Pursuing the ULTIMATE in Flexible Work Hours

I have this friend from college who’s never quite been fond of following the rules.  (For some reason, I’ve always been fascinated by people like that.)  When his parents sent him from Milan to Boston for college with a tuition check, he cashed it and bought a small building.  By day he’d go to school, and by night he’d do construction work on his new place.  Soon it was filled with tenants paying rent, while he was sleeping on a piece of drop cloth on the floor of the basement.

But he had a plan.  Achieving independence was at the top of the list.  Learning English, second.  Finishing his degree (to make his father happy) was third.  Instead of just focusing on getting through undergrad, he wanted more of a challenge still, so he enrolled in the Business/Engineering program, then tacked on an MBA to seal the deal and officially check off the “get a great education in the US” box for his family.
He tried to play by the rules for a little big and pursue a prestigious career.  But it was short lived.

He went to work as an investment banker in New York City, donning a suit every day, and trying to comply with the laundry list of rules, regulations, expectations, and structure.  He soon grew weary and swore off suits.  From there he went on to start up an internet technology company, in more comfortable clothing, on his own schedule and in full control of his environment.  Despite the mounting success, he continued to grow frustrated with corporate life, then business in general and yearned for more flexibility at work.  In fact, he craved a situation where he didn’t necessarily have to work.  The ultimate in flexibility, right?  Pipedream?  Even I thought so, but yet again, he made the absurd happen.

We lost touch for a few years, but I recently got to reconnect and see him in the flesh during my mileage run to Brazil last year.  In case you’re like me and occasionally fantasize about running off to a remote corner of the world when life gets overwhelming, well, here’s someone who actually did.  Long story short (yes, I know, this is where it really gets juicy!), but now my friend lives a few months at a time in a handful of remote places, works for a few weeks at a time when he needs to or is inspired, keeps no schedule, refuses to wear a watch, reports to no one, and is in complete control of his life and bliss.

Post a comment below and I’ll share more details of this fascinating tale.

Jennifer Kushell is the President & Co-Founder of YSN.com. On twitter Jennifer is known as @YSNJen, and you can read more of her articles on the YSN blog HERE.

Photo via epicharmus, on flickr. “1 Wall street and Empire Building” Published October 3, 2007.