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What I’ve Learned Answering Questions for 20 Years

Two decades? Wow.

It was 20 years ago today I started having something to say.
Midjourney generated "20 year service award"
(Image: Midjourney)

Today marks the 20th anniversary of Ask Leo!. On August 10, 2003, I posted the first answer: How Do I Keep the Status Bar from Disappearing in Internet Explorer 6?

Much has changed in the intervening years. Some things have stayed the same.

I’ve also learned a lot in that time. I’ve learned a lot about technology, of course, but I’ve learned more about people and, of all things, philosophy. Here are some of the things I’ve learned grouped into three big baskets: people and philosophy; technology; and life in general.

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People & Philosophy

Obvious isn’t obvious.

What’s blindingly obvious to one person is often anything but to another.

Yes, it happens with technology all the time since both knowledge and experience differ so greatly. I list it here first, however, because many of the items I’ll talk about below may seem obvious to you. Some are. Some are only obvious in hindsight. And others are just as mysterious to me today as they were the day I started.

So, yeah, when something isn’t obvious to you but it seems like it is to everyone else, a) it might not be as obvious to them as you think, and b) regardless, I know how you feel.

People are lazy, and that’s ok.

Not only is it ok, it’s necessary.

Systems and solutions built to rely on people putting in extra effort, especially effort they don’t see as related to what they’re trying to do, are doomed to failure.

Let’s face it: most technological innovation since the day we started walking upright (and perhaps prior) happened because we’re trying to make things easier and do less work.

In other words: because we’re lazy. That’s OK, but it can make the additional effort often required to make technology work all the more frustrating. More on that in a sec.

People are impatient, and that’s ok too.

We’re all in a hurry. Every single  one of us.

Time is our most precious resource, whether we acknowledge it or not. We don’t want to waste it looking for an email confirmation that this login really is us, trying to decide if the pictures we’re shown really are bicycles or not, or just waiting for our device to decide that it is ready to go to work.

Again, much innovation is about saving ourselves time. We’re impatient, and it will always be thus.

People are frustrated, and that’s not surprising

Perhaps the most common emotion expressed in the questions and comments I get is frustration. Something’s not working, various remedies have been attempted, and… no luck. Or instructions are non-existent or indecipherable. Or change happened for reasons that either make no sense or simply don’t apply.

Honestly, it’s no surprise at all that technology frustrates. I think the biggest underlying cause is simply what I’ll call a bi-directional lack of understanding. Technology creators from large to small often don’t understand the user, and the average user doesn’t understand the needs and results of those creators or the basic inevitability, and even necessity, of change.

Precise terminology is a barrier to communication

I know it sounds odd. Getting the words right seems essential to communication, but technical terminology can actually be an obstacle.

The issue is that many people a) don’t know the correct terminology, b) aren’t really that interested in learning it, and c) don’t use it enough for it to stick. Much of my role becomes a glorified translator and search engine, or, if people are patient enough, a bit of a slow chat bot as we drill down identifying the specifics of the problem.

I suspect this applies to much more than just technology. Healthcare comes to mind.

Literacy matters (and it’s much worse than you think)

One of the things I encountered early on in taking written questions was the realization that many, many people can’t write. It’s more than just spelling and grammar — though that’s often appalling as well — this is more about being able to express themselves. Long rambling questions, questions that do anything but actually ask a question, questions that come close to being a loose collection of random words. You might think I’m kidding, but trust me, it can be pretty bad.

And, no I’m not talking about “text speak” or shorthand. While annoying, that’s something different. I’m also not talking about folks for whom English is a second language. Over the years I’ve become able to tell the difference between someone who clearly doesn’t speak English regularly and a so-called “native” English speaker who can’t write their way out of a paper bag.

Literacy matters. English matters. Writing well matters. It’s the one thing I’d do differently.

People want simple

This is really no surprise, but it’s at an extreme, I think, when it comes to technology, mostly because simple is so rare.

The technological solutions we have in place are so often convoluted and hidden that mere mortals simply don’t stand a chance. When things get simple, people get happier. It’s not easy because many of the things people want their technology to accomplish are complex, whether or not they realize it. The challenge is to present (or rather hide) that complexity in simple terms, interfaces, and actions that are easy to interact with.

