6 months later: A sabbatical reflection

what I explored, what I found out

I quit my job in May 2025. I wanted to go independent. I wanted a spiritually aligned career. I wanted passive income and published assets. I wanted time and space for creative pursuits.

My side projects had bloomed so much that I believed I could create a career out of them. And so I quit, and allowed my desire to try something overcome my fear of uncertainty.

You can witness my thought process from my youtube updates during this time:

During my time, I ended up having a lot more financial stress, laptop issues, and social needs than I expected. I was also surprised with how much spontaneous flourishing emerged— I created a thriving friend slack, hyperstitioned a ~200-person pop-up village, and gave a talk at a conference.

By six months in, I had explored many paths and discovered my aptitude for or lack thereof in each of them, as well as the unfortunate details of living in these alternative futures.

Key lessons and insights

As it turns out…

• Intrinsically joyful work sours when I try to do it for anyone else.

• I am sensitive to financial scarcity, even when I have decent savings. I cannot be a starving artist— I need to be relaxed to do creative work.

• I am not willing to do part time / contract / freelance work as it feels too scattered, low context, and low commitment to be satisfying.

• It is hard to make an independent career that pays as well as my job as a product designer in AI/tech. I only want an independent career if it makes at least 50% of my full time job, with an appropriate ratio of effort to income.

• I am now even more in love with my artistic vision and creative voice. I like myself best when I am making films.

• I cannot conjure up excitement for working in the dating/romance space.*

• It will take years to build up content/assets into a sustainable income flow.

• I cannot simply ignore social dynamics. I need to allocate time for socializing within any new container I join, otherwise it is difficult to get work done.

Okay, so what happened?

I explored paths across:

• Film

• Design

• Coaching

• Content Creation

• Cuties! (dating startup)

• Community Building

• Small Business

• Experience Design

What I explored

I found out a lot about myself and the fields in these explorations. You can see a table view of the below in my google doc (recommended).

1. FILM

I dedicated my days to huddling in my tiny closet of a NYC bedroom, working with Premiere Pro alongside ChatGPT.

My learnings:

• My self-learning pace is agonizingly slow. (This improved once I bought a new laptop).

• The quality of output was mid/not very professional. I am clearly a novice using an iphone.

• My films lack story & structure— they are driven by emotion, tone, and ambiance.

I made 3 short films

• Paralysis

• On stances

• SF to NYC

They feel honest and indicative of my style. I love the moment a concept takes its first breath and comes to life.

Working in film

• I worked on the movie set of a major Marvel production! I spent 2 days working 15+ hours per day as a PA (production assistant) rerouting pedestrian traffic. My name will appear in the credits.

  • The experience of working on a major movie set was wild! Imagine burning police cars shooting backwards as motorcycles and stunt men flip over them.

  • It was devastating to work 15+ hours of menial labor to earn the equivalent of ~2 hours at my remote tech job.

• I landed a gig making youtube shorts for a tech podcast. My friend also proposed we collaborate on a film on agency.

  • I discovered I cannot make myself care about making content for others. I am only motivated by my own expression. I can barely answer emails for someone else’s project.

  • I made some friends in the film scene and we started running ad hoc film nights.

Applying to film school

I applied to film school! This proved to be a difficult process that forced me to reckon with how serious of a filmmaker I am. Do I want to make films or do I want to have made films?

• Film school will cost over ~$400K in total ($80K tuition + $30K living expenses, annually for 4 years).

  • This is too much! It would mean I go into debt, and sacrifice my budget for house + kids.

  • I decided film would be something I take on later in life, after I have had kids and secured financial abundance.

• I learned that I love my voice. I believe in my artistic vision. How lovely, to have conviction in this. I also loved the process of creating stories for my application, which confirmed I do like making films.

2. CONTRACT & PART TIME DESIGN WORK

I got a few leads for design contract work.

• I discovered part time/contract work is too scattered, lightweight, and noncommittal for me to really care or get deeply involved with a project.

• Hours are sparse.

• It was fairly easy for me to find leads for contract design work.

• Contract design work is lucrative. I can charge $100 – 200/half hour.

3. COACHING

I coached 8 people on various topics, from relationship dynamics to social media marketing to life perspective.

