The Art of Dreaming Without Going Broke

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.


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!


  1. Lust Dreams vs. Love Dreams —> The Chase Can Make You Broke.

  2. Identify where you fall on the Dreamer Spectrum and find your counterbalance.

  3. Divide your projects into three categories: stomach, head, and heart. Always start by feeding your stomach—without financial stability, your head and heart will starve.

  4. Remember: Money is a relationship.

    1. How do you speak about money?

    2. How do you treat money?

    3. Do you ignore money and pretend it doesn’t exist?

    4. How much respect do you give money?

    5. Are you open to receiving more money in your life?

  5. Dreaming is a skill that requires practice. If you don’t use it regularly, your ability to dream will weaken. (Show me your calendar, and I’ll tell you how serious you are about dreaming.) The same goes for making money.

  6. You can’t do this alone—you need an accountability buddy. No one achieves this balance in isolation.

  7. One of the quickest ways to improve your ability to balance dreaming and making money is by learning from others who’ve mastered it. There are plenty of examples out there, whether through books, communities, meetups, or masterminds.


This Week’s Journal Prompt

As you reflect on today’s Deep Dive Class, take a moment to connect with your inner dreamer. Remember, the journey to balancing your dreams with financial well-being is ongoing, and each step forward is progress. To deepen this reflection, I invite you to explore the following journaling prompt:

Journaling Prompt:

Take a moment to consider your current relationship with money and your dreams. Write about a time when your dreams and financial realities were in conflict.

  • What did you learn from that experience?

  • How can you apply that lesson to your life today?

  • What steps can you take to ensure that your dreams and financial well-being are in harmony moving forward?

Take your time with this prompt, and let it guide you toward a deeper understanding of your relationship with both your dreams and your financial reality.


I hope you enjoyed today’s Deep Diver’s Class.

If you have any ideas for future classes, I’d love to hear them.

Big love,

D

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