My To-Do System

Aug 11 2020


I recently read the book Make Time by Jake Knapp and John Zeratsky, and thought it was pretty good (3/5).

The book is effectively structured into 4 sections: Highlight, Laser, Energize and Reflect.

This graphic from the book gives a great overview:

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From Make Time by Jake Knapp and John Zeratsky.

The book is broken into 4 sections: Highlight, Laser, Reflect and Energize.

For me, the most important section of the book was the Highlight section, and within that, the concept of a Daily Highlight.

The concept is simple: set a Daily Highlight, the one thing that will make your day successful, and prioritize it first and foremost.

This could be a task at work, a personal project, a meeting, exercise, whatever - just make sure it is the top of your priority list.

Make Time has a nice set of tips and tricks to help selecting this Highlight, and how to focus on it, but the gist is pretty simple: nothing else matters unless your Highlight gets done.

I’ve started implementing this at work and seen a notable uptick in productivity throughout the past few weeks.

At first, my thought was there was no single thing that I could attribute as the most important part of my day, and even if there was, there was no way I could have only one. I expected to need 5 highlights, or a Top 10 list to get everything at work done, but I committed and gave it a shot.

What resulted surprised me greatly: most days really only had 1 major thing that needed to get done. If I prioritized that thing, and ruthlessly executed on that one priority, I felt accomplished looking back on my day.

This led to the next level of development: structuring my work around my Daily Highlight.

There are a few things I implemented from the book, but I would recommend buying it (or getting it from the library) if you’re interested as the set of tips and tricks work together into a cohesive system.

The one aspect I do want to focus on, however is my To-Do List.

Setting a Daily Highlight, and some recommendations in the book, pushed me to re-think my method of how I intake information. I want to become an Ask Once person, but my To-Do List system kept falling short.

So I took the advice of the authors and gave this restructuring a try.

Here’s what I came up with.

Daily Highlight

As mentioned above, I set a Daily Highlight. I like to do this first thing in the morning or just before ending my day the night before. Setting this highlight and putting it front and center on the top of my To-Do list reminds me that if I accomplish this one singularly-focused task with surgical precision, I can look back on my day feeling accomplished.

Selecting this Highlight can be challenging, as I often have multiple projects on the go, but the question I ask myself is this:

If I only accomplished one thing to move this project (or myself) forward, what would it be?

This is often easy enough to answer.

Some days it’s a specific meeting that is important. Some days it is crushing through an urgent task or solving a difficult problem. Some days it is going for a run and clearing my head. Nothing says it has to be about work, and it should be, in the words of Tim Ferriss, one thing that eliminates many other things.

It’s the lead domino.

Sometimes it makes sense for me to check my email before setting this highlight, as I can get ambushed by unexpected urgent requirements from our CM overseas or my manager, but more often than not I have an idea of what this is beforehand.

I’ve also found the Hemingway Method to be helpful here by setting that task the night before.

The second part of this is ruthlessly focusing on that task. I will often block out time in my calendar for the Daily Highlight, usually about 2 hours, and do nothing else in that time. I started off trying to set the same time daily, but this proved to be difficult.

So in summary: pick the most important task, make it a Daily Highlight, make it a priority and schedule time accordingly.

The Kitchen To-Do List

The second part of my To-Do list I took from Make Time directly. The authors mentioned how they structure their own To-Do lists, and mentioned the idea of scheduling tasks like cooking a meal: Front Burner, Back Burner, Counter, Kitchen Sink.

I worked in a kitchen throughout high school so I loved the analogy. Cooks have tremendous pressure to be on top of their to-dos in a noisy, fast-paced kitchen, so if it can work for them, it can work for you.

The concept is simple:

Front Burner is the thing that demands your most focused, immediate attention. It probably has some sense of urgency to it. It may not necessarily be the most important thing, but it’s the thing you’re dealing with now. I only let myself have 1 item on the Front Burner at a time.

Back Burner is a set of up to 3 other demands you should keep in mind, like having 3 pots bubbling away on your stove while you tend to the Front Burner. These tend to be tasks you should get done during the day or sometime tomorrow, and are less urgent, but may be just as important. I let myself have up to 3 items on the Back Burner at a time.

Counter is a space for when the Front Burner is overflowing and requires more space. Think of this as your prep station for the dish you are currently cooking. In Make Time they outline this as an area to make sub-To-Dos, for when a project is so big you have to break it into smaller pieces to make progress. You put all those small parts here. I personally don’t find this part very useful, but I like the logic behind it.

Kitchen Sink is where everything else goes. This is the dumping ground, like the dish pit in kitchen. Just throw it there until you have time to deal with it. This is where I intake any new requests on my time, and where the next phase of prioritization happens. All the Front and Back Burner items come from the Kitchen Sink (unless they are literally on-fire urgent). Anything that gets bumped from Front or Back burner gets put in the Kitchen Sink. The Kitchen Sink, thanks to the advances in digital computers, is virtually unlimited. I try not to have more than 30 or so items here, but the whole point is you can have as many as you want. Don’t let the dirty dishes pile too high, but hey, it’s a big dish pit.

This system has been revolutionary for me. Having a structured way to intake information, set a prioritization scheme for myself, and in a glance understand what to focus on, has been a breath of fresh air. My productivity has increased so much, I even have time to write this article.

Other Sections

I’ve also implemented a few other sections to expand on the Kitchen To-Do list:

Personal is where I put personal To-Dos. I thought about having a separate Kitchen To-Do list framework just for personal items, and I may expand to that as this list grows, but for now I like having work and personal items all in the same page. This section has no limit

Waiting On is where I put items that I am waiting on someone else. I often put a sub-bullet-point with the timeline and when I should poke and prod them on getting updates. For example, I am working on some packaging graphics and the next step is for our marketing team to put something together. I’m waiting on them to finalize the graphics and then I will review and send to our packaging vendors. This item “send packaging graphics to vendors - waiting on design from Marketing - Tuesday Aug 18 - poke on Friday” gets put into this category. This section has no limit.

Daily Routines is a set of small tasks (<25 minutes, most <10 min) that I try to do every day. When I do one of these routine tasks, I cross it out. In the evening I uncross all of them. If a task is something I want to drop, I remove it from the routine, and likewise if I want to add something I put it here. I was using a daily habit tracking app but found it quite cumbersome and overwhelming, so having a list of 5 or 6 things I try to do daily is quite helpful as a reminder. This section has a limit of 10 or so, but realistically shouldn’t be more than 5 core things. Any more than that and it’s time to revisit.

The Ultimate To-Do App

I have been using a Chrome extension called Mindful to implement my To-Do list.

I cannot recommend it enough. In simple terms, it makes any new window a simple text interface. It has bullet and number functionality, let’s you tab for indents, and has check-boxes, which I love. I have implemented this entire system into this interface, and any time I need to review my to-do list or add an item, I simple open a new browser window.

This has proven to be the most effective implementation I have ever used.

I’ve given Evernote a try, and I like it - especially that it syncs between my phone and computer - but found the interface cumbersome to use.

I have also used the ol’ pen and paper method, but I find it difficult to keep things structured.

This app has the perfect balance of simple and useful. No BS. No auxiliary features. No interface on-boarding. Just exactly the way you expect it to work, the first time.

I also really love that any time I open a new window to perform a task, the most important things on my to-do list are there staring me in the face. It helps pull me back when I’m procrastinating.

Putting it Together

So here’s how it gets put together.

Screenshot of new browser using Mindful Chrome extension and implementing the Kitchen To-Do List

Screenshot of new browser using Mindful Chrome extension and implementing the Kitchen To-Do List.

