Category Archives: delegation

Like this? You might be interested in my Trello board and my list of processes.

The 5-year experiment: A conversation with my anxious side, and how sharing time might be better than giving money

(If you want, you can skip past the reflection on anxiety and safety and jump straight to the part on how you can help. =) )

Having resolved to learn how to work on my own things, I’m experimenting with reducing my consulting to one day a week (from last year’s routine of two days a week). I spend most of the week reading, drawing, writing, experimenting, and coding.

2015-01-09 What do I do on my non-consulting days -- index card

2015.01.09 What do I do on my non-consulting days – index card

It’s not a big change in terms of hours. I already have plenty of time for personal projects. But I feel the shift in the balance. I can hear that inner self-doubt saying, “Is this real work? Is it worthwhile? Is it sustainable? Are you undermining your safety by goofing off?”

2015-01-07 Real Work -- index card

2015.01.07 Real Work – index card

It’s okay. I expected this resistance, this anxiety. It’s just one of those mental barriers I have to break. Fortunately, all those Stoic philosophers are there to remind me that it’s just a negative impression, not reality, and the truth is that I have nothing to fear.

I’m getting better at telling that anxious part of my mind: “Look. Even though I offer all those resources for free, people willingly pay for it. And other people write wonderful comments and send me e-mail telling me that I’ve inspired them to learn more and that they want to help, so that counts too. Yeah, there’s a chance I might need to go back to Regular Work if the stock market crashes or a catastrophe happens, but in the meantime, just give this a chance. And really, that scenario isn’t the end of the world. Other people do okay. I can too. Besides, that’s why we have safety nets, right?”

2015-01-06 Planning my safety nets -- index card

2015.01.06 Planning my safety nets – index card

2015-01-06 Safe, a little better, comfortable -- index card

2015.01.06 Safe, a little better, comfortable – index card

And then my anxious side goes, “Okay, you’ve probably got the basics covered. But what if your expenses grow, or W- gets tired of living frugally and wants to upgrade lifestyles a little bit? Is this really enough?”

2015-01-06 Is this enough for me -- index card

2015.01.06 Is this enough for me – index card

And then I say, “We’ll probably have some time to adjust our plans for that, and I can always go back to doing Real Work that satisfies you. Besides, if we want to upgrade our life experiences, learning the skills to make stuff for ourselves often works out better than buying things. Like cooking!”

(It’s true! It’s even called the IKEA effect.)

Then my anxious side goes, “Fine. Maybe you have enough space to experiment right now. You want to learn things and help people. But look at your blog! It’s so self-centred. You talk about your questions and reflections, and you rarely give people tips they can directly apply to their lives.”

Then I say, “I’ll get better at writing for other people. In the meantime, this seems to be working okay so far. People translate my reflections into stuff that they can use.”

Here’s how I think my blog helps other people at the moment. Maybe you come across my blog because of a search. You find something that saves you a little time. You browse around a little and learn about things you didn’t even think about searching for. Maybe you come back once in a while for more of those ideas. You bump into other topics you’re curious about, and you explore. You might subscribe, even though you know I post practically every day. You skim the headlines for things that interest you, and you dive into stuff you like. Sometimes you might even feel moved to comment, e-mail, invest time, or even send some money.

2015-01-04 What kind of difference do I want to make, and for whom - index card

2015.01.04 What kind of difference do I want to make, and for whom – index card

How people can help

My anxious side grumbles, “Okay. I’m not sure your blog counts as Real Work, but I’ll grant that people seem to find some value in it. I’d feel better if you were more serious about building a business around it – if you could cover more of your expenses with this instead of consulting income or dividends.”

To which I say, “You know, I’m not sure any amount of money would get you to the point of not worrying. Besides, it’s good that you worry, because that helps keep us safe. This stream will grow as I figure out how to make things that are truly valuable to people. I bet you I can pull it off while still keeping the free/pay-what-you-want aspect, because that’s important to me. Given that you tend to squirrel away additional money to build up safety instead of getting better at investing it to build up capabilities, what we really should be thinking about is if we can make better exchanges of time instead of money. That will probably make a bigger difference anyway.”

My anxious side is sufficiently boggled by that idea and can’t come up with a good rejoinder. This is promising. Let me dig into it further, then.

One of the concepts I picked up from Your Money or Your Life (Dominguez and Robin, 1999) is that you can think of money in terms of the time it took you to earn it, a sobering thought when you apply it to your expenses.

I can apply that idea to other people, too; if other people pay money for something I made, it represents the chunk of their life that they spent earning it (and the opportunity cost of anything else they could’ve bought or invested in, including saving up for their own freedom).

I’m frugal (bordering on being a cheapskate), having gotten very good at making the most of inexpensive resources. Because of the typical mind fallacy, I tend to think that other people should be frugal as well so that they can save up for their own freedom. I suspect that people might get marginally more value from saving that money than I would get from them giving it to me, since their stress reduction or freedom expansion will likely outweigh my slightly increased feeling of safety. On the other hand, people do get value from feeling generous and from patronizing something that they would like to see flourish, so I can agree with that.

