Nate Herk | AI Automation
20 min video
3 min read
6 AI Skills to Future-Proof Your Career
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The big takeaway
Master six essential AI skills to remain competitive: become the AI person in your circle, develop taste and judgment to evaluate AI outputs, learn context engineering to provide AI with relevant information, build iteration speed to move faster than competitors, create autonomous systems (your Jarvis) that work without constant triggering, and develop multiple income streams using AI to protect against job loss.
Skill 1: Become the AI Person
Being the AI person is relative, not absolute
You don't need to be the world's best AI engineer or understand every model's architecture. Being the AI person simply means knowing more than the people in your immediate circle. This relative advantage matters far more than absolute expertise and opens doors before formal job titles exist.
Show your work to become known
Start building small AI projects, automating tasks at work, or creating weekend experiments. When you show colleagues what you've built—like automating a 3-hour task down to 20 minutes—you become known as the AI person. This reputation leads to opportunities when companies need AI leadership.
CEOs expect all functional leaders to become tech experts
IBM's 2026 CEO study found that 85% of CEOs said all functional leaders must become technology experts in their domain, not just IT teams. This applies to marketing, sales, finance, ops, legal, and customer success—every role will need AI.
85%
of CEOs say all functional leaders must become tech experts
IBM 2026 CEO Study
AI adoption mirrors past technology shifts
Just as accountants who refused to learn Excel became obsolete, refusing to adopt AI will make you obsolete. The people who learned Excel first could process spreadsheets in a fraction of the time, setting a new productivity baseline. AI is a much larger shift.
Practical first steps: pick one tool and one workflow
Choose one main AI tool (like Claude) and get genuinely good with it—not just experimenting, but using it to deliver real ROI. Then identify one recurring task in your job and figure out how to use AI to make it faster or better. Document the before/after metrics.
Skill 2: Taste and Judgment
The trap of trusting AI output too easily
As AI improves, it's tempting to accept the first output without review. But this is dangerous: you might miss small tells (like excessive em dashes) that signal AI authorship, which changes how others interpret your work and whether they trust it.
Your name is signed to everything you produce
Whether AI wrote it or you wrote it, your name is attached to the output. If it's great, you get credit. If it's bad, you take the blame. This means you must develop taste to decide what deserves your signature.
Build taste through three practices
First, study the best work in your field. Second, save examples of work you like and ask why it's good. Third, every time you correct AI, feed that correction back into your instructions so the system learns your taste over time.
1
Study the best work in your field
2
Save examples and ask why they're good
3
Correct AI and feed corrections back into instructions
Three ways to build taste
AI still needs human judgment in every field
AI can write sales emails, but you must know if it will annoy the prospect. AI can draft HR memos, but you must know if it will make employees uncomfortable. AI can create motion graphics, but you must judge timing and whether they distract or help.
Skill 3: Context Engineering
Context engineering replaces prompt engineering
Prompt engineering (giving good instructions) is becoming less important as models improve. Context engineering—filling the AI's context window with the right information about your business, priorities, and data—is far more durable because models will always need to know what's actually in your world.
Build your AI operating system
Create a system that knows your meeting transcripts, videos, emails, Slack channels, calendar, and priorities. This gives AI so much context about you that it can answer questions better and faster than you can, and can even anticipate what you need.
Stop opening blank chats; use projects instead
Instead of opening Claude or ChatGPT fresh each time, create a project and feed it real context: product details, marketing calendars, past copy that worked or failed. Now AI works with your actual data, not generic best practices.
Context is what makes outputs unique
If everyone uses the same model and asks the same questions, everyone gets the same outputs. Your unique context—your subject matter expertise, IP, and business data—is what makes your AI's outputs different. Garbage in, garbage out.
Skill 4: Iteration Speed
Iteration speed is the biggest separator in the AI era
People who iterate fastest win. Each iteration teaches you what's working and what's not, making your skills, agents, and prompts better. Moving fast without sacrificing quality means you outperform everyone else.
Build the ugly version fast, then iterate
Don't plan the perfect version. Use rapid prototyping: build something rough quickly, see what breaks, fix it, and iterate. This is how you escape proof-of-concept and move toward production.
Master keyboard shortcuts and use voice input
Stop using your mouse for everything and stop typing everything. Use voice-to-text tools instead—they're much faster than typing. These small optimizations compound to significantly increase your iteration speed.
Define done before you start building