At the top, I added a small note to remind myself to breathe. A big checklist can induce stress, and this reminder helps me to combat that feeling.

Next I have my Highlight - in this case picking up a shipment and getting some products to people who need them.

After that I have something on the Front Burner - in this case finalizing the packaging I’m working on - which is high priority but does not take precedence over the Highlight. It’s a high priority, but not #1.

Next, my 3 Back Burner tasks, one of which has a sub-task called out. These are items I will get to when I get to them.

Lastly, the Kitchen Sink has a long list of stuff I will do when I have free time.

Screenshot of new browser using Mindful Chrome extension and implementing the next part of the Kitchen To-Do List

Screenshot of new browser using Mindful Chrome extension and implementing the next part of the Kitchen To-Do List.

Further down, I have a Waiting On section which items I’m still responsible for, but am ultimately waiting on someone or something else to take the next step. These are meant as reminders, and I have dates associated with some of them.

Screenshot of new browser using Mindful Chrome extension and implementing the final part of the To-Do List Personal and Daily Routines

Screenshot of new browser using Mindful Chrome extension and implementing the final part of the To-Do List: Personal and Daily Routines.

Lastly, I have a section for Personal items and a reminder checklist for Daily Routines.

As you can see in the Personal items section, there are some items I have checked off but not deleted, which is a reminder to myself to follow-up on these before getting rid of them. For example, I went through my clothes and made a pile I want to donate, but have not taken them to the donation bin yet. This item is checked off but not deleted.

Summary / TL;DR

  1. Set a Daily Highlight. This is the most important thing on your list, takes precedence over everything else, and will you feel like you accomplished something at the end of your day.

  2. Set up your To-Do list. I like the Kitchen To-Do list technique: Front Burner (1 item), Back Burner (3 items), Kitchen Sink (everything else), with the added section of Waiting On. Make your system work for you.

  3. Use an app or note-taking system that works. I like the Mindful Chrome extension, but Evernote, Slack, pen and paper, and writing on your forearm are all viable options. Do what works for you.

  4. Make it front and center. Put it in a place you are going to see it often and is easily within reach. When you get that sudden call from an executive or your partner, be ready to take notes.

  5. Keep it simple, stupid. The KISS rule doubly applies here: the more complicated, the harder it will be to implement, and the more stress it will cause you. Simple is best. Don’t over analyze, tweak as you go.

  6. Breathe. You’ve done the hard part: getting a system in place. The next step is to make it work for you and become the magical productivity unicorn you were meant to be. Take a deep breath and remind yourself it’s all going to be okay.

And that’s it! This is the best To-Do System I’ve come up with so far

Be an Ask Once Person

The Operations Manager at Nymi is a superhero within the company - let’s call him Joe.

Joe is the kind of person who can best be described as “on top of everything”. It seems like no matter what the task is, he’s on top of it. Joe is a model employee, has progressed steadily up the ranks to the senior leadership team, and is a linchpin.

I was reflecting this weekend about Joe, what exactly makes him so useful, and what I can learn from that.

The truth is, there are many factors that make Joe extremely useful, such as: he’s incredibly organized, he has a great working memory, he is easy to get along with, he is willing to do whatever it takes to succeed (bathroom cleaning, delivering packages, organizing calendars, etc.), he communicates extremely well, he knows when to say no and ask for help; I could go on.

But there is one critical factor about Joe I want to focus on: he’s an Ask Once Person.

Joe is the kind of person that you ask to do something once and it gets done. He’s a Message to Garcia person.

It might not get done right away, or in the timeline you were expecting - he’s a busy man after all - but it will get done. If he feels he can’t personally get it done, he’ll find someone else to help.

Sometimes, you might even forget you’ve asked him to do something, and yet somehow, it gets completed.

Joe has a reputation within the company for being reliable regardless of difficulty or complexity, and this has propelled his career from Office Manager to Operations Manager and direct report to the CEO.

Joe is an Ask Once Person, and you should be too.

This means a few things:

  1. Joe has a system for documenting tasks. When I ask Joe to update a spreadsheet or track a package or fix a leaking faucet, Joe has a system for in-taking that information and sorting it within his priority list. He may take a look at his to-do’s and decide he needs to off-board it, or tell you you need to communicate this to someone else, but the critical feature here is he doesn’t miss or forget requests. He writes everything down and prioritizes it immediately. He is also ruthless about clarifying if something is a task or not. He will stop meetings to gain clarity on a passing request in order to ensure that everything is captured. He will also often follow-up a meeting with a record of all the tasks outlined in the meeting, who is responsible, and by when. This is the gold standard of documentation.

  2. Joe has a system for prioritizing tasks. This is much more nuanced and difficult to capture in a few lines, but Joe is a master of knowing what is urgent, what is important, and what can wait. I’m still trying to learn how exactly he does this, but I’ve learned a few critical things:

    • He writes everything down and does not act on requests immediately;

    • When he does review requests, he evaluates whether he is the best person to accomplish the task;

    • He always cross-references with the most important items on his list for the day, and gets the biggest things done first;

    • He has no problem telling you no, and doesn’t feel even the smallest sense of remorse about it (he’s got too much to do!);

    • He never avoids a task just because it is difficult or uncomfortable

  3. Joe has a system for executing tasks. He is ruthlessly focused on the task at hand, and ignores all other inbound activities, with the exception of documenting future task requests. If he is blocked, he reaches out to other parties to unblock activities. He doesn’t take no for an answer, and is meticulous about follow-ups.

  4. Joe communicates effectively. Joe also has a reputation as a world-class communicator, both in person and asynchronously. When working with Joe, you know you will be notified when something is needed of you or a task is completed. There is no ambiguity and no worrying when it comes to working with Joe, because you know he’ll tell you when it’s done. Joe demonstrates that a finished task is only useful when the entire team knows about it. He sends updates, he identifies blockers, and he only provides information when absolutely necessary.

Ultimately, Joe has built a reputation of being the kind of person you go to when something absolutely needs to get done. That is a reputation he guards and cherishes closely, and lives up to on a daily basis.

So how does one become an Ask Once Person?

  1. Have an inbound task request system. A To-Do list is often insufficient, and I’ve written on how my To-Do list is structured, but ultimately having a system for dealing with requests for time and effort is fundamental to being an Ask Once person. If you’re in a meeting, or away from your computer, how do you ensure that something said in passing gets completed? Perhaps most importantly, just write everything down. Imagine you were away for a day, or missed a critical meeting because of a conflict, you would wish someone had written all these details down for you. Be that person, for everybody else. Worst case: you write down too much, and something turns out to not be important (or a fleeting thought by an executive, I get lots of those). But ultimately having an intake system, one robust and flexible, is 90% of the battle.

  2. Have a ruthless prioritization strategy. I believe that ultimately this comes down to values: do you want to be the person known for getting anything asked of them completed on time? Or do you want to be the person who says yes to everything and delivers, but not necessarily on schedule? Or do you want to be the person who says no to just about everything, but when they do say yes, treats it as life or death? This is all about prioritization. How you prioritize will determine how you survive in the throws of the fast-paced world of corporate culture. Some people use the Eisenhower Matrix to help, and I have found my Daily Highlight To-Do List strategy to be effective here, but ultimately it needs to work for you. Take things on a case-by-case basis, but have overarching principles to guide you.

  3. Have a ruthless execution strategy. All of this is just note-taking unless you get things done. How you do that will depend mostly on you and your role, but suffice to say, an Ask Once person gets thing done, no matter what.

  4. Have a communication strategy. How and when you communicate is often as important as getting the job done. On teams larger than 5 people it can be difficult to know what everyone is working on and how it all comes together into a finished project. Communication is fundamental to success here. If you get everything done ahead of schedule, but know one else knows that, it doesn’t count for much. Have a plan to get the word out, and stick to it. For some pointers on communication, check out this article about the 5 levels of employees.

