Waking Up With Ryan

What if the people who hurt you most didn't stumble into your life by accident — but signed up for the role? In this episode of Waking Up with Ryan, Ryan shares a powerful visualization: imagining your soul choosing every relationship before you were born, including the ones that challenge you the most. He explores how the people who push our buttons aren't obstacles to our growth — they're catalysts for it. Through a g...

Life doesn't always go according to plan — and that's exactly where the growth happens. In this episode of Waking Up with Ryan, we explore what it really means when things don't work out the way we hoped, and why those disappointments aren't obstacles to your healing — they're doorways to it.

Drawing on the Yoga Sutras and a reminder from Leonard Cohen ("The crack is where the light gets in"), Ryan walks through how our...

Most of us were taught that believing in ourselves too much is arrogant — that playing small is humble. But what if that belief has it completely backwards?

In this episode, Ryan explores the difference between the ego's grip on your identity and the truth of who you really are. He breaks down why knowing yourself as a light, as an extension of the divine, as something miraculous — is actually the most humble thing you ...

What if the destination you're chasing doesn't exist? In this episode, Ryan dismantles one of the most common traps on the spiritual path — the belief that awakening is something you arrive at, rather than something you're already living.

Drawing on the wisdom of Byron Katie, Gangaji, and the great enlightened masters, Ryan explores why comparing yourself to "awake" teachers keeps you stuck, what it actually means to love wha...

Ryan sits down with actress Jennifer Grey about what a good death can look like. They discuss her mother's recent passing and what it meant to be truly present for someone as they leave this world — being hyper-intentional and dignified in those final moments. They explore how facing death instead of turning away from it can actually help us live more beautifully right now: the gift of a terminal diagnosis, the power of forgi...

In a world flooded with noise and competing agendas, how do you know what's actually true? In this episode of Waking Up with Ryan, we explore why questioning your own beliefs — not just the world's — is the first step toward clarity. Ryan unpacks why your mind works like a sponge that's absorbed a lifetime of other people's opinions, and why real presence begins with the willingness to be wrong.

You can follow Ryan on I...

You never know whose life you're quietly shaping. In this episode, Ryan shares a powerful moment from a dance class where he learned, years later, just how deeply a single act of kindness had impacted someone's entire life path — a reminder that our presence, energy, and small choices ripple further than we realize.

Ryan explores how showing up with love, compassion, and presence can change the trajectory of someone's day &md...

We talk a lot about boundaries in personal development — but what if you've been thinking about them all wrong? In this episode, Ryan reframes boundaries not as walls meant to keep people out, but as sacred, inclusive spaces you get to fill with what you truly want: love, emotional intelligence, creativity, and honest connection.

You'll learn how to communicate your boundaries with clarity and compassion, turn conflict into d...

Maya Angelou once said, "People will forget what you said... but they will never forget how you made them feel." In this episode of Waking Up with Ryan, we explore what it really means to make someone feel loved, seen, and safe — and why that starts with how safely and authentically you're able to be with yourself.

Ryan unpacks the real root of connection: not achievement, not what you say or do, but the felt sense of permiss...

Most of us wait for the big breakthrough — the retreat, the plant medicine ceremony, the peak meditation — to feel spiritual connection. But real spiritual depth isn't found in rare peak moments; it's found in how you meet this moment, right now.

In this episode, we explore what happens when we forget the sacredness of the present — even in the middle of the most ordinary tasks — and how a simple shift in at...

Most of us have been sold the wrong idea of meditation — the image of a serene person sitting in perfect stillness, blissfully at peace. So when we sit down to meditate and instead find noise, restlessness, and discomfort, we assume we're doing it wrong… or that meditation just doesn't work for us.

In this episode, Ryan explores a definition of meditation from spiritual teacher Adyashanti that reframes the entire pract...

Horses have been reading human energy for millions of years — long before words existed for emotional awareness. This episode explores what equine therapy reveals about trust, discomfort, and the parts of ourselves that tend to get pushed down and avoided. Horses stop the moment there's a mismatch between what someone feels inside and what they show on the outside — and the same holds true for people in daily life. You ...

What if the very thing you're chasing — the relationship, the career, the money — is being pushed further away by your need for it to happen?

In this episode of Waking Up with Ryan, Ryan explores why grasping for what we want (or forcing ourselves to "let go" of it) misses the real work: building a relationship with your inner world. Drawing from a conversation with an old friend who's spent decades wanting a relationsh...

We spend years striving for awakening — more practices, more books, more teachers, more effort — but what if the very act of striving is what keeps it out of reach? In this episode of Waking Up with Ryan, we explore why awakening isn't a destination to arrive at, but a truth that's already here, right now, underneath the mind's stories about who you are and where you're headed.

You can follow Ryan on Instagram (@wakingu...

They met backstage at an NSYNC concert twenty-five years ago and stayed up until 5am laughing. They’ve been showing up for each other ever since.

In this live conversation from the Waking Up with Ryan launch in Venice, actresses Jenna Dewan and Emmanuelle Chriqui get honest about what it actually takes to keep a friendship alive for a quarter century, especially two women in the same industry, often up for the same roles.

The...

What if the way you live today is preparing you for how you'll face your final moments? In this episode, Ryan shares a deeply moving story from a recent experience — being invited to sit with a dying woman and her family in her last hours, guiding a ceremony of prayer, meditation, and release. What unfolded was one of the most powerful teachings on forgiveness and freedom he's ever witnessed.

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Being human is inherently strange—we're infinite, boundless awareness crammed into a small body, juggling emails, money, and relationships while forgetting who we really are. In this episode of Waking Up with Ryan, Ryan explores why life feels so hard, drawing on a Talmudic teaching about the soul forgetting itself at birth, and compares our everyday experience to a nightmare that feels completely real until we wake up.

You c...

Your life is hard. There's stress, pressure, and a constant stream of self-judgment — but what if the answer isn't to fight your ego, but to love it?

In this episode, Ryan explores a question: Can you love your ego? He unpacks why resisting your ego only strengthens it, why "spiritual bypassing" can become its own form of toxic positivity, and how true love means making space for every part of your experience, ego included.

Y...

Have you ever judged someone for having the exact thing you want in your life? In this episode, Ryan unpacks why the people who trigger your jealousy might actually be proof of what's possible for you, not evidence of what you lack. Ryan explores how competition and comparison can quietly kill our manifestation, and why gratitude — real gratitude for what's already here, not some imagined future — is the true open door ...