2021: Year In Review

My 1SecondEveryday video - my 9th year doing it

2021 had a lot in store for me β€” a new job, bucket-list travel,Β  and most notably, a new family member!

Last year, I was really excited to end the year with some self-reflection. I had the week between Christmas and New Years off and was excited to slow down, look back, and jump into 2022 with clear eyes to take on the challenges of the new year. I was pretty confident that I'd publish my annual recap before the end of the year.

Seeing as I'm publishing this past the midway point of the year, things didn't exactly go to plan (much of this was written earlier in the year).


And that is because we welcomed our baby boy Miles into the world in late December-- six weeks before we were expecting him.

Laura and I are not known to arrive early for ... anything so it was an uncharacteristic move for a member of this family to get here early. My theory is that he was just as excited about Christmas as I am and didn't want to miss it. Because he was born at 34 weeks, he needed a little more time to bake and had to spend some time in the NICU. The silver lining: Miles got his first-ever visit from Santa in the NICU at just six days old!

After almost four weeks in the NICU (and Laura and I shuttling ourselves back and forth everyday), we finally were able to bring Miles home. Already, I can't imagine life without him. He is literally the best and I'm trying to get as much contact napping as I can get while I'm on paternity leave.

It has also been amazing to see Laura immediately transform into the best mama to Miles πŸ₯Ί. He is so lucky to have her as a mom.


In other major life news, I have a new job! File this in "Things I Didn't Expect in 2021".

But first, a recap of my time at IG.


2021 was actually a great year for me at Instagram. It was the first time in a few years that I felt like I got to work on the creative product work I really enjoy.

At the beginning of 2021, I was put on a team β€” "Stories Studio" β€” whose goal was to explore areas of Instagram Stories that we felt like were overlooked or underinvested in and try out new features. We weren't tethered to any specific feature set and were allowed to go back to first principles.

If I'm honest, I was skeptical that something like this would actually work because I felt like these efforts within Big Cos rarely work. Big Cos tend to focus on "extract" work β€” maintaining what is currently there β€” rather than the explorative work. Despite that, I thought it'll be fun to build some fun stuff with some of the most talented people I've worked with before shutting down a few months later.

And build fun stuff with talented people I did! We explored a ton of ways to look at Instagram Stories differently. We played with temporality as a lens into your friends Stories. We also took a look at some of the core mechanics of navigation β€” like the timer. We also looked at ways to alter your audience and how we could make it easy to map your existing social mental model when you share a story. We built some really cool stuff.

Some of these ideas made it further than others but the process of ideating, creating, and building was some of the most fun I had at Instagram.

One of the ideas that did actually make it out was the "Add Yours" Stories sticker. We wanted to explore how we create a product around the idea of "sharing with" your friends rather than "sharing to" your friends. Much of social media puts you on your own stage and makes you come up with something to say, which can be stressful. "Add Yours" was meant to help make it feel like you were "participating" in something rather than starting from scratch.

We also finally got "Hiding Like counts" launched after 2+ years (albeit a bit watered down from my perspective πŸ˜’). It was a journey to get this out the door β€” but that is a story for another time 😁. It was really satisfying to see it finally out in the world and even more exciting when I see people in my feed use it!

The opportunities in 2021 played to my strengths and stretched me in all the right ways. I felt like I was reaping some of the rewards of some investments in growth I made in 2020.


So with such a great year, why did I jump on the Great Resignation bandwagon?

In short, it felt like an opportunity I couldn't pass up. I wasn't looking to leave at all (in fact, I was already planning my 2022 and 2023 at IG lol) but the more I learned about Patreon and its vision, the more excited I got. It came down to three main reasons: people, mission, and impact.

Patreon had made a few great hires that put Patreon on my radar. First, our IG product lead β€” Julian β€” joined as the Chief Product Officer. I saw that they had hired Utkarsh - a Twitter and Google engineering vet. Finally, I saw that my good friend Rockman sold his company to Patreon. I had to learn more.

