Today’s the day!
Tickets are now open for Ask Jay LIVE
Here is what you can expect:
A virtual room full of people who feel… familiar. Not because you know them, but because you can tell they’re here for something real.
I’m there live. Fully with you.
You submit your question. And if your name is called…
You’re invited on camera. You come off mute. And we have a real conversation together… face to face, talking it all through.
My hope is that you really feel seen. Even if you never ask a question, being in community with people who are willing to share vulnerably is so powerful. Sometimes the healing happens when someone else names what you thought you had to carry alone.
Don’t wait to register as there are limited seats for this event.
Yesterday, I shared about a woman at my last Q&A who came in asking for help finding “balance.” But as she kept talking, I realized balance wasn’t the problem.
Guilt was.
She’s caring for aging parents, and she feels like she has to stay close, or else. So she’s even started bringing her laptop over there, skipping social events and self-care time, just to avoid the feeling of being away.
A year ago, I would’ve given her the “balance” answer: you’ll show up better for them when you’re rested.
But what I’ve been learning lately about guilt, as I’ve been revisiting Buddhist teachings, is that so much of our suffering isn’t the feeling itself; it’s the conflict we have with the feeling. That was the answer she really needed.
She wanted to stop feeling guilty. But how could that be possible, I asked her, when she continues to love and care about her parents? What if guilt isn’t proof you’re failing them, but proof you love them?
The weight came off her shoulders in that instant, and, if I’m honest, off mine. Because I spoke something out loud that was true for me, too. I feel guilty all the time, but I still have to live my life. So I’m learning how to carry both: guilt and freedom.
Ask Jay LIVE was built for that kind of transformation. It’s the kind that only happens in conversation… when you can talk your way to the deeper question, not just the polite one.
I can't wait to hear what's on your mind and work through your questions together on Wednesday, January 21st at 10AM PST.
And remember: if your voice shakes, or you laugh while we’re chatting, or you feel tears rising in your throat, that’s all perfectly ok.
You’re not doing it wrong. You’re probably just finally speaking the truth.
How would you show up in a space like Ask Jay LIVE?
Sometimes, it comes from choosing to learn with intention.
Coursera supports lifelong learning made simple through flexible online courses built for real life and real schedules. Whether you’re interested in learning AI at your own pace, exploring a long-held curiosity, or preparing for a thoughtful career shift, Coursera helps you build future-ready skills without overwhelm.
Through expert-led courses like Generative AI for Everyone and professional certificates online, you can strengthen confidence, streamline what drains your energy, and make space for work that feels meaningful and human.
This isn’t about racing the future. It’s about choosing career growth without burnout and learning that evolves with you.
For a limited time, Coursera Plus is available at 50% off the annual subscription through January 26.
Paid partnership
On a recent episode of On Purpose, Matthew McConaughey joins me for a deeply personal conversation.
He opens up in a way you’ve never heard before, sharing how navigating uncertainty, redefining success, and learning to trust yourself, your values, and life itself can change the way you move forward.
We also dive into identity, purpose, failure, love, his relationships, and parts of his journey he’s never shared until now.
Follow On Purpose on Amazon Music for the full conversation and future episodes.
Listen on
Today’s Wiser Choice
Try this: Let’s imagine we’re having a conversation, just me and you.
If you had the time, space, and support, what would you ask me if we were face-to-face?
Write it down now. And write down one more question every day this week.
I want you to bring those questions to Ask Jay LIVE on Wednesday, January 21st so we can explore them together.
Brought to you by Coursera
Bringing wisdom to the world takes partners who share our belief in its purpose. We’re deeply grateful to today’s partner Coursera. Without their support, our message wouldn’t reach as far or as wide as it’s needed. Please help us share our gratitude by checking out their work.
Paid partnership
Interested in sponsoring The Daily Wisdom or Ask Jay LIVE? Contact us here.








