I minimize the number of decisions I care about. What I’m going to do with my life? Big decision worth spending time on. Is something worth it? I can spend hours analyzing the trade-offs. What do I want to eat? I don’t particularly care. I’m trying to avoid decision fatigue. Decisions take up time and willpower. Also, I’m trying to minimize attachment. Everything’s going to be okay.

W- asked me what colour I would like the deck to be. I looked at the dozens of swatches all neatly laid out, and I boggled at him. It’s like when people ask me where I want to eat. Beats me. At least there, I can use a rule of thumb: closest $-$$ place rated at least 3.5 stars on Yelp that’s still open at this time of day and that satisfies everyone’s dietary restrictions.

If I don’t care about the outcome of a decision – if multiple alternatives are not significantly different in terms of their value to me – I’ll tell people I don’t care strongly enough to decide. That way, they don’t mistake a casual opinion for a strongly-held opinion and end up regretting being overruled. If people really want me to participate, I’ll support whatever people suggest, and I’ll help people remember their reasons for or against something. I’ll also ask questions to draw out reasons and make off-the-wall suggestions to add humour.

This is probably not quite what people are looking for. Usually, when people ask for your opinion on something, it’s because they want it.

My default is to not have an opinion. Maybe I should. It’s pretty easy to pick something and then let your brain fill in the reasons for it. People learn more about their choices in the negotiation.

Or maybe I should just have a more structured approach when people ask me about things I don’t have an opinion about. List alternatives, costs, benefits; make diagrams; graph arguments. That way, even if I don’t have an opinion, I can contribute value.

We discussed a few stain options. W- picked one and painted the deck with it. He thought it looked too gray in the sunlight. He stripped it back down and started looking for a different colour. (While I’m easily distracted from finishing my tasks and a big fan of getting things 80% okay, W- is awesome at persistence, and is working on getting around the sunk costs fallacy.)

I don’t mind. It gives me more opportunities to be supportive of projects and experiments, even though I am probably not yet filling the more useful role of the Voice of Reason. I think being able to use the Voice of Reason needs experience anyway. (They say good decisions come from experience, and experience comes from bad decisions. Not that this was a bad decision; it’s just a different outcome.)

I’m going to be asked for my opinion of or recommendation for many many things in life, especially as I move into my thirties. People assume twenty-somethings don’t know very much, except maybe about tech. Thirty-somethings probably don’t know much either, but are expected to have Opinions. Might as well learn.

How do you handle being asked for your opinion when you haven’t given something much thought?

Comic: Cartoonresource via Shutterstock

It’s easy to get discouraged by the vague feeling that you’re ignoring lots of things that you wanted to work on: hobbies that fall by the wayside, projects gathering dust on your shelves, Someday/Maybe lists that grow and never shrink. I’m learning that thinking about what’s on your back burner can help you make your peace with it, deliberately choosing what you want to work on during your discretionary time and letting go of the rest.

I’m focusing on consulting this October and November. Assuming all goes well, December will be taken up by a vacation: wrapping up consulting, going on vacation, and recovering from the whirlwind. I’m going to be less “retired” than I thought I’d be at this point, so I want to be deliberate about what I’m putting on the back burner and what I should keep doing.

Consulting leaves me with one or two days a week when I can focus on other projects. I also have little bits of time here and there, and some time in the evenings. What do I want to fit into those opportunities?

Daily drawing: I really like this practice of thinking about ideas or questions on paper, and I plan to continue doing this. Since I’ve made it a warm-up and cool-down activity, I don’t need a lot of separate focused time for it. I draw to start and end my day, and I spend a little time filing new sketches. Decision: Continue doing this in small pieces.

Visual vocabulary: Someone asked me if I could share my visual vocabulary with people. I had figured out a good workflow for building my visual vocabulary using other people’s sketches, but I didn’t want to share my 1,000+ term collection because it’s based on other people’s sketches (copyright, you know!). So I started building a new visual vocabulary using only my own sketches. So far, I’ve processed all of my sketchnotes from 2013.

