Midweek Nudge #38

“An optimist understands that life can be a bumpy road, but at least it is leading somewhere.”

— Harvey Mackay

Hi there!

Here’s your gentle nudge to make your week more interesting, thoughtful and productive. You can always talk to me more about these ideas by replying to this email.

You Know What? Optimism Is Cool!

I’ve been a pessimist/realist for years. I chose the term that made me sound cooler in the context of any conversation. These were, of course, mostly with people who claimed to be optimists. I’ve realised both people in those conversations were stupid. I was the stupider one.

Growing up, I had a lot to look forward to, but everything I thought of was a contingency plan for if things go wrong. In fact, up until last year, my default mode of thinking began from “if this happens” or “just in case”. Now, thinking like that has its benefits; I was insanely prepared for most days. I had a solution for problems, all problems I could think of, even the ones that were so improbable, they were almost impossible.

No, I didn’t think of what I’d do if a meteor crashed in front of me, smartass. Clever retort, though. It’s a common one. You see, this is what I’m talking about. The way I grew up, the things I saw, the way I carried myself put me on this feedback loop of predictive living. Every second of my existence has, until now, been about figuring out what happens next.

I’ve realised the error in my ways, however. I think before I divulge into that, I’ll tell you how I defined optimism. For me, optimism was the generic and naive belief that things would be okay when all I could see around were signs of them not being just that. I’ve changed how I define it now.

An optimist believes things will be alright. It doesn’t stop there. An optimist believes things will turn out fine despite everything they see. It doesn’t stop there either. An optimist believes things will be absolutely fantastic despite everything around them because they’re going to work for it and wait patiently.

All things considered, everyone is waiting for something. It could be a partner, a job, a vacation in the Bahamas, or just a pre-COVID, all-out Friday night. The thing is, and this is the kicker if you’re going to be actively waiting for something, why not make it easier for yourself?

To Read: Range by David Epstein


Have I finished it yet? No. Do I recommend this book? Absolutely. The one thing I’ve realised since COVID happened and with the stories I heard and the things that happened in my own life was this: specialists are great at short-term success and survival, but in the age of information, where half the jobs that you know today didn’t exist when you were a kid, it’s easier living like a generalist. I don’t say you have to be either. It’s up to you which path you choose. However, this book makes a good case that maybe being the jack of all, the disinterested loser, the quitter, isn’t as bad as most narratives make it seem.

What’s On My Mind?

 Effortlessness, in anything, is an almost sure-shot result of continual, consistent effort for more years than the Instagram account asking you to let it flow and then throwing a $25 ebook at you has existed.

Quick Update on Nudge › How 

I took a deep dive into philosophy and contemporary existence last week and wrote about how one of Zeno’s Paradoxes (refuted ages ago) is actually a good recipe for learning to be okay with striving in life. If you’re not familiar with the paradox or if you want some perspective on why the fabled pursuit of happiness won’t end, I recommend at least skimming through it. There’s a neat diagram in there as well. I made it.

I hope this added some value to your week. Stay safe, stay inspired, and I’ll talk to you next week.


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