When I was coming up with a three-word life philosophy, learn – share – scale felt like a natural fit for me (Nov 2012). Learning and sharing were pretty straightforward. I thought of scaling in terms of sharing with more people, sharing more effectively, building tools to help people save time, connecting the dots among people and ideas, and getting better at getting better.

A recent conversation got me thinking about scale and the different dimensions that you can choose to scale along. For example, startups often talk about scaling up to millions of users; that’s one kind of scale. There’s saving people five minutes and there’s launching people into space; that’s another kind of scale.

What kinds of scale I see myself exploring? Here’s a rough categorization. (With ASCII art!)

Category	Left	Where I am	Right
Size	“This might save someone five minutes”	X---------	“I’m going to help people get into space.”
People	“This might help 1,000 people.”	-X--------	“I want to help 1 billion people.”
Time	“This might help 1,000 people over ten years.”	X---------	“I want to help 1,000 people tomorrow.”
Team	“I’m going to gradually develop my skills.”	-X--------	“I’m going to build a team of people.”
Performance	“We’ll start by doing it manually.”	-X--------	“I want to get to sub-second response.”
Focus	“I’m going to explore and see what comes up.”	X---------	“I’m going to focus on one idea and knock it out of the park.”
Variety	“I’ll put lots of things out there and people can tell me what they value.”	--X-------	“I’ll choose what to put out there and connect with people who need that.”
Demand	“I’ll come up with the idea and find the market.”	----X-----	“I’ll find the market and then come up with an idea.”
Pace	“If I grow slowly and steadily, I’ll build a solid foundation.”	--X-------	“If I grow quickly, I’ll have momentum.”
Time/money tradeoff	“I’m going to make my time more valuable.”	---------X	“I’m going to make something outside the time=money equation.”
Risk	“If I mess up, things are still okay.”	X---------	“If I mess up, people die.”
Empowerment	“I’m going to do things myself.”	-------X--	“I’m going to support other people.”
Teaching	“I will build systems so that I can catch fish for more people.”	--------X-	“I’m going to teach more people how to catch their own fish.”

Hmm. This is similar to those visions of wild success I occasionally sketch out for myself as a way to test my ideas and plans. Wild success at scaling up for me (at least along my current interests and trajectory) probably looks like:

• Learning about a wide variety of interesting things
• Writing, drawing, and publishing useful notes
• Getting better at organizing them into logical chunks like books and courses so that I can help more people (including people who don’t have the patience to wade through fifty blog posts)
• Reaching more people over time through good search and discovery in my archives
• Getting updates to more people through subscriptions and interest-based filters

What would an Alternate Universe Sacha be like? I’d probably keep a closer eye out for problems I run into or that people I care about run into, and practise building small websites, tools, systems, and businesses to solve those problems. I might start with trying to solve a problem for ten people, then a hundred, then a thousand, then ten thousand and more. I might look for medium-sized annoyances so that it’s worth the change. I might build tools instead of or in addition to sharing my notes. (After all, The $100 Startup points out that most people don’t want to learn how to fish, they just want to eat fish for dinner and get on with the rest of their lives.)

Hmm. Alternate Universe Sacha makes sense too. Since I’m doing fine in terms of Normal Universe Sacha and scaling up here is mostly a matter of gradual accumulation, it might be interesting to experiment with Alternate Universe Sacha sometime. Maybe during the next two years of this 5-year experiment, or in a new experiment after that?

It’s good to break down a word like “scale” and figure out the different dimensions along which you can make decisions. Are you working on scaling up? If so, what kind of scale are you working towards?

(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.

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?"

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?"

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?"

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.

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.

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:

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?

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.

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?

People often ask me if I could draw for them, or write for them, or code for them. I refer all that business to other people. Here's why.

You see, some people want to learn how to fish. These are the people who want to learn more about sketchnoting or Emacs or other things I'm interested in.

