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Planning ahead for the stories

Sometimes, when you take risks or make decisions, it helps to think about how your choices affect your story. We all tell stories. Stories are how we make sense of things. The same set of facts can support many different kinds of stories. The story you choose to tell–the perspective you pick–affects how other people see you or make sense of your life.

stories

When I was planning this experiment with semi-retirement, thinking about the stories that I could tell helped me make that jump. How would I explain that gap in my career if I decided to work someplace where that could matter? After all, most employers want commitment, not gaps.

It helps that I’ve been able to plan ahead. Having enough savings to cover five years of expenses lets me tell a different story compared to someone who quit a job without having anything else lined up. Leaving my job on a happy note is different from leaving because I was burned out. Structuring this break as a time-limited experiment helps me make sense of it. I incorporated right away, and eventually came up with a company name that was general enough to cover a lot of different things I was interested in exploring. If I tell the story in the right way, then the five years that I’ll spend outside the easily understandable structures of work will give me a different but possibly useful perspective. If I don’t have a story to tell, it will just look like drifting.

The human brain is really good at rationalization, so you can come up with multiple stories to fit your facts. You don’t even need to make things up. You can choose the parts you want to emphasize, the reasons you want to explain. Also quite handily, there are lots of stories you can pattern yours on. For example, I might be framing this as an experiment now, but I can also talk about it in terms of freelancing. People shift to freelancing, and some shift back. If we have kids, then my story could be as simple as those of many other parents who’ve taken breaks from traditional careers. The on ramp might be tricky, but it’s there. And even if I started my break a few years before having kids, people probably won’t dig into that.

Imagining one possible Sacha of five years after the experiment (with subtext or notes in parentheses), pitching a business:

Yeah! I was doing well at IBM (evidence: performance ratings, recommendation letters, testimonials), but I knew that I wanted to learn more about business, technology, and other topics. Besides, I’d saved up a lot, so I could take more risks. I gave my manager plenty of notice and transitioned all my projects neatly. (See, I’m responsible.) I experimented with different kinds of business models and found that I really enjoy helping people understand complex ideas through simple visuals, tutorials, videos, and consulting. I learned about what I can do on my own, and now I want to scale up by working with a good team. (So that’s why you don’t have to worry about me being all flighty.) With the skills I polished (NodeJS, more Ruby, even Emacs geekery) and the network I developed, I think I can help you make even awesomer things happen.

Another Sacha, talking about choosing alternative paths:

I had a great time in the corporate world, so I wanted to see what the other types of work were like. I have a lot of role models who have small businesses, and I was excited about learning how to build one myself. I experimented with different business models and was lucky to find immediate profitability with consulting, sketchnoting, and publishing. I re-invested those profits, and the investments grew enough to cover my needs. Since I have the time and space to explore things just because, I’ve decided to focus on the things I like to do: helping people learn more about Emacs or visual thinking. It’s pretty cool what you can do when you challenge your assumptions.

And yet another Sacha, blending in with the crowd (assuming we have kids):

I took some time off to raise a family. Since I knew I wanted to get back into technology afterwards, I kept my skills up to date by working on open source projects and building sites. You can see my portfolio at ____. Why don’t we set up a trial project so that we can find out if this is a good fit?

I think a lot about what’s going to be part of my story. I want to be able to put enough into that box, and I want it to make sense. Time moves so quickly. I’m already almost halfway through these five years. What I want to be able to say at the end of it? How am I different now compared to when I started, and how much more different do I want to become?

I’m more comfortable with business and paperwork than I used to be. I was pleasantly delighted to discover that I could create things that other people valued, and that people would buy things even if they could get them for free. I learned how to put together e-books and printed books. I got more comfortable at helping people online, and I learned that was something else that people valued. I learned how to interview people and turn that into additional resources. I got deeper into drawing, and I used that to explain ideas and explore my own reasoning.

I haven’t learned as much as I thought I would about some of the technologies I was curious about. I’m still not a super-leet developer of Emacs, Rails, Node, or Android. I spend more time on the beginner side of things, building resources and filling in gaps. That’s useful too, so I’m not too worried.

What do I want to add to this story? More coherent Emacs evangelism: guides, e-books, then maybe books – more help, more chunks that are part of a story (and that tickle my brain and that result in good karma; it’s icing on the cake that it’s part of a “worked on open source” story). Maybe Org or other Emacs contributions. More modern web development. Writing. Plenty of writing. Someday, more style and humour.

