When my girlfriend was applying to vet schools, we knew our relationship was going to have to be one of long distance for a pretty long stretch of time.

All of the schools she was applying to were rather far from New York (where we’re from), but the one school she was accepted to and ended up attending was undoubtedly the most interesting among them: Ross University, located on the island of St. Kitts in the West Indies.

Interesting is a bit of a loaded word. I say “interesting” because living on a small Caribbean island obviously affords a wide range of unique experiences that her other, largely Midwestern schools don’t.

But I also say “interesting” because this particular school runs on trimesters, and that means she only gets a handful of weeks out of the year to come home. Combine that with my full time job and too many different ways of stretching my few vacation days, and maintaining the relationship becomes a bit of a challenge.

Not long ago, a relationship such as this would have relied on written letters and long-distance phone calls. Even as of only a few years ago, world-flattening technologies such as broadband and VoIP were out of the question and we would still be struggling to communicate regularly.

Today, however, I write this as I sit on her porch. I will be here for twelve days, and I will not be taking a single day of vacation.

I really hate gloating. I only include this photo to help illustrate my point.

This is possible in part because technology has reached the point where telecommuting is possible in St. Kitts, but it’s also possible because my employer does a good job of managing his employees.

There are two primary components to this:

1. My employer trusts me.
2. He doesn’t have to. I fill out time records which are tied directly to our projects and billing, so if I’m not pulling my weight it becomes obvious rather quickly.

As you might expect, this works out rather nicely for my particular situation.

This kind of freedom doesn’t come without its trade-offs, however; my pay and vacation time for example are less than what I could get elsewhere by a sizable margin.

You won’t see me jumping ship, however. I have no intention of trading my freedom for more money, especially with my girlfriend abroad and a coworking community to maintain. I’ve committed myself to putting my lifestyle first.

That’s my situation. What’s yours? What would you be willing to trade for more autonomy? If you could do the work you’re doing right now, but from anywhere with an internet connection, would you do it for less money? How much less? What if it meant you could work on side projects and potentially open up other revenue streams? Employers: how might your business improve if you trusted your employees, let them work from wherever they wanted most of the time, and tracked them with measurable metrics?

Do you think you’d get better production from them? And less turnover?

Do you think they’d be motivated to do well so they don’t risk losing their sweet gig?

The answers to the above will vary, of course, based on the industries and work involved. But for a growing number of people, I think the potential responses to the above questions are becoming increasingly… interesting.

-Tony Bacigalupo