Figuring It Out

Published July 23, 2025

Hearing the word “upgrade” no longer sounds as promising as I once thought. The entire point of the word is to convey improvements. As I’m working on my sixth decade now, I have seen a lot of “upgrades” along the way. I’m still not convinced that the “New Coke” episode from April 1985 wasn’t a brilliant intentional mistake. Only 79 days later, the original was brought back and customer loyalty only went up. However, most evidence points away from someone being intentionally brilliant. What actually happened is probably people being less-than-smart (for the umpteenth time) thinking everyone wants an upgrade.

Unfortunately, most of us find ourselves having made many decisions in the past that we didn’t fully appreciate at the time. We adopt some new gizmo that is cool or super useful, only later to learn that things are more interrelated and dependent on other things than we would have ever imagined. But now it’s too late. We have integrated said gizmo into our livelihoods and lives to the point that we have a hard time seeing how we’ll ever go back.

The list of things that fit this scenario is disturbingly long. But top of that list, for most, is your personal computer. 72% of people who own personal computers use Microsoft’s Windows operating system. Of those Windows users, two-thirds are still using Windows 10. (In the United States, the percentages are slightly less, but still significant.) The problem for users and Microsoft is that Windows 10 will no longer be supported by Microsoft as of mid-October of this year. What does that mean? What should you do?

I started working on a list to help people work through this. However, as a seasoned technical consultant, the answer to questions will always be “Well, it depends.” And while that’s true, I’m going to cut to the chase and then change the entire subject!

In my opinion, about 4 or 5 people should plan on upgrading their Windows 10 to 11 sometime this fall. But that probably is only slightly helpful. The real issue is that I can’t write something here that would be helpful to every person, unless….

The reason this article is titled “Figuring It Out” is that helping everyone improve their own overall ability to figure out challenges like this could go far beyond the Windows 10-specific issue. That’s the goal from here on out, even though we’ll use the Windows upgrade as our example.

If you haven’t noticed, lots of people are talking about artificial intelligence. Few people actually say the words anymore. It’s just “AI.” And even though AI goes WAY past what I’m going to walk you through, super-smart web searching using AI tools is a practical way that many have started learning about and using AI. Let me warn you against tricking yourself into thinking these crazy smart searches are all there is. But, also, enjoy it, because it can be awesome.

The following is a pattern that I encourage you to do if you are a beginner. Go to these websites and do these exact things, and you’ll get some really solid help. There are many different systems, but I’m going to suggest two free options to get you warmed up. The two websites I recommend starting with are https://gemini.google.com/app and https://grok.com/. There are limitations on how you can use these free tools, but both will work for the following.

Go to both of these online systems separately, and please “ask” them the following question. Also, don’t forget to say ‘please’ and ‘thank you’ since, theoretically, our future AI-robot-overloads will probably remember if we were polite. I recommend that you use this exact terminology, even though you can ask them whatever you want.

“Could you please provide step-by-step instructions to help me prepare for upgrading my Windows 10 computer to Windows 11, written in simple language for someone who isn’t very tech-savvy? Additionally, please include a clear pros and cons table that outlines key factors to consider before upgrading, with detailed explanations tailored for a beginner.”

Now, review the answers from both systems. Chances are, in this case, the answers will look very similar. That is not always the case depending on how you ask and what the topic is. However, any time you spot differences, that’s something you should make note of and pursue. Otherwise, when the answers are similar, it is likely that you will do well to follow their instructions.

These answers are going to be much more thorough than what I could ever share here. And the bonus is that I recommend you try this on a myriad of other big questions you might have. Don’t be deceived. AI is perfectly capable of being wrong. But in this case, I am betting their answers will be better than anything I could create.

One last bit of reality. I promise, most of you are not going to like the answers. Lots of steps. Lots of things you probably won’t fully understand. Be strong! Read the answers. Take them one by one. Trust the process. Or just hire someone to help you out. There’s a good chance they’ll do exactly what I just told you to do in creating their own checklist. I still think most people will be better off with an upgrade if it’s possible.

And if you don’t ultimately upgrade your Windows PC, you will still have upgraded the way you figure some things out!

 

And beyond this, let’s see what’s next!

J Matt Wallace