Since February 17, 2012 (the beginning of my experiment with self-directed work):

• 1,976 hours spent earning by working on other people's stuff – time I want to buy back
• 300 hours delegated through oDesk
• $50 spent delegating outside oDesk (so let's say that's ~4 hours)
• 87 hours managing delegation (started tracking in October) – includes interviewing, documenting processes, giving feedback

I was at a 1 hour managed : 4 hours worked ratio when I started, but I've been spending a lot more time documenting processes and training people. It's now at about 1:3.5. I think it will be worth it later on.

One of the questions I ask in order to push myself to delegate more is:

If I had spent the last two years focused on making my own things happen instead of working on interesting client projects part-time, what should I have accomplished already?

Similarly: What outcomes do I want to work on? If I work on other things, how can I fill in the gaps? For example, a visual guide to Emacs is eminently doable in two years of focused work. Ditto a more organized blog posts, lots of packaged PDFs and e-books, maybe even a paper book or two – and there are projects beyond those, and even more beyond those. I can't do much to affect my lifespan, but I can learn how to make up for those hours.

Things I'm learning

I like this system of adding lots of tasks to my Trello board and leaving it up to my assistants to choose the tasks and workload they want. That way, I don't have to feel guilty about underloading or overloading people, and they can choose things they're interested in. I'm experimenting with different ways to share resources, too – Dropbox, Google Drive, Trello attachments…

I'm building up a respectable process library. There are, of course, small bugs in the instructions I write (sigh!), but every run makes things better. Feel free to build on what I've shared.

This week, I trusted someone with my Google account, and the world did not end. This is promising.

Things to improve

I want to make sure there are plenty of tasks in the pipeline so that people can build up their skills and fill up their workload. It's a little challenging because I have to think and plan. The more types of tasks I identify and document, the easier it is to recognize delegation opportunities.

This probably means I need to make sure my assistants know how to read the due dates and filter Trello for tasks they're interested in (task assigned!). Maybe at some point I'll consider moving to something more structured. I remember liking Redmine. Hmm, it might be interesting to get stats on the kinds of tasks that end up languishing in the list and why. If I get this working smoothly, I should have just enough backlog to accommodate bursts of work, so I shouldn't have a really long list. Hmm…

I want to fill in more process gaps so that things move towards completion. I don't want to be the bottleneck. There's little point in delegating a task if I'm going to sit on the results. I want to prioritize tasks whose deliverables don't require a lot of extra work from me. It may mean writing tasks so that their outcomes can be published and shared easily (working out loud), and keeping track of what additional work can be done to push it forward. I really like the way that the podcast process has gotten condensed to just “Post show notes,” although transcripts are still a separate step at the moment. I'd like to get to that level of abstraction with other processes, while still being able to break it down into lower levels of abstraction in case I'm training an assistant with less experience.

On a related note, I want to show the big pictures for skill building. I want my assistants to be able to confidently justify higher rates for me and other employers. Oh! Maybe I can draw those process maps and find out where my assistants are in terms of skills. They can tell me what they're interested in, and we can map out sequences of tasks to help them grow. This helps me grow, too.

2014-02-27 Thinking of tasks I can assign to J- to help her build her skills #delegation

2014-02-26 Thinking about delegation and projects #delegation

• Slant my tasks towards publishing. Share intermediate results, keep track of the next steps and the big goals.
• Show the big picture in terms of processes and skills. Fill in the gaps.

Getting the hang of this!

Start by working with reputable contractors, and look for personal recommendations if you can. No matter how good the initial interview is, it's a good idea to trust people gradually and to limit the risk from misunderstandings or malice. Part of learning how to work together is building your trust in your new assistant's skills and ethics.

Break your tasks down into smaller tasks that people can do with limited access to your information. For example, if you're delegating tasks related to updating website, you might ask people to take a look at specific pages and e-mail you text that you can copy and paste into your website. If they do a good job and you feel good about working with them, you might give them access to the website so that they can edit the pages themselves.

