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- Vol. 5; Modern Life Skills
Vol. 5; Modern Life Skills
Second-Order, Do Less, Energy, Boardy.ai
🎃 Welcome back to Modern Life Skills.
🍫 One modern life skill I have been exercising this week is the discipline to not eat all the halloween candy. I’m only eating the Hershey’s cookies and cream.
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My goal with this newsletter is to share some of the most interesting and relevant content, from the best internet thinkers I know, within the domain of what I refer to as Modern Life Skills; or the skills I believe young people need to develop to be successful today, and tomorrow.
In my mind, Modern Life Skills for young people are a collection of Mindsets/Mental Models, Legitimate Life Skills, Career Advice & a peek into what’s coming next with emerging technologies and sciences, aka This is Cool.
You can use the Table of Contents below to move around the different sections, but I think you have to be reading this in the browser for that functionality to work. I’m learning as we go too.
Table of Contents
MINDSET/MENTAL MODEL OF THE WEEK
Second-Order Thinking
And then what?
It’s a surprisingly powerful mental model, and simple question you can use to make more effective decisions.
Here’s what Shane Parrish has to say about it:
Second-order thinking is a method of thinking that goes beyond the surface level, beyond the knee-jerk reactions and short-term gains. It asks us to play the long game, to anticipate the ripple effects of our actions, and to make choices that will benefit us not just today but in the months and years to come.
Second-order thinking demands we ask: And then what?
Think of a chess master contemplating her next move. She doesn’t just consider how the move will affect the next turn but how it will shape the entire game. She’s thinking many steps ahead. She’s considering her strategy as well as her opponent’s likely response.
In our daily lives, we’re often driven by first-order thinking. We make decisions based on what makes us happy now, what eases our current discomfort, or satisfies our immediate desires.
Second-order thinking asks us to consider the long-term implications of our choices to make decisions based not just on what feels good now but on what will lead to the best outcomes over time. In the end, second-order thinking is about playing the long game. It’s about choosing the ultimate goal over the immediate goal.
This default to first-order thinking makes me think of one of my favourite quotes.
“Easy choices, hard life. Hard choices, easy life” - Jerzy Gregorek
Here’s a helpful visual, which I also use as a template for introducing the concept to students.

- Second-Order Thinking (fs.blog)
And here’s a real world example of a young(er) Damian and Meredith (my wife), circa 2019 applying this mental model to a decision we were making at the time.
We were living downtown Toronto in 2019, but had decided we ready to buy our first backyard.
That meant leaving the city.
Consider the decision of buying a house outside of the city.
The immediate (first-order) effects might be having a garden, more space for your family, but also suddenly living an hour away from work.
Now look at higher-order (second and third order) consequences of each:
🥦 having a garden → able to grow your produce → having fresh herbs and vegetables at your ready
🏡 more space for family → more rooms in a house → more furniture we’ll need to buy
🚗 living an hour away from work → need to buy a car → spending two hours of each day in a car
Obviously, this is just a small subset of consequences for such a big decision, but it shows how nth-order thinking can help you see the more long-term consequences.
There were other factors considered as well, this is just a sample to show how it works.
In our case, there were no second or third or fourth order effects substantial enough to dissuade us from getting into the market. If we were in a different life position, losing 2 hours a day to the commute might have been a deterrent.
And indeed, the commute was not fun. But the second order effect of a real backyard meant we got to bring this young man into our lives. #WorthIt

- Meredith with Strider as a puppy; Nov 2019
💡 When making a decision, get in the habit of always asking yourself, “And then what?”
LIFE SKILLS
Do Less, Better
This is a concept I have struggled with for a long time. Sometimes still do.
I was absolutely that person who filled their new years goal list with far too many goals.
It felt good in the moment to write them all down, but it was never going to happen. It was more like writing a wish list to Santa, than documenting my resolutions.
As I’ve matured, I’ve realized what really feels good isn’t the idea of accomplishing the goals - it’s the habits that are formed from the effort that goes into pursuing those goals.
These days, I do less.
I’ve experienced enough to have a general sense of direction that I am focusing my concentrated effort towards.
I don’t doing less is the best advice for young people, though.
Young people need to explore, to experiment, to figure out what they like and what they don’t.
Curiosity → Experience → Reflection
You can narrow that focus as you begin to discover a destination, or a direction you’re excited to concentrate on.
For the young people reading this, do all the things. Do them with high standards, and do them with pride. But do them all.
As you mature and focus in on priorities, life should transition from a quantity game to a quality game.
This happens everywhere - from your social circles, to your professional responsibilities.
It even helped to save Apple.
Shortly after Steve Jobs returned as the CEO of Apple in 1997, he met with Jony Ive, Apple’s Senior VP of industrial design. At the time, Apple was on the verge of extinction, struggling with a bloated product line of 40 different products.
As Jobs’ toured Ive’s design studio, at one point he said, “Fuck, you’ve not been very effective, have you?” It was clear to Jobs that Ive was full of potential, but it was being held back by the company’s scattered priorities and lack of focus.
Jobs walked up to a whiteboard and drew a 2 x 2 grid. On top, he wrote “Consumer” and “Professional.” Down the side, “Portable” and “Desktop.”
By narrowing the focus, he said, they could concentrate on creating a smaller range of high-quality, innovative products.
The philosopher Marcus Aurelius pointed out that focusing on fewer things “brings a double satisfaction.” You get the satisfaction of having fewer things to do, as well as the satisfaction of doing those fewer things at a higher level.
You get “to do less, better.” In the Jobs era of “doing less, better,” Ive was very effective. He went on to design iconic products like the iMac, iPod, iPhone, iPad, Apple Watch, and AirPods. This focused approach transformed a dying company into one of the most valuable and influential in the world.
Take a second to reflect for yourself:
are you playing a quality or quantity game? Is it the right one?
what does your gut tell you is your P1 priority? Are you focused on that?
what are the second and third order effects if you went all in on that P1 priority for a year?
CAREER ADVICE
The Energy Audit
I’ve heard a few smart people in recent years (Tim Ferriss, Sahil Bloom, etc.) argue that people have less of a time management problem, and more of an energy management problem.
Think about something on your calendar that you’re looking forward to - you’ll find yourself with more energy to do that thing.
I struggle to find the energy to wake up (and stay up) on your average Tuesday. But when I know I have something exciting on the calendar that morning, I literally jump out of bed.
The key is to try and design your life so you’re spending the most time doing the things that give you the most energy, avoiding the things that drain your energy.
Easier said than done, I know. But worth attempting.
Here's a practical technique from executive coach Matt Mochary that can help you identify and eliminate energy-draining activities:
Key Steps:
Review your calendar hour-by-hour for 1-2 weeks
Mark each activity as either:
Green: Ended with more energy than you started
Red: Ended with less energy than you started
Yellow: Ended neutral
Look for patterns in the red activities

