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Your Biggest Struggles: 2024 Edition

So many struggles

I asked what was bugging you. Here's what you told me.
An illustration in a modern digital art style depicting the mythical figure Sisyphus struggling to push a giant boulder up a steep hill. The boulder prominently features the Windows logo, symbolizing the challenges of dealing with Windows operating systems. The scene is set in an ancient Greek environment with a clear sky in the background. The emphasis is on the struggle and determination of Sisyphus, capturing the essence of the myth in a contemporary technological context.
(Image: DALL-E 3)

In December of 2023 I asked my newsletter subscribers:

Question: What’s the biggest thing you’re struggling with, with respect to your technology?

I received many responses, many more than I could respond to individually.

Reading through them, there were most definitely themes. I asked ChatGPT to help me summarize what those were.

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Top concerns

I asked “What were the top 5 concerns?


The top five concerns summarized from the responses are:

  1. Difficulties with Windows 10 and 11: Users expressed challenges in transitioning from Windows 7 to newer versions, including issues with safety, compatibility, and adapting to the new interfaces and features.
  2. Complexity and Changes in Microsoft Office Applications: Many users find Microsoft Office applications like Outlook, Word, and Excel complex, especially with frequent updates and changes that make it hard to keep up if not used regularly.
  3. Rapid Pace of Technological Change: Keeping up with the speed of technological advancements and changes is a significant challenge for many, making it hard to stay current with new software and hardware.
  4. Problems with Cloud-Based Software and Storage: Concerns about using cloud storage, particularly with Microsoft’s push towards cloud services, include difficulties in finding files and managing data across devices.
  5. Issues with Device Features and Usability: Struggles include using features of new devices (like touchscreens), understanding and utilizing the full range of functionalities in modern devices, and adapting to different operating systems and user interfaces.

These concerns highlight common difficulties experienced by users in adapting to new technologies and software updates, managing data across devices and platforms, and navigating the complexities of modern digital tools.


That’s pretty close to the list I would have created had I been asked to guess before even asking the question.

If there’s one meta-theme in the top 5, and indeed in all the responses (summarized below), the most common struggle involved change. The rapid pace, specific changes, and of course questioning the need for change at all.

Naturally the transition to Windows 11 remains perhaps the most common concern.

What ChatGPT summarized as “Problems with Cloud-Based Software and Storage” is really just one word: OneDrive. A lot has happened in the last few months with respect to OneDrive, and it’s no surprise it’s a common theme.


I asked “The question was “what’s your biggest struggle with respect to technology”. Please summarize these responses” followed by pasting the entire text of all the response I received.


The summarized struggles with technology based on the responses are:

  1. Transition difficulties from Windows 7 to Windows 10, including concerns about safety and cloud storage.
  2. Frustration with the complexity and frequent changes in Microsoft Office applications.
  3. Challenges with the rapid pace of technological change and keeping up-to-date.
  4. Difficulty in choosing the best software for specific tasks, like recording music from YouTube.
  5. Struggles with using features of new devices, such as a touch screen on an HP laptop.
  6. Issues with cloud-based software, especially QuickBooks, and its updates.
  7. Overload of different apps for various services.
  8. Concerns about monetization strategies in tech companies affecting product quality and user experience.
  9. Resistance to using a cell phone and difficulties with clean installation of Windows.
  10. Dilemmas about purchasing Office 365 and dealing with Windows 11 compatibility issues.
  11. Challenges in discovering and utilizing the full range of features in modern devices.
  12. Decisions about upgrading computer components versus buying a new PC.
  13. Problems with default file formats in applications and troubleshooting scanner issues.
  14. Keeping up with the pace of technology after many years in the IT industry.
  15. Chronic issues like 100% System Disk Utilization and problems with OneDrive.
  16. Deciding when to install Windows updates and frustrations with unwanted changes by Microsoft.
  17. Difficulties in adapting to Apple devices after being a long-time PC user.
  18. Questions about transferring files between different operating systems and hardware.
  19. Struggles with merging multiple online accounts into a single one.
  20. Learning new technologies like Google Calendar and handling Windows 11’s interface.
  21. Maintaining computers and understanding the best practices for their upkeep.
  22. Confusion over Bluetooth connectivity and reliability in various devices.
  23. Concerns about data privacy and the practices of software companies.
  24. Challenges in keeping folders synchronized across multiple devices.
  25. Frustrations with the cost and features of Norton antivirus.
  26. Difficulties in understanding and using password managers.
  27. Struggles with customer support and explaining technology concepts to clients.
  28. Hesitation to upgrade from Windows 7 to newer versions due to perceived complexities.
  29. Issues with software updates and managing photos across multiple devices and platforms.


That’s a long list. Some of the items represent a single response, others represent items mentioned multiple times in different ways. But it’s most definitely an interesting list.

What next?

First, thank you to everyone who replied with their concerns. As I said I can’t respond to all of them, but I’ll be prioritizing much of my work this year based on the lists you see above. Depending on your specific concern, you may find a direct response in the coming months.

A word about ChatGPT

Using ChatGPT for this was a bit of an experiment. While asking it for facts is a risky proposition, asking it to work on something explicitly provided to it — like a collection of survey responses — is something it does well. I’ll say that it did a better job of summarizing than I would have, and in significantly less time.

Ultimately it turned a large collection of various writing styles, grammar, and spelling into something I can use.

A reminder that I generally do not use ChatGPT to write articles for me. I’ll use it to summarize and perhaps give me some ideas, but the net result is always something I end up writing, or editing heavily, myself. In those cases where I actually do simply copy/paste an AI response, I’ll credit it, as I’ve done above.

Do this

This can often help with some of those struggles: Subscribe to Confident Computing! Less frustration and more confidence, solutions, answers, and tips in your inbox every week.

3 comments on “Your Biggest Struggles: 2024 Edition”

  1. 1. Your summary is a good one.
    2. I don’t think you should apologize for using ChatGPT. The means toward the goal is insignificant. The result is what counts.


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