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.

Photo (c) 2009 Markus Rodder – Creative Commons Attribution No Derivatives Licence 2.0

I want to become a more engaging, more thorough, and more organized writer. I want to be able to write clear and insightful essays – not high school book report essays, but discovering-life essays. I want to get good at capturing all this raw material that flows through life, and digesting them so that I and other people can learn.

Practice is essential, of course. Stephen King writes:

If you want to be a writer, you must do two things above all others: read a lot and write a lot. There’s no way around these two things that I’m aware of, no shortcuts.

I'm not looking for a shortcut. I'm looking forward to decades of figuring this out. If I remember to keep backups along the way, it will be fun to review the archives.

Deliberate practice and feedback would be good, too. A few weeks ago, I posted an oDesk listing for a personal blog editor and writing coach. I'm not particularly impressed by any of the candidates. Part of it is because I'm not yet clear on what I want.

Part of it is because what I want is different from what most people writing blogs want. I don't want to write a niche blog that rockets to the top of Google rankings and becomes a passive income stream through affiliate marketing, ads, or information products. I'm not failing with my current blog, and I'm not looking for help “fixing” it. I'm doing better than I could've imagined my notes could do. Who knew so many people would keep coming back and reading? One of these days I might discover what you like about this blog – or maybe you can tell me, and I can think about doing more of it.

Here's how I want my blog to work, in some ideal future: I've got an excellent capture workflow that encourages me to write about everything I'm learning. A subset of this is published to my blog, where interested passers-by and the occasional searcher can find (a) technical snippets that save them hours of work, or (b) reflections that make them go “hmm” or “aha”. My evil plan is that people might discover other interesting posts along the way and will look up from their browser window several minutes or hours later having learned about all sorts of things they wouldn't have thought of searching. I will settle for going through that same discovery process myself, as I find things I've forgotten writing.

How can someone help now? I want someone to read my planned posts and tell me: here you need to explain things more. Tighten this up. Take this out and put it into another post because you're trying to do too much. Get rid of “nice” and use a real word.

But more than this surface-level editing, I want logical editing. What's your point here? It doesn't make sense. That argument doesn't support your conclusion, so get rid of it. That's a fallacy there. Let's work on that metaphor. If you reorganize it like this, everything falls into place.

And then I want meta help: on how to ask interesting questions that lead to exploration, how to capture as much learning as possible, and how to organize all of that so I can make sense of it later. Like Lion Kimbro's How to make a complete map of every thought you think, except maybe less rigorous and more technologically-assisted. I want to be able to work with an archive spanning years and years.

I could edit myself. I have old entries I'm no longer attached to, and future ones that I can examine closely. I keep looking for ways to improve my system. I can just throw a lot of time and effort at it, and become much better in a decade or two.

It would be good to work with other people, though, who can be more ruthless. It would be great if they've spent lots of time figuring out their own workflow and system for keeping everything organized and they can tell me the pitfalls I should avoid or address.

I haven't found anyone I really want to work with. I don't think I'll find other people who are passionate about this kind of braindumping on oDesk or any other freelance site. (Particularly geeks who can also help me tweak my Emacs setup to totally rock.)

Sometimes it feels like I'm going after the fiddly bits, that last 20% that will take another 80% of effort. I'm a good-enough writer, and my notes are organized well enough. The blog is searchable, and I've got structured text files holding almost everything else. Sometimes I worry that I'm leaning towards perfectionism and indistinguishable differences. But then I read people who are better writers, and I think: I've barely begun.

No substitute for writing, reading, or living. I'm going to have to do the hard but fun work: reading interesting people and figuring out what I like about them, living, writing about life, revising, tinkering around with some kind of organizational system.

Ah, well. I guess there are some things you can't learn from books. There are some things you can't even learn from teachers.

SCHEDULED: 2010-07-23 Fri 08:00

I don't like spending money. Sometimes it's hard for me to give myself permission to experiment. I get this urge to invest it for the long term. Darn you, compounding interest. But long-term planning is better the more you understand about what you want and don't want, so experimenting now has its own payoffs.

I hesitate to delegate because of the time I think I waste doing other things. Reflecting on my week, though, it looks like I'm pretty trim about how I spend time. About the only timesuck I feel guilty about are reading fanfiction on the Internet. I'm fascinated by how well-written fics fit neatly into the original universe. It's like how well-written code fits neatly into the overall structure. But it leaves me feeling less warm and fuzzy than reading books from the library or blog posts from the Internet. Solution 1: Feel less guilty about it. Solution 2: Deepen, trim, time-bound, or eliminate it.

And then there's the realization that I can take things slowly, that I don't have to cram so much into a day, and that chores have value. So what if it takes me the better part of an evening to tidy and clean? It's good thinking time, and it also means that I know where things are. I grew up around maids, and things were constantly being put away, and I had to ask where things were. Now, I'm glad I know where most things are, and I can invest time into figuring out where things should logically be.

BUT it's good to experiment and to explore backup plans so that if life really does get all crazy-busy (interesting opportunities, life events, etc.), we can get through.