So far, my investment income covers what I need. It is always possible, however, that I’ll need to focus on more active work. Something might happen to W-, or our situation might otherwise change. I’m not entirely sure yet that I have a good plan for that, although I’ve set aside some buffer so that we can ease into it slowly. In those kinds of scenarios, I’d probably post here while I figure out my options, which will likely involve programming of some sort or another. (Then people can be part of the story too!)

Sometimes I think about alternate universe Sachas who travel in parallel along more conventional paths. It’s less about “what if” or “if only” and more about “Hmm…” I can relax a little, knowing that alternate universe Sachas are exploring those trails. I check in with myself from time to time: is the story worth the divergence? Can I scent other interesting story possibilities nearby?

While I give up a little of the power of the story by actually talking about my thought processes, I’m betting that it’ll help more than hinder. At the very least, this will probably help other people think about their stories.  =)

What are the different stories you can tell about the facts of your life, and how are you working towards the stories you would like to be able to tell? Here are some tips I’ve picked up:

  • Look for similar stories that you can pattern yours on–and that you can use to decide where you’ll diverge
  • Brainstorm different aspects you can emphasize about your story
  • Try out the stories you want to be able to tell

Reinvesting time and money into Emacs

I received a wonderful token of appreciation from someone who found my Emacs posts useful. It got me thinking: what would it be like if I made Emacs a large part of my life’s work, and how can I invest even more into it?

Emacs is already a big part of my life. I like the community. I get a lot of positive feedback indicating I might be doing useful things. It’s not like much would change, except perhaps that I’d give myself permission to focus on this, to put more eggs in this basket. I might write about Emacs more often, even if it makes other people boggle. I might tweak the design of my blog to simplify browsing through Emacs-related resources, and maybe come up with an easier-to-spell domain name for that part of my site. Focusing on Emacs is probably low-risk, since my savings give me a decent runway if I need to build up more marketable skills like WordPress or Rails. (Or I could be, like, one of the few Emacs coaches/consultants in the world. ;) )

To make the decision clearer to myself, here’s what would go on the backburner: specializing in a more popular platform (WordPress, Rails, etc.), Quantified Self, helping people with blogging, helping people with sketchnoting, helping people with freelancing/semi-retirement, delegation, and so on. I could probably build up a reputation in those communities later on, but I like Emacs the most right now.

I like focusing on helping people discover the joys of exploring and customizing Emacs: blog posts, tutorials, suggestions, screencasts, maps, and maybe someday those guides and books I’ve been talking about writing. I like helping make Emacs learning slightly more manageable – “if you know about this, you might want to check out that.” I enjoy coding, but I haven’t gotten deeply into the big improvements people are working on for Emacs 24 and later. I’ll probably continue to focus on filling in the gaps instead of pushing Emacs forward.

I’ve been thinking about how I can reinvest money into the Emacs community. There was a recent thread on the Orgmode mailing list about donations – trying to figure out how to put people’s donations to the best use. Sometimes I receive donations too. Since I keep my expenses low and there’s only so much safety you can save up for, how can I put small amounts of money to good use in open source?

Domain name, hosting, etc.: I use a Linode VPS – I switched from Rackspace in 2011. A virtual private server is more expensive than shared hosting providers. I like how I can ssh to it to try different things. I’ve thought about lowering my costs by using DigitalOcean, but I don’t know enough yet about server optimization to properly configure my web server setup so that I’m confident I’d fit into a smaller plan. (Hmm, this might be worth experimenting with someday, especially since I could set up a snapshot and save it…) I’ve budgeted for this and for domain naimes since this is such a big part of what I do, so I don’t mind covering this myself and using donations/unexpected income for other things.

Transcripts for Emacs Chats and other videos: I’ve been outsourcing this instead of doing it myself because transcription is a well-specified chunk of work that I can pass to other people (who can learn a little more along the way). It takes about $35-$60 for a transcript, and then I often edit it a little. The assistant who does my Emacs Chat transcripts is interested in programming, but hasn’t gotten into Emacs specifically. It might be interesting to find someone who’s interested in Emacs and who will get even more out of transcribing videos. (If this describes you, e-mail me!)

Emacs/Org conference? Meeting folks in person was super-awesome. If last year’s conference happened because someone found a venue willing to host us for free, it makes sense for me to pay for a venue. Even if it’s over a thousand dollars, that’s cheaper than a flight and visas and all sorts of other things.