• I found out I dislike coaching. I have a hard time establishing enough connection with a stranger to dive into their emotional complexes. I dislike online meetings in general. I also don’t want to join this ‘lineage’ or line of work.

• I discovered there exists demand for me to coach. I charged $100/hour and provided notes and suggestions. It’s too bad I don’t like coaching, since it presents a viable path towards an independent career.

4. CONTENT CREATION

I create content across multiple platforms: Youtube, Patreon, Twitter, Substack.

• I started a travel vlog at the beginning of the year, which I found to my surprise that I quite enjoyed. My channel grew to 650+ followers, which meant I was halfway eligible for Youtube earnings (I still need more watch hours). I became hopeful about becoming a content creator. I researched content creation as a career and discovered that you can make as much as $30K/vid (!) if you go viral.

• On X, I already make about $120/month from 12K followers. I set up my Patreon and pitched it a few times on X. I make about $160/month from Patreon. I continued writing on Substack. I set up a few paid posts then turned them back to free… I don’t yet feel a compelling reason to make any of my posts paid, considering they are fairly scrappy. That being said I make $96/month on Substack.

  • Currently I make $376/month from content creation. This is utterly inadequate. While there is a feasible path toward an independent career, it will take years of effort and significant cycles iterating upon and developing my assets for engagement.

  • I don’t know that I want to join the lineage of content creation, nor do I feel that excited about identifying as a full time content creator. I am wary of getting trapped in the engagement/optimization trap.

• I will continue to nurture and create assets/ essays/vlogs as I see fit and naturally enjoy.

5. CUTIES!*

• I created a pitch deck and circulated it with ~10 of my closest investor friends. After getting much advice I did not get much commitment. The common response was “figure out what you are really excited about and come back”, or “how will this make money?”.

  • I could have kept pitching to 500 more investors, but given that Cuties! is a community based app, I was looking for more positive signal from my closest connections.

  • I learned that momentum is important: there were a few investors who were interested, but without a timeline their interest waned. Next time I will use a timeline to create more momentum.

  • Most troublingly, I had a hard time feeling excited about going all in. I consistently felt a slight aversion to dedicating my life’s work to dating/romance.

  • I also presented at the Love Symposium.

• (you can join cuties here)

Bootstrapping

• I found a potential cofounder and a lovely agency, CodiTech, to work for me for free in return for social media exposure. They fixed all the main bugs in Cuties!

• I tried charging for a few premium features: 1) $3/month for more likes, and $100/30min for a dating profile analysis and coaching call. A few users bit my premium features, but very few (under 10).

• I toured different communities and cities and hosted Cuties! Events (NYC, Edge Esmeralda, Vibetober, Love Symposium). They were somewhat successful and not particularly exciting.

• I discovered coaching calls for dating profile analysis is even more lucrative than normal coaching ($100/30min). Unfortunately I do not enjoy it.

• I hosted Cuties! gatherings:

  • NYC cuties picnic

  • Cuties @ Edge Esmeralda

  • Cuties x Chess during Vibetober

  • Cuties x Bookbear Express Love Mixer

• I learned that even with the associated wins (finding a cofounder, finding a dev agency), I still was not motivated to go all in into the dating space, and Cuties! is necessarily a dating app because being single is the main pain point that drives people to join.

  • I do enjoy building Cuties! as a service project. I am delighted when my friends find love, friendship, and opportunities through it.

  • I decided I am more interested in the areas of social infrastructure and prosocial community projects. There’s a question here of if I should try to pivot, and I do want to explore this possibility.

6. COMMUNITY BUILDING

A friend introduced me to Verci, an adjacent community in NYC, and I visited as a prospective community manager. Despite it being a very cool community, I realized I definitely do not want to manage a slack, organize events, or develop expertise in event set up for strangers/other communities.

I attended community builder events & forums to network with other community builders. From listening to the experiences of other community builders, I confirmed that I do not want to be in the business of event organization, remote meetings, and venue set up.

7. SMALL BUSINESS

I tried making a business website and formalizing my offerings. Formalizing my offerings was hard. I got stuck on legibility and inner skepticism around the value of my offerings.

I plan to continue pursuing this thread— I will continue to practice designing immersive experiences, making conceptual films, designing, hosting, posting on social media, writing, creating content, coaching, and making social tech, so that I can someday have structured offerings listed on a business website.

