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Despite thousands of years of collective human experience, there are still lessons each of us must learn on our own.
In my 2023 article Where Shall Wisdom Be Found?, I explored how learning, maturation and growth often happen through the lens of two conflicting quotes.
Mark Twain: “A man who carries a cat by the tail learns something he can learn in no other way”
Otto Von Bismarck: “Only a fool learns from his own mistakes. The wise man learns from the mistakes of others.”
The legendary psychologist Carl Rogers would have placed more value on Twain’s guidance, as he believed that the most profound and lasting form of education was self-initiated.
It’s not a novel thought, yet I’m surprised how often I’ll hear someone say “if I would have known what I know now back then”, or “if I would have started sooner…”, and it’s a fair and honest reflection. One of my mentors would say “the purpose of life is to go through it, and to learn the lessons, and ideally learn the lessons with still time to apply them and enjoy them”.
Through these conversations and my own reflection, I’ve been asking myself: how do you get to where you want to go, and save time doing it?
My intention isn’t to bypass the journey, that’s the most important part, but actualizing dreams and potential isn’t a non-factor. In my view, one of the primary reasons we are here is to learn timeless lessons. Yet today there are many factors that make us feel that we must “figure it out” alone.
Cultural stories and myths of individualism in books, film, etc.
Dissolution of social groups and family structures
Spread of idealism and perfectionism through social media, meritocratic systems, etc.
The rise of “answer platforms” like ChatGPT
(Note: I explore some of these concepts on the podcast in the episodes “Stop Trying to Be Happy” with Dr. Corey Keyes and “Status, Culture and the Modern Mind” with David Marx.)
In my 20s I got a lot of wisdom from books, and that’s valuable. However I have found that the lessons from books can sometimes fade, and it’s been experiential learning, self-initiated as Roger’s would call it, that has provided the most lasting impact.
So my exercise recently has been to create a playbook to combat these forces, celebrate the journey, and help people, particularly young people, develop a greater sense of self and to hopefully increase the possibility that they actualize their dreams, and ideally their own dreams vs. someone else’s.
I call it “The Five Year Leap”. It’s designed to help people get to where they want to go, and save five years if the process. The idea is that time is linear, but growth isn’t. By stacking the right experiences, what might have been years of trial and error can become a concentrated season of growth and self-knowledge that continue to be applied and enjoyed.
For me, I feel like my journey really started in my late 20s, and I’ve been fortunate to have many experiences first hand that initiated growth in new and profound ways. The famous Steve Jobs quote begins with the idea that “you can't connect the dots looking forward; you can only connect them looking backwards”, and while I can confidently say that my timing has been perfect, that there are lessons I could have learned sooner with a clear guide to experiential growth.
The components are as follows:
Mentorship — Relationships with older people, ideally those who have qualities or a life you admire, who can guide you through situations and circumstances across work, relationships, and life.
Service — Helping someone else, ideally from a different background, with enough consistency to build a true relationship.
Challenge — Doing something you didn’t think was possible for you—physical, creative, intellectual, or social (running a marathon is a common example).
Solo Experiences — Exploring the world on your own terms (even in your own city) to build confidence through self-reliance.
Self-Expression — A creative outlet that nourishes you, independent of money or recognition.
Relationships — Meaningful friendships and romantic partnerships that promote growth, belonging, self-acceptance, and love.
Mastery — Becoming great at a monetizable skill that you at least somewhat enjoy (potentially technical). Bonus points if you can generate income on your own, even at a small scale—it fuels agency and self-belief.
Introspection — Reflection to understand who you are and what you want. One of my beliefs is that if you don’t know what you want, you’ll only be left with comparison. Lots of introspection.
I don’t see these as steps on a narrow path, but as a playbook anyone can run in their own way. There’s plenty of white space for creativity and individuality. For people in their 20s, it can be a guide in a pivotal decade, and for anyone, it’s a framework, like The Artists Way, to return to whenever as you are stepping into the next evolution of yourself.
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