Category: Education

It Can Be Fine to Fail

We are involved with an initiative at work that is running dangerously close to missing its deadline. It’s a national initiative that aims to take a stance on an equity issue, and the marketing behind the initiative put the deadline for a time once long in the future that is now rapidly approaching. Folks in industry have individually worked to support the initiative’s aims, but it’s a big, hairy, unwieldy problem that will take everyone to solve.

The specifics of this initiative isn’t important for the purposes of this blog post. What is important is that there is a ticking clock that is creating a sense of urgency to act. To be completely honest, if we fail to reach our target, it won’t be the end of the world; it’s not an outcome that has immediate returns, but instead is about shifting culture and making things better for people in the long term. However, failure to reach the target will come with a certain amount of embarrassment and potential loss of good will.

I had a conversation with a colleague to discuss the initiative and the proposed action plan that’s up for consideration. A lot of work has gone into the current iteration, but some folks feel it is missing the mark in ways that can’t be ignored. The plan is being pushed forward so that work can begin and the worry is by not taking time to appropriately address the issues with the plan, we run the risk of either achieving nothing meaningful or we will cause real harm. By treating the problem as a pipeline issue, you focus your efforts too narrowly, where an “ecosystem” approach of seeing the problem as a multi-faceted set of interconnected issues that require careful consideration will require a lot more work.

It would be useful for us to understand what the cost of failure will be. The consideration must be that it’s better to fail to meet the deadline (and have a little egg on your face) than to push forward for implementation and potentially cause harm. We are dealing with people, and people will feel the deadline urgency mix with the sunk cost fallacy. If we push forward, we’ll want to ensure we do so deliberately and take responsibility for the outcomes.

Stay Awesome,

Ryan

Identifying Areas of Growth

I had my latest performance appraisal last week. I found I had a much easier time identifying areas of growth this time over last year after having gone through an accreditation visit for one of our programs. In the past, I would look at my current skillset, look at the friction points I was experiencing, and project forward a better future based on picking up some new skills or experience. This process is fine, but I realize the flaw is that the path you choose to develop in is not based on experience. It’s a guess about what might be helpful.

Contrast this to going through the accreditation process. To prepare for the performance appraisal, I reviewed the last year’s worth of information (my calendar, my one-on-one meeting notes, and notes I’ve taken about my job) and saw patterns of missed opportunities and under-performance. In these areas, I can reflect and see how if I had more skills or experience in these particular areas, I would have had a better time navigating the issues we faced.

Based on this backwards reflection (rather than guessing or projecting forward), I could more clearly articulate what I’m weak in and where I would gain the highest value in focusing on.

I think this marks for me the formal transition from the “start of career” phase to a more mature “middle career phase.” I have enough work experience and self-knowledge to draw meaningfully from, and that allows me to make smarter choices moving forward.

Stay Awesome,

Ryan

Advice from Col. Chris Hadfield’s Keynote

At my college, there is a yearly multi-day event for employees to deliver PD workshops to each others to teach skills and share experiences. The college invites thought-leaders to delivery keynote addresses to kick-off and close-out the event.

This year, the closing address was delivered by Canadian astronaut Col. Chris Hadfield. After his inspiring talk, he fielded a few questions. I was one of the lucky ones whose question was posed to him. Here is a summary of his key lessons to my question:

“How do you and fellow astronauts handle coming back to Earth? That is, the depression that comes after the high of achieving your goal/mission. “I just did that… now what?””

  • There is a misperception about going to space. It’s not just a random good thing that happens to you out of the blue – the mission has been an endeavor that is decades in the making (26-years for him from the time he decided to become an astronaut to his first mission). Even if he wasn’t chosen to go to space, he still enjoyed his job. Going to space afforded him unique experiences that honed his skills. He was gathering experiences and capabilities, then after coming back from space he could take those skills to support others and apply them in other areas of his life. He sees it as a tremendous set of gifts, tools, and new abilities to tackle the rest of his life. If you try to measure your life by one or two shiny peaks, then by definition you’ll make your life dismal. (As a side note, I read his book “An Astronaut’s Guide To Life on Earth” after his speech, and in it he goes into greater detail of what happens to astronauts after they come back. The experience doesn’t end; the job of being an astronaut has succession plans built into it that keeps astronauts useful. They spend months debriefing the mission to identify best practices that will keep future astronauts safe. They help train others, and handle mission control duties. They also help support the families of other astronauts when their loved ones are away on mission. The impression I got is that the job is designed to be a.) in service of others, and b.) purpose-driven).
  • Don’t spend a lot of time looking backwards. “If you spend a lot of your life looking backwards, you’re going to bump into your future. That’s not where things are coming from; they’re not coming from the past.”
  • The most important decision you’ll ever make is “What am I going to do next?” Some of your opportunities and skills will diminish as you age, but that doesn’t mean it can’t be vital, important, interesting, or challenging to you.
  • There are cool things happening to you everyday. Allow yourself to succeed everyday, it doesn’t have to matter to anyone else. Celebrate it. Recognize that yeah, there is crappy stuff happening, but there are cool things happening to you too, so try and choose to focus on them. There are compulsory things you have to do, but like in figure skating there are freestyle points. Try to revel in the freestyle. That leads to a life well-lived.

