In my last post, dated a little over two months ago, I said I hoped that I would have some good news worth sending a newsletter about.
Well, the thing that I was hoping for did happen, and now I have my good news post, and a curious aversion to posting about it. Because even though I have proof, I’m still not quite convinced that it’s real.
So by way of explanation, a diversion.
In the year of our lord 2016, which was TEN GODDAMN YEARS AGO, WHAT THE HELL, I entered a competition sponsored by a little company called Microsoft. The competition’s webpage has long since succumbed to Internet Rot but the idea was to promote the then-new and now-deprecated Microsoft Surface Book by giving someone the equivalent of 12 months salary – pegged at $60,000, which was more than I was making at the time – to take a year off to pursue their dreams. The promotion boilerplate said:
To promote the new Microsoft Surface Book, the ‘Bring your Dream to the Surface’ campaign is a competition targeting Kiwis who harbour a secret creative passion but have not been able to make it a reality because of their nine to five job. Entrants are required to submit their creative ideas at winayear.co.nz and the best will be chosen by a panel of judges.
I tried very hard to Win A Year. Unfortunately, my pitch wasn’t very convincing. Essentially it was “if I win this I’ll try to become a full-time artist by keeping on with my birds in hats malarkey while also drawing and publishing a comic book.” I came up with all kinds of embarrassing supporting materials which I would post here – they still exist, I chanced across them on a random cloud drive or computer a few days ago – but are currently mislaid. That’s probably for the best; I winced hard when I spotted them. I can only imagine the Microsoft judges, when assessing my pitch, Googled Binged the average salary and mental health of cartoonists and wisely awarded the Year to a swimwear designer. I had a look for her stuff just now and her website seems to be defunct, which is a shame; she made great togs. Runner-up went to my colleague, who designed boutique watches. Happily, he is still going! If you’re in need of a stylish timepiece, consider a Draken.
Most embarrassingly, I hassled pretty much everyone I knew via social media into voting for me. This meant messaging people from high school, which isn’t something I plan on doing again. For a brief moment in time, I felt what it is like to be embroiled in a multi-level marketing scheme.
After I didn’t win, I tried to forget about the competition altogether. But it wouldn’t get out of my brain. Not just from the cringe that reared up every time I went to message someone on socials and realised the last time I contacted them was to say “please vote!” It was because it was a fundamentally neat idea. A year, all to yourself, to just cook.
The fact that it was almost exactly ten years ago now feels somehow auspicious.
Since I didn’t Win a Year, a lot has happened. I got some mental health and religious trauma stuff sorted out to my occasional satisfaction. I had four different jobs. My wife and I had two children. I wrote a fair bit but never enough, did a similar amount of art, and occasionally dipped into the boiling ocean of content creation only to burn out quickly when it turned out to be too much on top of everything else. We moved house several times, eventually buying our own place thanks to my constant but mostly inadvertent scaling of the corporate ladder. There was a problem with that, though.
I didn’t much like the ladder.
Perhaps this is putting it too mildly. Here’s a clip that would often pop into my head, unbidden, every time I found myself in another Zoom meeting that could have been an email, another email chain for a doomed project that should have remained a CEO’s stray thought, or any given interaction with LinkedIn or Microsoft Teams:
I realise admitting this publicly is burning my boats, but I cannot do a corporate marketing job any more. I mean that literally: more often than not, the jobs I used to do have been taken by AI. If you are unfortunate enough to have something like my old job, your duties now consist of sending your AI generated slide deck about the performance of your AI ads to the AI agent that monitors the CEO’s email so it can generate an AI reply for you so your AI can summarise it. Knowledge work has been bullshit jobs for a long time but the vultures of AI have stripped the last remaining shreds of meaning from the dessicated carcass. Every job ad I’ve seen for the last year or more requires you to swear fealty to AI; your job application (which will be graded by an AI, of course) will require you to talk about the ways you are “actively embracing AI”.1
I’m still grateful to those jobs for giving us the opportunity to buy a house and put food on the table and allow both my wife and I time with the kids. I made good friends in each workplace, too. But the sheer futility of knowledge work and the trauma of either leaving a job because it’s the only way to get a pay rise or falling off a redundancy cliff – because knowledge workers are ultimately all line items in a spreadsheet marked EXPENSES which some accountant is itching to delete so they can get promoted – eventually had that Agent Smith speech playing in my head on a constant loop. “I must get out of here. I must break free.” Sometimes I’d mutter those lines in the shower before kicking off another work day.
