Why review this year?

As I’m starting to write this post I’m sitting in a coffee shop in my neighborhood. This morning Becca and I had breakfast at the always delightful Orphan Andy’s in the Castro and then spent a little time shopping at Cliff’s Variety. It’s my 32nd birthday and I’ve decided to take the day off from work and just relax, and increasingly I’ve been drawn to journaling and writing posts like this for my website — so that’s what I’m going to do!

I’ve seen a lot of people write “year in review” posts on their blog after the calendar year ends — and I think that’s a decent idea — but I don’t want to wait six whole months to write one when I can just review the 31st year of my life instead. In this post I want to reflect on what big events happened over the past year, what I learned, and what I hope to achieve in my 32nd year of life.

Looking Back

A year ago today Becca took me out to a fabulous new restaurant called Mijoté for my birthday (well, we actually celebrated a few days late but I digress…). Looking back at the menu we had scallops, razor clams, octopus, and duck, along with a host of other courses. The dishes were simple but expertly prepared, showcasing the ingredients — just how I like it! It was a great way to celebrate my birthday and a great start to the year ahead, which at the time I didn’t realize would be so full of changes.

In the weeks that followed my birthday, we celebrated Pride in SF with some friends — my first time doing it as a semi-out trans person. We marched in the parade with a contingent from Becca’s employer and it was fantastic to be surrounded by such positive energy and love. Shortly thereafter, my mom visited San Francisco — her first time being able to visit since I moved to the west coast. It was a fantastic trip full of lots of touristy moments, sightseeing, good food, and a lot of laughter. That trip was also my first time spending time with my mom since coming out to my parents as Gabby. I think it was a little odd for us both to navigate that new dynamic, but it was overall a great experience to finally get to be my true self around family.

The months that followed were marked by a range of fun experiences — from helping one of my best friends adopt two kittens to finally getting to see Wicked live on stage. But it was also a period of reflection and transition. By the fall, I was ready for a new challenge — something that would stretch me in new ways and help me grow. In October of 2024 I took the plunge and left my job for a new role at Handshake, a significantly smaller company than I was used to working at. This was a big step out of my comfort zone as I had grown from an Apprentice all the way up to Senior Engineer in my previous job and I was worried my skills wouldn’t transfer well to a different workplace with a different tech stack and ways of doing things. Thankfully, I was wrong!

Handshake delighted me at first. The culture and people are awesome and made me feel extremely welcomed and supported from day one. Getting to learn a new tech stack (Ruby on Rails + React) was fun and I felt like I was in coding bootcamp all over again, but in a good way. I felt an enthusiasm for my work that I hadn’t gotten to experience in a long time.

The next few months would involve a lot of fun personal excursions. I went to New Orleans for the first time to see Taylor Swift on the Eras tour along with Becca, her best friend Kaitlyn, and my best friend Chris. I also had a fantastic time around the holidays. I got to attend the Leaf Raking Rager (a tradition among my Vermont friend group), celebrate Thanksgiving with my family in Massachusetts, and host a friend for Christmas dinner at home in San Francisco¹. By the time February 2025 rolled around, I was feeling settled into work at Handshake and continuing to enjoy it, but my life was about to change again in two big ways.

First, I made the decision to come out at work. Seeing my old name² on Slack day in and day out was starting to get to me and I was reaching a point in my medical transition where I physically appear more feminine and I wanted to just get to be myself at work. Around the same time I kicked off the process with HR of changing my name on Slack/email/work systems, I got an interesting message from my manager’s manager. He wanted to talk, and I was worried it was something to do with my name change. Instead, it was a job offer: to leave my team and join an internal startup at Handshake working on something totally different — a brand new direction for the company. After consulting a lot of friends about what I could expect and how to think about an offer like this, I took another leap of faith and joined!

Joining this new team as Gabby felt amazing but I didn’t have much time to reflect on it as I was pretty abruptly thrown into the deep end and got to work right away in another new tech stack, building a huge new part of the app in just a week or two. I had never experienced work like this — building from basically a blank slate with all the latest and greatest tools and frameworks and technologies. I was truly unprepared for how different a true startup would feel from LinkedIn or even from the core part of Handshake (which is a fairly established Series F company with many hundreds of employees). I threw myself into the work with a renewed vigor and started to find myself getting really excited about software engineering and pushing myself to learn new skills and topics in my free time.