I’m so glad I got a chance to hear him speak and that my question was selected for response. I devoured his book and dropped many bookmarks in to return to so that I can absorb his experiences. It really drove home the problem with many self-help books that are released today – the books are written by people who are telling the stories of others. The purpose of the book (aside from sales) is to collect stories from the deeds of others in order to fit a narrative or thesis. There is an assumption that because someone else made things work that the author has the borrowed authority to provide advice to others.

I’ve learned that it’s much more instructive to turn to the primary sources and read the undiluted message from those who’ve actually been “in the arena.”

Stay Awesome,

Ryan

Forced System Growth

It’s been a busy few weeks between work and a sick kiddo at home. Sorry for missing the last two posts.

The changes I’ve recently experienced at work has inspired some thinking on this post’s topic. While I typically have a good mind for keeping track of projects (with some liberal use of a notebook), the updates to my job and the sheer scope of accrediting an engineering degree has proven to be more than my current organizational and productivity systems are capable of managing. Tasks were rapidly multiplying and open-loops weren’t being migrated for tracking; there was no translation between meeting notes and what was getting scheduled into my calendar.

I functionally hit a crossroad. One path was to keep trying to do the same thing and fall further behind, and the other was to force a systems growth to accommodate my new workload. What got me here won’t get me there, if you will. Put another way, my outputs were optimized to how I managed my workload, so if I wanted to change or improve my output, I would have to change the system. Changes in work forced the system to grow.

On one level, I want to deny this – why do I have to constantly adapt the system to new work? Can’t I find one universally applicable approach to managing my workload? Sadly, no. This is the pipedream sold by productivity wizards who claim their one system will take care of everything. The reality is that those systems are often tweaked to meet the unique cognitive needs of the person. If you want to use those prescribed systems (GTD, Building a Second Brain, etc), you will need to adapt it to how your mind processes information. And it makes sense that as you grow in your career, you will need to grow the systems that you use to keep on top of things.

Most of my systems have developed “organically.” I would implement new features on an ad hoc basis in response to specific needs. This is one of the first times that I’ve had to make large changes by first thinking through what I needed and how I wanted things to play out. As weird as it is, it reminds me of Stephen Covey and seems to combine two of his principles – begin with the end in mind, and sharpen your axe. By knowing where you want to go, and by spending a lot of front-loaded work setting things up, you have a better chance of dealing with bumps as you go.

Stay Awesome,

Ryan

Cross-Domain Knowledge

I’m a huge fan of cross-domain knowledge. Coming from an academic background in philosophy, I feel my greatest strategy for creating and building a career is leaning in hard to knowledge and skills that are learned in one domain or context, then applying it to a unique area. You get a large confidence boost when you make connections by spotting patterns and connections that map analogical cases to each other.

The first time I truly appreciated this was in my days working for the university gambling lab. We were collecting data on slot machine players by recruiting participants into our study to measure the effects properties of the machine user-interface had in gambler’s cognitive awareness. In other words, did how the graphics and sounds play on the screen help the gambler understand their relative wins and losses over time. In one study, the simulation we were using for participants to play on during the trial had been modified, but on some of the laptops the wrong version of the software was copied over, and we didn’t realize the mistake until the end of the day. Of the three laptops, two had the right software, and one did not. At the end of each session, we uploaded the user data to a secure repository and deleted the local files, which meant that once we were back in the lab, there was no way of knowing which participant file batch came from the defective software.

We thankfully caught the issue early and limited the damage, but afterwards we had an issue with figuring out which files to exclude from analysis. On the face of it, there was no way of knowing from the participant’s biometric data which simulation they used. So instead we had to dig into the debug files that were spit out by the machine to verify that the simulation ran successfully.

All the files were generated in an XML format, however I had neither experience in basic coding nor reading XML files. I had to figure out a way of showing whether the version of the software was correct. To me, the XML files were largely gibberish.

But, I was able to spot a pattern in the files that reminded me of my formal logic courses from undergrad. While I did poorly in the courses at the time, I did retain some of the strategies taught for understanding the structuring of the syntax of formal logic arguments, specifically how nested arguments worked and how assumptions were communicated. I started to see the same structure in the XML code, how sub- and sub-sub arguments were written to call different files into the program, and where those files were being drawn from.

And there it was. At the bottom of one of the debug files, was a list of the files being called on by the simulation. In the broken simulation, the file path to a certain sound that was meant to be played was empty, meaning that when the simulation was supposed to play and auditory cue, there was no file name to look for, and so the simulation moved on.

I compared this with the files we knew came from the working simulators and saw that this was the main difference, giving us the key for finding the bad data points and justifiably excluding them from the overall data set. By finding this, I saved an entire day’s worth of data files (a cost savings that includes the some-30 participant files, their remuneration, three research assistant wages, per diem costs, travel, and consumable materials on site).