Tie each automation to one specific business metric (e.g., tickets resolved per day, qualified appointments per week, refund percentage down by X%). Define what done looks like before building, then build until you hit it and move to maintenance mode. This prevents endless scope creep.
Teaching the process gets faster each time
Teaching one person to ride a bike is hard. Teaching the second is easier. By the 15th, you have the process down to a science. The same applies to building AI agents: your process improves with each use case, making you faster at building the next one.
Skill 5: Building Your Jarvis (Autonomous Systems)
Move from triggered to autonomous systems
A triggered automation only runs when you fire it off. A true Jarvis runs in the background, notices things, and acts without you having to be present. This is real leverage—systems working while you're in meetings, on walks, or on vacation.
Audit your week for predictable triggers
Identify tasks triggered by predictable events: specific email types, Monday mornings, Wednesday evenings, new CRM leads. Each trigger is something you can hand to a system to execute automatically.
Vending machines vs. slot machines: know the difference
Vending machines are deterministic (same input, same output every time). Slot machines are not (unpredictable outcomes). Simple workflows are vending machines—cheap, reliable, never break. AI agents are slot machines—powerful but risky, costly, and fail in unexpected ways.
Simple Workflow (Vending Machine)
5 minutes to build
AI Agent (Slot Machine)
60 minutes to build
Complexity and risk comparison
Not every task needs AI
Pulling last week's revenue from Stripe every morning and posting to Slack doesn't need an AI agent—a simple workflow does it faster, cheaper, and with zero risk. But reading messy customer emails and drafting tailored responses does need AI because the input is unpredictable.
Ask two questions before automating
First: Does the system need to fire this on its own, or do I need to trigger it? Second: Does this actually need AI, or could a Python script or no-code workflow do it cheaper with less risk? Default to the simplest solution that works.
Skill 6: Unemployment Insurance (Multiple Income Streams)
Job stacking: the new career model
The old model was one job, one income, one 401k. The emerging model is job stacking: your day job plus multiple AI-powered side income streams. Many people already run multiple remote jobs and side projects that together exceed a single full-time salary.
AI enables one person to do work that took five
Because AI lets one person do the work of a team, it's becoming possible to stack multiple income streams without burning out. This trend will become far more common as AI capabilities increase.
One passion with multiple branches beats scattered domains
Don't try to stack five completely different income streams—you'll burn out and fail. Instead, pick one thing you're passionate about and package it multiple ways: your career is the foundation, then branch into a course, niche newsletter, micro SaaS, or consulting—all in the same domain.
1
Pick one passion or expertise
2
Foundation: your day job
3
Branch 1: course or newsletter
4
Branch 2: micro SaaS or product
5
Branch 3: consulting or services
One passion, multiple income branches
Building in public is the default move
Experiment with AI tools, build small things, and share what you're learning. Document wins and losses. The second you start posting, you become discoverable—opportunities, clients, and job offers show up. People want to work with those actually doing the work.
Be discoverable to AI search interfaces
As humans increasingly search through AI interfaces, if you don't exist somewhere an AI can find you and your work, it's much harder to be discovered. Building in public or maintaining some public presence ensures AI systems can surface you.
Check your employment contract and stay safe
Before building side income streams, review your employment contract for non-competes, disclose side work if required, and don't burn your day job chasing side projects. Be smart and don't do anything sketchy.
Worth quoting
"Being the AI person is relative. It just means that inside of your circle, you know more than the other people."
— Nate Herk, at [1:01]
"Your name is signed to it. Whether that is something really good or something bad, you will take the blame."
— Nate Herk, at [7:06]
"The people who win in the AI era aren't the ones building the fanciest agents, they're the ones building systems that run quietly in the background, costing almost nothing, and doing real work."
— Nate Herk, at [16:12]
Try this
Pick one main AI tool (like Claude) and commit to using it for real work, not just experimentation, until you deliver measurable ROI.
Identify one recurring task in your current job and use AI to automate or accelerate it; document the before/after time and results.
Create a project or custom GPT with real context from your work (documents, past examples, calendars, data) instead of opening blank chats.
Build a library of great work in your field; save examples and analyze what makes them good, then feed corrections back into your AI instructions.
Audit your weekly tasks and identify predictable triggers (specific emails, time-based events, CRM actions) that could be automated.
For each automation, ask: Does this need AI or could a simple workflow do it? Does the system need to fire on its own or do I trigger it?
Start building in public: experiment with AI, share small projects, document wins and losses, and make yourself discoverable.
Define one business metric for each automation (tickets resolved, appointments set, refund rate) and build until you hit it, then move to maintenance mode.
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6 AI Skills to Future-Proof Your Career

