Why: Q2 2023

I have owned mcwhittemore.com since early 2009. Looking at wayback machine, it appears I bought the domain while on the job hunt, to blog about my writing life as and present myself to the publishing industry. Reflecting back, this fits. My career ambition in 2009 was to get a job in the digital department at a book publisher. And by early 2011 I had interned at Overlook Press, freelanced as a ebook typesetter (its just html) and wrote a completely unedited :facepalm: "manifesto" on formatting poetry for the Kindle. But the dream never came together and overtime mcwhittemore.com became a subscription I renewed out of nostalgia. In 2015, I even let the registration lapse, bringing it back to share an on-again, off-again art project you can still find on this site.

In a way, May 2023 feels a lot like June 2009 for me. Squarely in my late thirties, I have this sense that I'm graduating from one phase of my career and that I need to figure out what the next one will be. That old management question, "where do you see yourself in five years", seems like the right question to be asking. So, what do I want to be doing in five years? If in 2009 I thought, "Matthew Chase Whittemore Must Work in Publishing", what do I think today?

What follows is my attempt at an answer. It's written as a set of goals because goal setting is the cornerstone of how I think about creating clarity. I'll admit I have some trepidation doing it this way. The fact is I'm still working out what I want to be when I grow up and writing them out like goals makes it seem like I'm confident. I'm not. But, this is pretty common I've found in goal setting. You work with the information you have. With the information I have, here are my goals.

Goals

Long Term Goal: Be a known resource for advice and thought leadership on processes to create value generating clarity for software teams.

Next Milestone: Get in the habit writing down and sharing out my thinking on processes to create clarity for software teams.

Specific actions:

Why do I want to become a known resource for advice and thought leadership on processes to create value generating clarity for software teams?

When I first became an Engineering Manager I wrote "clarity is motivating" on a piece of paper and tapped it above my monitor. Seven years later now, very aware of the thousands of things I got/get wrong, I'm shocked and amazed about how right those words were.

Creating clarity motivates people. It gets them out of a funk and heading in a direction. The question is, is it the right direction? Its easy, too easy, to just tell someone to do X. That's clear! It could also be wrong. This means creating clarity is a risky and powerful thing.

Creating clarity well is critical to running a good team or organization. I want to become a known resource for advice on how create value generating clarity for software teams because, if I get to this point, maybe I'll actually know how to do it myself. Right now I feel like I can see the potential of doing this well and I want to live into actually doing it well.

Why do I want to get in the habit writing down and sharing out my thinking on processes to create clarity for software teams?

I tend to have a lot of thoughts about what creates clarity for software teams. Right now those thoughts are mostly honed via dialog in leadership meetings and one on ones with folks at work, but to scale myself towards being a thought leader my thinking needs to be honed by the editing process of crafting prose. It then needs to be honed even more by being shared with people I respect and who will give candidate feedback that will help grow me. To do these things, I need to have the habit of writing and sharing. It's easy to write one night. It's hard to constantly write. By focusing on habit formation I hope is set myself up for a longer focus on this area and thus create more space for me to grow than I would simply by writing one or two posts on pressing work issues and then 'waiting' for the next 'pressing' issue to spur me on to write more.

Why a one high quality blog post a month minimum rather than a 2 or 4?

I tend to over estimate the amount I can get done. Someone recently noted to me that humans underestimate how long it takes the current task to get done also underestimate how much than can get done in five years. My hope is that by focusing on one, high quality, blog post I can focus on the craft of writing rather than simply banging something out on a Sunday afternoon in fear I won't be ready for next weeks post.