I got a new laptop from my company (OpenSpan) some time ago and as much as I'm a Mac fan, and have been using the Apple hardware for quite some time, the company's standard is Lenovo and MS-Windows.
I try to spend as much time as I can on my Mac but the new laptop is really powerful (Lenovo W510 Intel Core i7 Q720 1.60Ghz, 8GB RAM, Win7 64-bit, 500GB HD) and a huge part of my job is done on virtual machines. Well, Virtual Machines use a lot of disk space, CPU and memory. Sometimes, I also need to run two VMs at the same time which it's kind of impossible with my Mac these days. I have a MacBook Pro Intel Core 2 Duo 2.16Ghz, 4GB RAM, MacOS Snow Leopard and there is no way to upgrade memory on this machine.
So, to be able to work from my Mac on the days that I don't need to spend hours developing or testing something on my VMs but also don't loose the ability to have all of my files updated on the next day when I need or want to log in to my Windows laptop and be ready to go I found that moving to a cloud-based lifestyle would be very appropriate.
Starting with my e-mails, both personal and work related, I have all of them on stored on the server and this approach seems to be fine since I can access them from whatever device I want.
For the files that work with every day like presentations, spreadsheets, virtual machines, text files, pictures, music, etc I have upgraded my Dropbox account to the Basic one which gives me 50GB of storage and that's enough for the most important files that I need to share between the devices I need. Of course a huge clean up process was needed before I move my digital life to this approach. It has been working fine so far and I don't think I want to go back to way it was before copying files manually all over the place and sometimes having problems when I forgot to copy an important presentation to the machine I would be using next day.
Additionally, most of the applications I use every day are "cloud-friendly" and don't require any intervention to continue to work independently of the device I'm logged in to...
Here is a short list:
Note Capturing + To Do - Evernote (Mac and PC)
Instant Messaging - Adium (Mac) and Digsby (PC)
Social Networking - TweetDeck (Mac and PC), Chatter (Mac and PC)
VoiP - Skype (Mac and PC)
E-Mail, Calendar and Address Book - MS-Outlook (PC) and Mail, iCal, Address Book (Mac)
Browser - Safari (Mac) and Chrome (PC)
RSS and News Feed - Mail (Mac) and FeedDemon (PC)
Last but not least there is another important aspect to mention here about the regular backup strategy I used to have. Since Dropbox also keeps a copy of my files I have restructured my strategy to weekly backups instead just in case something really bad happens to DropBox.
If you are interested in take an approach like this, there are several resources on the web pointing you to smart uses of Dropbox and similar approaches to the one I took...
Here are some links to what I found during my research:
Lifehacker: Dropbox Syncs and Backs Up Files Between Computers Instantaneously
Use Dropbox for More Than Just File Syncing
I don't think there is a right or wrong approach but I believe the right approach is the one that works for you.
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