In closing, here’s a simple checklist as to whether you are an Ask Once person:

  • You note down any task that is mentioned in discussion or in a meeting

  • You have a method for inputting task requests into a tracking system

  • You have a prioritization strategy to handle inputs

  • You have a set of overarching principles that drive your prioritization strategy

  • You are ruthlessly effective at getting things done

  • You have a clear set of protocols used to streamline communication within your team

  • You have a reputation for being an Ask Once person (ultimately, this is the only thing that matters)

Here’s to having more Joes in the world.

Stuck On

Aug 4 2020


I was cooking dinner with my wife on the weekend and we were both feeling pretty exhausted from a long week and a few days of running around. We finished making dinner and decided to leave the dishes until tomorrow. I offered to do them because my amazing wife did much of the cooking.

When I woke up the next day and went to do my part, I found that much of the food scraps on our plates and cutlery and the knives we used was stuck on. It had become substantially harder to clean up the mess I had made than if I did it last night.

As I stood there mindfully completing my task, the metaphor struck me.

We have both recently had some disagreements with close friends. We have been having difficulty coming to terms with these disagreements, and moving on past them like respectful adults.

Of course, these disagreements have been small and petty, much like doing the dishes.

But what I realized in trying to scrub off a dirty knife, was the longer we allow these disagreements to exist, the harder they are to resolve. They become stuck on.

So after I finished the dishes, I texted my friend and apologized for the way I had been acting. I told him that his friendship was worth much more to me than winning a petty argument, and I hoped we could meet up and resolve things properly. He immediately texted me back that he too was sorry, and we should grab coffee next week.

Whether it’s dishes, work projects, chores, or relationships, we are better off cleaning up immediately. The longer we leave dirty dishes, the harder they become to clean.

Since then, my wife and I have implemented a new rule: no evening screen time until the dishes are done.

I’m honestly not sure if we’ll be able to stick to this, but we’ll give it a shot and see how it goes. There’s always an exception if you’re truly exhausted (and want to go to sleep), but there should be no excuse for scrolling on your phone or watching Netflix while dirty dishes linger.

Especially when it comes to relationships.

Edit:

To further extend the metaphor, there’s also leaving dishes to soak.

Sometimes things get so stuck on, it’s easier to leave them to work themselves loose before trying to clean up the mess.

I think the relevance of the metaphor is when a relationship gets so damaged, it’s best to just leave it be for a period of time. Some people call this a “cooling off” period, but I like to think of it as letting the dishes soak.

When both parties have cleared their heads, and let the dirty dishes work themselves loose, it becomes much easier to clean up.

A Letter About the Pandemic

July 29, 2020


Character is what you do when no one is looking.

Dear Siblings,

What a time to be alive.

So you lost your jobs, and the world has shut down with no real end in sight.

Universities are closing and moving to online learning. Public schools are shut down. Parents are freaking out. Hospitals are in panic mode. Testing stations are overwhelmed. Government subsidies are rushing in to lend support. And you’re sitting at home unsure of what to do.

Here’s how I would think about it.

The world is going to be shut down for the foreseeable future. This could be 2 months, it could be a year; we have no idea. More importantly, you can’t control that. What you can control is what you do with that time. Ryan Holiday calls this dead time or alive time.

Are you going to look back in 6 months and be proud of the work you did? Or are you going to think back that it was a huge waste of time?

The question I’ve been pondering is this: what values will this pandemic reveal? Who am I when the world is falling apart?

Will I choose to be generous, thoughtful, productive, gentle, and kind? Or selfish, reactive, lazy, aggressive, and frustrated?

I could use this time to catch up on movies I missed - I have yet to see all the Marvel movies - and TV shows that are popular - let’s watch the Office again! - but I know that won’t satisfy me or get me closer to my goals.

Or I could use this time to improve myself.

I could set a goal of reading 1 book per week.

I could set a goal of running a half marathon by the end of the year.

I could learn how to use a new software program, like Photoshop or Blender.

I could learn to program in Python, or design a website from scratch.

I could make a commitment to practice German every day.

I could cook amazing meals for my wife every night and show my appreciation for her through my efforts.

Whatever your goal might be, I would think about this situation this way: you’ve been giving a golden ticket where the government is literally paying you to stay home and do whatever you want. The rest of the world is going to waste this time watching TV and playing video games.

It’s the like the whole world is frozen in time for 6 months, and you get a head-start.

If you were given 6 months to get ahead (or catch up) to the rest of the world, what would you do with it?

I for one wouldn’t waste it.

When you look back years from now on this time, what are you going to tell your friends? That you sat around and watched Netflix? Or that it was the inflection point that set you on a new path and changed your life?

That’s up to you.

Alive time or dead time.

Good luck,

Your brother.

Tangentially Technical

Thoughts on Skill Sets Outside of the Domain

June 25, 2020


I recently had a conversation with a VFC member has had completed Training Camp and is about to head into the job market. This is their first job out of school, and they are nervous about trying to jump into a startup in the midst of a pandemic.

This individual is truly exceptional across the board: top grades at university, internship work experience, real life experience in extra-curricular activities, and has even started their own side-project company using their skills in the midst of a difficult job market.

In any other condition, I would say this person was off to the races.

But we’re in a pandemic. Startup funding has dried up considerably. Companies are cutting back.

All that said, this isn’t why I’m worried about them. It’s that they have a tangential technical skill set, which makes decisions like this difficult.

I believe there is a spectrum of technical roles at companies, from deep and specific, to surface-level and generalized.

Trying to keep things anonymous, let’s say this person has a background in medicine. Let’s call them Jane.

In some organizations, and in some roles, that might be the exact skill set they are looking for. We are a medical device company looking to hire a medical expert in the field of cardiology, and that is what your background happens to be. It’s a match made in heaven, and you’re off to the races.

But what if you have a background in cardiology and you’re interested in working at Fitbit?

This has got me thinking about something I’ll call tangential technical skills.

To me, tangential technical skills are when you have a deep understanding and skill set of a discipline that is not directly related to your job, or a job you hope to have. Some examples might be: civil engineering and working for a construction software company; material science and working for a 3D printing company; cardiology and working for a wearable company, etc. etc.

My point here is that Jane clearly has a depth of understanding and know-how that is helpful to this organization, but not in ways they may directly appreciate.

I’m a mechanical engineer. I have built consumer hardware products. If I apply to a job at a consumer electronics hardware startup, my experience is pretty directly applicable. But what about if I apply to a robotics company that sells to large organizations on infrastructure projects? Clearly my experience is not directly related.

The challenge for any applicant, let alone Jane, is to convince the company to hire them by telling a story that links past experience, current skill sets, and a future between them and the organization.

I have told other VFC startup-hopefuls in the past: “no one cares about your experience, they care what you can do for them”. I don’t fully believe that, because ultimately I do care about your life experience and I want to work with people I enjoy getting to know and hanging out with (the Layover Test), but ultimately it is up to the applicant to express why their experience has value in this scenario.

This is where I get into deep versus surface-level technical roles.

I worked for a 3D printing startup for 3 years. Prior to joining, I had completed maybe 5 3D prints in my entire life through school and work projects. I understood the concept and how the machines worked, but I was far from an expert.

But I had nearly 2 years experience through my co-ops at 6 different organizations, and could bring a wealth of design intuition and organizational experience to the team. I had worked for 6 organizations, of various sizes, and saw how they structured processes, ran meetings, solved problems, and made a profit. That had tremendous value to a small team at the stage I was joining.

