Stop Chasing Money and Start Deserving It

What we talked about.

In this episode of The Sunny Ray Show, host Sunny Ray welcomes back returning guest Reagan for a wide-ranging, unscripted conversation built around the theme stop chasing money and start deserving it. Reagan opens by explaining his signature line, I'm doing better than I deserve, tracing it back to the simple fact that none of us chose where we were born. From there the conversation moves into gratitude as a practice, with Reagan sharing a story about a man who wanted life advice over lunch but never said thank you for his blessings. The two dig into morning routines, habit tracking, and the difference between chasing outcomes and becoming the kind of person who attracts them. Reagan talks about writing by hand as a personal practice, community giving in his Coral Gables neighborhood, and how faith differs from wishful thinking when imagining a better future. The episode feels less like a structured interview and more like two friends thinking out loud, landing on practical takeaways about gratitude, routine, and generosity that listeners can apply immediately.

Sunny Ray and returning guest Reagan trade morning routines, gratitude habits, and hard-won wisdom on why deserving success matters more than chasing it.

The questions, and the answers.

What do you mean when you say you're doing better than you deserve?

I didn't have a choice about where I was born, and neither did you. I could have been born in a village in Africa without clean water to drink. Since I usually begin my morning with a glass of water, I realize I'm already doing better than I deserve. That simple awareness changes how grateful you feel about your whole day.

Take me into this idea, stop chasing money and start deserving it. Tell me about that lunch conversation you mentioned.

Someone recently asked to meet for lunch because he wanted answers about deserving things. I noticed he views life as if he's owed it, so when something good happens he never says thank you. I told him to think about being grateful before the outcome even arrives. Afterward I realized I'm not fully there either. I say thank you once a blessing shows up and I give back, but I'm not always grateful beforehand, and that's worth working on.

How important is the physical process of writing versus something like voice journaling?

So much of it is in the actual writing. I do it with a pen and paper, and that's what I like to do. When you write the first letter of a word, it reminds you of something else, and there is so much more that comes out through the physical act of writing itself. I even write with both hands. I love writing. That is my favorite thing to do.

When you imagine your future and try to feel grateful for it, how do you know it's real faith and not just wishful thinking?

When you're down on your luck, you tend to believe more, that's just psychology. If you had one chip left in Vegas, most people would swear they still had a ninety percent chance to win, even though the odds never changed. Hardship makes you believe harder. So if your dream feels grandiose, that's okay. You might not reach all of it, but if you reach even half, you're still in a better place than you are now.

How did the habit of giving back a percentage of what you earn in your community start for you?

I live in Coral Gables, a walkable suburb of Miami, and I try to have real conversations with the people I pass every day, the barista, the person at the hotel desk, whoever I see. Through those conversations I can intuitively sense when someone has a need, like a single mom waitress going through something unexpected. In moments like that I'll give more than a normal tip, because paying attention to your community naturally shows you where to give.

What would you tell someone who says they don't have time for a morning routine, or for giving back?

For giving, you don't need much, an extra ten or twenty dollars in cash to someone you see regularly can mean a lot. But the better answer is this, if you genuinely have a desire to help the community you live in and you take time to talk with people and actually listen to their needs, opportunities to give will show up on their own, simply because that desire is already in your heart.