In September 2021, I became a Happiness Engineer Lead at Automattic for WordPress.com after spending a little over 5 years as a Happiness Engineer. Throughout my progression from HE to HE Lead, I had so many fellow leads guiding me and also consulted many resources.
Still, Reboot training is offered to all new or aspiring leads at Automattic, and it was highly recommended to me. With my sabbatical last year, I delayed attending this training for a bit, then life got in the way for a while. Finally, in March it was time for me to visit NYC for this highly anticipated training. It was a quick Mon-Fri trip, but I managed to learn a whole lot and enjoy a bit of the city as well.


Immediately after checking into the hotel, I ran down the street for pizza. About 2 mins later, that pizza (pictured below) burned the roof of my mouth. It was definitely a personal record, the fastest I’d burned my mouth on pizza after arriving in NYC.

That evening I joined some of the other attendees for dinner at Essex where I had amaaaazing Brussels Sprouts (seriously I still think about them).


In the morning, I stopped by Kona Coffee Roasters for breakfast on my way to our office on Crosby St. We spent all day in training and learned a lot about communication and coaching.
In the evening, we had dinner at Souvlaki GR, a Greek restaurant. I don’t think I’ve had authentic Greek food before, this place did NOT disappoint. I had the veggie moussakas and also some of the halloumi – both were so tasty. After dinner I stopped by El Churro which was dangerously located at the corner of the block our hotel was on.

On Wednesday, I started the day with breakfast from Bagel Boss – a very plain bagel with cream cheese, just how I like it. I took the bagel (and a latte) to go and enjoyed them at the office. We covered concepts such as delegation and performance management during our all-day training.
After training, we enjoyed dinner at La Caverna, a Mexican restaurant decorated as a cave. This place actually reminded me of the cave my team had dinner at in Mexico a few years back – Alux, which was recently featured on Vanderpump Rules! The food wasn’t what I consider to be authentic but it was delicious and they made me an awesome passionfruit mocktail. I took no food pictures today, but did snap a few photos during my walks.



On our last day of the training, I started out by grabbing breakfast at The Bean – 2nd Ave where I once again had a plain bagel with cream cheese and a vanilla soy latte. The latte was piping hot, so hot that I kept having to shift hands as I walked to the office that morning, it was still plenty hot for me to enjoy once there. We wrapped up the training discussing transitions which I found to be super helpful and timely.
For dinner, we ate family-style at Sauce. Everything was delicious, especially the Sangria, and there were tons of vegetarian items for me.

The meals we shared together were so valuable, I had so many great conversations with leads from all over the company and made connections with several people who inspire me!
Throughout the week, I managed to snap a few photos from our awesome NOHO office.






Before I headed to the airport on my travel home day, I stopped to have breakfast with a close coworker (and fellow lead), Kathleen! We ate at a vegetarian restaurant in Nolita – The Butcher’s Daughter. Their Walnut cacao latte was super tasty as was the food! 😋

Then I headed home, with one important item: A small gift for Willa!

I always bring back Willa a little item from wherever I travel, something I know that she’ll get a lot of use out of and something that really fits the place that I was visiting. I purchased this from Little Moony, a small business with a lovely story.
Since attending the Reboot training, I’ve implemented some changes and utilized some of the concepts, the training was effective and I reflect on my workbook notes all the time. Our facilitators, Carl and Virginia, were rockstars!
I look forward to visiting NYC again soon, hopefully as a family trip next time. Until then, I’ve got work trips to Athens, Greece and Pittsburgh coming up soon!