Category Archives: experiment

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Reflections on learning to be an entrepreneur

The other week, I focused on exploring ideas and becoming my own client. Last week, I focused on the systems I can set up in order to keep on sharing while I’m distracted by work or other needs. The other week felt happier and more self-directed, but on reflection, last week is great for long-term learning and growth as well. I just have to keep tweaking the balance. Some weeks might be more exploratory, and some weeks might be more focused on packaging things and building processes. I’ll probably spend more time on consultinfg going forward than I thought I would two weeks ago, but I can see the benefits of investing the extra income into building up my delegation skills and experimenting with business ideas. (Besides, my clients are nice, and I want to help them do well.)

2014-02-07 Adjusting the balance

2014-02-07 Adjusting the balance

Thinking about this balance reminded me of this conversation that I had with Ramon Williamson, who has been thinking about the differences between artists and entrepreneurs. He’s coming to terms with the fact that he wants to focus on just speaking and coaching, and he doesn’t want to deal with a lot of the other small things that are part of building a business. It’s like the way my dad focused on just photography while my mom took care of running the company. Ramon is looking for someone who can manage him. I think a lot of people are like that, even the ones who have been self-employed for a while. That’s why partnerships often make sense, and why people often struggle with self-employment or self-directed learning.

I think of entrepreneurship as learning how to build processes, then systems, then businesses. It turns out  actually enjoy doing this. I stayed up until 1 AM Sunday morning interviewing an applicant for a writing gig that I posted on oDesk. She seems fine, so I hired her and walked her through what I’m looking for. I’m excited about the possibilities. I briefly thought of agreeing to experiment with managing Ramon and using that as practice for developing my systems, but I’ve committed to doing public work that builds up my life brick by brick. So I’m going to invest in building up my processes and skills, but I’m going to do that with my own content. That will also encourage me to develop my “artist” side: writing, drawing, coding, sharing, and so on.

Does it always have to be a partnership between an artist and an entrepreneur, or can you do a decent job at both? It seems like artists need to partner with entrepreneurs, but entrepreneurs with artistic bents can sometimes pull things off on their own. I think it makes sense for me to focus on developing those entrepreneurship-related skills first. It might mean growing slowly as an artist, but I think processes can scale up art so much. For example, becoming really comfortable with delegation will allow me to imagine things that I can’t do on my own. This seems to be something that lots of people struggle with. Most people I talk to have issues with trust, perfectionism, and other barriers. That means that it probably doesn’t take that much effort to get good enough to distinguish yourself, so if I can get to that level, that would speed up my growth even more.

2014-02-08 Artists and entrepreneurs

2014-02-08 Artists and entrepreneurs

People’s interests and skills are unevenly distributed. In some areas, it takes a lot of effort to get good enough. In some areas, a little effort goes a long way. It reminds me a little of how one strategy for playing role-playing games is to be a munchkin: to maximize your strengths and minimize your weaknesses in a way that allows you to exploit the rules of the game. While that can lead to games that aren’t particularly enjoyable (unless you’re playing a game that makes fun of munchkinry), in life, a little of that strategy might be interesting. So, in the areas where I have unfair advantages–and in particular, unusual combinations of unfair advantages–I might be able to recognize opportunities for uncommon contributions.

This enjoyment of building processes and systems is one such unfair advantage. Coding is another, and delegation is almost like a people-version of coding. Frugality lets me take advantage of compounding interest. Reflective learning helps me take advantage of figurative compounding interest, which is enhanced by speed-reading my way through other people’s experiences and insights. Satisficing and optimism allow me to avoid the dangers of perfectionism and make it easier for me to experiment and trust. Self-direction lets me use these advantages to my own ends instead of being limited by someone else’s imagination or by a job description.

2014-02-08 Unfair advantages

2014-02-08 Unfair advantages

It is a handy combination of advantages. You should be out there, Ramon said. Joining the ranks of infopreneurs (many of whom seem to make their money by telling other people how to be infopreneurs). Making things happen. Living the life. I’m a little meh about the idea. I’ll grow at my own rate and at my own time. Plus, I like the free-and-pay-what-you-want model so much more than the buy-my-training-course-for-$X-hundred-dollars. I like the way it engages generosity and acts from abundance, both on my side (here is a gift!) and on other people’s. (Here is some totally optional appreciation! Make more stuff like this.) I’ll either figure out how to make that work, or I’ll eventually come around to setting prices. In the meantime, I can focus on building up those unfair advantages at the same time that I’m building up the things I want to make with them.

