Mel suggested that I write about delegation and outsourcing to virtual assistants because I approach it in a different way. I’ve read many of the same blog posts and books that she must have read, mostly written by entrepreneurs trying to squeeze as much value out of their time as possible and who want to eliminate pesky necessities like housekeeping or cooking.

I happen to like cooking. I get intrinsic value from many of the activities that people typically outsource: cooking, gardening, writing blog posts, responding to e-mail, developing websites… I also don’t mind living a small-scale life, a life where there’s room to breathe. I don’t have to do it all or have it all.

What are my reasons for delegating, then?

I want to learn how to give instructions and let go of tasks, because the feeling that I need to do everything myself will be a bottleneck if I allow it to be.

I want to get things done better than I can do them myself, taking advantage of skills that take people years to develop and experiences that I will never have.

I want to work around the limits of my attention. Sometimes I shelve projects or procrastinate tasks. Paying someone to do things not only gets those things done, it also strengthens my own commitment to move things forward.

Part of this motivation to learn how to outsource things comes from more deliberate choices about what I want to focus on and more awareness of what tends to fall to the bottom of my to-do list. In my sketchbook, there’s a page divided in two: things to say yes to and things to say no to. For example, I accept that I’m not going to invest the time into drawing realistic figures or painting work as beautiful as the ones I see hanging in the art galleries (“no” pile), and I’m going to focus instead on simple, quick drawings that capture ideas (“yes” pile).

Deciding not to try to do it all – picking some things I’m going to focus on, at least for the next year – makes it easier to choose tasks to outsource. If I want something done but I’ve chosen not to budget the time to learn how to do it well, then the real question is whether I want it strongly enough to pay someone to do it this year or whether it’s something I can postpone until I reevaluate my learning priorities. Here are the reasons why I might delegate something:

• Time premium: Is there value to having it done earlier than I can make the time to do it or learn the skills I need in order to do it?
• Skills: Can other people do it much better than I can?
• Relative advantage: Can other people complete it in less time or for less cost than I might?
• Energy: Is this something that energizes other people much more than it energizes me?
• Interruption / task switching: Can delegating this free up my attention so that I can focus on larger chunks?
• Opportunity cost: Would I be able to earn more or enjoy a different activity much more if I spent time doing that instead of this?
• Documentation and repetition: Is this a repeatable process? Is it worth investing the time in documenting the process and debugging the instructions?
• Learning: What can I learn from delegating this?

Here’s a short list of activities I’ve been thinking of delegating:

• Reminders
• Appointments
• Data entry
  • Typing in text from scans (receipts, evaluations, business cards, etc.) or sketchnotes
  • Contact information
  • Comparison-shopping
  • Transforming text
• Web research
• Text formatting
• Transcription
• Data collection and analysis
• Proofreading and editing
• Illustration
• Graphic design
• Web development
  • Web design
  • Turning sketches into mockups or HTML/CSS templates
  • HTML5/Javascript development
  • Rails development
• Setting up get-togethers with friends

I’m also interested in local assistance for:

• Occasional batch cooking, so we can try different recipes and enjoy more variety
• Cleaning
• Other chores and errands

I’ll gradually work up to delegating different activities. Gotta work on my comfort level and ability to give instructions, after all! =)

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.

Here’s the detailed feedback from one of my editors on The Shy Connector. Lots of stuff to work with here! I look forward to improving the presentation. =)

I really think the presentation is pretty awesome. Others obviously do, too, from reading the comments.  :-) I think if you left it as it is, it’d be just fine. However, I’ll write down my observations, from line-by-line editing to overall suggestions. You can then accept or implement whatever you like and ignore the rest. :-) Having not gone through and read every archived blog etc on your sites, I hope I don’t miss the mark by pointing anything out that’s already been covered in another post. And I figure that while most of the observations might seem obvious, the more you give people so the less they have to think upfront, the happier they are. And it should be presented as if going to someone who’s never read or seen anything you’ve done before. So…
My editing suggestions are more along the lines of making a transition smoother or just simplifying so the reader’s brain doesn’t have a chance to stumble. No glaring errors. :-)
Editing thoughts:
On slide #3: Add “They say:” or “I’ve heard:” before “2000 Twitter…”
Slide #4: Change “I’m an introvert.” to “But I AM an introvert.”

1. 8: Change “You’re okay.” to “You’re okay as you are.”
2. 14 & 16: add , before too: “and help you, too.”
3. 17: Change “liked” to “like” and delete “great” in “(checkout people’s great comments!)”

