Storytime: You’re the boss
You run a small company in a fast-paced industry. You have several projects in the works—everyone on your team is spearheading at least one.
Today, a new important project arrives on your desk. You delegate it to your team’s newest member. They’re inexperienced, but “trial by fire,” right? They have to start somewhere.
When you assign them the project, you tell them: “I don’t hold your hand, and I don’t micromanage.” You smile—it feels good to empower people.
And you’re true to your word. You provide them no framework, no timeline, no indicators of success, no process, no resources, no idea when or how to check in with you.
After all, what’s the point of delegating if you have to figure out all that stuff? Might as well do it yourself, right?
Three weeks later, you call them into your office for an update. And the project is an absolute mess. There’s work done on stuff that doesn’t matter, work missed on stuff that does matter, and the whole thing is in disarray.
Whose fault is it?
Is it the new staff member? Surely they could have been more proactive. They could have checked in more. They could have asked their colleagues for guidance.
But… maybe it’s your fault. You could have been clearer about the goals and processes. You could have directed them to valuable resources. You could have established a timeline for checking in with you.
Likely the best answer is this: there’s plenty of fault to go around. Both parties could have done much better.
But the moral of the story isn’t “It’s everyone’s fault.” To find the moral, we need go one step further.
The plot thickens
Let’s imagine that you play both roles in this story. Simultaneously (sort of).
Imagine that Today You—the right-now version of you—is the boss, and Future You is the new team member.
That means Today You assigns the project, but gives no framework, shares no indicators of success, provides no process or tools, and offers no way to monitor progress.
And Future You receives that assignment and flounders in various ways—ignoring important work, taking a stab at work that doesn’t ultimately matter, and so forth.
Predictably, the project falls apart. Whose fault is that? Today You or Future You?
Could Future You have been more proactive? Sure. But remember:
👉 Today You is Yesterday You’s Tomorrow You, and how proactive do you feel today?
Which leads us to our moral:
Productivity is communication
It’s easy to see this on the level of an organization. If the manager isn’t communicating with the team, if the colleagues aren’t communicating with each other, the organization will not be productive.
It’s harder to see on the personal level, but it’s no less true. If you aren’t communicating with Future You clearly and reliably, you are not going to be consistently productive. You’ll work in circles, you’ll miss the forest for the trees.
“Okay, R.J., I get it”
“I need to communicate well with myself if I want to be more productive. But what do I need to do? What’s the mechanism?”
First, here are three simple guidelines for communicating with Future You:
When you plan, write instructions for Future You as though you were writing for a different person altogether. Because you are! I’m not the same person I was 10 years ago, and in some ways I’m not the same person I was 10 days ago. I need to assume that Future Me won’t know what the heck I’m talking about.
If Future You doesn’t know exactly what to do, the work probably won’t get done. Define precisely what you’d like Future You to do.
Your instructions are not a Blood Oath. No evil will befall Future You if they find a different or more productive way to use their time. Be clear and specific, but know that you’re creating guidelines for Future You, not prison bars.
But not all projects are predictable!
Sometimes, we don’t have anything clear and specific to provide as guidelines. The project is exploring new space, and discovery is part of the goal.
When that happens, first think “meta.” Hop up a level from the work to the metawork—the work about the work, the process/workflow level. Ask yourself how to be clear and specific on that level. What’s the next thing you need to do on the process level to make sure you can be clear and specific on the work level?
Whether you’re at the work or the metawork level, then, your goal is to come away with something clear and specific to guide yourself in the future.
That brings us to our unifying mechanism, which is simple and actionable:
💡 Never leave a work session without defining what you’re going to do next. 💡
👆 That’s your weekend upgrade.
There are “startup costs” when you begin a work session. It takes time and energy to gather required materials and resources, get reoriented in the project, and decide what to do next.
If you apply this weekend upgrade, you’ll greatly reduce those costs. You’ll have your materials and resources waiting for you. You’ll be able to see immediately what you’ve done already and what direction you’re heading. And, most important, your next step will already be decided for you.
It is orders of magnitude easier to decide what to do next before you leave this work session than it is to figure it out at the beginning of the next session. You’re already in the project’s headspace. You’re working with the project resources. Now is the time to decide—before you stop working.
I call this goal Always be in the middle. Get yourself into the “middle” of the next work session before you leave this one. That way, when you pick up this work again, you’ll get started much more easily.
How do Tools for Thought help?
If you’re new to the Weekend Upgrade newsletter, I explore how processes can be created in Tools for Thought (TfTs). TfTs are apps optimized for linking your ideas, thoughts, notes, etc.—apps like Roam Research, Amplenote, Logseq, and Obsidian.
Let’s start simple
Schedule five minutes at the end of each work day to go to tomorrow’s daily note (in your TfT of choice) and write down what you’d like to accomplish tomorrow.
This is an adaptation of a journaling technique I learned from Tracy Winchell called the “Note to Next Day Self.” If you get into the middle of tomorrow’s thinking before you leave today, you’ll reduce the “startup cost” of getting your work going tomorrow. (The original “Note to Next Day Self” isn’t about productivity, per se, but the concept still works!)
When tomorrow becomes today, you’ll have instructions waiting for you on the daily note. You’re still free to do whatever you want, but having those guidelines available makes you far more likely to have a productive day.
If you’re like me, every day’s work moves several projects forward. Rather than getting into the middle of tomorrow’s work, then, I prefer to get into the middle of the next work session for each of those projects.
To do that, I need a system for defining what’s next on a project-by-project level. Tools for Thought are amazing for this!
Here’s a simple implementation: at the end of each work session, type a [[page reference for the project]] combined with a #next tag (or something similar).
Then, under that reference and tag (indented under them if you’re in an outliner like Roam or Logseq), list links to relevant resources—URLs, references, etc.
Last, under the resources create a task that clearly states what you want to do next.
This way, the next time you work on this project, you can visit the project page and filter or search the backlinks for the #next tag. There you’ll find everything you need to start working. (Once you get going, delete that #next tag so it won’t interfere with future work.)
Instead of spending several minutes gathering resources and reorienting, you spend a few seconds finding the materials and then get started right away.
Full productivity system
You can expand this approach to make it as robust as you need it to be. I have a full GTD backend built into my Roam Research system. I have a friend who has designed a similar workflow in Obsidian.
With a setup like that, you can combine even more tags and references to provide valuable context for your work. And when you build it the right way—meaning, tailored to the way you think and work—it makes work so much easier.
That’s the central goal of my cohort course AP Productivity—designing a custom workflow that keeps you in the middle of all your work, without stress and anxiety. But you don’t necessarily need a course. You can do it yourself, if you have the patience!
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, build a “what’s next” workflow into your system.
It can be as simple as “what do I want to do tomorrow?” or as specific as “what do I want to do next on this project?”. And then use that workflow, and iterate to make it better!
If this was valuable for you:
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: rjn.st/weekend-upgrade.
Until next time, friends:
Figure out what’s next and write it down for Future You. It’ll make tomorrow much more productive!
P.S. I’m writing a novel in Obsidian and publishing it chapter by chapter using Obsidian Publish. If you’d like to read the novel or follow along as I document what I learn about the process, sign up for an email reminder when I release new chapters: rjn.st/time-worn-signup. And follow the novel’s account on Twitter!