Category: Books

Getting the Need for GTD

I seemed to have hit an inflection point in my job recently that I’ve been struggling to overcome. While my work has had multiple buckets of concern, I’ve been able to managing things fairly well using my memory and jotting notes and to-do’s in my notebook. However with moving into a position that requires managing complex, long-term, and poorly-defined processes, I’ve been increasingly finding it difficult to keep everything straight in my mind. My tasks aren’t are clearly defined, and I’m required to be more independent in how I manage both my own personal workflow and the various areas under my responsibility.

Simply maintaining a to-do list doesn’t seem to cut it anymore. There is too much to keep track of, too many legacy pieces of information that has accumulated over time, and the pace at which things are added or change is steadily increasing in velocity. Add to this the need to keep on top of things in our personal life at home, volunteer work, and activities that I find gratifying, and I’m feeling slightly paralyzed in knowing what I should fix my attention to.

In an effort to get a handle on things, I’ve picked up David Allen’s Getting Things Done. It’s the first time in a while where it feels like the text is speaking to me. I went into the book a little leery of going after yet another gimmick or shiny new toy. GTD is a seminal system in the productivity space, and so it sometimes carries with it some baggage from some of the more problematic areas of the space. Yet, I’ve found it helpful so far in thinking through my problems. At its core, my problem is in two areas: the meaningful transformation of input, and in execution.

I suppose GTD will eventually help me with the latter (I don’t know – I haven’t finished the book yet as of writing), but it’s been incredibly insightful in tackling the former. I tend to take notes and capture to-do items all over the place. However, what I’ve been lacking is examining each of these pieces of input and doing something with it; processing them into their buckets. The list has grown so large and unwieldy that I am having trouble finding stuff when I need it. I have tried popping items into information systems like Notion, Trello, or using tags to help me find it later, but most of these systems have lacked the context to help make the inputs useful later. Instead, they sit in whatever capture system was used to grab them at the time – physical notebook, email inboxes, Trello, tags in OneNote, calendars, or tasks in Teams.

I’ve found GTD helpful in suggesting organizational structures and parse out what will be meaningful later and what can be archived out of mind. I’m still working through developing a system, but so far embracing ideas from GTD has helped keep things more readily at the top of my mind, which has translated into less general anxiety as I go through the work day.

Stay Awesome,

Ryan

Stepping Back Into The River

As the saying goes from Heraclitus, you can’t step in the same river twice. There are two ways we can interpret this metaphor. The most common interpretation is that you cannot step in the same river twice because the river is constantly changing. The water is flowing past, the flux of the water is changing the boundaries and composition of the river, and so it’s impossible to step into the exact same river twice. But another way to interpret the metaphor is to place more emphasis on the you – You can’t step in the same river twice – whereby the you stepping into the river changes and is not the same over time. This can be taken as literally as when describing the flux of the river – your cells are changing, etc. But I like the more poetic version of the metaphor that speaks to us changing with our experiences through our lives.

When you return to a river (the river being a stand-in for any number of things), you are a different person, and your past experiences make the phenomenological event that you experience different. The first time I encountered this was retaking a course in high school. I was the kid that took a course called Writer’s Craft, loved it and the instructor so much that in the following year I enrolled in it again with the same teacher. However, the materials selected for the class by the teacher, and indeed my fellow students, were all different. It was different, less enjoyable this time around. I still enjoyed studying under my teacher, Mr. Steffler, but with it being a different cohort of students (students from the grade below me), I realized that the experience lacked the magic of when I took it with my original cohort. I tried to step in the same river twice and was surprised when it was different; that I was different.

There is also the case where you revisit a book you read previously and it speaks to you on a different level. Maybe your experiences help you connect with the characters on a different level, or you empathize with the characters differently. Your values might have changed. Or just that you are older and more knowledgeable, you understand more of the text and draw different connections.

This happened to me recently. My job promotion at work was approved, and I’m taking on management tasks as part of my portfolio. Maybe because I have mild imposter syndrome (I sometimes believe I am continuing to fail upwards), or maybe because I’m trying to be proactive, I decided to pull my copies of books by Peter Drucker off the shelf to learn what it means to be in management and how to do it well. I started with a short text of his called Managing Oneself, which I read back in 2017.

