I want to address some Outlook specific points first. Security and privacy issues aside, it is not that complicated to run multiple email accounts, calendars, and task lists in Outlook because each of these item types can be put into a unified view and worked-on in this view. No matter how great a relationship you may have with your workplace, it will eventually come to an end. Even if you own your own business, you will eventually leave that. Therefore, most Outlook users should separate these two.
2001, I went to Outlook calendar ( on a Palm pilot) “
Ah, Palm, those were the dayz. Your data is on Outlook and in your device and that was it ...
In 2001, the company I worked for ran PC desktops with Ms-Outlook on an exchange server, so there was a *.ost user file. At home, I ran Outlook on a *.pst file. The mighty PalmPilot was the only conduit I was aware between ost and pst outlook files. At the office, I’d do a one-way synch to get all my work data onto my Palm and then synch that to my home computer. The result is that my data was with me at all times in my Palm but unaccessible to my employer or anyone else. For the rarities where I had a personal activity during office hours (i.e. doctors appointment), I’d indicate that the it was a private activity.
As an Android user, I use a program called GSynch
http://fieldstonsoftware.com/software/gsyncit5/index.shtml) that synchronizes Outlook to my Gmail aps. This would be ideal for an employee in CorporateLand to be able to synch one’s work Outlook data to Gmail.
The issue here is, how does CorporateLand feels about their data being stored and transmitted over Google? Many companies forbid employees to use third party aps (like GTDOA) and clod sharing services. I can understand the cyber-security concerns such businesses have. Conversely, I understand that they don’t want to negate employees from optimizing getting-things-done in their work and in their lives! As an employee or contractor, my expectation is that I want to retain a copy of all my email and files that I work on. That company I worked at in 2001 had technically laid me off but they did not want to pay me for the last week or two I was there. Legal action ensued. This company’s position to the labour board was that I left two weeks before I actually did. As I had all of the email I had ever sent, I had hard evidence to show that their claim was false.
The best-of-both-worlds solution is for the employer to run Office365 that the employee can run on his/her own devices. The employer can pull-the-plug anytime and the employee can use the robust features of Outlook to run a full GTD methodology – a win-win for both!
I share your concerns about cloud security and I question the best course of action. The biggest privacy issue is that many entities are trying to collect data on you. Just like PalmPilot days, your smartphone is a good conduit to move data to and from your workplace Outlook but, if you have an android phone or iPhone, Google and Apple are collecting data on you. It does not help that people share way more information about themselves than they should in social networking sites like FaceBook and LinkedIn. As convenient as file share programs like drop box are, I question how secure they are. My solution is to have sensitive information on a broken, I mean, dedicated computer. The Wi-Fi is broken, so I have to plug an ethernet cable in, which I do as needed and then un-plug. I have all my passwords in an encrypted file named, “family-photgraph-index.xls” If someone attempts to steal this broken laptop, the dangling screen will deter them. If they actually want to steal it and hack into my computer, that will be the last file the look at. By the time a thief has does this, I will have changed all my passwords.)I have the date backed up to thumb drives that I move to my car every day. When I do this, I bring the old thumb drive into my house and copy it.[/QUOTE]