One Year of Iterating

My thoughts after publishing a weekly newsletter for 52 straight weeks

Chris Jennings
5 min readApr 2, 2022
Photo by Behnam Norouzi on Unsplash

Hello Medium Friends!

This post was originally featured recently in my newsletter called Iterate. If you like my writing on Medium and want to get regular updates in your inbox, please subscribe here:

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It’s hard to believe that I’ve been sending out a newsletter each week for a whole year. 52 issues of Iterate are officially in the books!

There were plenty of weeks where it was a struggle. Some weeks I was working up until the last minute to make sure it went out on a Tuesday morning as planned. Some stories were better than others, but I’m proud of myself for committing to the project and never missing a week.

In honor of the milestone, I thought it was worth breaking out of the typical weekly format to give some insights into what I’ve learned and what I plan to do with this platform moving forward.

The Initial Concept

I didn’t have big expectations for this project when it started. That’s probably why I chose a name like “Iterate”. It gives me some leeway to shift topics and adjust the format as needed without being too tied down. I think that’s probably also why I was…

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Chris Jennings

I write about the intersection of technology, productivity, and mindfulness. See more of my work at iterate.substack.com