Moving, kicking and screaming, to the cloud

Cloud computing has matured a lot and many folks like Kevin are happily working in the cloud and loving it.  I have not moved to cloud computing so far but that is going to change.  I’m not sure I’m ready for it but I will soon find out and since many are contemplating the same move I’ll share what I find along the way.

Why am I moving to the cloud?  I may have seemed opposed to working in the cloud but I’m really not.  Like many I do have concerns about all of my stuff being in the cloud, especially regarding accessibility when connectivity is not available.  The thought of being cut off totally from my email and PIM information for a time is unsettling to say the least.  But I have to admit that I have followed Kevin’s process closely and I can state with certainty that he’s quite happy working in the cloud.  I have to admit that if I need advice or help along the way it’s a pretty nice advantage having someone around who has already done it so if I’m ever going to be ready to move to the cloud then it might as well be now.

You have to understand that I’m not doing this just because I want to, no, necessity is the driver here as is often the case.  Now that we are happy members in the GigaOM family we have the usual corporate amenities such as email accounts.  There is no question that GigaOM is one of the leading experts in cloud computing so it’s no surprise that the corporate email is based on GMail.  It’s a very nice system as anyone who uses GMail can attest so adopting it into my working system is a no-brainer.

Maybe that’s not a good term as I have what is already a fairly complicated working system and adding the GigaOM email to it will require some planning and thought.  I already had an Exchange Server setup for my old business needs and will continue to have that for a good while.  I might need access to information sometime and it can’t just go away.  On top of the Exchange Server system I also have the jkontherun email account which is a POP email system that I’ve used for almost five years.  It can’t just go away immediately either although I have to be ready for the time when it will.  I also have a GMail POP account I use for some things but not as much as the other two accounts. 

I have used Outlook on the Windows side and Entourage on the Mac side to work with these email accounts to date.  This system has worked pretty well for me as it gives me a common interface for all email, POP and Exchange, and also insures that all my mail is duly archived and backed up on the Server side.  It also means that I can get to all of my email from any notebook, handheld and cell phone I might be using at the time no matter the connectivity.  They all work with Exchange so my stuff is easily in sync across the board.  While this system has worked well I have recently grown weary of the differences in Entourage and Outlook as they have begun to complicate things given their differences.  Nothing major but they are different enough that I have considered dropping Entourage from the Mac and just going with the native Mac apps.  They all work with Exchange now so I can still work on the Mac side without Entourage.  I’ll give up some functionality but not much and I think it will make my life easier, and my main justification for a given technology is that it must make it easier for me to do something in particular.

Now that I am adding another email address I know that things will get even more complicated.  I will now have two GMail accounts, one POP account and the Exchange account.  Unless I make some changes I will have the four email accounts on three different email platforms, Outlook and Entourage on two different computing platforms.  Then throw in my cell phones, the iPhone and the BlackBerry I still use, and things get very complicated indeed.  Should I use the two GMail accounts in the web browser on separate tabs and just leave them open all the time?  Should I set up the GigaOM GMail account in Outlook AND Entourage in addition to the others?  Do I forward some email to other accounts and if so which ones and to where?  See how quickly this gets very complicated indeed.  I am currently working through all of this so more later as I become less paralyzed with fear of the move to the cloud.