Sometimes I tell people about my dreams of living The Life and they ask, “Isn’t that risky?” “Don’t 99.9999% of businesses fail within the first 10 years?” “Shouldn’t you be thinking about your children’s future?” Basically they’d probably rather have me working at one of the local government contracting firms that have 3 or 4 letter acronyms that are sort of the anchors of the Washington DC Tech Economy. Not that that’s bad or anything. But it just is not that exciting.

…

Today a group of us had lunch with an old friend and co-worker, Ana. She is leaving on a trip to go sailing with her boyfriend. Around the world. Well, not exactly in a race sort of way, more of a meandering and exploring way. She just sold her condo and has some additional savings to fund her trip. Along the way, she probably won’t have much medical care, will probably face some stormy seas, has the chance of facing pirates, won’t be making much money, and worst of all (in my humble opinion), won’t have reliable internet access! Oh and did I mention that they’re planning to live with minimal expenses which means they shouldn’t have to work for at least a year, probably more?

Next to all that, saving up some money, quitting your job, and then living The Life full-time seems almost like a safe choice. At least you’ll have good internet access. ;)