The next step is to process my personal sketches (including my daily sketches) from 2013, and then start going backwards in time. Although the work was simple and not challenging, it was a lot of fun reviewing my past sketches and remembering what the talks were about. Decision: I’ll spend a little time on this each week. I thought about outsourcing parts of it, but it’s probably going to be easier, faster, and more useful if I do this myself.

Topic-focused blog/book: I’ve been playing around with the idea of spinning off a separate blog focused on a small set of topics. The poll results were tied between learning/writing/notetaking/etc. and visual thinking/mind mapping/planning/etc., so I’m planning to focus on learning/writing/notetaking/etc. first because that will let me do all the rest even more effectively. Decision: I probably won’t split it off into a separate blog yet, though. I’ll use some of my daily drawing time to explore topics and flesh them out into a series of blog posts – possibly hitting two birds with one stone. =)

Quantified Awesome: I have bugs to fix, features to add, analyses to run… Well, the bug fixes come first. I’m going to set aside some of these focus days or weekends to get token authentication and a few other things working again. I’m curious about my groceries data now that I have more than a year of it, so I’m looking forward to crunching the numbers. Just how much rice do we go through in a year? How can we organize our space to allow us to stock up even better? Decision: Coding benefits from long periods of focus time, so I should use my free days for this. Once I get past the bugs, though, I’m okay with scaling back on this a little.

Server administration, learning new tech skills: My web server isn’t set up optimally. It’s probably slower and more conservative than it needs to be. There are configuration options I haven’t dug into, performance limits I haven’t tested, and so on. Still, my server hasn’t fallen apart recently, and it should be fine for now. Learning new programming languages, frameworks, or platforms might also help me in the long run, but that’s something I can guiltlessly postpone for this quarter. Decision: Postpone, revisit next year.

Delegation and automation: I keep wondering about how I might be able to take advantage of other people’s skills and experiences in order to learn more or do more, but I’ve been slacking off in terms of actually delegating things to people. I’ve been digging into why that’s the case (what are my excuses? am I missing some quick wins?), so you’ll probably see a blog post about that shortly. Still, I don’t want to delegate for the sake of delegating. I want to make sure that I specify work clearly and can pay enough attention to give good feedback as well as learn from the experience. This takes time and brainspace. I’ll dig into this if the opportunity comes up, but I don’t mind waiting until later.

As for automation, I’ll probably learn more about that on the way to doing other things. For example, AutoHotkey looks like it will repay further study. I’ll use some of my focus days to tweak things here and there, but I don’t need to push too hard on this. Decision: Postpone or do opportunistically.

Sketchnote lessons: This is where I teach myself (and other people!) more about sketchnoting by drawing different variants of common techniques. It helps broaden my visual vocabulary. I currently publish a sketchnote lesson every Thursday. If I make it less formal and more playful, I might be able to fold it into my daily drawing / doodling sessions. For example, I might try drawing people in different professions or in different situations as a way of expanding my visual vocabulary. This does require a bit more research, though, because I need to look at other people’s sketchnotes and reference photos. If I relax my expectations of publishing and make it, say, once a month, then I don’t have to worry about scraping the bottom of the barrel. (I should do one just about metaphors… =) ) That way, if I end up ramping up my drawing/doodling so that I have something publishable once a week or once every two weeks, that’s awesome. Decision: Scale back a little, and focus on doodling different categories?

Wrap-up

When I started thinking about what’s on my back burner, I felt a little overwhelmed. There was too much to fit into my week, not to mention the stuff on my Things I want to learn list that I haven’t gotten around to even starting. As I thought about what I could fit into small pockets of time, what needed more focus, and what I could postpone, things felt more manageable. Now I have a few things I can focus on, and I don’t have to feel bad about temporarily letting go of some of the things I was curious about. We’ll see how this works!

There will always be more things you want to do than time to do it in. You can get stressed out by your limitations, or you can exercise your ability to choose. Good luck!

Even with all the research you can do, you can’t remove all the uncertainty from a decision. This is life.

