When I started this 5-year experiment with semi-retirement, I fully intended it to be a learning experience in entrepreneurship. I wanted to learn how to create value. I wanted to learn how to sell, how to build systems. Mission accomplished. I have the confidence that if I need to work, I can help people and earn money in return. I can deal with the paperwork required by the government. I can negotiate and make deals.

The more I learn about freedom and space and creating my own things, though, the more I think that this should be my real experiment, not freelancing or entrepreneurship. It is not difficult to freelance. Millions of people do it. There’s plenty of information about entrepreneurship too; no end to aspirational books encouraging people to break out of their cubicles and follow their dreams. But far fewer people have the space to simply create and share things for the sheer joy of it. Even the authors of those books on freedom work for their rewards.

It’s an interesting experiment to try. I could focus on working on my own things, going forward. I’ve been winding up my commitments and avoiding new ones. I still have a little bit of consulting to wrap up eventually. I’ve been telling myself that the money I earn increases my safety net so that I can take those future risks. Besides, I like the people I work with. I like the feeling that I am helping them out and making a difference. (And there, taking a step back, I can see that the desire for a clear sense of accomplishment may be distracting me from more difficult self-directed work.)

Really, nothing can buy time. Probably even if I stopped consulting now — or if I had stopped a while back, or never started — I could still spend an appreciable amount of time making things happen. Postponing this doesn’t make me live any longer. It doesn’t mean that I have more core time, those hours when I’m alert and creative and happy.

I hadn’t noticed for a long time because I had set too low standards for myself. I set trip-wires to trigger reflection: if I missed a commitment or started misplacing things, I knew I was overscheduled, and I cut back. The rest of the time, it was enough that family life was happy, blog posts were written, sketches shared. It was too easy to meet these conditions, so I didn’t notice.

What would I work on? Visual guides to complex topics look like the most unique contribution I can make, and there have been quite a few updates for my blog (both technical and written) that I’ve been postponing for lack of attention.

Details help me visualize what that might actually mean:

I should treat myself as a client and as a contractor. If I were delegating this work to other people, would I be happy with vague specifications and without milestones? I wouldn’t hire someone to maybe possibly think about something that could help people learn. I would spend the time to come up with a clear vision and the steps to make it happen, and then I would make regular progress that I would report on. The high-energy hours I have are best used for this long-term work; everything else can go into the non-core hours.

So I’ll keep my existing consulting commitment to Tuesdays and Thursdays, plus whatever non-core time I can spare to help them get over this hump, and then we’ll see if we’ll continue or not. In the meantime, any consulting of mine will be with the commitment to replace all the hours I spend earning with at least the same amount of time in delegated work (plus whatever time I need to manage the delegation). The end result won’t be as awesome as having the same amount of core time (and to be fair, my consulting involves non-core time too), but it should:

• build up a good library of procedures so that I can either delegate tasks to other people or work more consistently when I’m on my own (plus the benefits of process improvement and sharing)
• help me learn how to take advantage of other people’s time — and better yet, how their skills and experiences differ from mine
• allow me to support people as they build up their own businesses and the local economy

In fact, just for kicks, I’m going to backdate the experiment–to replace my original 5-year experiment with it instead of starting just from this point onwards. Since I don’t actually have a time machine, an easy way to make that commitment is to calculate all the time that I have spent earning so far. Fortunately, this is yet another question that time-tracking allows me to answer. The numbers in the sketches below are a little bit out of date now; the current ones are:

• 1874.4 hours spent earning since 2012-02-19
• 208.1 hours delegated through oDesk so far
• 55.1 hours spent managing the delegation (including documenting processes, interviewing, etc.)

So my ratio is about 1 hour of management to 4 hours of other people’s work. A ratio of 1.3 hours should be enough to account for delegating the work, managing the delegation, delegating the time to cover my management, etc. That means that if I want to replace about 1874 hours, my goal is to delegate a total of 2437 hours. So far, I’ve delegated 208, so I have 2,229 to go. (Ignore the math in the sketch; this is the updated version.) That’s a little more than a full-time employee. I’m not quite at the point of having streamlined, documented processes that can take full-time assistance over a year (or enough faith in my hiring abilities!), but I’ll work up to it. (My first goal: delegate as much as I can of this podcasting process.)

It’s a little scary delegating so much, especially since I’m normally quite careful about costs – but I think it will be worth it. In fact, I’ve been giving some virtual assistants raises to challenge them to think of themselves as people who can earn that. It’s a little scary projecting the expenses, but if I commit to it and then focus on making the most of it, I’ll gain more than I would if I kept waffling on the commitment. The work can start by replacing the routine, but it would be interesting to use it to support new projects someday.

As always, it helps to keep the end in mind.

I’ve been ramping up my delegation through oDesk, and I’ve also experimented with micro-task-outsourcing through Fiverr (with quite good results!). We’ll see how it goes.

It would be great to share processes with other people. Timothy Kenny gave me a glimpse of his growing process library. I’ve posted a number of my processes at http://sachachua.com/business, but haven’t updated it in a while. I’ll share more as I hammer them out. I wonder what my end-state would look like. Maybe I’d just share this Google Drive folder, and people can copy from it into their own libraries.

