How to Win at High School, College & Life: Uncommon Advice for Students, Parents, Teachers & Mentors

Written by Scott January 27, 2015

A room full of possibility

“I have never let my schooling interfere with my education.”

– Mark Twain

Important: Today I’m sharing a speech I recently gave that I’m very proud of – and the guidance in the talk and tools on this page don’t just apply to students and young people. The advice here is universal and stands to help everyone in our community. So listen up and please put it to use!

What I Wish I Would Have Known at 17 Years Old

For me, it’s a long list, and today I’d like to share it with you…

I have incredibly strong feelings about education. More specifically, about providing the right type of practical education, tools and guidance to help kids and students find direction and go on to actually do work and create lives they’re happy and proud about.

I see this as a huge responsibility for all of us – to provide needed guidance to our future leaders.

Because poor direction early on can lead to decades spent spinning our wheels and correcting course (I’m guessing I’m not the only one who can relate). But it doesn’t have to be that way.

And that’s why I’ve published today’s talk and guide: to serve as a living resource to help kids and students start living their legend from Day One. 

(It’s also why I recently made a significant donation to The Wayfinding Academy, a new type of school designed to solve many of these problems.)

The Talk – & Launch of the LYL Student Resources Page!

A few days before leaving on this year’s World Tour (I’m currently in Montenegro en route to Turkey then Tanzania for some volunteer work and to attempt Mt. Kilimanjaro), I was invited back to my high school to give a talk sharing my advice for students. I was honored and leapt at the chance to stand in front of what I believe is the most important audience and age group of all.

So I dug deep into the past decade or so and came up with a list of things I wish I would have known and done when I was in high school and college.

With the school’s permission, I recorded the talk, and am incredibly proud of how it turned out. So I decided to take this as my opportunity to create a Live Your Legend Student Resources Page – to serve as a guide for kids, students, parents, teachers, mentors and anyone who knows anyone in those roles (i.e., all of us!).

Below is an audio recording of the talk, followed by a list of key topics covered.

I’ve also created a list of related articles, videos, books, tools and resources for students to live your legend, pursue dreams, do work you love and lead a life that makes you proud.

So today I’d like to ask that you do three things:

  1. Listen to the talk, or at least the first few minutes.
  2. Share it with at least one student and one parent whom you think the message will help. Just send them a short email saying something like “Hey – you gotta see this new free resource from Live Your Legend, a site I follow closely. I think it will help a lot: How to Win at High School, College & Life: Uncommon Advice for Students, Parents, Teachers & Mentors (”
  3. If you have your own piece of advice, tool or video, please share it in the comments. The LYL community is much more powerful when we put our heads together!

Even if you don’t have time to listen to the talk today, still take a minute to send the resource to someone who’s future you care about. School is starting again and students and parents can always use the support. It might have a much bigger impact than you realize.

Now, give a listen, and for bonus points see if you can notice where I get choked up near the end as I talk about my biggest high school regret…

Live Your Legend Student Resources

How to Win at High School, College & Life: Uncommon Advice for Students, Parents, Teachers & Mentors

Step #1: Listen to the Talk

Click play below to listen to my full talk:

Or click here to download the full audio file of the talk.

Key Topics & Stories Covered in the Talk:

