Jay Shirley

Striving to be a man of gallantry and taste

August Retrospective

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People undertake challenges all the time. Sometimes they give things up and other times, like me through August, try to weave new habits into their daily routines. This is critical to me, as I enjoy to deliberately question the way I am spending my life.

A lot of this thinking started when I read Flow. It was truly a mind-opening experience for me. It offered conclusive proof that we continue activities we found enjoyable once, but only stay with them because of habit. Our enjoyment stops, but we continue!

I want to be constantly evaluate what I do. This has consistently allowed me to discover new things about myself and enjoy how I spend my time. It’s very naive to think I know myself well enough to know all my interests (or weaknesses). I also don’t believe that a single day, or even a week, trying something can be truly representative. It’s a base level of skill, and without competency I don’t feel I can judge. It struck me that a month seems perfectly reasonable to build competency.

In July, I wanted to test my ability to publicize a product I built and do it over a holiday weekend. I expected that I could build an app in 3 days, but also launch. This meant coming up with a marketing plan, verification and a plan to continue running and promoting the product. The latter are things I’ve consistently been bad at, and while I got better I’m still in the “bad” category.

My challenge for August was a little easier, but a lot longer. It was a marathon of writing and publishing, something I also struggle with.

Publishing Every Day: Victory!

I have a very solid writing habit. I however struggle to publish. I write, re-write, edit, hide it in the drafts and move on. What I publish doesn’t even correspond to quality; I often times publish entries I don’t find particularly good while I often rework those I like but never release.

I needed to remind myself that this is a blog, it’s informal and it’s a place for me to start conversations. It doesn’t have to be perfect.

I figured 31 days of very unperfect writing would help build that habit. And it absolutely did. I won’t publish every day, but I feel much better about quickly forming a post throughout the day and writing it in a way that I can get it out. I also learned it’s ok to put stuff out that still feels fuzzy or off, because it’s also ok to take something I wrote a while ago and re-write it.

A new challenge

A very large part of this effort is identifying weaknesses and exploring them. I’m not expected to solve them but simply to better understand them.

I’m a firm believer that the best way to explore a weakness is by coupling it with a strength. Similar to the way that tiny habits can build up, I want to connect a challenge to an existing behavior that I enjoy.

This month I finished up the editing of a video where I discussed Premortems. I had a lot of fun writing the script, reworking it, filming with my wife. The hardest part was just like publishing anything I write. Putting something that I find interesting out into the world is massively uncomfortable.

I have a great backlog of notes, highlights and thoughts on a series of books, so my challenge‚Ä® for September is to produce 4 videos. Rather than a book review, I want to record the take-aways from each book and also how it relates to others.

This one will be hard and potentially the most time consuming because the video editing process is so unfamiliar. However, I think it will be the most fun to date (out of 2, not setting that bar high).

Thanks for being on my August Challenge with me, and I look forward to continue writing here with greater frequency.

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