🗺️ How to Stay Directionally Correct in 2025


In this edition of Practical PKM:

  • 💡 The Big Idea: Make constant progress through tiny experiments
  • 😎 Something Cool: An Obsidian plugin that FINALLY enables Markdown links in Properties
  • 📚 My book notes from Scrum by Jeff & J.J. Sutherland

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💡 The Big Idea: You Can Be Accurate Without Being Precise

Recently, I was listening to the Nathan Barry Show podcast, and he was talking to a guest about managing projects.

(If you’re unfamiliar with Nathan, he’s the CEO of Kit (formerly ConvertKit), which is what I use to send my newsletter. I’ve met him several times and even interviewed him for the Focused podcast a while back.)

On his podcast, he mentioned that they always use weeks when estimating how long something will take during project planning:

  • Estimating days required too much precision and led to inaccuracy
  • Estimating in months didn’t provide the motivation necessary to make meaningful progress

Estimating in weeks was the sweet spot that provided the margin necessary to accommodate the unexpected. Even when a single day went sideways, there was still time to get things back on track.

Making better estimates requires more than just the right unit of estimation. It requires a feedback mechanism that you can use to course correct as necessary.

That's where feedback loops come in.

The Importance of Feedback Loops

The difficult part about estimating projects is that you don’t know what you don’t know. This is why when we try to estimate big projects, it tends to take about twice as long as we think and costs twice as much. For example:

  • The Sydney Opera House was expected to be completed in 1963, but a scaled-down version didn’t open until 1973, a decade later. The original cost was estimated at $7 million, but its delayed completion led to a cost of $102 million.
  • The Denver International Airport opened sixteen months later than scheduled with a total cost of $4.8 billion, which was over $2 billion more than expected.

The solution isn’t to pad the estimates, however. It’s to break it down into smaller parts and ship them in sprints.

Sprints are an agile project management philosophy commonly used in product development. The basic idea is to:

  1. Pick the tasks you’re going to work on in the next sprint as a team
  2. Agree on how long you think each task will take and budget the team's resources realistically
  3. At the end of the sprint, look at how you did and make improvements that will eliminate future roadblocks

There’s a lot more to the mechanics of this, but here’s the takeaway:

By using short sprints and shipping small pieces, we can make CONSIDERABLY more progress.

So instead of picking a big project that that you estimate will take six months, lean into the fact that there are a lot of unknowns. Figure out the smallest piece of that you can work on, and then ship that within a couple of weeks (before the next sprint starts).

This method does more than increase your productivity, though. It also help make sure that we stay directionally correct.

How to Stay Directionally Correct

Directionally correct is a term that means “generally accurate or true.” If something is directionally correct, it may be accurate but may not be precise. The term is used often in data analysis when the specific details don’t tell the larger story (something my data analyst friend says happens all the time).

Put another way, it’s “seeing the forest through the trees.”

So, how do you stay directionally correct? By running tiny experiments.

You’ll never have perfect information. There will always be an element of uncertainty in any decision you make. Think like a scientist and conduct experiments with the intention of learning something new that will help you in the future.

The thing about being directionally correct is that you can afford to make a wrong turn every once in a while. As long as you reflect regularly, you can course correct before you go too far in any wrong direction.

But there is a simple strategy you can use to even further diminish the negative outcomes of wrong decisions.

You can minimize the significance of wrong choices by asking yourself a simple question:

What can I do in the short term that would change the confidence level?

That’s your tiny experiment. Do that, get some data, then re-evaluate. This will help you be more accurate in the long run

One of the ways I do this is my quarterly Personal Retreat. I written about this before, but it’s basically one-day reflection process I do every 90 days where I reflect on the last quarter and plan the next one. It’s loosely based on the 12-Week Year concept, which emphasizes setting quarterly objectives instead yearly. This gives you four feedback loops over the same timeframe, making it easier to stay “directionally correct.”

Living directionally correct for me means living in alignment with my LifeTheme and personal core values. And when I’m not sure whether I should take a certain course of action, I can always test it for a quarter and see how it goes.

No long term commitment required. Plus, when I get done, I’ll have the information I need to increase my confidence level for making the bigger decision.

As 2024 wraps up, I encourage you NOT to do the traditional New Year’s resolution (which fail 92% of the time). You have no idea what the next 12 months will bring anyway.

Instead, make this the year you live directionally correct.

😎 Something Cool: Postcard Cabins

I’ve mentioned these before but under a different name. Several months ago, Getaway House rebranded to Postcard Cabins. But they’re still an amazing place to host your next Personal Retreat.

If you're unfamiliar, Postcard Cabins are basically a tiny house plopped on a campsite in the middle of the woods. It's a great place to unplug and think for awhile.

I’ll actually be going to one of these on Thursday for my next Personal Retreat. And if you want a more detailed look at the cabins and the experience, I put together this YouTube video a while back.

😎 Something Else Cool: Frontmatter Markdown Links

One of my problems with Properties has been the poor support for links. Yes, you can use double brackets, and web URLs become clickable when you paste them, but they’re clunky, and it’s a crime that standard Markdown links are not supported. There have been a few attempts to fix this over the years, but I recently came across a plugin that does exactly what I was looking for called the Frontmatter Markdown Links plugin.

This simple plugin fixes all of these shortcomings by simply allowing you to use Markdown-formatted links in Frontmatter Properties.

It’s not available in the Community Plugins directory (at least, not yet), so if you want to use it you’ll need to install it via BRAT. There’s documentation on how to do that here.

📚 Book Notes: Scrum by Jeff & J.J. Sutherland

I mentioned agile product development in this newsletter, and one of the more popular applications of this is a framework called Scrum. In fact, it’s estimated that 75% of the teams that use “Agile” also use Scrum (or a Scrum-inspired approach).

The person credited with inventing Scrum is Jeff Sutherland. And fortunately, he wrote a very approachable book on the subject with his son, J.J., titled Scrum: The Art of Doing Twice the Work in Half the Time.

Now before you dismiss the book entirely based on that clickbaity title, it’s actually a really good primer. If you’re looking for a good introduction to the topic of Scrum, this is a good one to read.

And if you want to download my personal book notes in mind map format, just click here.

— Mike

Practical PKM

A weekly newsletter where I help people apply values-based productivity principles and systems for personal growth, primarily using Obsidian. Subscribe if you want to make more of your notes and ideas.

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