Starting Your Self-Directed Path

I am currently reading my fellow Berkeley alumni Blake Boles’ book Better Than College (by the way, that was not intended to be a tongue twister). In this controversial book, Boles discusses the idea of success without college. This path is all about learning about oneself through a self-directed course of study focused on experiential learning. To help people get started on this path of self-direction, Boles poses three questions.

In this article, I list those three questions, as well as my own answers to them. Whether or not, you prescribe to the non-traditional, “unschooling” path, I highly recommend you actually take the time to write out your own answers to these questions. Remember, there is no better investment than the one you make in yourself. So take the time to actually find out about yourself. Hopefully my own answers provide some inspiration. Without further ado, let’s get started.

1. If you were going to die one year from today, what would you do differently?

I would start by pulling out my bucket list. There’s currently 95 items that I still need to do. I would pick my top 12—one for each month. Then I would gather all of my money and pool it. I would supplement that by money from my parents and also from a GoFundMe campaign.

I would then look at my top 12 bucket list items and just pick a single item. I would go all out on accomplishing that one item. Just for some specificity, I would choose “visit Angkor Wat” to be my first item. I would ask any friends or family if they would like to go, purchase the plane tickets, book the hotel rooms, and spend 2 entire weeks in Angkor Wat.

Once my Angkor Wat trip is over, I’d move on to the next item. “Write a novel” sounds like a good item to pick. I’d spend about a week or so prepping for the project and then go all out for 3-4 weeks to write it. I’d then publish it just for kicks and have all my loved ones buy copies of it. That would be awesome.

And then, I’d keep going down the list. If I finish my top 12 before the year is up, I’d just do more bucket list items—there are 95, after all, that I haven’t done. With each item, I’d do my best to incorporate my friends and family into it. For example, I would take them with me on my trips. I’d go skydiving or hot-air-balloon-riding with them. The only thing better than do awesome things is doing awesome things with awesome people. I would love to spend my last year with the best people I know.

At the very end, I’d splurge my remaining funds on an epic party and invite all of my friends and family. We’d have one last hurrah before it was all over. Then I could die happy, knowing that I lived my life to the fullest

2. If you had three years to create something that would change your world, how would you begin?

My dream is to create something that would vastly benefit today’s young people and college students, in terms of helping with their education and preparing them for an increasingly uncertain world.

I would begin by researching people who are already doing this. There’s tons of men and women who are just crushing it in this space. I’d make a ranked list and just go down the list, cold emailing or calling every last one of them. I would offer to do free work for them in return for their mentoring—an apprenticeship of sorts. At the same time, I would invest money in courses, books, seminars, and things like that to further my learning. So I would be getting both practical and theoretical knowledge about how to create something of value.

As my learning and apprenticeship is going on, I would take what I learned and begin applying it to create something awesome. I would constantly tweak, pivot, and reiterate as I learn and grow. At the end, I would have an amazing product that would fulfill my dream.

3. If you were forbidden from accumulating vast material wealth, how would you live differently?

I would spend all of my money—besides what I spend on bare necessities—on two things: charity and experiences.

I would give, give, give to all of my favorite charities. Pencils of Promise. Heifer International. Kiva. Elizabeth Glaser Pediatric AIDS Foundation. I’d give so much money to all of them. And I’d donate a good amount of it anonymously. Not just to cross off a bucket list item, but also because it feels so much better to give selflessly, expecting not even recognition in return.

And then I’d spare no expenses on awesome experiences. I’d go skydiving, visit the Seven Wonders of the World, attend life-changing conferences, and chill out on the sand dunes of Egypt. I’d do it all and I’d take all of my favorite people with me. I would have the time of my life.


So there you have it. Those are my answers to three life-changing questions. Hopefully it inspires you to take the time to actually write out your own answers. Trust me, you won’t regret it.