I've been distracted for the past two months, since I've been focusing on consulting more than on my personal projects. Now that things are stable again, I'd like to see if I can make better use of delegation as a way to expand my capabilities, learn more, and spread the opportunities. There are so many people with talents and skills out there, and there must be a way that I can get the hang of this.

The purpose of going into business is to get free of a job so you can create jobs for other people.

Michael E. Gerber, The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It (1995)

What's getting in my way?

Mostly it's that I haven't sat down and thought about:

• The projects I'm willing to invest money into, in addition to time – although maybe I should just treat my time as fungible and delegation as a skill that's worth learning anyway, so I should open up all my personal projects for consideration
• Specific processes that I want to delegate, although I do have a decent-sized process library that I even share publicly
• How I can reduce my involvement in things that are tied to me personally, and focus more on things where I can bring in other people

I also have some guilt about the distinction between tasks I can definitely defend as being business-related, and tasks that are much more personal. For example:

• Reviewing my accounting records and draft tax return – Definitely business.
• Transcribing Emacs Chat sessions and recorded presentations – Well… Technically, people sometimes pay me for Emacs-related things and I'm working on packaging some things up as pay-what-you-can guides, so that's okay, I guess?
• Filling in recipes from Hacklab cooking nights – Definitely personal

The main benefit of claiming things as a business expense is saving roughly 15% in tax, but if that's mentally getting in the way of my just taking advantage of this, I should totally switch the contracts over to my personal credit card and just go for it until I've gotten the hang of this again. I'm nowhere close to my target of fully replacing the hours I've spent earning during this experiment (2829.6 hours worked, 486.8 hours delegated through oDesk, plus more through Paypal). But on the flipside, I don't want to assign makework that I really should just automate or eliminate. Although maybe I should challenge myself to find something useful, since that gives people an opportunity to work and to improve their skills.

Anyway.

Stuff I don't particularly enjoy doing, but that could help:

• Setting up events, coordinating with people, etc.
• Comparison-shopping
• Data entry
• Organizing

What would “getting the hang of this” look like? Future Sacha would:

• Have these beautifully documented step-by-step processes for consistently getting stuff done, with enough volume and throughput that things happen consistently
• Work with people who are also improving their skills and doing well

Hmm. One of the things I'm looking forward to learning at work is the ability to sketch out a design or give some tips on how to do a report (which tables, what existing report to build on, etc.) and have someone else learn by doing it.

Maybe what I need is something like that for my personal projects, too. If I get better at sketching out what I want, then I or someone else can make it happen. For example, with Emacs Chats and Emacs Hangouts, I'd like to eventually get to the point of:

• Having a list of questions or topics I'm working my through
• Having a page where people can see the things I'm curious about and volunteer to chat with me about them
• Coordinating with those people about when we're both available
• Sharing a calendar and events where people can see upcoming entries
• Getting everything recorded, processed, summarized, transcribed, and blogged about
• Harvesting interesting snippets for a guide

And for Quantified Self Toronto:

• Picture of sign-up whiteboard + copy of videos = processed videos uploaded and blogged about

For Hacklab and cooking:

• Picture of food + links to recipe = blog post draft with recipe ingredients, photo, links to recipes = updated wiki page

And a few experiments with Fiverr and other micro-outsourcing sites, too, just because.

You know, even if I don't end up feeling comfortable with calling those business expenses, I'm fine with it being a personal donation, since the communities are awesome. And it's stuff I would probably end up doing anyway because it's the Right Thing to Do.

Although it might be interesting to someday build a business around helping developers become even better… Hmm.

I am frugal by nature. I do the mental calculations almost reflexively. Food is my favourite measure of equivalent value, since I rarely buy books these days. If I bike instead of taking public transit, that's three Vietnamese sandwiches. For the price of dinner for two at Pho Hung, we could buy and roast two whole chickens. I hardly eat out, since I know I can make my favourite meals for $2-$4 a serving.

2014-03-06 Our frugal life #finance #frugality

Many people who are working on financial independence take pride in doing as much as possible themselves. It's a great way to save money and build a variety of skills. I usually do the same. It's great knowing that fixing a washing machine doesn't have to be a scary thing.

