Got an old lady friend slash client who had one of those careers that let her manage to dodge learning how to type or use a computer. So around age eighty or so, and after having developed a moderate stage of multiple sclerosis, she decided to retain my services to get her online and communicating (after heavy encouragement on my part, wanting her entertained and talking to her friends as she would grow less and less ambulatory and more isolated).

So I got her a big monitor for her aging computer, fired up Google and such, got her an oversized trackball but because of her MS and arthritis she just couldn’t manipulate the trackball well, couldn’t even click the button without clicking the button on the other side of the wheel (I jammed a paperclip underneath that one, still not easy enough for her though). Barely had enough strength to type with her best finger. She tried so hard, determined. That can’t be fun for someone in her shape and she could only handle sessions for about fifty minutes.

We made a little progress, gained no traction after a handful of sessions. We were both getting frustrated but were still determined. Then one day she tells me she read an article in the Wall Street Journal, maybe the Times, about how great the iPad is. My first thought was virtual keyboard for this old broad, no way. Then it hit me, wait a minute, everyone who buys the iPad loves it, I’ve never read one bad thing about it, I’ve read things like “even my parents immediately got the hang of it,” I thought about the buzz factor and how she might have renewed excitement to show off to her friends that she went from zero technology to a super sophisticated device, told her that was the best idea hatched and it was her idea, not mine, and I’m the computer whiz.

Her computer was toast. Fortunately she lives a couple blocks from the flagship Apple store. But that would be too big a schlep for her anyway, too crowded and they wouldn’t sell me something like an iPad using her credit card, she was getting tired and I didn’t want this idea to lose momentum so I bought the thing using my Nexus S, AT&T registration and all.

Showed up a couple days later and she called me to get over there for an iPad session. Nice.

On my way over, all psyched up, suddenly it hit me that she lives smack in midtown Manhattan where AT&T sucks bigtime and that might ruin the experience. What do I do? I know what I’ll do – I’ll tether the iPad to my T-Mobile phone! Problem solved – at least during the lessons, I’d end up getting her a wifi router for her otherwise unused Internet connection.

Thought I’d ease her in with the New York Times app but, even though it was free, I discovered that not only do you need to fork over your credit card but you have to plug into a computer with iTunes just to install it. I figured that wasn’t some sort of technological limitation but Apple’s genius idea of getting everyone’s credit card and on iTunes armed to buy songs and apps. All right, next time show up with the iPad, get her going on Gmail. As for the credit card, this old lady had her number – even the CVC security thing – perfectly memorized. That underscored to me that it’s not too late.

old_lady_with_bong_1936x1296I took a lucky guess that Dragon NaturallySpeaking / Dictate or something like it was available for the iPad, that it would have enough muscle for it. I was right and grabbed it. Unfortunately, all it was good for was dictating onto a notepad kind of thing, not straight into emails, so in order for it to be of use to her I’d have to get her comfortable with copying and pasting which, given her health, wasn’t feasible. So I coached her into feeling that it’s okay to type very short and heavily abbreviated and misspelled emails, which worked.

I’m giving you all these details, by the way, should you happen to be close to someone like her. I’m aware this is rather tl;dr.

During our lessons I would cycle through refreshers on the NYTimes app, email, eventually the calendar (still working on that, that’s a challenge), Safari, Amazon, Google Search, Google Image Search, one of Apple’s book reading apps but that was a misfire, just going through those for several lessons to get her more confident and comfortable. By the third lesson I’d discover when turning it on that things like Safari had been opened up, that she was in fact using it and apparently not just to humor me. Fan effing tastic! Our sessions switched from fifty minutes to a hundred.