I caught up with Rockman and learned that Patreon had an impressive and fast growing business. It had strong financials and was coming off of a fresh round of funding at a $4b valuation to invest heavily in growing a world class team.

Not only had the team been hiring well, it was planning on growing quite a bit more. Working on "Stories Studio" reminded me how important it is (and fun!) to me to work with amazing people. I was really excited about the prospect of working with the folks already on the team and also building out a world class team (hashtag mission accomplished).

In addition to the people, I was captivated by the mission of the company. The internet has always had the promise of letting creatives connect with their 1000 true fans β€” no matter where they are in the world. Working on Patreon feels like helping the internet live up to that promise. Today, Patreon is mostly a membership/subscription product, but that is just a sliver of what we could build for a growing creator economy. Hearing the long term vision of what we could be building from Jack had my brain lighting up.

Lastly, I felt like it was a place I could really have an impact. My experience doing startups at Timehop and working on large products at Instagram felt perfect for a company that is in transition between the two. It was exciting to have the resources of a bigger company without the trappings of the bureaucracy of a Big Co.


In between all of the life changes and year 2 of the pandemic, we got to do some travel!

We started this year's travel much like 2020 β€” picking destinations we could drive to and with mostly outdoor activities. Vaccines had just started rolling out (remember how stressful it was to book an appointment??) so we wanted to keep safe and keep risks low.

Cherry Springs

Our first trip was to Cherry Springs in Pennsylvania β€” the closest dark-sky preserve to NYC. It had been on Laura's list for a while so we figured it was as good a time as any to go since we weren't ready yet to fly. As native New Yorkers, we rarely get to see a sky full of stars so we were pumped to go see it.

There's nothing like a sky blanketed with stars to make you feel tiny in the vastness of the cosmos in the best kind of way.

The trip gave me an opportunity to nerd out about my photo setup for astrophotography. I'd never done any astrophotography before and it gave me an excuse to borrow a bunch of gear from BorrowLenses I'd been meaning to try out. In the end, I rented a 16mm f1.2 from Borrow Lenses to get a wide and bright lens.

Martha's Vineyard & Cape Cod

In June, we took a trip to Cape Cod to get some beach time and β€” for me β€” hunt for every basket of fried shrimp I can get my hands on.

We kicked off the trip staying in an Airstream at the newly opened Autocamp Cape Cod. It was a fun experience and was a vibe, but maybe a one-time experience.

We then headed out to Martha's Vineyard for a few days.. We drove our car over the ferry and thoseΒ  days were filled with a lot of beach time and poolside breakfasts. We ended our trip with a few more days on the Cape, leisurely driving up the National Seashore and stopping anywhere that caught our eye.

It was also during this trip where we booked our first flight in over two years. Vaccination rates were up and positivity rates were down, and that gave us the confidence to rebook a trip to Switzerland we were supposed to do in 2020! (We had not foreseen the Delta wave creeping around the corner)

Switzerland & Lake Como

We closed out the summer by spending two and a half weeks hiking through the Swiss Alps and then enjoying some sun and lake time on Lake Como.

We were supposed to go to Switzerland in the summer of 2020. Obviously, we weren't able to go because ... well, pandemic. So, during that mirage of a time period after much of the vaccine rollout and before Delta came, we booked our trip! Luckily, we had planned a bunch of our Switzerland leg so we were able to pick up where we left off.

We started the trip off in Zermatt to visit the area around the mighty Matterhorn. The highlight here was finding these sheep hiking buddies!

After that, we headed to the Jungfrau region of the Swiss Alps. I'd been wanting to go to the Jungfrau region for years after seeing some friends' trips and countless Instagram photos of the Lauterbrunnen Valley. The photos always seemed like they were straight out of a fairy tale. There was no way this place was real.

Even with my high expectations, the Jungfrau region exceeded those expectations. The density of jaw dropping views and stunning hikes was unreal, especially for a country that is less than β…“ of the size of New York State.

Even more impressive than the views, though, was that Laura was in her second trimester when we went on these adventures!