For example: delegation. I like framing my work as something that people can flexibly do more or less of, depending on their schedules and energies. It’s the same freedom I have with consulting, and I think it makes it easier for people who work for me as well. So it’s not a fixed “You must work 20 hours a week” thing, but rather, “Here’s a board with all the different tasks waiting for someone to work on them. Pick something you want to work on. You can work more hours on the weeks when you want to, and you can work fewer hours on the weeks that you need to. Just tell me if you need to be away for a while, so I can make sure that work gets reassigned.” I’ll check in with my virtual assistants to see if this is working for them or if they need deadlines or set times for focus and motivation. Eventually I might work up to asking for consistent time slots so that I have an idea of turn around times, but the system seems to be working so far.

I’ve been adding more people to my virtual team. There’s a range of rates (anywhere from $2-12/hour), and I’m working on gradually getting more of my assistants to deserve and totally justify higher rates. I proactively give them bonuses and raises, even. Instead of micromanaging who works on what in order to maximize cost-efficiency (approach A: different people for different skills; see diagram below), I’m experimenting with putting all the tasks on Trello and letting people choose from the tasks based on their skills and energy. If I’ve got good enough rapport with the team, then people might focus on the stuff that really justifies the value in their rate. I want to get to the point where people are generally cross-trained, so people can take the task and see it through end-to-end (approach D). I remember from Toyota’s lean method that this makes work better (versus the assembly line, where you only see your small part).

I’m also working on chunking higher-level tasks – the delegation equivalent of going up a level of abstraction, writing procedures that call other procedures. (See my list of processes) For example, I started with separate tasks to extract the MP3, add metadata, upload to, transcribe the audio, etc. Now I’m testing the task of posting show notes, which includes all of those. Maybe someday I’ll get to object-oriented programming!

2014-02-08 Delegation and task efficiency

2014-02-08 Delegation and task efficiency

I started by mostly working on my podcasting flow, but I’m also experimenting with delegating other processes to support learning or sharing. For example, how can delegation support my drawing? My process is pretty efficient at the moment (aside from some cross-referencing data entry that I don’t usually get around to doing myself), but if I batch things up more, maybe other people can help me tag my sketches and turn them into posts.

2014-02-05 Delegation and drawings - where does it make sense
2014-02-05 Delegation and drawings – where does it make sense

Writing is another good candidate, too. Podcasting and drawing help with writing, so it all comes together. I want to get even better at pulling stuff out of my head and out of other people’s heads, and getting those ideas into a form that other people can easily learn from. That’s why I’m experimenting with getting writers to help me pull out ideas from Q&As in transcripts and from all these thinking-out-loud self-reflections that may be a little too long and rambling for most people to make the most of. For example, a reader-focused tips post based on this might just focus on building systems and omit the role-playing games references. The end goal for that one would be to have a blog that mixes shorter, focused tips with long behind-the-scenes notes, and to have e-books (and maybe even physical books!) that flow well. That way, it’s good for people who just want a burst of inspiration so that they can get on with applying the ideas to their life, and it’s also good for people who like seeing the verbose tracing messages as I think and learn.

It’s a bit strange investing so much in the processes and output without yet building up the kind of audience and demand that justifies it, but I think it’s the Right Thing to Do to have transcripts and follow-up blog posts and all that jazz. If I grow sustainably and keep an eye on my finances, I’ll probably get to that take-off point right when I have the skills and systems to support it – and more importantly, the community. I figure it’s much easier to build great relationships with confederates/tribe people (Hi!) and provide useful resources for searchers while I’m not distracted by the mainstream yet, and I might not even bother with going mainstream. I’m just going to focus on you, and maybe you’ll find it so awesome that you’ll bring in a few people for whom this is also a really good fit.

