I’m not the first one to be thinking about outsourcing some of my business tasks and personal chores, and my situation is by no means unique. But it occurred to me that if I kept track of my experiences, it might provide some helpful advice to anyone else thinking of doing the same thing.

It was my wife who first suggested to me, a few months ago, that I should consider getting an offshore “personal assistant” to help me with various work-related chores that take up far too much time, provide little or no intellectual benefit or financial compensation, and could be easily offloaded to anyone with an Internet connection. I thought it was a sufficiently interesting idea that I added it to my “undated” to-do list — along with a few dozen other vague, ambiguous projects that I may or may not ever get around to (“Climb Mt. Kilimanjaro before the snow melts from the peak”, “Visit South Pole while there still is a South Pole,” “Write Great American novel before people forget how to read,” and “Swim the English channel before it becomes so polluted that you have to walk all the way” have been on the list for years). But I had no idea where I would find such an offshore personal assistant, nor how I would go about setting up a working relationship … so the idea languished, and was destined to suffer the same feat as my Kilimanjaro project.

But then I started reading Timothy Ferriss‘ The 4-hour Workweek on my Kindle machine last week, and I found some of the specifics I needed, plus a bunch of straightforward, common-sense suggestions on how to get started. Thus far, I’ve contacted two Indian firms, asking for a price/schedule proposal on three relatively simple, modest projects; and I’ve got a list of more ambitious projects that I’ll consider outsourcing once I see how these first ones go. I’m also going to try a few other “suppliers” of outsourcing work, including one in Mexico and perhaps one in Canada; it can’t hurt to get some real-world experience with a few of them before I decide which one to continue working with.

At this point, I’m not going to give you the names of the firms I’ve contacted, for two reasons: first, you should get your own copy of The 4-hour Workweek, so that Ferriss gets a small royalty for the intellectual effort he has expended. But more important, I don’t know whether either of the first two that I’m contacting will turn out to be worth recommending. Indeed, the first one has not responded at all in the 24 hours since I sent my first enquiry; I didn’t expect a full-blown proposal that quickly, but I thought they would at least acknowledge having gotten my message.

What sort of things have I chosen as initial outsourcing projects? Here they are:

• I’d like to get some market research indicating the percentage of automobiles, worldwide, currently being built with onboard GPS navigation systems. Having just gotten such a navigation-equipped car for the first time about a year ago, and having finally figured out how to use the damn thing, I am enjoying what David Brooks called “The Outsourced Brain,” in a delightful Oct 26, 2007 New York Times op-ed piece. I want to write a blog article about the experience of no longer having to know, in advance, how to get from A to B in my automobile; but I’d like that market research data first.
• I want to get a fairly comprehensive list of all the Web 2.0 conferences being scheduled anywhere in the world during 2008.
• Because I’m a somewhat fanatical amateur (digital) photographer, I want to get a list of all the classes and seminars about digital photography in the metropolitan New York area in the 2008 — but not the product-specific classes that teach you a hundred obscure features in Adobe Photoshop, or a hundred advanced tricks with the Nikon D80.

Could I have done any of these tasks myself? Of course! Indeed, at least one of them — if not all of them — might have been easier to carry out myself, rather than outsourcing it to someone on the other side of the world. But the whole point of these first three projects is just to see how it works, on a project that’s small enough that it won’t waste much money even if they do screw it up.

If it works, then I’ve got several larger, more ambitious projects I’d like to consider outsourcing — things that require a reasonable amount of intelligence, experience, and “Internet literacy,” but which will be a bargain if I can get it done for five, ten, or even twenty dollars an hour.While none of these projects will make me instantaneously rich and famous, I think they may give me a competitive differentiation in today’s “noisy” world, where it gets increasingly difficult to get anyone to pay attention to you (unless you’re willing to do something illegal and/or obscene, which I’m not interested in). So I’m not going to describe the details of these ambitious projects … until after I’ve carried them out, if I turn out to be lucky enough to do so.

One of the outsourcing services I’ve contacted also takes on “personal” tasks, in addition to the more traditional business tasks. I don’t feel any pressing need for this kind of outsourcing at the moment, but again it’s something I feel I should experiment with. The project that I’m thinking of, as my initial experiment, is to contract with an outsourcer to send Christmas cards to everyone on my address list; but I think I should probably “scrub” that list first, to make sure I don’t send Christmas cards to competitors, enemies, people I don’t really know, and obnoxious people I never want to hear from again. And it may be too late for such a project; if nothing else, it will be a good test of just how far in advance such projects do need to be planned.

Interestingly, several of the most annoying things on my to-do list — like sorting through the piles of papers, magazines, and irrelevant documents in my office in order to pare things down to a less cluttered environment — are not things that I can easily outsource. Sure, I could track down a local freelancer — maybe a hungry college student — to tackle some of the tasks; but I’m more interested in pursuing offshore outsourcing at the moment, and that requires activities and tasks that can be carried out via the Internet.

Perhaps the most important thing that has occurred to me is that while there may be some incremental value to having a less-expensive person tackle some of the items that are already on my to-do list, the real value is probably associated with using outsourced intellect/labor to take on the projects that are not on the to-do list. Indeed, the “ambitious” projects I’m hoping to assign after my initial learning experience are things that never would have gotten onto my to-do list — because I instinctively knew that (a) I didn’t have anywhere near enough time or energy to do myself, and (b) it would have cost a small fortune (or a large fortune) to hire someone in the U.S. to perform the task.

Having said all of this, I’m also well aware of the overhead, communication problems, and other risks that have been reported about offshore outsourcing in the business environment these past several years. But there are obviously some companies that have figured out how to overcome those problems, and from my frequent travels to India, I know that an enormous amount of software development work has shifted overseas (just as I predicted would happen, somewhat prematurely, in my 1992 book Decline and Fall of the American Programmer). And if big companies like IBM and Microsoft (and a few thousand others) can figure out how to make it work, then maybe I can too.

In any case, stay tuned. I’ll let you know how it works out…