Here's another example. I wanted to delegate parts of my podcasting process, but I didn't want to give people access to my blog or my Google account right away. So I started with typing and transcripts. When that worked out smoothly, I moved to extracting and uploading the MP3. That was fine, so I gave my assistant access to my blog, and now I can just ask him to post show notes and stuff happens. I still haven't given any assistant access to my Google account, but maybe someday.

2014-01-17 Mapping a strategy for outsourcing podcast work

Think about the smaller tasks that make up your process. Try delegating the low-risk tasks first. Plan how you can create a sequence of tasks that starts with clear instructions and limited access. As you become more comfortable with your assistant and with delegation, you can assign larger chunks of tasks, until you get to the point where they have access to everything they need.

2013-11-27 Trust and assistants

Here are some ways to help you come up with a sequence of tasks:

• Think about the accounts you have and the risk involved in sharing them.
• Write the tasks down on index cards, sticky notes, or a piece of paper. Index cards and sticky notes are easier to move around, but you can draw arrows on a piece of paper if that's what you have handy. Note which accounts are needed, and move the tasks until you come up with a good sequence.
• You can also create a spreadsheet that has tasks as rows and accounts as columns. Mark the accounts that each task needs, and sort the tasks accordingly.

Make sure you use a password manager like LastPass or KeePass when sharing accounts, so you're not e-mailing passwords around. I use LastPass to share account information with assistants. LastPass also lets me share a password without giving it, and to review who has access to the accounts I've shared. It's not bulletproof, but it adds a little security.

What about guarding against mistakes or intentional actions? Think about ways you can limit people's access to only the things they really need to complete the task. While e-mail is not a particularly efficient way to collaborate, it's one way of limiting people's access to your files and keeping a history at the same time.  Just e-mail them the information they need to work on, and ask them to e-mail you back.

Tools can help you give more specific access to your accounts or files. For example, you may not want to share your Twitter account because people can use Twitter to log on to many other services, not just twitter.com. However, you can use something like HootSuite, Buffer, or GrabInbox to give other people a separate login that they can use to post stuff as you without knowing your Twitter password. Google Drive allows you to share specific folders or documents with people, and you can give them viewing or editing privileges. Dropbox lets you share specific folders, too.

Limiting your accounts can help you trust people with them, too. For example, you might create a separate account just for your assistant, and give that account less access than you have. Alternatively, you can create an admin account and remove the administrative privileges from your account.

Backups can go a long way to make it easier for you to trust people with access to your accounts, since you know that you can recover your data in case people make mistakes or intentionally delete files. To guard against people modifying files maliciously (such as encrypting the data or replacing it with an incorrect copy), be sure to keep older versions of the files, not just the latest one. Dropbox has the ability to restore older versions of a file or undelete files, so you may find that handy. Google Drive can also keep older versions of files, and only the owner of a file can delete it.

Logs can also help you make sure assistants are doing only what they're supposed to be doing. While logs are not fool-proof, they can help you catch suspicious activity. For example, you might regularly review your Google account history to see if people have logged in from locations you didn't expect.

If you delegate, there's always a chance that someone's going to break your trust by accident or by design. Still, there are ways you can build that trust in people's skills and ethics, and that's important if you're going to trust wisely. Good luck!

Is the fear of wasting time with mistakes keeping you from delegating? Worried you'll spend more time explaining or fixing than getting stuff done? It’s hard to trust other people, and it’s easy to get frustrated when people don’t get what you mean. While it may seem that good help is hard to find, maybe seeing mistakes in a different perspective can help you get over this challenge.

I know what it’s like. I tend to assume that my instructions are clear, even though I know people can’t read my mind.  I tend to assume that my instructions are clear, even though I know people can’t read my mind. Even when you work with good people, people aren’t always going to know what you expect from them. Yes, the first few tasks are going to be frustrating, but hang in there. You could have a great team. Don’t let those initial frustrations get in your way.

A mistake isn’t wasted if you squeeze everything you can learn from it. We learn more from our mistakes than we do from our successes. Remember: you’re learning about managing people at the same time that they’re learning to work with you! Let me tell you a story about the first task I gave a new assistant.

