If you own and manage multiple calendars, it can get messy quickly.
Perhaps you confirm meetings in your mind rather than in your calendar.
Or flip-flop between the various “tools that do it all” (without ever committing to one.)
And just maybe, it might not be that you have a calendar problem at all — but a delegation problem.
No matter what ails you the most about your scattered scheduling systems and calendar woes, there are plenty of ways you can streamline your process to help you create more time. And wield more control over your daily commitments.
Let’s talk fundamentals first.
Before we get into the nitty-gritty of optimizing your calendar for ultimate productivity (or simply less time spent scheduling!), we need to talk about the three key things that can provide greater control over your day.
Procrastination strikes when we lack an intentional routine.
Without one — we flip flop. We put things off. We pretend we’ll find time later.
“As children, routine gives us a feeling of safety. As adults, it gives us a feeling of purpose.” – Brianna West.
There is no doubt that without some sense of order and predictability in your days, weeks, and months, you’re more likely to feel scattered and incapable of achieving what you want.
But a deliberate routine can build stability and structure into your daily life. Providing that essential purpose and helping you follow through with your intentions.
Whether digital or analog, having a system for keeping your most important tasks top of mind is productivity 101.
You don’t have to look too hard for task-management apps (like Asana, Basecamp, or Todoist). And there are multiple books to help you perfect your process, like:
That said, to-do items are meaningless if you never schedule the time to do the work.
This is why — along with an efficacious task management system — you need…
While I don't advocate scheduling yourself down to the last minute (flexibility and appropriate boundaries are often more effective) — putting the things on your calendar that either:
Will remind yourself to do them and reserve the space to take action.
The added benefit is that once you schedule something, you can forget about it until the time comes to do it. Whereas if you leave it to float around in your mind — flicking back into your thoughts at the least convenient times — you’ll feel like you’re constantly on the hook.
“If it’s not on your calendar, it doesn’t exist” —Ramit Sethi.
Scheduling things makes life (and execution) easier. It’s that simple.
In his famous essay, Maker’s Schedule, Manager’s Schedule, Paul Graham highlights a fundamental difference in the work days of different kinds of operators:
There are two types of schedule, which I'll call the manager's schedule and the maker's schedule.
The manager's schedule is for bosses. It's embodied in the traditional appointment book, with each day cut into one-hour intervals. You can block off several hours for a single task if you need to, but by default, you change what you're doing every hour.
As a manager, scheduling can be as simple as finding an open time slot, booking someone in, and the work is done.
But as Paul notes:
There's another way of using time that's common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can't write or program well in units of an hour. That's barely enough time to get started.
When you're operating on the maker's schedule, meetings are a disaster. A single meeting can blow a whole afternoon by breaking it into two pieces each too small to do anything hard in. Plus you have to remember to go to the meeting.
As a maker, scheduling a meeting requires significantly more forethought. And as you can imagine, interrupting critical focus time isn’t ideal when you’re knee-deep in solving a new problem.
In other words — meetings cost some people more than others.
But simply being aware of these two different work modes (even if you play both roles!) will make it easier to structure your day and week around how you like to work. And what responsibilities you have.
“When” is arguably the most significant productivity and planning question you can ask yourself.
And with an optimized process for filling and maintaining your calendar, you can streamline the way you organize yourself and your most important tasks and meetings.
But when talking about optimization, it’s good to get clear on what you’re hoping to improve (so that whatever solution you create — has a meaningful impact.)
Consider these three questions to help you figure out where to focus:
More time? More connection? More focus?
Stripping your calendar of meetings isn’t the best approach if you’re optimizing for connection and reaching new people. On the other hand, if you’re lacking significant focus time, you may want to dial those types of high-touch appointments right back.
Get clear on your intentions behind “why” you want to optimize your schedule, and then let that clarity light the path forward.
Automation is an incredible way to optimize for more time. Mainly because there will always be tasks that you can let tech handle.
But often, it's hard to figure out what to automate first.
So here are a few things to ask yourself when thinking about what you could be automating:
Often a significant bottleneck to gaining control of your schedule (and handling the admin required to maintain it) — is that you’re not paying for the features you need.
If you have tools doing some of the work for you — but you have so far put off investing in the paid version — this is your permission to go ahead and spend that extra $15 a month to make your life easier.