That seems to be the general pattern of how I’m learning about entrepreneurship. I’m investing in the capabilities now rather than waiting for demand to completely drive it – almost like my own little MBA. Still cheaper than $80k+ for an MBA at Rotman, and you’ll get better value out of my “class projects” (like this free PDF/EPUB/MOBI of my No Excuses Guide to Blogging guide). At some point, we’ll figure out a proper business model. Maybe it’s sponsorship. Maybe it’s pay what you want. Maybe it’s membership, although we’ll need to find something that doesn’t involve just exclusive access to content, since I like making ideas as widely spread as possible. Maybe more of a coaching program? If you want me to sell to you, tell me how you want me to sell to you. (Comment, tweet, or e-mail me!)

2013-11-17 Should I sell to people more - If so, how would you like that

2013-11-17 Should I sell to people more – If so, how would you like that

(Although to be fair, there’s probably a lot of demand already out there. People have been asking me for an Emacs book for years. Look! I’ve started drawing maps and other Emacs tips. It will happen. I just need to sit down and share more raw material. This means you need to sit down and ask me questions about stuff I’m taking for granted.)

Maybe it’s a weird sort of entrepreneurship that I’m growing into, but I think it will be fun. How can I use what I’m learning to help you?

A conversation about writing, and reflections on taskmasters

I’m fascinated by the idiosyncrasies of systems that we build for ourselves over decades. I’m particularly interested in what people find weird about themselves and their systems; what they do the most differently compared to other people. When John Allemang picked my brain about a piece on the Quantified Self, I jumped at the opportunity to pick his brain right back. Here are the notes I drew to summarize the thoughts from our conversation:

2014-01-24 A conversation about writing

2014-01-24 A conversation about writing

It was reassuring to know that one could build a life on a variety of interests, accumulating notes and interviews along the way. I don’t have to specialize in a narrow set of topics. I don’t have to build expertise in a specific field. There’s a lot to learn about how to organize your thoughts and structure your words, but that’s not the only thing that experience gives you — it also gives you the confidence that you can do things. Where inexperienced writers let their egos and insecurities get in the way of good interviews and good writing, experienced writers can let go, confident that it will all come together somehow. It reminds me a little of trapeze practice. If you hesitate, if you cling to the bar, you’ll never get the thrill of flight. I wonder if I can fool my brain into believing I have all that experience to draw on–to compartmentalize that belief and use it deliberately.

It was also good to know that I don’t have to worry about remembering everything. Discarding details is essential. I sometimes imagine that I’d go through life with virtual file cabinets stuffed with clippings and drafts, but then I might drown in irrelevant notes and unfinished possibilities. I asked John if he had a process for managing his archives. He told me that he doesn’t particularly worry about it. It’s okay to discard. It’s okay to let go.

While the historian may bemoan the loss of evidence from these temporary notes, discarding has always been a central feature of effective note-taking. Discarding enhances the utility of notes that are saved by removing materials that have been superseded.… Discarding and forgetting are crucial to effective information management.

Too Much to Know: Managing Scholarly Information Before the Modern Age (Blair, 2010, p.65)

Talking to John gave me a clearer idea of what it might be like to be an experienced writer: to have the clarity of mind to focus on the story, and to have the confidence in yourself so that your self doesn’t get in the way of taking risks, learning, and sharing.

We talked a little about freedom and self-direction, which I’ve been curious about. John sounded skeptical; he values editors and deadlines. Reflecting on our conversation, I wondered what I’d be missing by writing outside the world of work. I’ve experimented with hiring editors. The editors I found on oDesk and other freelance sites gave me feedback on form, but they don’t fulfill the other crucial roles of an editor: choosing a vision for a piece, setting constraints, pushing back on fit, coaching improvement. Writing coaches may be able to do a little more of that, but I’m not sure if the client relationship throws off the dynamic.

2014-01-24 Being my own editor

2014-01-24 Being my own editor

I saw in this the same idea I had in becoming my own client - to see if I could enjoy some of the benefits of workplace structure by deliberately stepping into that role. Could I as editor challenge myself the writer to stretch with more difficult topics, more explicit constraints? How could I step outside my writing and coach myself to improve? (You can pay a writing coach, and I’ll experiment with that someday, but it also pays to coach yourself – no one could be more devoted and more consistent than you.)

Later that evening, thinking about deadlines and freedom and the liberal arts, I caught myself wondering if this path–easy and familiar as it is, falling back into the structures of the workplace–if this path is really the only way. After all, if I put on the hat of the client or editor or capitalist, and then remove that hat and put on the hat of the worker, am I setting myself up for internal conflict and waste? Wouldn’t it be better to be one self, doing the right thing at the right time?

