Backdated entry: 4 July 2026
If you work at Automattic for five years, you are granted a 3-month paid sabbatical. I officially became eligible to take my sabbatical on the 5th of July 2026, after working at WooCommerce (owned by Automattic) as a Customer Success Manager for the last five years.
I felt like this amazing perk would be a great opportunity to start writing again. I’ve fallen off the writing wagon for the last few years. I’m not entirely sure why, but nevertheless, let’s see how I go with documenting the next 90 days.
I may write every day. I might just write every other day. I’m not going to put too much pressure on myself, but I do want to try to be as consistent as practically possible. To help me stay consistent, I connected my WordPress site to Claude via the WordPress MCP. I plan to send Claude a voice note about my day and instruct it to keep my tone of voice and my style of writing/thinking/talking as close as possible to the voice note, while still cleaning it up if needed. I’m a big fan of removing friction that would otherwise prevent me from posting at all. So if I sound a little ‘robotic,’ I’ve used AI to publish and clean up my content.
The first day of my sabbatical technically fell on a Saturday. My wife and eldest son were in Johannesburg for a conference and to visit friends and family, so I spent the morning with my youngest, Charlie, at one of his favourite breakfast spots, Spur, hugely popular here in South Africa.
#sabbatical
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