I turned 50 the other day. I wanted to write an essay about how much I miss my dad who died when he was my age and didn’t get to do many of the things he wanted to do with his life. When I sat down at the desk I realised the feelings I have on this topic are too big to translate and I am not ready. Still, a 50th seems like a big thing so I’ve written a piece that is on brand for someone having a milestone grown up moment.

This essay is a reflection on ‘doing’ because after half a century on the planet you can’t help wondering: what have I actually done? I know for a fact that I have been very busy. One indicator is that I feel knackered – profoundly knackered – there is no breathing technique, ice bath nor holiday that can get me back to feeling energised in the way I once was. Viewed positively, a person probably should feel like something has been taken out of them after doing a lot, and they should look a bit haggard even if the professional and lifestyle milieu requires you to somehow seem vital at least until you are 60… hence the goddamn ice baths.

Another indicator that I have been busy are my notebooks. I’ve kept almost every one since 2003 and they literally stack up as proof of life. Standout entries include decisions to talk talented friends into doing things for free because I had no money. There is also a page with my entry ticket to the Rialto Observation Deck in Melbourne in 2004. I went looking for rooftops to do a cinema and spent $12.50 of the $20 I had to my name on the ticket. But I spotted a building with the right kind of roof, found where it was back down on street level, and then literally knocked on the door and spoke to the owner. I talked him into my idea and turned a $12.50 ticket into a truly beautiful cinema.

There are darker pages too: a decision to call my partners and close a business we had started and loved called Paramount Recreation Club. The scariness of standing down staff during Covid and then having to pretend I wasn’t exhausted when the world ‘opened up’ again. Choosing to go to court because morals matter more than money. It’s all in the notebooks – a record of 21 years of ‘doing’ and if the quality of my handwriting correlates with my mental health I’d say much of this has happened pretty close to an edge of some sort.

What people choose to do and how they do it is the product of culture, timing and ability. I count myself fortunate that I started doing things at a time and in a place where the dominant narrative for twenty-somethings was; if you tried hard it would be worth it because you would create something valuable in a world that was generally getting better. That narrative is dead now and for the first time since a World War we are at least facing, if not living, a reality of mass downward mobility – even the people who try hard often end up worse off and it doesn’t feel like the world is generally improving. Come to think of it, our collective excitement about new stuff has dulled in general. We seem a lot less excited about yesterday’s Mac OS Tahoe 26.5.1 upgrade than we were about the first iPod, even though the OS can basically pretend to be us.

I don’t know what it feels like for a teenager right now, thinking that they’ll probably not lead a life as good as their parents. All I know is that I am very glad I didn’t have the mood of the times pushing against my youthful energy. Reflecting on what was going on (or not going on) in culture at the time I started doing things, makes me realise that even though I am now 50 and knackered I have been very lucky to be alive and doing in the first two decades of the 21st Century. This is why.

Ignorance as asset

I started doing things in 2005, before MySpace, so it wasn’t possible to tell if people liked what I was doing at scale. Neither could I be hurt by mean things people could say about my ‘doings’ from the distance of their computer (though once a guy who hated a publication I started came up to me and said: ‘That shirt makes you look like you don’t get out very often and you wank too much’). Being unaware of public perception can be an asset, especially in the nascent stages of doing something when your idea is full of flaws and problems, or when you are too young to have strong armour against the mean spirits of others.

Inspiration sinkholes

Having a patchy and expensive internet connection without a smart phone helped. I literally couldn’t lose myself in the inspirational circle-jerk of TED talks and Social Media. There were glimpses of that world, but never bingeing, and so the time I saved by not watching inspo-porn was committed to doing something with whatever inspiration I had at the time. I once worked out that Australians had spent at least $1.6 billion worth of time watching a guy beatbox at a TEDx event and even if I liked beatboxing (which I really don’t) that is a warped waste of potential packaged up as inspiration.

Real deals

Lastly, I have also been lucky to primarily be in Australia away from the cliches of the startup world. We funded Rooftop Cinema because we sold $1 million of sponsorship to brands who believed we could do it before we had done it. These brands were run by managers whom we knew and liked. That’s very different to borrowing $1 each from a million people who you don’t really know on Kickstarter. We never knew the idea of hockey stick growth or the term “fail fast and break things” and because we were a little bit scared and a big bit responsible to people who believed in us we made it work. We had to.

Nobody needs more lamenting about the good old days – certainly not from a 50 year old. What we need is a way of moving forward as a society that magically gives us reason to try and something more than pallid and flimsy hope for a better world. In this context, maybe the most important thing to pull from my observations on doing is that you can still create those same conditions now. You can still be blissfully ignorant but now you have to select being that way. You can balance time actually doing with time getting inspired. You can be responsible and not treat real doing like a frat boy game. Nothing really changes if you don’t want it to.