The Art of Dreaming Without Going Broke

7 Lessons from 22 Years of Creative Entrepreneurship

Hello Artists,

Today’s Deep Dive Class is dedicated to younger Darius—the one with a big dream to share his passion and art with the world, all while achieving financial freedom.

In my 20s and early 30s, I often struggled to balance my BIG dreams with real-world responsibilities, like paying the bills. Part of me avoided looking closely at my relationship with money, diving headfirst into creativity, hoping my dreams alone would lead to financial success.

I secretly believed that if I gave everything to my work, the money would somehow work itself out. I devoured every Law of Attraction book I could find, convinced that if I just stayed positive, I would manifest the financial abundance I needed.

But in my twenties, this led to some harsh wake-up calls. After ignoring my financial situation for months, I found myself barely able to pay rent. I remember asking my landlord, Frank, for extensions multiple times. It was humiliating, and I constantly asked myself, How did this happen? How did I get here?

I ignored important realities, which led to some very tough situations. In those desperate moments, I started to resent my dreams and the part of me that dared to dream big. Eventually, I gave up on those dreams. Even now, it saddens me to think about it.

At 41, I’ve found a much more sustainable, productive, and joyful way to balance dreaming and making money. I’m not claiming to be a money guru—because I’m not. I am still a work in progress and have a lot to learn.

But after 22 years of creative entrepreneurship, I have picked up a lot of BIG lessons.

In today’s Deep Dive Class, I’m using Substack as a time machine to send my best lessons, strategies, and frameworks back to my younger self in his 20s and early 30s.

I’m also sharing these lessons with other dreamers looking for a more sustainable way to make their dreams a reality.

I hope this class resonates with you.

BIG Love,

D

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The Art of Dreaming Without Going Broke

Hit the play button on the audio player below to dive into this week’s Deep Dive Class. And don’t forget to check out the journal prompt below!