Emacs meetups? Quantified Self Labs supports QS meetups by sponsoring Meetup.com fees ($144 per year), pitching in for video cameras, and paying someone to process videos. They also have people working on blog posts and other community-related projects. Would a similar model make a big difference? Maybe it makes sense to get a few of them off the ground. What’s in the way of my hosting an Emacs meetup here?

Editors / information organizers: I try to make my writing easy to understand, but it can be good to have other people review something to see if it makes sense and to spot the gaps. Volunteers and blog readers help a lot. Still, it might be a good idea to pay people to help me with this. I’m not looking for surface-level editing, but more developmental editing: helping me organize ideas so that they make sense and they’re in a logical order. I’m not sure if looking on the usual freelance writer sites will help me find someone who can do this, but maybe if I can offer a good enough incentive, then maybe a freelance developer/writer will be able to spend some time helping me with this. (Or I can just take longer and I can get better at asking for feedback…)

Bounties? https://www.bountysource.com does not seem very popular for Emacs or Org. I’m still not sure how bounties interact with intrinsic motivation and unequal valuing of work, or how to even value a fix.

There’s still so much beyond money that I haven’t yet fully delved into. Aside from re-investing money, I can invest time – and that’s probably more important, more useful.

How can I invest more time into the Emacs community? What do I want to work towards? How can I improve how I learn and share?

Continue what I’m doing, and do more of it: Tweak Emacs and write about it. Be that friendly co-worker or friend you chat with because you know she’s always coming up with the weirdest things to try, and sometimes that leads to surprisingly useful things. Post more screenshots and screencasts, since we could really use those.

Fill in more gaps: Answer newbie questions. Map topics to learn. Write tutorials. Link to resources. Make screencasts. Organize information. Read EmacsWiki and other resources, and organize/edit/fill in as I come across opportunities to improve things.

Guide more people towards Emacs Lisp: Help people make that jump to writing their first custom bit of Emacs Lisp. Learn more about Emacs Lisp style and functionality, and help people improve their packages.

Help inspire and connect people. Bring the community together: Interview people for Emacs Chats, so that other people can get a sense of people like them who are enthusiastic about Emacs and who use Emacs to do interesting things. Set up a regular Emacs show-and-tell series?

On a related note: what would it take to figure out how to do Emacs coaching properly? I’d want to keep track of people’s progress and set up recurring calls, so probably Org, maybe in Google Drive or Git… I have a little bit of an impostor syndrome around this because I don’t know enough about setting up Emacs as a modern IDE, but I can learn. Clojure, Rails are probably good starting points, and there’s Emacs Lisp itself. On the other hand, if I answer questions in newsgroups and mailing lists, I help more people, and it’s easier (and more reliable) to turn those into blog posts. Plus they’re searchable. But sometimes one-on-one real-time helping is what helps me map or understand things better, and it can really make a difference in someone’s confidence or comfort level. So yes, continue to do these, and continue to nudge people to share.

Do these decisions make sense even considering a scenario where, say, Emacs becomes irrelevant? I’ll have learned more about related programming tools and topics. I’ll be a better writer and teacher. I’ll probably know a whole bunch of people who are happy about what I’ve shared and who can help me make the transition to other things as needed, maybe by sharing information or by taking a chance on me. And then there are all the other skills I’ll build on the way: making sense of technical things, learning more about how things learn, and playing with all sorts of other things along the way.

Payoffs? Tickled brain, happy mastery. Besides, you meet the nicest people using Emacs. =)

Rethinking my time categories: the blurring of business and discretionary activities

I track my time with medium-level categories (not detailed enough that I’m tracking individual tasks, but not so high level that it’s hard to make sense of the data). From time to time, I notice categories drift, or they stop fitting. Consulting is definitely business, but does working on Emacs really belong there? Why is coding classified under business but writing is classified as discretionary time? Most of my categories still make sense a year or two later, but some of them could use more thinking about.

What is business, anyway? I suppose it can include anything related to the earning of money, including support such as paperwork or delegation. Packaging (by which I mean creating e-books and other resources) is part of business, since I earn a small income from that (and pay taxes on it, too!). So is responding to e-mail. Technically, Emacs is related to money, because people have actually booked and paid me for help sessions online (http://sachachua.com/help). I consider programming-related activities to be part of maintaining my technical skills and network. In that sense, coding, web development, system administration, and other geek things are business-related. I distinguish between sketchnoting for client engagements and drawing on my own. Many of my drawings are more along the lines of personal or business planning. Perhaps I should track more under those categories now that I’ve established drawing as a way of thinking, and shift to using “Business – Drawing” when I’m specifically working on illustrations or improving skills.