You see, I’ve been curious about how delegation can help with my writing and sharing. I recently hired a writer through oDesk. I wanted her to help me go through a transcript and pull out good Q&A opportunities for follow-up blog posts. That way, good ideas didn’t just languish in hour-long podcasts or long documents. I interviewed one of the candidates on Skype, and by the end of it, we were both excited by the possibilities.

I thought I sent my new assistant a link to the document that already had the transcript that another assistant prepared. I expected the task to take 30 minutes, maybe one hour at most. It’s a good thing I checked on her using oDesk’s automatic screenshots. I realized that instead of pulling Q&A from my existing transcript, she transcribed the audio file I sent. Uh oh. She had spent five hours doing the wrong task.

One of the things about being a good manager is deciding that yes, the buck stops with you. I wondered where I’d gone wrong. Were my instructions unclear? Did something get lost in transmission? I talked to her to clarify what had happened. It turned out that she didn’t see the Trello card with my instructions, only the folder with the audio file. I hadn’t made sure she knew where to look for her current task. I hadn’t confirmed that she understood my verbal instructions, which turned out to be ambiguous.You might think that this would have been a complete waste of time and money, but it wasn’t.

You might think that this would have been a complete waste of time and money. It wasn’t. It was a great opportunity for both of us to learn more about delegation. Yes, we spent an hour together as I outlined my goals and made sure she understood where we were going to begin. There was a lot of information packed into that hour-long session. While she thought she knew what I expected of her, I never asked what she thought her task. She told me later that she had been looking forward to starting the project. But moving had tired her out and all the new information overwhelmed her. We both assumed we knew.

Mistakes happen, and there’s always more than one reason. (The Swiss cheese model of errors is an amusing visual.) It’s good to ask lots of “Why?” questions to find the root causes so that you can do better next time. Every mistake points out several opportunities to grow. For example, next time I hire someone and give them their first task, I’m going to make sure I send them a direct link to the instructions. I’ll ask them to explain what they will do. I’ll check in with new assistants, perhaps staying on the line with them as they do the task for the first time. (Google Hangouts, Skype, and other screen-sharing programs make this easy.)

My new assistant offered to take that time off the record so that I didn’t have to pay for it, but I told her to keep it on. After all, the work that she did was useful too. I rarely assign duplicate work, but having that second copy makes it easier for me to see the differences between the way people do things. And hey, it’s no big deal in the long run, which brings me to the second reason why mistakes are great and you shouldn’t be afraid of them.

Mistakes give you a chance to be a good manager. Contractors deal with many uncaring clients who blame them for all the mistakes that happen. Here’s your chance to be different, and to build a closer connection with someone whom you might come to trust even more. Take a thoughtful approach to solving problems and helping people move on. You might find it easier to engage and keep people who will bring more of themselves to the work. You can pay for grudging compliance with tasks and specifications. You need a special connection for creativity and initiative. A mistake is a good opportunity to connect as a human being. If it’s your mistake, ‘fess up. If it’s the other person’s mistake, be understanding. In both cases, be human.

What about situations where you keep getting the wrong results? Maybe there’s a mismatch of skills or expectations. I recently ended a contract with another assistant who couldn’t deliver what I was looking for at the time. Sometimes it’s just not the right fit. If you like people and they have other skills you need, see if you can work around their weaknesses and play to their strengths. If they’d be better suited to other teams or other kinds of work, then it’s good for everyone to move on. Think about how you'll change your processes for interview, onboarding, or probation. You can get the benefits of that mistake too.

Don’t let the fear of making mistakes stop you from delegating. There’s so much to learn from them. Think of your inevitable mistakes as the tuition you’ll pay to learn how to tap other people’s skills. Good luck!

