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Pablo Picasso and Ben Franklin did it too

In my last email (learning like Mr. Beast), I wrote about how Jimmy Donaldson went from being a socially awkward teenager with “terrible acne” whose YouTube videos made less than $1 / day to earning an estimated $54 million dollars last year at just 23 years old.

The lessons from Jimmy’s story don’t just apply to becoming a rich and famous YouTuber…

You can use the same principles to achieve your big goals too:

1) Have a clear vision of where you want to go

Jimmy knew he wanted to become a professional YouTuber before most people even knew that was a thing.

If you don’t have a clear vision, then here are a few things you can try:

  • Start with your strengths. Lean into the things that you are interested in and already good at.
  • Then think about how your personal experience can give you a unique perspective and help you stand out from the crowd. At the intersection of these areas is your personal monopoly, as David Perell calls it.
  • Also, consider that maybe you really do know what you want, but fear is holding you back. Try this exercise from Quality Questions.

2) Learn from people who have already done it

If you asked me when I was a teenager or in my early 20’s, I would have said, “apprenticeships are for plumbers and blacksmiths — not for me” (see: My Biggest Weakness and What I Learned from Pablo Picasso in Barcelona). Now I realize, the more creative your work is, and the faster it’s changing due to technology, the more you need someone who can teach you, because you’re not going to learn this stuff in school or at the library.

It’s great if you have an actual mentor that you can apprentice under, but that’s not the only option. Jimmy did a permissionless apprenticeship by looking at the most popular videos on YouTube and asking, “what makes them different?”

You can do this too. Just ask yourself, who are the mentors I can model

3) Find or form a group / mastermind

Jimmy spent hours every day on Skype, learning together with a small group of aspiring YouTubers. Having a group of supportive peers helps you learn faster, solve problems, get exposure to more new ideas/opportunities, and pushes you to show up because you don’t want to let the group down.

If you study the stories of successful people throughout history, you will find that these are all timeless techniques. In 1727 Benjamin Franklin and a group of friends formed the Junto Club. They met weekly to discuss what they each had learned and how they could benefit each other and society.The Junto was a launching pad for many public projects. Out of the meetings came proposals for the creation of the first lending library, the Union Fire Company, the University of Pennsylvania, volunteer militia, Pennsylvania Hospital among other public project.


BTW – I used these three principles to design the structure of my upcoming cohort-based course on becoming a Digital Nomad.

If you decide to join, you’ll have the opportunity to set a clear vision, learn from someone who has already done it, and become part of a group learning together.

Here’s a sneak peak at the syllabus for the course:

Planning Your First Trip As a Digital Nomad

“How do I get started?”

This course is all about taking action and making a change. You’ll learn exactly what you need to know and do to become a digital nomad, including a step-by-step plan to actually implement this in your life.

Make Yourself at Home… Anywhere in the World

“Where should I go and how long should I stay?”

I’ll teach you the exact process I use to find and book the best places to live, work, and explore — from Miami Beach to Mongolia. So you can make yourself at home all over the world.

The World is Your Office

“How do I make sure I can still get work done?”

You’ll learn how to ensure that you stay connected all over the world, maintain (or even increase) your productivity, and how to balance getting your work done and enjoying your travels.

Get Ready for Takeoff!

“But what about my…?”

We’ll cover the logistics of long-term travel from banking and credit cards, to postal mail, insurance, drivers licenses, and your stuff (how much / what to bring, and what you should do with the rest).

…and much more! Including:

  • How digital nomads deal with visas and taxes in foreign countries.
  • How to streamline all the planning (flights, accommodation, etc.) down to less than an hour or two per month, so you can focus on having fun and getting work done.
  • How to make traveling the world cheaper than staying at home and how being a digital nomad can help you save thousands of dollars on flights and accommodation.
  • How to budget / know how much money you need to live as a digital nomad in different cities and countries all over the world.
  • Pre-emptive problem solving: What to watch out for (common problems and mistakes to avoid)
  • How you can become a digital nomad if you already own a home somewhere
  • What to do if you are stuck in a long-term apartment lease.
  • How to present yourself professionally when you’re working from a noisy place
  • What to do if your boss or employer won’t let you work from other countries
  • Overcoming objections / criticism: what to say to your family, friends, and people at work

Is there something else you’d love to learn and see included? Hit reply and let me know!

That’s all for this week! More soon…

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I write occasional emails to share what I’m thinking, learning, and doing. It’s all related to the idea of breaking free from the “default plan” in life.

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