I cheat by making potential outcomes a little bit better with arbitrary conditions, in addition to any intrinsic value I can remind myself about. For example, I might prefer one set of results, but I’ll promise myself sushi if the outcomes don’t go my way. Or ice cream, or playing a video game, or reading, or some time spent writing. Since I don’t have ice cream and other treats that often (that’s why they’re treats), the trick works.

I also try to focus on the intrinsic value of various outcomes. My favourite outcome sweetener used to be “If nothing else, this will make a great story someday,” which is an excellent psychological benefit associated with keeping a blog. (Try it!) Other good ones for me are “Well, if it doesn’t work out, it’s good practice in equanimity,” and “I’m sure I’ll learn something.” I remind myself of that before the uncertainty is resolved so that I don’t feel like I’m sour-graping. Find whatever works for you. That said, sometimes it’s fun to have an actual treat.

This is different from, say, drowning your sorrows in ice cream after the fact. Eating ice cream because you’re sad is one thing; deciding to give yourself advance permission to eat a little ice cream if outcome B happens is another. Or at least it is for me – there’s something about the mental trick of reconciling yourself with probabilities.

While a small concession doesn’t completely make up for not getting a preferred outcome, it takes the edge off. It reminds you that nothing is a complete loss. Being grateful for the small things (even the ones that you’ve intentionally added to the outcome) can help kickstart gratitude for the rest of it. I’m good at enjoying small things, even if they happen because I decided to make them happen.

I also try to not place too much value on specific outcomes. It’s not that A is better and B is worse. They’re just different. Who knows, B might even be better for me in the long run. It’s liberating to face the uncertainty and say, “Well, I’m going to be happy either way this goes, so let’s find out what kind of happiness it will be.”

So this is how I deal with decisions that could go one way or the other: I tack on little treats for myself so that I always have something to look forward to. Even if I rarely end up going down those paths, this practice is great for being optimistic and resilient. It makes life predictably awesome, even when life itself is unpredictable. After all, that’s what consolation prizes are for.

Do you use a similar trick? How do you hack your thoughts and emotions when it comes to uncertainty?

It’s been a little over half a year since I signed up for a membership at HackLab, a makerspace and coworking area in Kensington Market. Before I signed up, I thought about the things I would like to be true at the evaluation point for my experiment, which I set at nine months after I signed up (so November 2013). I figured it would be good to do a quick check so that I can adjust things. Here’s what I wrote in February, and how it has matched up so far with my experience:

I know more about other geeks in Toronto thanks to ambient conversations and helping each other out

HackLab is full of interesting people. I like dropping by and hanging out at the open houses or during regular days.

I’m better at asking people for help when I get stuck, and at setting myself tougher challenges knowing that people can help

I’ve done this a couple of times (keyboard layouts, business questions, web stuff, system administration), although I still need to work on that.

I’ve dug into some of the more difficult things that are easier to learn with other people who can help me. For example: web development, mobile development, electronics

Web development and system administration might be good things to focus on. There are lots of other people who are working on similar things.

I’ve gotten better at sketching ideas, asking other people for feedback, and fleshing out the ones that get people interested

I drew How to Learn Emacs while I was at HackLab. That was fun. =) I’ve drawn some of the sketchnote lessons here, too.

I’ve improved serendipity (test different laptop cues to talk? talk to people about what they’re working on?)

Overhearing stuff works well.

I go to HackLab 1-2 times a week, and sometimes more often if the weather is great.

See analysis below

I’m good at managing my focus (do not disturb / yes, talk to me)

Background conversations interfere with things like typing practice (Plover/Colemak), but I’m okay with listening to conversations while typing (Dvorak), coding, or drawing. Headphones help a little.

I’m good at talking to new people and hanging out with the regulars

Getting there. I feel comfortable around HackLab members and I often have interesting conversations at open houses, particularly over food.

