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My AI Skills Guide – Kyle Jennings

MY AI SKILLS GUIDE

How I’m equipping myself for an AI World

0 of 9 skills explored

Using the LLMs Constantly

The obvious answer is that I’m using the LLMs constantly. Not as a replacement for thinking, but as a tool to make my work more efficient, effective, and expansive.

The more you use these tools, the better you get at understanding what they’re good at, what they suck at, and how to prompt them to get the results you actually need.

How I’m using it…
  • In my copywriting work… not to write for me, but to help make my writing more efficient, effective, etc.
  • In my personal reflections… as a way to develop unique journal prompts (based on the ones I’ve found most fruitful in the past), to summarize past reflection journals, and to give me takeaways from those journals that I hadn’t spotted myself
  • To transcribe & summarize voice memos… since I tend to think best while walking, I’ve been taking lots of voice notes through my iPhone – then using AI to summarize and make those voice notes coherent. It’s been a major unlock for helping me increase output ~ tenfold

❓ Questioning

Kevin Kelly explains that “Machines are for answers. Humans are for questions.”

And in a world where AI gives everyone equal access to an incredible amount of information – sort of leveling the playing field – then, the advantage becomes to ask better questions.

How I’m developing this skill…
  • Constantly using AI (noticing what prompts/questions deliver the best responses)
  • Starting an interview podcast (called Learning Freelance)
  • Listening to exceptional podcast interviewers (The Tim Ferriss Show, Modern Wisdom, Daily Stoic, Tetragrammaton)

First Principles Thinking

Prompting is a great way to break a problem down into its component parts — you’re not just writing a landing page, you’re taking a prospect who feels uncertain and distracted, helping them see a clear path forward, and guiding them to take action.

You’re not just delivering an asset — you’re uncovering the deeper mechanics of what it’s really meant to do.

How I’m developing this skill…
  • Deconstructing winning marketing examples (great copy, ads, strategies, etc.)
  • Using AI as a Socratic partner (asking “what assumptions am I missing here?” and “what are the fundamental parts of this challenge?”)

Having Good Taste

Which to me, essentially means two things –

Becoming attuned with my intuition – so I have a clear sense of what lights me up.

Reflect – so I actually pay attention to and take note of the things that light me up.

How I’m developing this skill…
  • Taking notice of the things that light me up inside and give me an excited energy (art, learning resources, etc.)
  • Using AI to help me understand commonalities between the things that I may not have seen on my own

Critical Thinking

And this is especially important, since an over-reliance on AI can lead to an atrophying of this very skill.

Writing is ultimately a tool for thinking, and AI should be used to refine and expand your thinking – not replace it. Critical thinking is crucial because without it, people risk outsourcing judgment to a machine, which will lead to shallow, unfocused work.

How I’m developing this skill…
  • Constantly asking questions – especially the most obvious ones. (“Why” and “How”)
  • Evaluating evidence, instead of taking things at face value
  • Asking AI to give evidence/explanations for every single response
  • Deliberately exposing myself to different perspectives (which means seeking things out beyond my algorithm)

Distillation & Compression

The world isn’t starving for more information — it’s choking on it. The real skill is boiling hours of content or pages of notes into one insight that matters.

How I’m developing this skill…
  • Practicing one-sentence or tweet-length summaries of long inputs
  • Using the 80/20 principle constantly – what is the 20% that really matters most?

Persuasion Psychology

In this changing world with AI, I believe my role as a copywriter isn’t so much in “writing” – it’s more in being the architect of language. Asking “how can I best use words to get the reader from point A to point B?”

So, I’m going back to the very basic, evergreen principles of persuasion.

How I’m developing this skill…
  • Re-reading the classics (Influence by Cialdini, This Is Marketing by Godin)
  • Tuning out the “new exciting trend” (I’d rather focus on the evergreen principles than ever-changing tactics)
  • Writing as much damn copy as humanly possible

Storytelling Skills

Stories are how humans make meaning. In a world where AI can crank out infinite content, story becomes the ultimate differentiator.

How I’m developing this skill…
  • Writing a lot more
  • Speaking a lot more (starting a podcast)
  • Studying the structure of great stories

Magnetic Marketing

As coined by the brilliant Dan Kennedy. I think that in this AI world, humanity will become even more critical. And so, I believe that personal brands will become much more important.

How I’m developing this skill…
  • Listening to a ton of the BenSettle.com Podcast and Dan Kennedy’s Magnetic Marketing Podcast
  • Studying my favorite personalities – and breaking down why I feel drawn to them