This mission has greatly elevated my appreciation and respect for Apple products. Growing up giving a batch of clients tune-up jobs for their Windows PCs, same motions every time cleaning out crap, I discovered that if I ever got tired of dealing with a difficult client who underpaid me or was otherwise unpleasant, or was really nice to me and I wanted to end her pain, all I had to do was talk them into buying a Mac (or in my mom’s case a Linux laptop if you can believe it) and the phone calls stopped. The damn things work and they continue to work. Apple did not manage to create demand for their products simply by charging too much, they really did earn the ability to overcharge by delivering over and over with exception, though they eventually corrected this, to signing exclusively with AT&T.

Just yesterday morning my uncle called me to tell me his laptop’s hard drive failed for a third time. I told him I could either replace it for him and install everything all over again – or he could see this as an opportunity to buy a Mac. Told him to ask my brother how he used to call me at least once a week to fix problems after problems with his PC. Then one day in a fit he decided to go Mac and the calls stopped. Which was great, but also a bit of a shame as my brother’s a currency trader, always busy, now we don’t see each other that much.

My uncle emailed me three hours later to report he just got one of those crazy thin Mac Air laptops. That’s great Uncle Bob – need me to “download” you a copy of Microsoft Office? Nope, he went legit that time and bought a copy. Wrong company to feel good about, I thought, but his Apple store experience just got him excited to be a good consumer. And other than installing Bittorrent, VLC and reminding him how to download his porn, I’ll bet anyone with five to one odds he doesn’t return that Mac. He’s a convert. Guaranteed.

Back to the old lady with MS, and thanks by the way for sweating my article out this far, I got a couple questions for you. She wants to print but the computer’s trash, so no printer sharing or relaying software. Are there any printers out there that somehow let you print over wifi on their own or do I have to get her a computer to serve this purpose alone? Other question, no need for one of those keyboard docks as, because of her weak fingers, she screen keyboard is actually better for her, the thing’s a little wobbly. Any dock recommendations? Any other recommendations for her to enhance the iPad time she has left on this earth? She’s old you know. Hope she doesn’t read this site yet (looking at our traffic logs I’m not exactly worried about the odds of that happening…). Thanks fellas.

Doug Simmons


  1. I always knew you were on my side, that beneath all the hate there was a glimmer of intelligence in your oversized head. Welcome to the outside of the closet.

    Not to change the subject, but “old lady friend” Simmons? Aren’t you a married man now?

  2. Heh thanks for the NYTimes paywall dodging tips link.

    I’m proud of you Doug, helping lonely old ladies cross the information superhighway like that. Let me guess, you didn’t pressure her to spring for the 32 gigger? The question is, would you have done that if Apple gave you a cut of referral sales or are you an honest man?

    But what’s with you and not being able to write a single article (I checked) without taking a shot at either Microsoft or AT&T? Ahh whatever, it’s okay. Like punch the monkey banners my mind is just starting to filter that crap out of your writing, which is good, otherwise I’d have coded up some PHP to let users conceal all your articles and paid your boss however much it took to install it. Seriously, I’ve thought about doing that multiple times.

    So, did you jailbreak it for her so she could tether and install Flash or did you manage to go stock this time?

  3. I read somewhere NYTimes is going to start charging for their content. I am not against publications charging for their content, it’s just that I’m not buyin. To many other ways to get news for free.

  4. Yeah you might feel differently if it were Fox News Print Edition…

    And one of the ways to sort of get it for free, btw, is by already being a home delivery subscriber, which makes this less unreasonable as there are a lot of those types.

    The good thing about this is that if the Times can demonstrate that such a pay model for such a publication were a viable maneuver to stay afloat in that business, that’s very valuable information to the other newspapers that are failing left and right.

    This is a wild crazy guess but I think that the Times, as far as these tricks go, won’t make too big an effort to prevent people from cheating the system. I mean, come on, how hard could that be.

    Also, this.

  5. BRYAN B: Good advice, I should do that. However I did set her up with everything I picture her wanting to use with a credit card — Amazon, Apple, Financial Times. Though she’s getting the hang of typing, banging in the credit card number for her, I picture her not doing that. But still all old timers (btw just pulled her up on wikipedia, 81 years in a few months — that compounded with her bad health, you get the idea) running around the web unchaperoned need the identity theft talk. For her, passwords once the Remember Mes on everything timeout on her.

