Last week, I hosted my first Ask Jay LIVE.

I genuinely loved getting to connect with everyone who showed up with me live on Zoom.

Some of my favorite moments in life are meeting people at the airport, a coffee shop, or an event. I love hearing your stories especially when I can speak with you one-on-one, ask follow up questions, and give you personalized advice.

During my first Ask Jay LIVE, I got the opportunity to do just that.

I answered questions about:

  • How to handle tough situations with your boss

  • Where to focus your energy when you are your brand

  • How to serve other people while filling up your own cup

  • How to tell your story when doing so requires you to be vulnerable

What made it special wasn’t just the questions people were asking.

It was the honesty in the room.

People called in from all over the world to share their story, and it was a powerful reminder that no matter where we live, we’re often carrying the same fears, hopes, and questions.

One of my favorite parts of the first Ask Jay LIVE was seeing everyone support each other in the chat box. People were validating the person asking a question and sending hearts across the screen as a way to say, “I see you. I feel you. I’m here with you.”

That feeling matters to me more than I can say.

So many of us are walking around carrying things we don’t know how to name, convinced we have to hold them by ourselves.

I’ve learned through my own seasons of growth that healing doesn’t always come from having the perfect answer. Sometimes healing comes when you realize there’s someone else in your corner, even a stranger, who understands what it feels like to be where you are.

Ask Jay LIVE is not just about giving or receiving advice.

It’s about creating space for real conversation, honest questions, and the kind of connection that reminds the both of us that we are not alone.

So, if you’ve been craving community, thoughtful guidance, and a space where you can show up exactly as you are, I’d love for you to join the next Ask Jay LIVE.

I hope to see you there!

Audible Original: Messy Love

I'm excited to announce that Messy Love: Difficult Conversations for Deeper Connection, my new relationship series exclusively on Audible, has just launched!

In this series, I guide three couples through resentment, broken trust, generational patterns, and more—with no script, no filters, and no certainty of the outcome.

I share in the opening episode, "We don't grow when we're comfortable. We grow when we feel safe enough to be uncomfortable together."

I invite you into this 10-episode journey, where I go beyond traditional advice and offer tools you can use in your own life, regardless of your relationship status, to create more meaningful bonds with your loved ones.

Listen to Messy Love on Audible

Today’s Wiser Choice

If you joined me in the first Ask Jay LIVE, I would love for you to hit “reply” to this message and tell me your favorite part of our session together.

If you didn’t get a chance to join, I want you to hit “reply” and let me know what question has been on your mind lately.

Want to partner with The Daily Wisdom or Ask Jay LIVE? Contact us.

The content in this newsletter is provided for general informational and educational purposes only and is not intended as, and must not be taken as, medical advice, diagnosis, or treatment. Nothing in this newsletter creates, or is intended to create, a physician–patient or other healthcare professional–patient relationship. You should always consult a qualified physician or other licensed healthcare provider regarding any questions you may have about a medical condition, your health, or any treatment options, and before starting, changing, or stopping any medication, treatment, or wellness program. Never disregard professional medical advice or delay seeking it because of something you have read in this newsletter.

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