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Climb It or Go Around It

Using AI in the job you have, and finding your way when the job is gone

This book is for people whose work is changing because of AI: people who have already lost a job, people who are worried they are next, and people who want to stay ahead. It shows the whole AI toolbox, how to set the tools up for your job, how to ask so AI understands and check what comes back, and how your own field of work is changing.

This page is the book's companion. You can download the full book free, learn the four steps the book follows, try a request for your job today, see a current list of AI tools by job, and see the Wall of Change, eighty-five years of U.S. jobs in one chart. Tools change every few months, so this is where I keep names, plans and prices up to date.

How to use this book

The book follows four letters. I call it Draw the LINE.

  • L: Learn the tools. AI is much more than a chatbot. The toolbox chapter covers twelve kinds of tools, from AI assistants and research tools to images, video, spreadsheets, apps you can build without being a programmer, and automations that connect it all.
  • I: Introduce yourself. Fifteen minutes of setup so the tools know who you are, what you do and how you like to work.
  • N: Never skip the check. How to ask so AI understands, how to check what comes back, and how to stay safe.
  • E: Expand your reach. How your field is changing, the skills every job shares, one job in depth, the new jobs taking shape, and what to do if you are already at the wall.

Under all four letters sits one rule, the Decision Line. AI does the legwork, and you make the call. Decisions about money, health and a person's mind, and every promise you make to someone, stay with you.

You do not need to read it from front to back. If you have never used AI, start with the page called Never Used AI? Start Here. Read the three chapters on getting set up, find your field, and try one thing this week. Words in square brackets, like [your job title], are for you to fill in.

You stay in charge

A request works best when it says who you are, what the task is, the material to work from, the shape of the answer and what good looks like. Then tell the AI to check with you before it starts. I rarely let an AI tool go ahead on its own. I ask it to ask me questions first, I confirm or correct its plan, and only then do I tell it to go. When I have used it enough on a certain kind of task and I know it gets it right, I let it run further on its own. Start with the check-in every time, and loosen it only when the tool has earned your trust on that kind of task.

Keep work information safe

Use the AI tool your employer approves for anything involving work information. Never paste customer or patient details, account numbers, health information, passwords, salaries or anything marked confidential into a public tool. Check every fact, name, number, date and source in the answer before it leaves your hands. If it goes out under your name, you own it.

Find your job and try one request

Pick the job closest to yours to see one request you can try today. Copy it into any AI assistant your employer allows, fill in the parts in brackets and leave out anything private. More requests for each job will be added here as the book comes together. For a fuller picture of your kind of work, see Find your field.

The check-in line keeps you in control. Add it to the end of any request: Before you start, ask me any questions you have. Then tell me in a few lines how you plan to do this, and wait for my OK.

AI tools by job

These are examples of what people in each field use today, listed so you know what to ask about. They are not endorsements. At work, the right tool is the one your employer has approved. Last checked October 2026.

Every job

General AI assistants you can type or talk to

  • ChatGPT (OpenAI), Claude (Anthropic), Gemini (Google) and Microsoft Copilot. All four have free versions that are good enough to learn on. Use them for personal learning, and keep work information out unless your employer approves them.
  • Microsoft 365 Copilot and Gemini in Google Workspace are built into the email, documents, spreadsheets and meeting tools many employers already pay for. If your company uses Microsoft or Google at work, ask whether these are turned on for you.
  • Meeting notes: Zoom AI Companion, Copilot in Teams, Gemini in Google Meet and Otter can write a summary and action list from a meeting. Tell people when a meeting is being recorded or transcribed.

Office, sales and customer service

Office assistant, executive assistant, customer service, HR, bookkeeper, sales, marketing

  • Customer service teams often find AI already built into their help desk software, such as Zendesk or Salesforce Service Cloud.
  • Sales teams: Salesforce Agentforce and HubSpot Breeze add AI to the CRM for account research, call notes and follow-up emails.
  • Bookkeepers: Intuit Assist in QuickBooks helps with invoices, reminders and reports.
  • Marketing: Canva and Adobe Express include AI tools for drafts and layouts. Check that every claim in AI-written copy is true.