Summary of the video “Learn These 6 AI Skills Now (Before Everyone Else Does) by Nate Herk | AI Automation.

Master six essential AI skills to remain competitive: become the AI person in your circle, develop taste and judgment to evaluate AI outputs, learn context engineering to provide AI with relevant information, build iteration speed to move faster than competitors, create autonomous systems (your Jarvis) that work without constant triggering, and develop multiple income streams using AI to protect against job loss.

Skill 1: Become the AI Person

Being the AI person is relative, not absolute

You don't need to be the world's best AI engineer or understand every model's architecture. Being the AI person simply means knowing more than the people in your immediate circle. This relative advantage matters far more than absolute expertise and opens doors before formal job titles exist.

Show your work to become known

Start building small AI projects, automating tasks at work, or creating weekend experiments. When you show colleagues what you've built—like automating a 3-hour task down to 20 minutes—you become known as the AI person. This reputation leads to opportunities when companies need AI leadership.

CEOs expect all functional leaders to become tech experts

IBM's 2026 CEO study found that 85% of CEOs said all functional leaders must become technology experts in their domain, not just IT teams. This applies to marketing, sales, finance, ops, legal, and customer success—every role will need AI.

AI adoption mirrors past technology shifts

Just as accountants who refused to learn Excel became obsolete, refusing to adopt AI will make you obsolete. The people who learned Excel first could process spreadsheets in a fraction of the time, setting a new productivity baseline. AI is a much larger shift.

Practical first steps: pick one tool and one workflow

Choose one main AI tool (like Claude) and get genuinely good with it—not just experimenting, but using it to deliver real ROI. Then identify one recurring task in your job and figure out how to use AI to make it faster or better. Document the before/after metrics.

Skill 2: Taste and Judgment

The trap of trusting AI output too easily

As AI improves, it's tempting to accept the first output without review. But this is dangerous: you might miss small tells (like excessive em dashes) that signal AI authorship, which changes how others interpret your work and whether they trust it.

Your name is signed to everything you produce

Whether AI wrote it or you wrote it, your name is attached to the output. If it's great, you get credit. If it's bad, you take the blame. This means you must develop taste to decide what deserves your signature.

Build taste through three practices

First, study the best work in your field. Second, save examples of work you like and ask why it's good. Third, every time you correct AI, feed that correction back into your instructions so the system learns your taste over time.

AI still needs human judgment in every field

AI can write sales emails, but you must know if it will annoy the prospect. AI can draft HR memos, but you must know if it will make employees uncomfortable. AI can create motion graphics, but you must judge timing and whether they distract or help.

Skill 3: Context Engineering

Context engineering replaces prompt engineering

Prompt engineering (giving good instructions) is becoming less important as models improve. Context engineering—filling the AI's context window with the right information about your business, priorities, and data—is far more durable because models will always need to know what's actually in your world.

Build your AI operating system

Create a system that knows your meeting transcripts, videos, emails, Slack channels, calendar, and priorities. This gives AI so much context about you that it can answer questions better and faster than you can, and can even anticipate what you need.

Stop opening blank chats; use projects instead

Instead of opening Claude or ChatGPT fresh each time, create a project and feed it real context: product details, marketing calendars, past copy that worked or failed. Now AI works with your actual data, not generic best practices.

Context is what makes outputs unique

If everyone uses the same model and asks the same questions, everyone gets the same outputs. Your unique context—your subject matter expertise, IP, and business data—is what makes your AI's outputs different. Garbage in, garbage out.

Skill 4: Iteration Speed

Iteration speed is the biggest separator in the AI era

People who iterate fastest win. Each iteration teaches you what's working and what's not, making your skills, agents, and prompts better. Moving fast without sacrificing quality means you outperform everyone else.

Build the ugly version fast, then iterate

Don't plan the perfect version. Use rapid prototyping: build something rough quickly, see what breaks, fix it, and iterate. This is how you escape proof-of-concept and move toward production.