After nearly two weeks in the mountains, we headed down to Lake Como. We met up with our friends Vic and Jay, who were coming from London. Much wine and spritzes were had, gelatos consumed, and lakes boated!

Revisiting Goals and Habits

I didn't hit any of my goals I set last year except for the most important one πŸ˜„. I won't even try to revisit my habits here πŸ˜…

I'm a bit bummed I didn't make more progress on my goals or habits, but I'm not kicking myself over it. There were a lot of stresses throughout 2021 both on a personal front and at work. Our baby journey was tough, pre-vaccine NYC winter was cold and bleak. Work had many bouts of intense periods; I was, at times, the only engineer working on all of our teams projects both on iOS and backend.

All that to say β€” life happens and worse things have happened than missing some goals. A lot of other good stuff happened.


I was above pace to hitting my 2,500 mile goal through summer. Once we went to Switzerland/Italy, it really fell off the deep end and I never got my groove back.

I'd like to blame it on starting a new job and being busy at work but I think the real reason was that I sort of just got burnt out on it. My motivation was waning a bit before my Switzerland / Italy trip (though I did do one of my bucket list rides in Italy!) and really just fell off hard after the trip. It seems like burning out on the bike is a theme.

Takeaway: I find that my cycling can sometimes start feeling more like a chore than enjoyment. I try to power through β€” rather than taking a short break β€” and end up falling completely off the wagon.


I was never able to work my book reading habit into my daily routine. I filled my reading time between all of the newsletters I read and all of the articles that come out of it. And if I'm honest, it is so much easier just to doomscroll on Reddit or Twitter when I'm exhausted instead of sitting with a book.

More broadly, I actually felt a little squeezed for time even to read the newsletters for my weekly update. There were periods of work where I was working 12 hour days and that left little time and scant energy to really dive into something deep.

Takeaway: I've actually got to carve out time. It hasn't been the natural thing I reach for to fill time. If I don't, I can easily fill my time with all of the articles/blog posts I have in my Matter queue.


We started looking for a place to buy in the burbs but ended up feeling like the market was too crazy (it was and still is) and that we were in a position where we didn't feel the immediate urgency to move. I don't think we wanted to move badly enough to overbid by 20-50% over asking.

Takeaway: I don't feel too bad about this one. We'll see how the market changes this year and the next.


This one we checked off πŸ˜πŸŽ‰

Which is not to say it was easy. It was a multi-year journey with many visits to the fertility clinics, lots of shots, and Laura's display of resilience was awe inspiring. There were some pretty challenging times but seeing our baby boy makes it all worth it!

Looking Forward

I'm keeping this section pretty focused and scale back the number of things I want to commit to this year. These are the things I want to nail and doing fewer things should yield better results.

πŸ‘¨β€πŸ‘©β€πŸ‘¦ Being a Father

I'm in "unknown unknown" territory of being a dad and want to try to be the best that I can be. I've got a lot to learn and want to make sure I've got the time and space to do that.

πŸ€“ Work

I'm really excited about my new role at Patreon and want to make the most out of the opportunity ahead. There is so much to build and so much I feel I can bring from Instagram and Timehop to help the mobile at Patreon really shine. It'll be a fun ride to deliver a great product to our users.

The role also has challenges that I'm excited to jump into. It is in an industry that I don't have as deep an intuition as I did at Instagram. There is a lot to learn!


No hard goal here. I honestly have no idea what a reasonable goal is now that we have a newborn. I'm currently getting up a bunch of times overnight to feed Miles and can't imagine having the energy to exert beyond walking to the corner store. Still, this period of extreme sleep deprivation shouldn't last forever and I can hopefully start working in something more regular.

I reread my post from last year and I could really feel the apprehension in between the optimism I had for 2021. The year started off on the apprehension and anxiety side of things, but turned out to be a year of amazing life changes.

2022 should have a lot of new challenges in store with a new baby and a new job β€” but ones that I feel privileged and excited to take on. I'll be excited for this post next year 😁

Benny Wong πŸ™Œ