Episode 09: Why It Never Feels Like Enough Money
Kaitlyn Kessler
July 20, 2026
It never feels like enough money, no matter how much of it you actually have. I learned that the hard way in 2018, the year I hit six figures in my business for the first time. I more than doubled what the business had made the year before, and yet…
I remember being on the phone with my sister, telling her about it. She was impressed—and then she asked a question I didn’t have a good answer for: why does it still sound like you’re living paycheck to paycheck?
She wasn’t being mean. She was just confused, and honestly, so was I. I was making more money than I ever had in my life, and I felt exactly the same as I did the year before, when the business made $40,000. The same as the year before that, when it made barely anything at all. The number had changed completely—but how I felt hadn’t.
What we cover:
- Why it never feels like enough money (no matter what you’re actually making)
- What we’re really chasing when we chase a bigger number
- Why living richly now, not later, is the pathway forward
- How regulation, not income, was doing the work the whole time
Why It Never Feels Like Enough Money
I’ve seen this happen across a broad range of income levels: Someone hits six figures, and it doesn’t give them the feeling they thought it would, so they move the finish line to $250k. They get there, still doesn’t feel like enough, so they bump it up again. The inconvenient truth is that the number will keep growing endlessly while you chase a feeling that money can’t give you—
Safety. It’s permission to stop bracing, proof that we’re not going to lose it all, evidence that we’ll be okay. Money looks like the fastest way to get there, so that’s what we go after. And logically it CAN give you that, sure. But it won’t just magically do that. You can hit the number and still lie awake with the same low hum of worry (if not more!) you had before you had any money at all.
And just to be blunt: this isn’t anti wanting more money. I want more. You want more. It’s fine. But my intention is to point out that getting more money isn’t going to change what you think it will. Unless, of course, you’re willing to the work underneath it, too.
Living Richly Now
I see this a lot: I’ll relax (or have fun, or enjoy my life, etc., etc., etc.) when—
And when is always a moving target.
If living richly means waiting until everything is in place and nothing is ever going wrong, you will spend your entire life waiting to feel rich. That finish line will always be one step further than wherever you’re standing. A different approach is to start living richly now. Here’s a question to sit with: given the reality I’m actually in today, what would make this moment feel 5% richer?
Choosing to live this way will make you feel better, of course, but it will do more than that too. It’ll actually make you more money, for starters—and it’ll help you create safety within your body. When your nervous system isn’t bracing, running on urgency, operating from a low hum of danger—you have more options. You can make different choices—better choices.
Reflection prompts:
- What finish line do you keep moving?
- What’s one thing that would make today feel 5% richer?
- What does living richly mean to you?
I’ve spent over a decade in this online business space, built two multi-six-figure businesses, and coached hundreds of clients—
And I know exactly what it's like to be building something, doing the work, investing in yourself—and still feel like you're not really living up to your own potential. Like there's a version of you and your business that's juuuust there, but something keeps getting in the way.
That's the work I do. At the intersection of identity, embodiment, neuroscience, and money—I help the people who are so good at being in motion actually move more intentionally and sustainably toward what they deeply desire.
If you're curious about how I got here…
I’ve spent over a decade in this online business space, built two multi-six-figure businesses, and coached hundreds of clients—
And I know exactly what it's like to be building something, doing the work, investing in yourself—and still feel like you're not really living up to your own potential. Like there's a version of you and your business that's juuuust there, but something keeps getting in the way.
That's the work I do. At the intersection of identity, embodiment, neuroscience, and money—I help the people who are so good at being in motion actually move more intentionally and sustainably toward what they deeply desire.
If you're curious about how I got here…