As I write this post today, I’m still on that internal startup team and we’ve finally gotten to go public with what we’re actually working on. This post is about me so I won’t talk about my work at length except to say that I’m so glad I made this decision and despite the long hours and hard work I’m still having a blast with it.

Perhaps the biggest event of the year, for me, happened in the last few weeks. I came out! Publicly! At long last. I wrote about it at length in my earlier post and I don’t have much to say here except that it went better than I could have possibly imagined. Every single person in my family and social circles that I told reacted with love and support. I recognize that this is not the experience that all trans people have and I consider myself extremely fortunate to have such an amazing family and circle of friends. The road ahead (legal name change, continued medical transition, dealing with horrible nationwide transphobia, etc.) certainly won’t be easy, but it will be much easier knowing I have so many people in my corner.

Key takeaways

That brings us to today, at the coffee shop, where I’ve taken a long weekend break to celebrate my birthday and invest in myself. As I write this post, there are a few big takeaways and lessons learned that spring to mind:

1. Advocating for myself is important, and it works. For so much of my life I’ve been a classic “people pleaser” and wanted to avoid “rocking the boat” by asking too much of other people or doing things that may disrupt them. In large part, I think that’s why I stayed at my previous job for so long: I didn’t want to let anyone down by leaving. This year, however, I’ve learned that sometimes it’s okay to choose what’s best for me and ask for what I want, and that it’s actually better for everyone when I do that. This manifested in many ways, from putting myself out there on the job market to asking people to respect my new name and pronouns and identity. By advocating for my own needs, I’ve been able to show up as a happier and healthier and more complete version of myself.
2. My physical health and fitness is important. I didn’t even mention this above, but by far one of the most significant changes in my life in the past year was finding a genuinely fantastic personal trainer³ and beginning a (mostly) weekly habit of working out together at my local gym. For my entire life I’ve just thought my fitness was kind of a lost cause and that it was never something I could improve, but it turns out that all I needed was some help from an expert to steer me in the right direction. Training has taught me to push myself but also to stand up for my needs — when something hurts or is too much I don’t try to force it, I simply let my trainer know and she course-corrects us.
3. Moving to San Francisco was the right choice. While I’ve lived in the Bay Area since late 2019, moving to SF only happened within the last couple of years. I’ve never gotten to be a “city person” before and in this year it has finally started to click why people love cities so much. Getting to work downtown and take our wonderful public transit to get there and back is a joy. Getting to explore new neighborhoods and find little hole-in-the-wall spots to read, write, and study fits my personality perfectly. While it’s still been a little difficult to make new local friends (it’s hard as an adult anywhere), I’ve had much more luck with it in SF than in my previous California suburb experiences.

Looking ahead

As I’ve written about before, I’m a big proponent of “Yearly Themes” as introduced to me by the Cortex podcast. My theme for the calendar year is “Year of Transition” and that continues to be the overarching theme for the next ~6 months until 2026 rolls around. I don’t know what my 2026 theme will be, but I still want to lay out some loose goals for my 32nd year of life, some of which align with “Year of Transition” and some of which do not.

• Continue to experiment with my gender presentation and invest in ways to feel better as myself
• Read more books and spend less time mindlessly on the web
• Dial in my fitness habits and routine even more and start developing the confidence to work out solo in addition to my personal training sessions
• Spend some time learning and pushing myself intellectually⁴
• Get involved with local political organizing after a long hiatus from being politically active
• Break out of my shell a bit and try to get creative with my new photography hobby

I’m not sure if I’ll actually achieve all of these or even any of them by my 33rd birthday, but these reflect my values and priorities moving into being 32. Looking back, year 31 was probably one of the best years of my life and I hope this momentum can continue into this new year. I finally got to introduce my actual self to the world after years in the closet, I grew professionally in ways I never could have imagined, and I truly started to fall in love with the place where I live. Now that my work situation is more stable and less draining, I feel like I can throw myself into all these other areas of self-improvement and make year 32 a fantastic year full of growth and positive change.