In general, the benefits I’m looking for are:

• Ambient socialization with interesting people
• Ambient exposure to interesting things
• Possible support for learning stuff (ex: Javascript, system administration, Haskell, Python, neural nets, hardware, electronics, 3D printing)

My initial goal was to go to HackLab 1-2 times a week. As of 2013-09-25 (~31 weeks after I joined; I was doing this analysis before the members’ meeting), I have been to HackLab on 41 distinct days. This is within my target range of 31 to 62 visits, and works out to 1.3 visits a week. This is a pleasant surprise, because I started this analysis thinking that I was underusing my HackLab membership compared to my goals. Based on my current attendance, this costs a little less than $10 per visit, which is worth the awesome vegan cooking opportunities / lessons / dinners (Tuesday open houses) and overheard conversations with interesting geeks.

I’m at 66% of the top part of my goal range. What are my current limiting factors, and how can I work around them?

Inertia is powerful and works ways: when I’m home, it’s easy to stay home; when I’m in the middle of working on something interesting on the kitchen table, I don’t want to pack up and bike over. I often sleep in during my non-consulting days, and sometimes I think: “Is it really worth biking downtown for a few hours of hanging out or working?” I’ve also offered to do a couple of extra half-days of consulting each week during September and October, so that limits the number of days when it makes sense to go to HackLab. Besides, introvert mode is pretty comfortable – no distracting conversations, and plenty of good food in the fridge.

So, what could help me make even better use of HackLab? How can I hack my motivation and reward structure to get me out the door?

• Commit to the exercise and treat HackLab as a bonus. At least once a week (Fridays), I will bike for at least 1.5 hours including a mailbox check. I might as well use that biking time to end up at Hacklab, do some stuff, and then take the other 45 minutes on the way back.
• Make Hacklab the centre of my socialization. Instead of setting up separate get-togethers with people, I will funnel people to HackLab’s open house (which I will attend whenever I don’t have other events). If I’m in introvert mode, I will treat the open house as cooking lessons, catch up with people briefly, and relax knowing that people can always chat with other people. If I’m in socialization mode, I will catch up with people.
• Consider small-scale cooking on regular days. Have fun by cooking at HackLab even on non-open house days: merienda? This might be easier once we’ve moved to the new location, with a larger kitchen and a non-drinks fridge.
• On HackLab days, do not open the computer at home in the morning. This gets around the momentum issue. Checking things on the phone is okay, as is working on the computer if something urgent comes up.

What about winter? I’m going to face some motivation challenges when snow makes biking more dangerous and the cold encourages me to stay home. On mild days in winter, I might be able to bike down or TTC down. I can use that as a context switch to write or code. Is it worth $6 to take the TTC down here at least once a week, bringing it to a total cost of $16 or so? Maybe, especially if I move things around so that I’m at HackLab instead of consulting on Tuesdays (or I work remotely on Tuesdays). If I discount winter and consider my membership based solely on my attendance so far, it works out to roughly $15 per day, which is still worth it considering other co-working spaces are $20 for a day pass and don’t offer 24h access, not that I’ve been here at 3 AM. Besides, HackLab does cool things. So yes, I’ll continue throughout winter, and I’ll see if I can get past the activation costs of getting down here by TTC. (Reading time on the subway/streetcar, and travelling during off-peak hours?)

Incidentally, here are the queries that I used to check how many times I’ve been in HackLab:

SELECT COUNT(DISTINCT(DATE_FORMAT(logged, '%Y-%m-%d'))) from access_log where card_id='123-3149';
SELECT MIN(logged) FROM access_log WHERE card_id='123-3149';

Let’s see how this goes!

In the process of experimenting with different types of businesses, I’ve been learning a lot about different types of commitments. There’s a spectrum of commitment-hardness, from very hard (spend money if you have to, but Make This Happen) to very soft (it’s nice to have, but no big deal if it doesn’t work out).

An example of a very hard commitment is speaking. If I commit to giving a talk at event, I need to prepare the talk, and I need to be there. Doesn’t matter if I have a cold. Doesn’t matter if I’m running late because of another meeting and have to hop into a cab. Doesn’t matter if I’m feeling out of it. I need to show up and be professional, which means energy and connection. I can collapse afterwards.