For the overall suggestions:
Would it be too much to add some info on WHY I need to be a shy connector? Why do I need to be able to talk to strangers? How does that help me? Who would benefit by that? Why bother? In other words, what’s the value of connecting?
You have a “How?” slide. Would some of the above points be answered with a “Why?” slide and subsequent answering slides? (Define the value of connecting and why you want to help them overcome their fears.)
What about a section on “What if I’m so shy that the ideas you suggested simply terrify me?” or “What if I try and fail miserably?” or “How can I measure if it’s working?” That sort of line of thought…
Specific points:
Slide #7: You say it took you “a while to figure that out.” I assume you meant it took awhile to figure out that you’re shy. Did you think other things were wrong with you before that revelation? Did you blame others? Have any successes despite the shyness? How DID you figure it out?  Anything you can add here that would bring others in deeper (cuz they have that in common with you)?
“Maybe I can help you or somone you know.” Can that be expanded? Some thoughts a reader might have: Do I need help? Is there something wrong with me? What can you do for me?
Slide #10: Excellent!

1. 11: I like having all the points together but it is fairly crowded. Any way to reorganize so the text fits more easily with the appropriate images? I read it a couple times before I saw the lines linking the images to the text. Afraid of messages getting lost in the crowdedness.
2. 12: Same thing here. From the layout, with the line dividing the slide into top and bottom, my eye wants to read the whole first block on top, then the second block on top,then go to the bottom. The text, however, seems to make more sense if I read the top left 1st sentence only, then the whole second block on top, then the bottom of the first block, then jump down to the bottom sections.

That is, it makes the most sense to me this way: What can you bring to a conversation? You can ask good questions that draw people out and make them think. You can recommend books and websites that help people learn. You might not be the life of the party but… you can remember (should it be “find out”?) what people need. As you learn more and as you meet more people… you’ll be able to put the pieces together.
However, the layout, I think, makes it read this way: What can you bring to a conversation? You might not be the life of the party but… You can ask good questions that draw people out and make them think. You can recommend books and websites that help people learn. You can remember what people need. As you learn more and as you meet more people… you’ll be able to put the pieces together.
It doesn’t make any LESS sense this way, I guess… just food for thought.

1. 13: Can you link somehow the first point and the sub point of that: “Write it down”? Again, eye wants to read top top, bottom, bottom. I like the green text inserted for highlights but I think that’s why my eye automatically moves to the right instead of down for the subpoint (it sees 4 blocks each with green and assumes left to right, top to  bottom).

What about inserting the “people, ideas, tools, books….” in parentheses into “The more you add [insert here], the more connections you can make”??  Only one block of text so easier on the eye and brain to put it in logical order: “The more you add (people, ideas, tools, books, links, blogs, interests, groups, patterns, notes …), the more connections you can make.”

1. 14: Excellent
2. 15: Excellent

Only thing here is should it read “the happier you’ll be!” or “the more connected you’ll be!”??

1. 16: I like the idea of the summary slide. But then the presentation “message” just ends abruptly. What about taking the last point on this slide, “share your tips and read more” with the star and links, and moving it to its own slide after thie summary?

Well, that’s it for now. I’ll keep it in the back of my head and send anything else I think of along to you. Let me know if you want me to do more or less or whatever.

Text:

I want to write better so that I can learn and share even more. I outsourced editing so that I could get an idea of what “better” looked like. The first editor couldn’t think of how to significantly improve what I sent her. Maybe I’ve hit the “good enough” gap. But improvement isn’t just about polishing something until it shines.

I can write more. If my instincts are good, then I’ll get better the more I write.

I can learn more. The more I experience, the more I can share.

I can draw more, so I can make stories even richer.

Looking forward to sharing the adventure!

Leesa Barnes is very firm about this: outsourcing social media content and relationships is not okay.

I mostly agree. oDesk and Elance job posts recruiting people to write reviews and post comments praising products or places give me the heebie-jeebies, and there’s something Really Weird about asking someone to write fan letters to people you don’t even choose. I don’t invite random strangers to connect on LinkedIn or Facebook, and I don’t leave random blog comments in an effort to build links.

On the other hand, I think that a little bit of delegation–yes, even in your personal life–can be surprisingly helpful. I really appreciate the list of upcoming birthdays and contact information that an assistant prepares for me each week, because I’m otherwise horrible at remembering birthdays, and it turns out that acknowledging people’s birthdays makes people smile. I’m glad that I have someone doublechecking the dates and times of meetings, because I’ve been burned by that before. I like being able to respond to Facebook and LinkedIn messages without having to use the Web interface.

