Prompted by my sister Ching, I’ve been thinking about delegating again. She’s looking for a virtual assistant who can help sort out the details of their move to California – research cellphone plans, set up appointments, that sort of thing. Me, I’m generally curious about programming, and delegation is taking that to a different level. At its best, delegation will even let me “program” things that I don’t know how to do. It’s like being able to write a routine like doSomethingAwesome() and take advantage of other people’s proprietary microcode!

I’m going to ease up a little on long-term investments and carvie out a chunk of my budget for learning how to get other people to get things done. Besides, with all sorts of weirdness going on in the markets, it’s probably going to heck in a handbasket anyway. ;) I’m still investing for the long-term, but I’ll redirect some of it to education. Books and classes can’t teach me how to scale up, but working with people can.

I thought about what was making me hesitate:

• Money: Although you can hire inexpensive contractors, it’s still a non-zero cost. I compare my estimated costs with eliminating the task, doing it myself, or putting it off until it makes more sense.
• Time: It often takes me less time to do a task than to write instructions and debug people’s output. I don’t feel pressured by time. The limit of 24 hours each day just means that I get to some things sooner, some things later, and some things not at all.
• Trust: There’s the obvious level of difficulty in trusting other people with passwords and financial information, but there’s also the other level of trusting them with communication on your behalf.
• Trying to figure out what to outsource: Web research is a natural candidate for outsourcing. Learning, well… the work is inside your brain.

So here’s how I’m starting to think:

Money: Yes, the cost of delegating might be more than the direct value of the time I’d save in the best case. But (a) it will help me learn how to scale beyond the hard 24-hour limit we all have, (b) it’s cheaper than an MBA, and (c) it flows money to people who appreciate the work. Looking at the job postings and people’s resumes, I feel like I want to give people much more meaningful work than spamming blogs.

Also, it’s a little embarrassing to write about delegating work. People assume you’re one of Those People with executive assistants and all of that stuff. I’m sure we can work that out.

Time: Yes, it can take more time to write instructions than to do a task. It also sometimes takes more time to write a program than to do a task, and I’ll still happily write a program anyway. This is like writing people-code. Maybe I won’t reuse instructions as much as I hope, like the way some of my scripts are ad-hoc. If I blog about them, though, people can use them as starting points.

Trust: This one’s easy: start with low-risk tasks.

What to outsource: Brainstorm lots of ideas. Plan small chunks of work so that I don’t feel self-conscious about running out of good things to delegate. Test my assumptions.

I’m starting to understand another paradigm shift I need to make: the shift from thinking about “How can I outsource what I do?” to “How can I fund what I want to get done?”

There’s something there that I didn’t know the first time around. You see, I’d been thinking about outsourcing as a way to support what I want to do, and the interesting goals are the ones where the most work happens inside me. Thinking of outsourceable tasks was difficult. I didn’t really resonate with the advice other people were giving on virtual assistance. I don’t run a business, I’m fine with work and with what I do in my free time, I actually get decent sleep… It’s not about freeing up space so that I can do what I want to do, because I’m already doing that.

Here’s a different thought: If I switch to thinking “How can I fund what I want to get done?” – to think of myself as a capitalist in the sense that I can provide the capital for a change in the world – ah, now that opens up possibilities… It’s a little like considering myself like a Kickstarter or an Awesome Foundation on a tiny tiny scale.

Going back to my sister, for example: I may not directly want to compare cellphone contracts for her, but I do want her to enjoy a smooth and not-very-stressful move. Moving halfway around the world is tough. She and her husband have moved before – from the Philippines to Singapore – but this involves a busy time (right after our other sister’s wedding), lots more timezones, a really long flight, and other things. So we can delegate tasks that would make her life better.

I would like our family stories recorded and written down. I may not have the skills of a professional interviewer or the patience of a transcriptionist, but maybe someone can help me make that happen.

I want my blogging, quantified-self-tracking, and Emacs life to be awesomer. I can dig in and code myself (balancing that with my other coding interests and with IBM), or I can sponsor improvements that help other people.

I want my blog to be more visual. =) I want my presentations transcribed. I want other people’s presentations transcribed, like my mom’s lectures and my dad’s speeches.

I want our chest freezer full of individually-packed home-cooked meals, and I want to enjoy more variety.

I want to put together more tips on happiness, and connecting for introverts, and geeking out in life, and all these things I don’t read enough about in published books or hear about enough in conversations.

Time is an obvious bottleneck, but I’m a bottleneck too. If I dream dreams that I can’t do by myself, though, then I can make more things happen. Some things resonate with people and they voluntarily take up the cause – my dad is amazing at moving people to make a difference – and some things happen faster if you compensate people for doing them. It’s a little like moving from “What do you want to do?” to “What do you want to happen?”

Let’s see where this idea takes us.