Giving myself directions and deadlines might be useful for avoiding decision fatigue–the cost of making too many decisions–but it is also good to be able to adapt. I do this a little by thinking through scenarios beforehand, so I know what I can do with low-energy and high-energy opportunities. The specific actions I take are influenced by my TODO list, which helps because I don’t have to brainstorm good things to do each time. But I rarely commit to doing specific items, and I allow myself space to go off plan.

2014-01-24 Not about swapping one master for another

2014-01-24 Not about swapping one master for another

It would be easy to be my own taskmaster, to set up that rider and elephant dynamic (rational and irrational, logical and emotional). It’s understandable. It’s productive. Everyone has tasks. Everyone has deadlines. I can even use it to masquerade as normal in cocktail party conversations, griping about an unreasonable boss. (No need to tell them I’m imposing those conditions.)

It’s easy to adopt that structure, which is why I’m curious about alternatives. What does good self-direction look like? What would it mean to be good at that? Can I run fast without the whip?

2014-01-24 Why are we so attached to deadlines

2014-01-24 Why are we so attached to deadlines

I haven’t figured this out yet. It sounds promising, though. At the very least, it’s an experiment worth exploring.

So, three things:

  • I’m going to borrow the confidence I heard from John. I think that assuming more confidence will let me take greater risks in writing and learning.
  • I’ll consider using an editor or a writing coach to improve my skills. In order to make the most of that, I can clarify my goals and coach myself as much as possible. That way, I might be able to identify my questions and the parts where self-coaching breaks down. (Like when it comes to murdering your darlings!)
  • I’ll take a closer look at this instinct towards deadlines and taskmasters, rooted perhaps in a fear that I am not enough. Let’s try being plan-less, as paradoxical as that is. Here is where that confidence can help. I trust that it will all work out.

I think I’m coming close to the end of this research into other people’s writing systems, at least for now. I’ve seen a lot of common patterns. If I run across an interesting tip, I’m happy to pick it up. But I’m worried less about making a mistake now that I’ll regret in thirty years (such as not archiving every little note, or not having enough associative hooks for memory), and I’m not looking for the one tip that will make me an order of magnitude more effective. There’s still a lot to learn, but I can learn that through practice, observation, and small improvements.

Still, so much to learn, and (probably) decades ahead of me… Let’s see where this goes!

Other-work and self-work

Since I decided to become my own client, I’ve been thinking about the things I think of as work and the things I do out of my own volition. Work is shaped by other people’s goals, priorities, and directions. When it comes to the things I do for myself, I am responsible for figuring all of that out. I haven’t truly delved into entrepreneurship yet, small publishing experiments notwithstanding. I haven’t said, “This is something I believe is worth making and selling,” and I haven’t matched that to people who need it. I’ll learn how to do that someday. First, I want to learn how to direct myself.

2014-01-22 Work and its place in my life

Work and its place in my life

In drawing these notes, I thought that this self-directed work – focused on my own needs and curiosity – might be more limited in effect, but also that it might benefit me more through compounding. When I choose my own work, I can build things up instead of getting pulled in different directions. (Or at least, if it seems like I’m scattering my attention over different topics of my own choosing, the logic might emerge later.) Everything I work on benefits both other people and me, but sometimes other people more than me, and sometimes me more than other people.

Or is that really what I’m balancing? In the margins, I poked at that assumption. Was it really a spectrum between other-focused work and self-focused work? What if other-focus and self-focus were actually orthogonal? What if you could do things that were very useful for yourself, but also pretty useful for other people? That sounded like a more interesting possibility. I’m probably not quite there yet, but if I get better at doing things that I find useful, I might also get better at making those things useful for other people.

I thought about whether I wanted to postpone that kind of self-exploration until after I wrap up my consulting engagement, but I decided that doing it in parallel was better. It is always tempting to postpone vague, self-directed work in favour of clearly-defined, other-directed paying work, but is it ever truly profitable to do so? I should use my uncommitted core hours for growing, even if it feels slow.

