Would you rather be "cool" or "productive and efficient"?

Yes, I guess it’s true!  I’m just not meant to be cool.  I tried to be cool but it just didn’t suit me!!

What follows is my diary of my move from a PC/Windows/Blackberry world to an all Apple world and eventually back.  I admit I just wanted to be cool.  I really saw no obvious reason to switch other than the rest of my family was on Mac and many of my cool friends were on the Mac, and they all seemed to love it.  I include numerous lessons learned and offer numerous bits of advice as I move you through this experience.  Mainly, I hope none of you de-connect me from your Linkedin as a result of these revelations.

This story begins around 9 months ago after I just purchased the 5th Mac and 4th iPhone for members of my family.  I absolutely love the buying experience Apple has created from the website to the physical stores, the Genius Bar and finally the packaging each Apple product comes in.  The buying experience is right out of the old Ford Model T days of “you can have it in any color you want sir as long as it’s black”.  Same now with Apple except it’s “White” not black.  I love the idea that I don’t have to make 50 or more decisions when buying the Apple product.  Compare this to the Lenovo experience where you first choose a model line, then a series, then a config category then you choose every component from a list of at least 3 options.  Yikes!!!  The Apple stores are brilliant.  You can just go down there and try everything for as long as you like with no high pressure sales tactics.  See if you can find a place to go try a Lenovo in the configuration you’re looking for.  Best Buy?  Visit and you’ll quickly see why they’re going down the tubes just behind CompUSA, Computerland and numerous others.

Once you’ve ordered the Apple product and it arrives (always on time), Wow! what an experience it is to unpack it.  Makes you really feel like you’ve bought something of grand and unique value.  Sometimes I wonder if the packing materials cost more than the device it so neatly envelopes.  From the perfect fit of the packaging, to the creative ways it all comes together and comes apart, and the elegance of the materials themselves just makes you feel so good you don’t bother to think for a minute you’ve over paid by at least 30% for the functional value of the product.  It wouldn’t surprise me to hear someday that Apple spends almost as much in R&D on the packaging as it does the products themselves.
Up to 9 months ago I had only experienced the” buying experience” and had never actually had the opportunity to use a Mac laptop or iPhone or iPad.  I assumed I had been missing out on the most exhilarating, exciting, cool and self actualizing part of the Apple experience.  The using it part…  I was feeling deprived and oh so uncool.  That’s when I decided to take matters into my own hands.  Get rid of the gray, lose 25 pounds, get into top fighting shape and go all in on a Mac, iPhone and iPad.  Ditch the PC/Windows/BB.  I was going to be cool.  In fact, I didn’t lose the Gray or the 25 pounds and I’m still not in fighting shape as I figured just carrying around the sleek white mac would trump all that stuff.

Starting with the MacBook Air it’s time for some reality…
No matter what hardware I’m running I can’t do without Outlook.  From all I could tell initially this would not be a problem since Outlook was also available on the Mac.  Once I finished the self actualizing step of unpacking my very own Mac and starting it up I proceeded to load Outlook.  Yikes!!  I barely recognized it once it was installed.  It looked nothing like the outlook I knew and loved from the PC.  After doing some digging I discovered it’s at least 2 versions behind the latest version for the PC and maybe more depending on your definition of “version”.  All components of Outlook (eMail, Calendar and contact DB) where from the stone age.  Initially I said to myself “well you didn’t think being cool was going to come for free did you?” and I soldiered on to the Outlook migration step.  Getting my Outlook data migrated over to the Mac.  Sounds simple right?  It’s all Outlook.  Wrong!  Mac requires the outlook data source files be converted into it’s proprietary format called .OLM.  I found out later that’s because it’s virtually impossible to convert from OLM to anything non Mac.  Yikes!  I won’t bore you with all the details surrounding this process but suffice it to say at least 10 hours of time was sunk into this conversion.

Is this little diversion going to detract me from becoming cool?  Hell NO!  Despite the dreadful outgoing mail performance, the horrendous email UI, the dropped fields in the contact DB and the stone age look of the calendar I’m moving on.  Next step is to simply connect the new Mac to the multi-function Printers we have hanging off the network in the house.  This should be really easy.  Right?  Standard H-P multi-function printer/scan/fax.  After numerous back and forth with H-P I got the right printer driver downloaded but when it came to the first time I needed to scan something or print double sided I was informed “the Mac software is not yet available from H-P.  Sorry sir!”  These two words are going to repeat themselves many times as this story unfolds.  Okay, so now my double sided printer/scanner can only print single sided.  I again ask myself for the sake of being cool can I live with this?  Hell yes!  On we go.

Next we decide we will swap in an XBox (yes at the request of the kids) for our old Wii (deemed no longer state of the art).  This requires me to reprogram our universal logitech AV remote control.  Should be a simple task as the settings are all stored in the cloud at Logitech and I just need to download the desktop app to my shiny new White MacBook Air, log in and make one simple change in the configuration and all should be fine.  Hmm, well not quite.  It turns out Logitech does not support it’s desktop application running on the MacBook Air.  After numerous requests to speak to “management” at Logitech they gave me access to an “unsupported” version of the desktop application that ran on an older Mac running an OS earlier than Lion.  Yes, several more hours of fiddling and I was able to get the remote updated so my head would remain attached to my body the next time someone wanted to use the XBox (which is a very useful piece of equipment for many reasons).  Again I pause to ask myself “how much do you really want to be cool?”.  Hmmm, my conviction is waning.

For brevity sake I’m going to skip the next 6-8 other experiences in the same vein and get to the punchline.  The final act that caused me to bail on the whole needing to be cool thing at the expense of getting anything done, was when my wife needed to download a set of digital pictures from her camera and then copy them to a thumb drive to take to her classroom.  If there’s any task that should be optimized for the Mac it would be something like this.  Well, have you ever tried to just select, copy and paste photos from iPhoto onto an external drive of any kind.  Between all of us we could never get it to work.  Fast forward, I as able to do this in 3 minutes on the PC.
The end of the road to Coolness!  Went out and bought a Lenovo laptop with 30% more of everything than my Air and at 65% the cost, and the new Nokia Lumia 900 with Windows Mobile.  The nightmare is now over.  I’m home at last.  I love the Windows Mobile UI.  Simple, fast and intuitive.  Everything works.  Nowhere near as many apps in the app store, but with a screen 30% larger than the iPhone and a real full featured browser there is nowhere near the requirement for Apps designed for the phone only.  I’m still discovering new unique features of the Lumia.  I was driving in the car yesterday and a text message arrived.  The phone automatically asked (verbally through the Car audio) if I wanted the message read to me and who it was from.  When I verbally responded with “read it” it translated the text to speech perfectly and asked how I would like to respond.  Wow!  Try and get your iPhone to do that!

Moral of the story:  I’m not feeling cool but I am feeling productive, efficient and back home where I belong.
I won’t even mention the cracked screens (yes, very plural), failed charger connections, failed top buttons, battery decay we’ve experienced with all our Apple products.  Despite all this everyone except me in the house still loves their Mac/iPhone.  At least I can now print, use Outlook, copy pictures from a camera straight to a thumb drive and update our TV remotes.

On a more serious note one piece of important advice:  There are essentially three consumer tech ecosystems out there.  Pick one and stick with it for everything essential.  Everything essential for people like me is PC OS, email, Calendar, contacts/connections/friends/etc., mobile device and OS, and finally the tablet.  The three ecosystems competing in the market are Microsoft, Google and Apple.  Pick one and stick to it as much as possible.  They all make claims they are “open” and connect, and play nice with the other ecosystems out there but it’s simply not true.