same boat.

We live very complex, multifaceted lives in many cases.

So doing this just gives you some visual separation on your calendar,

and just gives you a better bird's eye view of everything you have going

on in your life.

Now, in Google Calendar, you can easily choose the color of each event,

and you can divide your events up into life buckets that way.

But I like to go one step further

and create an actual separate calendar for each of these buckets.

And that gives me a couple of different advantages.

Number one, I can set a default color for every single event type.

But number two, and more importantly,

I can set up default notification preferences for each of these different calendars.

And that's very useful because I sometimes do wanna get notified about events,

like for appointments, but I don't need notifications for every single event on my

calendar,

like scheduled self-study time in the morning.

I don't need to be notified about that.

I know I'm gonna do it.

Rule number two is to add events to your calendar, kind of obvious,

but also add relevant information to those events.

So in order for your calendar to be that trusted external source of truth,

you have to actually add events to it.

But for a lot of people, especially over the longterm,

that's kind of easier said than done,

because a lot of calendar systems have a lot of friction.

And when there's friction involved in a system, especially a productivity system,

we start getting tempted to just try to remember things.

We go against that David Allen advice from the beginning of the video.

We're trying to hold ideas in our head instead of externalizing them.

And that's not good.

So what we're gonna do in this section is go over several different tips

for getting events into your calendar painlessly

and with less friction,

but also how to make those events more useful to you as well.

And let's start with optimizing for quick capture.

In the world of productivity,

the idea behind quick capture is

that the faster you can get something into your system,

be it a task, an event, an idea, a contact,

the more likely it is that you're actually going to do so.

And there are a lot of tools out there

that try to optimize for this.

There are GTD style inboxes,

a single default place where you basically just dump everything

when you're on the go

and then process it later.

My Ultimate Tasks Task Manager Notion template has one built in for calendar events.

There are also some quick capture tools out there.

The one that I use personally is an app called Fantastical.

Now, earlier I said that I use Google Calendar as my calendar system,

but what I actually do is import those calendars into Fantastical,

which is both an iPhone app and a Mac app,

and what that gets me access to is Fantastical's natural language processing for adding

events.

And if you've ever used Todoist, you're probably familiar with this.

In Todoist you can type out all the details of a task in the

quick add bar,

and if you have a project tag or a due date,

Todoist will parse that information and add it where it's supposed to be.

And Fantastical has the exact same feature.

It pulls out details like location, date, and time.

So basically I can just type, or in many cases speak,

the event right into the title,

and it's gonna get all the information and put it in the right place,

which is really, really nice.

I also keep Fantastical's widget on the front page of my home screen,

so I can just tap in there and tap the Add Event button,

and that's a tip

that works for pretty much any calendar app

that does have widgets.

Our next tip is a pretty big one here,

and it's to use recurring events.

This is another area where, like I said earlier,

digital calendars have a huge advantage over physical calendars.

If you have events that repeat, like something that happens every single day,

or every week, or heck, the third Wednesday of every other month,

in a digital calendar app, you can go and set up a recurring event,

so all you have to do is put in the event's details once,

specify how it repeats and if it ends,

and that's always gonna be on your calendar at the right time.

So those are a couple of tips for getting events into your calendar more

quickly,

but what about making those events more useful to you?

Well, one thing that I love to do is add relevant information about an

event into the description field of

that event.

I do this all the time, because when I'm going to an event,

when it's about to start,

my calendar is the most relevant piece of my productivity system with respect to

that event.

I don't wanna be digging through my email.

I don't wanna be digging through my note-taking system.

If there's information about an event,

I'm just gonna open up my calendar and find it there.

Another useful tip is to add optional events to your calendar.

Your set-in-stone schedule isn't the only thing

that can be on your calendar.

You can also basically give yourself options.

So as an example,

I'm currently taking a course to get my professional barbell coach certification.

And the course comes with optional coaching calls

that I can get on every week with higher level coaches who answer questions

and go through different topics.

And I'm really busy.

I've got these videos to make.

I've got Notion templates to make.

I can't always make these calls,

but I always put them on my calendar in a special life bucket called

EDU Opportunities so that

when the time comes,

if I do happen to have time,

I can choose whether or not to attend.

And another tip that's kind of along the same lines here,

create reference calendars for useful information and useful schedules.

So back in college, my professors, like most professors, had office hours.

So at the beginning of the semester,

I would get all the office hours for my professors,

and I would put them in my own calendar called Professor Office Hours.

And normally this was hidden by default.

I didn't wanna gunk up my own schedule,

but in the case that I needed to see a professor,

I could easily just turn the calendar on and see when their free time,

when their office hours coincided with me having some time on my schedule.