- I do not wake up at 430am. This is from Sahil Boom
When you find energy-draining activities, ask yourself three questions:
"Does this actually need to happen?" If no, eliminate it
"Do I need to be the one doing it?" If no, delegate it
"If I must do it, how could I make it more enjoyable?"
If you’re in a school, you might not have as many ‘eliminate it’ options as you would like. That’s true of a lot of roles, in a lot of industries.
But one thing most people across the board can get better is politely declining new requests. Try it. Feels great.
The next time a colleague asks you for your time, tell them you read the Modern Life Skills newsletter and it told you to do less, better.
💡 Pro Tip: Keep a document of standard "polite decline" responses for common requests. This saves time and mental energy while maintaining relationships.
I find batching tasks also helps a lot for making tasks more enjoyable. For those necessary evils, I’ll set aside a block of time on my calendar (red) and crank through them - headphones on, door closed. I’d rather rip the bandaid all at once, then drag it out over multiple days.
But ultimately, the goal is to do more energy-giving activities while eliminating or transforming the energy-draining ones.
And if all else fails, coffee.
If you want to learn about Energy Audits straight from the source 👇️
Scroll down to #2 on this Sahil Bloom article
Video: Tim Ferriss and Matt Mochary; timestamped
THIS IS COOL
Boardy.ai
If you were on LinkedIn this past week, you’ve likely already seen this. It was everywhere
It’s a new take on networking that combines voice, and AI to connect you with other people where there might be a win/win relationship to be had.
The way it works is simple: A user gives their number to Boardy.ai and receives a phone call from an AI voice assistant named, of course, Boardy.
The person chats to Boardy, telling the AI what they are working on. Boardy then checks if anyone in the Boardy network might be able to help. The network Boardy knows — which D’Souza says consists right now of a few thousand — started with D’Souza’s own network of investors, founders, and creators and has expanded since then.
It is mainly used for people who are looking to meet customers and investors and has also helped people get into accelerator programs and get matched with co-founders, he said.
“If Boardy has spoken with someone he thinks would make a good connection based on both experience, as well as whether the two of you would actually get along, he will try and facilitate a double-opt-in introduction,” D’Souza explained. If the introduction is accepted, then Boardy introduces both parties via email. “You can call Boardy back every week to work on a new introduction for you.”
It’s getting a lot of public praise.
Partly because of the novelty of it (this is the first time a lot of people are having a 1:1 conversation with AI), partly because there’s an immediate connection to the value you get from using it, but mostly - because it’s fun.
I think it’s the AI’s voice. He’s a charming Australian fellow.



I was smiling. Maybe even blushing.
When you’re talking to Boardy, he will ask you what you’re working on right now, and the type of person you want to be connected with. If it finds a match, and both people opt-in, he makes the introduction over email.
It seems like Boardy’s network is largely made up of people working in tech right now (still early days, early adopters) so if you try it - and I think you should - get creative. Maybe ask for someone who is willing to join your class for a conversation about what it’s like to start a company, or work in software, etc.
Brothers Ankur Boyed and Abhinav Boyed are part of the founding team; pictured in the article that is linked above. My guess is they’re 20 years old.
They’re also alumni of the TKS program, so of course I asked them to talk to me about it as part of the You Do What!? content series I mentioned briefly last week.

If you (or your students) have any questions you want me to ask them - let me know.
Have an idea for a life skill you think young people should be learning? Hit reply and let me know. I’ll add it to the list.
✌️ Damian