The role I was hired into was a surface-level technical role.

I’m confident anyone with some mechanical background and a lot of enthusiasm could have been a great fit for that job. Not that everyone would have been successful, but that the right person could have had a huge variety of backgrounds. I’m fortunate that person ended up being me.

But consider a much larger organization, say a company of 100+ people, hiring for a mechanical engineering role. They aren’t looking for someone to come in and be a generalist; they are looking for specific skill sets to fit within the larger machine. They are trying to find a specific puzzle piece, a right-sized gear, to help the organization grow through a very specific challenge.

This is what I would describe as a deep technical role.

If you’re a machine learning company, you probably want to hire people with deep technical knowledge of machine learning (at least for a machine learning computer scientist role).

Now take this one step further. Say you have a Ph. D. in Material Science, but you’re interested in a junior mechanical design role. I would say you have tangential technical skills to the role. Should you apply? Are you likely to get it?

This brings us to the heart of this problem.

If you believe you would be a good fit for the role, you should apply. That is a given regardless of the situation.

Does it interest you? Does it leverage your talents and skills? Can you provide value to the organization?

If you answered yes to all 3, you should apply regardless of your situation.

But are you likely to get it?

That depends a lot on you, and whether it is a deep or surface-level technical role.

But here’s how I would approach it.

If you can put yourself in the shoes of the hiring manager: ask yourself ‘what are they looking for?’ They likely have a long list of requirements they would like to check off, such as experience designing electronics, understands their way around Solidworks, can code in Python, etc. etc. They also have a second checklist of things that would be nice to have, like experience working for a startup, a go-getter attitude, design sense, etc. etc.

In many cases, your goal in the interview is to check as many boxes off the first and second list as possible.

Then there is the third list, which I would describe as open-ended culture and team fit. Do they like you? Do you like them? Are you interesting to one another? Will you fit with the team? The Layover Test. These are the intangibles that many small companies care about.

Here’s what I would recommend.

With the first list, my best advice would be to show all the things you’ve done that would check the requirements boxes.

This can often be as simple as going through the job description before hand, and writing out examples of things you’ve done that met that particular requirement, and then doing some clean-up to package those stories nicely. A good friend who is willing to listen is helpful here.

Also don’t feel like you need to meet every requirement. No one does. If you do, you’re aiming too low, and the job won’t be an area of growth for you!

You are also likely to have much more success with surface-level technical roles, not deep technical roles.

If you’re a Material Scientist applying for a Junior Mechanical Design role, describe the projects where you had to build a jig, reset a machine, tinker with something, or otherwise use your mechanical knowledge to get the result you wanted. In this phase, a hiring manager wants to see that you can do the job required and have enough experience to get up-to-speed quickly. No one wants to babysit, but they don’t expect you to be an expert on day one either.

With the second list, delve into the way you solve problems.

Developing a technical skill set — any technical skill set — is primarily about problem solving in structured, repeatable, measured ways. The techniques may differ, and obviously the specific tasks will be different, but the methodologies, and most importantly the mindset, is (relatively) consistent across disciplines.

These are also sometimes called transferable skills, or soft skills. Seth Godin has an epic rant on them here called Let’s stop calling them ‘soft skills’.

My experience throughout my degree and now into the workforce has been that the technical details — solid mechanics, fluid dynamics, stress calculations — are significantly less important than the methods of problem solving I learned along the way. Knowing how to break a big problem down into its constituent parts, how to think from first principles, how to run an experiment, how to develop new insight, how to think probabilistically, how to make an argument and gather evidence to support it which could lead to a thoughtful decision; these are the real skill sets of value to an organization.

This is ultimately what tangentially technical applicants must convince potential employers: their experience and skill sets have merit beyond just the acute, domain-specific technical details.

The third list is really up to you. This part is about 2-way fit, and that’s the topic of another blog post.

So back to Jane: what is she to do? She has a skill set that is tangential to many of the roles she is applying for.

First, I would recommend she be open-minded about the roles she considers. Startups are ultimately looking for smart, ambitious, relentlessly resourceful people to help them on their journey. If she has skills and experience that aligns with that journey, that’s a bonus, but that shouldn’t preclude her from joining along if they can be useful.

Second, I would recommend she make an air-tight case for list number 1. How does one meet the job requirements? Be specific, practiced, and thoughtful in that response. Make it easy for the hiring manager to check all the boxes on their list here. In this case, it’s not about blowing their socks off, it’s about meeting the bar.

Third, and this is the most important part, show them how the tangential technical skills bring value to the organization as a whole. If she’s up against another candidate who meets all the requirements, but doesn’t have her depth of background, the choice should be easy. Would you rather hire the analyst in operations who has a business degree, or the equally qualified person who has a Ph.D. in an unrelated field? All things equal, I’m taking the Ph.D.

Fourth, consider what it really means to learn and adapt. If she could learn an entire range of tangential technical skills, what’s stopping you from learning a new set? In her case as a new grad, she’s only been learning about this tangential career for 4 years (maybe longer with grad and post-grad degrees) but there’s nothing to say she can’t learn a new set of skills. If she thinks back to herself entering university, I’m sure she could have gone in a huge number of directions. Now that she’s older and more experience, she is no less intelligent and just as capable of learning something new. She should make the case for herself that she can grow into the role as needed. She’s willing to learn and adaptable. It may not work on all recruiters, but those two sayings are music to my ears.

So that’s what I’d do: search broadly, check the boxes, show the value of existing experience and skill sets, and learn to adapt.

Best of luck.

On Startup Ideas

Thoughts on Thoughts by Paul Graham

June 17, 2020


Paul Graham has written and talked about how to have great startup ideas.

His profound advice is not to go looking for great startup ideas, but rather, to become the kind of person who “comes up with great ideas for startups unconsciously, in fact, so unconsciously, that you don’t even notice they are startup ideas”. Put differently, become the kind of person who attracts startup ideas to them.

Marc Andreessen has written about the 4 kinds of luck. This would be the 4th kind, the kind where you are so good at your field, or embody a particular ethos, that good things are attracted towards you.

An example I read elsewhere gives that of a world-class treasure diver. If someone stumbles upon a wreck that has treasure, and they need someone to help them get it, they call you because you’re a world-class diver and experienced in removing treasure from the ocean floor. They’ll even give you a portion of it for your efforts.

You didn’t need to get lucky and stumble across the wreck to have a part in it. You simply attracted that luck based on who you are and your experience.

I think this is the same point Paul Graham is getting at with startup ideas.

If you can become the kind of person who simply notices interesting things in the world, who has a unique viewpoint and set of skills, who is capable of turning ideas into reality, then good ideas are more likely to be attracted to you. Perhaps more specifically, you are more primed to notice good ideas when you have them.

Elizabeth Gilbert has talked about ideas being these free-form, elusive, sentient things that are looking for a host to work through. They want to exist in the world, they seek to find someone to exist through, and when they find the right person they can work through that person to work into our existence. I’m not sure I believe that - it sounds a little to hand-wavy to me - but I like the sentiment of becoming the kind of person that good ideas want to work through.

Rather than trying to come up with a killer idea for a book, become the kind of person who knows how to take a great book idea and make it a reality, either as an author or a book publisher or whatever role best fits your skill set.

Paul talks further about how great startup ideas exist on the fringes, and how to find truly ground-breaking, world-changing ideas, you need to learn to work at the edges. He makes a point that great startup ideas, at first glance, feel stupid, and “your conscious mind would reject them”. Wait, you want me to get into a stranger’s car, and they are going to take me to the airport? Sounds crazy. Now Uber is a $40B company.