An example of a hard commitment is sketchnoting an event. I promise to be at the event on a certain date, and if I miss that, the opportunity is gone forever. It’s not as big a deal as speaking, since sketchnoting is usually an extra. I write my agreements so that I’m only responsible for refunding the client’s payment if something falls through instead of being liable for loss of business or other costs. I’ve never had to invoke this clause, but I’ve turned down gigs because of uncertainty.

An example of a medium commitment is freelance development. If I’m working with other developers, then I usually need to work at specific times or at a specific pace, but there’s often some leeway in what I can do and when.

Conversations are also medium commitments. They’re scheduled in the calendar, but we can reschedule if necessary.

An example of a softer commitment is illustration. Someone is counting on the images, and sometimes there’s a deadline. I’m free to do the work at a time of my choosing, though, aside from the occasional meetings that are more like hard commitments.

The kind of consulting I’ve settled into is another example of a soft commitment. I have a few meetings (usually mid-day or early afternoon), but I have a lot of flexibility in terms of how many hours I work each week. We keep a long, prioritized list of things to work on, so I can usually choose what I want to work on at a particular time.

Writing is a very soft commitment. No one cares when I do it, so I can write whenever I want. I can write a whole bunch of posts in one day and spread them out for consistency and variety. I can slowly accumulate thoughts or resources for books. I care about writing at least a little bit each week, but that push comes from me.

Oddly enough, compensation isn’t always proportional to the hardness of the commitment. Most of it has to do with the underlying skills rather than how strict the commitment is.

I vastly prefer softer commitments over harder ones. Some of the things I’m working on have unpredictable schedules, and I’d rather be able to reschedule or move things around if something comes up. I minimize the number of hard commitments (business or personal) I need to plan for, and keep a stock of soft commitments that help me take advantage of spare moments. Soft commitments make it easier to match interest or energy with choice of activity, so it’s easier to focus and get things done.

I’ve been taking on fewer events, working on consulting and writing instead. After all, if I can get away with it, why not work with less stress and more happiness? =)

I’m approaching the end of my second fiscal year. (Hooray!) I thought I’d review my decisions for reinvesting profits, plan ahead, and ask for feedback. Here’s how I reinvested some of my profits this year:

• Tools and education:
  • I bought $289 worth of books, including pricey but useful books on drawing emotions and stick figures (Bikablo, from Neuland). I’ve made the most of them by reading, taking notes, and sharing what I’ve learned, so this was definitely worth it.
  • I also took the AlphaChimp Rockstar Scribe course (CAD 298.66, it’s now USD 497; affiliate link). I picked up a few tips on digitizing scanned sketches (lesson 6: digital documentation). The exercises also prompted me to put together my 3-word life philosophy and my 5-year plan.
  • Next steps: My laptop should be good for another year or two, so I have no major upgrades planned there. I may invest more into courses. These tend to be bigger commitments, but I think the experience might be worthwhile. I can test this by seeing if I can improve my retention in free or low-cost courses (Coursera, Udacity) before going on to more expensive courses. Gotta build up those study habits! If I find that I’m hitting the limits of what I want to learn in group classes and I’m already making the most of the Q&A or mentoring that courses tend to offer, then I can look into getting a one-on-one coach.
• Connecting with people:
  • The biggest chunk here was flying to London for the Emacs Conference, which was a great way to connect with people, create resources, and develop skills.
  • I also signed up for HackLab ($51.75 a month) as a way to connect with other geeks and have a place to work at when I’m downtown.
  • I attended networking events ($170.45). AndroidTO was less useful than I expected because I hadn’t actually been developing stuff then, although it was good sketchnoting practice. The Third Tuesdays Toronto events were definitely worth it for me. Rotman events were okay.
  • I met four people for lunches/dinners and had lots of tea with others, talking about mentoring or business opportunities.
  • Next steps: I want to focus on virtual connections, because there are lots of interesting people out there. This means ramping up my scheduling, inviting people to reach out, and reaching out myself (possibly appreciating people with gift certificates or donations to charity)
• Delegation:
  • I greatly increased my delegation budget compared to last year. I subcontracted $1,333.34 of my work and delegated an additional $2,030.30.
  • Hiring a virtual assistant to help with scheduling really helped me get past the hassles of booking people. Worth it.
  • Hiring a transcriber for my podcasts and presentations worked out well, too.
  • Hiring a local consultant to help me brainstorm was okay, but not amazing. It was a helpful nudge to work on my marketing, though.
  • Hiring another on-shore consultant to give me feedback on my website and e-books was also okay but not amazing. It was great for pushing me to add more hand-drawn elements to my website, though.
  • Hiring a developer to work on Rails prototypes gave me a leg up on dealing with various APIs, although I ended up not pursuing the projects.
  • Next steps: Virtual assistance gives me a low-cost way to experiment with and learn more about delegation. In addition to ODesk, I should experiment with Fiverr, Guru, and other sites.

