2023 Year in Review

looking back at my first year on sabbatical

Anant Agrawal

Jan 16, 2024

*Knock knock

How was it?

*Sigh*, it was terrible

Oof, that bad huh, come on in

*Door closes behind me as I enter

I remember this date I went on. It was after work and I was so excited for it, but it went very poorly. I remember coming back from that date and my roommate, whom I had become inseparable from, asked me how it went. I said nothing, dropped off my backpack and headed down the hall. He understood and followed me: after all, he knew where I was going. I knocked on the door of our friends and for the next 2 hours recounted the whole incident to them, while we all laughed about all the things I had done wrong.

That was how 2023 started. I had a great roommate and I lived near friends. I was at my most comfortable at work. It really felt like, after almost 3 years, I had built a great community and life in San Francisco. Starting 2024, I have left my job. I have left San Francisco. What happened?

They say that sometimes to gain something you have to lose something too. I definitely gave up what felt like a lot at the time, but I gained so much as well and I am eternally grateful to all the people and experiences that helped me feel that way. I gained the experience of going on my first ever sabbatical. I gained the experience of starting this newsletter. I gained an appreciation for everything I gave up (all the important things anyway). To say 2023 was one of the most significant years of my life would not be an understatement. In this post, I’m hoping to look back at the journey of this year, and the journey of this newsletter, to really clarify everything I’m hoping to take with me into 2024.

When I started the sabbatical, and the newsletter for that matter, I had no idea where it was going to go. My attitude at the start can be summed by this hope that Steve Jobs talks about, “You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future”. At the start, there was nothing more than a vague mist of a plan to travel, write, explore new ideas, but looking back, it’s clear that the journey has phases. The phases were

January - June: Leaving my best life in SF (unlearning & discovery)
July - October: Becoming untethered (falling in love with being lost)
November - December: Settling into a new life (from discovering it to living it)

Leaving my best life in SF (unlearning & discovery)

For the first half of 2023, I had really grown my roots in SF. I was working full time in person and life was amazing. But, at the same time, I felt completely lost. I didn’t know where I wanted my life to go, just where I didn’t want it to go. I had been reading about exciting new ideas for months, and tried to apply them best I could to the traditional 9-5 job container I was in, but it just wasn’t fitting in right.

I officially started my sabbatical on June 1st and by the end of the month I had taken my first solo international trip to London. In this first month alone, there were two really big ideas I had taken away that I want to remember in 2024:

Unlearning and relearning

Finding a new lifestyle after leaving the old one

When I was working, I liked my job. I was always busy, my calendar was always full, and we were always working right up until the deadline. It felt good, it felt like I was building towards something. What I realized, however, was that even after 3 years at the company little was left for me at the end. While all those meetings had made me feel busy and important at the time, they didn’t amount to much now. While squeezing in as much progress as possible before the deadline felt great because of the adrenaline rush and surge of dopamine, the feeling had now long passed.

What had remained however was what I had learned through slow repetition. On the days when I was able to forget the meetings and the deadlines and just build my understanding about how something worked, when I took the time to understand what people really wanted, and when I was able to just sit and write, synthesize information, and come up with new ideas. All of that stayed with me, everything that I gained when in a state of flow and it was also joyful in a deeper and more fulfilling way.

This was the first big idea from my sabbatical that I want to take into 2024: unlearning and relearning what gives me the right energy during the day. Only after some distance was I able to start to unlearn chasing adrenaline and attention and start chasing flow. For the longest time, it never occurred to me that I could work a schedule different from 9 to 5, or that I didn’t just have to live in one place. I learned that I like to work in the mornings and evenings and take a break in the middle. In 2024, I still have a lot left to learn: I’m considering having 1 day a week where I have nothing planned socially or work wise and that I take off Wednesday and Saturday instead of Saturday and Sunday. 2023 has shown me how powerful it is to reclaim your time and energy and I can’t wait to get better at this in 2024.