Something in the book landed differently this time, which I think breaks down to two differences about me now versus who I was five years ago. The first is I am busier now than I was then. This isn’t to say I was idle then – I was working three jobs, heading up a non-profit, in a relationship, etc. However now my life feels fuller with things that feel more critical – a higher stakes position at work with more responsibility, co-managing a household with my wife, the responsibilities of family and childcare, dealing with a pandemic, etc. I might have fewer work domains on my radar than I did in the past, but things have higher stakes now, and the idea of more effectively managing myself speaks to who I am as a person, where I’m trying to be mindful of others, plan for the future, and lay down a good foundation to support our family as we go.

The second thing that landed differently was the section about learning more about yourself and how you operate as you manage yourself/your life. I don’t remember this sticking in quite the same way (and based on my blurb from Instagram, it seems I was slightly underwhelmed by the text). For as much as I feel like I’m an imposter sometimes, I also know myself more now, am more confident in my skills, and have cultivated experience and expertise as I travelled along my career path from then until now. And so to revisit this section about managing yourself (that is, identifying what you should prioritize your focus on nurturing and developing) speaks to me. Rather than being frenetic and jumping on every opportunity while you are early in your career, it is better to slow down, be mindful, and think through what will add value to your life.

I don’t need to worry about losing out on opportunities by not acting fast. Instead, I can think about enhancing quality, enriching life, and paring down the things that no longer serve me.

I thought I was going to read the book a second time to remind myself of its content. Instead, I realized I was coming at the book afresh, for the first time, ready to learn.

Stay Awesome,

Ryan

Feeling Your Way Into An Answer

I was listening to a podcast late last year where author/speaker Michael Bungay Stanier was on to promote his new book. The podcast host asked him a question, and Stanier prefaced his response with something to the tune of “I’m not sure how I think about that since I’ve never thought about it before, so please allow me to feel my way into the answer.“

This really stuck with me over the last few months as it gives me words to describe something I’m somewhat known for. Whether it’s for my work with engineering accreditation or for the research ethics boards I sit on, whenever I’m asked to opine on a matter of interpretation, I’ll often externalize my thinking to help sift through the relevant details or principles at play. I’d like to think I do this as part of teaching the other person how I reason through problems, but I think it’s more charitably the way I test ideas out slowly and give language to thoughts or ideas that are more emotionally based in my mind.

I suspect this is an offshoot of my training in philosophy, where if we cannot deduce an answer through deductive reasoning, then we employ inductive and abductive strategies to generate thought experiments. I craft a set of considerations or scenarios, say them out loud, and evaluate if it satisfies the criteria, and check to ensure there are no counter-examples, counter-factuals, or missing considerations that should be accounted for.

I’m under no illusion that this can be frustrating for someone looking for a simple answer; brevity is not one of my virtues. However, having this phrase to describe how my mind works makes me feel slightly less embarrassed when I’m talking my way into an answer.

Stay Awesome,

Ryan

What I Read in 2021

book lot on table
Photo by Tom Hermans on Unsplash

The calendar has rolled over, meaning it’s time to provide an update on my reading over the last year. For my previous lists, you can see what I read in 2020, 2019, 2018, 2017, and 2016.

