High Stakes and High Odds

Daniel Platt
4 min readApr 27, 2021

I’ve never considered myself a good reader. I’ve always felt others were more serious about it, faster and more dedicated. I think comparison and inferiority run adjacent to a lot of creative pursuits. I remember even as a teenager feeling I’d wasted my life because I’d spent so much time reading young adult fiction when a close mate had been reading classics. I was sure I’d never catch up. I feel similar about writing but also with surfing and swimming, woodworking…. I’ve developed plenty of passions but in my version of events, none came easily to me and I’m sure I never started early enough. I still prefer hiding behind low-stakes language like ‘hobby’, ‘amateur’ and ‘side-hustle’. I feel some part of that is culturally common in Australia but maybe it’s common everywhere.

Growing up, my older brother Jono was always faster, stronger and smarter and I struggled to compete. He loved maths and sciences so I chose the humanities. He ran so I swam. Jono got a skateboard so I got rollerblades… It was more than that though, I took my queues from his weaknesses. I still think of him as different to me — more naturally gifted in some areas and more naturally impaired in others. I don’t remember anything coming as easily to me or struggling with anything as much as he did. Where I was balanced, he was more concentrated. He was a natural runner but in a pool he sank like a stone — he was hopeless. I liked the water and spent years in swimming squad as a kid but I never felt naturally gifted nor especially dedicated. I put a lot more work into it than running because running was Jono’s thing. I was gaming the family dynamic chasing easy wins. At squad though, there were plenty of kids more gifted and dedicated. That kind of bummed me out because I wasn’t trying to beat people at their own game, I was trying to rig it.

It was easy for me to excel beyond my brother in the pool — I float. But what happens when I’m trying to distinguish myself not just from Jono, or even my swimming squad but like, everyone. Unfortunately, there’s nothing out there someone isn’t already very good at. Trust me, I looked. I’d love to say I learned the lesson, grew gritty and determined and to not feel like an impostor, but that family of origin stuff can be tough to kick. Swimming wasn’t it, so don’t bother Googling my world records, I never went much past the Melbourne Jewish Interschool’s, which is indeed a very little pond.

At Uni, whether it was writing or film production or history I was always fine, I just wasn’t ever really good. There were always people who took themselves and their work more seriously and at twenty-something, I had an allergic reaction to those people. I also learned the more you specialise, the harder it is to game the system — to achieve an outsized return from your investment. Through a kind of distillation process, the people around you tend to grow fewer, more intense and exceptional the deeper you go. We’ve all had that experience of calling it when we realised we were the least serious person in the room, or on Strava. For most of us in most things, good enough is good enough — we satisfice (which is a very handy word) because there’s an opportunity cost to being exceptional and life demands we are quite good at lots of things.

In spite of my childhood and my biology, I find it helpful to remember most things are not inherently competitive. In business, it’s easy to compare your success with others but it rarely matters and it certainly makes you more likely to follow than lead. Innovative companies like original people are a lot less concerned with what others are doing. I’d love to say I’m like that, and I got here through being thoughtful and deliberate but like most things, I think I’m not especially competitive because I wasn’t a good competitor.

Fortunately, there are other more enduring forms of motivation, like creating value for others and meaning for myself. Rules are good too, like writing every Monday — you don’t even need motivation for a rule. Several years ago, I also started thinking about being bold. There’s a lot of good data around setting achievable targets and building momentum and there’s a lot of merit to low-stakes language. It’s probably my default. ‘Probably’ is low-stakes language. Very occasionally (also low-stakes language), I’ve pursued something I care deeply about when I wasn’t confident in the outcome; high-stakes and high-odds. You need both. That’s how I think about being bold and it seems like a good foil to all the bad habits I’ve just been telling you about.

I’d like to be bold more so I’m writing it down.

Originally published at https://danielplatt.substack.com. Click the link to subscribe.

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Daniel Platt

I’m a business owner and writing enthusiast. Writing helps me think deeply and work through the complexity of everyday life.