But there are some areas where I spend more than most people do, like outsourcing.  For example, even though no one expects transcripts for podcasts and even though I can transcribe my own posts, I pay other people to transcribe them for me. I pay people to research, draft, code, experiment, learn. I'm slowly getting the hang of passing on tasks even if I feel like I could learn a lot by doing things myself. If I outsource those tasks, then at least two people learn: my assistant and me. In fact, since they write down things I might otherwise just skim or take for granted, I can usually take what they send me and share that with other people.

For me, outsourcing is so much more than just a money-for-time trade off. I think of outsourcing as a way to help other people build up assets and skills as they figure out flexible work that fits their needs. It's a way for me to learn from different perspectives and experiences, too. I don't need stuff. I don't crave experiences: no exotic vacations, no once-in-a-lifetime memories. I'd rather take advantage of the abundance to scale up and help others.

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

(See more in Ramping up delegation)

Independence matters to me. So does interdependence. If I can carve out enough to provide reasonable security for myself and I have the skills to go and earn more money if I need to, then I'll use the surplus to make the world a little bit better. I had thought about focusing on stashing away more money so that we might have a greater margin of safety. (Who knows, maybe W- might even be able to retire.) I'm slowly adding to that stash, but that doesn't rule out helping other people along the way.

I don't want to become dependent on outsourcing. I make sure all my tasks are documented so that I can take over if needed. I establish financial limits so that outsourcing doesn't encroach on my other plans. (This is one of the reasons why I like working with assistants on an as-needed basis instead of committing to a specific number of hours or tasks a month.) I learn from small experiments before I move on to larger ones. I prefer outsourcing to people who can learn from the experience instead of to established companies with polished solutions.

I don't have to spend the money on this, but I decide to, and it's worth it to me.

How can you figure out a fair budget for delegating work? If you set your budget too low, you might get frustrated by lack of response or by the kinds of results you get. If you set your budget too high, you might waste effort and talent. I can't give you a price sheet. Besides, your needs will evolve over time. However, I can share some of the things I've been learning about budgeting for outsourcing or checking if people's times are reasonable.

If you're working with hourly assistance, you can ask people to track their times for specific tasks so that you can get a sense of how much something costs. You can also give a time limit and ask them to send you what they have at the end of that time. This will help you get a sense of their speed and the cost of the task. If you're working with fixed-cost services, you can translate things back into hourly estimates and compare that with your own experience. Pick one system of measurement so that you can compare your chioces.

Instead of trying to nail down a single price, try to figure out a range that you're comfortable with. You can start by looking for flat-rate fees from companies or people who post fixed prices online. For example, Transcript Diva lists transcript rates and timelines for some of their competitors as well. For general tasks, services like Fiverr and Fancy Hands help establish a range of $5-15 for common tasks.

Another way to establish a limit for what you're willing to spend is to consider how long it takes you to do things yourself, and what else you would do with that time. Adjust based on people's experience. Beginners will take longer to do things than you will, while experienced people may do this just as fast as you can. Specialists who have invested in tools or training may do things even faster. Sometimes it makes sense to delegate a task to someone who isn't the optimal choice in terms of speed or cost, if they're more integrated with the way you work or if you want to help them grow. (Sketch: 

Then experiment. Try delegating a small task to a lower-cost service to see if that will meet your needs. Try delegating a similar task to a premium service to see if it's worth the price. Try a mid-range service.

Think about the value you can get from the different types of results you have. If a service is expensive but it leads to a lot more income, it may be worth it.

Think of when you'd prefer to do things yourself, too. For example, even though it's easy to find inexpensive data entry assistance, I prefer to automate straightforward tasks because I get to learn more about automation along the way.

As you delegate, think about what was worth it, and adjust accordingly. Make your experiments a little bit bigger as you get used to the idea. Find your sweet spot, and then keep experimenting. Good luck!

I've been challenging my assumptions about what I have to do myself and what could be better with help. It would be a waste of time and talent to limit virtual assistants to just data entry or transcription. People can do so much, and they can learn even more.

2014-02-26 Thinking about delegation and projects

Writing is one of those tricky tasks. I can't stand generic link-building, keyword-stuffing articles. You know, the ones bashed out by SEO robots or humans doing a reasonable simulation thereof. Hasty writers hodgepodge snippets from various places. They may change words just enough to avoid plagiarism, but how can they add anything to the conversation? They don't have the experience you have. They can't tell the stories you can. They have a surface understanding of your field.

Still, I'm curious. Can I outsource part of my writing without feeling like I'm breaking the promises of my blog? Can I use people's strengths instead of bumping into the weaknesses of outsourcing?