Inertia is strong

It’s sometimes frustrating to hear from people who absolutely rail against one technology or another or one company or another… and then refuse to switch away from using that technology or company’s software. It’s a form of change aversion, I’m sure, but once people get comfortable, they become set in their ways — even when those ways irritate them deeply, and even when there are alternatives. The sad part is that some companies absolutely take advantage of this.

Change is seen as an enemy

I regularly hear from people who claim that the latest change they don’t like represents “change for change’s sake”. That’s simply not true, of course. A business changing things randomly without direction and purpose other than change itself wouldn’t last long. There’s typically a method or a madness behind the change. We may not agree with it, but that doesn’t change the fact that there’s a reason.

Of course, folks who are change-resistant suffer the most. Not only are they the most negatively impacted at a personal level by the inevitability of change, but their resistance makes it difficult to get them answers. Mired in the desire for things to be the way they used to be, offering solutions for the way things are is often ignored or outright rejected.

It’s particularly frustrating for me, as not only do I embrace change, I see it as a choice… a choice people are unwilling to make. They suffer needlessly as a result.

Empathy is everything

I’ve commented on more than one occasion that “It’s good to be a geek.” It usually happens as I breeze through some technical something-or-other that would generally stymie and frustrate non-geeks or pull together a solution that’s just not in their wheelhouse.

It also implies an opposite: “It can be frustrating not to be a geek.” Geeks need to remember this! Unfortunately, many lack the ability to do so and are often quick to ridicule. Particularly when assisting others, having empathy for what they’re going through leads to less frustration, more acceptance, and a significantly better experience for everyone involved.

Legacy is forever, even when it shouldn’t be

Bill Gates left Microsoft’s day-to-day activities in 2008. He stepped down from the chairman role in 2014 and left the board in 2020. And yet to this day people still blame him personally for every little feature they believe was implemented improperly. I find this somewhat frustrating, and yet I expect it’ll last for a long time. Unless you want to blame him for starting the company in the first place, there are a myriad of other more anonymous people deserving of your ire.

On “stupid questions”

I’ve joked in the past that I used to believe there’s no such thing as a stupid question, but then I started Ask Leo!. That’s not fair or accurate, but there are most definitely questions that make me wonder.

What I’ve decided is that most questions we think of as “stupid” are either borne out of a deep lack of knowledge (which is absolutely not the same as stupidity), or an unwillingness to do even the most basic research or reading. The “stupidest” questions I get are those clearly (and I do mean very clearly) answered on the site, or in the video, sometimes even on the very page the question is being asked.

There are definitely frustrating questions, though. It’s most frustrating when even the smallest effort would have returned the desired answer without waiting for me.


Authentication is a mess

It didn’t take long after I started for me to note that the most asked question was a variation of “Can you help me recover my lost Hotmail password?” Twenty years later: “Can you help me get back into my Gmail account?” Same problem two decades apart; only the services involved have changed (presumably based on shifts in popularity).

The underlying authentication mechanism (passwords), which seems so simple, is fundamentally fragile. Particularly when adding two-factor authentication or recovery mechanisms (beyond your mother’s maiden name and your favorite pet), the system is often so “secure” that even the rightful account holders can’t get in if even the slightest thing goes wrong.

Yes, I know, there are an assortment of alternatives and improvements and whatnot all under development, and even in the process of being deployed. Here’s the thing: it’s always been so. There have always been better, more secure alternatives, and yet we always come back to passwords. My advice: don’t forget ’em. Just don’t.

Reminders are good. Annoying, but good.

Every so often I get asked by some service or another,”Is this still your phone number?” EXCELLENT. Folks aren’t going to take the time to proactively check, so displaying a wrong number will absolutely get their attention and potentially prevent account loss in the future. (Thumbs down to prompts that say, “Would you like to update your number now or later?” while displaying a number that doesn’t need updating.)


I left Microsoft less than two years prior to starting Ask Leo!. As you can imagine, my head was full of Microsoft technologies and not much else. (Though the eight-bit experience I’d had prior to Microsoft no longer counted for much.) It didn’t take long for me to encounter and then embrace Linux, as it was the preferred hosting platform for websites and online services. There was much learned along the way. Today, not only is Ask Leo! hosted on an Ubuntu Linux server, but it’s self-managed, meaning that I handle all the nitty-gritty details. Oh, and I have another Ubuntu Linux server in my basement acting as a pseudo-NAS.