TitleAuthorDate CompletedPages
1ClanlandsSam Heughan & Graham McTavish01-Jan352
2Lean OutTara Henley03-Jan336
3Moon of the Crusted SnowWaubgeshig Rice05-Jan224
4SovereigntyRyan Michler12-Jan266
5Eat a Peach: A MemoirDavid Chang14-Jan304
6NeverwhereNeil Gaiman19-Jan480
7The Office: The Untold Story…Andy Greene24-Jan464
8Angels & DemonsDan Brown30-Jan736
9*MeditationsMarcus Aurelius07-Feb256
10The PracticeSeth Godin23-Feb272
11*The Righteous MindJonathan Haidt12-Mar528
12A Clash of KingsGeorge R.R. Martin29-Mar1040
13Hold Me TightDr. Sue Johnson26-Apr320
14*To Pixar and BeyondLawrence Levy26-Apr272
15Cool SexDiana Richardson & Wendy Doeleman30-Apr128
16MindfuckChristopher Wylie10-May288
17*The Massey MurderCharlotte Gray24-May336
18*On ImmunityEula Biss21-Jun224
19At The Existentialist CaféSarah Bakewell30-Jul448
20Learn Like a ProBarbara Oakley & Olav Schewe05-Aug160
21The Great InfluenzaJohn M Barry05-Aug560
22The New FatherArmin A. Brott07-Aug336
23EffortlessGreg McKeown07-Aug272
24Can’t EvenAnne Helen Petersen13-Aug304
25The Happiness HypothesisJonathan Haidt13-Aug320
26SwitchChip Heath and Dan Heath16-Aug320
27The Bully PulpitDoris Kearns Goodwin22-Aug912
28Saving JusticeJames Comey22-Aug240
29An Elegant DefenseMatt Richtel27-Aug448
30Infinitely Full of HopeTom Whyman06-Sep218
31*The Black CountTom Reiss22-Sep432
32Think AgainAdam Grant01-Oct320
33Lives of the StoicsRyan Holiday and Stephen Hanselman03-Oct352
34*A Knock on the DoorTruth and Reconciliation Commission of Canada06-Oct296
35Our Own Worst EnemyTom Nichols07-Oct256
36A Storm of SwordsGeorge R.R. Martin11-Oct1216
37How Ike LedSusan Eisenhower17-Oct400
38Braiding SweetgrassRobin Wall Kimmerer29-Oct408
39*Social EmpathyElizabeth Segal05-Nov256
40NoiseDaniel Kahneman, Olivier Sibony, Cass R. Sunstein09-Nov464
41Finding Your ElementKen Robinson with Lou Aronica12-Nov320
42The StorytellerDave Grohl14-Nov384
43Why We Make Things and Why It MattersPeter Korn16-Nov176
44For Small Creatures Such As WeSasha Sagan18-Nov288
45Courage is CallingRyan Holiday24-Nov304
46*The Seven Principles for Making Marriage WorkJohn M Gottman and Nan Silver06-Dec288
47Mr. Dickens and His CarolSamantha Silva08-Dec288
48The Ghost of Christmas PastRhys Bowen14-Dec272
49Why We SleepMatthew Walker19-Dec368
50In A HolidazeChristina Lauren20-Dec336
51Christmas Every DayBeth Moran24-Dec408
52A Christmas CarolCharles Dickens24-Dec112
Total19308
Entries whose number is asterisked was read for our bookclub.

This year was a huge step up in the number of books I got through. In 2020 I came in at 38 books, whereas I settled into a good groove and managed 52 books for 2021, or a book per week on average. The big months were January (8 books), August (10 books), and October through December (7 books each month). 2020 was a tough year on everyone as we made the pivot to pandemic life; I was also preoccupied with my wife’s pregnancy and later the birth of our son. For 2021, things settled and we found new normals to operate within. I still relied heavily on audiobooks, but I found that where I made the majority of my reading progress during my work commutes in the before-times, I now find time while walking the dog and doing chores around the house to squeeze in a listen.

I’m also happy to see I continued my trend started in 2020 to move away from predominantly reading self-help and business books. While they are still sprinkled throughout, I embraced more fiction, memoirs, books on history, and discussions of complex social issues.

My book club was down slightly over last year, coming in at 9 books for the year. We also celebrated a birth and added a new member which is exciting. In the table above, the asterisked numbers denote book club entries, but I have included them collected below:

  1. Meditations by Marcus Aurelius
  2. The Righteous Mind by Jonathan Haidt
  3. To Pixar and Beyond by Lawrence Levy
  4. The Massey Murder by Charlotte Gray
  5. On Immunity by Eula Biss
  6. The Black Count by Tom Reiss
  7. A Knock on the Door by Truth and Reconciliation Commission of Canada
  8. Social Empathy by Elizabeth Segal
  9. The Seven Principles for Making Marriage Work by John M Gottman and Nan Silver

And to round out the post, here are my top five reads of the year in chronological order:

