Old Year, New You
How Systems and Tools Help You Become Yourself \\ Dec. 2024
Greetings, Elf-friends!
Welcome to the last newsletter of 2024.1
As the year comes to a close, we're wrapping up projects, plans, and presents, and the most important thing of all, preparing to spend time with those whom we love and enjoy.
And if the season calls for lots of travel and not-so-enjoyable companions, well, that's why there's wine and Netflix. But I hope such grit-toothed scenarios are few and far between.
I'm so looking forward to launching People Watching on Tuesday, January 14, 2025!! I've had the best time talking with amazing women about the meaning, purpose, and significance they've found in their lives, and especially about the influence that role models have had on their journeys. I can’t wait to share these women’s insights with you!
Today's issue offers a different take on the usual annual review. Sometimes annual reflections feel like an abstract exercise in figuring out "what stands out and what's next?" So I think and hope this provides a practical complement to that reflective process.
This is a long one, so your email provider may cut off part of the whole. Just click in the email to read in your browser or even the Substack app. Ready? Read on!
Writers love having written AND being read. Who else needs to read this today?
The Clutter, It Hurts
I hate clutter.
It drives me nuts when I see lots of things scattered across my desk, around the room. I can't concentrate if there's stuff piled behind me and it's not even in my line of sight.
It niggles at my braaain, like constantly picking at a hang-nail.
This carries over into the digital sphere.
If there's loose items floating around the archive, if I can't figure out where to store a file or record, if hierarchies and labels to find things later don’t make sense...well...
The open loops take over my psyche and make it difficult to sleep, because I Must Solve the Problem.
So when I tell you that today I feel rather victorious, as though I've climbed a mountain, I need you to understand that I've spent the last two weeks doing a deep dive into my digital tools, processes, and systems.
There's something so very satisfying about finding solutions that help navigate the chaos. It's a truly dynamic process of finding that sweet spot that allows for serendipity while also providing some structure to make sense of life and do what matters.
Software Ate the World
One of the frustrating things about any software (even really well-designed software) is that it represents an entire perspective on the world and The Way Things Work. This is, of course, the prerogative of all creators—to express their unique and singular view of life, the universe, and everything—but what makes it especially constricting in the realm of software is that it becomes the paradigm by which we ourselves understand and navigate the world.
Even when that's not actually how we understand and navigate the world.
Tara McMullin makes this observation in her essay "Seeing Software," when she observes that, in using software and defining operations, any given "feature or limitation is accepted as unchangeable. It's the humans that end up changing to accommodate it."2
One of the wonderful things about discovering and building in Notion is that I learned how my brain works, how to grasp the mechanics of tool operations, and how to design the steps that produce the results I want or need. In an age of proliferating SaaS options, it's a true benefit to have such knowledge, because it helps me discern "first principles" that operate no matter which tool I use.
Especially because software has become a ubiquitous feature of our lives, we need to understand how it accomplishes the outcomes it claims for itself, the perspectives it reflects, and the ways in which it shifts the balance of power in economic relationships.
Software had already insinuated itself into the way people thought so that they had a hard time thinking about what they wanted done or how they wanted it done outside the software paradigm. They were much more comfortable starting with one set of features and comparing it to another—in other words, evaluating software on its own terms. As a result, they subverted their work and business priorities to those feature sets. -Tara McMullin, "Seeing Software"
What's It Mean, Alfie?
So.
Why does any of this matter?
What difference do tools and processes and systems make?
There's a quote I read once (wish I could remember where!), that says, "I'm really a very different person, I just never get around to being that person."
This resonates for me, because if I keep saying I'm a writer and reader and thinker, but I'm not doing any of those particularly often or well, then...am I actually any of that?
As we wrap up 2024 and look toward 2025, it's a natural period of transition and reflection, a time to step back from the daily routines and chores to see what's accumulated over the last twelve months.
It's often the case that much of life feels chosen for us, and we frequently have projects or obligations that we cannot delegate. But it's also the case that how we frame even those "non-negotiables" can make a great deal of difference in the kind of life we live, the kind of character we form, and the kind of person we become.
