To build an unconventional life, abandon conventional thinking

Table of Contents

• Focus of the Week: The Thayer Method

• Mindset of the Week: Rules Worth Breaking

• Life Skills: One Cold Email Away

• Career Advice: Create, Don't Apply

• This is Cool: Open Sesame

FOCUS OF THE WEEK
The Thayer Method

Here's an intentional way to bring AI literacy into your classroom.

West Point Military Academy has been using the "Thayer Method" since the 1820s – an approach where cadets solve problems independently, then present their solutions on chalkboards to their peers.

Colonel Thayer had effectively "flipped" the classroom two centuries before it became a buzzword. It was designed way back when the chalkboard was the new technology in the classroom.

Now, a West Point professor has brilliantly adapted this for the AI era with "Brief the Bot." Students tackle problems using AI, submit their interactions for review, and then present not just the solution, but their reasoning and AI approach to the class.

What makes this so effective is how it develops three critical skills simultaneously:

• Domain expertise (understanding the subject matter deeply)

• AI literacy (using AI tools effectively and responsibly)

• Communication skills (explaining complex concepts clearly)

Instead of banning AI or treating it as a threat, this approach integrates it transparently while still ensuring students truly understand the material.

Sometimes the best innovations come from thoughtfully adapting what already works.

Adaptability isn’t just the most in demand skill for students. It applies to educators too.

MINDSET OF THE WEEK
Rules Worth Breaking

Most of us follow a script we never chose: get a degree, climb the corporate ladder, earn more to buy more, then repeat until retirement. But what if we've been approaching work and life completely backwards?

Tim Duggan, author of "Work Backwards," proposes an alternative:

1. Envision the lifestyle you truly want

2. Calculate what you need financially to support it

3. Design your work to fit that vision

Duggan lives this philosophy, working remotely just three days a week from Majorca while spending the rest of his time writing, traveling, and truly living.

Seven "Rules" Worth Breaking

Rule #1: The only way to get ahead is climbing the corporate ladder. Define "ahead" first. Ahead in wealth? Joy? Purpose? The corporate path isn't the only route to success. Portfolio careers can provide greater income, location freedom, and time ownership than traditional employment.

Rule #2: To be valuable you must work 9-5, Monday-Friday. This industrial-era relic has been thoroughly debunked.

Rule #3: Financial security only comes from a salary. False. With an emergency fund, sales skills, and smart cash flow management, you can create stability even with variable income.

Rule #4: Leaving a full-time job is too risky. Mostly false. Risk exists in everything new, but it can be mitigated through preparation. Diversifying income sources actually reduces risk compared to depending on a single employer. And remember—you can always return to traditional employment if needed.

Rule #5: To be taken seriously you need a singular career identity. False. The personal brand era celebrates multifaceted identities and diverse expertise. You can be known for multiple things and still build credibility.

Rule #6: Specialization is the only way to succeed. False. While specialists once thrived by serving specific needs, AI is rapidly overtaking specialized tasks. Being a generalist in 2025 isn't a weakness—it's protection against obsolescence.

Rule #7: Work first, life second. This is the fundamental fallacy. Instead of organizing our lives around work, we should design our work around the lives we truly want to live.

The path forward requires questioning everything you've been told about careers.

Accept nothing as given. Challenge conventional wisdom. Take the path of resistance. If you want a better story for your life, you'll need to write the rulebook yourself.

This post was a summarized version of Anna Stack’s To build an unconventional life, abandon conventional thinking article.

LIFE SKILLS
One Cold Email Away

When I was coaching students at TKS, one of the most valuable skills I taught them was how to send effective cold emails.

Most students were terrified at first. "You want me to email who?!"

But after walking them through it, and seeing the results that followed, many quickly became believers. The realization that they were just one message away from connecting with almost anyone was mind-blowing for them.

You don't need anyone's permission to reach out. The worst that happens? No response. But the potential upside is unlimited.

On a recent episode of My First million, Sam Parr and Shaan Puri were mentoring high school entrepreneurs and dropped some serious knowledge - including this gem about cold outreach:

"The most powerful people on earth are one cold email + 20 follow-ups away."