Discretionary time includes the stuff I do just for fun and the things I learn about just because (Latin and Morse, for example). Probably the only weird thing in here is that I classify writing as discretionary time. It’s fun. Coding is fun too. Coding is more obviously valued, though, so I guess that’s why I consider it business time. And also, if I classify writing as coding time, I’ll tip over way too often into the “working too many hours a week” zone, when I’m not really doing so.

Maybe a better approach is to classify coding, drawing, and other fun things as discretionary time instead, even if they occasionally result in money. Benefit: I get to celebrate having more discretionary time and a lighter workload. (Yeah, it’s all mental anyway…)

Or maybe I need to take a step back and ask myself what kinds of questions I want to be able to answer with my categorical data.

In general, I want to make sure I don’t spend too much time working, because I want to force myself to work on my own projects. That’s why I track the time spent consulting, doing paperwork, and connecting with people (including responding to e-mail). I usually keep a close eye on my Business – Earn subcategory, since that’s the one that can creep up on me unawares. That’s fine with my current categories.

I also want to look for patterns in time use. How does spending more time on one activity (and less time on other activities) influence what I do and how I feel? How bursty am I when it comes to different discretionary projects? As long as I’m tracking at the subcategory level, it doesn’t really matter what the root category is.

Hmm. Since I’m not actually using the distinction between discretionary and business for reports or visualizations that nudge my behaviour, I can probably leave my categories alone if I remind myself that those ones have fuzzy boundaries. It would matter more if I wanted to set goals for investing X hours a week on business things (or, conversely, spending Y hours on discretionary non-business related things, which is oddly harder). Since I don’t care about that at the moment, I’m fine. Also, it’s easy enough to reassign the parent categories, so I still leave the door open for analyses at a later date.

As long as I can keep things clear enough in my head so that I feel confident that I can explain to any auditors that yes, my  business expenses make sense, I should be fine. I feel a little weird about not having a proper business plan for lots of things I’m working on. I mean, I can write them (or draw business model canvasses, more likely), but I prefer this pay-what-you-want model. Oh, hey, there’s an assumption there that I can dig into. People can (and do!) build metrics around freemium or pay-what-you-want models. Maybe I can figure out how to approach this in a business-like-but-still-generous way.

What would a more business-y way look like? I would float an idea to see if it’s useful. Then I would make stuff (and sometimes I’d make it anyway, just because). I might actually track conversions, and try things out, and reach out to people and communities. I’d publish little guides and videos, and maybe add a tip jar for smaller pieces of content so that people can “vote” for things they like more.

All things to do in due course. In the meantime, knowing that the path is there means I can leave all of this stuff still filed under the Business category, because it is. Even if it’s fun. Writing still feels more discretionary than business-y (even posts like this, for example), so I’ll leave that where it is. So no change, but I understand things better.

Do you track your time and have fuzzy boundaries between categories? How do you deal with it?

 

 

Working fast and slow

When it comes to personal projects, when does it make sense to work quickly and when does it make sense to work slowly? I’ve been talking to people about how they balance client work with personal projects. It can be tempting to focus on client work because that comes with clear tasks and feedback. People’s requests set a quick pace. For personal projects, though, the pace is up to you.

It’s easy to adopt the same kinds of productivity structures used in the workplace. You can make to-do lists and project plans. You can set your own deadlines. I want to make sure that I explore different approaches, though. I don’t want to just settle into familiar patterns.

2014-04-07 Working fast and slow #experiment

2014-04-07 Working fast and slow #experiment

I work on personal projects more slowly than I work on client projects. When I work on client tasks, I search and code and tweak at a rapid speed, and it feels great to get a lot of things done. My personal projects tend to be a bit more meandering. I juggle different interests. I reflect and take more notes.