I love Linux. I really do. If it weren’t for Ask Leo!, and if it weren’t for some tools I rely on that aren’t supported (or supported properly) on Linux, it would probably be my primary operating system.


Once again, I left Microsoft mostly a PC kinda guy. (The fact that the first computer I ever owned was an Apple II also no longer counted for much.) As Ask Leo! and technology in general progressed, much of what I did day to day moved online. This meant the specific technology on my desktop mattered less and less. After becoming enamored with a specific feature in FinalCut Pro, the Mac-only video editing software, I dove in and purchased a Mac Pro, which served as my primary desktop machine for many years. I’ve now also been though a couple of Mac laptops and have an iPad as well. That Mac Pro still resides in my basement performing various backup-related roles.


People die

Specifically, readers die.

It wasn’t long after starting that one of my more active readers passed away. If I recall correctly, I got notice from a relative who’d been put in charge of their digital legacy. It’s happened multiple times since then, of course.

I suspect it’s happened much more than I realize, because I don’t get a proactive notification when someone just disappears. I don’t read unsubscribe comments (for my own mental health), and if someone’s email stops working, they’re silently removed from my lists. Over 20 years there’ve been many, I’m sure.

I think that’s something many online publishers don’t think about. To be blunt, it doesn’t directly impact their operations, so there’s no reason to. In a very cruel and brutal sense, it’s just another unsubscribe.

And yet, it’s another reflection of the underlying humanity that unites us all.

And, yes, there are certain names I miss seeing in my question queue. Sometimes I hear they’ve passed. More often than not, I just wonder.

The Future

So. 20 years.

Will I do this for another 20 years? I don’t know. I have no plans of stopping, but there are risks on the horizon.

Ask Leo! is a business, and while the past couple of years have been good, the future is definitely in serious doubt. AI-based answers directly from search results threaten to significantly reduce the number of visitors to the site. Advertising revenue is already on a serious decline — so much so I’m seriously considering stepping away from it when my contract is up in a year or so — I’m just not sure yet how to compensate for the revenue loss.

This year, for example, looks to be a net loss overall.

That’s not sustainable.

But ups and downs are the nature of online business and entrepreneurship. In fact, it’s directly related to a topic I touched on repeatedly above: change. The landscape is constantly changing, and I’ll be looking for different opportunities to keep Ask Leo! afloat.

And I do want to keep it afloat. Not only do I enjoy doing it, I see it as adding real value to people who need it most: the average computer user, befuddled by current technologies.

For whatever reason, it comes naturally to me, and I see it as both an honor and privilege, and almost an obligation, to use my skills to help others.

But I gotta pay the bills too. Smile

The good news is that I still love this stuff. I hope to keep it up for a very long time.

Whether you’ve been with me for a week, a month, or a couple of decades, I thank you for your attention and your support. I literally could not do this without you.



Podcast audio


49 comments on “What I’ve Learned Answering Questions for 20 Years”

  1. Happy AskLeo Anniversary and I thank you for your service. You have helped me over the years and I am greatful for that. I have saved a lot of your daily newsletters ( the ones that I feel could be of assistance to me down the road) to refer to if and when needed. I will be a subscriber as long as you keep putting out good info. Thanks again

  2. Happy Anniversary!

    I agree with so much of what you wrote. Having been “on the phones” at Microsoft for a little over 10-years is part of the reason why I agree with you. One of the products I supported was Word, and people who worked places that were forced to switch from WordPerfect to Word were perfect examples of people who were resistant to change and usually unable to explain what they wanted to have happen in Word.

    I have to admit that since I left there, I’ve become more resistant to change, although I’ve stuck my toes into Linux and Mac. (I’m waiting for this Windows PC to die and then I’ll most likely buy a Mac Mini to replace it.)

    I’m rambling. Sorry. I’ve enjoying reading your newsletters for years and I’ve thanked you for some help along the way. I hope you will continue to enjoy what you do for many years to come.

