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5 Problems Everyone Has with AI (and How to Actually Fix Them)

By Jamie Williams • November 1, 2025

"I tried AI and it didn't work." Cool. Which AI? Chatgpt? Your work AI?

If you've been using AI for more than a week, you've probably hit the same walls everyone else does. Wrong tool, bad prompts, getting stuck, scared of costs, losing your work.

Here's what actually trips people up — and what to do about it.


Problem 1: You're Using the Wrong Tool

The reality: Different tools are good at different things. ChatGPT-4 is better at reasoning than 3.5. Claude is better at long documents. Perplexity is better at research with sources.

How to fix it: Match the tool to the task. Writing? ChatGPT or Claude. Research with citations? Perplexity. Code? Claude or Cursor. Quick questions? Free ChatGPT is fine.

My tool comparison chart shows you which tool for what


Problem 2: Your Prompts Are Bad

"Write me a blog post." What kind? For who? What tone? How long?

The reality: Vague prompts = vague results. AI can't read your mind.

How to fix it: Be specific. Give context. Show examples. Say what you DON'T want.

Bad: "Help me with my resume"

Good: "Review my product manager resume for an AI startup. I have 10 years experience in SaaS. Flag anything that sounds generic or doesn't show impact with metrics."

Browse my prompt library to write better prompts


Problem 3: You're Stuck Between "Total Beginner" and "Actually Building"

You've done the intro tutorials. You can chat with AI. But you don't know how to actually USE this for your work.

The reality: Most AI content is either "here's how to sign up" or "build an enterprise RAG system." Nothing in between.

How to fix it: Pick ONE thing you actually need to do (not a demo project) and figure it out with AI as you go. Need a website? Build it. Need to analyze data? Do it. The gap between beginner and builder is just doing one real thing.

My AI skills training helps you go from curious to fluent


Problem 4: You're Scared of the Bill

"What if I rack up $500 in API costs?" (Spoiler: You probably won't.)

The reality:

  • Free tiers of ChatGPT and Claude handle 90% of normal use
  • Paid plans ($20/month) give you plenty of runway
  • API costs only matter if you're building a product

How to fix it: Start with free. Upgrade to paid when you hit limits. Don't even think about API costs unless you're building something for other people to use.


Problem 5: You Keep Losing Your Work

You're mid-conversation, making progress, then... conversation limit. Everything's gone.

The reality: AI has short-term memory. Long conversations degrade. You need a system.

How to fix it:

  • Keep a running doc of important outputs
  • Start fresh conversations when things get messy
  • Use Projects feature (Claude) or Custom GPTs (ChatGPT) for ongoing work
  • Save your best prompts in a doc you can reuse

Download my context template to maintain continuity across sessions


The Real Issue

None of these problems are about AI being too complicated. They're about AI companies not telling you the obvious stuff because they assume you'll figure it out.

You don't need a course. You need someone to just tell you what actually works.

Now you know.

📝 Note: Ideas and opinions are mine, but this post may have been written with AI assistance. Please note mistakes can happen. This is for general information and entertainment purposes, not a substitute for professional advice (e.g., medical, legal, financial). Use at your own risk. Opinions expressed are my own and do not necessarily reflect the views of any organizations, employers, or affiliates I may be associated with.

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Jamie Williams

Product leader and builder at the intersection of AI, data, and culture. Based in Cincinnati. Shipping products, testing ideas, writing about tech that actually works.