Money, of course, is still needed to survive, but time is what you need to live. So, save what little money you possess to meet basic survival requirements, but spend your time lavishly in order to create the life values that make the fire worth the candle. Dig?” Henceforth I ask not good-fortune, I myself am good-fortune, Henceforth I whimper no more, postpone no more, need nothing. —Walt Whitman

Embracing radical freedom

Going on my first solo trip to London

When you go on your first solo trip, it’s natural to worry about feeling alone. When I went to London, I was prepared to find creative ways to find others to hang out with. What I wasn’t really ready for was the quiet. The quiet that came with having to make any decision whether it was about where to get dinner, when to wake up, or whether or not it was really worth it to travel 45 minutes to go to a church to sing with a bunch of strangers. On trips with others, I was usually happy to go with the wisdom of the crowd. When I was alone at home, I would often make a decision based on what decision I usually make in the same circumstance: where should I get lunch? How about the sandwich place I always go to? But being both alone and in a place where every decision about what to do was a novel one was almost a surreal experience: kind of like when you are left alone in the house for the first time as a kid.

At first, it is a pulsing feeling of absolute freedom. I spent my first day alone just walking around for 5 hours in any given direction with absolutely no care in the world. Being on your own means you can be completely selfish as you don’t have to worry about considering anyone else’s needs. But, after a while, what I realized was how hard being selfish really can be, because to do what you want you have to know what you want. Do I really care about finding a nice place to have dinner, or would I rather have a quick dinner and catch a show? Am I really not a morning person, or did I just like staying up in the evenings because, during a hectic vacation with family, it’s the only time I get to myself?

What I realized on this trip is how often you get caught up with the goals and priorities of others: you join a company with goals for your career, but end up just getting lost in helping the company achieve its goals, or you get so used to a decision being made for you that you never really stop to think if that’s what you really want. Today we so often hear praise for the virtue of being selfless and that is definitely an admirable virtue, but always having to figure out what I want helped me realize how often I don’t even know what I want, much less even consider it as part of the equation of what to do.

All of my ensuing vagabonding journeys, however, have been solo—which I’ve found is a great way to immerse myself in my surroundings. Without a partner, I have complete independence, which inspires me to meet people and find experiences that I normally wouldn’t have sought.
— Rolf Potts

So, essentially the first month of my sabbatical was about unlearning and dissociation. So much of what I valued and spent time chasing in the first half of the year (respect from those around me, being liked, etc.) didn’t matter when I went abroad alone. What did matter was my energy and excitement during the day, my self-respect and confidence, my ability to understand my environment and plan accordingly, figure things out as I go, and get along with whatever kind of people I may meet on the road. These are the things you take with you wherever you go and while I had a sense of them all beforehand, but the time off and travel really helped me realize how important they were and cultivate them further.

Becoming untethered (falling in love with being lost)

In July & August, after being gone for two months, I was back in SF for the first time since I left the job. I was so excited to return to familiar surroundings, but being back around what I was used to just made not going to work feel more strange. I did, however, get to focus on everything I had kept on the back burner. I started reading more, writing more, and finally started this newsletter. I also went on my longest ever trip abroad (to Japan in case I never mentioned that before) in September. Two big takeaways I had from this phase were:

All writing is not the same

Starting the newsletter

For most of my life I had thought of writing as an intellectual exercise. I understood the logic behind reflection and writing out your reasoning to do or not do something in order to persuade yourself or someone else. As a Product Manager, in a lot of ways this was my whole job. The first time I ever wrote something just for the hell of it was for a writing accountability group with friends. I don’t even remember what I wrote about, but I remember reading what the others wrote about. I remember reading about personal struggles and ways of thinking we had never talked about. These people were some of my closest friends, but I still felt like their writing had allowed me to get to know them in a way I just couldn’t otherwise. This writing was not trying to convince me of anything, it was just their thoughts on paper, but even more than their thoughts, it was their feelings.