Something useful to myself AND to others… Blogging would probably be a good way to practise. I noticed that although the daily themes helped me make sure I didn’t overlook different topics, I sometimes found myself writing blog posts that were helpful for other people but didn’t make me learn as much. I hadn’t been challenging myself to learn something new either about the topic or about the way I could share. If I focus more on stretching my understanding, would my blog become less useful to others? What kinds of things could I write that might be useful for me now and later, and which might also be helpful for other people? Reflections, perhaps, if other people resonate with them and use them to think through their own lives. My notes on things I’m figuring out; solutions to technical problems; tips and other resources. Reviews, perhaps, as a summary of things I’ve shared and an update on things I’ve learned. I don’t know how helpful these things will be, although I’m encouraged by comments that seem to indicate they’re interesting to read.

Then what is blogging's place in my life?

Then what is blogging’s place in my life?

I think other- versus self-focus might be the reason why I find myself much more interested in new questions than in the connective work of filling in the gaps of a book outline for a potential audience. I get different pay-offs from different types of sharing. When I answer other people’s questions (things I know implicitly but haven’t explained yet), I get the satisfaction of thanks and interaction. When I answer my own questions a small step at a time, I get a kick out of learning something. When I make a map of unknown territory and start learning about it, I enjoy the thrill of learning. When I’m writing tutorials and I’m not sure if they’re going to be useful or if other people are already fine with perfectly good resources out there, it’s a bit more of a struggle. I’d rather not duplicate information or write for the sake of leaving my fingerprints on it. Might as well write about something unknown that I’m figuring out, or at least help a specific person who has already tried other resources and can tell me what’s missing.

2014-01-20 How could I get more out of my sharing v2

How could I get more out of my sharing?

So what does that mean? I’ll probably focus on the right side of the quadrant above – the things that I don’t know. Possibly my blog may become more boring; on the other hand, it might become more interesting. But even if it does get a little more boring, I have to get through the boringness in order to figure out how to be more useful. =)

How can I do work that's more useful to myself and others?

What can I do? I can share the questions that I’m asking, and maybe people will find themselves surprised by the insights they can share. I can show my work, and maybe people will consider reasons or approaches that wouldn’t have otherwise come to mind. I can connect the dots through links, because those will be handy later on.

I hope I learn to write with more depth of understanding, less fear of embarrassment; more clarity of thought, less attachment to fads and fancies; more initiative, less intellectual laziness. And then, eventually, to come full circle: to write with a focus on other people’s needs, but to be better at observing and celebrating the hidden fascinations of even familiar topics.

Becoming my own client; also, delegation

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.

2014-01-12 Being my own client - part 1 of 4

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.

2014-01-12 Being my own client part 2 - Projects

Details help me visualize what that might actually mean:

2014-01-12 Being my own client part 3 - Emacs, blog

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.)

2014-01-12 Being my own client part 4 - buying back time

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.

2014-01-17 How can I assign 30 hours of work a week

As always, it helps to keep the end in mind.2014-01-17 Thinking about delegation goals

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.

2014-01-14 Ways to increase my delegation-fu

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, 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. =)

The power of no: being completely* unhireable until 2017 (and possibly longer)

When I started this 5-year experiment, I didn’t know if I could stick with it. My track record for sticking with interests is not that good. I’m delighted to report that (semi-)retirement gets easier and easier. I am learning to say no.


By coincidence, two of my mentors (who had moved on to separate companies after IBM) got in touch with me one after the other to find out if I was interested in some upcoming job opportunities. Good stuff. Right up my alley. Wonderful people.

I said no. Actually, I said something along the lines of: “Thank you for reaching out! That sounds fantastic. However, I am semi-retired and completely* unhireable until 2017 (or possibly later), so I’ll just have to wish you good luck on your search. I’m sure you’ll find someone awesome out there. If I think of returning to work, I will be sure to reach out to you right away. Thanks again!”

*If a significant financial need comes up, I have no qualms about suspending this experiment and returning to the wonderful world of work. I enjoyed working with excellent teams. I’d love to do it again. While I have the opportunity and privilege to work on things entirely of my choosing, though, I should do that. Not everyone can do so, and I shouldn’t waste the chance.

Learning how to say no is amazing. I used to feel guilty about this. I wanted to be in more than one place at a time. Then I realized that I am not a special snowflake and there are other awesome people out there who can make things happen. Sure, they might not bring my particular configuration of skills, but they’ll bring other useful combinations. This makes it easier for me to say no, because it leaves room for someone else to say yes.

