Reading and writing on my home porch in massachusetts

My First Two Years Writing

The journey to a place that has held me accountable — the internet

Michael Dempsey
3 min readAug 7, 2013

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Over the past two years I've gone from a naive NYU student to well…a probably still naive 22 going on 23 year old living in Manhattan. As I started my career in finance, I began to do something I've never done before on my own: write.

In college I had a moderately followed photography blog where I’d post pictures, small updates to accompany said pictures, and that’s about it. I never really used Facebook status updates, my twitter has always been mostly just fleeting thoughts, but in person I was known for being incredibly opinionated and long-winded. It was at this point where I realized I should start writing these thoughts out so that I could hold myself accountable, and have some record of my thought process as I inevitably grew.

This process started off with a privately hosted Wordpress-based blog about technology, finance, and economics called Two Letter Worlds that I launched in November of 2011. I started this during my last few weeks of college, and accelerated it once I began working at the hedge fund I’m at now. I started writing because I was bored, and most of all because I wasn't really happy with the lack of options for sites that focus on the obvious crossover between finance and technology.

About a year in with Two Letter Worlds, I thought the content was lacking. I had become burnt out trying to create worthy articles that didn't really have any value-add content on my end, just to keep the few readers I had happy, and to try to engage my non-tech friends in the wonderful world of technology. I realized that I hadn't really accomplished what I had set out to do with my writing. I wanted a place on the internet where I could call my home. A place that people could go to and read about what I like, what I think, and in general get a better understanding of me. With that in mind, I started a tumblr blog called MichaelDempsey.me. I dubbed it my internet trail, though it has grown to be much more than that. Since June 30th, 2012 I have almost 280 posts in just over a year on my personal blog versus 176 in just under two years on TLW. Though I’m not retiring TLW just yet, I’m not sure when I’ll reach a point where I feel like I can regularly add a perspective to those worlds that doesn't belong on my personal blog.

Even though I don’t feel like I've changed much in the past two years, I feel fortunate that I've been able to create a record of my interests, passions, thoughts, and general writing over this time. Looking back at previous posts at times is embarrassing, but I imagine this is similar to the feeling of that first time you looked into your Facebook timeline. You cringe, you smile, your face turns red, but you’re glad you have it all.

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Michael Dempsey

Want to live in a better future so investing in Frontier Technology @compoundvc. Learn more @ www.michaeldempsey.me