It took over a year of these bi-weekly writing submissions before I published the first post of this newsletter. By this point, I was hooked. Writing for me was not just a way to remember a feeling or a moment, but a very part of processed what happened and how I felt about it. If I had an amazing conversation with someone from Writing Club for example, then simply recounting that experience in writing would give me the time and space to really feel all the excitement and energy of ideas that might have just flown past me in conversation. I felt more and I remembered more.

When I started writing, it was just a messy stream of consciousness that would not make sense to anyone other than me. With this newsletter, I’ve been more intentional about writing with a point in mind from the beginning. In 2024, I’m hoping to explore both further. I miss just writing what’s in my head and hadn’t even noticed that I had stopped doing this until recently. In the words of Joan Didion, I write to know what I think. At the same time, I want to invest more in this newsletter and improve in the craft of writing. I’m considering branching out from just talking about my own life and experiences (which I’ve started doing through the Explorations section) to tackling bigger questions that have always interested me such as how do stories change how people think and feel, how can platforms better foster a public square of discussion while limiting hateful speech and misinformation (brought about by no specific incident in particular), what is the best way to govern an organization for the benefit of its members and the people it was created to serve?. I’m hopeful in gaining inspiration from writers whose work I love to read like Elle Griffin who writes The Elysian and Lawrence Yeo who writes More to That.

Everything Is Interconnected

Going to Japan

When I booked an “authentic” buddhist experience on Viator, I was worried that the experience would be anything but authentic. Imagine how much better I felt when I learned that the person who was going to teach us about this religion we had flown 5,000 miles to learn about was named Brian and was originally from the country we just left. But when Sensei Brian started to tell us about the big ideas in Buddhism and about his own life story, my fears quickly evaporated and turned into awe.

One of the many big ideas that stuck with me was that everything is interconnected: we think of most things as different and yet they are not. When Sensei Brian was a Christian missionary tasked with converting Buddhist monks to Christianity, he certainly saw the two religions as different. But when he himself converted to Buddhism, and then wrote two books about terrorism within the religion, he began to believe in the doctrine. He explained how could have never seen how being a missionary in Nebraska was connected to becoming an author in Japan, but how he can now see how every part of his journey shows up in his present life.

His story helped me realize how the same could be true for my life. When I started my sabbatical, I thought the biggest challenge was going to be picking the right things to learn more about or look into. I was hopeful that being really intentional about choosing what to learn about would ensure that I wouldn’t waste time learning something that was not going to be helpful in the future. But taking the lesson that everything is interconnected to heart, I’ve realized that I have never regretted learning something, no matter how irrelevant it may seem at the time (I thought watching TV would be useless to me as an adult, but it’s become a big part of my newsletter). It’s amazing how things can connect to each other and just what connects and what doesn’t and so I’m trying to worry less about choosing the right thing to learn. I have poor discipline and so if it doesn’t resonate with me, I usually end up giving up quickly anyway, thereby making the cost of a wrong turn low.

It is important to draw wisdom from many different places. If we take it from only one place, it becomes rigid and stale — Uncle Iroh

Now that I had some time to disassociate, in this phase it was time to find answers. Most of what I was writing and thinking about was what made me happy, defining what I was hoping to achieve through the sabbatical, what habits I wanted to establish. It mostly just a lot of trial and error through different projects (starting this newsletter, analyzing member engagement for different communities, creating content for an AI governance company), but also different ways of living (not working, working remote, working part time), and hearing about different approaches to life (suburbs life, life of travelers in hostels in Tokyo, of monks in Kyoto, and those on sabbatical that were visiting SF).

Settling into a new life (from discovering it to living it)

After 6 months of moving around, I was done. I feel like I had gotten it all out of my system, and now I just wanted to build roots somewhere. I felt that the best environment to reinforce what I wanted now was NYC and decided to give the city a shot. I spent November & December going back and forth between NYC and Boston. I had an incredible time in NYC. My writing & lifestyle had also changed from 100% discovering new ideas to a blend of trying new things and tangibly putting what I learned into practice when thinking about work and how to spend my time.