I made $90 in e-book sales in FY 2013, which absolutely delights me. It’s a tiny fraction of what I make in consulting or even sketchnoting or speaking, but it’s a start. I’ve been moving towards a Pay What You Want model so that everyone can get access to the resources and people can show their appreciation by funding future experiments. My experiment-related savings take care of my living expenses, so everything goes to Making Stuff. I want to focus on making more things.

For this coming year, I’m planning to focus on consulting until it winds down. I’m also going to ramp up creating content: blog posts, drawings, articles, e-books, courses, and more. I often get requests to sketchnote events or other people’s content, and I’d like to refer those to other people instead of handling them myself. That way, I can help other people grow, and I can make myself learn more about creating my own content.

Ideally, by September 2014, I’ll have:

• a separate topic-focused weekly blog with evergreen posts and useful, well-formatted, illustrated articles
• several e-resources for that blog
• a mailing list that I’ve learned how to use
• and possibly a course that includes tips, worksheets, checklists, animations, and video

I might keep a "Wanted" list on my site so that I can funnel other requests to it, like people looking for sketchnoters. That way, instead of simply telling people no, I can help them a little further along the way and help other people grow their businesses too.

Here’s my plan for getting there:

1. Brainstorm headlines and article ideas to help me choose which topics I want to start a weekly topic-focused blog around.
2. Get feedback on which topics people would like to read about first. Start collecting e-mail addresses for launch.
3. "Bank" 4-8 good articles (write two months ahead). Invite early readers.
4. Publicize it a bit more widely once I’ve gotten into the rhythm of publishing on the blog and I know that the rate is sustainable.
5. Plan an outline for a brief e-book and gear my articles towards that.
6. Reach out and find guest posting opportunities once the blog is more established.

To make the blog different and useful, I plan to illustrate the ideas with one-page cheat sheets / references. This will also make a handy collection.

With that in mind, what are some ways I can reinvest some of my profits in order to make things better, and which ways make more sense than others? These are ordered in terms of how useful I think they will be, with the best ones on top. I’d love your feedback and suggestions!