  • What’s on my “Inspire Me Pump Up” song mix (hint: it’s not just Taylor Swift and Broadway musicals)
  • Top of my class for detentions and Saturday schools
  • Avoiding the tragedy of a short life
  • Richard Branson’s productivity hack for starting more than 400 companies
  • Creating confidence and the 9-year-olds most thought would drown
  • Running 50 miles and the power of doing your own impossible (and being beat by people twice my age)
  • Having the right (and wrong) friends and the most important life hack I’ve ever seen
  • Distinguishing real friends and the myth of the Facebook friend
  • Finding people who inspire you and three questions to ask every interesting person
  • The origin of LYL and why I am absolutely in love with the book The Alchemist
  • Identifying role models and deconstructing the path (and assumptions) of successful people
  • My best advice for finding the perfect mentor and connecting with influential people
  • The reason for my annual business and life retreat in the mountains
  • The $100-million-dollar man who wishes he’d made less money and his three pieces of advice for students and young professionals
  • The surprising income level needed for peak happiness
  • A practical exercise for figuring out how much money is enough (and too much) to do what you care about
  • Charlie Munger’s key to happiness
  • The importance of good grades, their limitations and what matters even more
  • Dealing with and benefiting from inevitable future failures
  • Graduating top of my class and rejected from every job I applied for
  • The massive failure that launched my career and led to Live Your Legend
  • My biggest piece of educational advice: Get out of the country and study abroad!
  • My experience studying, living and working as a teacher and tour guide in Spain
  • My first entrepreneurial pursuits, experiments, screw-ups and successes
  • The biggest risk we all face in pursuing work we love and a life we’re proud of (often without knowing it)
  • Avoiding a lifetime of regret and how I make big decisions
  • Pursuing the spark – a consistent daily process for experiments, fun and adventure
  • My (somewhat odd) morning routine
  • A word of warning: what college will NOT teach you
  • An alternative approach to choosing a college major that doesn’t cause you to hate your life later on
  • The one thing much better than a great resume – and how to leap off the page
  • Time Management 101 for stressed-out students – how to decide what to focus on to get into your dream school, open the most doors and have the biggest impact
  • Social Media Warning: The under-appreciated, irreversible side-effects and the lives you might not realize you’re hurting
  • My four biggest regrets from high school and how to easily avoid them
  • A daily practice for creating your own luck and making the world a better place
  • The fastest way to get someone to believe in you

Additional Resources

These lists of resources come mainly from what we’ve written and created here on LYL, as well as a few other trusted sources. We’ll continue to add to these over time.

Articles & Tools

Figuring Out Who You Are & Taking Action:

Alternative Learning & Self-Guided Education:

Surrounding Yourself with the Right People:

Other Articles & Topics Mentioned in the Talk:

Also see Live Your Legend’s top articles for solving your 14 biggest challenges + every article we’ve written

Videos & Talks to Watch

Steve Jobs’ 2005 Stanford Commencement Speech:

My TEDx Talk on How to Find & Do Work You Love:

There are of course many more videos to see, but these are the ones mentioned during my talk and serve as a powerful foundation.

Also check out: 

Books to Read

A short, focused list by design. The list of books you could read is endless, but here’s where I’d start. 

  • The Alchemist by Paulo Coelho – Very quick, easy and fun read. I read it every time I leave the country and it’s where the idea for Live Your Legend was born. One of best-selling books of all time with more than 65 million copies sold.
  • How to Win Friends and Influence People by Dale Carnegie – If there were only one book someone could read, I think this would have to be it.
  • StrengthsFinder 2.0 Online Assessment and book – The 30-minute online assessment is where the magic is and comes free with the book. There’s also a more recent StrengthsExplorer tool for ages 10-14 and their parents. I’ve only had experience with StrenghtsFinder 2.0 and have loved it.
  • What Color Is Your Parachute? for Teens and the original What Color Is Your Parachute? book by Richard Bolles – One of the most powerful and popular career books of all time. The real magic is in the accompanying exercises and workbook.
  • How to Become a High School Superstar by Cal Newport – Powerful ideas on standing out and getting into your dream college. Concepts also apply to business and life.

Other Resources

Advanced LYL Courses: 

So, that’s the list… for now.

A list like this will never be complete, so this page is instead meant to be a living, growing resource for students and parents. We’ll continue to add to it over time. And if you have suggestions of your own, I’m all ears!

For now, I’ll close with the same piece of advice I gave at the end of my talk – something that applies to all of us…

Find someone who believes in you.

And the best way to find someone who believes in you… is to do something worth believing in.

The learning never ends,


Now, please do your part – these two things:

  1. Share this page with at least one student and one parent whom you think it will help. Just send them a short email saying something like “Hey – you gotta see this new free resource from Live Your Legend, a site I follow closely. I think it will help a lot: How to Win at High School, College & Life: Uncommon Advice for Students, Parents, Teachers & Mentors (”
  2. If you have advice of your own, tell us in the comments! What’s one piece of advice, article or video you have for today’s kids and students, or what’s something you wish you would have done differently? The LYL community is much more powerful when we put our heads (and experience) together!

Let’s all do our part, and this resource will become more comprehensive and useful as time goes on.

And remember, the tools on this page don’t just apply to students and young people. Most of the advice here is universal. Do something with it.

We’re all students of life. 🙂

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“You are the average of the five people you spend the most time with.” - Jim Rohn