My parents, my sister, and I met in Portugal for a few days. We hadn’t done a trip with just the four of us in fifteen years. It was a wonderful time for us to spend together without the trip being all about the kids. We also all met up in Kenya in March with our spouses and kids. Spending time with family was the best part of the leave.
I started parental leave with three goals: time with family, health, and leveling up with AI. I go back to work on Monday and here is how each went.
Time with Family
First was a big, three-week trip to Kenya. The kids were in a different environment picking up Swahili words, eating new food, and experiencing places I love, like Naivasha. Most importantly, we spent a lot of time with our close community – my parents, sister’s family, cousins, extended family and friends.
Then back to Brooklyn – the “boring” version of presence: drop-off, pick-up, doctor’s appointments, walks with Juni, putting the kids to bed every night. This is the part that compounds – the fun around the boring moments is what the kids remember, even over the big trips.
Finally, the trip to Porto with just my parents and sister – long walks, good dinners and unsolicited advice all around. We don’t get long stretches together very often, as they each live a continent away. The blocks of unstructured time we got on this leave were irreplaceable and I don’t think we will have another opportunity to do it again.



Recovering from Injury
Last year I had a string of injuries culminating in a busted shoulder that had been limiting me for six months. No real lifting, no squash, limited yoga. I’m now basically injury-free, which is the biggest win. I started with swimming and yoga, squash once a week, and lifting weights again. Being active again, after the better part of a year of not being able to, feels great both mentally and physically. It came back in small moments – a chaturanga in yoga that held or a forehand volley in squash hit without flinching.
I had stretches of eating well and stretches where the structure dissolved, especially around traveling. Now I need to be more intentional about consumption, and make sure the training routines survive when work ramps back up.
Learning to use AI
I started my parental leave as a user of LLMs to draft documents and help me think. I’ve now become AI native. It’s the default way I now think about getting something done – building, writing, learning, thinking – all of it runs through these tools.
I learned by building things. Shortcut Pack, a tiny utility built in two days that I’ve used for years but now makes it easy for others to set up. Let them Burrow, a learning app for Kal so he can go as deep as he wants on whatever topic he’s currently excited by. Omni, an AI health coach built on OpenClaw that pulls in Whoop, Withings and Apple Health with a coaching loop on top. Making Pact, a Slackbot built by agents that worked while I was off doing something else. Finally, Sir Restaurant, a personal kids book about a goofy routine we all love.
AI-native writing is the piece that translates most directly to work. I now use AI throughout the process: for drafts, for edits, for quick feedback on what’s working and what isn’t. I built a writing system that gives me pointed feedback on my drafts against my own archive.
The product experimentation and the writing system have already changed how I approach problems, and they’ll improve the way I work.
Uninterrupted time
This leave reinforced something I already knew but don’t always live by: the most valuable things in my life need uninterrupted time.
A few weeks is enough time for kids to settle into Kenya, for a shoulder to finally heal, for a new way of working to become default, and for a family spread across three continents to remember what it feels like to just be together.
That was the real gift of the leave.
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