Technology

Scrum master, product owner, business and systems analyst, architect, developer, tester, data, service desk, security, project and portfolio manager

  • AI coding assistants: GitHub Copilot, Claude Code and Cursor. Most teams have one approved. Ask it to show you its plan before it changes any code, and review every line before it merges.
  • Data work: Copilot in Excel, Gemini in Google Sheets and the data analysis features in ChatGPT and Claude can write formulas, clean data and explain what changed.
  • Security teams: Microsoft Security Copilot is now included in Microsoft 365 E5 plans, so many security teams already have access.
  • Project and delivery tools such as Jira, Asana and Microsoft Planner have added AI for summaries, status updates and planning.

Banking, insurance, compliance and law

Bank teller, loan processor, compliance specialist, claims adjuster, paralegal

  • Banks, lenders and insurers usually provide their own approved AI assistant for procedures and policies. Use it for anything about a real customer, and keep customer information out of public tools.
  • Legal research: CoCounsel in Westlaw (Thomson Reuters) and Protégé in Lexis+ AI (LexisNexis). Check every citation in a proper legal database before it is filed.

Healthcare and science

Nurse, radiologist, research scientist

  • Clinical documentation: Microsoft Dragon Copilot now drafts notes for nurses as well as doctors, and electronic health record systems such as Epic are adding AI charting. Only use what your hospital approves, and review every draft before you sign it.
  • Radiology tools are chosen and, where required, FDA cleared at the hospital level. Ask your department which ones are in use.
  • For keeping up with research, the general AI assistants above can summarize published papers. Check every citation, since AI tools can invent references.

Teaching

Teacher

  • Khanmigo for Teachers from Khan Academy is free for U.S. teachers and helps with lesson plans, quizzes and differentiated reading levels.
  • MagicSchool is another tool built for teachers. Follow your district's AI policy, and keep student records out of any tool it has not approved.

Trades, small business and the road

Electrician, plumber, restaurant owner, real estate agent, truck driver

  • Field service software such as Jobber, Housecall Pro and ServiceTitan now uses AI to help with quotes, scheduling and customer messages.
  • For quotes, menus, listings and customer emails, the general AI assistants above do the job for most small businesses. Check prices, codes and fair housing rules yourself.
  • Truck drivers: many fleets use AI dash cameras from providers such as Samsara and Motive. Only use voice tools when parked, or as your company's policy and the law allow.

Creative work

Designer, illustrator, writer

  • The general assistants above help with proposals, client briefs, invoices and marketing yourself. Whether to use AI in the creative work itself is your call.
  • Before uploading client work to any tool, read its terms on whether your uploads are used to train it.

Free and paid plans

Every major AI assistant has a free version, and the free versions handle reading, writing and organizing well. Many requests in the book chain several jobs together, such as reading your notes, assigning the follow-ups and putting reminders on your calendar. Steps that act inside your other apps, such as your calendar, your email or a group chat, may need a paid plan, a work account that connects those apps, or a one-time setting that links them. When a request needs one of those and you do not have it, run the first part for free and do the last step yourself.

A table for each AI assistant, showing what the free plan includes and what each paid plan adds, is coming to this page soon.

Tell me what you think

The book is free and it will keep improving. Here is what would help me most:

  1. Where did you get lost, bored or confused?
  2. Which example made you want to try something, and did you try it?
  3. When you tried a request, what happened, and which tool did you use, free or paid?
  4. What is missing for your kind of work?
  5. Would you hand this book to someone who is worried about their job? Why or why not?

Send your notes to [email protected]. Short notes are welcome, and page numbers help. Please write in the body of the email and leave out attachments.

Tell me what worked

Tried something from the book? I would like to hear what worked for you, what did not and what you would add for your job. Write to me at [email protected]. I read every message.

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