Pre-making decisions helps a lot. When I was preparing for my experiment, I thought about the conditions in which I would stop or reconsider. If something happened to W-, I might go back to work. If our expenses didn’t stay in line with my projections, I might go back to work. If, if, if. If everything was going fine, though, then any qualms or anxieties would just be the product of my irrational lizard-brain trying to run back to the safety of the known, familiar, and explainable-at-cocktail-parties. (Not that I go to cocktail parties, and not that “I’m in consulting” was really an explanation. But it checked the right conversational boxes, while “I’m semi-retired” throws people for a loop.) Knowing my lizard-brain helps me work around it.

I often sketch out basic decisions in advance. It’s the programmer way. If this, then that. Check for warnings and errors. Handle exceptions. It means not having to worry as much, which is great. It means knowing when I might need to reconsider so that I’m not blindly following the same plan when circumstances change. In a way, I live through many possible lives.

It’s been a year and a half since I started my experiment with semi-retirement. My living expenses are almost exactly on track. My aspirations are definitely off track. I hadn’t expected to be this comfortable with writing and learning, and I’m excited about where this is going. This is good.

The road isn’t lonely at all. W- has been absolutely wonderful and supportive, and I’m running into more and more people on some kind of sabbatical or early retirement. The path is surprisingly well-travelled, the kind of secret trail that you might not hear about in your guidebook but which gets passed on from person to person in whispers and geocaches. I say no so that I can say yes.

Image credits: Crossroads (Mopic, Shutterstock)

Reflecting on a month of experimenting with Proper Retirement


When I started on my 5-year experiment, I hedged my bets by thinking of it as semi-retirement. I was open to working part-time on a flexible basis. Consulting worked out well for that. People also wanted me to work on illustrations and sketchnotes, and I figured that was a great way to spread visual thinking while being paid to learn. I earned more than I expected, creating a good safety margin for my experiment and making it easier to plan continuing it.

Because I didn’t want to settle into too much of a familiar pattern, I interrupted my experiment with month-long sub-experiments. One month, I travelled for a conference and spent time with my family. Another time, I focused on building a sketchnoting business.

This August, I experimented with my idea of Proper Retirement: living with minimal commitments, following my interests. I didn’t do anything billable, aside from the occasional check-in with my existing consulting clients when they raised the bat signal. I didn’t look for new work. I slept in without guilt. It gave me the time to work on some personal projects and build some skills.

I didn’t get around to everything, but I like the progress I made. I wrote a lot, learning more about outlining and illustration. I drew a series of sketchnoting tutorials. I outlined book ideas. I updated my archive of favourite posts. I learned more about researching. I reached out and chatted with people online. It was good. And I actually earned a smidge of income from the pay-what-you-can e-resources on my site, so yay that!

I like this focus on self-directed projects. No clients means no easy source of feedback, no built-in challenges, and no direct transactions for income–but it also means less stress, less commitment, less chasing down of accounts receivables. If I get better at planning what to work on and getting feedback from people through Twitter and blog posts, I can be my own client.

Besides, this arrangement forces me to get better at planning for different circumstances. I anticipate that life is going to get even more variable, not less, and that it will be harder to make commitments, rather than easier. It makes sense to learn how to manage my time and create value instead of being comfortable with the guidance that client projects give me in terms of schedule and initiative.

So now what? I want to experiment more with taking the initiative. I’m probably going to wind down my consulting over the next four months. My clients are doing well, which is exactly what should be happening. Although people sometimes ask me to sketchnote events, I might wind that down as well, referring the work to other people I know in Toronto and elsewhere. It’s interesting, but it’s also an hours-for-money swap, and I tend to get better information density from books. (And less performance anxiety?) I’ll take care of my existing clients’ needs, and I’ll pass other opportunities on. It feels a little weird to say no to things, but that’s part of the experiment: to learn how to be less afraid of closing doors and moving on, knowing that in many cases, I might be able to reopen those doors if I need to.

