Weekend Upgrade provides tools to improve your productivity and communication, especially if you use Tools for Thought like Roam Research, Amplenote, Logseq, or Obsidian.
Weekend Upgrade 1: What's THAT supposed to mean?
Happy Friday, friend!
Storytime
You’re in college, and you have an essay due next week. It’s five pages max—not long, but long enough that you can’t dash it off in 10 minutes.
But it’s going to be so easy. You already know what you want to say.
So you wait. The days slip by—“no worries, I know what to write”—and now it’s the night before the essay is due.
After dinner, you sit down at your laptop, open Word, and…
…stare at the blinking cursor. You start a first sentence, then backspace backspace backspace.
Two minutes crawl by, the screen as bleak and featureless as the Sahara. And that cursor. Blinking. Blinking. It mocks you.
Slowly you realize you do not know what you want to say. You know some broad strokes, loosely linked, but you don’t know where to start, where to end, or what to say in between.
I bet that story sounds familiar.
Maybe it’s an essay, maybe it’s something else. But you know the experience.
We’re so susceptible to this type of procrastination. How do we overcome that?
That’s what we’ll explore in this Weekend Upgrade. But before we do, because this is the first ever Weekend Upgrade newsletter, let me explain the concept.
Each biweekly newsletter will contain a tool to improve your productivity or communication. Tools may upgrade your mindset or your workflow—or both!
We’ll also explore ways to implement productivity and communication workflows in Tools for Thought (TfTs). If you haven’t heard that term, it refers to apps that are optimized for linking your ideas, thoughts, notes, etc.—apps like Roam Research, Amplenote, Logseq, and Obsidian.
Each newsletter will close with action steps you can take over the weekend to add that week’s tool to your toolbox.
My overarching thesis is this: Tools for Thought are ideal for improving your productivity and communication, and I want to help you find ways to leverage that.
Say what you mean to say and do what you mean to do.
👆 That’s your Weekend Upgrade.
There are a couple of ways you could take that. I could be demanding consistency. “If you say you’re going to do something, you should follow through!” While I have no objection to that, it’s not what I want to focus on.
Here’s what I do want to focus on: Until we know what we mean, we’re stuck in the mud.
You can’t say what you mean to say if you don’t know what you mean to say. You’ll never do what you mean to do if you don’t know what you mean to do.
I see this phenomenon all the time when people come to me for coaching. What they think they need are tips and tricks, but what they really need is to better understand what they’re trying to accomplish.
This leads to a deeper question: How do we discover what we mean?
For the sake of clarity, I’m going to keep our scope narrow. We could talk about big-picture priorities—and those are critical—but let’s focus small for now.
When we’re stuck not knowing what to say, or we’re mired in a project and we don’t know what to do next, how do we dig deeper than “one easy trick” and delve into what we really mean?
This is where Tools for Thought come in.
Roam Research is my coach. I mean that quite literally. If I were stuck on a project or presentation, I might hire a coach to help me get unstuck. But I can do that without hiring a coach if I have the questions a coach would ask saved in a Roam template.
What I create for myself, then, are journaling workflows that help me in the moments when I can’t discern what I mean to say or do.
Let me define journaling. To paraphrase my good friend Tracy Winchell, journaling is not carrying a leatherbound volume to the top of a mountain at sunrise and capturing your innermost thoughts.
It’s “meta-writing.” It’s writing about your thoughts, writing about your successes and challenges, writing about your relationships.
And in this case, it’s writing about your communication and productivity—what you say and what you do.
Obviously you don’t need to use TfTs to journal, but they give you superpowers if you do. For most TfTs, if you simply wrap key journaling prompts in double brackets—[[Journaling prompt here]]—you can track every time you answer it. As you follow this practice over weeks and months, you’ll steadily accumulate a history of all the times you’ve had trouble saying or doing what you mean.
And guess what? As that accumulates, you’ll get more efficient and effective at discerning what you truly mean to say and do. Plus, you’ll be more likely to sidestep whatever’s been holding you back before it even stops you. You’ll earn interest on the investment.
So if I’m going to journal to discover what I mean, what do I need to ask myself? How do I narrow down what I mean?
The questions you ask should be tailored to YOU.
But we can pick some good places to start.
A great prompt to start with is [[What do I really want?]]. I took this from the fantastic book Crucial Conversations. They gear the question toward communication but it works just as well for productivity. While responding to this prompt, I recommend writing anything that comes to mind.
Don’t be afraid to repeat [[What do I really want?]] a few times. Often your first response will not refine your meaning far enough. But if you dig a bit deeper—”okay, that’s something I want, but what do I really want?”—you may find larger meaning lurking in your subconscious.
You’ll know if you’ve found it. Any anxiety or frustration will melt away (at least for the moment) and you’ll feel like you solved a riddle—that feeling when you know the answer is right.
Another great general-purpose prompt is [[What am I afraid of?]]. When we have trouble identifying what we really mean to say or do, it’s often because our fears are blinding us. If we can root out the fear, we stand a much better chance of moving forward effectively.
Beyond [[What do I really want?]] and [[What am I afraid of?]], you can explore prompts specific to productivity or communication.
If your challenge is “What do I mean to do?”, try these:
[[Am I in the right place, with the right tools and materials, to work on this?]]. If the answer is no, journal about where you need to be and what you need to have.
[[Is my intent too vague or broad?]]. If the answer is yes, journal about how you can refine what you mean to do into something more immediately actionable.
[[Am I skipping any prerequisite steps?]]. If the answer is yes, journal about what you need to do first to make progress toward what you mean to accomplish.
If your challenge is “What do I mean to say?”, try these:
[[What audience are you addressing?]]. You can’t be clear what you mean to say without the context of who you’re saying it to.
[[What action do you need your audience to take?]] and [[What reasons support (or don’t support) that action?]]. By clarifying what you need to happen as a result of your communication, it can help you understand more clearly what you mean to say.
[[What story can I tell to illuminate my message?]]. What’s fun about this prompt is its two-birds-one-stone effect. Stories help your audience connect with your message, but they can also help you better understand what you’re meaning to say.
Ultimately, of course, you’ll have to find the prompts that work for you, and that will take time. You may borrow some from masters like Tracy Winchell (get her ebook) or create them yourself. You may like having many simple, specific prompts, or only one or two broad open-ended prompts. Or a combination.
But once you have those tools, the next time you’re tempted to put off that essay because “you already know what you want to say,” you can respond to some prompts to make sure you really do. And if you’re trying to work but you’re totally stuck, you have a tool in your toolbox to get your creative juices flowing again.
By journaling—writing about why you can’t say or do what you mean—you’ll get unstuck now. And over time, you’ll accumulate a deep understanding of what sidetracks you.
Try doing that in a task manager or word processor. That’s why TfTs are so powerful for productivity and communication.
What do you do next?
1. Take 2 minutes and answer this question: What’s one thing I learned in this newsletter that I can put into practice right away?
By committing to a specific action, you make it much more likely you’ll do it.
2. Over the weekend, spend a little time gathering or creating your own prompts to help you clarify meaning.
That way, the next time you feel lost in your work or your words, you’ll have tools to reset your course.
If this was valuable for you:
Feel free to forward it to someone you think would like it. And if this was forwarded to you, sign up here if you want to receive the next one: https://rjn.st/weekend-upgrade.
Until next time, friends:
Say what you mean to say and do what you mean to do!
R.J.
Weekend Upgrade (by R.J. Nestor)
Weekend Upgrade provides tools to improve your productivity and communication, especially if you use Tools for Thought like Roam Research, Amplenote, Logseq, or Obsidian.
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