Industry Analyst & Strategist

The Best Calendar and Scheduler Combo

This was inspired by two recent items. The first was a request for email and calendaring options at Post Status, and the second was an upsell email at Calendly. My needs are probably not very uncommon, especially for freelancers, independent consultants, and solopreneurs.

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Google Workspace

First and foremost is my choice of “office” platform. I’ve gone from building out and maintain my own email and calendar services way back in the day, to utilizing all sorts of third party services. Without a doubt, Google Workspace (formerly G Suite), is the easiest, most compatible, most scalable, and most cost effective solution. I’m paying $6/month with the Business Starter package. This is a no brainer. What’s also great is that almost everyone I work with is also utilizing Google Workspace. This is actually important for the whole scheduling workflow.


How people schedule online has become more and important especially with being able to quickly get a Zoom or Google Meet going. There are a ton of solutions out there available, I used to use Copper CRMs built in scheduler but it was limited in a number of ways, the biggest being not connecting with Zoom (my preferred video chat service). After evaluating a few I decided that Calendly has first, the cleanest interface for end users to schedule an event, and secondly the most options to integrate with calendars, Zoom, Zapier, etc. I opted for the Premium package at ($10/month billed monthly). Tangent, it’s amazing how cheap Google Workspace is when you compare number of features provided, end tangent. I went with Premium for the following reasons:

  1. Multiple event types (I need 30 and 60 minute types)
  2. Remove branding
  3. Zapier integration

At Premium, Calendly does allow adding two (2) calendars, and the upsell I received was about moving to Pro for six (6) calendars. This is important if you’re trying to show complete availability if connect to multiple Google Workspaces.

Here’s my, maybe more edge case, situation. I am connected to an absolute minimum of five (5) Google Workspace accounts for email and calendar. That number has occasionally even been doubled! So trying to schedule across all of these can be insane. Yes I could connect them all to Calendly but that doesn’t necessarily show that I’m booked for everyone.


I need one calendar that magically has everything that I need to be aware of, and conversely block out all other calendars in a seamless way. I mentioned SyncThemCalendars in The 2020 Setup, but only briefly. This deserves a lot more attention. Here is the basic situation:

  1. Main Calendar
  2. Blue, Red, Yellow, Green Calendars

The Main Calendar is at, yes you can share calendars via Google but, the big but, is then everyone knows where your calendars are coming from, and it may not be appropriate for Blue calendar people to know about the Red calendar. This starts getting messy with calendar client software. What I want is an event in Blue, Red, etc calendars to be fully copied to the Main Calendar. I want original Main Calendar events to create Blue and Red events which have no content except for saying “Busy.” I want Blue events to create “Busy” Red events.

With SyncThemCalendars I have a sync from Main to each other calendar, so Main->Blue, Main->Red, etc. have these settings:

ColorKeep Target Default
Create “Busy” Events

This way, any item created in Main creates “Busy” events with no private information exposed, no Zoom links, attendees, etc.

Now if I create an event in Blue, I want to make sure that Main has everything. The ultimate goal is a single source of calendar truth. so Blue->Main, Red->Main, etc. have the following settings:

ColorKeep Target Default
Create Duplicates in Main Calendar

The beauty of this is that SyncThemCalendars knows not to create a recursive nightmare. This will not automatically send Main back to Blue or Red. To block Red from Blue events we need to repeat the first process, Create “Busy” Events, but instead of Main->Blue, you would set up Blue->Red and Red->Blue. You may not have to go through all of those combinations if everyone in Blue and Red utilize your Calendly, but more than likely you will need create syncs from a calendar to all other calendars. SyncThemCalendars is $5/month.

So total cost is $12/month (calculated on a month basis, annual plans are available for Calendly and SyncThemCalendars).


I would be remiss in not mentioning the best way to view all these calendars with duplicate events. Fantastical by Flexibits is unfortunately Mac world only (MacOS, iOS, iPadOS) but it has a couple of key features depending on how you use multiple calendars, Calendar Sets and Combine Identical Events.

If you are doing straight up duplication across your calendars then Combine Identical Events cleans up the visual madness easily. It will show one event, and you can see which calendars it is on. I have this enabled and it cleans some of the clutter but I really prefer are Calendar Sets. Here I can have shortcuts for things like Home, Work, Clients, etc. Since everything is properly synced to my Main Calendar, I only use my set which displays Main Calendar and Home.

Happy scheduling!

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