🎯 A simpler way to think about AI skills

I’m not going to surprise anyone here by saying this:

I’ve been thinking about my professional upskilling journey for 2026 mostly in the context of AI.

And every piece I’ve read about it points in a different direction.

Master this platform. Learn that automation tool. Build agents. Use this prompting framework. Each article confident, each recommendation different. Everyone’s sure they’ve figured it out. And I’m not sure of any of it ¯\_(ツ)_/¯

So, if you’re feeling a bit lost about where to actually focus, just know you’re not alone.

I’ve tried to simplify this for myself. Instead of chasing specific tools or building a complex 30-point learning plan, I’ve been thinking about it in terms of three broader capabilities—the kind that stay relevant regardless of which LLMs win or which features change.

Here’s where I’m focusing.

Master your inputs

AI is only as good as what you feed it. This breaks down into three things:

Communication. Your ability to articulate what you actually want. This sounds obvious, but we’re collectively pretty bad at it. AI companies know this—it’s why the complex agentic tools (Claude Code, OpenAI Codex) now have some form of prompt optimizer built in. They’ve realized we struggle to say what we need clearly.

Context. The best-crafted prompt for writing a blog post will still produce mediocre results if you haven’t told the AI who it’s for, what voice to use, or what makes your brand different. The more complex your task, the more this matters.

I’ve started building a library of “context blocks”—audience profiles, brand voice guidelines, positioning frameworks, process documentation—that I can pull into any project. It’s less glamorous than learning a new tool, but it’s made a bigger difference to my output quality than any single “AI hack.”

Structure. Breaking complex work into discrete steps helps you create AI flows with seamless handoffs and consistent results. Maintaining version control is crucial so that different tools aren’t working with outdated positioning statements. Having a single source of truth for each context piece produces content output that’s aligned with your brand narratives and unique angles.

The more organized your inputs, the more consistent your results. Unsexy, but true.

Sharpen your judgment

AI can now produce text that looks specific and sounds authoritative. But “being meaning-shaped” isn’t the same as “has meaning.” Fluent isn’t the same as insightful.

I was working on a brand voice guide recently. The AI did excellent work analyzing source materials and producing a comprehensive first draft. 16 pages of it… But it was entirely up to me to figure out what deserved its own section, what could be combined, and what was just sophisticated-sounding filler that had to go.

This is where being a better thinker yourself—a better writer, a sharper critic—makes you better at working with AI. You need to catch when something is hollow beneath the surface polish. AI won’t flag its own fluff.

Get comfortable breaking things

I still see a lot of people, especially fellow word-focused marketers, who are hesitant to really experiment with these tools. There’s a vague fear of breaking something or wasting time on tech that might not last.

The antidote is low-risk tinkering. Channel your inner hobby mechanic mixed with mad scientist.

I remember breaking my personal blog twenty times over in my early marketing days, just messing around with CSS and HTML. And I mean breaking it while doing the simplest possible tasks: changing a font color shouldn’t crash your sidebar, and yet. That tinkering gave me an edge when I needed to actually understand how websites worked.

Same principle applies now. I’m currently building a study system for my next wine certification exam using various AI tools. Completely personal, zero stakes—but I’m testing approaches I know I will be able to apply in client work soon.

You only learn where tools excel and where they fall short by playing with them. Give yourself permission to make a mess.

***

You don’t need a complex upskilling roadmap. You need a flexible approach that fits into your actual work.

As I focus on these three areas, I feel the overwhelm gradually dissipating. It’s now easier to keep in mind what I need to focus on and find ways to improve these core capabilities in every project.

I hope this approach gives you some clarity and peace of mind, too.

Focus matters,

📝 From the blog

It’s hard to make a promise and stick to it for a full 12 months. Keeping those promises is mainly affected by two things. One is sheer willpower, and the other is a good process. And the latter is something I’ve researched a TON! Here’s my process for setting annual goals and my steps to stick with them as the year rolls by.

Read the post →

👌 Handpicked stories for you

Here are some interesting things I stumbled upon this week while reading, writing, researching, and being a generally curious marketing person on the internet:

💼 Three for work

Entity-based SEO: An explainer for SEOs and content marketers | This is a pretty decent primer on what “entities” are, how search engines and AI tools treat them, and what you can do so your content reflects the entity-first reality of today.

Reframe Ladder Worksheet | This is an interesting messaging framework to try, centered around switching the beliefs of your audience. I’m still not convinced reframing the problem always works, but I’d test this out.

Content Supply Chain: Transforming B2B Marketing Into a Growth Engine | Adding some structure to content marketing activities may be at the top of your priority list now, and this post will give you clear directions on how to approach it. Though “B2B” is in the title, I think most of it is applicable elsewhere, too.

👀 Two for fun

This look at a typography symbol you never knew how to call | The history and current use of the manicule (that little pointing hand ☞) is pretty awesome!

These fun animal photos | The finalists of The Comedy Wildlife Photo Awards are the type of whimsical content we all need in this doomscrolling world.