Author's note: In fact, I asked Amanda Bassett to draft this blog post (based on an outline I gave her) as her second task. She more than made up for the flub with the first task. =) I revised her draft in real-time while she watched and added comments (hooray Google Docs!). I think that editing process will be a good blog post to share too. Learning as we go! – Sacha

The LEGO Movie rocks. This post may contain minor spoilers, although I don't think I give any of the big secrets away. =)

Many people need instructions, and many people who don’t need instructions can’t stand instructions. Regular people want to have somebody tell them what to do. Artists can’t stand having other people tell them what to do, and also struggle with telling other people what to do. Then there are people who might be able to combine both. They can create something unconventional. They can also tap the systems and processes needed to make that happen.

2014-02-11 The LEGO Movie – Reflections on Master Builders

Watching The LEGO Movie made me think about master builders. In the movie, master builders can see parts and build crazy contraptions to adapt to changing situations. It didn't matter if the part belonged to a different system. You could imagine unconventional ways to use these parts, and you could adapt your plans as the situation changes. You don’t hesitate, you build, and you inspire other people to make things. Maybe this is a metaphor for what I want to be able to do.

I want to be able to deal without having instructions and also be able to give instructions or take instructions. I want to have that ability to be creative, but also to have that ability to channel that creativity in ways that make it scale beyond me. I think that’s what Emmet (the hero in The LEGO Movie) becomes: this person who both works inside the system and outside the system.

Using The LEGO Movie as a source for metaphors makes it easier for me to identify specific skills I want to develop and plan how I can learn. For example:

• See the parts and know how they can fit together: How do you learn this with regular LEGO? Practice. How do you do this with life? Also practice. Using other people’s instructions lets me take advantage of their experience. I can familiarize myself with the “parts” that I can work with. Research and reflection make it easier for me to recognize and name those parts.
• See unconventional possibilities: You can boost your creativity through exercises. Free association, forced association, and breaking things down into their components can help. I can practice this by asking uncommon questions and exploring unusual approaches.
• Quickly adapt as things change: Don’t build for yesterday, build for today (and a little bit of tomorrow, if possible). Don’t get stuck in the past.
• Act, and inspire others to act: Yes, reflect and plan, but also act and learn. If necessary, act first, adjust later.

I’m comfortable with systems because of my experience with software development. Computers are nothing but instructions. You try to figure out how to express what you want in specific enough terms that the computer can understand and do them. I enjoy that. I find it to be a lot of fun to write programs that get the computer to do what I want. I get a lot of enjoyment out of writing and testing instructions as well. I’m curious about applying ideas from this structured world of computer programming to business. For example, what can programming paradigms help me understand about delegation?

2014-02-10 Delegation as programming

When you’re delegating, you might show what you want and say, “This is what I this is what I’m looking for; please make something like it.” This is like programming by example. You might give detailed step-by-step instructions, and that’s like assembly or low-level programming. You might work at a higher level, writing instructions that refer to other instructions for more details. That’s like procedural programming.

But there are so many other different types of programming! For example, functional programming treats the instructions as a thing you can work with. Maybe there's a way I can get people to improve or work with the instructions. Functional programming also tends to involve list processing. Maybe you do things in batches, and you think about how you can prepare the output so that you can use it as the input for something else.

Object-oriented programming is about thinking about the objects those processes belong to. Can you keep the information together so that you can see an overview? How can you use the idea of polymorphism? Maybe you might have a common process that handles several different types of objects.

Here’s how I’ve been thinking about applying object-oriented programming to the way I delegate. I’ve gotten most of my podcast/show process worked out. The next step might be to structure more of the work involved in following up after conversations. I can also work on getting a visual overview of the objects I’m working with and what state they’re in. Afterwards, I’ll look into the processes around packaging info, and then I might fill in the gaps for posts and then for sketches.

2014-02-10 Thinking about object-oriented programming and delegation

Back to programming paradigms. If you’re building up a virtual team, parallel programming might be useful. Parallel programming deals with synchronization and communication issues. It might be worth accepting a little less intra-process efficiency to improve communication efficiency.

Declarative programming might be the end-goal of delegation. You just say what you want, and people will figure out how to make it happen: what steps the team needs to take and in what order, and so on. Wouldn’t that be awesome?