Paul gives further advice here, on how to turn your mind into the kind that great startup ideas:

  1. Learn a lot about things that matter

  2. Work on problems that interest you

  3. With people you like and respect

I agree with all these points, but I think the profound insight here is to invert the problem.

Don’t try to think of great startup ideas, become the kind of person who great startup ideas want to flow through.

Don’t try to think of an idea for the next great book, become the kind of person who writes great books.

Don’t try to find a workout that will help you lose weight, become the kind of person who exercises daily.

James Clear talks about this in detail in Atomic Habits, and it has changed my thinking significantly on how to get better in a variety of areas.

Rather than trying to be excellent at something, become the kind of person who exudes excellence, whether that is at work, at home, in the gym, in the kitchen, or with friends.

James tweeted the following:

I did not agree with him at first, but I think his point is that entrepreneurship pushes you to become the kind of person who can run a bus

So the best way to have a great thing happen to you, is to become the kind of person who is worthy of that thing.

When the student is ready, the teacher appears.

On Noticing

Meditations on Seeing the World Around You

Jun 17, 2020


Seth Godin was on the Tim Ferriss Podcast, twice in fact, and has distilled years of hard-earned wisdom into easily-digestible nuggets.

Here are some of the highlights around making a blog.

"The daily blog...it's one of the top 5 career decisions I've ever made."

"I don't need anyone's permission. I don't need to go out and promote it. I don't use any analytics. I don't have comments. It's just: this is what I noticed today and I thought I'd share it with you."

"Everyone should blog, even if it's not under their own name, every single day. If you are in public, making predictions and noticing things, your life gets better, because you will find a discipline that can't help but benefit you. If you want to do it in a diary, that's fine, but the problem with diaries is because they're private you can start hiding. Are you able, every day, to say one thing that's new that you can stand behind?"

I love the idea of simply doing something, without anyone’s permission, because you want to, without pressure to please or entertain or enlighten.

It’s just here, this is something I noticed today.

I’ve made this commitment to blog every day for 30 days for at least 15 minutes. It is incredible what you can accomplish in 15 minutes.

But perhaps the more incredible thing is the effect it starts to have on your awareness of the world around you.

I’ve started noticing things. Little things. Sometimes they make it into a blog post, but often they don’t. They are little things in the world, but there is some wisdom there waiting to be had. Here are a few:

  • I noticed the basil I planted in my garden has started growing new sprouts

  • I noticed that in the evening, the sunset hits my bed at just the right angle to illuminate the whole thing, as if to say “Don’t worry, I’m preparing this for you.”

  • I noticed the new bike lanes added to the road in front of my building. They are supposedly temporary, but within 2 days, the traffic congestion has diminished and people have learned to cope with reduced lanes.

  • I noticed the shear volume of people playing outside, walking, and being present in the neighbourhood last night. It’s amazing what nice weather, 2 months of quarantine and social distancing, and a big open space to do to a community.

  • I noticed that people in the park prefer to sit under the trees around the edges rather than in the middle of the field. I’m sure some park designer has thought long and hard about this, but why not put more trees in the middle? Would that make the center of the park more desirable? People playing ultimate or soccer prefer the open space, but it is not used nearly as widely as the slightly-inclined, shaded edges around the perimeter.

  • I noticed that I have been identifying thoughts passing through my head that are “blog worthy”, as if they are pieces of sushi on a conveyor belt passing my table at an automated sushi bar in Tokyo. If I like the look of one, I grab it off the conveyor and put it on my table, saving it for posting to the blog later.

  • I noticed how easily I can be distracted throughout the day. This is something I need to work on. It’s not just about laser focus - sometimes distractions are welcome! - but rather about what I am being distracted by. I would rather be disrupted by the urge to go for a run than by a cute cat video

Perhaps all this noticing will yield something more productive in the future.

HT: Seth Godin, Tim Ferriss, CJ Chilvers

Collaboration and Disagreeableness

Thoughts on the Most Important Trait for New Hires

Nov 7, 2018


I volunteer with a charity called Venture for Canada. They do a lot of amazing work in the New Grad space, primarily by connecting startups (and high growth companies) with recent graduates looking for world-class experience. It’s a seemingly perfect marriage of hungry talent looking for meaningful, challenging work, and blooming industry looking for underrated, agile team members.

So far, the program is thriving and serving both sides of the market.

Full disclosure: I went through the VFC program and it radically altered my career path (for the better).

I’ve been doing phone interviews as part of their recruitment and filtering process leading up to Fellow Selection Day.

One of the interview questions has to do with team work, and how the applicant has managed themselves in a team environment.

According to the documentation, one of the key traits VFC is looking for is a willingness to collaborate. One of the staff mentioned that they hear from partner startups frequently that they need people who can work well within a team to solve a problem.

Collaboration, and the ability to cohesively function within the team unit, is lauded as one of the most important traits for new Fellows.

I passionately disagree.

In Malcolm Gladwell’s Revisionist History podcast, he does an episode called 12 Rules for Life, poking fun at Jordan Peterson’s book of the same title.

The premise of the episode (and the book) is that each person should have a series of rules that help govern their lives; a set of principles by which to conduct themselves.

Gladwell points out that he only consumes 5 liquids ever: water, wine, tea, and a combination of espresso and milk.

But this rule is simply semantic; it doesn’t seek to serve a greater purpose.

His only rule, but his account, is simple: pull the goalie.

He is referring to this paper, by quantitative finance gurus Clifford S. Asness and Aaron Brown. It describes a mathematical model for when a coach in hockey should pull their goalie (withdraw the goalie from defending the net and replace them with an additional player). The practice is common, and simple to understand, when time is running low in the 3rd period. You’re going to lose by 1 anyways, so losing by 2 doesn’t matter, right? You should go for the tie (add an extra player to try to score) instead of accepting defeat.

The insightful and wondrous part of this paper is not that they recommend to pull the goalie — that’s simply hockey wisdom (and rather obvious) — but when they recommend pulling the goalie:

If you’re down by 1: Pull them with 5 minutes remaining.

If you’re down by 2: 11 minutes.

That’s enough to make any hockey coach roll their eyes and walk away.

No coach in their right mind would pull the goalie with 5 minutes remaining. That’s career suicide. More recently coaches have been pulling with 2 to 3 minutes left, and that’s viewed as rather liberal, and only makes sense if you have a strong power line, great puck handlers, and momentum on your side.

But 5 Minutes!? Imagine the backlash when you lose.

But what Asness and Brown are ultimately suggesting is to do the unexpected, unconventional, and otherwise disagreeable action. They aren’t saying you should recklessly go for the win, they are saying the math supports you. It’s difficult to argue with their assumptions, and from what I can tell (as an armchair academic), they have done an excellent job building a model to not just represent the real world, but actually be useful.

That can’t be said of all models (or academics).

(Frankly, Asness and Brown aren’t academics, which is perhaps why this paper is so good.)

Ultimately Gladwell points out that being disagreeable, doing the thing that no one else believes is right, but which logic or intuition or gut feeling is telling you is right, is very difficult.

Pulling your goalie with 5 minutes left in the game is ballsy to say the least.

Until you tie it up. Or come back and win. Or make the playoffs.

The math suggests you’ll end up somewhere close to 4 points ahead over the course of the season following the 5-minute rule. That is more than enough to edge opponents with less disagreeable methods.

Most coaches would happily hire a different trainer or make the team do yoga or ban Fortnite or invest in a New Age dietary supplement to gain an extra 4 points per season.

But what about losing big sometimes? Is that worth it? What about your reputation? Are you willing to risk that for 4 points?

By pulling the goalie early — 5 minutes early — you have an even larger likelihood of getting blown out quite a few games.

The odds your opponents, who were beating you by 1, beat you by 3 or 4 or 10, is realistically high.

