Ask Leo! – 14 and Counting

Today is the 14th anniversary of the very first Ask Leo! article.

I’d left Microsoft a year and a half earlier, at which point I’d joined a mastermind group of internet entrepreneurs. At the end of April in 2003 we had our first face-to-face conference, and it was within that conference that the germ of the idea that would become Ask Leo! was born.

It continues to be an interesting, and rewarding, endeavor. I’m grateful for the serendipity that lead to its creation, I’m grateful for the support – not only of that mastermind group, but of my assistants and audience as well. I’m grateful to be able to indulge my continued love of technology in a way that can occasionally help others as well.

It’s interesting to consider things that have, and have not, changed in 14 years.

That first article, for example, concerns Internet Explorer version 6 (so far this year still responsible for all of 0.0022% of Ask Leo! traffic). That puts it squarely in the days of Windows XP being the “latest new thing” from Microsoft that people were still getting used to.

Technologies change, but some things remain the same.

In fact, it’s change itself, and in particular what some see as change for the sake of change, that remains one of the most common frustrations I hear. Bugs, failures, and inexplicable “features” continue to annoy, coupled with documentation that, if it exists at all, seems targeted at anyone but the average consumer.

Malware persists, but its nature has changed. What was once more frequently the result of “script kiddies” just trying to cause havoc has turned into big business. With the increase and connectedness and complexity of our systems, so too have those with malicious intent upped their game in the form of more frequent industry-scale hacks, and the occasionally devastating malware known as ransomware.

New in both scope and awareness in recent years is awareness of personal privacy — or the seeming lack thereof — that predominates our now mostly-online activities.

And one thing that seems to have changed are “weird” questions – I don’t get nearly as many as I once did. So much so that this year there’s no annual wrap-up as there has been in years past. Perhaps some corners of the internet really are maturing. Or maybe they’ve found other, more entertaining places to waste time.

As always I am honored, humbled, and very grateful to be able to do what I do. While specifics may change to better serve my audience and keep things interesting for me, I expect Ask Leo! to be around for a long time.

13 thoughts on “Ask Leo! – 14 and Counting”

  1. Hi Leo, Over the last 5/6 years I have not only enjoyed your site but, I have learned and solved somethings from you. Your explanation of things does not get lost in technical jargon, it is made more understandable to non-techs like myself. Happy 14 and many more.

  2. Hi Leo , Happy Anniversary . And hoping for more knowledge to come . Thanks for the GREAT Teaching .

  3. Thank you for your contributions that had helped so many of us wanna be techies! I retired from network services and still love to tinker with dos commands at age 86 so am often using the Internet to help me out. Just did an in place repair of my Win 7 Pro with the help from a MS tech who was also awesome! Thanks, again!

  4. Hello Leo,
    I highly appreciate all what you are doing to help the user community, including those who by their profession
    are considered a little more advanced users.
    Your explanations are always extremely clear and valuable.

    Happy 14-th anniversary, and keep up with your excellent work for still many years further 🙂

    Thanks a lot & Best Regards,
    Iudith Mentzel

  5. Hi Leo,

    I just subscribed to your newsletter and also read this blog post. Happy 14th! I am a recent college graduate and I’ve had a love of computers ever since I was little. It’s amazing to watch technology grow over time, but like with anything you have to ALWAYS be careful and watch what you click on, post, share, and sign up for. Wishing you all the best and many more!



  6. Congratulations on 14 years! I don’t always read this newsletter immediately (but I DO read the HeroicStories as soon as I see one’s come in!)… primarily due to limited time to spend online (either limited time on my phone or having to work in the library and having shorter hours there…).
    I do look forward to catching up on the issues still in my inbox – just in case you’ve covered something that could help us (now, two months ago, or in the future) – and the new ones still to come.
    Thank you for your hard work on this.

  7. Hi Leo – happy 14th anniversary! Thanks for everything you have done to help ordinary pc users ‘out here’. Your newsletters have been of invaluable assistance over the years so keep them coming!

  8. Congratulations, I want you to know that I’ve made a folder in my email just for “Ask Leo”, lol… Thank you for your articles because they have helped me out over the last several years simply because I know just enough about computers to get in trouble every time I try something, thanks again!!!

  9. Leo, congratulations! Looking forward to many more years with you, as you have helped me through some serious thinking processes over the last six or so years! Just wanted to drop a line and tell you thanks.

  10. Better late than never. I wouldn’t miss this opportunity to wish you the very best with what your are doing, i.e., helping others. I have been reading AskLeo since its early inception. Honestly, I have learned a lot from your newsletters and I really thank you for that.

    Keep up the good work.

  11. Wow! 14, huh? That’s a while.

    I’ve enjoyed your efforts for most of those 14 years, Leo. Thanks, and keep it going. Even though, I don’t use MS Windows as a primary operating system these days, I do like to stay abreast of what goes on in that OS so as to continue to provide tech support for family and friends who still use it.

    What with the advent of much smaller and portable means to access the Internet, I wonder what the future holds for desktop/laptop computing. I see it fading as I look around. Me? Well, I’m a tinkerer, tech-geek, and gamer, so I still have the ol’ desktop system.

    The future will be interesting to see. I hope that we all get so experience a nice big chunk of it still to come. 🙂


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