At half past four on Friday I clicked the join link for a call I had asked for. Empty waiting room. I checked the invite again. The meeting had run from four to half past. I had shown up exactly as it ended. Four other people had been on it. I had called it.
First time in the 60 days of building this in public, and I would like it to be the last. The fix is boring and I should have done it the day I signed the client: sync your Outlook calendar to Google Calendar so every meeting, on either side, lands in one view you actually open. I had looked into it once, hit a block from the MSP, and dropped it.
So there I sat at half past four, looking at a finished meeting I had requested, in front of the four people I most wanted to look organised to, and nobody left to apologise to because they had all logged off. If you work across two companies' tools, you have a version of this problem and probably do not know it yet.
I have run my whole life out of Google Calendar for fifteen years, since about the time calendars moved online. My enterprise client runs on Microsoft. Their whole shop sits inside a managed Microsoft 365 tenant, locked down by the IT company that runs it for them. When I came on I got a Microsoft account and an Outlook calendar I almost never open. Even though I purposely purchased a mac mini to set up for their tenant, and to download their company portal software, 7 days later, I'm still having to piece things together through web access only.
Two failures stacked on top of each other. I accepted the invite into that Outlook calendar, the one I do not check. And I had the time wrong in my head, four-thirty instead of four. Either one alone and I might have caught it. Both together and I was always going to miss it.
Working inside a client's managed environment splits your day across two systems that were never built to talk to each other. Half my meetings lived somewhere I never looked. A calendar you do not check is not a calendar. It is a list of things you are about to miss.
The fix, in the order I would try it
If you are in the same spot, here is how to get a locked-down work calendar into the one you live in.
Start with the free, native route. In Outlook on the web you can publish your calendar as an ICS link, then subscribe to that link from Google Calendar under "Other calendars, From URL." Costs nothing, no extra software. Two catches. It is read-only, and Google can take up to twenty-four hours to refresh it, so a meeting someone books this morning might not show on your phone until tomorrow. For a founder who lives by the day, that lag is the whole risk you are trying to kill. The bigger catch: a locked tenant has usually switched publishing off, so this is also the first thing that will not work. This was the case for me, as I had tried to use this sync and it didn't work.
If publishing is blocked, or you just want it live, use a real-time sync tool. OneCal and a few others connect to both calendars through a proper login and copy events across in real time, no publishing, no day-long lag. One thing to know going in: a managed tenant often blocks outside apps from connecting until an admin approves them. That is not a wall, it is one email. Ask the IT company to approve the one specific app for your account. A targeted ask for a single tool is a far easier yes than a fight about tenant policy.
If the admin will not budge on any of it, fall back to the human version. Have every invite for that client sent to your real address, or set the work mailbox to forward invites to it, and accept them into the calendar you actually check. Then turn on alerts that reach your phone, not a browser tab you closed three hours ago: one the day before, one an hour out. Belt and braces.
So I am going the real-time route. One sync, both companies into Google Calendar, on my phone, with an hour's warning. One place. The thing I should have set up the day I started.
The part that is not about calendars
I track most things in this business, and I still let half my meetings live somewhere I never looked, because moving them felt like a twenty-minute chore I kept putting off. The twenty-minute chore cost me a meeting I had called, in front of four people, on the account that matters the most right now. That maths is not close.
If you have reinvented yourself into something that puts you across more than one set of tools, a contractor, a fractional operator, anyone with a foot in two camps, you have this. Two inboxes. Two calendars. Two chat apps. The work is not learning a clever new tool. The work is dragging everything into the one place you already trust, and then trusting only that. One calendar. One inbox. One list. Boring, and it is most of the job.
I meditate every morning and keep a gratitude list, so I would like to tell you I let the embarrassment go by lunch. I did not. I sat in it for a good hour, and I am still sitting with it the next day as I write this. The only apology that counts is building the thing that stops it happening again.
It's a foggy Saturday morning in France. The sync is running before next week starts.
Day 65 of 365.
Monthly Revenues $9,200 | Clients 2 | Prospects (Meta to WhatsApp campaign built, WABA pending) | Team: Me + Jan (CTO)