The problem with calendars nowadays

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I find myself stuck to my phone nowadays — it’s a necessary evil that helps me keep on top of my work through a plethora of apps which are no longer a help but rather a necessity. There’s email, Slack, Github, Okta, Google Docs, LinkedIn, WhatsApp, Zoom, SMS and the list goes on. Amongst these, one such app which I find myself relying on daily is the calendaring app: this helps me plan my work day and allows me to get involved in relevant conversations or avoid the ones where I am not needed directly.

The calendar app on my phone is great, because it provides an aggregated view of all my calendar accounts: my work account, my personal one, my son’s school schedule, our family calendar, my Endeavor calendar, and in instances where I get to attend or speak at conferences, the schedule of the conference. At any point if I need to know where I need to be or what I need to do on day X at a certain time, my mobile calendar app tells me, I love it!

But I have also a bone to pick with all these calendaring systems: while I can see the events across all these calendars, anyone else who wants to schedule some time with me does NOT! What do I mean by this? Imagine a scenario where I have to attend a meeting (albeit virtual at the moment) at my son’s school — that will pop up either in my private calendar or in my son’s school calendar, and as such I will see it in my beloved calendar app. At the same time, one of my team members asks for a bit of my time to help with project X; they look in my work calendar and that time slot is empty so they grab it (as truth being told empty slots in my work calendar are getting hard to come by these days). Of course, I promptly jump on Slack and tell them that I cannot make that time — and they look in my work calendar again and find the next empty slot. Guess what though? That date/time they are choosing coincides with an event I am part of! So I go online again and tell them really sorry but I can’t make that time either. In fact, I tell them I have an opening on this date and time, does it work? They go and check in their calendar and tell me that’s a no go… So I go back to my beloved calendar app and tell them that my next availability — and we go through the cycle and frustration again until we find some time.

Doesn’t this sound like the early days of calendaring to you? When we couldn’t see each other’s calendar and we had to go back and forth until we agree on a timeslot? 🙁 Why should this be the case when we have tools nowadays that allows my colleagues to see my work schedule? But here’s the thing: they can see my work schedule but not my other calendars/schedules. And I don’t feel that comfortable sharing my personal calendars with every single person I need to interact with — nor is it scalable (I probably interact on a monthly basis with 100+ people and it’s not always the same folks).

Imagine another scenario if you are a consultant juggling 5-6 clients at the same time: chances are that for security and compliance reasons each one of them will give you an email account in their system and all communications and access to their intranet is probably carried out through that account. The trouble is if client X wants to grab some time with you, they have no idea if client Y, Z or T have already blocked some time with you that day. You can of course start manually blocking time in all your calendars the moment client X sets a meeting with you in their corporate calendar, but that is not scalable: if you are dealing with 5 clients that means you have to block time in 4 other calendars every time you get a meeting request. If you have 3-4 meetings a day this starts getting unmanageable. And if the client then starts also changing date and time you will get confused very quickly as to what and where and when is happening.

For that reason I put together — it allows me to simply surrender all my calendar accounts (currently they happen to all be Google Calendar accounts) and it blocks time across all my calendars the moment someone requests time with me in any of my calendars. This way, if I am at a conference my colleagues see in my work calendar a timeslot blocked — they don’t care what I am doing during that time when they are trying to get hold of me, they just need to know what slots are ACTUALLY available. Similarly, if a request for mentorship comes up in my Endeavor calendar they can tell right away what times I have available or not.

It’s a simple but very effective way of duplicating calendaring data across accounts, which allows me (and people who interact with me) to have a much better understand of when I might be available. If you encounter any of the problems I’ve described above, will probably help you too — try it out, it’s free!