  1. Moon of the Crusted Snow by Waubgeshig Rice (this book was so good, I bought two copies and mailed them to friends as gifts – one going all the way to Scotland!)
  2. The Great Influenza by John M Barry (if history doesn’t repeat itself, then at the very least it rhymes, and so learning about the Influenza Pandemic of 1918-1919 helps to contextualize our experiences over the last two years)
  3. How Ike Led by Susan Eisenhower (I took so many notes reading this book and will revisit the lessons of Dwight Eisenhower often)
  4. Braiding Sweetgrass by Robin Wall Kimmerer (this was my first proper introduction to Indigenous ways of knowing, and my worldview has been made richer for it)
  5. Why We Make Things and Why It Matters by Peter Korn (a beautiful memoir and reflection on the nature of making, craft, art, and finding your calling within a career)

2021 was a great year of reading for me. Despite feeling adrift in the monotony of the pandemic (or languishing, as Adam Grant claims it), I found exploring both ideas and fictional worlds to be immensely rewarding. My horizons have expanded and I’m looking forward to continuing this exploration into the new year. I’m intending on tackling more biographies, books on history, and works of fiction. I’ve also decided to explore another genre – comic books! With all the great media being adapted from comic books (and now that I have disposable income), I’m intending on diving into some of the celebrated collected volumes that I missed out back in my Wizard reading days.

Happy New Year!

Stay Awesome,

Ryan

Leverage

I’ve been reading ‘self-improvement’ books for the last five years. Some of those books dealt with financial and life management, where you leverage the money you earn to create more value for yourself. But until you reach that point in your life, it’s only a theoretical exercise to engage with – there is no point in thinking deeply into investing options or buying your way into freedom until you have money to buy options. I’m sure there are self-improvement adherents who will vehemently disagree with this, but the reality is you aren’t going to gain access to the game by saving money not buying lattes or avocado toast unless you are playing a really long game with a lot of good luck.

I’ve now hit a point in my life where options have opened up for my family, and we can make choices and trade-offs to build out a lifestyle that works best for our goals. This is not to say that all options are available to us – we have to carefully look at the tradeoffs and determine whether the downsides of any option are something we are comfortable living with (e.g. to pay for a given option, should we, say, reduce from two cars to one).

Part of this exercise is critically examining each of our assumptions and systems to determine if they are moving us towards what we want, or if they need to change to better align with what we want. This is where the concept of leverage has entered my mind, because when evaluating costs or expenses, it’s important to note that not all expenses are net negative. Some expenditures end up buying more value than what we spend on them.

This is the game in a nutshell – you trade your time for money. Money represents quantified time and effort that can be exchanged in markets with mixed goods. I spend time at work and my employer gives me money in return. I then take that money to purchases goods or services.

Until now, most of the way I thought about the game was surface-level transactions of 1:1 value transfer – I work x-hours for y-dollars. I then trade y-dollars for a good or service with a transactional value of y-dollars. I haven’t really given much thought to the value (that is, how much I value it subjectively) of the good or service provided back to me, and whether that value is higher than what I’m spending. I suppose I’ve thought about it in an abstract way, such as I receive more enjoyment from the thing than the money I spent on it; the opportunity cost is not higher than the value I’m getting from it.

By focusing on the surface-level transactions, the only metric that was critical was to ensure the revenue was not exceeded by the expenses, that I wasn’t spending more money to buy value than I was getting in exchange for my labour. It’s worked up until now, but the direction my family wants to head requires me to think more deeply about what those expenses are buying us.

Ideally, I should be seeking to engage leverage – I trade time for money, then use the money to buy time in greater quantities. What might this look like?

  • With my wages, I can lease or own a car. The money I spend on the car frees me up to commute to work on my own terms. I could get to work more cheaply, such as public transportation or cycling (ignoring environmental costs in this calculation), but then I’m trading cost for time. Having my own vehicle is more convenient, more comfortable, and faster, allowing me to maximize time at work and time at home.
  • With my wages, I can pay for cleaners to clean my house. This frees up more leisure time and cuts down on bickering in the house. It is cheaper for me to buy the supplies and do it myself, but I value the leisure and time with my family more than the cost.
  • With my wages, I can pay for daycare for our child. My spouse or I could quit our job to care for our child at home full time and save the money. However, the money we spend on childcare frees us up to earn multiples of what we spend for the childcare – e.g. at $1,000/month, we would spend $12,000/year for daycare so that we can make north of 5x of that in our jobs.

