Wednesday, February 28, 2024

Writing (And More) That Was Useful to Me in 2023

Sitting at my computer recently, I looked back across my notes for 2023. I was following my annual review process, reviewing the goals I had set for myself last January and the notes accumulated since then. I had a good 2023, accomplishing many of the things I had set out for myself. Those accomplishments spanned changes to my job (new role), my writing, and how I take and organize my notes. 

Several resources helped me achieve those goals in 2023. These are the books, posts, videos, and tools that helped me change my world for the better. Maybe some of them will be useful to you.

Cover of the book "The Staff Engineer's Path" by Tanya Reilly. The lower half of the cover is looking up at the outline of a large support for a suspension bridge. Where the support should be is replaced with blue sky and leaves on a branch.
The Staff Engineer's Path by Tanya Reilly was one of the books particularly helpful to me in 2023. 


I have continually tried to define my own job since I stopped being a manager and transitioned into a staff engineer role. I have tried to keep the impact and influence I enjoyed as a manager while removing the parts of that role that drained me. Over this past year, as I worked to change my role and my reporting structure, I searched for resources to help me in this goal.

The role of staff engineer (a senior individual contributor) in software engineering is not well established. There are only two books on the topic, and both were useful to me. The first, Staff Engineer by Will Larson, discusses the idea that there is no one ideal staff engineer. Instead, staff engineers may excel in very different ways. For instance, one staff engineer may have broad impact across several teams, while another may go very deep in one technical domain. He introduces four staff engineer archetypes describing four of the more common paths to staff engineer excellence. The book provided me with the language to describe what I was doing and what I wanted to do.
The second book is The Staff Engineer’s Path by Tanya Reilly. Tanya is an active member of the staff engineering community, organizing events and answering questions from people like me. She wrote her book from the staff engineer’s perspective, offering maps for navigating and thinking about your role as a staff engineer. I found two of Tanya’s insights particularly relevant: reporting to the correct level and evaluating your job.
As a staff engineer, you face the potential challenge of reporting to a manager at the wrong level (too high or too low) in your organization. Tanya explores the issue and how to handle it. I started 2023 reporting to a first-line manager. I ended the year reporting to a manager of managers, with better access to the information, perspective, and discussions I need to do my job well.
The Staff Engineer’s Path also suggests a tool for evaluating your current job, extending this blog post. The idea is to grade yourself on a scale from 0-5 on five criteria. I made a spreadsheet to track my progress, so that I could make informed decisions rather than decisions based on short-term swings in mood and apparent job status. It helped me put bad days in perspective, and to better spot the improvements when they came.
It can be challenging to clearly explain what you do as a staff engineer, since staff engineering roles differ so much. I used the ideas in two blog posts by Cian Synnott to help me explain what I do. I started writing weekly snippets at work, so anyone interested can see what I am working on and thinking about. More importantly, I wrote my own job description, got buy-in from my management, and shared it internally. The process of writing my job description was a key step in changing my role at work.
Finally, I greatly appreciated the encouragement from Nine Lies About Work to lean into what I’m good at, so I can be great at it, as opposed to focusing on improving my non-strengths and being uniformly okay. This message aligned nicely with the message from Staff Engineer that there are many ways to be a great staff engineer. This book had a large enough impact on me that I wrote a dedicated blog post about it last year.

Information Organization

For over a decade I used Evernote to collect, store, and organize my notes. In 2023 I stopped using Evernote and switched to a new tool called Obsidian. Two factors prompted this change: the development of more advanced note-taking techniques and Evernote updates disrupting my note taking. This video by Jorge Arrango (since expanded into the book Duly Noted) opened my eyes to the new possibilities of developing relationships between notes and using those relationships to create something greater than the parts. I have long used note-taking to remember things. Actively creating something new from my notes is an exciting step forward for me. Based on the video, I tried out and subsequently completely migrated to Obsidian.
Obsidian is a powerful and extensible tool. Even with my technical background and note-taking experience, I was intimidated by all the features, options, and possibilities. There are several helpful guides. I found the videos and resources from Nicole van der Hoeven particularly useful. I have copied several techniques from her videos and employed the sample Obsidian vault available to her Patreon members. The vault made it easier to use her techniques.
Jorge’s video also introduced me to Readwise, which helps organize highlights from digital media such as Kindle books. It pulls all my highlights into one system and automatically imports them into my Obsidian vault. I am an avid reader. Now I can find and review key highlights from books effortlessly. I am getting much more out of my reading with Readwise.


I started 2023 intent on improving my writing. Writing my blog has been incredibly satisfying and I wanted to take it to the next level. Several people helped me in this effort (thank you Heather, Eoin, Cian, Alex). I also found two books particularly helpful to me, Bird by Bird and Storyworthy.
Bird by Bird by Anne Lamont is a classic guide on writing. While nominally created for writers of fiction, I found that its lessons apply easily to my writing: the importance of vulnerability, honesty, showing up every day, the “shitty first draft,” and finding supportive people to review your writing. Bird by Bird has changed how I think about writing. It is also (of course) delightful to read. This quote on writing every day has particularly stayed with me.

"Do it every day for a while,” my father kept saying. “Do it as you would do scales on the piano. Do it by prearrangement with yourself. Do it as a debt of honor. And make a commitment to finishing things." 

The second book, StoryWorthy by Matthew Dicks, isn't even about writing. It is about how to tell a story that resonates with your listener. I hope that my writing will resonate with you, my reader. I illustrate many of my blog posts with stories from my past to reinforce their point and to make the writing more engaging. This book is full of ways to mine your experiences for interesting stories—techniques that I have included in my writing. And, similar to Bird By Bird, it has changed the way I think about my writing.


Just as I hope my writing will resonate with you, my reader, I hope that some of these resources will resonate with you as well. Whether you are looking to advance your career as an individual contributor in tech, improve your ability to capture, organize, and make use of information, or have more impact through your writing, there is something here for you. These resources have helped me grow and learn in 2023. I hope that they may help you in 2024 and beyond. When they do, I would love to hear about your resulting victories.

Special thank you to Heather Beasley Doyle for her feedback on this post. Heather is a gifted writer and you should read some of her writing herehere, or here

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