I want to get better at taking these ideas about systems and using them to learn more about how to create things. Like Emmet, my first ideas are going to be crappy. I think that learning to work with and without instructions is going to be interesting. I’m looking forward to learning how to become a Master Builder. Who’s with me? What can help you become a Master Builder of life?

The other week, I focused on exploring ideas and becoming my own client. Last week, I focused on the systems I can set up in order to keep on sharing while I'm distracted by work or other needs. The other week felt happier and more self-directed, but on reflection, last week is great for long-term learning and growth as well. I just have to keep tweaking the balance. Some weeks might be more exploratory, and some weeks might be more focused on packaging things and building processes. I'll probably spend more time on consultinfg going forward than I thought I would two weeks ago, but I can see the benefits of investing the extra income into building up my delegation skills and experimenting with business ideas. (Besides, my clients are nice, and I want to help them do well.)

2014-02-07 Adjusting the balance

Thinking about this balance reminded me of this conversation that I had with Ramon Williamson, who has been thinking about the differences between artists and entrepreneurs. He's coming to terms with the fact that he wants to focus on just speaking and coaching, and he doesn't want to deal with a lot of the other small things that are part of building a business. It's like the way my dad focused on just photography while my mom took care of running the company. Ramon is looking for someone who can manage him. I think a lot of people are like that, even the ones who have been self-employed for a while. That's why partnerships often make sense, and why people often struggle with self-employment or self-directed learning.

I think of entrepreneurship as learning how to build processes, then systems, then businesses. It turns out  actually enjoy doing this. I stayed up until 1 AM Sunday morning interviewing an applicant for a writing gig that I posted on oDesk. She seems fine, so I hired her and walked her through what I'm looking for. I'm excited about the possibilities. I briefly thought of agreeing to experiment with managing Ramon and using that as practice for developing my systems, but I've committed to doing public work that builds up my life brick by brick. So I'm going to invest in building up my processes and skills, but I'm going to do that with my own content. That will also encourage me to develop my “artist” side: writing, drawing, coding, sharing, and so on.

Does it always have to be a partnership between an artist and an entrepreneur, or can you do a decent job at both? It seems like artists need to partner with entrepreneurs, but entrepreneurs with artistic bents can sometimes pull things off on their own. I think it makes sense for me to focus on developing those entrepreneurship-related skills first. It might mean growing slowly as an artist, but I think processes can scale up art so much. For example, becoming really comfortable with delegation will allow me to imagine things that I can't do on my own. This seems to be something that lots of people struggle with. Most people I talk to have issues with trust, perfectionism, and other barriers. That means that it probably doesn't take that much effort to get good enough to distinguish yourself, so if I can get to that level, that would speed up my growth even more.

2014-02-08 Artists and entrepreneurs

People's interests and skills are unevenly distributed. In some areas, it takes a lot of effort to get good enough. In some areas, a little effort goes a long way. It reminds me a little of how one strategy for playing role-playing games is to be a munchkin: to maximize your strengths and minimize your weaknesses in a way that allows you to exploit the rules of the game. While that can lead to games that aren't particularly enjoyable (unless you're playing a game that makes fun of munchkinry), in life, a little of that strategy might be interesting. So, in the areas where I have unfair advantages–and in particular, unusual combinations of unfair advantages–I might be able to recognize opportunities for uncommon contributions.

This enjoyment of building processes and systems is one such unfair advantage. Coding is another, and delegation is almost like a people-version of coding. Frugality lets me take advantage of compounding interest. Reflective learning helps me take advantage of figurative compounding interest, which is enhanced by speed-reading my way through other people's experiences and insights. Satisficing and optimism allow me to avoid the dangers of perfectionism and make it easier for me to experiment and trust. Self-direction lets me use these advantages to my own ends instead of being limited by someone else's imagination or by a job description.