In his book Who Are You, Really?: The Surprising Puzzle of Personality, Brian Little observes that
your life and your identity derive from more than just your inborn traits and your circumstances; they are borne of your aspirations and commitments, your dreams and your everyday doings. These defining activities are, in two words, your personal projects.3
How you understand your personal values and goals, even the skills, interests, and gifts you possess helps you move forward in each given day. Whether you believe life is a gift or a burden, it still asks that we get out of bed and do the next thing. And whether that next thing feels significant or meaningless says a great deal about what you understand the purpose of your life to be, and the future you imagine for yourself and others.
What you do affects who you are. This is because personal projects are all about the future—they point us forward, guiding us along routes that might be short and jerky or long and smooth.4
In order to complete any project, we need an infrastructure that helps us accomplish the steps necessary to move forward. And that infrastructure is comprised of
tools (digital and analog)
processes (repeated, regular steps done in sequence)
systems (a set of interconnected things that produce a pattern of behavior over time)
So how can tools, processes, and systems help us become ourselves?
Making a Mess of It
Creating More Clutter
As mentioned, I've just completed a deep dive into the digital "clutter" of my tools and processes. I kick-started this little project after coming across a blog by Beth McClelland, who recently wrote about ten lessons she learned about building systems. These three really stood out for me:
Systems need a goal personalized to you
The systems themselves should be personalized too
Systems change over time
I realized that I no longer had a clear, comprehensive, and comprehensible goal for what I wanted my tools, processes, and systems to help me accomplish.
What's more, I realized that Notion no longer serves as the one-stop shop that it used to (cue the gasps). In my internet travels recently, I read a comment on productivity tools and was reminded of something important: these tools should get out of our way. As fun as it can be to tinker and build in something like Notion, the whole point of these things is to make it possible to do the work. If we spend as much time maintaining the tool as we do executing the work, something has gone horribly awry.
And I find myself wanting simple, beautifully-made tools that do specific things really well.5
What I Learned About Myself
I realized that I truly want to draw from research and notes to write regularly, effectively explore, connect, and generate NEW IDEAS, and regularly publish high-quality writing and podcast episodes. I also want to generate regular discovery calls and create leads for future workshops.
I don’t want to spend a lot of time setting up, designing, or tweaking tools. And I honed in on the source of the friction-frustration that I keep feeling: I’m doing everything manually to move from reading, to saving, to highlight/commenting, to transferring to a different context, etc. Because everything about my reading, highlighting/commenting, exploring process is so labor-intensive, I don’t want to do it regularly, and I don’t want to find the time to do it.
Also, I started thinking more specifically about privacy and communication, in that I’d like to get away from Google products, especially email.6 I also started thinking about how much I have that’s accessible via cloud storage, and questioning if I wanted to return to local/hard drive storage, especially in light of the Crowdstrike IT outages earlier this year. While I personally experienced minimal disruption this time, I fully expect that we'll start to see more such outages, disruptions, and failures over the coming years. Ergo, I'd like to reduce some of my dependence on cloud-based tools where possible.7
Creating Solutions
I've narrowed down the tools that I use for very specific purposes, and I've clarified how and when I'm going to use them. You'll see that Notion is the very end location for some things, and no longer the first place for all the things. It's quite an evolution for me!
Put Some Swing In It
If you hang out with me for anything length of time, you’ll probably hear me say at some point, “It’s like the great Duke Ellington says, “It don’t mean a thing, if it ain’t got that swing.” What can you do with these ideas?
As you begin to use your tools regularly, you'll develop a process of using Tool A at X time for N purpose, Tool B at Y time for N+ purpose, and Tool C at Z time for N- purpose. Over time, you'll develop habits of reaching for each tool and executing the process without conscious choice, and before you know, you have a system that produces consistent, periodic results.
But here's the thing: you're already doing all of this.
You just may not have thought about it or chosen it. And if you're looking to pursue different goals or change behaviors, you need to articulate the what, how, when, where, and why of your tools, processes, and systems. Additionally, articulating what you're currently doing helps you identify gaps in your processes, subconscious frustrations you keep feeling, and roadblocks or bottlenecks in your workflow.
So here's some ideas for interviewing yourself and your tools to complement your annual review and planning (if you have one!), and if you don't, maybe this can serve as the start of a regular reflection habit?
Interview Yourself
QTAs to Ask About What You Want to Do
What goal should my systems support?
How do I want to use my tools in the year ahead?
What is the source of the friction-frustration that I keep feeling?
What do I want to keep a (long-term) record or archive of?
What do I need to track in order to act on?
What can be deleted?