I have a personal blog, not a corporate one. I have no problems filling every day with things I'm learning. People find my writing readable. I don't need help… but maybe I can learn how to make the most of it anyway.

For example, I've started making myself delegate web research tasks. This is tough. I keep thinking, “It'll take me five to fifteen minutes to do this research myself.” I read at a blistering speed, and the research process helps me reformulate questions. It's faster. I don't have to wait.

But it turns out that delegating research means I have to be clear about what I'm looking for and how important it is to me. I can learn from other people's search keywords and summaries. And each little bit of knowledge leaves its traces on two people: the assistant and me. Before, I was the only one who learned from any research I didn't capture as blog posts. With delegation, the two of us learn, and the summary becomes something I can share.

Example web research tasks:

• Find pre-show interview tips for podcasts
• Find best practices for encouraging conference participation from female speakers

So web research is one thing that might be worth delegating, even if I think I can do it faster myself.

What about drafting and writing? One of the challenges of writing is empathizing with people who are new. When I write while I'm learning, this is easy. I struggle with the same things people struggle with. But what about the things that people ask me about, the things that I already take for granted? This is where other people's questions and words can help.

I've assigned people to write about a topic I've outlined or sketched. I like the way that my outline becomes something both recognizable and different. Here are a couple of examples:

• TOBLOG How much does it cost to get started with virtual assistants?
• TOBLOG Dealing with mistakes while delegating

I really like the way people go beyond what I might think of doing or asking on my own. For example, this Trello tutorial is funnier than I probably would have made, and I like it.

What's beyond that? Maybe more conversation. Speaking can be faster than writing. I struggle with speaking because it feels so unstructured. I'm not used to dictation yet. Maybe I'll grow into that, in time.

I've been practising through interviews and transcripts, but not a lot of people host shows. Maybe I can ask my assistants to interview me about topics. That way, we'll get a recording out of it as well (for people who prefer to listen or watch). They may ask follow-up questions that I wouldn't have come up with.

Writing through other people also helps me learn more about my individual style. When I edit their work and give them feedback, I get a better sense of how I say or organize things. Maybe the differences will inspire me to pick up tips from them, too.

$20-30 seems a lot for a blog post that I can write myself, especially if I also invest time to outline and revise it. Still, I'm intrigued by the possibilities of learning from other people's perspectives. I like the way that I can assign topics of mutual interest, so that both my assistant and I grow through writing. It's worth exploring.

What would wild success look like? During this delegation experiment, I think it would be great to get to the point where I can make a list of questions I'm curious about. Assistants dig into those questions further. They interview me and other people along the way. I review their drafts, experiment with the ideas, and enrich the drafts with stories and results. We all learn.

I think some of the promises of my blog are: I will post things that I care about. I hope some of them will be useful for you. I won't clutter your feed reader or inbox with bland, impersonal articles that you could find everywhere else. I won't resort to clickbait headlines. I'll share what I'm learning.

Maybe delegation is compatible with those promises. We'll see. Here are two posts I've written with some help:

• Don't be afraid of mistakes when delegating
• How much does it cost to get started with virtual assistants? See the card for previous versions

What do you think? Can there be an authentic way of blogging with other people's help?

J-‘s been looking into the co-op program at her high school. In preparation, I've been planning tasks that she can work on during weekends so that she can flesh out her resume and portfolio with useful skills. 

I think co-ops might be good for me to look into it too. J- can't work for me because of rules against working directly for family members, but maybe I can give someone like her an opportunity to develop skills.

A high school co-op placement is about 4 months of afternoon work, or roughly 220 hours. It turns out that you can offer a co-op position even without an office environment. I would like to be able to give the right candidate a structured way to gain skills and apply them towards useful stuff. It's generally unpaid, so it's mostly low risk (although I like rewarding good work). Still, I want to make sure I have the kind of work that will attract good candidates, and I want them to be able to get a lot out of it.

What could wild success look like? Maybe I'd look for reflective self-directed learners who are interested in developing writing, tech, and design skills. I'd talk to students about their career goals and what skills they'd like to be able to demonstrate as part of their portfolio. I'd have a well-documented process library and a steady flow of tasks so that they always have something to work on. They would own a larger project, too. During the afternoons that they're working, I'd be available in person or over Google Hangout / Skype so that they can ask quick questions. Every week, we'd discuss our progress and make a plan for what to do next.