Being made redundant for the final time helped; I was at least no longer obliged to go along with corporate strategies that made no goddamn sense. That alone was almost worth the price of admission – but that price turned out to be very expensive. I was able to do just enough freelance work to keep my head above water, but it was mostly the same kind of tasks I’d done previously, only for less money and much less free time. Meanwhile, I watched as startup after startup got hosed with venture capital cash for putting together a word salad proposal that used “AI” like croutons.
It was very frustrating, and it kept bringing me back to Win A Year. If I could do that over again, I thought, I’d have a better pitch. It’d still be about art, but this time it’d be about how I could develop the art education product I’d wished existed when I was learning, and that no-one seems to have made yet. Believe me, I’ve looked.
And then one day, having recently sent a few job applications into the ether, and feeling like I should follow my own advice about doing difficult or scary things, I pitched my idea to an investor.
As a few bullet points in an email about a wildly different topic.
They wrote back. “Intriguing!”
They asked me to make a pitch deck, which is Startup for “a slideshow explaining your idea.” Sweating bullet points, I did that. I pitched the idea.
They asked me to pitch again. This is usually a good sign.
I redid my pitch deck according to some usefully pointed feedback and presented again.
They asked for me to make a business and marketing plan.
I wrote 3994 words, outlining a year’s worth of operations.
“Pitch again, please.”
I did.
They said yes.
That was a month or few ago now. Even after the “handshake yes,” I stayed very quiet; only my immediate family knew what I was working on. I didn’t want to say anything to anyone in case something fell through and I’d have to walk it all back. But – as of this time last week – the corporate and governance stuff is all buttoned up. The investment has been made, the shareholding is sorted out, and I am a director and the CEO of an art education company.2
At the risk of pointing out the obvious, this doesn’t mean that I get to spend a year playing videogames or painting an accurate replica of the Sistine Chapel on the roof of my garage.3 For one thing, I’m pretty sure the contracts I’ve signed allow the investors to claw back my organs if I goof off to the point of squandering their investment. With that said, my product, when I’m ready to show it, will need promotion, and that means I will be doing quite a lot of art and posting it to social media. Which is, if you remember this post from almost exactly one year ago, what I wanted to be doing anyway.
Well, I’ll have to do it now. Because it’s my job.
I’ll also have to write and post more too, which I will also have to do now, because that too is part of my actual job.
My studio’s all set up and today I put brush to canvas for the first time in a couple of months. Also somehow my job.
And all of the startup and marketing and miscellaneous corporate skills I spent a career building are not wasted. That’s an absurdly big deal to me. For years I’d felt like a fateful decision I’d made a little more than a decade ago – where I was offered both a dream job as a feature journalist and a marketing job up in Auckland within 24 hours – was one of those Sliding Doors situations and I’d made the wrong choice.
That thought haunted me for years.
Maybe I can put it to rest at last. I have a new job now, and it is making art and building a successful company by teaching as many people as possible how to make art too.
It’ll be a lot of work. There will be plenty of ups and downs. I’ll be drawing and painting and writing and making videos about all of it.
I hope you’ll come along for the ride with me.
Here I really have to thank the investors for, well, investing in my idea and placing trust in my ability to pull it off. Most of all I have to thank my wife. When I told her I had been made redundant (again) and that I had a few ideas that might keep us going, her response – rather than an entirely understandable “oh for f*ck’s sake, go get another job punching prompts immediately” – was to say “I have total faith in you.” And I have clung to that faith like a raft in a raging ocean. None of this pinch-me-I’m-dreaming stuff would be happening if it wasn’t for her. So thank you, Louise. I love you.
And thank you, as always, for reading.
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