This is not an easy exercise as many of our expenses feel necessary on the one hand, or scary large in context. However at this point in our lives, we have to accept that our raw effort will only diminish (I can’t work all-nighters like I used to without significant physical cost), and there are no more hours in a day we can squeeze out through discipline and efficiency. We must now turn to leverage and force multipliers to translate what we have into higher value.

Stay Awesome,

Ryan

The Beachhead

A friend who recently was appointed CEO of a company called me this week looking for a soundboard to sort out ideas he had in his head about how to proceed with company operations and strategic direction. The company is looking to shift strategic priorities, and he was looking for an outside voice to make sense of the new direction in relation to the legacy systems he’d need to grapple with.

One of the topics that came up reminded me of a concept I learned about while reading Susan Eisenhower’s book about her grandfather’s time during World War 2 and his subsequent Presidential years.

At two times during Dwight Eisenhower’s tenure in significant leadership roles, he had to create a beachhead to establish his forces (literal and metaphorical) to push towards his objectives. During the war, Operation Overlord’s first phase was to establish a beachhead in Normandy to create a defensible position to allow Allied Forces to work their way into Europe to push back Germany’s army. Establishing a beachhead is critical to success, but is often difficult for offensive forces to complete as the defending force usually has the upper hand in terms of resources and strategic positioning. While the offensive forces need to both set up a foothold and protect its lines to allow more troops to arrive, the defending forces merely have to reinforce it’s occupying positions to clamp down on fresh troops from joining the beachhead. Once the effects of first-mover advantage wears off, the offensive force must contend with protecting supply lines, fighting active defense from the opponent, and pushing past inertia to avoid grinding to a halt in order to win. Once established, a successful beachhead serves as a ratchet for the offensive force – the location of which all future offensives are launched from, and from which the troops need not backslide past. Traction is gained, and the army moves forward.

Similarly, during Eisenhower’s presidency, he saw the importance of passing civil rights legislation, but saw the difficult uphill battle that would needed to both move the country towards accepting civil rights AND enshrining those rights in law (turning both hearts and minds of the nation). While he would have aspired to complete civil rights equality in his time, he knew that if poorly planned, then history, culture, and opposing interests would ensure that forward progress towards equality would halt. Instead, he sought to establish a kind of metaphorical beachhead for civil rights, working on government programs and legislation that would lay the foundation for future leaders to take up and ratchet their work – allowing the movement to progress forward without worrying about losing traction and backsliding.

In listening to my friend, I noted that he also needed to take this lesson from history and focus on his own beachhead. While we think that a CEO is all-powerful in terms of exerting their will over the company, we must also face the reality that comes with working with legacy systems and people. Change is difficult and slow, and when poorly executed either stalls from inertia or alienates your workforce. And so I suggested he take a leaf from Eisenhower’s example and focus on what his core objective is that is reasonable within the timeline he’s being given, and focus on establishing a beachhead to deliver value back to the company president.

Since reading about Eisenhower, I’ve thought about my own beachheads – what are the areas of my life that I must focus on to ensure I’m moving forward with my goals, whether they are family, work, health, or passions. It is still very much a work in progress, but I want to find those areas that I can carve out and secure so that when it’s time to take risks towards my goals, I have a safe space to launch from.

Stay Awesome,

Ryan

The Last Person to Know Everything

On a recent CBC podcast episode about Leibniz and Voltaire’s thoughts about evil and God, one of the interviewees referred to Leibniz as “the last man to know everything.” I find this notion utterly fascinating. Upon hearing that title, I jumped online to search for the “best biography on Leibniz” and found a highly acclaimed book detailing an intellectual biography of the 17th-century thinker. Once I clear some books on my current reading list, I’ll dive into this hefty book.

“Leibniz: An Intellectual Biography” by Maria Rosa Antognazz

This isn’t the first time I’ve encountered the moniker of “the last person who knew everything.” In fact, that was the title of a biography I read back in late 2018 on Enrico Fermi.