What could this look like if I focused on doing things that I chose? Writing and drawing still have their place. Writing lends itself to packaging, of course. I get the occasional unexpected bonus from Amazon affiliate links or Gumroad sales. Maybe someday I’d even make my peace with advertising, although I’m not sure about that. As for drawing, perhaps I’ll make stock images and more interesting guides. Maybe writing and drawing will come together in course development. Maybe I’ll take the occasional professional writing or illustration gig. Maybe I’ll learn how to pitch freelance articles to magazines and blogs. Maybe we’ll see how the next few years changes the landscape.

There’s some benefit to staying in business, and some costs too. I have a corporation, and that’s been very useful. I’ll keep it around as I slowly disburse what I need from it in the form of dividends (or a salary, if I can justify that). Having a corporation involves some ongoing costs for paperwork and things like that, which I’ve been fine with doing so far. The benefits for working under the umbrella of a corporation include a little tax flexibility (which was really helpful when I was going full-tilt as a consultant) and some tax savings involving business expenses.

My income’s probably going to be a fraction of what it used to be. There might even be years when it would be negligible, perhaps below expenses. The CRA bulletin IT504R2 has this to say about visual artists and writers:

In the case of an artist or writer, it is possible that a taxpayer may not realize a profit during his or her lifetime but still have a reasonable expectation of profit. However, in order to have this "reasonable expectation of profit" the artistic or literary endeavours, as the case may be, of the artist or writer must be carried on in a manner such that, based on the criteria in ¶ 5above, they may be considered for income tax purposes to be the carrying on of a business rather than, for example, a hobby.

The criteria mentioned are:

    (a) the amount of time devoted to artistic or literary endeavours,

    (b) the extent to which an artist or writer has presented his or her own works in public and private settings including, but not limited to, exhibiting, publishing and reading as is appropriate to the nature of the work,

    (c) the extent to which an artist is represented by an art dealer or agent and the extent to which a writer is represented by a publisher or agent,

    (d) the amount of time devoted to, and type of activity normally pursued in, promoting and marketing the artist’s or writer’s own works,

    (e) the amount of revenue received that is relevant to the artist’s or writer’s own works including, but not limited to, revenue from sales, commissions, royalties, fees, grants and awards which may reasonably be included in business income,

    (f) the historical record, spanning a significant number of years, of annual profits or losses relevant to the artist’s or writer’s exploitation of his or her own works,

    (g) a variation, over a period of time, in the value or popularity of the individual’s artistic or literary works,

    (h) the type of expenditures claimed and their relevance to the endeavours (e.g., in the case of a writer there would be a positive indication of business activity if a substantial portion of the expenditures were incurred for research),

    (i) the artist’s or writer’s qualifications as an artist or writer, respectively, as evidenced by education and also by public and peer recognition received in the form of honours, awards, prizes and/or critical appraisal,

    (j) membership in any professional association of artists or writers whose membership or categories of membership are limited under standards established by that association,

    (k) the significance of the amount of gross revenue derived by an artist or writer from the exploitation of that individual’s own works and the growth of such gross revenue over time. In applying this factor, external influences such as economic conditions, changes in the public mood, etc., which may affect the sale of artistic or literary works will be taken into consideration, and

    (l) the nature of the literary works undertaken by a writer. It is considered that a literary work such as a novel, poem, short story or any non-fictional prose composition that is written for general sale or syndicated distribution would normally have a greater profit potential than a work undertaken for restricted distribution.

I think I can do this. And if I can’t, then it can be a hobby. As hobbies go, it’s pretty frugal. Besides, I should be able to figure out how to create enough value.

I can do longer and longer experiments with this, easing into it. I’ve committed to consulting for the next four months, so I should do that. I have some illustration clients with ongoing relationships too, so I’ll take care of those needs. I might not take on additional commitments, even for short-term engagements. Then I’ll give this Proper Retirement experiment a try for a quarter, evaluate, and then try it for longer.

What warning signs should I keep an eye out for? If my savings dip below X years of expenses, time to reconsider. If I find myself falling out of touch with my networks, time to focus on reaching out to and helping people I know. If something happens to our financial situations change, I can invest some time in re-skilling and get back into full-time technical work.

The key difference for me is the jump from people saying “This is what I want and I will pay you $X for it,” to me saying “I think it might be interesting to make Y. Let’s see if other people will find it useful.” I’m not really used to that. I’m okay, but I want to be even better at it. Now is an excellent time to learn.