Billy's Thoughts

Sabbatical: July - October

Posted on Nov 10, 2023 — 18 mins read

I’ve been on sabbatical since July now. And up until October, something new would shift for me literally every two weeks. This post is intended to be a record of all of those changes, so I don’t forget this crazy, wonderful time.

The timeline

How it started ↩︎

My thinking around taking a sabbatical was as follows:

And so I started on my break with the goal of finding a more fulfilling way to work.

(“Because that’ll make me happy!” is what I think I was subconsciously tagging on here. More on this to come.)

July, week 1-2 - Objective #1 - Find a more fulfilling way to work ↩︎

I’d been mulling over ideas for months, planning, because that’s what you’re supposed to do when you’re trying to branch out into a new career, right? I looked at what I enjoyed doing, and what was most viable to eventually bring in income, and I landed on:

  1. Try to start a life/career coaching service
  2. Continue writing on the side, because it’s fun and it’s also a very useful meta-skill to build (and who knows, maybe we even build an audience along the way)

Then came the over-engineering. I couldn’t just snap my fingers and magically get coaching clients! I had to make sure this idea had the highest chance of succeeding. And who would want to talk to me, someone they knew nothing about? So instead of general life coaching, I narrowed my focus twofold to: tech interview prep (which I told myself could eventually expand into tech career coaching, which could expand into more general life coaching). I figured I had to get my name out there and build an audience first, in order to maximize my chances at getting clients. Which meant posting on LinkedIn, which meant writing up my thoughts in some marketable form.

And so the first couple weeks of my sabbatical were equal parts me drafting marketing copy, and procrastinating because it turns out I found this to be not-fun and tedious, actually.

Whew. Somehow I ended up here, writing promotional material instead of doing the actual thing I wanted to do which was talk to people! But at the time, I couldn’t see my predicament for what it was: trying to ‘set myself up for success’ while also avoiding doing the thing itself because I was afraid to fail. Why? Because I’d latched onto the idea that finding a more fulfilling way to work would fix this dissatisfaction I was feeling, so I NEEDED this to work. (Spoiler: this approach still failed in the end anyway haha.)

Getting another perspective - Give Your Gift ↩︎

Around the same time, through the magic of tweeting my thoughts + having great twitter friends, I joined Give Your Gift, a sort of incubator for people wanting to do service projects.

On paper, GYG lined up fabulously with what I was looking for:

I was all for getting another perspective on my plans, especially from a slightly different emotionally tender and service-oriented angle.

And it turns out this was exactly what I needed (and I would have never been able to guess it at the time).

The first part of the process was deciding on my service project. When discussing my plans for coaching and writing with Tasshin and Mary, I guess it was clear that I wasn’t really enjoying myself. Instead of receiving affirmation, I was nudged in a different direction: “What are times/projects in the past where you had the most fun? What would a purely fun project look like?”, and then “What if Having Fun satisfied the ‘service’ part of the service project?”


This cracked me open and revealed one of my blind spots. Why was I so focused on being productive and providing value over having fun? Why did I feel like I couldn’t just do a project purely for fun, like a music project? In fact, the idea had never even crossed my mind.

I took a walk to try to process things. And that’s when the floodgates opened; I inadvertently stumbled over The Threshold, in the hero’s journey sense.

I was struck by the realization that: I felt I needed to be Good, to be perceived as Good, to produce value, in order to be loved.

This was an honest-to-god, classic “holy sh*t!” moment for me. And it didn’t stop there. Dots connected to past experiences and past excavation I’d done with my therapist, and questions popped into my mind like fireworks:

I remember doing a deranged-villain-laugh at some point. “Oh god, I thought Getting Good would solve all my problems but it hasn’t, and it won’t,” I realized.

I wrote down as much as I could in my notes app, trying to hold onto every branching thought, like cupping water in my hands, afraid I would lose track of trains of thought permanently if I didn’t preserve them.

I wrote and I processed, and that calmed me down. My rational brain finished rebooting, too.

The scope of all of this was massive, and I knew tackling this internal hole that craved external validation would be a long-term process. There would be no silver bullet, no instant-heal spell I could cast. But I knew the general direction to go in, something like: digest the root negative emotions over time + find creative ways to manage the ego in the present. Awareness is the necessary first step to change, but they don’t tell you what to do after that because that’s where the generalizability ends and you have to find your own way.

Plus, I still had a pressing issue to deal with - what was I going to choose for my service project??

Objective #1 - Find a more fulfilling way to work - PAUSED

July, week 3-4 - Objective #2 - Reconnect with Fun ↩︎

To challenge the idea that I had to be productive, I took Tasshin and Mary’s advice and reoriented around fun–what would be a fun project that I’d be really excited about?

So I decided to do a drum cover of Mine by Taylor Swift.1

After that, the rest of the details quickly fell into place. Picking a project idea? A f*cking entire character development arc apparently. Executing a project idea that I was excited about? Eaaaasy. I’d been executing for the past 7 years at my job after all (effectively, I might add). And so my schedule became as follows: 3 weeks to finish learning the song, 1 week to record, 1 week to edit, and then we’re done.

