I absolutely love the holiday season here in the USA. Thanksgiving is great. Christmas is great. Everything in-between is the best.

I optimize for a slow, relaxed December in the business; personal life with school pageants, familial obligations, and off days is crazy.

I also like to take the end of the year to do three things:

• Plan for the next year.
• Do my year end posts (Favorites, Yearly Theme, etc.).
• Review my systems, tools, and workflows to see what I can do better.

I like to view systems and workflows like a car. In many states (somewhere between 19 and 37 when I ask AI), some sort of car inspection is required.

You hope that it doesn’t need major work — especially in a state like mine where annual inspections are required — but it’s important to fix something when you discover a problem.

So here’s my approach.

Tools Review

First, I take a look at all the tools I use (paid and free) and review how I use them. I also look for major features they released that I may have missed, and any overlap between tools.

For example, I’m using Obsidian to write this, but I also use Ulysses for writing. And I use Bear Notes for note taking. There is definitely overlap between these tools.

Then I look at how I’m using the tools: where and when do I use them? Do I need to use them at all? Is there a world where I can consolidate Obsidian, Ulysses, and Bear?

Crucially, am I paying for tools I don’t need to pay for? Would it be better for me to switch to monthly, or to annually?

Should I spread out expenses a little more? This one is especially helpful if you’ve taken advantage of a lot Cyber Week deals.

Workflows Review

Once I have an understanding of the tools I use, I look at the workflows for those tools. How are they helping me do my work better?

If we look at the Obsidian, Ulysses, and Bear, I have 3 distinct use cases for them:

• Obsidian is my PKM. Pretty much everything I write/think about makes it into there at some point. I’ve also enjoyed writing my articles in it — a function I never thought I’d do outside Ulysses.
• Speaking of, Ulysses at this point provides one crucial workflow: publishing the articles to my websites. Ulysses has great integration with WordPress, making publishing a lot easier.
• Bear Notes is my current note-taking app. It’s much faster than Obsidian, especially on my iPhone, and has good Shortcuts integration, and an Apple Watch complication. This is important because I deeply value quick capture on my devices. It’s the main reason Obsidian isn’t also my notes app.

Part of looking at my workflows is also looking at what Zapier, Make, Hazel, and Shortcuts automations I have set up…as well as what I’m still doing manually.

Are there conflicts between those automations? Sometimes I’ll set up automations within tools and not realize Zapier was already doing them. Am I doing something with a 3rd party tool that now has native support?

When Notion added the ability to send emails through GMail, it greatly simplified several of my workflows.

Is there something missing? Looking over the things I do manually, how can I automate or delegate? Am I using my team effectively?

Systems Review

It’s after I look at my tools and workflows that I look at the overall systems. Is everything running smoothly? Is there overlap on what I’m doing? Are the jobs to be done clear?

I do this every year because it’s easy to react when you’re in the thick of trying to get work done. But I purposefully make time at the end of the year to review what I’ve done and make it better.

I usually take 16-32 hours to do this. A lot has changed for me this year, so it might be closer to 32.

But I know it’s important work to hit the ground running in the new year — especially because I do take so much time off. There’s a little rust at the beginning of the year so having good, well-documented systems in place is a must.

Applying this Assessment

Now, I am working on Notion template for this, which I’ll share to my mailing list in December. The gist is:

1. Write down all the tools you use, how you use them, and if you pay for them monthly or annually (or at all)
2. Then write down how those tools fit into your workflows. How they talk to each other, and if there’s any automated parts of them.
3. Finally, take a look at the system. How the tools are connected, what they each do, and what you’re delegating vs. what you do yourself.

Like I said, it takes me 16-32 hours to do this and I do it every year. Your mileage may vary.

That said… if you do want some help, I’ve made a handful of slots available in December for Business Systems Assessments. I’ll work through the entire framework above and we’ll meet for 90 minutes to go through all of it.

You’ll get specific recommendations, automation templates, and a road map for you to make the adjustments you need ahead of the new year.

Want to hit the ground running in 2026? Book a Business Systems Assessment today.

Now, this isn’t a Cyber Week deal, per se. But I am increasing the price by 30% after Christmas. Even if you book for January, as long as you purchase before December 26th, you’ll get it for $997 instead of $1497.