• Find a system administrator who can help me review my config and backup plans, and who can answer questions from time to time. As someone said, good judgement comes from experience, and experience comes from bad judgement. I can learn things on my own, but it’s probably really good to take advantage of other people’s hard-won experience too. That way, I have a solid platform to grow on.
• Go through a course like the ones offered at Platform University, CopyBlogger, or ProBlogger. I can get multiple levels of value out of this. First, there’s the lessons themselves. Even if I know most of the basics because I’ve been blogging for more than ten years, it will be good to deliberately go through them. I can turn them into blog posts about my experiences applying those tips. I can turn them into sketchnotes and references. Along the way, I’ll also learn about the structure of courses and communities – what I like or don’t like, and what other people seem to respond to.
• Sign up for a good mailing list service, possibly with an autoresponder or digital delivery mechanism. This will give me more control than simply using FeedBurner to give people e-mail updates.
• Sign up for survey tools so that I can get better feedback. Provide giveaways or incentives for survey completion.
• Experiment with richer media: presentations, animations, podcasts, video. Buy tools and hardware. Possibly delegate editing. Podcasts and screencasts might be a good way to work myself up to doing webinars regularly.
• Pay for a web conferencing service, and set up regular web conferences or webinars. Monthly webinars might justify paying for a premium service so that I’m not constrained by Google Hangout or AnyMeeting’s limitations. I can also use this to interview people. Any recommendations for a cross-platform webinar service that allows all participants to chat with each other?
• Work with a reputable SEO company to avoid penalties for duplicate content and to learn more about doing keyword research. Sometimes little tweaks make things more findable or discoverable.
• Invest in better web planning and design, maybe for the topic-focused blog. I might start off with a basic template, fill it in with content, add some resources, and then go for a more professional design when the topic and audience for the blog has firmed up a little. That way, I can get feedback from people too.
• Buy premium plugins, scripts, or themes to make navigating the blog or content easier. A responsive theme and a good gallery can make a lot of difference.
• Buy books, read them, and give them away. That way, I’m not limited to the library’s selection. The library has lots of books and it could take forever for me to get through the backlog, but learning from and sharing tips from newly-published books may create more value for readers. Plus, if I set aside a budget for shipping (which is expensive in Canada!), I can give lightly-read copies away. I’ve had publishers send me copies of books to review, so maybe I can ramp that up also.
• Hire someone to format e-resources. They can help develop the template, lay things out nicely, and make sure it fits in well with the blog.
• Learn how to work with article writers or pay for excellent guest posts. I have the time to write and I enjoy writing, but I’m curious about the perspectives that other people might bring.
  • Worst-case scenario: They write the first draft, and I end up rewriting it extensively because I have a better idea of what I don’t want.
  • Best-case scenario: I give them a topic to write about, they come up with insights or research I might not have come across myself, and then I can personalize it with more stories or experiences.
• Work with copywriters and editors and get better at writing.
• Hire a coach to help me learn more about planning posts, creating resources or courses, building a community, and so on.
• Buy domain names and learn how to set up landing pages.

Image credit: Piggy bank (Oliver Hoffman, Shutterstock)

Following up on my Accelerated Learning chat with Timothy Kenny, where someone asked how I made the decision to go on this 5-year experiment with semi-retirement:

It might surprise you, but I consider myself pretty risk-averse. I don’t bungee jump. I don’t ski. I don’t even drive. I spend hours and days analyzing decisions. I make contingency plans. I take small steps.

So, how does someone like me end up taking a left turn away from a promising career (great ratings, wonderful opportunities) for a 5-year gap in employment as an experiment with semi-retirement?

I’d been thinking about something like that ever since I started working. I knew I wanted to learn about starting businesses someday. My parents built their own advertising photography studio, and although they worked long hours, they were happy. I grew up reading books about management and accounting—ever since I was tall enough to pull them off my mom’s bookshelf.

When I graduated with my master’s degree and started working, I consciously resisted the pull of lifestyle inflation. My expenses were much like the one I had as a student: I rarely ate out, and I bought my clothes on sale and second-hand. An excellent public library meant I could keep my book and entertainment budget under control.

I was excited by the idea of being able to finally apply the advice I’d read in personal finance books. I maxed out my Registered Retirement Savings Plan contributions and put a tidy amount away for other long-term investments. I knew my tendency was to scrimp and save, so I also made room in my budget for two things: a play fund, and an opportunity fund. The opportunity fund would be for learning how to make better decisions and take better risks.

Many of the decisions I made with the opportunity fund paid off, encouraging me to try more. I bought a tablet, and then a tablet PC. I bought books, went to events, tried out stuff, treated people to lunch so that I could pick their brain. As I gained confidence, I wondered: how can I make the opportunity fund even more liberating?

I redoubled my focus on saving, channeling more into the opportunity fund. I looked at my expenses, too. I’d been tracking my finances since 2005, so I had a good idea of how much I spent on average. I started learning more about businesses. I came across the statistic that ~80% of businesses fail within the first five years. If I could free myself from worrying about cashflow for five years, I’d probably do all right – and even if I messed up and had little to show for it, I’d still be doing about average. If I totally messed up? Well, I’d probably still be ahead of where I should be at my age.

Besides, I hadn’t read about a lot of other people giving this kind of experiment a try. If I could muster the time, space, and guts, I might as well learn what I could with the opportunity.

