I have my first experience of working from home amid financial crisis in Nov 2008. I started a new job with Autodesk consulting division at the time, after working for my previous employer for 8+ years. My intention is to get more customer engagement experience, and also if I stayed, I would probably stay for a year or more to go through the financial crisis. So I decided to jump ship.
It was not smooth experience. I probably would not do it if I have to do it again. Couple reasons: 1) I was not familiar with the software I was supporting or consulting with, it’s a new language and new application for me; 2) I was new to working from home. Before that I did some working from home due to doctor appointment, or as integrator doing after hours work, or doing development work on thanksgiving when I am bored (I was single then). I also worked from remote office (Shanghai) for 6 months: I social with my Chinese colleagues there though. Some of the bad memory I had: I wear panamas all day, the work never stops really, from morning say 9 am until 10 pm, because the laptop was always on. There is no colleague to ask for ideas or chitchat, or have an intelligent discussion.
Financial crisis is another source of uncertainty, as the economy is basically in decline or flat for a while. Job security, project renewal etc. I think of things I can control, and things I cannot (this is something I learned from Arch Coal, esp. from David the CIO later on). I have a bit more control on my work, but absolutely no control on the market or economy. I have some control on the project, or best practice or process. At that time my sweet point is actually work from Panera bread, Borders (the book store, not gone), Barnes Noble and Starbucks (not my favorite because it’s a bit crowded). I recall seeing Frank Cusumano couple times at the Borders (maybe Bread Co too).
So slowly I gained some confidence this way, by playing my strength: developer mentality, analytical, source code version control (even for the automation design we were doing). I still switched to a regular office developer job in Feb 2010. But I think I learned some valuable WFH or remote lessons in my 15 months at Autodesk $ADSK
Also read work from home friendly companies.