So as a coach, you must decide whether getting the tie is worth the morale hit (and reputation) of losing by a lot.

That’s what being disagreeable is all about.

Gladwell’s entire thesis to this episode is that to be our best selves — to live life on our own terms and make our way in the world — we should strive to be more disagreeable: to do the things we know are right but go against convention.

I agree with him.

But please don’t misconstrue what I’m saying here.

Collaboration is important. If you can’t work with your coworkers, the machine of a startup — which relies so heavily on the team at the beginning of its life — is going to grind to a halt and struggle to outpace the market. You must learn to gel, to become more than the sum of your parts.

But in my experience, you also need to be disagreeable. Perhaps far more so.

It takes guts to tell the CEO they are wrong, or stand against the entire team because you have contradicting data. It’s easy to just go with the conventional wisdom or follow the herd mentality or choose to accept the presented conclusions as fact. It’s difficult to dig deeper, have your own opinion, and contest the majority.

That’s why I want people who are disagreeable.

I want someone who doesn’t care much for the status quo, and is willing to tell the entire team they are wrong because they’ve done the work themselves.

I want the spirit of Asness and Brown in every meeting and major decision at my company.

The whole ethos of a startup begins with acknowledging that the status quo, the way things are usually done, is inefficient, incomplete, or just plain stupid.

Startups have to be disagreeable, by nature.

To have team members that simply agree with what their bosses dictate goes against this entire spirit of innovation. That isn’t to say it doesn’t happen — I know lots of companies for which “innovation” roughly translates to “the big boss’s next idea”. Innovation doesn’t have to be a team sport, but it does have the potential to come from everyone.

But every startup (and big company, frankly) wants to be more innovative. That’s how they adapt, grow, and ultimately, survive. Every CEO of every company I’ve ever interacted with will tell you they want to be more innovative. But at what cost? Are they actually willing to do something uncommon, unconventional, and with consequences, in order to be more innovative? My premise is no, they aren’t. That’s exactly why startups stand a fighting chance.

If you want to be innovative, you need to stop following and start leading. You need to be willing to go against the momentum and accept the consequences.

Being disagreeable is the prerequisite for true innovation.

By the time a startup is a functioning business, and no longer in the scrappy, ideation product-market-fit phase, hiring for disagreeableness is probably less important.

Ultimately, building a factory where every machine questions their role, the vision of the company, and why it is doing what it is doing, isn’t going to be efficient or productive.

I’m not saying to be disagreeable in general.

What I am saying, and what I believe Gladwell is getting at in this episode, is to be disagreeable when you believe you are right.

To do the uncommon, unexpected, and otherwise unconventional action, despite the momentum of the commonplace, takes courage. It takes will and effort and a willingness to stand up for yourself. It also often takes evidence, data, forethought, analysis, and a lot of questioning.

In the case of the hockey coach, it comes with consequences.

It’s easy to lose 1–0 and say that the bounces just didn’t go your way. Hockey has a great deal of randomness in it, and despite your best efforts, no team is going to win every game on skill alone.

But it takes disagreeableness to lose 5–1, conceding 3 goals on an empty net in the last 2 minutes, because you decided to listen to a mathematical model from some quantitative finance guys you heard about in a podcast.

A loss is a loss, according to the standings, but in the media, a 5–1 loss you bring upon yourself is much worse than a 1–0 loss you can’t control.

That takes guts.

When I look to hire my next coworker, there are plenty of traits I’m looking for: work ethic, past experience, initiative, passion, working style, fit.

But being collaborative isn’t high on my list. I view that as a prerequisite.

I want someone who can work within our team, but my bar for that is pretty low compared to other requirements.

I care far more that when the time comes and they have a strong opinion backed by evidence and forethought, they speak up against the room. I care they stand their ground, and challenge the status quo, no matter who they are up against. I care that they are disagreeable enough to do the uncommon thing, even if there are consequences.

To me, that’s the most important character trait for an employee at a startup.

But go ahead, disagree with me. I’d love it if you did.

Interested in taking your career to the next level? A recent grad that’s not sure what your next move is? Generally a well-rounded, humble, thoughtful person?

Check out Venture for Canada here.


Dominate Humbly

A Canadian Manifesto

Everything I ever needed to know about sports I learned from my grandfather.

Jan 25, 2016


When I was 12-years-old, my grandparents attended every hockey game that season. They lived more than half an hour away, and would drive to watch us practice. They loved the run-down old hockey rinks. They loved the smell of rusting shower drains, teenage angst and team spirit. They loved the camaraderie of the parents, and the union of families around a common goal. They loved that I loved it, and I really did.

I was never the best hockey player on the team - in fact, for a long time I might have been the worst - but my grandfather would watch me play and always give me tips. He taught me to shield the puck and drive to the net. He taught me how to take a proper slap-shot. He taught me when not to take a slap shot. He taught me the power and surprise that a good wrist shot can hold. He taught me how to stick handle, and always look for the open man.

But the most important lessons he taught me had nothing to do with hockey.

Always Shake Hands

Before every game we shook hands with the other team. He taught me to always look them straight in the eye, give a firm hand shake, wish them good luck, and mean it. As much as we brought emotion into the game, it was important to remember we were all just kids, and win or lose, we were still just a group of friends playing a game we loved.

After every game I shook the coaches’ hands. He taught me that the coaches never got paid for their time, and they were as invested in the games as we were. Saying thank you, and appreciating their time was all they ever wanted to receive from us players, and the least we could do was give it to them. I think every coach I ever had was shocked the first time I did it, but it was a tradition I continue to this day.

Most importantly, he taught me to always thank the referees. This was always the hardest for me. I never held it against my opponents for wanting to win, even if it meant a cheap shot from behind, or a slew-foot in front of the net. To be honest, I usually deserved those. The things that drove me crazy were the bad calls - or non-calls - that took a game from two teams playing their hearts out, to a referee wanting to flex their muscles. But they put up with more abuse than anyone, and are just trying to do their best. The least I could do was shake their hands and thank them at the end of the game.

I always tried to remember that my grandfather was a referee for years, and imagine him in their shoes. I’m sure he blew calls sometime too - nobody’s perfect.

You Can’t Win Them All, But You Can Be Kind

Scoring a goal is hard. That’s why, when you do, it’s such a big deal.

Scoring a goal in a 1–0 game is particularly hard. More so in the third period in a playoff final.

But for every time I have had a glorious, celebratory moment where everything went right, I’ve had at least two that went wrong.

And for every game that you walk all over the other team and beat them by 5, there’s half a dozen where you get schmucked.

And most importantly, for every game you felt the refs cheated you out, remembering that they weren’t the ones who put the puck in the back of your net. Just as much as a ref can make it an uphill battle, you can dig deep and beat them. For every game you feel the ref is against you, there are two where you get the benefit of the doubt.

It’s important to remember in those moments of highlights, that you too were on the other side.

I never got flack from my grandfather for any game that we lost, as long as I gave it 110%. The games I dogged it he would ride me, but justifiably so. But one game we blew out the other team, something unruly like 10–1. I had a hat trick, and surely let the other team know. I think I drew about 4 penalties for being a bit of a smart ass as well. He lit me up on the car ride home. I’ve never heard him so cross. I had played an excellent game and did all the little things right except one: be kind.

Jeff Bezos talked about how it is easier to talented than to be kind. In moments of glory, it is even harder, but no less important. You will go much further in life by being kind than you ever will being smart or talented. Best to remember that, no matter what the score is.

Be Gritty, Be Tough, Be Smart

When I was about 10 years old my grandfather taught me what I thought was the best move on the planet.