And this is also very useful for things like basketball court schedules,

open gym schedules.

Anything that you wanna reference and cross-reference with your own schedule,

make a reference calendar for it.

And finally, this is a tip

that I shared over on my Twitter the other day,

and it's more of a general personal development tip,

but if you find yourself with your longterm goals at odds with your short

term desires,

if you find yourself skipping workouts, or not cooking when you're supposed to,

start scheduling things.

Start scheduling time to work on your goals, whether it's instrument practice, or workouts,

or cooking dinner, because when you schedule something, you remove ambiguity from the choice.

And a lot of times

when we are trying to do things

that we know are good for us,

we are dealing with a lot of ambiguity,

and that contributes to the resistance

and the likelihood that we're just gonna go play video games.

So when you schedule it, when you put it in a calendar,

you're basically saying, "I wanna be beholden to my past self,

and I'm adding some specificity to this goal,"

and it's gonna make it much easier to actually do it,

and it should boost your motivation a bit.

And now we move on to rule number three,

get information from your calendar and get it at the right time.

And I've got two big tips

that you're gonna wanna follow

so that you actually get stuff from your calendar.

Number one, check your calendar every day.

This is a very simple tip, but a lot of people skip it.

A lot of people don't look at their calendars,

even if they're adding events to it,

and that doesn't make the calendar very useful.

So right when you wake up in the morning, check your calendar.

Make it part of your morning routine, and in doing so,

you're going to prime your brain,

and you're gonna get a bird's eye view of everything coming up in your

day,

and be much less likely to have something blindside you

and throw off your plans.

Secondly, set up notifications.

If you are using a digital calendar app,

you can set up notifications to remind you before an event happens.

And I highly recommend using these, especially for very important events, like interviews,

and exams, and the destruction of the universe by Zorp the Surveyor. - Hail

Zorp. - Hail Zorp. -

But hang on a second.

When should you set these notifications to hit?

Well, that is gonna kick us into a bit of a discussion on human

psychology.

See, we humans, with our mushy brains and all,

are susceptible to something called the planning fallacy,

which describes how we are very over-optimistic

when we are estimating how long things are going to take.

This is partly because we basically can't distinguish between the best case scenario

and the average case scenario.

So best case, like you hit every single green light.

There's no traffic.

Average case, there's a few red lights.

There's some traffic.

But our brains conflate them when we're making estimations.

There's research on this.

And there's also the segmentation effect.

If I broke down a task, like go to work,

into a bunch of different mini tasks

and had you estimate how long each one would take,

you would be much more accurate than

if I asked you how long is it gonna take to get to work?

That's the segmentation effect, and we are very susceptible to it.

So when setting up our notifications, we should be cognizant of these facts.

We should know that we vastly underestimate how long it's gonna take to get

places,

to do things, to get ready, and we should set up our notifications accordingly.

Now, one way you can do this is go very simple and just say,

"I'm gonna make it an hour before,"

but sometimes it takes more than an hour to get ready.

So what you can also do is use a fudge ratio.

Take your initial estimate of how long it's gonna take to do something,

and add a multiplier to it.

1.5 is a good starting point.

So if your initial estimate for getting ready for work let's just say is

30 minutes,

then add 1.5 X on that,

and let's just set your notification for 45 minutes in advance.

One additional note here is

that most calendar apps will let you set up multiple notifications.

So for especially important or infrequent events,

I would recommend having an additional notification that comes much further out.

And this is especially important for things like birthdays

or anniversaries where you're gonna need some prep time to find a present,

or book a venue, or whatever it is.

So to quickly recap here,

first set up your calendar system in a way that suits you.

It can be digital, it could be analog.

It's all cool.

Just pick something that you're actually going to stick with.

Secondly, add events to your calendar and relevant information to those events.

Use quick capture techniques

and apps like Fantastical to cut down on the amount of time it takes,

and also make your events more useful.

Add reference calendars, optional events,

and schedule time for goals and things that are important to you.

And finally third, get information from your calendar at the right time.

Check your calendar every single day.

Make it part of your morning routine,

and also set up notifications

so that you have ample time to prepare

and actually get to your next event

so you're not freaking out

and stressed all the time.

Now, as I mentioned earlier,

your calendar is just one part of that productivity system.

If you wanna learn how to set up the entire thing and optimize it,

including your task manager, the way you take notes, your file organization system,

you should take my productivity systems class over on Skillshare.

In this class, you're gonna learn how to set up each of these systems,

but more importantly, you're gonna learn some techniques for optimizing the way

that you keep it organized

so it doesn't get messy

and unusable over time,

which happens to a lot of people.

They end up ditching their systems.

Over 100,000 people have already taken this course,

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