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Calendars are Organized! Organized Chaos…

By: Kate Pojeta | Feb, 17 2023

My online calendars are my daily guide. Their ability to sync and be accurate is vital not just to my busy household of six, but also to my ability to effectively manage multiple clients, travel around the country for events, and easily schedule meetings at appropriate times. I need these calendars to sync to a variety of places for a variety of reasons, without having to enter things in 10 different places. If you have multiple calendars and/or email accounts - even just between a work email/calendar and a personal email/calendar, and depending on your age, you may relate to one or more of the following statements:

I remember calendar syncing being an issue 20 years ago on my Treo phone. 
I remember calendar syncing issues with the first iPhone. 
I remember calendar syncing 20 days ago.

Technology has certainly improved - both hardware and software, over the past 20+ years, but the challenge of using calendars in digital formats has still remained a hurdle for many people. Everyone will have unique sync issues, so there is NOT a one-size-fits-all solution here but I do want to introduce you to some calendar tricks and tips that might help you bring your chaotic calendars to a bit of a zen-like feeling (at least until someone does a software update that breaks everything... then you start over...).


I'm a Mac user, so by default, my first recommendation is that you use Apple's Calendar app. You can add Google calendars, Microsoft/Outlook calendars, Yahoo, Hotmail, iCloud, etc etc etc. All the calendars will blend with each other for visual ease, but can be identified by different colors and toggled on/off easily. It's my understanding though that there is a current sync issue happening between Microsoft calendars and Apple's calendar on some devices after a recent update. In this case, you may frantically be looking for an alternative and I recommend Fantastical. This company has been around since the EARLY days of smartphones and calendar syncing and has stayed on top of trends and needs over the years. Mac/iOS only. For the rest of you - you'll get similar capabilities from Outlook or Google Calendar, I just have found them more clunky, particularly on a Mac.


I hear ya. I don't have time for multiple emails to figure out a quick meeting we need to have. If everyone in the meeting is working from the same company, sure, that's easy to find a common time (still good luck, but you can do it!)... when working with those outside your organization, it gets a little more bumpy. And sometimes just picking up the phone and randomly hoping the other person can answer/talk doesn't work and I can't catch you or you can't catch me. A scheduled call has better success rates for me so I direct everyone that needs to chat to my calendar. Then no one misses the meeting and we're all prepared. I do this through Calendly. This is a paid service and worth every penny. I pay for a professional plan at $144/year and the amount of time this saves me is worth way more than $144! There are a variety of plans but I have a LOT of calendars to sync, and given that mostly I'm working and meeting with people EXTERNAL to Event Garde, I can't even just share my "free/busy" calendar and expect it to be accurate. AND, I have multiple calendars for multiple clients and reasons and need them all to sync together AND I want multiple calendars to impact whether I'm free/busy, not just ONE work/client calendar. Calendly lets me add multiple calendar accounts and choose which calendars block time and which ones do not. Then when someone books a meeting with me using a super-simple interface, it auto-adds the meeting/event to my main work calendar and their calendar - AND if they choose "Zoom" as the meeting option, it will auto-create the Zoom meeting and share the Zoom link in the meeting invite. I can even opt to have reminders sent to meeting participants via email or cell phone prior to the meeting to make sure they don't forget about it. Hang on, I need to find my STAPLES "easy" button...


This one has multiple solutions for sure. I'm going to provide a few options based on my experience - and success - but there are many avenues to go down for this. The one that seems easiest is to use Zapier. Using this automation service, you can setup a "zap" that will take certain events from one calendar and add them to another. Maybe you even filter so only events with a particular "tag" or note get added to another calendar. Connecting those accounts in Zapier will let it duplicate information from one calendar onto another.

In one instance, our team has a "team calendar" we share but just like everyone else, the whole team doesn't need the WHOLE of everyone's calendars. Too much. We want to know the big things - when someone is traveling, or at an event, or out of office, or anything else significant that might impact us getting in touch with each other. So instead of sharing all of our internal and external calendars, we actually drop these high level things into a Smartsheet with just a simple start date, end date and the event title (ex: 1/1/23 - 1/2/23, Kate -- OOO for New Year's). This sheet pushes that information into a calendar feed (ICS feed/file) and now we can all sync it to our own calendars. I can view it easily in the context of my day or turn it off when there's too much to look at. All events are "all day" so it doesn't clutter our systems. Or someone can view it directly in Smartsheet. We also have it set to push events coming up that week and then each day to our team Slack channel.

Whether you are trying to wrangle just your own calendars or looking to make it easier for others to book on your calendar, there are many options in the way of software, processes and automations. Finding what works for you may take a little time and effort. While I cannot promise your tech support company can resolve it all for you, I would start there. Sometimes they can't make the non-work ones interface with the work ones though due to their own limitations/liabilities. If you approach it with a complete list of calendars and either the issues you're having with each or how you want them each to react, that's the best way to move in the right direction. Be patient, know it will take some trial and error. And if you really get stuck, you might be able to find time on my schedule to chat... https://calendly.com/katepojeta 


Photo Credit: Pexels.com

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