Anyway, plenty of stuff to figure out. =)

When I learn something new, I always find myself wishing there was some kind of map to help me figure out where to start, how to track progress, and what to learn next. So now I’m making them. Here’s one for learning Org Mode, a popular outline/TODO/everything-else mode for the Emacs text editor. You can probably figure out the relevant manual sections to read based on the keywords, but feel free to ask in the comments if you need more help.

Map for Learning Org Mode for Emacs

Here’s another short guide with suggestions for evolving your Org file organization:

Tips for organizing your Org-mode files

And here’s the one-page cheat sheet I made before helping someone dig into tracking time with Org. It’s a great way to measure your time on specific tasks.

Tracking time with Org Mode

Eventually I’ll get around to writing/drawing a book on thinking with Emacs. If you want it to happen, keep asking questions! =)

(Images are shared under the Creative Commons Attribution license, so reshare/reuse/remix away! Click on the images for larger versions.)

Quantified Self Toronto is organizing a conference on self-tracking in February. Whee! I’ve promised to put together a small workshop on time-tracking, since a number of people are interested in collecting and analyzing their time data.

Here are some rough plans for the time-tracking workshop:

I need to figure out what pieces people need to learn and what I can fit into the workshop time. Some of the pieces may have to be for follow-up or individually-paced study. Here are the pieces I probably need to put together. It still feels too large for a two-hour course, so I’ll need to trim it even more – maybe make iOS, Android, and RescueTime/ManicTime more cursory mentions than in-depth explorations.

Here are some thoughts on one of the pieces, transforming your time data.

More pieces: Easy ways to track time

Staying on the time-tracking wagon

I was offline during most of our trip to the Philippines, so it was a good test of how I could track without a Web connection to QuantifiedAwesome.com. I tried writing timestamps and activities in a small notebook that I kept in my beltbag, and I also tried using a timestamping application on my smartphone. (KeepTrack on my Android phone, if you’re curious.) The smartphone was much more convenient and less obtrusive, oddly enough. When I wrote timestamps down on paper, people commented on that as an unusual activity, but people are used to people checking their screens. Since I could easily backdate entries, I could postpone pulling my phone out until I wasn’t worried about safety or distractedness. When I got back online, I simply used the batch entry interface to add several days of entries at once.

I don’t have any iOS devices, so I might have a bit of a challenge putting together recommendations for people with iPhones. I’ve also gotten spoiled by the time-crunching capabilities I built into QuantifiedAwesome, so I’ll work on fleshing out  spreadsheet-focused analyses instead.

I’d like to put together some resources to help people get started during the workshop, with follow-up materials. I’ll also turn the info into an online course (most likely free). Would you like to help me make it happen? I’d love to hear from people who are doing similar things and have workflow tips/observations, and I’m also happy to test the material and do Q&A with people who want to apply the ideas to their life.

Lots of people posted tips in the Google Helpouts Discuss community, but the tips were getting lost in the stream of messages. I decided to pull out the tips, rewrite them for clarity, and organize them by topic. I didn’t want to be the keeper of the document, though – no sense in my being a bottleneck! So I started a new document in Google Docs, fleshed it out, and shared the link.

To share a link that lets anyone with the link edit the document:

1. Click on File > Share…
2. Under Who has access, change the first line to Anyone who has the link can edit.
3. Copy the link.
4. Click Done.

That’s all well and good, but when it comes to publishing the document to the Web, you probably don’t want just anyone editing it. Here’s how to publish a separate read-only link:

1. Click on File > Publish to the web…
2. Publish the document
3. Copy the link.

Since Google URLs are long and unwieldy, you may want to come up with custom short URLs for both the edit link and the read-only link.

Hope that helps!

The growing popularity of Google Helpouts mean that I often respond to requests from people who want to learn more about taking notes and learning more effectively. I want to make sure that people who book Helpouts with me (for the virtual equivalent of hot chocolate and a muffin!) think about specific questions, check for technical issues, and are otherwise prepared for the 15-minute conversation. That way, we can both get the most of the time.

Since I find myself sending people messages that are similar but not identical to others I’ve sent, I use text expanders instead of autoresponders to save myself time. My favourite automation program is AutoHotkey, which is rather geekily configured through plain text files. (Want a cleaner interface? Try Lifehacker’s recommendations for Windows or Mac). I’ve defined a few hotstrings that expand to welcome messages for my different Helpouts, nudges about technical issues, and so on.

If you find yourself typing or copying and pasting a lot of text frequently, consider using a text expander. Typing a pre-defined shortcut is easier than finding a specific item in your snippets file, and you might even be able to do all sorts of other things with the tool. For example, I’ve used AutoHotkey to set a keyboard shortcut for copying something from a Microsoft Excel spreadsheet row, switching to another application, pasting it in, reformatting it, and then moving on to the next row. Lots of good stuff. See my Autohotkey blog posts for more examples.

Be lazy and automate! =)

I found myself needing to download a whole bunch of JSON data from a server that had a weird authentication thing that Chrome could deal with but wget/curl/Ruby couldn’t. Since my Firefox was on the fritz, I couldn’t use Selenium IDE or the Selenium Webdriver. iMacros to the rescue! (Chrome, Firefox)

That plus lots of keyboard macros and text manipulation in Emacs, plus a little parsing and regexp substitution in Ruby, plus more Emacs munging got me the data I wanted. Hooray for bubblegum and string scripting!