(El Ateneo Grand Splendid, “the world’s most beautiful bookstore.”)

I used to be quite silly. I would yell, play different characters, and commit to jokes for far longer than necessary.

I’ve always tried to maintain my sense of humor. I don’t take myself that seriously. I love making people laugh. And of course, I want to be laughing each and every day.

But these last few years have been way less focused on fun and way more centered around creating and growing.

I built a solo business from scratch. I’m in the midst of expanding a podcast. I’ll be publishing a book soon.

As I sit at this laptop for hours each day, develop my skills, and focus intently on bringing value to others…I’m reminded of something a client said to me at the start of the year.

“I feel like I’ve lost my silliness.”

He was sharing about how being laser-focused on his own personal and career growth made him act more serious. But his truest, most fulfilled self was one who was goofy and who laughed at the woes of life.

Me too.

So I asked myself, How can I be a fun and silly person while maintaining my love for learning and growing?

Cut to: today. I’m more than halfway done with my time living here in Buenos Aires, Argentina. It will easily go down as one of the most rewarding and impactful periods in my life.

A month ago, I…

• spoke no Spanish
• knew nobody
• was feeling a bit overwhelmed and insecure

And since then I…

• had numerous conversations in Spanish
• became friends with people from the USA, Sweden, Brazil, Australia, Argentina, Venezuela, the UK, Austria, Germany, China, and Canada
• organized a large dinner with many of these friends
• met a woman
• interviewed some of my favorite creators on my podcast
• learned more about myself in one month than I did the entire previous year

All the while, I’ve been wildly productive and silly.

I’m writing the chapters of my book slowly and steadily. I’m sticking to the systems of my podcast uploading schedule as best I can. Potential clients continue to email me about coaching.

And I spent this entire weekend hopping around the city with a beautiful Brazilian woman, meeting friends for wine, and laughing until I couldn’t breathe.

So it seems I accidentally managed to answer my own question from earlier: How can I be a fun and silly person while maintaining my love for learning and growing?

Here’s how in 2 steps:

1) Secure the non-negotiables.

When I got into town, I spent the whole first week learning my neighborhood. Where will I spend my time?

I had to take care of the most important environments for my regular routine.

1. gym
2. coworking space
3. groceries
4. favorite cafes and bars
5. parks for walking

In terms of the 80/20 Principle, these would be the 20% of places I’d spent 80% of my time. So I invested time in making sure they were close, enjoyable, and cost-effective.

On the micro level, I do the same every Monday in my Weekly Review.

I’ll write an entire blog about each step of my WR. But in a nutshell, I just spend two hours organizing all of my project tasks and to-dos and scheduling them for my week. The goal is to then wake up each subsequent day and never wonder what I’m doing that day.

In other words, I define what “done” looks like every single week. By Friday, if I did everything I said I would do (my non-negotiables) I don’t get to feel bad for not working hard enough. I’m done.

And once the non-negotiables are taken care of…

2) Leave plenty of room for silliness.

If I’m keeping the promises I make to myself, if I’m defining the work and then doing it…then I get to do whatever the hell I want.

Within reason, of course.

I’m not staying up until 5am snorting coke and letting my body erode away.

But this weekend was nothing but pure joy, wine, and lacking any responsibility.

It was everything I loved about studying abroad in Germany.

(Oktoberfest in Munich, 2014.)

Look at this silly boy.

He had nothing but fun living in Europe. But he was a mess. He never knew what his non-negotiables were. How would he take care of his health? What was he striving toward? What value did he want to bring the world?

No clue.

So when he wasn’t partying and meeting women, he was alone in his dorm room feeling wildly depressed and scared.

I don’t feel that way now. Not even close.

Because I have my answer to all those questions. Which means…

I get to have plenty of weekends like the one I just had. Next weekend I’m taking a trip with my buddy to Brazil and Paraguay. The weekend after that, I, my lady friend, and another awesome couple we just met are going to Uruguay.

Then I fly back to the United States…which I’m quietly suppressing from myself.

Take care of the needs and leave plenty of room for the wants.

Today, I need to post this blog, do my Weekly Review, go to the bank, interview a guest on my podcast, and go to my Spanish lesson.

Once those boxes are checked, I can be as silly as I choose to be.

🚀 The YouTuber’s Guide to the Galaxy

I host a podcast where I interview professional content creators. We dive into their worlds and channels. Get inspired and subscribe on Spotify or Apple Podcasts. 

🎙 Upcoming guests

• Meghan Murphy: controversial writer/journalist
• Epic Chess: high-level chess coach who analyzes professional games
• Diane Callahan: professional writer/editor who teaches creators how to tell better stories in their writing

Thank you, ladies and gentlemen.

Dill

✌️😎

PS

I’m making some major changes to my website and branding in the next two months. Please never hesitate to send me any feedback. What do you want to see more of? Less of? Just reply to one of these emails.