We could work on open source or community contributions together, or I might go and look for client work so that students get the experience of working with other businesses.

I want them to feel great about the diversity of experiences they get to try, to work on things that have value, and to feel supported and guided (versus being left to their own devices, or being exploited for cheap labour, or feeling lost).

It would be an investment of time and attention on my part. I'm at about 1 hour management : 3.5 hours of delegation for my virtual team, and supervising a high school student will probably require even more attention and thought. What would I want to get out of it? I'd make more progress on projects I want to support. We'd flesh out more documents, tutorials and blog posts along the way, too. Anyway, if things shape up well and I get better at managing other people, it might be worth looking into.

Do you offer a high school co-op position (or did you have one)? What has your experience been like?

If you're not used to delegation, hiring a virtual assistant can be daunting. It's a concept that's hard to grasp. How can I outsource my tasks? What kind of assistant should I hire? Where can I set up my virtual workplace? And this big question: Does it cost a lot to get started?

2014-02-13 How much does it cost to start with virtual assistance

1. It takes less money than you think.

Hiring a virtual assistant will cost you money, but it's not as expensive as you think.

How can hiring another living, breathing, employee to do tasks that you could have done yourself be cheaper? Let's look at an economic concept called comparative advantage.

Comparative advantage refers to any entity's ability to produce services or goods at a much lower cost. Imagine that you're a blogger with several hours of interviews to transcribe. Yes, you may be a fast typist. Still, this task can eat up a lot of your precious time. You could spend that time writing or consulting instead. Hire an assistant. Even if he or she works slower than you, it can mean that you'll be able to focus on tasks that have more value to you. Besides, with the right tools and a lot of experience, your assistant might even be faster.

You don't have to make a full-time commitment or even a part-time commitment. You'll find many freelancers open to one-off projects. For example, you can try data entry, editing, or basic bookkeeping. Take a look at Fiverr for ideas. For $5, you can get customized logo, proofreading for over 3,000 words of text, or a one-minute voiceover. I've used Fiverr to find people who can summarize my blog posts in tweets, type the text in my sketches,

If you want more supervision, you can hire your own assistant through a marketplace like oDesk. These sites have work trackers where you can check on your assistants' progress. Whether you're looking for the best skills or the best rates, you can work with people from all over the world. I outsource the most through oDesk. I like the management tools there, and I'm happy with the people I've found. There are many places to find freelancers, so look around.

2. It takes less training than you think.

You don't have to spend hours on training. Most of the people that you'll find on Fiverr or oDesk are already experienced freelancers. Just think about it – would they succeed selling their services if they weren't?

Start with something simple, such as transcription and data entry. These kinds of tasks are pretty straightforward and simple enough to do with minimal instruction. Make sure that your instructions are clear and easy to follow. You don't have to write detailed training manuals, either. You might start by demonstrating a task, and then have your assistant document the process along the way.

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

2014-02-10 Delegation as programming – also mentioned at What the LEGO Movie and programming are helping me learn about delegation

If you want to get a head start, check out my process library and my delegation board for examples. I'd love to hear what you do with this!

3. It takes less risk than you think.

Trust takes time to develop. I can understand why you might hesitate at the idea of hiring an unseen assistant (a complete stranger!) to do work for you. No matter how small the task may be, it's still your money and your time at stake here. Goodness knows I've had some interviewees and even virtual team members who gave me the heebie-jeebies. You can limit your risk by starting with tasks that don't require a lot of access, and you can share more as you get to know your team.

2013-11-27 Trust and assistants

Many job marketplaces have safety systems and guarantees. For example, on Fiverr, you can dispute orders or get a credit refund if it doesn't work out. One time, I paid for a Fiverr gig for transcription, and then the provider stopped communicating. Since the transcript was very late, Fiverr reminded me that I could cancel the order, and I did. oDesk gives you tools to resolve issues too. I hired a web developer and it turned out that he didn't have the skills I needed. Because he was one of the contractors covered by the new oDesk guarantee, it was easy to get a refund.

Delegation is something you learn through constant practice. Like anything else, you're going to make mistakes along the way. Protect yourself from big mistakes and learn from small ones. It's all part of the learning process. Start small. Let your virtual assistants work with small tasks first before trying bigger ones.

If worrying about the cost was getting in your way, I hope this helps you get started!