  3. Hi Leo, congrats on 20 years. You have helped me out tremendously,especially getting me to use Macrium reflect.
    Take care,

    • If you’ve gotten nothing more from Ask Leo! than backing up, you’ve gotten the most important advice. That’s what won me as a subscribe years before I started working for Leo. Before reading Leo’s advice in system image backups, I’d copy my data weekly to CDs and DVDs. No I do regular system image backups and daily incrementals.

  4. If I had won the lottery i would have sent 1/3 to you so you can continue as the premier go to person for technology, keep going as long as you can, there is no one like you.

  5. Happy Anniversary, I have been receiving your news for as long as I can remember. I have enjoyed your answers to my, sometimes, confusing questions. I hope you never stop, You shall always have my backing. Thank you!

  6. Rock on, Leo! I’ve been a fan and even bought you a cup of coffee back in the day. May you continue for another 20.

    I do tech support for individuals and a handful of small companies and have always said that my stock in trade is my ability to understand (and quickly research) the tech and speak plainly (as possible!), but my customers and friends tell me that it is my patience.

    I thank you for leading the way.

  7. Many thanks, Leo! Twenty years and counting. We appreciate your efforts and insights into helping us all better understand and be more comfortable in the world of technology. Keep up the good work…

  8. Leo, congratulations on a most successful twenty years. I found you about 7 or 8 years ago and have been hooked ever since – it’s a lot better than some other forms of mental enhancement…

    As to the next 20 years, at 84, I probably won’t be around to enjoy reading your various columns and advice for all of them, but one of the things that keeps me going is knowing that I can log in and check out new tips, possibly find a new class, and remember who pounded “BACK UP” into my head.

    Keep on keepin’ on.


  9. Happy anniversary and well deserved kudos from all of us who find your tips and help extremely valuable – especially when we don’t know the correct terminology

  10. Congratulations on completing your first twenty years, Leo, and all good wishes for the future.
    You have done a lot of good in that time, and we computer users owe you our gratitude for helping us along the way with your intelligent articles written in admirably clear language.
    When friends ask me about their problems, I often reply with a link to one of them.

  11. I suspect that AI will replace most things,OK,that’s expected. But, and it’s a big but, things will start to get really scary when,or if, computers are able to think for themselves! Not after a load of code is fed in,but without any instructions on what to do or how to do it – to actually think for themselves.
    This has been typed by a human being,I think!

  12. Congrats on the anniversary and thanks for the anniversary rant. Over time -I think I’ve been along for a goodly chunk of your ride – you’ve held my hand on a couple of queries and shoed me the light of Macrium Reflect (it’s so easy). Wishing you well on figuring out the next business model twist which I am convinced is with some form of sosh meda.

  13. I haven’t been reading your stuff for 20 years but well before you collaborated with others to create TEH. I am glad that you continue with the text version of your work in addition to the videos because I get more out of it.

    In regard to your legacy section on blaming Bill Gates, people should check out the Dave’s Garage YouTube channel. He points out the various things he takes blame for at Microsoft. Some pre-date windows and some have remained in Windows to the present day.

  14. Thank you Leo! Like others here, I’ve received your newsletter for about as long as I can remember (almost since you started it, I think), and I hope to continue with you for as long as you can continue doing what you do or as long as I live, whichever ends first (may it be me). This may sound a bit morbid, but its not, its selfish of me because I don’t want to go through a week without your missives, and by the way, I intend to live a very long, happy life. Even when I know/understand the topic of an item, I still read on to see if there is something new or some new angle I have not yet learned/considered. Again, I thank you for all you have done and continue to do.

    Ernie (Oldster)

  15. Thanks, Leo! You’re correct! The answer is ALWAYS in the article.. sometimes you have to look for it… I’ve kept a printer company in business printing your articles out. Thanks for your compassion, patients, and darn fine work!

  16. I found your newsletter to be very informative. I have found many answers to my questions and problems from you. I thank you.
    I have been a subscriber for over 10 years.

    Thank you,

  17. First, I find EVERYTHING you say interesting; I might not understand it, but it is interesting. It then inspires me to research and learn about what you’ve addressed.

    Most importantly, I’m thrilled you have no plans of stopping, but so frightened to learn there are risks on the horizon. I so rely on your articles and newsletters. I especially appreciate that you have often personally taken the time to answer my questions.