Probably the biggest difference between client work and personal projects is that I tend to focus on one or two client tasks at a time, and I let myself spread out over more personal projects. I cope with that by publishing lots of little notes along the way. The notes make it easier for me to pick up where I left off. They also let other people learn from intermediate steps, which is great for not feeling guilty about moving on. (Related post: Planning my learning; it’s okay to learn in a spiral)

Still, it’s good to examine assumptions. I assume that:

  • doing this lets me work in a way that’s natural to me: what if it’s just a matter of habit or skill?
  • it’s okay to be less focused or driven in my learning, because forcing focus takes effort: it’s probably just the initial effort, though, and after that, momentum can be useful
  • combinations of topics can be surprisingly interesting or useful: are they really? Is this switching approach more effective than a serial one or one with larger chunks?
  • a breadth-first approach is more useful to me than a depth-first one: would it help to tweak the depth for each chunk?
2014-04-02 On thinking about a variety of topics - a mesh of learning #my-learning

2014-04-02 On thinking about a variety of topics – a mesh of learning #my-learning

One of my assumptions is that combining topics leads to more than the sum of the parts. I took a closer look at what I write about and why. What do I want from learning and sharing? How can I make things even better?

2014-04-02 Evaluating my sharing #sharing #decision

2014-04-02 Evaluating my sharing #sharing #decision

Emacs tinkering is both intellectually stimulating and useful to other people. It also works well with applied rationality, Quantified Self, and other geekery. I can align sketchnoting by focusing on technical topics and  on making it easier to package things I’ve learned. Blogging and packaging happen to be things I’ve been learning about along the way. Personal finance is a little disconnected from other topics, but we’ll see how this experiment with the Frugal FIRE show works out.

If I had to choose one cluster of topics, though, it would be the geek stuff. I have the most fun exploring it, and I am most interested in the conversations around it.

What does that mean, then? Maybe I’ll try the idea of a learning sprint: to focus all (or almost all) my energies on one topic or project each week. I can work up to it gradually, starting with 2-4 hour blocks of time.

2014-04-02 Imagining learning sprints #my-learning

2014-04-02 Imagining learning sprints #my-learning

Because really, the rate-limiting factor for my personal projects is attention more than anything else. If I experiment with reducing my choices (so: Emacs basics, Emacs chats, open source, Quantified Self), that will probably make it easier to get the ball rolling.

2014-03-28 Identifying rate-limiting factors in my work #kaizen

2014-03-28 Identifying rate-limiting factors in my work #kaizen

So I’m still not adopting the taskmaster approach, but I’m reminding myself of a specific set of areas that I want to explore, gently guiding the butterflies of my interest down that way.

We’ll see how it works out!

Experiment update: Mid-term pre-mortem check

In the early days of my 5-year experiment with semi-retirement, I brainstormed ways it could fail. I worried that I might end up too distracted to make useful stuff, or that I’d end up being incapable of pursuing my ideas, or that I’d mess up somewhere–paperwork, people, products–and botch the whole thing. I worried that I’d finish the experiment with nothing to show and no compelling story for the gap I’d have in my resume. I worried that W- would get tired of this exploration.

20121210-business-planning-experiment-premortem.png

20121210-business-planning-experiment-premortem.png

I feel less worried now. Part of it was realizing that I can plan for only so much safety. Part of it was learning how to choose what I’m going to focus on, how to select my projects without managers and track my progress without annual performance reviews. (Well, I still have annual reviews, but they’re self-driven.) Part of it was trusting that I can handle things, a confidence which grew after each small step.

Looking back, I can see the things I found mentally challenging in the beginning, and how I worked around them.

  • The career gap doesn’t look all that scary now. I know lots of other people who have managed it. They’re fine, and I’ll be fine too.
  • Self-direction turned out to be good to learn, and it seems like I can come up with useful projects.
  • Paperwork? There were a few stressful hours as I learned more about the tax code – I amended my first corporate tax return a number of times – but I think that doing my own books was worth it. Besides, Canada Revenue Agency is surprisingly approachable. Hmm.
  • Opportunity cost? “Wasted potential” only
2014-02-21 What did I find challenging when I started #experiment

2014-02-21 What did I find challenging when I started #experiment

If you’re starting your own experiment or you’re well into one, I’d love to hear about some of the challenges you faced and how you worked around them!

Going fishing for three years

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.

2014-02-19 Teaching people to fish, selling fish, fishing for yourself #experiment #sharing #my-learning #teaching #confederates #community

2014-02-19 Teaching people to fish, selling fish, fishing for yourself #experiment #sharing #my-learning #teaching #confederates #community

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.

2014-02-19 Imagining wild success for this experiment #experiment.png

2014-02-19 Imagining wild success for this experiment #experiment.png

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!