I happened to hit a growth spurt much sooner than the rest of the kids my age, and that gave me some ungodly long legs. Thankfully, I was playing pretty high-level soccer at the time, so my coordination never really diminished. This combined for a huge edge in speed for a few years. I used to out-skate people to the puck who had a 3 stride head-start. I beat out more icings that year than anyone else in the league. I also scored a ton of breakaway goals.

I was always strong at the open-ice game, but when I got into an opponents end, particularly one-on-one, I tended to falter. I had no stick-handling ability, and generally just chose the shot. Sometimes it worked, often it didn’t.

Then my grandfather told me to just go around the guy, and cut hard to the net. I had never really thought about it, but putting your body-weight into someone when you have the puck isn’t a penalty. Running them over surely is, but leaning on someone is totally fine. I learned to shield the puck with my body and blow by people, and scored about a dozen goals that year this way. No one really knew what to do. Eventually I would just get out-muscled, but for a few golden years this worked wonderfully.

My love of being physical, though not drawing penalties, eventually shaped the way I learned to play. I would out-skate opponents on open ice, and then out-muscle them in the corner. This generally made up for my lack of stick-handling ability, and got me far more used to holding onto the puck. Eventually, teams would double-team me, and I learned to pass with intention.

Very quickly my mantra became: Be Gritty, Be Tough, Be Smart.

Being gritty meant being willing to go into the tough areas of the ice - the corner, in front of the net, playing hard defense and forcing opponents to make decisions. I learned to play just as hard in the tough areas as in the open ice.

Being tough meant not quitting when someone pulled a cheap shot. I was bigger than most, so elbows, sticks, slashes, and my fair share of punches to the head were taken. If I retaliated, I surely got the door. Being tough meant not taking people’s crap, and hitting them back where it hurt most: in the back of the net. Nothing rattles a defenseman more than cutting hard to the net and scoring after taking 10 whacks to the ankles.

And most importantly, being smart, which meant knowing when to channel your emotions, and when to calm them down. Being a smart player meant learning to use your opponents faults against them. After about a dozen whacks to the legs, you have two options: hit the guy back, or change your strategy. Changing strategy just meant going after the other defenseman. Sometimes, you just have to change it up.

Win As A Team, Lose As A Team

I had a coach during one of the best years of my short hockey career who only ever had two rules:

  1. No throwing ice - he had a kid miss out on an entire season because someone hit him in the eye and he couldn’t play.

  2. No riding a teammate for anything - doesn’t matter if he puts one in your own net in OT of the tournament finals, he’s a teammate and a friend

It is hard to take the puck all the way up the ice, beat every player, and score on your own. Some players might be able to do it, some might even be able to do it with some regularity. But it is far harder to teach 15 kids to put their egos aside and play as a team. That’s the true challenge of any coach, parent, mentor or captain. When you’re 12 and have some decent skill, you think you can do it all on your own all the time. Sometimes you might even be right, but in the dying minutes of a tight game, that attitude isn’t going to save you.

My grandfather always taught me to look first before shooting - there might be someone in a better position than you. Sometimes you need to be mindful enough to make the pass. Sometimes you need to just let it fly on your own. But the trick to being a deadly player is to keep your opponent guessing.

You have to win as a team, and lose as a team. You can’t do this on your own. When you’re down one with 1:30 remaining in the last game of a tournament, it isn’t going to be your clutch goal-scorer that gets you through. When you’re up one and grinding it out in the corner with second remaining against the toughest team in the league, it isn’t a star goalie that will save you. And when you’re in the dressing room after a 12–1 embarrassment, and you feel like you’ve been hit by a truck, it isn’t a new pair of skates or a high-priced stick that is going to get you back on track.

It’s your team. Win as one, and lose as one.

Play Both Ends of the Ice

One season I made the top 10 goal-scorers list. I did all the little things right - back-checked hard, ground it out in the corners, set screens in front of the net, made smart passes, changed lines when the team needed it - whatever it took. Then suddenly I decided I wanted to be a top scorer. My game fell off the rails, and I started playing lousy. I made simply mistakes often, and my team suffered.

Trying to be one-man-show, hot-shot goal scorer didn’t really suit me.

In fact, I rarely ever got the puck.

Constantly looking for that breakaway pass where I could pull a sweet move that everyone would be talking about in the hallways at school on Monday led to barely ever seeing it.

It was my grandfather, from his watchful perch in the corner of the rink, who noticed first. He walked around to the bench and called me over. He told me to knock off the showboating, and go get the puck if I wanted to score.

That made some sense to me.

If no one is going to give me the puck, maybe I had best go get it for myself.

I scored a hat-trick in the third period of that game.

More impressive though, I stole the puck about 8 times.

Learning to back-check hard, clog up the middle of the ice, help the defense, and force the other team to make mistakes, wound up with me controlling the game rather than chasing it.

Being a two-way player means you do not just what is best for you, but what is best for the team. Sometimes, people just need some help, and that means you’ve gotta dig deep and push out that extra 10%.

You win when everyone commits and does their job. You win consistently when everyone does their job, and supports one another.

You win when you play both ends of the ice.

Dominate Humbly

In what was the pinnacle year of my hockey career, I was the captain of the top team in the league, we had won the regular season, and it was the winter holidays. Holidays meant tournaments, and tournaments meant a trip with your friends and family. We went to London, Ontario.

We had been accepted into the invitational tournament, and played off against some of the top teams in our age group from leagues around the GTA and surrounding area.

We had a pretty stacked team, and felt we could do pretty well in the tournament, but as it goes with these things, you never really know.

But more than I have ever felt in hockey, we were a team that was hungry for it. We wanted this one, and we came prepared. New skates, lucky skate laces, special hockey tape, team bracelets for luck, and a fighting spirit to protect one another.

The first game, my first shift, I absolutely leveled a kid. Kind of accidentally (he more ran into me than me into him), but I dropped my shoulder at the last minute. He flew, I skated to the penalty box, we scored 2 goals short-handed, I had one on a breakaway when I left the box, and we won the game easily.

The second game, we switched up some of the lines to try some new combinations, and won even bigger than our previous game. We never lost focus, but instead worked at perfecting our systems knowing that the hardest teams were yet to come.

The third game we played the home team, the favourite, and one that was undoubtedly skilled. There was not a single weak player in their entire line-up, and some guys more than twice my size. I was the biggest player on our team, and was dwarfed in comparison. We scored two quick goals, and they came roaring back. With a questionable hack at the goalie after the buzzer had gone, the ref ruled it a goal and the game ended 2–2.

In the quarter- and semi-finals, we played local teams and swept them without difficulty. We had the momentum, all pistons were going, and we were playing the best hockey of the year so far.

Up to this point, one might say we dominated the tournament. We had a goal difference of about 20 points in 5 games, had 3 players at the top of the scoring leader board, and were set to take center stage in the finals. We had momentum, we had the belief, and we could almost taste it.

The final game was against the team we tied in the round-robin, and they seemed to have brought some friends. We were out-worked, out-classed, and out-played the entire game. Our goalie stood on his head, stopped more than 40 shots, and we lost 5–0. I think maybe 3 guys on the team had shots the whole game, and we never really tested their goalie. We got smoked, and not gently.

It was a rough way to end the tournament, but a stark lesson.

Sometimes, you’re going to be the champions, and you get the spoils that come with that. Sometimes, you’re going to come in last.

Sometimes you are going to get so close to victory, and have it ripped from your hands.

When we shook the other team’s hands at the end of the game, we acknowledged that they bettered us that day. They dominated. And when they shook our hands back, the told us we were a worthy adversary, and they had just hit their stride at the right moment. We earned their respect, and they ours.

They dominated, humbly.

