A Transformational Gap Year
Reading Time: 6 minutes
I’ve been back at school for nearly a month now, and frankly, I’ve barely had time to breathe, let alone journal, let alone write for my blog. But now that I’ve gotten and recovered from the freshman flu, and that life has calmed down after club ‘comps’ (applications to get into clubs here), I figured I’d get back to hobbies that I enjoy intrinsically. Writing out thoughts has to be the best debrief known to man, or at least, known to me.
The past year between high school and college has been absolutely transformational, so I thought I’d write up a brief summary of how I went about spending my time. In a nutshell, out of 10 months away from school, I spent 3 months taking time off in Sydney (Dec, Jan, Feb), 3 months interning (Mar, May, Jun), and 4 months travelling (Nov, Apr, Jul, Aug). I travelled to 12 countries, read 32 books, listened to hundreds of podcasts, met hundreds of people on call or over coffee, and worked on a bunch of side projects. I never cared much for arbitrary rules.
When we are in our most productive states, we tend to not notice a lot of things surrounding purpose, identity, and the subtleties of the world. And in a gap year, you take a step back, have time to yourself to think, and notice. You realise the possibilities that are right in front of you which you’d usually miss when you’re focused on conventional work. Taking time off gives you perspective, and in hindsight, this was one of the most fruitful outcomes I gained from my time off.
In this article I want to share my decision making process when it came to taking a gap year, and perhaps inspire those reading to do the same. It’s never too late or too early to be taking an extended period of time off, and I know I learnt an immense number of things about myself and the world around me.
My Story
Chapter 1: What is going on?
When I graduated high school literally on this very day last year (Sep 21st; when I started writing this), I knew that I had a dream to study overseas in the US, but school only started in August the year after. So, I had around 10 months to somehow pass after my high school final exams had finished. Aussie uni started in February, decisions for US colleges came out in December (early round, for one school) and in April (all the others), and in August I would hopefully be making the 20 hour flight over to the US for college.
The second that final exams finished, I was free. A few friends and I somewhat spontaneously decided to go on a trip to Korea and Japan - note that I said trip, not holiday. We loved it - the four of us roaming around East Asia, free of constraints and liberated for the first time. My personal favourite was visiting the Korean DMZ and understanding the gravity of actually looking inside North Korea. Like, damn - that’s North Korea. This was my first international trip without family by my side, and I absolutely loved it.
The rest of November and December were uneventful - I spent the bulk of my time working on college applications and trying to ‘plan out’ my time for next year. I finally organised my life onto Notion, and made a list of things, titled “What I’ve always wanted to do” - as the namesake suggests, these were things that I’ve always wanted to do, but couldn’t find time for because of high school. The list featured all sorts of things, from ‘Internships’ to ‘Personal Brand’ to ‘Physical’ to ‘Reading’ to ‘Life Skills’. The list served as a great landmark for progress down the line - every month or so, I would take a ‘Life in Review’ audit and refer back to my list. I even use it as a reference now, a year later to track how my intentionality has changed. In retrospect, I realise I was able to make progress on all of these categories, many of which I still have the rest of my life to develop.
On the experience/internship/brand front, this was an assorted bag of researching potential opportunities, sending out cold outreach emails (perhaps around 50-60), or setting up coffees + warm introductions with people in the startup space - who, I believe, value ambition, curiosity, and hunger for experience over many traditional qualifications. If you play your cards right, meet the right people, exhibit this burning intrinsic desire to work on interesting work, and aren’t afraid to take action, you’re bound to find great work. I was insanely lucky to have had a few incredibly generous mentors who took me under their wing, assisting me with guidance and introductions along the way.
However, come December 16th, I’m devastated by my Stanford rejection. I had all my mates on a Zoom call with me, and we were all hyped up, followed by this insane fall from grace. My idealistic mind had high hopes for myself and life decided to humble me, which was well needed. This fuelled a fire in me for the next week, as I worked on my college applications essays, mostly for regular decision. I wrote essays for a TON of schools and probably burnt out towards the end, eventually taking a well-needed break for Christmas before submitting applications at the tail end of the year.