And things went more or less according to plan.2 And it was fun!3

Here’s the video:

Objective #2 - Reconnect with Fun - DONE

August, week 1-2 - Objective #3 - Meander ↩︎

… So what now?

GYG was done. I had my big realization, and then I challenged it by doing my drum project. But honestly, I didn’t feel all that different. It was like taking a single step through fog: you’d still be in the fog… The only way out is forward. But where was forward?

I thought of a few options, but none felt like MUST-DOs:

In the end, I didn’t hard-commit to anything. I continued to play drums daily, with the lightly-held intention of finishing learning Red in a couple more weeks (it’s harder than Mine). But overall, I distinctly felt like my heart was determined to meander.

The neutral zone ↩︎

During this time, I was also reading my way through William Bridges’ book Transitions.4

Bridges beautifully captures the state I was in: “It is as if we launched out from a riverside dock to cross to a landing on the opposite shore–only to discover in midstream that the landing was no longer there. (And when we looked back at the other shore, we saw that the dock we had left from had broken loose and was heading downstream.)”

This is a state of disorientation–of not being able to return to how things were, and also not knowing where things are going–that Bridges calls “the neutral zone”. It’s where your previous instruments of measure, your compasses and your North Star which used to be clearly legible, now appear like gibberish to you.

And the tricky thing about the neutral zone is that you can’t force yourself to suddenly become reoriented again. You can’t force yourself to take on a new direction. Frustratingly, true reorientation of the heart happens on its own, when you’re ready, whenever that may be, due to whatever circumstances.

Reading Bridges’ writing, I could see I was firmly in the neutral zone, and since I had no other reliable instruments of orientation (besides Having Fun), I was inclined to believe him: my reorientation would come when the time was right. In the meantime, I would just be. Hence, meandering.

I played drums. I played Street Fighter 6. I went to the gym. I watched Oppenheimer, and then Harry Potter and the Order of the Phoenix in concert. I watched a lot of youtube videos, mostly VTuber clips and podcast interviews. I probably did a lot of other things that I can’t recall while writing this post, and maybe that’s exactly as it should be.

August, week 3-4 - A door appears ↩︎

Eventually, somehow, someway, reorientation begins…

In my downtime I enjoy the occasional Dr. K youtube video, whether it’s about mental health, eastern philosophy of mind, or it’s an interview with some online content creator that turns into a pseudo-therapy session. And while meandering, I came across his interview with a steamer named Dantes, and it turned out to be the next thing to unlock something for me.

This interview resurfaced the idea I first encountered during GYG, that for some people, a part of them yearns for external validation to provide them a sense of self-worth (in Dantes’ case it’s Appearance, in my case it’s Recognition).

The interview also went a step further and connected this self-worth gap to the bouts of Emptiness I would occasionally feel at the end of a long day, to a broader sense of dissatisfaction or lack of fulfillment with work and my achievements. My current state was never Good Enough, and there was always something to improve on.

Around this time, I also had a sort of mental vision, where I saw my future self who had succeeded in making the coaching thing happen, and I was living the life I said I wanted–working 5-10h/week making $500/h for coaching, and having plenty of downtime to write and pursue other interests. Except I felt it in my bones that, inevitably, my future self would start to feel bored and accustomed to things, and eventually become dissatisfied. Again. And I would start looking for something new, some next adventure to bring me more fulfillment…

Sound familiar?

… Hold on… Was my desire to take a sabbatical, to find a more fulfilling way to work, actually just another manifestation of this self-worth gap? Was I chasing after a red herring?

To use a coding analogy: Was I staring at a pointer this whole time?


This cracked me open, again. Except this time it was much more intense.

I felt like I uncovered a whole new dimension I couldn’t perceive before, like the Square in the story Flatland when he’s shown Spaceland. I felt supercharged with a combination of shock, joy, and giddiness. But different ball of emotions began building too, around thoughts like: What do I even know? What was I even doing, if I didn’t know my own underlying reason for taking my sabbatical?? And is there more I’m missing? Does this go deeper still? Was this cycle of chasing after satisfaction ever going to end?

I tried to do some processing around this through journaling and talking to my therapist, but the problem felt much larger than when I first encountered it during GYG. It’s like in video games, when you defeat the boss only to find out it has a second, more powerful form that you have to fight too.

I was reminded of what I had to do, and I also knew it would take a long time, which was frustrating. Emotional wounds require emotional healing, and the chase for satisfaction through external means would end when the internal, the self, became enough. Awareness was the necessary starting point. And my next step would be to try and notice when thoughts come up that are generated by my self-worth gap, and challenge them in a way to try and overwrite those thoughts into slightly more positive ones that I believed. But that sh*t is hard work!

Funnily enough, life got busy right after this realization, so I didn’t have too much time to sit idle and stew. I started drafting this post, but I was mostly busy doing IRL stuff: I saw BLACKPINK VIP, flew home to visit my parents (they’d have my hide if I didn’t visit when I had no job to get in the way), came back and then immediately drove off to Disneyland, only to come down with COVID upon returning home :(

September, week 1-2 - Descend ↩︎

I was sick, then I was recovering, then I was trying to get back into the swing of things. I was writing again but I struggled with the early drafts of this post, so I wrote about The Emptiness instead. And I continued to meander in other areas.