Many people want to buy fish. They don't want to learn things themselves, but they can build on what they buy.

Most people just want to buy sushi. (Or fish and chips, or whatever.) Already prepared, no work needed, yum. They're too busy to cook. They don't want to know the details. They just want good stuff.

I want to learn how to fish for rare fish. The kind of fish few people bother with because you have to go into uncharted waters. Interesting, elusive fish, almost too smart to get caught. I want to learn how to ask good questions and share what I'm learning.

I want to be part of a community of enthusiasts who swap tips and stories. I want to find other people who have gotten bitten by that bug, and I want to help other people discover the joy of exploration. That's why I'm not selling any fish. I'm focusing on learning how to fish rare fish, and teaching what I'm learning. My top priority is to learn how to fish. But I'll take the time to teach you to fish because I want to be able to learn from you someday.

Sure, I might be able to learn a little while catching fish for other people. I know from experience, though–both mine and others–that it's too easy to get used to that. You forget there's a world beyond the fishponds. Better to force myself out there, while I can.

At least for the next three years (the rest of this 5-year experiment), I'll be out fishing. That is, drawing, writing, learning, playing – somewhere out there, where few people get to go. What would wild success be like? Plenty of stories, maybe a few mementos, and a great community to keep exploring with.

Thanks to Evan Smith for the nudge to explore this metaphor!

(Note: I don't know anything about fishing, and I'm not planning to add it as a hobby. But I do like cooking, though, which might explain some things.)

Tell me what you think!

• What can I help you learn how to fish?
• Are you looking for rare fish too? Let's learn together!

While cleaning out my blog drafts (150+ had accumulated over the years), I came across a post that I had started writing in February 2009. Part of the draft had been incorporated into this imagination of wild success, but the draft had more details I had never gotten around to posting. It's been almost five years since then, so I thought I'd dust it off and see what had happened.

What would wild success look like? Thinking about this helps me figure out where I want to go and how I want to get there. The picture is still fuzzy and I know it'll change over time, but it's interesting to see what's in it and what isn't.

Here's what a day in my future wildly successful life could look like:

Life is fantastic. I'm happy, I'm making a difference doing something I love doing, and I smile every day. I wake up at 5:00am to kisses, cats, music, light, and colors. I exercise a little in the morning, to help me wake up and get the day off to an energetic start. I have a delicious and healthy breakfast with loved ones – fresh fruits in season, steel-cut oats, fluffy pancakes, or other favorites. Then I clear the kitchen table, do my morning planning, and work on some fun, creative things: brainstorming, writing blog posts and articles, and developing prototypes and systems. I snack on nearby fruits and nuts throughout the morning. I may launch a new information product before lunch, or at least once a week. The payments start rolling in.

As it turns out, 5 AM is much too early for me. 8 AM is more reasonable. Yes to kisses and cats (technically, cat – only Neko is allowed in the bedroom). Reading this reminded me that I should set my alarm to some music instead of the chime that I set during my last system restore. Lights and colours are accomplished with bedside lamp and smartphone. I don't bother with exercise unless I really need to wake up fast; with enough sleep, I usually wake up well-rested. Our breakfast routines have settled into plain rice and fried egg, occasionally with beef tapa; sometimes oatmeal or congee if we make a large batch. I work on the kitchen table because I like the sunlight, although I also like using the desk I've set up downstairs. I decided against the information-product route, at least for now; I'd rather learn, explore, and share for free.

We have a light and yummy lunch: leftover pasta, salad, soup, or something like that. Then I work on more routine tasks: testing code, editing and formatting documents, answering mail, following up with people. I also check on the status of my delegated tasks, and things are going well. Towards the end of the day, I wind down by doing chores. Sometimes we take a walk to pick up new books or groceries. We exercise, make dinner, and take care of other things. I spend some time connecting with others socially, too – writing on my blog, connecting with people online, calling people. The day ends on a happy and thankful note.