At the turn of the New Year, after a bit of the aforementioned hustle in December, I had planned to intern in venture capital in Sydney and private equity in Dallas, spanning February/March (VC), May/June (PE), and with April for travel in the US (visiting colleges) and July/August for some solo travel before starting school in the States.
By the time February rolled around, perhaps with a touch of self-confidence, I knew inside that I probably wasn’t going to go to university in Australia first, because of the inherent opportunity cost, considering my planned internships. Worst case, if I didn’t get into a top US college, I would just start university either a semester or a year later.
Chapter 2: Working in Sydney
In the first week of January, I had a micro ‘crisis’ because I had nothing ‘planned’ for the next 3-4 weeks ahead. I had a chat with a consultant friend of mine at a mutual’s birthday party, and he advised me to treat this time as a bridging period - because a few weeks isn’t really going to make a huge difference to the trajectory of one’s life. I think my mind just wanted to be ‘working’ towards something.
So, I decided to work on some less structured things - I started writing some thoughts on LinkedIn (most of which I cringe at now), which led to more calls with interesting people who reached out to me (as I continued cold messaging interesting people), and most importantly, fishing with my mates more - we also went on a hike or two, which were amazing. I also formed a ‘Junto’ accountability group with some friends from Next Chapter, and we still meet monthly to check in on each other’s ambitions and progress. I was also lucky enough to watch the Australian Open with two other friends, and have a bit of a family holiday around this time in Aus as well.
Towards the end of the month, I learnt of two things with the internships I had planned - first, the VC firm said they couldn’t find scope for a gig that year, and the PE firm said issues might pop up with my visa status if I were to work in the US. It was the end of January, a third of my gap year had passed, and the remaining two thirds was completely upended. I had a bit of an existential crisis over the next few days, until I realised (finally) that work was not my life, and I had the rest of my life to work. I’d never really have this time again, so I had to remember what was truly important to me. I also had a coffee with a VC partner who told me that venture was probably not the best field to be exploring at the moment - venture is a sector that requires both a broad intellectual base alongside practical startup experience, and is an incredibly hard gig to pull off without having deeply experienced what startup culture was like.
It was only at the end of February when I realised that even though I hadn’t been working towards something tangible that I could necessarily write on my resume, I had grown immensely as a person. Sometimes, progress is invisible until you look back and are actually conscious of what you’ve done. I had been meditating and experimenting with mild biohacking for a bit, learnt how to cook, written quite a bit on my blog/LinkedIn (which led to a ton of calls and meeting new friends), finally got my drivers’ license, learnt to DJ (poorly), and was reading and watching movies a lot more. Funnily enough, at the bottom of my monthly ‘Life in Review’ session, I realised I that as long as you don’t scroll or game, it is impossible to waste time or not make progress.
My writing online had netted me a lot of inbound, and around that time when I was searching for more opportunities, I realised I had 5-10 potential gigs in front of me. I decided to work in person for a couple days a week at Kindling, a tech media startup founded by the amazing Sachin and Adam. It was a role with incredibly high ownership and autonomy, and I had projects I had been working on alongside adhoc tasks, all of which were highly stimulating. Funnily enough, I realised that most of the work I was doing (ie writing memos on particular sectors/companies/founders, experimenting with GenAI tools to automate our research projects) was work I’d be doing in my spare time anyways. I wore many hats, and was exposed to the most interesting and powerful people in the world. I honestly think that our office conversations were as good, if not better than the work I was doing as well - their energy was absolutely infectious, and taught me what it means to do work that’s meaningful for your soul, and not for money or fame. It also helped that we had a sauna + ice bath in the back of the office, with some weights as well. I ended up working for Sachin and Adam through March, May, and June - and if I wasn’t in the US right now, I’d probably still be working with them.