There are a few things I want to try:

• Cleaning/housekeeping
• Cooking
• Singing lessons
• Sewing lessons, and wardrobe/pattern advice

(As it turns out, I can learn the ukulele mostly on my own, it just takes practice. If a toddler can do it, so can I!)

Cate Huston’s excellent post on delegation got me thinking about outsourcing things again. I learned a lot when I experimented with virtual assistance. I concluded the experiment when I got around to automating the tasks I’d previously outsourced and I didn’t come up with new tasks.

Since then, I haven’t felt starved for time. I’ve even been able to explore new hobbies, like woodworking and ukulele. I occasionally think about hiring a housekeeping service, but a few hours of meditative tidying up gets the house back in order. There haven’t been any chores that drained my energy or happiness. I don’t have time for everything, but I have time to do things at a sustainable pace. I’m content.

Content? Ah, there’s the signal to ask myself again, “How wonderful can things be?”

I want to write a book. In the time-honoured tactic of getting out something so that I can get over the hump and work with what I’ve got, I can re-read my blog posts (21 years old – 25 years old, perhaps?), do a little bit of editing, categorizing, and cleaning up, and just get that into some kind of e-book or paper copy. It will need a lot of trimming in order to get things to a manageable size, as I wrote well over 100,000 words a year. I’m hoping most of that is ephemera. ;)

What would adding money to this do? I actually do want to reread all that stuff myself, but I might ask someone to lay it out nicely if I can’t script a good layout. Then there’s printing it as a paper book, which is useful as a backup but requires bookshelf space. I can take a course or buy books on writing memoirs to help me improve my writing, too. I can spend on experiences worth writing about, of course!

I want to enjoy great food. There’s nothing stopping me from doing this, I just have to find recipes and experiment with them. Some kind of cooking get-together would be an awesome excuse, particularly if I have other friends who want to learn how to cook. We might even do it virtually by sharing stories and recipes, although that might be less fun.

+Money: Entertain more often (once every month instead of once a quarter?). Buy better-quality ingredients and go for the more unusual recipes. Get help with the shopping, prepping, cooking, serving, or cleaning.

I want to get the hang of the ukulele. It’s fun, and it exercises my auditory side. +Money: Find an ukelele teacher (maybe one who can teach singing as well), and spend at least an hour a week working on this. A teacher can help me avoid bad habits, figure out how to transition between chords smoothly, and pick songs I’ll enjoy playing. Actually, a singing teacher would probably be good to find first, as that would make a big difference in enjoyment…

I want to take more pictures. I’m not holding out here for “better” pictures – I want to take and share more of them. +Money: An even smaller camera or a bigger beltbag (purses get in my way), or making other things in my beltbag smaller so that the camera always fits, or a separate camera case for the belt (as long as I don’t get to bat-belt level?).

I want to sew better. Clothes, accessories, etc. A private teacher can help me alter my patterns properly. Advice on which kinds of looks and patterns work for me would also be greatly appreciated – that way, I don’t spend a lot of time sewing things that won’t work for me. =) +Money: lessons, styling advice, a serger.

I want to draw more. I’ve been drawing a lot in my sketchbooks, but I miss the ability to edit , colour, and upload drawings quickly. Maybe I’ll replace my Eee with a tablet PC after I finish all of my sketchbooks. It would be great to take sketching classes, too, because I can learn a lot from exercises, feedback, and tips. +Money: Tablet PC, classes

I want to be more organized. Part of this is slowing down and paying attention, and another part is having a place for everything so that I enjoy putting things away. I don’t want to have a housekeeper do this because then I’d never be able to find things myself. <laugh> +Money: Organizers

I’m actually reasonably organized now, so I think the priority would be to get singing lessons sorted out, then check out tablet options. Hmm…

It had to happen. I’ve replaced my Timesvr assistants with a collection of Perl scripts. Delegation had been a good experiment, but I’d gotten frustrated by the number of duplicate calendar entries and the occasional library fine when people didn’t follow my instructions correctly, even with all the notes and clarifications I’d added. Also, my wake-up calls were no longer being done by happy, enthusiastic assistants, but by uncertain-sounding assistants who paused for approval all the time.

Being a resourceful programmer, I cancelled my monthly subscription and wrote code that did many of the routine tasks I’d asked them to do.

What worked well, and what can I improve?

• Delegating tasks to more skilled professionals whom I’d picked myself actually worked quite well. I dropped several people who didn’t perform as well as I’d hoped, including an illustrator who submitted tracings of other people’s photos instead of drawing something original.
  It was good to think about which tasks I could delegate and what steps were involved.
• Setting up one-time appointments worked well, but setting up recurring appointments was confusing because of Timesvr’s rotating pool of assistants. Next time, I’d probably go with having a single assistant if I want something like that.
• Being able to call in with a request was a useful substitute for having a mobile data plan and looking things up myself, but a data plan is faster. ;)

Delegation was a good experiment, but automation is even more fun. I find myself thinking in Perl rather than Ruby because Perl’s archive of modules (CPAN) is much, much bigger than Ruby’s, so practically everything I want to do can take advantage of an existing library. =)

Beyond Booked Solid: Your Business, Your Life, Your Way Its All Inside Michael Port, 2008

(This link is an Amazon affiliate link, but if you’re near a public library, take advantage of it. I borrowed this book from the Toronto Public Library. =) )

Michael Port’s follow-up to Booked Solid focuses on how to grow your business beyond yourself, and is an excellent read for people interested in taking the next step.