The truth is, most people never even try. They assume that successful people are unreachable, or that they need some special connection or introduction.

But in 2025, those barriers have largely disappeared. Everyone has an email or social media account. The real barrier is your own hesitation.

The screenshot below breaks down ten business lessons from that My First Million episode with the teens, that Anand argues are more valuable than what's taught in most MBA programs.

Here’s the specific 1 minute clip from the episode where Sam talks about cold outreach.

Watch it here 👇

💡 Action step: This week, identify someone you admire or could learn from, find their email, and reach out with a specific, thoughtful question. Remember - be brief, be clear about what you're asking, and make it easy for them to respond. Then, if you don't hear back, follow up (respectfully) a week later.

You'd be amazed how many opportunities in life start with simply being willing to ask.

CAREER ADVICE
Create, Don’t Apply

According to Handshake's 2025 Internship Index, the average internship posting now receives a staggering 109 applications.

That's nearly double last year's number, which was already overwhelming at 62. Three years ago? Just 43 applicants fighting for the same spot.

Meanwhile, internship postings have declined for three consecutive years as more students than ever are trying to squeeze through this narrowing funnel. The class of 2025 is 20% more likely to seek internships than the class of 2023 was at graduation.

When applications are competitive, doing the same thing as everyone else, is going to get you the same results as everyone else. You don’t want that.

Create projects, relationships, reasons to hire you. Don’t just blindly apply.

It’s not all bad news.

Despite appearances, internships aren't vanishing. Randy Tarnowski, Handshake's director of research, believes employers are "actually doubling down in ways on their early talent programs." The current situation appears to be a correction following the post-pandemic hiring boom of 2022.

Despite the frustration, both experts and students acknowledge internships remain crucial. "If anything, the value of an internship has really gone up," says Tarnowski, noting they're increasingly vital in the college-to-career pipeline.

The message is clear: the path to career entry has narrowed significantly. For today's students, securing internships requires more persistence, strategy, and resilience than ever before.

I recently caught up with one of my former TKS students, and all around wonderful human beings, Rachel.

She’s on a gap year right now, and just finished a few months working at a company helping to create and deliver renewable energy in Uganda.

She created that opportunity through cold outreach, relationships, and by being curious about what challenges in the world she wanted to solve.

I asked her what skill she thinks every high school student should develop before graduating. Here’s what she said 😍 

THIS IS COOL
Open Sesame

Some of you reading this are too young to have experienced this, but for many of us reading this, we can remember when we first started talking to our phones.

Not just on our phones, to our phones.

"Hey Siri, what's the weather today?"

The novelty was amazing... for about a week. Then we realized how limited and robotic these interactions really were.

Fast forward to 2025, and voice interfaces are on the verge of a major evolution. We're moving beyond simple command-and-response to something that feels genuinely conversational and emotionally intelligent.

I've been playing around Sesame, which is building what they call "voice presence" – making AI voice interactions feel more human, responsive, and emotionally attuned. The difference is striking.

Unlike the flat, emotionless responses we've grown accustomed to, these new voice interfaces can express excitement, thoughtfulness, warmth, and even humour. They understand not just what you're saying, but how you're saying it.

The career implications here are fascinating. Imagine:

• Interview prep with an AI coach that can actually hear your nervousness and help you sound more confident

• Language learning companions that respond with genuine enthusiasm when you nail a difficult pronunciation

• Career counseling sessions where the AI can pick up on subtle cues about what truly excites you versus what just sounds good on paper

Voice is our most natural interface – we've been using it our entire lives. As the tech becomes more sophisticated, we'll see it integrated into more applications where the emotional component of communication really matters.

Below is some context from Sesame about what they're building, followed by a quick demo of me testing it out. The expressiveness is pretty wild compared to what we're used to from voice assistants.

If you click the link above, you’ll be able to test it for yourself without needing to log into anything.

You just need to select who you want to talk to.

I chose to speak to Maya; you can listen to ~1 min of the conversation here, where I asked her what advice she would give to young people who are navigating a changing world today.

I was impressed.