Understanding Your Current Workflow
Use a decision tree to help you understand the choices you make in your current workflow.
Sometimes we do this unconsciously, based on the tools or options that we have in front of us. Additionally, your professional context might have a specific toolkit that’s already defined for you, which is great!! You just have to go with the flow (however stupid the flow might be).8
But when you have to decide these things for yourself, sometimes it's overwhelming and crazy-making. A decision tree can break it down into the basic categories we deal with on a regular basis, and help make better sense of it.
Bonus: Once you're done interviewing yourself and your tools, you can re-do your decision tree to see if any of your choices have changed.
Interview Your Tools
The 2x2 Matrix
Use the 2x2 matrix to help you understand the tools you use at different stages of working.
What you need during the divergent, all-ideas-welcome, exploratory stage of working is very different from what you need at the convergent, one-idea-to-rule-them-all, definitive stage of working.
The matrix helps you recognize which tools work best at which stage.9
Why Should I Hire You?
Just like we interview people for different roles in an organization, we can interview tools for different roles in our processes and systems.
What functions do you perform?
What are you doing for me?
What do you make it possible for me to do?
What can't I do without you?
What are you keeping me from doing?
What do you make it impossible for me to do?
Do I use this tool to its full capacity?
What does this cost per month / year?
Sum It All Up
Once you've navigated the chaos of your tools, processes, and systems, and you've discerned possible or likely solutions, write it down. Put this summary in a place that you can easily access and refer to it on a regular basis. This helps you both remember what you decided, and also gives you feedback as you execute your processes.
Are you actually doing these things? Does it still make sense to you? Are you getting the results you wanted to get from this system?
I capture tasks and notes…
I can distinguish tasks from notes because…
All my project tasks and notes are kept in…
I prioritize my projects and tasks by…
I decide when the work will happen by…
I work efficiently because when it's time to work, I…
I know how much progress I've made on my projects and tasks because I…
I assess where I am compared to my initial plan because I…
I am prepared for upcoming commitments because I…
Leave the Gun, Take the Cannoli
Here's the main thing I hope you take from this:
Take what works from this. Leave what doesn't.
There's no standard to meet, no roving eye scanning your life10—it's just your goals, purposes, and desires, and the tools and processes that work best for you.
I personally found this process incredibly helpful over the last couple of weeks, and super insightful. If I want to become a better writer, speaker, communicator, teacher, I need to create a stronger, better infrastructure that helps me do that in this season of my life. Hopefully the choices I’ve made will make that happen.
So I hope you find something useful or valuable in what I've learned and shared here—I'd love to hear if you try anything and what you discover.
Have a merry Christmas, happy Hanukkah, blessed Solstice, a rockin’ Festivus, and a happy New Year.
Let's be hopeful, creative, and wise—together.
Shalom,
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For example, Notion has a ton of flexibility in how to arrange pages and access information, but Notion's perspective on software (and the world) derives from blocks and databases: atomized bits and bytes capable of being arranged in any number of combinations. You cannot get away from blocks and databases. Eventually, I realized that, in Notion, I a) lost track of things once they got buried in a database, b) compartmentalized into the atomized Database ways of thinking that were really networked Narrative, and c) had no idea where to capture A Thing so that I could find it later, and make use of it appropriately. By contrast, tools like Miro, Whimsical, Canva whiteboards, and Milanote allow for a TON of information in a single field of vision. While you can collapse or tabulate data in these tools, the connections, access, and referencing operate more like backlinks than relations. The structure of such tools is flat, rather than stacked. It makes a difference in how you conceive of data, information, relationships, and retrieval.
Little, Brian R.. Who Are You, Really?: The Surprising Puzzle of Personality (TED Books) (p. 6). Simon & Schuster/ TED. Kindle Edition.
Little, Brian R.. Who Are You, Really?: The Surprising Puzzle of Personality (TED Books) (p. 30). Simon & Schuster/ TED. Kindle Edition.
Not to mention: I tend to over-engineer my tools and processes. I create complex "if-then" processes that I “think” I’m going to need, which just stresses me out and locks down the creative juice in the long run.
This may take a while—if you have suggestions, let me know!
She says, as she signs up for more cloud-based tools. 🤦♀️
Unless it needs fixing. and you want to fix it. Also an option!
I've talked about this idea before, so check out my video on using the 2x2 matrix, and grab the free PDF worksheet if you want to learn more.