Okay, now we’re getting to the juicy stuff — the tactics and techniques you can employ that will change how you work and optimize how you schedule your time.
You’ll notice we’ve divided this list into two different categories:
Getting in the habit of using your calendar to help you follow through is incredibly effective.
You’re likely already conditioned to check your phone reasonably consistently. So adding in prompts to execute the important stuff is a no-brainer.
As the saying goes: what get’s scheduled, get’s done!
Time blocking won’t make you magically more productive. But it will help to create intentional space for your priorities.
And if you require more flexibility — rather than trying a blanket approach (i.e. adding in recurring slots that apply indefinitely) you can make time-blocking a consistent practice at the beginning of your week.
So you can determine what will have the most impact for the next seven days.
A good VA is someone who manages up. They let you know what’s on for the week and remind you of those important meetings and critical to-do’s.
Whenever you enter tasks or meetings into your calendar, ensure you set reminders. And that any necessary resources are attached and ready to go for when you need them.
A good question to ask yourself if you’re struggling to maintain a doable schedule or to keep on top of everything is:
Do you have a calendar problem or a delegation problem?
If you have more money than time, consider a virtual assistant to free up your time. Even saving 10 hours a month can be a game-changer.
A tiny (but notable) refinement is to add in a little extra info when you add something to your calendar.
If you have a meeting or call with someone — make a note of what it’s about or why it’s happening. This can help you differentiate between the various types of meetings and tasks that might pop up.
It could be as simple as adding “Virtual Coffee Date with Carl” to signify a more relaxed and stress-free meeting style. Rather than seeing yet another “Zoom call” on your agenda.
If you’re someone on “the maker's schedule” (or simply dislike meetings), set some boundaries around when and how often you have them.
This can look like:
Taking control of your schedule and making it easier to manage your calendar is more about making it clear for yourself (and others) when the right time to do certain things is.
Connecting your calendars is another simple tweak, but it can significantly affect how you run your week.
Everyone has an overlap between their personal and professional lives. And given that so many of us work from home — it’s impossible to avoid some schedule clashes.
But you can ease those issues if you make sure that ALL your calendars talk to each other.
Setting the expectation isn’t just good practice for clients and customers; you must also make it a habit for yourself!
Don’t wait until the day to decide what to do, or remind yourself of your commitments.
In as little as ten minutes, you can do a quick check at the start and end of your week to review what’s on, where you expect to be, and give yourself the appropriate time to prepare for what’s to come.
Taking the last point one step further, add a check of your calendar and what’s on for the next day to your end-of-day wind-down routine.
All the apps in the world can’t compare to simply reviewing the day ahead the night before and making a mental (or physical) plan.
If you have multiple brands or clients to engage with — theming your days to focus only on one of them can help reduce context-switching and allow you to focus.
Even if you only theme the first two hours of your day, you know you’re only working on one thing for that period. It can make a big difference in how much progress you make.
As an Aussie who works mainly with US clients, the bane of my existence is dueling with timezones. I can’t tell you how many times this conversation has happened:
“Wanna catch up at 10 am Thursday?”
“Sure thing…Wait, do you mean my Thursday or your Thursday?"
But, you can alleviate some of these timezone headaches by adding a secondary timezone to your Google calendar.
You’ll see both timezones displayed on the side of your Calendar view now:
If you get into the habit of popping everything important in your calendar, then it’s a good idea to set a default reminder time (and type) for when you add something new.
You can always individualize this function if you need to, but not having to fiddle with it every time can be handy.
I hate email notifications, so I keep mine in-app. And my default is set to 15 minutes prior. If it’s something that I need to prepare for, I’ll often add a “day before” reminder, too (but do so manually).
Super simple, but such a time saver.
Type cal.new in your Google Chrome browser, and voila! Up pops the new event screen.
Unrelated to your calendar (but just as helpful) are the doc.new and sheet.new equivalents for creating new documents and spreadsheets. Type them into the browser search bar, and you’re ready to roll.
Color coding your calendars can create excellent clarity (at a glance) when viewing your schedule.
If you’re a parent and have a lot of events or tasks associated with your kids, you can create a new calendar for your child, color code it, then add all their events under that calendar.
Alternatively, if you have more than one brand or business but only one email address — you can use the “create new calendar” to easily maneuver between the two.
You’ll notice the new calendar shows up under the “My Calendars” section when you’re viewing it in your browser.