This is my best bet as of now. I want to continue developing my interests until they generate enough revenue to replace my job.

Take a small business online program

I considered taking an online program for starting a small business for women. I looked at Online Biz Academy and Stacking the Bricks. I learned it costs several thousand dollars, but also it was a revelation that this type of program exists to walk you through the process!

I think I do need a program like this to make a career shift. I struggled to do it on my own— however I now feel supported in my desire to one day set up an independent business. I will likely take this program in the future.

8. EXPERIENCE DESIGN

I considered taking an experience design certificate program with Odyssey Works. I visited the graduation exhibit and was satisfied with the artistic intent and quality of the student show.

I feel that experience design is largely an artistic, social, and spiritual pursuit, and thus not particularly profitable. I found that I definitely have strong curiosity in this direction! I plan to take the certificate when I have time.

Avenues still not tried to my satisfaction:

• Indie hacking / vibe coding AI tools. I plan to start a club to play with AI coding tools with some friends in the coming months.

• Networking. I pretty much never reach out for coffee. I can be more intentional about building relationships with people in NYC.

• Social infrastructure space. I am considering another iteration of Cuties! that focuses on bridging adjacent communities, as this is the main area I am excited about.

• Hyperstitioning. I have a decent signal from Vibetober that I am good at hyperstitioning and mimetically activating the social field. It feels like playing with magic. I’m not sure exactly how it works but I am having fun.

• Building my corpus. I am currently running Inkuary, where we write/publish every day for the month of January. ~65 people have joined. My personal aim is to continue writing and explaining my perspective.

Other obstacles

Besides the situations discussed above, I ran into a few issues:

• I was stressed about money (living in nyc is expensive). I thought I would sit and work at cafes all day, but it turned out buying a $7 latte would stress me out.

• My personal laptop was old and dysfunctional. Since I gave up my work laptop, I had to use my personal laptop from 2019. It would overheat so much that my fingers burned and my knuckle joints ached from the heat after typing for a while.

• My living situation was uncomfortable. I was subletting from friends who were letting me pay a cozy $1000/month in rent. However this meant I was in living in a tiny windowless room with other people’s storage. I was unable to sleep due to heat and lack of air circulation. I was constantly uncomfortable and couldn’t focus on my work!

• I felt socially disoriented in a new city. I didn’t anticipate how much time I would need to socially acclimate when moving to NYC. I tend to think I can just ignore social dynamics, but I definitely need to feel oriented before I can ignore everyone and get to work. I spent a large amount of time getting to know new friends and friend groups in the city.

• I had to pay out of pocket for a million tools and their subscriptions (Claude, Loom etc). Every single AI and SaaS tool came with a paywall. This was stressful as someone without an income.

• COBRA Health insurance was ridiculously expensive. I paid $700/month for 6 months.

Other wins

• I created a thriving friend slack. After I quit my job, I craved daily community, accountability, and structure. I also happened to have just introduced all my friends to each other at Vibecamp, a post-rationalist festival. I started a friend slack and it immediately became a thriving and nourishing space of daily chatting, inspiration, and updates. Since the people were all my close friends, it took no effort to maintain.

• I hyperstitioned Vibetober, a month-long ~200 person decentralized pop-up village in NYC. The slack led to the unfolding of Vibetober, in which 200 people from all over the world descended upon NYC for the month of October. Other than some light scaffolding (a partiful, calendar, and group chat), it was a largely decentralized and self-organized affair, with everyone figuring out their own lodging and making plans with their closest friends.

• I threw 2 experimental art parties. My friends and I threw the Birds and the Bees, a celebration of high summer and community cross-pollination, and The Threshold, a surreal and ritualistic halloween party. Both were great successes in my eyes, which was a relief given past failures. I attribute these successes to having competent and enthusiastic cohosts who were aligned on delivering an immersive and transformative experience.

• I hosted christineist film festival. I presented my films to my friends in a terrifyingly earnest gesture.

• I took improv classes and confronted my performance anxiety. At the end of the 7-week class we performed a show, which thankfully went really well. It was a powerful disconfirming experience for my stage fright.

• I gave a talk at the Love Symposium conference. My improv class and exposure to being in the spotlight led to my accepting an opportunity to present at a conference. I gave a talk! Another big win for reducing performance anxiety.