I grant that computer programming is entirely built on the foundations of formal logic and mathematics, so it’s not that I was gaining a unique insight into the problem by bringing knowledge from one separate domain into another. However, this was one of the first times I encountered a problem where I lacked the traditional knowledge and skill to address it, so I came at the problem from another angle. It was a case where I gained confidence in myself to be resourceful and tap into previous learning to address new/novel problems.

As I noted above, being trained in academic philosophy has pushed me in this direction of career development. On a superficial level, relying on cross-domain knowledge is a career survival strategy because philosophy doesn’t always teach you skills that are easily applicable to the working world. I have sadly, never once, had to use my understanding of Plato’s arguments in my workplace. But on a deeper level, I think training in philosophy naturally pushes you into this kind of problem-solving. Most of my experiences in philosophy involves approaching a thought experiment or line of thinking, considering what it’s trying to tell us, then testing those arguments against counter-factuals and alternative arguments or explanations. To do this well, you have to reduce a problem down into its constitutive parts to tease out relevant intuitions, then test them out, often by porting those intuitions from one context into another to see if they still hold as both valid and sound.

It’s not all that dissimilar to the processes used by engineers or designers to gather data and accurately define the problem they are intending to design for. Whereas the engineer will apply the tools they’ve been taught fairly linearly to create a design for the problem, my strategy is to adopt cross-domain knowledge to make connections where they might previously had not been apparent. The results can often be solved quicker or more efficiently if I had the relevant domain knowledge (e.g. an understanding of coding), however when I lack the specific experience to address the problem, as a generalist thinker I have to rely on analogical thinking and a wider exposure to ideas to suss out those connections. What I lack in a direct approach, I make up for in novelty and creative/divergent thinking, which has the benefit of sometimes opening up new opportunities to explore.

Stay Awesome,

Ryan

Pandemic Career Development

I was reminded today of one thing I missed in the two years we worked from home. When carrying out your duties from home, in isolation, your interactions with your colleagues has two defining features: it’s mediated, and it’s pragmatic.

It’s mediated for the obvious reason that it’s done entirely remotely. You see your colleagues, but through a screen. You work hard to not talk over each other, because doing so makes the conversation stilted. The interactions are just more screen time you are seeking to limit, and it’s artificial in the conversational decorum that’s needed to make the medium work.

And it’s pragmatic in that your interactions are always deliberately chosen. Unless you intentionally sit on an open call, waiting for people to come in as they please, all interactions with colleagues are done by appointment and with a specific purpose in mind. The two of you “connect” virtually to discuss, then disengage to carry on with your day.

The office is different. There is something to be said for serendipitous conversations that pop up when passing each other in physical space; when you wander into someone’s office or cubicle and strike up a chat. The conversation has a tendency to float from topic to topic, because unless you booked a meeting into their calendar, your interaction doesn’t have the same constraints. Once the purpose of the chat is over (e.g. your question is answered, or the message is conveyed), you then move on to whatever adjacent topics are on your minds.

In the time I’ve worked here at the college, I’ve found a lot of opportunity for career development in the casual conversations I’ve had with people around the office. The conversations aren’t even about my career development explicitly, but instead are lessons learned through osmosis. Lessons learned when a manager is describing an issue they are dealing with, and you gleam from them insights into the skills you need to develop to meet similar challenges. Or where they share stories from earlier in their career that’s relevant to something being experienced in the present. It’s not a traditional mentorship, but if you listen closely, it can come close.

During the time I worked at home, my career development came through the projects I worked on, reflecting on skills I lacked, and seeking out ways to train into what I needed. It was always reactive and “just in time.” I didn’t realize how much I missed what happens when people are sharing a space together, and you as a colleague seeking wisdom get a chance to learn proactively with “just in case” wisdom that gets filed away for future use.

I miss the freedom of wearing shorts at home, but I’m glad to be back for the water cooler discussions.

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

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

World Limits

I’ve been thinking about the limits of my world, specifically as it relates to my ability to understand it. Much of the time, I operate as if I have access to capital-T Truth, that I have some connection with facts about the world. It’s easy to fall into this kind of thinking – when I can predict and explain events, it gives me feedback that I know things about the world in a meaningful sense.

But I also know that this confidence in my knowledge is not as strong as I assume it to be. I have to remind myself to adjudicate the claims I encounter, or to remind myself of the difference between history and the past. It’s also good to listen to others who have learned about issues from multiple vantage points (see this amazing conversation on the Tim Ferriss podcast with Noah Feldman, and his experiences with constitution building in the Middle East).

Generally speaking, all of our experience in life has presented us with a mostly successful set of interactions with the world, but those interactions are subjective and limited. Taking the long view of world events, learning new languages, and empathy provide the Archimedean point beyond ourselves to attempt to stand on some point of objectivity (if this is even possible).

As Wittgenstein says, “the limits of my language are the limits of my world.” This shouldn’t be literally taken to mean language (though I’m assuming that’s what Wittgenstein meant), but we should apply this to our understanding vis a vis experience. The limits of my world are constrained by the limits of my experience and the mental framework I use to make sense of it. If I want to seek to expand my worldview, it’s important to both prune out the dead branches of knowledge while cultivating new seeds of wisdom.

Stay Awesome,

Ryan