I didn't want to be an astronaut as a kid

· Around 6 minutes

For those who read my blog, you’ll know that one of the long running arcs is documenting my thoughts as I enter each new job.

Day Xero was initially just a standalone post I slapped together as I departed for my first day as a member of the Xero graduate program1. It was since joined by Day One (Mercedes-Benz) and Day Two (Vend2) and I’m sure in time there will inevitably be a few more entries but for now, I’m pretty happy where I am.

Initially, I didn’t think too much about where I wanted to eventually end up nor did I ever actually expect to end up here in the first place. Back when I worked my shitty retail jobs, I was convinced that I had “missed the boat”3 so I never had any solid ambitions.

That brings us to the title of this post. I remembered about a year or so back that when I was younger, I had this dumb idea that I wanted to be a “skateboarding CEO”. I’m sure I took it quite literally when I was younger but I think I what I actually found cool was the idea of constrast. It’s fun to break some expectations (and rules!) in a respectful way and as a kid, I was probably more interested in the idea of “being a unprofessional professional”.

These days, I don’t focus so much on the CEO part4 as I do on the contrast bit. For anyone who follows me on social media, you’ll have noticed my recent “obsession” with Kumamon, the loveable Japanese bear who represents the Kumatoto region.

Now, I do actually enjoy watching various bits of content by Kumamon after recently rediscovering him. I’ve actually found the fact that such ridiculous content can continue to exist, even in the midst of the confusing times we live in. Nothing gets rid of stress like popping open a video of a goofy bear falling over or whatever antics he’s up to this week but that’s besides the point.

The other purpose of my silly “obsession” is that it acts as a type of contrast I alluded to earlier. Growing up, I always believed that to be successful meant being super serious and dedicated to a fault. You always see hackers and so on coding away into the wee hours of the night in movie and such. Well, this is my little contribution towards dispelling the idea5 that being or doing silly things is at odds with being capable. You can be both at the same time.

It’s not just Kumamon mind you. There are other things like some of my favourite shirts and what not but they all basically represent the same idea in some form or another. I also just find it funny, in an absurd sense, seeing myself in a goofy shirt while I default to RBF.

While I can’t claim that it does or doesn’t have any effect, I also like to think that if anyone finds anything I do worth looking up to6, that it’s somewhat comforting to know that you don’t have to be a super 10x hardcore asshole to accomplish things.

Now if I still took the “skateboarding CEO” idea literally, I would be (and was!) quite disappointed because it would be years and years until I accomplish it but by looking at it from a different angle, I realised that I already kinda made it there. At a smaller scale to be sure, but once you come to terms with the idea that bigger isn’t always better, it can be pretty comforting to have smaller, more achievable ambitions.

Anyway, that’s probably enough of that for now. I’ve only really mentioned the above to one person I can think of but I figure it’d be handy to write it out so I can refer to it again in future.

Perhaps it’ll change over time and I’ll believe in the idea of being a 20xer instead but either way, being able to review your trajectory through writing is a pretty neat idea and while I can’t really enjoy it so much, I hope someone down the line can enjoy seeing my years of progress condensed into a handful of posts and possibly get some use out of it.


  1. A bit of a misnomer on my part since I never went to university. Instead I went near insane from 3 years of retail before attending Enspiral Dev Academy as a last ditch effort before giving up. That was complimented by years of being a hobbyist prior and a couple more years of doing side projects and being rejected from jobs before I finally got my entrance into the industry.

  2. Technically I work for Lightspeed but I work on Vend. The product is referred to as Vend by Lightspeed but eventually we’ll just be part of Lightspeed. I don’t know for a fact that has been explicitly mentioned but it’s hardly a secret if you look at the trajectory on the public website.

  3. I was actually rejected from a university computer science course for not having enough math credits. Probably because I found Statistics boring and would skip class to go fiddle with HTML in the school library instead. Nowadays I have my rejection letter (aka “diploma”) framed on my desk at work.

  4. Large companies, especially anything VC funded, are overrated. Keeping it manageable with little to no debt is where it’s at if you ask me. Being propped up by large amounts of outside funding and becoming “planet scale” is just asking for a slow death in my book. Even worse is the idea of just bailing out at the IPO stage and leaving all of your employees holding the bag with a company that gets put into maintenance mode.

  5. Which I myself held in the past to a solid extent!

  6. To date, I’ve gotten two emails of thanks which is two more than I ever expected to get from this website. I also expect that old posts may get dug up in future without my knowledge at all which I look forward to. If not, that’s perfectly fine because with my goldfish memory, I can enjoy my old posts. I once re-read deepfakes and thought “Damn, I never knew any of this.”. Of course, I did know it at some point but entirely forgot it all…