    Remembering a credit card number at 81 and managing to dive right into a gadget like this after a life of no computers, even with an awesome escort, that’s impressive. Hope I don’t live that long because judging by how hard it is for me to remember names when meeting people, well, .. I guess it won’t be too bad as I’ll get to forget my Windows Mobile horrors. Oh, the horror.

    ktdan1: Yes, and I’m finally beginning to get comfortable enough here to come out of my shell a bit and reveal some of those sides, maybe one or two of which, like this one, you’ll find tolerable. Not to ditch the helping old ladies side I’ve unveiled here but I’m actually super awesome in general.

    Here’s a mind-effer for you: Though I’m working to correct this, I own more Microsoft stock than Google. I also managed to find a woman who can put up with me every single day. That’s some twilight zone out of left field shit for you, no?

    In contrast, this is probably not much of a mind-effer to you: I’m an ass man.

    … because people keep telling me Hey Doug, you’re an ass, man!

  6. While I applaud your actions concerning her education concerning the device, you also need to educate her about the pit falls of using her credit card online. The elderly are prime targets for the lowlifes out there.
    Anarticlel was recently posted byThreat postt about Itunesspecificallyy, it stated 40% of in-app purchases werefraudulentt
    Now I donbelieveive any of the other online services are any safer, but she needs to know about the pitfalls. Make sure she keep an eye on any accounts that require a credit card weather it is Itunes, the Wall StreJournalnal or what ever

  7. @Doug

    It’s not a matter of her using her card any more, it’s a matter of the sites which store her info being hacked and her information being changed.

  8. Yup. At first I thought Oh come on, we’re talking about Apple and Amazon, then I realized that not too long ago Apple/AT&T’s servers were significantly compromised. All the time. Even was recently compromised with, of all things, an SQL injection. Apache too, security sites…

    Man I could really live without these aye-holes whose contributions to the world include writing and unleashing things specifically that involve identity theft. Pop-ups and nuiscance-ware, that I can blame on Microsoft and write off as contributing to the anti-hacking industry and ultimately better software, but identity theft stuff I just don’t get.

    People who are capable of writing code (or just manipulating people effectively) that results in a massive botnet running around and quietly popping in some javascript into sites like this (it happened once) that install … argh .. people who do that are clearly brilliant and gifted and could easily become very successful by less evil means, ways that actually contribute utility to the world, yet they go the scumbag route.

    I think it’s a perfect storm combination of a mood disorder or something that results in insomnia with these people staying up all night working madly on their botnets when no one else is awake to go play xbox or beer pong with them and nothing good is on TV, plus a personality disorder, sociopathological, antisocial or something lighter like conduct disorder, whereby this activity checks out through their ethical filter.

    Or they just live in a shit country where even with these skills you just can’t make it without stealing.

    What a pain in the ass it is when you find out you’re a victim. Gotta deal with credit cards, maybe the government, banks, credit rating agencies — it can really put a damper on your day and it happens all the damn time. I’ve managed to avoid it (I don’t even have a credit card), my old man however could have used a few lectures along the lines of what you described as this happened to him at least twice.

    Clever sons of bitches.

  9. Actually, you can do without a credit card if you register for the App Store through “buying” a free app.

  10. HP has a free print app for use with some of their wireless DeskJets/OfficeJets. Epson has one, too.
    As far as the wobbles, I’d get one of those bedside laptop stands. Should work well.

  11. If your friend is having trouble using the trackball then you could try using a keyboard emulator to map left mouse button and trackball etc to a games controller. For example have some keys and such mapped to an xbox controller for the purpose of more easily playing steam games that don’t have native controller support. a good program to try for this is joytokey, its not very intuitive but i found it useful, just my two cents.


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