Episode 985: Show Notes

So many of us think money is the ultimate benchmark for success, but what if we’ve been chasing the wrong thing all along? In today’s episode with Ryann Gillen, we’re pulling back the curtain on the subconscious beliefs that quietly shape the way we do business and often hold us back. Ryann is a transformational leader and mentor with decades of experience building multimillion-dollar sales teams. She now helps ambitious women break through limitations, reclaim their power, and actually enjoy the businesses and lives they’ve built.  

She did all the things “right,” hit the goals, and still felt something was missing. Sound familiar? Together, we talk about what it means to decouple your self-worth from dollar amounts, why chasing feelings instead of things is the key to freedom, and how nervous system regulation plays a bigger role in business than most people ever admit. Ryann’s energy is magnetic, and I know you’re going to walk away with so many ‘aha’ moments.

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From Corporate Sales to Personal Development 

Ryann spent 15 years in a traditional corporate sales career before stepping into entrepreneurship. Like so many of us, she thought success was about following the formula.  Five steps, one process, guaranteed results. When she launched her first program in 2019, over 200 women joined, and yet she couldn’t figure out why some thrived while others struggled despite doing the “right things.” 

At first, she blamed herself. Maybe she wasn’t a good teacher. Maybe she wasn’t cut out for this. But as she dug deeper, she realized the problem wasn’t her program; it was that strategy alone wasn’t enough. The missing piece was the inner work. Entrepreneurship forced her to introspect and to ask herself, Who am I? What do I want? Why do I keep repeating the same patterns? 

Ryann never planned on teaching personal development, but once she discovered how transformative it was, she couldn’t keep it to herself. She saw how much more powerful women could be if someone finally gave them permission to play by a different set of rules, rules that didn’t require fitting into a rigid, masculine mold of business. 

Redefining Success Benchmarks 

Money is the benchmark for all businesses. For years, Ryann tied her self-worth to her income. If she hit the number, she felt good. If she missed it, she spiraled. Maybe you’ve been there too, constantly raising the bar, only to feel like it’s never enough. She realized this way of operating was unsustainable. There will always be someone making more money. There will always be another dollar goal to chase. And if that’s your only metric, you’ll always feel behind. 

Ryann decided to shift the way she measured success. Now, her benchmarks are, “Am I keeping the commitments I’ve made to myself? Are my clients thriving? Am I spending my time in ways that feel good?” When she made this decision, everything changed. Now, she can wake in the morning without money on her mind as the main benchmark. Ironically, the money flowed more easily, not because she was chasing it, but because it became a byproduct of the things that actually mattered. Shifting her focus away from money has fueled her creativity and passion, making her a better entrepreneur. 

Focusing on People and Becoming the Product 

After redefining her benchmarks of success, Ryann shares how her attention shifted to people and the product itself. Since she is the product, her coaching, her teaching, her energy, the best way she can serve clients is to become a living example of the transformation she teaches. By embodying her own work, she not only proves the process but also attracts clients who see the results in her. 

However, shouldn’t money be the first focus, and only once you’ve made enough can you afford to shift? Ryann’s answer is powerful: no. If money is your only goal, you’ll always feel behind, and financial security will look different for everyone anyway. Instead, she encourages entrepreneurs to focus on impact and embodiment right from the start, letting money flow as the natural byproduct of your process.  

Chasing Feelings, Not Things 

Ryann tells this great story about the boat that’s been on her vision board for years. Like so many of us, she thought owning a boat would mean she had “made it.” But when she really looked closer, she realized it wasn’t the boat she wanted; it was the feeling. 

She wanted the joy of pulling her kids on a tube, blasting music, and eating sandwiches out of foil like she did growing up. And she realized she could create that feeling right now without buying the boat. Renting one, or simply recreating those experiences elsewhere, gave her the same joy. 

That’s the heart of Ryann’s message: it’s never the thing itself. It’s the feeling we think the thing will bring us. Freedom, safety, clarity, fun. When we learn to generate those feelings now, before the vision board items arrive, everything else falls into place so much faster. 

Balancing Gratitude and Desire 

One of the tensions we all feel is between gratitude for what we already have and the desire for more. Am I being greedy? Am I not grateful enough? Ryann reframes this beautifully. She explains that it is not about choosing one or the other, it’s about walking with one foot in gratitude and one foot in desire. Expansion is natural. We’re meant to want more. However, when we need to stay rooted in appreciation for the clients, opportunities, and experiences already before us, we create space for the next level without slipping into a state of lack. In her mind, there is no such thing as work-life balance but rather a balance between gratitude and desire.

She reminds us that you can be deeply grateful for one client and still excited for the 20 that are coming. You don’t need to feel joy all the time; that is unrealistic. Aim for contentment and gratitude. Remember, you can appreciate today while imagining tomorrow. It does not have to be a choice. 

Helping Clients Clarify Their Desires 

So often, when I ask women what they really want, they either have hyper-specific clarity or absolutely none at all. They just know, “It’s not this.” Ryann shares how she helps her clients move from confusion to clarity. The process starts by naming what you don’t want. On the other side of every “I don’t want this” is the desire for something else. Ryann’s question to herself, “I don’t want a full calendar,” flips into “I want white space.” Then she asks the deeper question: why? What does that give me? For Ryann, white space creates creativity, freedom, and the chance to think. 

It’s always about the experience and the feeling underneath the goal. Nobody actually wants “money” just to stare at numbers in a bank account. What they want is the feeling of security, freedom, or joy that they imagine money will bring. Once her clients see that, they can start creating those feelings now, instead of holding their happiness hostage until a future milestone arrives. 

Making the Work Feel Worth It 

Even when we do take the walk, slow down, or give ourselves space, so many of us immediately feel guilty about it afterward. You have to reframe the way you see it. 

Ryann teaches her clients to view themselves as the most valuable asset in their business. And what do we do with assets? We take care of them so they appreciate. That means the walks, the journaling, the breathwork, and the slow mornings. They’re not luxuries. They’re maintenance. They’re part of the work. 

If she doesn’t take care of herself, there is no business. Period. By treating self-care as business care, she not only feels better but also has better ideas, more creativity, and more energy for her clients. Ryann even suggests adding these practices to your to-do list, right alongside client calls and deliverables, because they matter just as much. 

How to Recentre When You Get Distracted 

So what happens when life pulls you off course? Ryann says the hardest part of all of this is actually believing how much