Master keyboard shortcuts and use voice input

Stop using your mouse for everything and stop typing everything. Use voice-to-text tools instead—they're much faster than typing. These small optimizations compound to significantly increase your iteration speed.

Define done before you start building

Tie each automation to one specific business metric (e.g., tickets resolved per day, qualified appointments per week, refund percentage down by X%). Define what done looks like before building, then build until you hit it and move to maintenance mode. This prevents endless scope creep.

Teaching the process gets faster each time

Teaching one person to ride a bike is hard. Teaching the second is easier. By the 15th, you have the process down to a science. The same applies to building AI agents: your process improves with each use case, making you faster at building the next one.

Skill 5: Building Your Jarvis (Autonomous Systems)

Move from triggered to autonomous systems

A triggered automation only runs when you fire it off. A true Jarvis runs in the background, notices things, and acts without you having to be present. This is real leverage—systems working while you're in meetings, on walks, or on vacation.

Audit your week for predictable triggers

Identify tasks triggered by predictable events: specific email types, Monday mornings, Wednesday evenings, new CRM leads. Each trigger is something you can hand to a system to execute automatically.

Vending machines vs. slot machines: know the difference

Vending machines are deterministic (same input, same output every time). Slot machines are not (unpredictable outcomes). Simple workflows are vending machines—cheap, reliable, never break. AI agents are slot machines—powerful but risky, costly, and fail in unexpected ways.

Not every task needs AI

Pulling last week's revenue from Stripe every morning and posting to Slack doesn't need an AI agent—a simple workflow does it faster, cheaper, and with zero risk. But reading messy customer emails and drafting tailored responses does need AI because the input is unpredictable.

Ask two questions before automating

First: Does the system need to fire this on its own, or do I need to trigger it? Second: Does this actually need AI, or could a Python script or no-code workflow do it cheaper with less risk? Default to the simplest solution that works.

Skill 6: Unemployment Insurance (Multiple Income Streams)

Job stacking: the new career model

The old model was one job, one income, one 401k. The emerging model is job stacking: your day job plus multiple AI-powered side income streams. Many people already run multiple remote jobs and side projects that together exceed a single full-time salary.

AI enables one person to do work that took five

Because AI lets one person do the work of a team, it's becoming possible to stack multiple income streams without burning out. This trend will become far more common as AI capabilities increase.

One passion with multiple branches beats scattered domains

Don't try to stack five completely different income streams—you'll burn out and fail. Instead, pick one thing you're passionate about and package it multiple ways: your career is the foundation, then branch into a course, niche newsletter, micro SaaS, or consulting—all in the same domain.

Building in public is the default move

Experiment with AI tools, build small things, and share what you're learning. Document wins and losses. The second you start posting, you become discoverable—opportunities, clients, and job offers show up. People want to work with those actually doing the work.

Be discoverable to AI search interfaces

As humans increasingly search through AI interfaces, if you don't exist somewhere an AI can find you and your work, it's much harder to be discovered. Building in public or maintaining some public presence ensures AI systems can surface you.

Check your employment contract and stay safe

Before building side income streams, review your employment contract for non-competes, disclose side work if required, and don't burn your day job chasing side projects. Be smart and don't do anything sketchy.

Notable quotes

Being the AI person is relative. It just means that inside of your circle, you know more than the other people. — Nate Herk
Your name is signed to it. Whether that is something really good or something bad, you will take the blame. — Nate Herk
The people who win in the AI era aren't the ones building the fanciest agents, they're the ones building systems that run quietly in the background, costing almost nothing, and doing real work. — Nate Herk

Action items

  • Pick one main AI tool (like Claude) and commit to using it for real work, not just experimentation, until you deliver measurable ROI.
  • Identify one recurring task in your current job and use AI to automate or accelerate it; document the before/after time and results.
  • Create a project or custom GPT with real context from your work (documents, past examples, calendars, data) instead of opening blank chats.
  • Build a library of great work in your field; save examples and analyze what makes them good, then feed corrections back into your AI instructions.
  • Audit your weekly tasks and identify predictable triggers (specific emails, time-based events, CRM actions) that could be automated.
  • For each automation, ask: Does this need AI or could a simple workflow do it? Does the system need to fire on its own or do I trigger it?
  • Start building in public: experiment with AI, share small projects, document wins and losses, and make yourself discoverable.
  • Define one business metric for each automation (tickets resolved, appointments set, refund rate) and build until you hit it, then move to maintenance mode.

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