Chapter 3: Travelling
Come end of March and after college decisions, I realised I’d be heading to the States for the next chapter of my life, and I prepared to head over for a month. The first week I spent at the ASES Conference at Stanford, spending time with founders and investors at mixers and panels - I loved it, but then the rest of my time in the US made me reconsider my ‘startup techbro’ identity. After that, I spent a week solo in SF - I explored the city, met with friends at Berkeley, went down to Mountain View and Menlo Park to visit other contacts, and tasted what the States was really like when solo. My family then flew over and we headed up the East Coast from Washington up to Boston, which was incredible.
When I got back from the States, I had another revelation about the world of startups. I realised that in order to achieve what I had previously aiming been for, I had to sacrifice a colossal amount - physically, mentally, emotionally, spiritually. And I was turned off by the culture of some of the people I had interacted with. I realised that there was no point in doing something for the sake of doing it (especially building), that there are so many ways to achieve one goal, and that ‘should’ is one of the most dangerous words in the English language. I had crafted this persona for myself, and I had told myself that I ‘should’ be doing this, or I ‘should’ be doing that, when in reality, there’s nothing that you really ‘have’ to do. We all have our own strengths, and it’s often wise to play to them, in your ‘Zone of Genius’.
In May and June back home in Sydney, I think I summarised my life in three words to friends: “What do I do nowadays? Well, I intern, fish, and lift.” I loved it, and my friends who knew me at the time knew how much time I sunk into those three things. I found peace by the water with my rods, some music, and the river. I think it’s safe to say I’ll be fishing for many decades to come.
After some deep contemplation, I was in China for three weeks visiting family, with the amazing opportunity to visit my roots. I was then backpacking solo in Europe for another three weeks, which may have been the most fulfilling period of my life. I could write entire essays about travelling to a particular countries, in fact, my last article was all about my travels, so I won’t regurgitate much. Travelling to a home country is immensely powerful for discovering who you are - I discovered causes for many of my current traits, behaviours, and worldview. And travelling to new countries helps you discard all preconceptions about yourself and the world by revealing a completely different world and way of life to you. If you have the means, I can’t recommend solo travelling enough - especially without many plans at all. I didn’t journal or write at all during this time, perhaps in an attempt to live in the moment more. I did jot down notes I thought were worth remembering, though.
I then returned to Sydney for a week to get my affairs in order, before flying out to Boston, where I’ve been for the past month (and will be for the next four years).
Closing Remarks
When I told this story to a friend of mine at Oxford, he titled my story aptly: “The Gap Year: Asian kid from Australia meets the World”. Now that I look back, nearly nothing in my gap year went to plan, but the values I kept in mind have always remained constant. “You can’t connect the dots looking forward - you can only connect them looking backward.”
If I could do it all again, I think I would have, on an absolute sense, learnt a bunch more and been much more intentional with my time. But as the Arabic word goes, ‘maktub’ - it is written. I took a ride with fate, blowin’ in the wind, and this is where it landed me, so I’m immensely grateful. I would’ve tried to have been more present and really prioritised who I spent my time around. I think I spent nearly every day of my year working alone, obviously building relationships with those who matter most (ie family, closer friends), but I realised very distinctly that I would be solo for the majority of my year (and my life - see ‘Life is Single Player’; with the caveat of close friends, family, a significant other of course), and I think I’m a lot more comfortable with myself as a result.
Now that school is starting again, I’m getting used to the mix of structured and unstructured time - I obviously prefer unstructured time. I’m getting back to pure intellectual stimulation as opposed to an applied variant of it, and I’m enjoying it thus far. I think the perspective I gained from my time off helps me to prioritise tasks much better with the perspective of what’s most important to me.
I wouldn’t recommend a gap year to everyone who reads this article. But chances are, if you want to break out of the high school bubble and see more of the world while taking a break from conventional academics, and you’re curious about the world, I can’t recommend it enough.
Yurui
