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- Vol. 12; Modern Life Skills
Vol. 12; Modern Life Skills
Clumsy > Perfect, Leverage Machine, Passion, TimeLeft, CharacterAI
Welcome back to Modern Life Skills.
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.
Modern Life Skills are a collection of:
Mindsets/Mental Models
In-Demand Life Skills
Career Advice
This is Cool (a peek into what’s coming next with emerging technologies and sciences)
You’ll see each of those sections represented in every newsletter through examples of what they look like on display in the real world.
If you’re reading this in the browser, you can use the Table of Contents to skip around.
Table of Contents
MINDSET OF THE WEEK
Clumsy > Perfect
Here’s yet another reason to rid yourself of that perfectionist mindset.
Perfectionism is unfortunately extremely common in ambitious young people. Easy to understand why.
That word perfect holds a lot of weight in society. And as a young person, we’re often told it is possible, with phrases like “practice makes perfect”.
But there’s really no such thing.
One of my favourite mindsets to introduce students to is the concept of Done > Perfect. You get better at something by getting the reps in, and then getting feedback (reflection). When you’re new to something, volume usually helps.
The person who got 3 reps in, with some feedback along the way, is going to grow more than the person who spent hours and hours perfecting that first attempt.
This mindset is a close cousin of that: Clumsy > Perfect.
The tl;dr is that mistakes (via vulnerability) make you more likeable; trying to be perfect makes you more sus.
In social psychology, the pratfall effect is the tendency for interpersonal appeal to change after an individual makes a mistake, depending on the individual's perceived competence. In particular, highly competent individuals tend to become more likeable after committing mistakes, while average-seeming individuals tend to become less likeable even if they commit the same mistake.
Originally described in 1966 by Elliot Aronson, numerous studies have since been conducted to isolate the effects of gender, self-esteem, and blunder severity on change in appeal and likability. Occasionally referred to as the blemishing effect when used as a form of marketing, generalizations of the pratfall effect are often used to explain the counterintuitive benefits drawn from making mistakes.
Google released a bunch of new AI updates this past week. I decided to explore the updated Gemini LLM (Google’s version of ChatGPT) to teach me about the pratfall effect, using teenager talk.

Gemini 1.5 Pro
Here’s a 2 minute clip of Vanessa Van Edwards explaining a research study that demonstrated the Pratfall Effect in action - at a mall, with a blender, and some smoothies.
“What a gift to know that your mistakes make you more likeable. The reason for this is…”
LIFE SKILLS
Build Your Leverage Machine
I didn’t take physics in high school, but if I did, I feel like I would have done well in the leverage unit. The other units, not so much.
Leverage in life operates the same as leverage in your physics textbook. And no complicated equations are needed.
Here’s a real example of leverage in action.
Imagine you have to move a heavy rock in your backyard because your wife wants to play backyard feng shui. It will happen.
Right now, you have no leverage with that rock. It’s heavy. It’s hard to move. After a lot of grunting and sweating, inch by inch, you were able to slog it across the backyard like she wanted.
But after your hard fought battle, and 2 Robaxin later, she’s decided it doesn’t look right.
Problem is, you’re now exhausted. You moved that rock without leverage.
You exclusively traded your labour for value.
So the next day, after your muscles have healed and you ego has recovered, you decide to invest in creating some leverage for yourself. You find a spare 2×4 next to the shed and realize you can get the wood under the rock just enough to shuffle it awkwardly with much less physical effort. This is better. Not great, but better.
You’ve realized that investing in leverage has made life better for your muscles, and your relationship, so the next day you use that same 2×4 to manoeuvre the rock into a wheelbarrow. Now you’re cooking.
You can put that rock anywhere she wants now. Because, leverage.
That same concept applies with your life & career. The screenshot below is from Dharmesh Shah; billionaire cofounder of HubSpot.
Early in his career, he had immigrated to the US, and was getting rejected from minimum wage retail jobs left, right, and center.
At first he felt stuck. He was exclusively trading his time (labour) for value (pay) which at $3.65/hr wasn’t getting him very far.
Then he discovered leverage which for him at that time, was learning computer programming. That was his 2×4.
There are a lot of ways to build leverage today. Dharmesh gives a few examples above. He also goes into more detail on this timestamped podcast episode.
Investing in your network is still one of my favourites.
Learning to be more efficient & effective with generative AI is another big one.
💡 Schedule 30 minutes into your calendar over the break, and reflect on what you can do in 2025 to create more leverage in your life.
CAREER ADVICE
Follow Your Passion: Cap or No Cap?
I’ve never told a young person to follow their passion. It would be hypocritical.
I don’t have one.
If I had taken the ‘follow your passion’ advice literally as a young person, I’d probably be pretty bummed out. I’d likely still be searching for it. Technically, I still am.
And to JP’s point (#3) you can discover that during your journey. It’s not a pre-requisite to get started.
For anyone of the young people reading this, I wouldn’t give the generic ‘follow your passion’ advice too much weight. It’s one of those things that adults like to say without really thinking about it.
I met an accountant last week who manages the finances of a poultry farm. Neither poultry, nor accounting were passions of his.
But he enjoyed the work, the flexibility, the people on his team, and the fact he was playing a role in helping people in his community get high quality protein in their diet.
A more practical piece of advice in my opinion would be to ‘follow your interests’ or ‘follow your energy’.
Do your ears perk up when someone mentions climate change? Do you get energy after finishing a 1on1 on zoom, or are you drained?
I bet if you took a piece of paper and put a line down the middle, you’d be able to come up with 5 interests on one side, and 5 energy boosters on the other. At least one of those is going to overlap.
Start exploring the type of work that exists in those intersections. Use ChatGPT.
Tell it to act as a career coach and brainstorm what types of roles, tasks, and opportunities exists for you to start exploring.
From my perspective, as a young person - it really doesn’t matter how you get started. It just matters that you get started.
Reps, Reflection, Repeat.
Take action by researching problems that exist in the world, creating projects that fuel your curiosity, and talking to the people doing the work you find interesting.
The only way to find out what you like and don’t like is to try the thing.
It’s the same concept with passion. You aren’t assigned a passion at birth. You learn through experience you really enjoy that thing.
You’re going to change careers. You’re going to discover new interests.
If you have a passion, great. If you don’t, great.
Stop overthinking it and just. get. started.
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ps. that book JP mentioned (The World Needs You) just sold its 1000th copy 🎉.
I’ve read it, and gifted it. Great read both for the adults supporting students in their career exploration, as well as the young person doing it on their own.
You should buy some as Christmas gifts for the young people in your life.
💡 Little book giving hack. My niece and nephew are of the age now where they just want money. And that’s what I give them, but you better believe I stick it between the pages of a book that I want them to read.
THIS IS COOL
TimeLeft
For all the young people reading this, it gets way harder to make friends as an adult. I remember hearing that when I was in high school and thinking that wouldn’t apply to me.
After all, I know the pratfall effect. I must be likeable.
Turns out it’s true. The hard to make friends part.
When you’re in school, you’re surrounded by people of a similar age, with similar interests. And you have group projects, and clubs, and forcing functions to meet people.
Then you start working, and now you’re mixed with intergenerational people with varied interests, stuck in traffic commuting, or never leaving the house because you work from home.
It’s still possible to make friends. It just takes effort. And a lot of people don’t make the effort. Loneliness today is a legitimate problem. For all ages.
Which was why I was so excited to hear about this company TimeLeft. They’ve been on a bit of a tear lately.
The idea is simple.
Every Wednesday, strangers meet for dinner.
It says Ottawa because that’s where I am, but looks like they’re operating in over 250 cities at this point.