I’ve been drawn to this idea for a long time, probably originating with the first time I saw the 1994 film Renaissance Man starring Danny DeVito. That was where I first learned of the term renaissance man, or more commonly known as a polymath – a person with considerable knowledge and expertise across a wide variety of domains. While I wouldn’t quite call it a goal, this is an aspiration of mine since I was a child.

I suppose as the sciences progress, it becomes increasingly difficult to lay claim to being “the last person who knew everything.” Each field grows increasingly complex as we push the boundaries of the known world, which raises the threshold higher of what counts as expertise.

It would seem we need to seriously consider the observation recently made by Professor Adam Grant on the differences between experience and expertise:

Instead of seeking to always have depth of knowledge, perhaps we should give equal consideration to wisdom and how we can apply our experiences and expertise to solve interesting problems. While more nebulous as a goal, I think it steers us in the right direction. At the very least, it’s a good vision to aspire towards.

Stay Awesome,

Ryan

PS – an unexhaustive list of the traits that distinguishes a “last person who knew everything:”

  • Intellectual curiosity
  • Intellectual humility
  • Interests spanning a variety of domains, both sciences and arts
  • A grasp of the methods and tools of science
  • Generating novel insights
  • The ability to see problems in terms of first principles
  • Engaging in idea arbitrage
  • Focus and flow in work – liking what you do

Shrinking the Change

In recent weeks, I’ve built reading time intentionally into my work day. I’ve had it “in my calendar” for quite a while as an intention, but I haven’t meaningfully engaged with that blocked-off time since I first put it into my calendar. The intention was to recognize that my skills and career path would require me to commit time to learning and personal development, but I quickly got lazy and found other less productive things to occupy that time with.

I was annoyed with how I’d allow the whole day to slip by without getting a good start to my tasks (my vice being YouTube’s algorithm), so I thought I’d redirect my attention a bit. I reasoned that if my brain wanted to fight engaging with work (because it’s hard), then I could use that time to read. I set the timer and once I finish the sprint, I would start on some task for the day.

Surprisingly, I’m having some success with the process. It’s not perfect, but on the days I start with reading, I’m more likely to resist temptation and tackle items on my to do list.

Coincidentally I’m reading the book Switch by Chip and Dan Heath. One of the chapters discusses the concept of shrinking the change, which is just a fancy way of expressing the idea that we should break big scary tasks into smaller, more manageable bites. Committing to something that is long and ill-defined is hard for my lazy brain to comply with, but it will comply with an easy edict, like “read for the next 25-minutes,” or “spend the next 25-minutes downloading course information files to be processed.”

These tips and hacks are not new – everyone has some flavour of it as part of their productivity system. But like losing weight, it’s not a knowledge problem. Learning and reading about how to lose weight won’t make you shed the fat, nor will it help you amp up productivity.

The challenge for me is tricking myself into not being lazy. If the only way I can do that is making an Odysseus pact, or treating myself like a child, setting a timer, and promising to do a little bit before I get a reward, then so be it.

Stay Awesome,

Ryan

Gifting Books

I’ve longed for the day when I would be in a position in my life to gift people books. I don’t mean gifting people books for Christmas or their birthday, or even as a congratulatory token for their accomplishments. Instead, I mean an unprompted, unsolicited book to people I think would value the read. Where I can give a book because of how much I enjoyed the experience, and by giving it to others I hope to share that feeling.

I’ve finally found such a book. Last week, I finished Waubgeshig Rice’s novel, Moon of the Crusted Snow, a dystopian novel about an Indigenous community in Northern Ontario that gets cut-off from the rest of the Province. It’s dark, but also life-affirming; it felt like the perfect pandemic read, even though it was published two years ago.

Despite its themes and content, it was a wonderful book to read. As I noted in my Instagram post, the characters feel real and the narrative helped me feel as though I was walking among the community while the story unfolds. A commenter on the book noted that the story is very accessible for folks who are unfamiliar with reservation life of Indigenous peoples in Canada. Yet, the book doesn’t talk down to the reader – it’s infused with cultural references, history, and language that makes you work to understand it in places.

I have already gifted this book in audiobook format to one friend, and I have ordered two more copies for other friends. I am also excited to give this book as gifts because I feel it’s important to support Indigenous and other minority voices, and help amplify them so that we can enjoy more great art from these creators.

Stay Awesome,

Ryan