Then, as if summoned by name, I was hit by a period of Emptiness unlike any I’d felt before, lasting for days when it usually passes after one good night’s sleep.

I was in an abyss. I felt lost. And not just emotionally like I did when I was meandering. I felt it in my body. Like there was a vortex in my gut that tugged on my insides and drained me energetically. It was like I had a spiritual hunger that I didn’t know how to fill. I felt like I was cloaked in a sort of dull darkness.

My thinking was affected too. I lost the ability to separate myself from the self-worth gap–It became me, and I became It. I saw all of my past decisions in life flash before my eyes, and I saw how The Gap influenced each and every one of my choices. And further, I couldn’t see how future decisions wouldn’t also be tainted by The Gap. It was there all along, and it would continue being there for a long time, as I worked to heal it.

I knew I wasn’t thinking clearly. I knew I was catastrophizing, I knew I was thinking in black and white. But even so, I wasn’t able to break out of this funk. It was the same feeling each day.

Thankfully, the Transitions book came to my aid again, and I found encouragement to try to unclench as much as I could and accept that this is where I was. I resolved to just exist though it. Feel these feelings. Continue working on what I could, when I had the energy, and trust that it would clear eventually. “This too shall pass”, and all that.

September, week 3-4 - Emerge ↩︎

I was stumbling around in the dark for about a week, and my memory of what I did during this time is fuzzy. My notes tell me I was decently productive: I wrote and rewrote drafts of this post, I tested recipes in preparation for my 30th birthday dinner party that was happening the following weekend, I read books, I played drums, I started a new singing cover. I spent a day or two laying in bed indulgently rereading some of my favourite fanfics. But no matter what I did, I’d always return to feeling the blues after.

Then, whether by correlation or causation, I don’t know, I went out for the first time in a couple weeks and hung out with friends in the park. And the clouds started to part.

What broke me out of my funk completely was this moment: I was in the shower after a workout, when I was suddenly struck by the idea that I could give coaching another go. But this time I could just try to do the thing directly with as little overhead as possible, which could just be posting a calendly link on LinkedIn.

Now, I distinctly remember feeling The Emptiness when getting into the shower, and I distinctly remember feeling light and giddy and alive again after exiting the shower. I’m not entirely sure what happened here, but my suspicion is that it was some combination of:

  1. This idea was an incredibly simple and elegant solution to a problem I’d been thinking about on and off for months; and
  2. This idea felt clearly untainted by the self-worth gap I’d been hung up on

But whatever it was, I knew I was so back.

By the following week, I was full steam ahead on Doing Things again and running this new coaching experiment, as well as recounting my experiences when friends would ask me what I’d been up to, which helped me in my writing process too. I still didn’t have any long-term mission or goals, but I was content with just being energized and active again in the short term.

October - Objective #4 - Keep doing creative work ↩︎

It was nice to have a primary focus again, which for me became: (1) running my coaching experiment, and (2) writing this post.

(I’m just now realizing as I write this section that this is exactly what I was trying to do at the beginning of my sabbatical in July. I am literally laughing and shaking my head right now, haha.)

I also continued to meander on the side, doing non-primary-focus things like:

But this time, even though part of me wanted to fast-forward the progress on my projects and get to someplace stable, most of me was able to just be, and enjoy.

This is where the next shift in my perspective emerged from, as a sort of culmination of all of this development over the past few months. My new direction: Keep doing the creative work that you enjoy, and do whatever it is you need to do to keep at it and stay in the game. I wrote more about this here.

  1. With enough time and natural introspection, I realized that I would probably really enjoy learning the drums. Drums are like pure embodied enjoyment of music; they’re like a rhythm game but you’re actually playing the song. And I already adored rhythm games. ↩︎

  2. Like with any project, there are going to be “live production issues” that come up, fires to be put out, obstacles to work around, etc. For my drum cover, these included:

    • Camera testing and figuring out angles and lighting, with just 2 cell phones and some tripods
    • Figuring out how to record a good take and managing my psychology - I recorded my 4th take, felt it was pretty good, and then I decided to record a 5th take for fun, felt way less pressure, and the 5th take ended up being the best one
    • Weird desync between the MIDI recording of my playing vs the actual song - the audio through my drums was something like 1.5% slower than the actual audio
  3. Working on my drum cover for ~5 weeks was really fun. It was also nice that this project became my top priority task for that period, which came with the side benefit where I’d finish my 1-hour drum practice each day and think “cool, now whatever I do for the rest of the day is kind of a bonus”. ↩︎

  4. I highly recommend Transitions (my review) for anyone going through any kind of life transition, it’s been the closest thing to having a kind, supportive, and also wise figure by your side. It doesn’t provide direct guidance, per se, but for me it provided a calm voice reminding me that it’s OK to exist in uncertainty (the neutral zone) and in fact it’s kind of a unique and interesting experience. Don’t forget to enjoy the trip! ↩︎