Taking a quick break from the usual outsourcing examples this week. I’ve been thinking lately about how our experience during the past year of Personal Outsourcing has differed from my initial expectations. As I read and talk to more people that are trying it out, I find these differences are not uncommon.

#1- I’ve used it less than I thought

Ah yes, sitting on a beach somewhere while an army of personal assistants handles every less-desirable aspect of your life. And doing it for two dollars a day, no less.

In reality, even with a great assistant and a smooth workflow, it’s easy to leave your assistant with an empty queue. And it’s not for lack of things to outsource- I got over that challenge a long time ago. The simple fact is that the more you outsource, the more outsourcing you have to manage. One key technique is to set up ongoing, repeatable tasks. Right now my assistant logs less than an hour a week doing ongoing tasks. A lot of my life is already automated, but there are plenty of routine things I still need to get off my plate.

#2- It’s more rewarding than I thought

The novelty factor in Personal Outsourcing is huge, particularly when floating your tasks overseas. It just makes you feel cool. I thought that would wear off, and it did. Despite the public nature of this site, many of my friends and colleagues have no idea that we have an assistant. Those that do know, generally only find out because I try to give some background to HTD when people ask me what I’m working on these days.

And yet, there’s still something fantastic about coming back from lunch, sitting down to my computer, and seeing an update: “made that phone call and fixed that thing.” I think to myself “instead of waiting on hold during the noon hour, I just had lunch with a friend.” Or I’ll check in on ongoing task after 3 weeks of forgetting about it, and see that it’s been successfully repeated each Friday morning as requested. It’s just nice. Using outsourcing less than I thought I would doesn’t really matter. Even a couple hours a week has a noticeable impact.

#3- I’m a demanding boss

Actually, we all are. We all have these nasty little micro-managers inside us just waiting to come out. We’re quick to justify spending a few minutes (or hours…) at work surfing the web or doing otherwise “less-productive” activities. But once the tables are turned and we’re covering the payroll, it’s easy to really scrutinize the little details of how and when work gets done, how much time it’s taking, etc. It might take a little while, but eventually you learn to let go- at least if you have a solid assistant.

Those are my big 3. Feel free to share your own surprises in the comments.