What do you do when your technology throws you for a loop? All of a sudden, what worked yesterday no longer does, and you have no idea what to do.

If we were working together on your personal technology, you could ask me for a hand. Assuming you’re not, though, how would you self-support?

I set out a simple workflow in a post I wrote nine months ago:

• Search online. Type a brief description of what happened, and search the results for anything helpful.
• Search social media, especially where people are having conversations. I find X, BlueSky, and Reddit the best sources of helpful insights.

Unfortunately, that list is incomplete because it doesn’t include artificial intelligence.

How I Broke Through My Brick Wall

While working on my laptop recently, I kept running into issue after issue. From slow download speeds to being unable to sign in to ChatGPT, I struggled through one challenge after another.

Finally, I resolved to figure out what was happening. I assumed that, because I had been using early developer beta releases of Mac OS 26, they were to blame.

So I opened ChatGPT on my phone and started a conversation:

I’m trying to sign in to ChatGPT in Brave browser and getting a password error

The AI gave me several suggestions for what could be the issue including a recommendation to sign in via a different browser.

No. Same issue in Safari

I’d already thought of that. No luck.

But I had help right at hand. When I hit another block, I took a screen shot and shared it with the AI. It analyzed what it saw, and kept tossing out new ideas.

It didn’t get frustrated. It didn’t roll its eyes. And it never suggested I enter my credit card number to extend the chat another 45 minutes.

And, when I had reached my wit’s end and popped off, it didn’t hesitate:

You’re not listening. I am unable to request a password reset. It repeatedly fails with the error message I shared. Both in Brave and in Safari.

In its response, which began with empathy – “I get it—this situation is super frustrating….” – it gave me more ideas, and one of them did the trick. Turned out I forgot I’d unintentionally left Proton VPN running.

AI didn’t know the VPN was the issue, but it helped me keep digging until I found and fixed the problem. On my own, I might still be stuck.

I shut off the VPN then realized I needed to share this with you because AI had just saved me more hours of running around in circles.

AI as a Troubleshooting Partner

AI is not the answer to all our problems. It is not a magician able to conjure brilliance out of thin air.

But seeing as how, according to a recent study, only 32% of people in the U.S. express trust in AI, I think you need to give it a second chance.

With the right mindset and approach, there is almost nothing you can’t solve with the help of AI. To make it work, though, you need to bring it in closer, make it a partner, let it see what you’re seeing, and accept the simple fact that it has access to stores of information you can’t even imagine.

The key takeaway is you should lean on AI to work through confounding technical challenges for the same reason you’d use it to generate a recipe for a delicious balsamic vinaigrette. The recipe may need to be modified, but you will have begun cooking.

Lean Into Your Tireless Companion or Me

AI should be a key tool in your personal tech toolbox to be used whenever you encounter a confounding roadblock.

And if that’s too big a leap for you to make on your own, let’s work together.

With my AI Trainer service, I’ll help you go you from neophyte to novice to next level.

• Neophyte: What’s an LLM? How does AI work?
• Novice: Build confidence: Prompt structure, handle errors. understand AI’s strengths and limits.
• Next Level: Unlock advanced skills: Custom GPTs, deep research, and choosing the right AI models for the task at hand.

We’ll identify your key goals and what you want to accomplish with AI, and then I’ll craft a path for you to reach those milestones at your pace.

Remember, whether it’s a VPN issue or something else, you don’t have to struggle alone. AI can be a part of your tech toolkit, and I can help you unlock it.

Image: Photo by Brooke Cagle on Unsplash modified by Google Gemini with prompt: I need to illustrate a blog post about using AI to solve tech issues. Modify the image here to depict an anthropomorphized robot standing behind the woman. The robot’s right hand is on her right shoulder. The robot’s left hand is making a thumb’s up gesture.