    I am just one, but I will continue to support your endeavor as much as I am able.

    Gefeliciteerd (?? ) :) on 20 years of outstanding, professional help and hoping for many more years.

    Thanks much, Loretta McGinn

  18. Been with you for at least 10 of those 20. So: Thank you!

    Recently after commenting on another “bonehead” move by Microsoft, you hinted at Linux. Yes, that dreaded word. If you can lead me into the swamp that is Linux and help me step away from Microsoft bit-by-bit, I will pay for that. Because you know how to explain things. You are a teacher. Not a techie who wants to show off how fast he/she can parse the decision tree. How about it, old man?

  19. First…congratulations on those 20 years. For many of us, the info provided has been virtually a godsend! Giving us your “two cents” was very enlightening and thoughtful and as a former customer service manager, you are the best at serving your customers! Certainly appreciate “bottom line” management concerns and hope you will be with us for a long time. Being 80 yrs old, don’t know if I will be around for your next 20, but thanks for the info and insight and wish you well for whatever comes!!

  20. Dear leo you are the one.
    I have lived with your email for years and learned a lot from you. Continue with this giving and spirit. Thank you so much.

  21. I will always prefer communicating with a human to communicating with a machine (AI) and I believe that could be true of most people.
    When I read your articles is not just information that is there it’s your humanity that comes through and all spontaneously. At 85 I hope to spend a few more years in your company.

  22. Hello Leo
    Although I seldom write with questions, I do support your web site. Please continue with your newsletters and advice. You have an ability to explain things in understandable language !! Thanks so much.

  23. Well Leo: It looks like the above comment is a que for a new direction for your business. Teaching about Linux! Hope that works out. I liked the thought about AI advancing to the point where computers will be able to think for themselves. That sounds fascinating. I honestly don’t know if I’ve ever thought for myself. Even admitting that I often follow a path “dancing to the beat of a different drummer” as the saying goes. lol It amazes me how ideas, beliefs, fads, memes, styles, ideas, etc. etc. etc. can travel almost a the speed of light. I have enjoyed your emails for over a decade. I need to buy your definitive solution for backup. As far as I know it is the only course I haven’t purchased. I do buy you coffee from time to time. I will see if you have an option for a shot of Irish Whiskey with that, or Kahlua, or something along those lines. I don’t drink alcohol nowadays so I figure someone should be able to enjoy it. :) (absent the nose in my stick figure smile.)

  24. Mahalo, Leo, as we say in Hawaii. Mahalo nui loa! Thank you, very much!

    I can’t tell you how much you’ve helped me for the twenty years! We used to communicate personally about my issues, but I know that’s not possible now with your increased audience, like thousand of little robins waiting with beaks outstretched for you to drop in a little worm. Yummy! I still read your articles and ask questions like a good boy: I do a search first – and, oh yes! Thanks to you, I’ve become a backup freak! My backups have saved my ass on more than one occasion! Thank you, so much, for all your help along the way, and for being a real person with us, not an impersonal chat robot or some similar real, but robotlike customer rep!

    Best you, Leo. Hope to see you around for the next twenty years. Twenty years from today I should be, oh, almost ninety-nine. It will be good. Great blessings to you, friend,


  25. Congrats and well done! I think I may have been with you from the start. Nowadays I just read and file. There are always little gems that crop up. The Bill Gates legacy is frustrating to me – as a non-American. Why oh why did we not go with CP/M – the 8 bit numerical limits built-in to MSDOS were crazy even then. And why do we still have to fight the stupid MDY date format that literally nobody else uses? And the equally stupid Letter etc. paper format. And using commas as delimiters rather than a character that is not used in normal grammar. And so many more impositions such as poor use of English grammar, incorrect spelling accepted as normal, and so on. All because of Bill Gates being American. So yes, that legacy lives on and frustrates the entire rest of the world on a daily basis.

    • I don’t think it was because BILL was American. I suspect just about any consumer software developed here would have had many if not most of the issues you mention. Both Apple and Linux, for example. The good news is that in all of them you can change most formats to whatever you like.

  26. Leo,
    Congratulations on 20 years of providing exemplary help and advice to us mere mortals who struggle with the increasing rate of change of computer technology! I cannot overstate how much your guidance has meant through that time. I hope you can find a profitable path forward for AskLeo because no AI can approach problems with the empathy and concern you obviously have.

