How startup taught me to care

How does one end up in Sydney, looking back on the first 18 years of lived life only to find that they have gained nothing?

All startups begin with good intentions. 

Some suck, and not everyone is a Canva — we've got plenty of fraud in the Forbes 30 under 30. Working at a startup is an uncertainty in itself, and it raises lots of questions.

Now the question I've been asking myself: Is it worth it to work on something that might not even exist in two years? 

The question reared its head as I began to board a flight to Sydney: 

“What’s your per-son-a?”

“What does that even mean?”

“Like, student, venture capitalist, entrepreneur… other?”

Between friends it was a quick question played for laughs. The networking app whose existence had prompted our introspection vaguely reminded me of a dating app that said it was designed to be deleted, with its curved logo against a white background and its prompts to send likes and request coffee catch-ups.

I scrolled through my photos, looking for an appropriate profile picture. 

What was I doing in Sydney?

Ostensibly, I was attending a conference/festival/networking event. Sunrise, which wears many hats, is an annual venture capital funded ‘festival’ promoting “creativity, technology and ambition - a place where ideas collide”, according to the website. This year it was being hosted in Sydney Carriageworks, a reworked hall over a former railway. 

On the day, small coffee carts on wheels peddled free coffees to masses of entrepreneurial enthusiasts. Distinct pastel pink, blue and yellow banners and lanyards hung from the ceiling and attendees’ necks. 

What was I doing? 

I’d spent at least half a grand on this trip, hoping it would bring about some sense of stability to my career and uni life, which felt waning, but as I took in my surroundings I saw signs loosely taped to tables, a man walking into the bathroom wearing the tshirt of one company and walking out wearing the logo of another. 

In two days this would all be over. Will I have gained anything from it? 

Part 1: How winning is still losing.

How does one end up in Sydney, looking back on the first 18 years of lived life only to find that they have gained nothing? 

Very early on I was told that ticks are a good thing. They were a visible marker of a win, and if you got enough of those you’d be fast tracked into a degree which promised a white coat or collar, a cushy retirement fund, and a meaningful and happy life.

Based on my words and my looks at the time, you might assume that I was some academic Madonna. Let me disavow you of that impression now.

In reality, by the end of high school I’d accumulated a staggering number of tardies over two years of senior education and nearly as many absences (“sick”), took great liberties in my submission of sparse or empty drafts, painted my nails in cheap rebellion, frequently fell asleep in class and nearly skipped graduation. 

Part of this was laziness; maybe when you’re young you work out following rules gets you rewards, but by this age I’d taught myself that there was no principle in the matter; the end result could speak for itself. Who cared if I found my own writing dull and derivative and I’d forgotten about the entire thing by the time I’d submitted it? I’d gotten full marks.

However by the end, for all my rebellious posturing, I’d lost nothing of any significance. I may not have played by the rules, but I was still very much playing the game. I’d still ended up with an enviable ATAR (“the apparent triumph which involved no real effort"), mindlessly dragging my feet down some well-worn path.  

My carelessness allowed me to float through high school, but it also meant that I’d only pursued the wins that looked good on paper. 

In such a world, it was easy to ignore the deeper and truer fear; that to care about something, really, really want it, and pursue it is to sign up for the inevitable tragedy of loss and failure and possibly even humiliation at wanting so much in the first place. In such a scenario, I might’ve had to face the fact that I could have nothing to show after all that effort. Better to stay comfortable, and save yourself the sweat and desire and humanity. 

I realise that it may be gauche to rehash one's high school experience in such detail, but I tell you this story despite that as a warning that there is a path forward which is free from all loss and failure. 

I never failed, because I never cared, and frankly, nothing I did was worth anything. I was floating through my own life. 

Part two: How to know if something is worth it.

This is where startup comes back into the story, I hope you hadn’t thought I’d forgotten. 

The first time I met someone, “in startup,” I felt like I was staring into a lightbulb after being locked in a pitch black room. It also made me think:

“They sound stupid.” 

Here was this person who was willing to bet the next few years of their life on beating Amazon. I am only half joking. 

It is the unwavering nerve that makes the people in startup so bright and makes them buzz with an energy which is intoxicating. They may not win all the time, but every project felt like a matter of life or death, and it felt like they had at least nine lives. 

From an evolutionary standpoint, this felt right because for all its pastel colours and cheery disposition, startup is a land of death. All companies must die or re-invent themselves. Founders are like a revolving door, or fashion; in one moment, out the next. 

Their go-go-go energy, and the sincere belief that they can do anything, or at least attempt it surely taps into a childlike hope. One that many lose as the years pass. The more time I spent around them, the less I felt an email with a ridiculous ask was a matter to scoff about. I was frequently reminded of the benefits of rejection therapy.

And for the first time in my life I was terrified. I pored over every sentence of a pitch, spent hours locked in conference rooms talking about dogs, AI, fashion, the future of self-care. 

I had skin in the game, that’s how you know.  

Part 3: Losing

There was a moment at Sunrise that stuck with me. 

I was running around on the final day, frantically asking 30-somethings to film videos with me and tell me about their experience at the event. Most of the time, my face was burning and I was stuttering, well aware of the picture I created of myself; some barely legal student waving her phone around. 

I may have looked stupid but I wasn’t thinking about the future, or the what-ifs or my LinkedIn. I was just doing, and caring, and mostly being rejected and losing out. 

But the story mattered and so I pushed regardless. 

These smaller moments can also be viewed in the grander scheme of things. Yes, startups die, many of whom never fully live up to their promises. They couldn’t reconnect us with long lost friends, or cut our emissions or replace our therapists. 

But, I encourage you to chase what scares you, and inevitably when the time comes, to feel the losses; for the projects and the people, even as the companies implode into nothingness.  

Because to be prepared to lose and to act in the face of this, is to possibly give yourself everything; the ability to care fully, to pursue and work meaningfully. It is a matter of principle. 

So when I came back to Carriageworks the day of my flight, the venue was empty. Gone were the crowds, and the banners and the coffee carts. And it was just as beautiful as the first day. 

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An afterword

I hope that this piece, which has gone through many painstaking iterations, is a testament to the principle of loss, and of caring. When I first began writing, I felt very detached from my own ideas, probably because I only half believed in them and they were half-baked, and there was a part of me that was tempted to push out a piece which may have been technically more precise but which I didn’t particularly care for just to say that I did it. 

But when I eventually landed on the final thesis, I felt a twist in my stomach; I was scared. And that is the million dollar moment, when you realise that you have something worth hurting over, that the thought of it going awry would really suck, that is how you know you care, and that you may just have something very special in your hands. I am very blessed to be able to feel that.

I am also very lucky and grateful to Rodger Liang, who has helped me tirelessly and patiently through many evolving theses and who has had to deal with my amateur everything. I could not have written this without his help, thank you Rodger.