• I cohosted a love mixer. I collaborate with Ava and Cleo to run a singles love mixer. It was a great success, with ~100 participants and widely positive feedback.

• I traveled. I roadtripped from San Francisco to New York City, I visited Edge Esmeralda, I went to Vibe Gala and Vibecamp, I went to a weeklong party in a castle in France, I traveled around Portugal and China.

• I spent a lot of time on another goal, which is finding love. I read the book Calling In The One by Katherine Thomas, and worked every day on its meditations and practices. I reviewed it here. A major reason for my living in NYC is the dating pool.

• I found I continue to really love NYC. I am happy to report I consistently feel good and aligned about choosing NYC as my city and a place to live. I love the weather, the architecture, the fashion, the conversations I overhear etc.

After 6 months in…

I had many ups and downs, as evidenced in my youtube updates:

I had tried many things, and perhaps none to a serious enough degree to get real traction? It is not clear. In the meantime I was getting nudged out of my cheap sublet, and I yearned for better living conditions.

Late one night, as I lay sweating in my hot stuffy air duct of a loft bed, I absorbed reddit posts on how film school graduates make $40K two years after graduation. I freaked out and immediately applied to a bunch of jobs with some light research. A few weeks later I got an email to interview.

(While I landed a job fairly quickly, I have friends in design/engineering/data/marketing who have had a difficult time landing a job. I attribute my ease to having prior work experience in AI. Demand for AI talent is especially hot right now compared to other areas.)

I speedran a portfolio in 48 hours and entered an 11-round interview with an AI/ML startup. I ended up landing an offer.

I decide to take a job offer

It turned out I didn’t just want any job. I looked at many job postings and had a visceral adverse reaction to certain industries and problem spaces. I realized that compared to other possibilities (eg, e-commerce, accounting, fintech) I quite like the AI/ML space. The problem space feels intuitive and interesting, and like I *get* to learn the math behind model training, as opposed to something I have to swallow.

I also discovered to my pleasant surprise that this job was a good fit:

• I agree with how the company understands design process in the age of AI

• I really like the manager

• Great pay and benefits

• Flexible hybrid set up

Thus after many interviews, I decided to take the job offer.

How and why I decided to take a job again

• I really, really, really wanted an apartment. It was surprisingly difficult to get an apartment without proof of income. My suboptimal living situation made everything untenable— I could not focus because my room was a closet, because I couldn’t afford an apartment, because I was unemployed, and this was a major problem. I decided to prioritize getting an apartment and getting established in the city.

• I was hitting the 6 month mark. I was eyeing my 6 month mark of unemployment. With the pace of AI developments, I felt I would fall behind if I was out of the game for more than 6 months.

• I had no strong vector or leading direction to pursue. I found that despite exploring many paths, I did not feel a clear signal towards any particular alternative career.

Conclusion

The sabbatical didn’t lead to an independent career, but it brought me clarity on my desires, my nature, and what’s involved in pursuing this path. Quitting my job gave me time to explore and test myself and my resolve.

While I am back to employment, I feel fairly aligned with my current strategy. I will develop my career in design and machine learning, which will fund my interests in social infrastructure, content creation, experimental film, experience design, and community building. The financial cushion will allow me to relax into creation, build publishable assets, and set up a business with packaged offerings. I will be patient and develop my personal mix of independence and financial security.

Looking back, I am very glad I took this time to investigate what’s involved in an independent career. It feels extremely satisfying to take a few steps down various paths and slip into a different life or three. I have a higher fidelity understanding of what resonates and what is feasible, which makes certain rosy futures less dreamy and more tangible. If I hadn’t done this, they would certainly remain “what ifs” with infinite haunting power. As it is, I feel good about where I’ve landed, and I believe in myself and my ability to quit again if I want to take yet another risk in the future.

Thanks for reading if you got this far! I welcome any comments, challenges, suggestions or feedback!

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Update: Added a video about designing your own sabbatical!

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*Cuties! Is a dating app I made as a side project for my friend. It took off on twitter and now has ~2000 users and has led to 1 baby. I received some investor interest in the months prior to quitting my job, and I wanted to investigate if I could raise funding or bootstrap into a stable revenue engine. Join Cuties!