2014-02-08 Unfair advantages

It is a handy combination of advantages. You should be out there, Ramon said. Joining the ranks of infopreneurs (many of whom seem to make their money by telling other people how to be infopreneurs). Making things happen. Living the life. I'm a little meh about the idea. I'll grow at my own rate and at my own time. Plus, I like the free-and-pay-what-you-want model so much more than the buy-my-training-course-for-$X-hundred-dollars. I like the way it engages generosity and acts from abundance, both on my side (here is a gift!) and on other people's. (Here is some totally optional appreciation! Make more stuff like this.) I'll either figure out how to make that work, or I'll eventually come around to setting prices. In the meantime, I can focus on building up those unfair advantages at the same time that I'm building up the things I want to make with them.

For example: delegation. I like framing my work as something that people can flexibly do more or less of, depending on their schedules and energies. It's the same freedom I have with consulting, and I think it makes it easier for people who work for me as well. So it's not a fixed “You must work 20 hours a week” thing, but rather, “Here's a board with all the different tasks waiting for someone to work on them. Pick something you want to work on. You can work more hours on the weeks when you want to, and you can work fewer hours on the weeks that you need to. Just tell me if you need to be away for a while, so I can make sure that work gets reassigned.” I'll check in with my virtual assistants to see if this is working for them or if they need deadlines or set times for focus and motivation. Eventually I might work up to asking for consistent time slots so that I have an idea of turn around times, but the system seems to be working so far.

I've been adding more people to my virtual team. There's a range of rates (anywhere from $2-12/hour), and I'm working on gradually getting more of my assistants to deserve and totally justify higher rates. I proactively give them bonuses and raises, even. Instead of micromanaging who works on what in order to maximize cost-efficiency (approach A: different people for different skills; see diagram below), I'm experimenting with putting all the tasks on Trello and letting people choose from the tasks based on their skills and energy. If I've got good enough rapport with the team, then people might focus on the stuff that really justifies the value in their rate. I want to get to the point where people are generally cross-trained, so people can take the task and see it through end-to-end (approach D). I remember from Toyota's lean method that this makes work better (versus the assembly line, where you only see your small part).

I'm also working on chunking higher-level tasks – the delegation equivalent of going up a level of abstraction, writing procedures that call other procedures. (See my list of processes) For example, I started with separate tasks to extract the MP3, add metadata, upload to archive.org, transcribe the audio, etc. Now I'm testing the task of posting show notes, which includes all of those. Maybe someday I'll get to object-oriented programming!

2014-02-08 Delegation and task efficiency

I started by mostly working on my podcasting flow, but I'm also experimenting with delegating other processes to support learning or sharing. For example, how can delegation support my drawing? My process is pretty efficient at the moment (aside from some cross-referencing data entry that I don't usually get around to doing myself), but if I batch things up more, maybe other people can help me tag my sketches and turn them into posts.

Writing is another good candidate, too. Podcasting and drawing help with writing, so it all comes together. I want to get even better at pulling stuff out of my head and out of other people's heads, and getting those ideas into a form that other people can easily learn from. That's why I'm experimenting with getting writers to help me pull out ideas from Q&As in transcripts and from all these thinking-out-loud self-reflections that may be a little too long and rambling for most people to make the most of. For example, a reader-focused tips post based on this might just focus on building systems and omit the role-playing games references. The end goal for that one would be to have a blog that mixes shorter, focused tips with long behind-the-scenes notes, and to have e-books (and maybe even physical books!) that flow well. That way, it's good for people who just want a burst of inspiration so that they can get on with applying the ideas to their life, and it's also good for people who like seeing the verbose tracing messages as I think and learn.

It's a bit strange investing so much in the processes and output without yet building up the kind of audience and demand that justifies it, but I think it's the Right Thing to Do to have transcripts and follow-up blog posts and all that jazz. If I grow sustainably and keep an eye on my finances, I'll probably get to that take-off point right when I have the skills and systems to support it – and more importantly, the community. I figure it's much easier to build great relationships with confederates/tribe people (Hi!) and provide useful resources for searchers while I'm not distracted by the mainstream yet, and I might not even bother with going mainstream. I'm just going to focus on you, and maybe you'll find it so awesome that you'll bring in a few people for whom this is also a really good fit.