If we translate it back to time, though, I’m more comfortable with the exchange.

I already have enough time for the priorities in my life, while many people feel that they don’t have enough time for the priorities in theirs. Adding more money to my life doesn’t easily translate into additional or more effective time (aside from transcripts and tools, which I already budget for), while translating that money back into time might make more of a difference in other people’s lives. So a direct swap doesn’t make sense.

However, if we can exchange time in an apples-and-oranges sort of way, that might make sense. That is, if someone gives me 15 minutes of their time that translates to much more than 15 minutes of my time or might even be something I could not do on my own, that would be fantastic. This could be something that takes advantage of someone’s:

  • experience or particular mix of interests
  • ideas, knowledge
  • perspective (writing, coding, and all sorts of things can be improved with the perspective of someone who is not me)
  • questions
  • connections

Technically, delegation is supposed to help me translate money into time that is qualitatively different from my time, but my anxious side has not been very good at evaluating, trusting, or making the most of learning from people who know different things than I do.

Figuring out a way to effectively receive other people’s gifts of time might be what I need to break through this barrier.

2015-01-04 Thinking in terms of an exchange of time - index card

2015.01.04 Thinking in terms of an exchange of time – index card

In fact, receiving time might be more effective than receiving money. Not only could that get around my difficulty with finding and paying other people for the qualitatively different time that I want, but if we structure it right, people will gain from the time that they give. If someone asks me a good question that prompts me to learn, reflect on, or share something, we both gain. If they invest more time into experimenting with the ideas, we gain even more. I can’t actually buy that on any of the freelancing or outsourcing marketplaces. There’s no way for me to convert money into that kind of experience.

So, how can people can give me 15 minutes of time in a way that helps them and helps me? Let me think about different things I’m learning about:

2015-01-09 Time is greater than money -- index card

2015.01.09 Time is greater than money – index card

2015-01-09 What am I learning more about, and how can people help -- index card

2015.01.09 What am I learning more about, and how can people help – index card

It makes sense to organize this by interest instead of by action.

  • Emacs: Ask a question, pass along a tip, share a workflow. Also, I really appreciate people showing up at Emacs Hangouts or being on Emacs Chats, because my anxious side is always firmly convinced that this will be the day when no one else shows up to a party or that conversation will be super-awkward.
  • Coding in general: There are so many ways I want to improve in order to become a better programmer. I should set up continuous integration, write more tests, refactor my code, learn more frameworks and learn them more deeply, write more idiomatic code, improve performance and security, get better at designing… I find it difficult to pay someone to give me feedback and coach me through setting things up well (hard to evaluate people, anxious side balks at the price and argues we can figure things out on our own, good programmers have high rates), but this might be something we can swap. Or I could work on overriding my anxious side and just Go For It, because good habits and infrastructure pay off.
  • Writing: Comments, questions, and links help a lot. A few of my posts have really benefited from people’s feedback on the content and the structure of ideas, and I’d love to learn from more conversations like that. I don’t worry a lot about typos or minor tweaks, so the kind of editing feedback I can easily get from freelancers doesn’t satisfy me. I want to get better at writing for other people and organizing more complex thoughts into resources, so I could benefit a lot from feedback, questions, as well as advice on what to learn and in what order.
  • Drawing: I’m not focused on drawing better (I can probably get away with stick figures for what I want to do!), but rather on being able to think more interesting thoughts. What would help with this? Hearing from people about which thoughts spark ideas in them, which ones I should flesh out further. Book recommendations and shared experiences would help too.

So: Paying for free/pay-what-you-want-resources is great at helping me tell my anxious side, “Look, people find this valuable,” and that’s much appreciated. But giving me time works too. If we can figure out how to do this well, that might be able to help me grow more (at least until I sort out a way to talk my anxious side into letting me invest more in capabilities). Shifting the balance towards time is probably going to make my anxious side more anxious, but I might be able to tell it to give me a year or two to experiment, which is coincidentally the rest of this 5-year span.

Wild success might look like:

  • Thanks to people’s gifts of time and attention, I’m learning and doing stuff that I couldn’t do on my own or with the resources I could get in marketplaces
  • Thanks to people’s gifts of money (and maybe teaching), I’ve addressed more of my anxious side’s concerns and am getting better at experimenting with the resources I can get in marketplaces
  • I can incorporate people’s feedback and revealed preferences in my prioritization so that I work on things that other people find valuable

I could use your help with this. =) Shall we figure it out together?

Rethinking delegation

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.



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.

On why frugal me is cool with paying other people to do things

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

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

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.

Figuring out a fair price for outsourcing work

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.

2014-03-24 Determining a fair price for outsourced work #delegation #outsourcing

2014-03-24 Determining a fair price for outsourced work #delegation #outsourcing

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: delegation and task efficiency; blog post)

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!

Thinking about how virtual assistants can help me with learning and writing

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

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:

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:

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:

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

Contemplating co-op: How can I get to the point of being able to offer a good high school co-op placement?

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?