Routine tasks get deferred to low-energy time at some point during the week, now that I've learned to be less guilty about my inbox. Things are going well with delegation. =) Chores continue to be a great way to wind down, although I tend to do library walk after lunch so that I can get some exercise and sunlight. I've decided to not bother with making phone calls, although I'll dip into social networks at the beginning and end of my day. Google Helpouts has become an interesting way to schedule interaction, too.

The income from investments covers my basic expenses, freeing me up to work on information products and experiment with things I'm interested in. I've figured out how to create and capture lots of value using the Internet, and I enjoy making little experiments and creating value. The money from that goes into my “retirement” fund (which is really just about freeing up even more of my time to work on larger projects), and into a few luxuries. Our lifestyles remain simple, and our expenses are minimal.

I crunched the numbers for last year, and I was surprised to find that my (theoretical) capital gains exceeded my expenses by a healthy margin. Yay! This and other things mean I can experiment with giving what I know away for free / pay what you want, which results in much less friction and much more happiness (at least for me). =) Our lifestyle is pretty much the same as it was in 2009, except that I buy a slightly wider range of groceries and I occasionally buy tools.

I visit the Philippines at least once a year, and I sometimes stay there for a while so that I can hang out with friends and try different experiences. When my friends are busy working, I work remotely, creating more things and trying things out.

It works out to every other year or so. Last time, we stayed for a month, which was much more awesome than staying for just two weeks. =)

I regularly give presentations to companies, universities, and other groups, and I have a good workflow for putting those online and helping people learn from them. I help organize virtual and in-person events, bringing people together for great conversations. I experiment with ideas for helping people connect and collaborate. Sometimes I coach people, too.

Semi. Writing and drawing is much more fun than giving presentations, and I have a good workflow for putting my sketches online. I help organize a couple of meetups in Toronto, and I'm getting pretty comfortable setting up online conversations. And yes, I'm experimenting with helping people connect through Google Helpouts, and a lot of those conversations look like coaching. Funny how that works out…

I enjoy playing some favorite tunes on the piano, drawing diagrams and pictures, and writing about life and technology. I enjoy sewing, and my wardrobe is full of clothes that make me feel happy and creative.

Nope on the piano and the sewing, but yep on the drawing and writing. My wardrobe is pretty much the same it was back then (aside from the addition of a few tech-fabric shirts and pants). It's better-tracked, though! <laugh>

It's amusing to unearth old notes and reflect on how things actually worked out, and how my tastes haven't changed much over the years. What I'd sketched lines up closely with how I live, but that's because my wants are small. I knew back then that I would probably do an experiment like this, and that helped me save for it. Here I am, learning things I hadn't even put on my list. =) What will the next five years be like? I'm not sure yet. If it's more of the same, that will be awesome; and if it's different, I'm sure it will be awesome too.

One of the assignments in the Rockstar Scribe course I’m taking through Alphachimp University (affiliate link) is to sketch where you want to be in five years. This is my sketch.

What does that mean for 2013?

Work: I’m focusing on business idea validation, sales, and marketing this year. It’ll mean scaling down my consulting income, but I think the opportunity cost will be worth it. To keep building other market-valued skills, I may still do a little web development – primarily for my own projects, but possibly for others as well.

Relationships: I’m focusing on spending time with W- and friends, especially through exercise and cooking. I’d also like to organize things more at home, and to learn more kitchen skills.

Life: Regular exercise supports my goals here as well, and so does organization and decluttering. I’m looking forward to digging deeper into Emacs for planning and organization, too.

—

Learn: I’ll research and go to interesting events to sketchnote. I’ll also keep an eye out for good books to review.

Share: I’ve sketched out an editorial outline of things I want to write about, which may help me write with more deliberation.

Scale: I’m documenting many of my ideas and processes in a public manual, and I’ll add more as I learn how to scale up.

Onward and upward!