That seems to be the general pattern of how I'm learning about entrepreneurship. I'm investing in the capabilities now rather than waiting for demand to completely drive it – almost like my own little MBA. Still cheaper than $80k+ for an MBA at Rotman, and you'll get better value out of my “class projects” (like this free PDF/EPUB/MOBI of my No Excuses Guide to Blogging guide). At some point, we'll figure out a proper business model. Maybe it's sponsorship. Maybe it's pay what you want. Maybe it's membership, although we'll need to find something that doesn't involve just exclusive access to content, since I like making ideas as widely spread as possible. Maybe more of a coaching program? If you want me to sell to you, tell me how you want me to sell to you. (Comment, tweet, or e-mail me!)

2013-11-17 Should I sell to people more – If so, how would you like that

(Although to be fair, there's probably a lot of demand already out there. People have been asking me for an Emacs book for years. Look! I've started drawing maps and other Emacs tips. It will happen. I just need to sit down and share more raw material. This means you need to sit down and ask me questions about stuff I'm taking for granted.)

Maybe it's a weird sort of entrepreneurship that I'm growing into, but I think it will be fun. How can I use what I'm learning to help you?

I waffle about whether I should scale back consulting and focus on making my own things, or if I should keep on consulting because the team clearly needs my help. Mostly I lean towards doing my own thing. Life is short. Although you can buy someone else's time, you can't actually buy yours. But actually it would be good for me to learn how to build processes and systems that will do the work that I want to do even if I don't always have large blocks of good focused time. The time commitments of consulting and the mental distraction of other projects are great constraints to learn how to work around.

I want to figure out how to make sure that the things I would work on during core time still happen even if I'm not focused on them. Mostly I want to get better at packaging what I know, learning more from people, and learning more on my own. I'm really happy with the virtual assistant team that I've been putting together, and we're going through my backlog of tasks at a steady clip. As I get used to delegation, I'm sure I'll figure out a coherent process for pulling it all together, making sure that none of the effort is wasted because of my inattention.

2014-02-04 What systems do I need to put into place to do awesome

What would wild success look like? I imagine that even if I spend some of the time thinking about other people's work, I'd have enough notes and background processes that I could pick things up again easily when I come back to focus on my own work. It would be amazing to get that packaging and publishing process all sorted out, and the podcasting process too. For example, I might answer someone's question in email or a Google Helpout. If I can capture that and send it through the process, maybe I'll get a nicely formatted other-people-focused blog post at the end of it. Likewise, I might start with a series of sketches reflecting on a question I'm curious about. I can record a short video segment talking my way through the sketches, and then someone else could take that reflection, write it up as a blog post, and then translate it into tips that are useful for other people–another blog post.

2014-02-04 Thinking about idea development and possible blogging flow

I don't want to delegate the core parts of sharing, but there are lots of non-unique things that I can gradually chip away through delegation or automation. If I can set up those systems to make it easier for me to get stuff out of my head and into multiple forms that other people can use easily, I think that might be worth the investment of time and money. Who knows? Maybe other people will find the processes useful too.

2014-02-02 A path for learning to delegate or outsource

If you've been reading about my experiments in delegation and you're curious about joining me on this adventure, maybe the path I've sketched above can help you get started. There are lots of small, well-defined tasks that you can easily outsource on micro-outsourcing sites like Fiverr.com. When you're comfortable doing that, you might want to find an agency so that you can assign a number of tasks without having to hire specific people each time, and you might even move up to having your own assistant or team. I'd love to help you get to the point where you're experimenting with it yourself. Then I can learn interesting things from the way you delegate and the processes that you have. Leave a comment with your questions or thoughts, or e-mail me at sacha@sachachua.com .

Committing to delegating 2,000+ hours turned out to be the key to blasting through those conflicting thoughts about delegation. I don't have to think about whether or not I'm going to delegate. I have a box of 30-40 hours a week for a little over a year, and I want to fill it with as many good tasks as possible. It's actually pretty easy to find things to delegate when I'm not arguing with myself about whether delegation is worth it. I've set up a backlog of tasks for people to work on while I document other processes.