A hard lesson to learn is how to hold your head high when you lose. A far harder lesson is to learn to be humble when you win.

Doing a huge celebration might make the highlight reel for 2 days, but accepting that sometimes you just get lucky is what turns you into a legend.

That year, after the tournament, we went back to our own league and won the championship. I scored the game-winning goal, and won the player of the game. But throughout the entire season, the highlight for me was the day I was voted captain by my teammates. More than the shiny MVP trophy, more than my name on a cup, more than a team photo or the glory that came on Monday when I gloated to all my friends at school - being part of a team that respected, fought for, and worked for one another was the best prize of all.

So when you play, in hockey, business or life, always aim to dominate. And when you do, do so humbly.

So if I’ve learned anything from my grandfather, about sports and about life, it is:

Always shake hands; with opponents, with coaches, and with referees.
Always be kind no matter the outcome.
Be gritty, be tough, and be smart.
Win as a team, lose as a team
Always play both ends of the ice.
And Dominate, Humbly.

We are Canadian, after all.

“True love is waking up at 5am on a Sunday to watch a 6am hockey practice.”

Hat tip: Aliza Rana, Papa

The Dominoes Fallacy

Jan 21, 2016


I’ve set a goal this year of running a half marathon.

Really, running a half marathon is simple. In fact, running an ultra-marathon is simple.

Two steps:

  1. Run.

  2. When you hit your goal, stop.

But running an ultra-marathon, or any significant distance for that matter, is not easy.

I believe we fundamentally misunderstand the difference between complexity and difficulty. In many facets of the world, we perceive complexity and difficulty as the same thing, but really they are not.

Look at making a beautiful steak dinner. Let’s say, for argument’s sake, you want to make a 2-Michelin-star steak dinner. You’re thinking garlic mashed potatoes, carrots, asparagus, steak, red wine reduction, and creme brulee for dessert. You need some basic ingredients - steak, good red wine, potatoes, butter, garlic, carrots, asparagus, lemon, salt, eggs, sugar, vanilla, and so on.

The point is that any one of the steps to making a 2-Michelin-Star dinner is actually quite simple:

Boil Potatoes. Nailed it.

Mash potatoes. Nailed it again. On a roll here.

Microwave garlic and butter together, add to potatoes. I’m a superstar. Call me Chef Ramsay from now on.

Each step is like this - none of them, on their own, are all that difficult. The reason we associate difficulty with completing this task is because we get overwhelmed with the complexity of the issue.

I found this everyday in my engineering degree. Solve for the total combined stress in the beam. Well, crap. That’s really hard, isn’t it?

When actually, it’s really not.

Draw a Force Body Diagram. Label the stuff you have, and the stuff you don’t. Figure out what equations apply to this scenario. Figure out if you can use one of those to find the stuff you don’t have. Plug in the stuff you have into the equations to find the stuff you don’t. Repeat as needed.

Overall, the algorithm is quite simple, but it is certainly complex.

My final exam in university was Robotic Manipulators. We had to calculate the forces required, output speeds, and fully design a control system to move a robotic arm from one position, to performing an action in another position - by hand. That’s not a simple task. But once you know the process, each step is rather trivial: multiply these things together, add these ones up, and solve for this variable.

Not a single operation in the entire class was harder than grade 11 math.

That’s beautiful, isn’t it?

But why do we think that robots are so difficult?

Because of the complexity.

I tend to think of complexity as “number of steps”.

Making a 2-Michelin-Star dinner is more complex than making PB&J or Tomato Soup, but fundamentally, none of the steps are any more challenging. It isn’t harder, just more complicated.

If you start to dissociate complexity with difficulty, you will start to realize that the vast majority of things we view as really challenging in the world are in fact quite straight-forward - there are just a lot of steps.

Here’s another way to think about it.

When I learned about Fatigue Life in Solid Mechanics (how long it takes something to fail over time and repetition) we used this thing called a “stress factor”. It was symbolized by the greek letter Psi. It was calculated by the affectionately named “k-factors”. They were labelled as follows:

Psi = ka*kb*kc*kd*ke*kf

Each k-factor represented its only area of significance - ka is temperature, kb is material, kc is the kind of notch in the system around where your stresses build up, and so on.

It’s simple to calculate each k-factor, and then you just multiply them all together. If something isn’t relevant to the calculation, it is gets a 1, so as not to change anything (ex. at room temperature).

Most people think of complexity like this:

Complexity = Multiplication of the difficulty of all of the steps

Say that 1 is the difficulty of something very simple, like putting on a pair of pants. No one bats an eyelash about how hard it is to put pants on - unless you’re a university student, but we’ll ignore that for now.

So if you’re making your bed:

Complexity = 1.00001*1.00001*1.00001*1.00001

There may only be 4 steps, and each one is easy.

But if you’re running a marathon:

Complexity = 1000

There’s only really 1 step — run — but it is far from easy.

But I fundamentally think this is the wrong way to approach this problem.

I refer to this as the “Dominoes” Fallacy - Dominoes, because there are many moving parts, but each individual step is quite simple. When you arrange an enormous array of Dominoes, setting up any individual Domino is not a hard task, but it certainly is a complex endeavor. These are fundamentally different things, however, and we cannot think of them as being the same.

I think about it like this:

Difficulty = How hard is each individual task on its own
Complexity = How many tasks are there

Under this framework, there are 4 possible scenarios, which I’ve given examples for below:

Simple and Easy: Making your bed
Simple and Hard: Running a marathon
Complex and Easy: Making a perfect steak dinner
Complex and Hard: Designing a space shuttle

Most people believe that you tackle difficult and complex problems the same way, but you really can’t treat them as the same entity at all - you must deal with them differently.

Running a marathon is a hard task, but it isn’t complex. There really isn’t any strategy or planning required - it is all about execution in the moment.

To tackle hard problems, we must dip into the part of our brain that deals with mental grit, creativity, and innovation.

Making a 2-Michelin-star dinner isn’t hard, but it is complex. There requires a great deal of strategy and planning, and execution in the moment is less important. If you can plan out your steps methodically, and continually perform them correctly, accomplishing a complex task is no sweat at all. It is really just accomplishing a long series of simple tasks.

Peter Thiel in Zero to One talks about the importance of both humans and computers, and how we are fundamentally different systems. Humans are amazing at solving hard problems - we can think abstractly, be innovative, and make connections where there were previously none. Computers are amazing at solving complex problems - they can do routine, simple steps, in remarkably high volumes, with amazing accuracy and precision.

When you face a problem in life, business, relationships or otherwise - ask yourself - is this hard, or complex?

Complex tends to lend itself to automation, where hard lends itself to ingenuity. Complex problems can be solved if they can be ordered (Computer Science problem) but hard problems can be solved if they can be untangled (Mathematics problem).

It is at the intersection of these two concepts - the hard complex problems - that the true magic happens. We call this innovation. Peter Thiel founded Palantir which specializes in large-scale data analytics based on this principle - using computers for complex challenges, and humans for hard ones. They just raised $800 million.

The next time you run into a problem, ask yourself these questions:

Is this hard, or complex?

If it is hard, what about it makes it hard? If it is complex, what about it makes it complex?

Can I find a solution to the difficulty? Can I automate the complexity?

Do I need both?

This is a good framework and baseline to start with. I’ve used this exact technique to automate a huge majority of things in my life, such as setting up systems to take vitamins, dealing with fitness and dietary goals, dealing with exam questions at school, and designing complex interacting systems in my career.

I even aced my Robotics course.

As for the ultra-marathon? Well I’m working on it.

Hat tip: Peter Thiel (Zero to One), Derek Sivers (Tim Ferriss Podcast)