Exploration as a Lifestyle

Settling someplace new

When you’re traveling, it’s easy to be fully immersed in exploration mode since you are constantly surrounded by novelty, but what about once the trip is over? What is the right balance between commitment and freedom? Moving to NYC really brought this question to the forefront of my mind. What I realized is that choosing between the two can actually be a false dichotomy. Always moving around was not a pure expression of complete freedom, it also limited my freedom to be able to do certain things: the slow things that build up over time such as building healthy habits, learning something new, or really getting to deepen a relationship with someone. These were the kind of important things that were so difficult to prioritize when just figuring out where you are going to stay and what you are going to eat is an attention consuming puzzle.

So I decided that planting my feet somewhere would not be the end of my sabbatical, but simply the continuation of a different form of exploration. My expression of this philosophy was to try to be an indie consultant or freelancer. As I discussed in my post, Total Football, the goal was to try new things, but beyond that to improve my ability to listen and understand what speaks to me, to understand how things are changing around me, and to be able to learn quickly and be able to adapt to any changes. This meant building systems around improving my information diet, being around people who are actively curious and also experimenting, and just taking courses, reading books and building back the skill of learning something.

I had taken steps in this direction in 2023, going to an AI Film Festival, a Risk Management Conference, and a freelancer MeetUp as well as pursuing a Civic Tech fellowship. Being so new to these interests and around experts made me feel like an easily identifiable imposter. However, the encouragement I received from those around me and the amount I was able to learn by attending gives me the confidence to dial up such activities in 2024 (while of course hoping to avoid the pitfall of the Dunning Kruger effect). I’m also hoping to go deeper into new topics in my writing, sharing what I’ve learned about whatever topic I’m learning about through Playbooks and Essays.

It’s funny. When I first came to NYC for a month to visit in May, I was working a full-time job and yet spent a lot of time just exploring the city. In November & December, I spent about another month in NYC, this time having moved there, and I spent most of time inside my apartment working. But I was still exploring, just doing a different kind of it.

Looking Ahead

When I moved to San Francisco, it took me 4 months before it really even started to feel like home and over a year to find communities I was proud to be a part of. After one month in New York City, I’ve already come across a few communities that resonate with me and started to build a new routine I feel comfortable with. Part of it is because the city is just helping me manifest what I’m looking for (I made my first friend on my first day talking to a stranger in a restaurant and ran into another former Product Manager interested in writing a screenplay at an event). Part of it is because friends and communities from San Francisco pointed me in the right direction. The last part is just that I’ve grown. After all the chaos of this year, I feel that I have become better at starting over and adjusting to different circumstances. In 2024, I’m excited to capitalize on all this momentum and energy in a place that feels like it is spurring me on.

In terms of the newsletter, I feel great about how it has turned out so far. This is going to be the 20th post of the newsletter after being live for ~ 6 months. When I started this newsletter it was just for me. It was a way to process and record everything I was learning about on my sabbatical and improve on the craft of writing. Now, in 2024, I have a few people along on the journey with me. This year is focused on learning new things and understanding the answers to different questions. To better understand these questions I want to get better at research and reasoning and I’m also hoping to get better at storytelling and exploring different formats to convey different ideas. I would also love to build more of a community of writers to get ideas from and to hear more from you, what’s resonated most for you and what ideas are you most curious about?

2024 is probably going to have less travel (but still likely a fair bit) and be more about leaning into what work I want to do. I’m excited to see where the work I am doing now takes me as well as take the time to just sit somewhere and read more about the questions I am curious about. I am also just looking forward to leaving space open for the unexpected. I could not have planned 2023 or had any idea where it was going to take me and I’m sure the same will be the case for 2024. But this year I feel more sure about what I want and what I am looking for and more prepared to take whatever happens in stride. I suppose we’ll just have to see what happens!

P.S. I also just want to thank everyone who has taken the time to read anything that I have written. You all are the wind in my sails and it brings me so much joy to discuss these ideas with others. Please don’t ever hesitate to reach out to chat ^_^!

Unscripted Wanderings

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