We talked earlier about how helpful setting expectations upfront for yourself is. Well, this little trick comes in handy if you need a short email reminder of everything you’ve got on for the day.
Unfortunately, there are no controls for when this email gets sent. But you will receive your daily agenda in your Gmail inbox at 5 am (according to your set time zone).
Let’s start simple with syncing to your native calendar app (this is for Apple peeps!)
I don’t open Google Calendar much, and I don’t like their app. So I use my Apple calendar exclusively.
You can sync your Google Calendar with your Apple Calendar easily.
You can also do the same for Outlook. Here’s how to sync your Outlook calendar with your iOS device here.
If you’re sick of shifting between your accounts and logging in, you can use Shift to connect them all (plus your favorite web apps and tools).
Then you can customize your workstation to suit your purposes.
The best thing is the no-fuss toggling between accounts from one screen.
Another option for reducing tabs in your browser and eliminating the need to shift between multiple apps to organize your schedule and daily demands.
With Biscuit, you can add your favorite apps. And you won't need to spend time looking for them within your mountain of tabs.
I like that you can see a clear separation between your work and life.
You can route multiple calendars to your Airtable account and work from there to give a complete view of your commitments and tasks.
A great feature is that you can sync multiple calendars, including team calendars.
This tool can help you make better decisions and focus on your priorities rather than simply reacting to your schedule.
You can pull in tasks and commitments from other apps and set reasonable goals for what you want to accomplish each day. Jobs you don't get to today automatically roll over to tomorrow.
It can act as your single source of truth if you’re after an alternative to using your calendar for schedule management.
Many people struggle to figure out what to do every day. And that takes up valuable time and energy.
With Motion, you can use artificial intelligence to take scheduling off your to-do list.
You can combine all of your calendars — work and personal — into one view. Add in your tasks as you need to. And then let the algorithm prioritize everything for you.
We mentioned time blocking earlier, and Reclaim makes this more accessible than ever.
It’s another tool that uses innovative technology to take the effort out of slotting things into your calendar.
But of course, there is still the actual task of scheduling important meetings into your calendar. This is where many people despise wasting time. And hate the back and forth required to confirm a time that suits everyone involved.
This is where SavvyCal comes in.
Let’s take a look at what it can do for you.
Let’s just get this out of the way first: having a scheduling link doesn’t make you an egomaniac (despite what this angry Twitter man might think.)
In almost every scenario, sending a calendar link is preferable to some inane email back and forth, struggling with time zones, scheduling conflicts, and enforcing preferences and boundaries.
It saves time, reduces friction, and simplifies scheduling.
Of course, many scheduling apps have failed to take into account the commitments of everyone in attendance, which has made it feel like more of a one-sided interaction.
SavvyCal fights that by integrating your calendar AND your guests. Allowing recipients to overlay their calendar on top of yours to find mutual availability easily.
If you have a team, scheduling a meeting with a suitable time for everyone involved can be incredibly difficult.
But with SavvyCal, you have two options to combat this:
Plus, with the meeting polls feature, you can invite people to vote on a set of times to meet and book the one that works best.
Whether you're organizing a meeting for work, your personal life, or your side projects, you can check for conflicts across your calendars and set which calendar you want to store each meeting in.
With SavvyCal, you can create naming conventions that find scheduling availability based on the calendar events you make.
You can also create different links for different meeting purposes. This allows you to quickly customize your availability depending on the event's purpose.
We discussed how being more intentional with your time can lead to greater focus and purpose.
And one of the best ways to reduce meetings and interruptions (and the context switching they illicit) is to set limits for how many sessions can be booked per day, week, or month.
SavvyCal makes sure you can always reserve time for deep work.
While you can’t control someone else's availability and preferences — you can make yours well known!
With SavvyCal’s ranked availability windows, you can take back control of your schedule by encouraging recipients to pick the optimal time (while remaining flexible).
You can also generate a snippet of text to propose times in just seconds. Recipients can pick a time to meet in just two clicks.
If you’re overwhelmed by all the options we’ve mentioned above, don’t be!
Because optimizing your calendar isn’t something you can do in a day.
It’s a process that will take time to implement.
You don’t need to rush it, but you do need to do something if you want to feel more organized and save some time.
Then, when you have some capacity to test out some more robust tech tools (and are willing to invest in the cost of these potential time-savers), you can work on building these systems into your current workflow.