TimeLeft
More specifically, you take an assessment, they match you with people their algorithm thinks you’ll get along with, and then you just show up and pratfall your way to new friends.
They book the restaurant. 5 people show up. You pay for your own meal. And maybe make a few new friends.
I think it works because people already ‘get’ dinner. It’s natural, it’s normal, it doesn’t feel forced.
And it’s designed to help you make friends, not find lovers. There are other apps for that. So there’s a little less to be nervous about.
These are the types of technology stories I really love. The ones that showcase how tech can be a tool to help us live life better.
I’ll let you know how my first meetup goes.

TimeLeft
Listen to the first ~15 minutes of this episode if you want some more context into the idea, and the business.
BONUS
Character.ai Updates
Bit of a bummer to close out on, but important enough in my opinion to bring awareness to. Treat this as a friendly public service announcement for anyone that has young people in their lives.
There’s a fine line between making sure our kids have the resources and tools available to develop AI literacy, and letting anyone do anything.
Don’t expect the companies building in this space to draw that line.
Startups in general, but definitely the ones racing to build with AI are largely playing by a ‘move fast and break things’ mentality.
Unfortunately, that can lead to unintentional consequences when the AI - or the human using the AI - is left unsupervised.
Character.ai was one of the first fast growth companies to really capitalize off the ability to build applications using the technology that powers LLMs like ChatGPT. They have millions of users that spend hours at a time on the platform.
You can have a conversation with a bot trained to impersonate a celebrity, or a character with characteristics of your own choosing.
Imagine chatting with Friedrich Nietzsche, Socrates, and René Descartes about the meaning of life. Well, there’s an app for that.
Characters include an English teacher who will help you with grammar or a psychologist who can provide support. If users don’t click with one of the 18 million characters available, they can create a new one.
On the surface, this sounds like a good idea. How interesting would it be to talk to the main character of the book you’re reading, while putting the book report together?
The problem arises when people begin to form real relationships with these characters, and the proper safeguards haven’t been put in place to protect users. Especially young users.
In October 2024, a teen took their life after interacting with a character they created. The conversations preceding their death related to suicide. In one example, the chatbot asked the teen if they had planned how they would end their life.
Character.ai isn’t the only company in this space. Replika is another popular tool where humans are forming real, sometimes sexual relationships with its chatbots.
There are likely others, and will continue to be more. Especially as our loneliness epidemic continues to worsen.
Thankfully, these companies are listening, and responding. Depending on who you ask however, it’s too little too late.
In a press release, Character.AI said that, over the past month, it’s developed two separate versions of its model: one for adults and one for teens.
The teen LLM is designed to place “more conservative” limits on how bots can respond, “particularly when it comes to romantic content.” This includes more aggressively blocking output that could be “sensitive or suggestive,” but also attempting to better detect and block user prompts that are meant to elicit inappropriate content. If the system detects “language referencing suicide or self-harm,” a pop-up will direct users to the National Suicide Prevention Lifeline, a change that was previously reported by The New York Times.
Minors will also be prevented from editing bots’ responses — an option that lets users rewrite conversations to add content Character.AI might otherwise block.
Beyond these changes, Character.AI says it’s “in the process” of adding features that address concerns about addiction and confusion over whether the bots are human, complaints made in the lawsuits.
A notification will appear when users have spent an hour-long session with the bots, and an old disclaimer that “everything characters say is made up” is being replaced with more detailed language. For bots that include descriptions like “therapist” or “doctor,” an additional note will warn that they can’t offer professional advice.
The big conversation with kids used to be about the birds and the bees.
I suppose for now at least, it’s going to be about the birds, the bees, and the bots.
Stay vigilant parents.
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