It was not an easy decision. I knew many people who were struggling to find work, or who were unhappy with the work that they had. Technology companies tend to discriminate against older people. Would I waste the prime years for building an amazing career? Would I find it difficult to re-enter the workforce if I wanted or needed to, such as if something happened to W- and we needed a steady income?

I talked to W- again and again, threshing out the possibilities and risks. W- supported the idea. It made sense to try this out, and this was as good a time as any to do so. We didn’t rely on my income for mortgage payments or other constraints. We have a decent public healthcare system, and he had extended health benefits through IBM. We didn’t have any young kids or sick family members who needed care. It was better to learn now than to wait until I had to.

The bigger risk would be to not learn how to create value on my own. If I could learn how to make stuff that other people found valuable, if I could learn how to use my time and energy even more effectively—to learn, share, and scale up—then I could help W- learn these things if his situation changed. And it would probably change someday, so it’s better to prepare for that.

What were the real risks, anyway? I have a lot of fun learning and tinkering. I figured I’d be able to keep my technical skills sharp, and maybe I might even pick up a few other marketable skills along the way.

Sure, the employment gap might turn off some employers. Some of my freelancing friends were going through rough patches, and they told me how employers looked at them askance (“Is this guy going to take off and start his own company again in a couple of years?”) I figured that if I really needed to re-enter the workforce, I could probably come up with a coherent story for these five years. I knew I’d take notes along the way, and I had a lot of practise using weekly reviews to remember what I learned or accomplished. The brain is excellent at rationalization, and I’m sure that in 2017, I’ll be able to explain my experiment in a way that makes sense.

One of the lessons I learned as a teenager was not to get paralyzed by the thought of my “potential”. Sure, if I leaned in with all I had, I might reach the corporate or entrepreneurial stratosphere. But really, I don’t need that much. I just need enough, and enough can be incredibly liberating.

My opportunity fund approached my 5-year target, and I firmed up my plans. I considered ratcheting down work: maybe 75% part time, then 50% part time, then 25% part time, then fully “retired”. With IBM’s intellectual property agreements, it was easier to just make a clean cut. (I ended up doing the ratcheting-down with consulting anyway… funny how life works!)

At the one-one-one meeting with my manager where he shared the results of my annual performance review (yay, top ratings!), I told him I was planning to leave the company and experiment with other things I wanted to learn. Since I gave a few months’ notice, we had plenty of time to cleanly wrap up projects. And then I was off on my own.

This experiment gets less and less scary the more I get into it. Sometimes I look at my numbers and wonder whether I can actually take bigger risks than I currently feel comfortable with. I’m getting better at thinking my way through decisions with greater uncertainty or impact, turning to research, role models, and reflection to get myself through it.

If you’re thinking about making a similar decision yourself, these tips might help:

Think about the real risks you’re worrying about. How can you mitigate them? What are the worst-case scenarios, and how can you work around them?

How can you create a safety net for yourself? What can you do to build your confidence and rescue you from some of those worst-case scenarios?

What are some small steps you can try? I didn’t jump straight into semi-retirement. I started by taking smaller risks and learning from them.

Even now, I take very few risks: I overpay my taxes in order to minimize the impact of calculation errors, I don’t claim tax credits I’m not sure about, I’m conservative about my business commitments and contracts.

If it looks like I’ve come far, it’s only because I go one small step at a time. It’s… kinda like the builders in Lemmings, building steps until you get to where you want to go? =) And then other people can go up those steps and reach their goals more easily, or be inspired and build steps of their own.

(screenshot from http://tomato17.tripod.com/gameroom/fun07.html)

Related posts I think you might like:

• How hacking my wants helped me experiment with “early retirement”
• Experiment pre-mortem: Imagining and dealing with causes of failure
• Seeing the futures
• Dear Future Sacha, in which I remind myself that the reason you make a safety net is so that you can fly.

Good luck!

(Hah, my current hack for coming up with blog post titles is to just squish many potential titles together. Sorry. Maybe you can give me feedback on which sub-title you liked most! )