I’m curious about the A3 Reports he describes on pp. 61-62. The A3 Report summarizes a business situation on a single sheet of 11.7”x16.5” paper. It would be interesting to use this structure to think through personal situations as well. =) (I guess I’m weird that way.)

• Title of report, name, and related information
• Theme/objective
• Current situation analysis
• Root cause analysis
• Alternatives
• Recommendations
• Future state picture
• Implementation plan

On page 94, he also provides some tips on making things happen, and then he fleshes them out over the next pages.

• Collaborate.
• Adopt practices for exploring a variety of perspectives.
• Coordinate meticulously.
• Listen generously.
• Build relationships intentionally.
• Have clear intentions.
• Develop habits of commitment making and fulfilling.
• Tightly couple learning with action.
• Call on your talents.
• Bring your passion to the project.
• Embrace uncertainty.
• Have a compelling story for your project.

On page 146, he offers tips and outsourcing work to other firms. He firmly believes that you shouldn't outsource in a way that creates a single point of failure for your business. If you work with firms and document your systems well, you can get back up and running after unexpected difficulties.

On page 173, he makes a particularly good point relevant for public speakers. He says, “Before I give a speech, I need to be careful not to try to create a particular energy. Instead I tap into the audience's energy. We all need to tap into the energy of the people we're working with. There's only so long you can be an energetic cheerleader for a project if the people around you need to be manipulated into corresponding energetic responses. I'm sure you've all thought how your energy level rises around people who are excited about the work they're doing or, for that matter, how your energy lifts with someone who has a zest for life.”

Another good take away can be found on page 177, where he advises, “Schedule fun once a day — after your normal working schedule.” This not only helps you include your productivity by encouraging you to be more efficient, it also helps you manage your energy.

Worth reading, particularly if you’re interested in scaling up.

Delegating to virtual assistants started out as an interesting experiment in learning how to tell people what to do. In the ten months since I started, I’ve learned a lot about working with virtual assistance for personal tasks. Here’s a brief reflection that might help if you’re thinking of exploring virtual assistance yourself.

For an entrepreneur or a small business owner, delegating to virtual assistants makes perfect sense. You want to focus on revenue-generating activities, and you can’t waste your energy on tasks you don’t enjoy. But even if you’re not self-employed, you might find virtual assistance useful.

I work with different kinds of virtual assistance services. For generic skills and routine tasks, I use Timesvr, which charges USD 69 for “unlimited” 15-minute tasks (really, 6-8 tasks per day). Here are some notes:

• Setting appointments: Great. They follow up with people and manage my calendar. People’s reactions are fun, too. ;)
• Following step-by-step routines: Good. Because the task is done by any available assistant, I sometimes benefit from different perspectives, and sometimes get people who overlook a step. I’ve given my routines one-word shortcuts so that I can e-mail complex requests easily.
• Comparison shopping: Okay. It’s a good idea to specify which stores you want, and even better if you can specify the item you’re looking for. I’m in Canada, so I need to remind them to check if retailers will ship to Canada and to factor in shipping costs when comparing price.
• Web research: Hit or miss, unless the search is very specific. Maybe it’s the 15- to 30-minute “task window” they work with, or differences in approach, or even English skills. Still, it’s a decent way to get started on a task, and even wrong results teach me more about what I’m really looking for.
• Calling for information: Good. I don’t have Web access on my phone, so if I’m out and I need to confirm information that’s not on my iPod, I can call them. It’s a US call, though, so I ask them to call me back with the results. The turn-around time is decent.

I really appreciate being able to stop worrying about some things, like following up on appointments and renewing library books. I also like saving a lot of clicks when it comes to checking out multiple books from the library, saving the time it would take to log in, find the book, check it out, confirm the request, etc.

My routines include four daily tasks that probably take a total of half an hour to do, three weekly tasks that take a total of another half hour to do, and one monthly task that takes all of five minutes. This works out to around 17 hours a month, or about USD 4 per hour. Then there are the one-off tasks I assign as well, which are included in the USD 69 fee. Even when you add in currency conversion and other fees, it’s not bad. If they raised the price, I might shuffle my budget, or I’d automate more of my tasks (time to break out Perl!) and go with a dedicated assistant instead.

For specialized skills such as editing and illustration, I hire people on oDesk, mostly on an hourly basis. I post job openings, review people’s profiles and portfolios, pick several candidates, pay them for short trial runs (because spec work is not nice!), and keep track of providers I like the most. I love hiring people who are much better than I am at something, because I learn so much in the process.

Works for me. =) If you’d like to learn more about delegating to virtual assistants, leave a comment or contact me!

(Thanks to Dror Engel and Irina Patterson for the nudge to write about this!)