What’s behind it all?
Every year, just before the new year kicks off, I set aside a few days to drift between cafes and nature to reflect.
This time, I found myself sitting along the river near Rhodes with my Moleskine, just journaling for hours. I do this because I’ve always lived by that Socrates line:
"An unexamined life is not worth living"
To me, we can only make sense of our lives by connecting the dots backward and staying anchored to our core.
Usually, these sessions are a mix of structured reflection and freeform journaling. But this year, I decided to try something different - because why not? I uploaded my library of ~100 journaling prompts into my Gemini, and knowing what it knows about me, I asked it to generate the "ultimate end of year reflection"
And, it was surprisingly good, giving me sort of a clear past-present-future flow.
As I was working my way through the questions, one by one, until this one stopped me cold.
What’s something you’ve had a hard time being honest about this year, to yourself?
I froze. It’s hard to articulate how raw that felt.
Earlier in the day, I had been auditing my year, listing my “doings”. On paper, it was arguably the most significant year of my life:
I’d finished my dream internship at Bain & Company, travelled to Asia and Europe to represent UNSW in case competitions and eventually standing on a podium in Portugal.
And then there was the pool. For months, I’d been training, diving into cold water day in day out, hitting the weights, saying no to a lot of things, and pushing my body to the absolute limit, all for one goal. But at Australian Opens, the clock didn’t care about the effort, only to miss out on World Champs qualification by a mere fraction of a second. And it’s a specific kind of heartbreak to look up at the timer realising that months of “giving your all wasn’t enough” (a whole other learning for another day).
Then came NextGen Ventures. It was the first time I didn’t feel like an outlier. I’d found a tribe of people who were just as optimistic, obsessed with the future as I was, and for the first time, I didn’t feel like I had to justify my curiosity, and I knew then that this was the path I’d take, and I haven’t looked back at the corporate world since.
So I was staring at this list - a mix of wins and the raw stinging “almosts”.
But as I sat there by the river, that one question, made me pause and think so deeply, because it forced me to confront many of my default beliefs - the “truths” I’d been hiding from myself.
And the first that came to mind, was the confrontation of what’s driving me to do all the “doings” after all.
When I looked closer at that list, I saw that so much of my relentless pace was fuelled by a desperate need to stay ahead of my own fears:
the fear of being irrelevant,
the fear of stalling,
the fear that if I stopped achieving for even a second, my value would disappear,
the fear of death.
Honestly, It was a total truth bomb. It confronted the shadow side of all that drive. And it made me realise, that I was so obsessed with “doing” - with the next win, the next experience, the next 0.1 second and I lost touch with the why, the “being”.
I had to ask myself: When I strip away all the achievements and the doing, who am I?
Searching for an answer, I sat down today (Jan 1st) for a call with a friend I look up to, who’s super introspective, in touch with his core (and inevitably on a path to greatness), someone who has been a massive "expander" for me.
I started by jokingly sharing that - It was a weird day, and funny enough I was feeling the weight of the holidays, that "self time" that feels dangerously close to loneliness while most of your friends are back home overseas.
Then, I told him about the prompt. I told him that as I looked at my trajectory changing year, I realised I still didn't really fully clear on why I was doing it all.
He listened, then asked me a question that cut right through the noise:
“How well do you feel like you know who you are?”
I had to be honest with him, and myself: Apart from some of the core things (the adjectives that describes me, the values I aim to uphold, the life-story I’ve been telling people…) - I still don’t, and I realised a chunk of my deeper motivation was stemming from fear - and one layer deeper, at times I got lost with who was underneath all.
We talked about how exhausting it is to have our identity tied entirely to your output.
He shared his own struggle with "optimisation" - the trap of trying to squeeze value out of every waking second (fair enough, he’s building a first-of-its kind ecosystem in Australia, and a fund manager at the age of 23…).
It got to the point where sitting in a park for 2 hours felt like a "waste" in his brain has to fight against. And i realise, the higher the stakes of the external “doing”, the harder it becomes to just “be”.
And frankly, we and many more ambitious people were fighting the same impulse to justify our existence through our calendars.
But, In that conversation, the dots finally started to connect. We discussed the difference between intrinsic and extrinsic motivations and “doings”, and he pointed me toward The Imperfects podcast. It led me back to a core principle from Ben Crowe:
Start with "Who am I," then move to "What do I want to do" and never the other way around.
It was refreshing reminder that we need to understand ourselves on a deeper level first.
Because when we lead with the "What we want to do", our self worth becomes conditional. We start looking outward, craving for people’s recognition, and we lose our internal compass. The catch is that we can never truly control external outcomes - something I’ve definitely been forgetting (shame to say Meditations by Marcus Aurelius is one of my favourites, sorry stoicism) And even if we hit the goal, the fulfilment never arrives, because we’re still chasing an illusion of perfection, running away from that internal fear of being "not enough."
More than that, when we chase the illusion of perfection, we are ignoring the very human, imperfect core that actually made us who we are, uniquely, and which allow us to connect with others (another topic to be discussed).
Looking forward to 2026:
I know It will be one of the biggest years of my life. I have aspirations, clear goals, and dreams I’m hungry for. More importantly, I want to keep growing in every aspect: physically, mentally, emotionally and spiritually.
But, I cannot forget the inner work. And it has only just started. There is a lot of work to be done, but I’m optimistic.
And this essay is a simple reminder to myself to stay grounded amidst the noise.
ps. Currently I’m re-reading up the book that once helped me understand where my fears stem from, from a psychoanalytic / cognitive standpoint - Reinventing Your Life by Dr Jeffrey E Young - and let’s see how that goes.
David So
