There is nothing forgiving about my mood.

Anger, when the sadness leaves, emptiness, when the anger leaves.

Inspiration comes in short bursts and it’s gone before I can give it a moment’s pause.

The cold cuts through my patched and safety pinned jacket, the rain smears my makeup and I am aware of a low, buzzing fear that my backpack will leak and ruin the shitty, sticker covered MacBook that is my sole source of company.

There is nothing forgiving about today. The grey is everywhere. It sits as a mute backdrop to the tyranny of the casino construction site and the grind of trucks and the downcast, damp people ducking past my camera every time I pause to take a snap.

Winter is a bad time to think about the cold.

The cold manifests in the peaks and valleys and every foreboding thought, and each desperate impulse.

When you think about the cold in the winter, you open the...

The unique behavioural artefact of the constantly connected world is our continual repurposing and recycling of its own culture into effigies and totems further and further removed from their original meaning. We no longer consume scenes, fiction, music - even current affairs and global events - without assigning them personal meaning, interpreting our lives and experiences through them and using them to express emotions, desires and ideas. We’re so connected to images, stories and ideas that we either cannot express ourselves without them, or see no need to.

I am observing this without judgement. I am not observing it without prejudice. It’s a language of living pop cultural semiotics that I speak naturally, and listen for naturally and increasingly it’s the language in which I think. It goes beyond watching a piece of art, or observing shaky iPhone footage of a massacre and noting...

Photoshoot by my dear friend Kayla

I think there is a paranoia around cohesion that can be incredibly debilitating, preventing you from making things, preventing you from enjoying things, because you fear that they don’t work with who you are. Or they don’t work with who people think you to be.

I used to know a young man who worked in investment, who desperately wanted to write books, write short stories. He was good. His writing was invigorating. And year by year, he wrote less and less. He’d tell me that he was worried about how the folks he worked with would perceive him, if they knew about this side that didn’t gel with the numbers and the money, that didn’t blend in with the business and the grinding, turning gears of the bank.

Sometimes I wonder how many people like him there are out there. Caught between wanting to express themselves creatively, and being bound by the...

Streetwear shopping on the edge of Chinatown

A hidden costume giveaway at a back alley theatre

I think I was asleep for too long. I spent too many years in a rhythm and a routine of comfort and similarity, and I played myself into the grooves of my own life. It felt as peaceful, as it felt nourishing, as it eventually felt anaesthetising.

At the time I was planning a wedding, and a life, with someone I loved dearly. And in our hurry to avoid facing the scarier parts of living, facing ourselves, facing our fears, facing trauma, facing the future, we relied on each other to create a deceptive numbness.

In the years since those days, I have lost so much of myself, and rediscovered so much more. My patterns are broken now. My life feels almost untethered and unhinged, in ways that can be frightening, and in ways that can be exciting. When I ask myself the question, “what if?” the...

I woke up early this morning, and took a long pause.
I literally spent an hour lying in bed and feeling thankful that I live a life in which I can do that.

It was dark out, and without my phone, I watched the light spread across Sydney and I put on a jazz record and I tried to breathe, and relax. When I got to the city early before hitting our startup’s HQ for the day, I. sat in a warm cafe, by the fire, and I drank hot black coffee and read a book that had nothing to do with tech, with startups or - to be honest - anything except dragons and wizards.

I got a coffee and a vegan triple chocolate cookie to go and I walked down to Miller’s Point in the cold to start my day. I’m writing some press releases, and I’m working on some comms messaging pieces for our startup and a couple friends.

This is the kind of morning I love. It’s the kind of morning I live for. It’s the kind of...

One of the oldest jokes in tech and startups is that people come up with a million dollar idea first, and then dream up a story about why they give a shit second. There is a certain contrivance about the eureka moments, largely because a good number of them are complete bullshit.

I am not one for that kind of false inspiration, I cannot and will not respect anyone who succumbs to it in search of a classic startup story they can pitch. I don’t believe in hiding my intentions, and I don’t believe in hiding my motivations. I believe in honesty above all else, even when that honesty may be prohibitive.

I want to hear honest answers to this question.
Why do you make things? Why do you do what you do?

If you’re spending your time and your life building a tech company, what is the real reason? If you’re raising a fund, why? If you’ve given it all up and you’re living outside the boundaries...

People often like to talk about their friends as networks. Like they’re a beautifully and purposefully designed web, created to boost them and help them to level up.

I’ve never thought about the people I know like that. I don’t meet people to build a network with them, I don’t talk to people to get something from them, I don’t interact because I have an agenda. I just have a conversation, and if I like that conversation I make time to do it again.

There’s nothing strategic about it.

I like to think that if you’re friends with me today, it’s because of that.

I saw some asshole talking about how he built a network worth $50,000,000 in six months, and all I could think about was how little I wanted to know him as a person.

I tweeted this the other day…

Some of my friends sell software,
Some of my friends sell nudes

— Joan Westenberg 🌈 (@Jonwestenberg) May 22, 2019

It was partly...

The physical and medical aspects of transition always scared me. There are so many hurdles that you face as a transgender person, trying to gain access to gender affirming medication and health care.

I began my journey back in January, prepared for it to be long, hard and draining. Along the way, there were a few surprises that I was certainly not expecting. I was diagnosed with a rare blood disorder called Factor V.

The disorder threw so much of the medical transition into doubt. Factor V is a genetic disorder that leads to a higher risk of blood clotting, and when combined with a course of blockers and oestrogen (what we call HRT - Hormone Replacement Therapy) it was potentially quite dangerous.

For the past few months, I’ve been a loop of blood tests, haematologists, specialists, endocrinologists and - let’s be real - a series of bars and a series of happy hours that were often...

I spent years on Medium, building up a following, using every trick in the book, every content hack I could find. I spent years building up an audience of 125,000 followers, with millions of monthly views.

And for the most part, it felt empty. I knew the person I had become, in order to gain that level of exposure. I had bought into my idea of what a tech or startup “influencer” should be like. I wanted to be a Tim Ferris. A Gary Vaynerchuk. That kind of confident hustle porn was my ultimate end goal.

The changes I had been going through as I came out as transgender and pursued my real self for the first time threw all of that into such stark contrast. It was so far from who I actually was.

I wasn’t some ultra-confident tech bro.

I was a scared person, full of doubt and anxiety, struggling through an intensely dark and disturbing period of my life where nothing was certain.

I...