  27. I also congratulate you on your anniversary. I also thank you for your clear answers to questions. I started using personal computers in the mid-1980’s. My first PC was a DEC! I only wish I had Ask Leo then. All I can say is keep up the good work as long as it is feasible.

  28. Leo,
    Congratulations on 20 years! Your work has helped me greatly and I really appreciate every bit of it. I’ve learned so much and I’ve greatly improved my backup and security practices. Thank you!

  29. What a wonderful thing you’ve built! I’m praying you stay around for 20 more as I just found you. Wishing you continued success.

  30. Leo!

    I have been a subscriber and before that a regular reader, and have found a lot of sensible advice in your work.

    Thank Leo, for doing what you do!

    Take care

  31. Dear Leo, thank you so much for your advice all this time. As things get more complicated, practical tips and explanations (even on new issues I don’t always understand!) have helped me expand my horizons, resolve problems, and massively reduce tech anxiety. An appreciative writer from Greece!

  32. Congratulations Leo on your 20 year anniversary of providing technical tutorials, recommendations, answers and tips to those like me who often clearly need help at times. I have been an avid consumer of your expertise for 10 years. Often I review your archive for a solution to a question that I know I had seen before.

    Thank you for your valued technical contribution which hopefully will continue for some time.

  33. Leo, thanks for all your help over the years. Many of my friends and relatives rely on me for answers to their computer problems and guess where I get them….. from Ask Leo! I’ll never be a Geek but I will admit to being an informed user of the technology. (And I know where to get the answers. ) Keep up the good work Leo.

  34. I’ve been following you online since around 2006. I’m frequently amazed at your skill in communicating complex ideas in a parlance the uninitiated can comprehend.

    While I respect the constructive attitude that ‘there is no such thing as a stupid question’ I’ve since come to believe there ARE stupid questions. Particularly when the SAME issue comes up MULTIPLE times for the same person. Evidently that person didn’t learn the first, second, third etc time that issue arose. So at least in that aspect that person is stupid to the point of willful ignorance. Fortunately that is the EXCEPTION and most people do learn, often after a few tries.

    When I worked in technical support I’d try to appease some of my co-workers hostility toward stupid questions with a reminder that many if not most of these folks suffered from ignorance, and that ignorance is a curable condition. Stupidity isn’t.

    I live your quote about ‘blindingly obvious’ things. I believe that intelligence is multifaceted and some folks that aren’t the brightest bulb in the shed in one area – say computers, may be brilliant musicians, artists or doctors. Not everyone has a knack for technology.

    You’ve got it in spades, AND the ability to communicate well. GOOD JOB!

  35. Hi Leo,
    Many congratulations on reaching 20 years! You are an absolute star and have helped me and so may others better understand and cope with the increasingly complex technological landscape.
    I totally appreciate you can not do this forever and a huge thank you for all you have done and the help you have given to less techie people like myself.
    I hope life is treating you well and continues to do so , you thoroughly deserve it.
    Please take good care of yourself and thank you so much again,

  36. Many congratulations Leo on your 20years of service.
    Relied on ‘Ask Leo’ frequently to extract me from a technical morass. You’re not getting rich from helping others but, generosity is the first of the Five Spiritual Faculties. May you continue to help us non-geeks for many more years’
    With all best wishes.

  37. I want to add my thanks, Leo.

    First my wife, and now me, after I had to take over her “IT” activities, turn to you first for geeky info.

    It is so true “What’s blindingly obvious to one person is often anything but to another.”

    I like that you, and/or your team (that is you Mark!) interact after the article is posted.

    I like that we can search, and find, many if not all answers in previous articles.

    Congrats on the first twenty years, and please keep up the good work as long as you can!

  38. I do hope you stay around for a long time, Leo. You’ve been in my inbox for years and years and I’m always learning new and important knowledge. In addition I truly enjoy YOU as a human being, a good person, caring and down to earth. In a computer world that is becoming literally more inhuman very fast I appreciate you more and more!

  39. Thank you for the handful of years I’ve been with you, and congrats to the twentieth anniversary! Celebrations!

    PS A good, reflecting text. I enjoyed reading it!


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