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Here Are 5 Things The Smartest 20-Somethings Do

Do Cool Sh*t

That was the name of a book on a bookshelf in Barnes & Noble.

‘What kind of a book has a curseword in the title?’ I thought.

I loved it, so I immediately picked it up, sat in my chair, sipped my Starbucks Frappuccino, and began devouring it.

Three hours later I emerged from that seat with the book finished, my life changed, and a drastic need to go pee.

Filled with the desire to “do cool sh*t,” I applied to the Disney College Program when I got home. Four weeks later I got accepted as an intern, and I spent 8 months working in Disney World that very year.

Reading one book changed the entire trajectory of my life. If I never read that book, I’d have never applied to the Disney College Program. And If I never worked at Disney, I’d have never fallen in love with writing, the Philippines, traveling, or doing sh*t that scares me.

All of what I am today is owed to reading that single book. When I look back on the smartest things I did in my 20’s, reading is at the top of that list. What are some of the others? Well, stay tuned for five of my favorites..

1. Read A Lot (30+ Books Per Year)

Before I read Do Cool Sht,* I wasn’t much of a reader. I started going to Barnes & Noble in college because I was so freaking lonely there. I was depressed. I didn’t like going to school in the grey of Pennsylvania and I wanted sunlight, warmth, and fun.

I went to the bookstore to get off campus and get out of the “bubble” that is a Christian school. I wanted to feel like a normal person for once.

I remember reading The 4-Hour Workweek shortly after devouring Do Cool Sht, which was another life-changing book that made me want to work for myself online*.

It all started with books.

I have never met a stupid reader.

There are books that can help you with pretty much every problem you have. Need to cook better? There’s a book for that. Need to be a better partner? There’s a book for that. Want to be better at having conversations? There’s a book for that, too.

The smartest 20-somethings read a lot, and you should, too.

I recommend The Alchemist, The 4-Hour Workweek, Do Cool Sh*t, and The Art of Learning.

2. Write Online Or In A Journal

I’m a huge fan of journaling. I believe journaling ultimately leads to ridiculous levels of self-awareness, and that this new self-awareness can make you less angry, more patient, and more sure of what you want in life.

I started journaling when I interned at Disney World. My sister sent me a package of journals and told me I’d want to remember this time of my life. She was right. By the end of my 8 month internship, I filled up an entire 100-page journal and had an understanding of myself at 21 years old that I never felt before.

I think the smartest 20-somethings find ways to write about what they’re feeling. If they don’t write, then they find ways to reflect on their recent decisions in some form and use that to become more self-aware.

Writing online can be a great option, too. No matter if you want a job or if you just want to be a writer, you can share your insights on LinkedIn to potential employers or write under a pen name on Medium.

3. Travel

Two years of living in the Philippines has changed my perspective dramatically. The way I look at politics, social issues, money, family, relationships, and so much more has shifted like a fault line.

Me in the Philippines

Most people travel for 2–3 weeks out of the year, which is all they can get in vacation time. That’s not enough time to sink into a culture, though.

You need 6–8 weeks to properly hit the reset button.

If you can figure out a way to travel for long periods of time, you’ll emerge from the journey smarter, and with a much broader perspective of the world.

4. Start A Side-Hustle

Side-Hustles give you options. In 2020 my side-hustle turned full-time business made me six figures.

Unfortunately for many people last year, jobs were lost and incomes were slashed. I don’t want that to happen to you or to anybody you know. I want you to be in control of how you make money.

There’s tons of ways to start a side-hustle this year, like:

  • Open a print-on-demand store
  • Become an audio transcriptionist
  • Get into freelance writing
  • Become a bookkeeper
  • Produce Audiobooks
  • Sell an online course
  • Drive for Uber
  • Start a Youtube channel
  • Start a blog

The possibilities are endless here. It’s up to you to learn how to make money doing these things.

If you can control how you make money, and even how much you can make, that’s a superpower. The smartest 20-somethings know this.

5. Cold Email

In 2018, I decided I was going to organize a virtual event called the Grow Your Blog Summit.

On my quest to put on a badass event, I started cold-emailing hundreds of influencers and bloggers to come share how they made so much money writing online.

One-by-one, I got some pretty big names to come on. I interviewed Chris Brogan (330,000 Twitter Followers), Michelle Schroeder-Gardner (Millionaire Blogger), Murray Newlands (1.6 Million Twitter Followers), and even Tim Denning (100,000+ Medium Followers).

I got some of the biggest names on the internet to come on and talk about their success in the blogging world — 30 of them to be exact — and ever since then, I’ve actually kept a lot of these relationships alive.

Many of these folks became my mentor, and I’ve been able to make significant strides in my business just by being able to ask them questions and catch up with their current strategies.

Cold emailing is a hell of a way to make strides in your business and personal life. You honestly never know who could answer you back. It was a huge surprise to get an email back from Chris Brogan himself. I didn’t have much to offer him, but you know why he came on? Because I was young and he respected my hustle. We had a great conversation.

Like my friend Brian Pennie likes to say.. lean into every moment expecting miracles.

Cold emailing could be the single greatest tool for development in your 20’s if used correctly.

What Now?

Here’s the takeaways.

  • Read 30+ books per year. I’ve never met an avid reader who’s also dumb.
  • Write often, or at least reflect on personal progress weekly in a journal.
  • Travel to get drastically new perspectives of the world.
  • Start a side-hustle to be in control of how you make money.
  • Cold email a couple people per week. They could be like fireworks for you professionally and personally.

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