2014-01-27 Finding tasks to delegate

It's easier to figure out what I need to do if I imagine what awesomeness looks like. What would it be like if I were fluent at delegation? I'd have a process library with detailed instructions. That would be useful for assistants, but also for me (process improvement) and for sharing with other people who are curious about delegation. I'd also feel confident about choosing people and helping them grow, and I would have a consistent stream of work so that my assistants don't have to worry about my sudden disappearance. We would track the status of these tasks so that important things don't fall through the cracks. I'd be good at sharing my vision so that they could see the bigger picture. I would be confident about the return on investment, and I'd have a safety net for mistakes.

2014-01-20 If I were a master of delegation

More specifically, what would this 2,000+ hour experiment look like if it succeeded? What would encourage me to continue delegating beyond the parameters I've set for it, beyond the budget I've carved out? Self-funding is the obvious answer: if I use this assistance to create resources that I wouldn't otherwise have, and people value these resources and vote with their wallets, then it's easy to keep creating. Even if I don't have that sorted out, though, it might still be worth the additional reach. People often say that it's better to spend on experiences than stuff. I wonder… It might be worth spending on scale, on other people's capabilities. Like the way I have more stuff than I need, I haven't even wrung out all that I can from the experiences that I've had. Scale sounds like a completely different category, one worth investing in.

2014-01-28 Delegation and helping people learn

What could get in the way of getting there? Trust is a big deal. It's probably the biggest limiting factor for the things I can delegate. If I can get better at choosing people, trusting them, and keeping that safety net for myself, then I'll learn more from this experiment with delegation. One of the things that I can do to make it easier is to separate my accounts so that I can see which tasks can be delegated at lower levels of trust. For example, I can share a Dropbox or Google Drive folder without granting access to the rest of my data, while other accounts (like Google) are intertwined with more of my digital life.

2013-11-27 Trust and assistants

I can also think about a sequence of tasks that allows me to build up trust in someone. For example, I'd previously written about mapping a strategy for outsourcing my podcasting process. If I set up the right sequence of tasks, I can give people more and more work to do, and eventually remove myself from most of the process.

I've been thinking about sequences of tasks to help people build their skills. One of my assistants would like to improve his written English. Aside from assigning ESL exercises, can I come up with practical tasks that will help him learn on the job? How can I help him immerse himself in lots of good English and gradually improve his writing skills with feedback, while still meeting my own goals for delegation? Data entry and web research might be good starting points; then summaries, more complex questions, transcripts, and maybe writing…

2014-01-28 Delegation and helping people build their skills

While thinking about how I can organize tasks to help my assistants grow, I realized that I actually get a whole lot more out of delegation than the usual benefits listed in books and blogs. This is good. It means that I can transform the dollars, time, and attention I invest in delegation into things I can't buy. Delegation is an excellent excuse to build and test a process library. I like the way that other people can take care of back-and-forth discussions as well as provide me with ways to work around resistance or things I don't enjoy. (Doing something repetitive can be boring, but writing good instructions is fun like the way automation is fun… =) ) I can take advantage of other people's skills, experiences, and perspectives, and their questions can help me clarify what I want. I get the satisfaction of helping people grow, and I grow as well through these uncommon experiments. Describing my processes and lessons learned is also a great way to meet people who are interested in delegation. The time leverage that's supposed to be the main benefit of delegation is actually just a small part of the picture.

2014-01-28 What do I get out of delegation

I think delegation will be worth the time I spend in ramping things up. I'm looking forward to building a massive process library that other people can learn from and use to build their own. I've met a few people who have process libraries of their own, but I haven't come across any that are publicly shared. (Maybe people think of them as competitive advantages?) I think I'll gain even more from the conversations than from holding these processes close, and I'll eventually figure out how to make the processes even easier to search and access.

Who wants to pick my brain about delegation? Who wants to share their insights? Let's figure this out together. E-mail me at sacha@sachachua.com and we'll set up a chat, or leave a comment with your thoughts!