So there’s more to this than than just outsourcing, and I wonder how much of it is related to ego. ;) I don’t get frazzled by a lot, but I do know I tend to get mildly peeved when people impolitely make me feel bad because I didn’t make them feel important enough. For example:

• When I confess that I’ve forgotten someone’s name, and that person doesn’t just gloss over it but instead further embarrasses me by dropping “obvious” hints, I’m less likely to introduce that person to anyone I know because I wouldn’t want him or her to inflict the same treatment on my friends.
• When I’ve taken a little time and effort to reach out to people, and they zing me because they don’t feel that things are personal enough, I wonder if that defeats the purpose…
• When someone gives me grief because I unfollowed them on Twitter, I can’t help but think they need to spend less time worrying about their numbers. ;)

Hmm. When I get a half-joking prod about whether or not I had a virtual assistant handle a social gesture, I may send that person a link to this blog post.

What’s important in a social gesture, anyway? Is it that someone holds all of the information about you in his or her head, or that someone cares enough to look it up or have it available? Is it that someone thinks about you all the time, or sets up ways to be reminded of you every so often? Is it that someone reads your blog and follows your tweets almost obssessively, or that someone’s willing to ask you questions about what you’re excited about and to listen to your update, and perhaps even drop by once in a while? (You can tell what I think. )

If I had someone whisper in my ear the likes, dislikes, and conversational topics related to whoever’s walking up to me, I’d love that. I can’t remember everything on my own. Knowing more allows me to be of more help. Also, it makes me less stressed about interacting with people.

If it offends someone that I don’t remember everything about them right away, or that I don’t know about the latest posts on their blog or the latest tweets they’ve shared, well–that’s probably more related to their ego. I’d be happy to let them take the initiative in the conversation. Most people forget, which is an interesting thing.

And if you find yourself having that kind of a reaction… stop and think about it for a sec, mmkay? =) Maybe you don’t need to react that way. There’s a space between stimulus and response, and you can decide how you perceive things. If you find yourself focusing too much on a perceived slight, try to move past it and focus on the good stuff instead.

Of course, other people get the same deal. If you meet me and you have no idea what I’ve recently been writing about or working on, that’s totally okay. If you say you can’t remember my name, I’ll happily reintroduce myself, no hard feelings. (In fact, if you hesitated even a little bit, I’d probably already have reintroduced myself by that point.) If you say, “Nice to meet you!” when we’ve already met, I’m never going to give you a hard time about it.

So yes, I’m fine with delegating relationship-related tasks to virtual assistants (not all, but more than most people do). I think that people can help me both be more thoughtful and learn to be more thoughtful, and I think that there’s more to building relationships than just the mechanics of social gestures.

And yes, W- knows I’m learning more about delegation, and why I’m learning about delegation, and he thinks it’s a good thing. He’s so awesome. =)

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This post was inspired by danielpatricio‘s tweet, which led me to leesabarnes’ tweet, which led me to her blog post, which tapped into something else I’d been meaning to write about because people occasionally do that “of course you should be able to remember my name” thing. =)

Now that I’m reasonably happy with managing my calendar with a combination of virtual assistance and tools like TimeBridge, I’d like to improve my talk management system. I give lots of talks, and I’d love to scale up to do even more, and to do them even more effectively.

Here are the key tasks I might be able to outsource:

• Coordinate with the event organizer on
  • date and time of talk
  • location and directions (public transit and driving; call-in numbers and web conference details if virtual)
  • size and characteristics of audience
  • organizer’s objectives
  • context of talk (previous and next activities)
  • resources available (projector, whiteboard/blackboard, easel, microphone, video recording)
  • speaker’s fee / honorarium / time and materials?
• Add a calendar event with all the details
• Get the event organizer’s emergency contact information
• Send title, abstract, bio, and picture
• Take my outline and look for stories, examples, and statistics
• Take my outline and turn it into text slides
• Add links to my pre-talk blog post
• Add photography (stock photography or Creative Commons Attribution content), with proper citation
• Confirm the date, location, and title a few days before the event
• Verbally remind me the morning of the event and send me a summary e-mail with the event details, the event organizer’s emergency contact information, the talk information, and my outline (just in case slides fail)
• Thank the organizer
• Type in speaker evaluations and contact information
• Follow up with people who attended my talk
• Coordinate with any lucky winners of giveaways
• Put my slides and recordings together (I wish…)
• Update my talk ROI spreadsheet

If I can get parts or all of this process in place, the results will be:

• I’ll worry less about getting the dates wrong
• I’ll worry less about lacking important information before a talk
• The coordination process will be smoother
• I’ll go into the talk with more confidence
• I can spend less time thinking about the details of talks and more time thinking about the fun of it
• I may be able to scale up to more than one talk per week, someday
• I’ll be able to teach other people processes for preparing for talks =)