Advice to My 19-Year-Old Self

Someone recently asked me, “What advice would you go back and give your 19-year-old self?”

The question was posed by one of my friends. She’s 19 (hence the question) and a total badass — way cooler than I was at 19. She’s already over a year into her startup career, already establishing herself as a respected professional in her network. She’s intelligent and articulate and indomitable. That’s why she asks questions like this. Because she’s smart and she knows that the best way to grow is to glean the perspective of those around you.

I loved the question.

It’s an interesting thing to reflect on. Three years ago, at 19, I was working on a vegetable farm and orchard, teaching writing courses, reading copiously, and trying to figure out this whole success-as-a-college-opt-out thing — slowly, but with increasing momentum. I’ve earned a lot of knowledge since then — and realized how many things I didn’t know I didn’t know (a perpetual life problem. You never know what you don’t know. But the beauty of time is that it lends perspective on what you didn’t know, but know now. In hindsight you can fill in the gaps).

19-year-old Hannah was hungry to grow, but didn’t quite know how, and she was still learning the ropes in the realm of generating self-directed momentum. She got some things right (clearly — I’ve made it this far); others she didn’t. Some opportunities she grasped inadvertently; others she missed altogether.

There are three things I’d tell her:

1. Read more

There’s a phenomenal quote by James Michener that I advocate for with all my heart. He said, “Read as many of the great books as you can by the age of 22.”

The early years of your life are foundational in your intellectual development. They become the framework for all of the other ideas and intellectual development you’re going to experience in the coming years and decades. You aren’t locked into your intellectual framework for life — it will constantly be changing — but the more intentional you can be about the framework, the more valuable it will be to you.

The Great Books are called “great books” for a reason.

The more of them you can intake, the better.

I read a lot of them — Descartes, Ovid, Plato, Sophocles, Homer, Aurelius, Machiavelli, to name just a few — but I wish I’d read more. I’m not convinced there’s such a thing as reading enough. The stronger your framework, the stronger your ability — both intellectually and practically. I want as much of the wisdom of those who came before me in my arsenal as possible as I go out and engage with the world. To borrow that wisdom, you have to intake it.

Read as many of the great books as you can — and read other things too. Copiously. Ravenously. Develop your taste for books, and refine it like a wine connoisseur refines their palette.

Read classics. Read philosophy. If you’re interested in business, read books on business. But make intake a habit, and a part of your lifestyle.

You know how you compulsively pick up your phone whenever you have a few minutes of down time, and your mind starts to wander?

Replace the phone with a book. Develop your reading capacity like you develop a muscle.

2. Document everything

Another quote — one of my favorites from my high school era. This one by Joan Didion. “To remember what it was to be me; that is the point.”

The writer in me was fascinated by this concept, because even in high school, looking back over my limited (but full and rich) years and the development they’d contained, I recognized the stark contrast between myself at each stage. Hannah at 15 — when the whole world was golden, lost in the romance of her first year of high school, weaving narratives out of the whole world — was different from the red-haired barefoot girl at 17 who stared her final year of high school in the face, developing a strain of pragmatism and slowly realizing that the world was much more tangible than it had felt at fifteen, but also more moldable — somewhere between plastic and iron — and that I had a much greater capacity than I’d initially realized to mold that tangible world into something of my own shaping, if I was willing to work to do so.

The experience of being me was different. And because I was a copious writer, and always wrote down everything, I had a log of this changing experience to go back and reflect on. At 17, I could “remember what it was to be me” at 15, and I could see how far I’d come.

But I didn’t document enough. I wish I’d documented more. I don’t regret much, but I regret every lapse in documentation bitterly. It’s an era of life, a train of thought, and an outlook that I’ll never get back. I’m moved on to another iteration of me, and all that’s left is to remember — but only if I document each step in the process.

Document everything. Start a blog and share with the world, so people can see your journey (because there’s little more powerful than having a body of proof of all you’ve done to point people to, when you find people you want to work with). Keep a journal, to remember for yourself.

Being young is a pivotal experience. You change a lot — faster than you think you will. Each stage in the process is an important part of your development. Do everything you can to capture that. You’ll want it for reference later.

3. Start sooner.

Just start. Really.

You have the whole world in front of you, and there’s a certain favor that’s granted to youth. When you’re young and just starting, the world looks at you differently. People are inclined to help you, because they empathize with being young and hungry once too. People are impressed with your successes, because they don’t expect them yet, and you can leverage that to your advantage.

I don’t regret not starting sooner — I was on a specific path, and I had to go through my own process before I understood what starting meant. But sometimes I wonder how much farther I could’ve come already, if I’d gotten a better head start.

It’s so tempting to wait for the right thing, or the right moment. It’s so easy to categorize things as things you’ll do “someday,” and put them off. Don’t. Start now. Better still, start yesterday.

Leverage your youth for all it’s worth. Take advantage of every bit of time you have. Milk it dry. Think — how far could you be in two years, three years, five, if you start now?

And as a final bonus —

Ask questions like the one my friend did. Surround yourself by people who want to grow too, and who have gone places you want to go, and ask them to lend their own perspective to yours. There’s so much knowledge and information in the world all around you, everywhere. Master the art of asking questions so you can tap into it.

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