Thank you for sharing that with me. It’s exactly the kind of thing I sense in people when they meet me, even when they don’t say it out loud. So, I want to paint a picture here for you:

Imagine you’re back in school.

You’re working on an assignment for Math class. And there’s a problem that is just not making any sense to you. You try and try and try, and you eventually give up and decide you’re going to ask your teacher for help.

The class is really big, and the teacher doesn’t know anyone by name. You build up the courage to ask the question.

The teacher, trying their best to cater to the entire class, generalizes the answer. They explain, but not in a way that’s helpful. You want to ask a follow-up, but there’s no time. You’re no closer to understanding the problem, and now you’re embarrassed.

I know I’ve been there. It’s a tough feeling. The impersonal, high-stress, isolating feeling of not knowing.

In my work, that’s something I want to avoid. Which is why in the new year I’m launching a new way to interact directly with me. It’s a monthly, virtual series called Ask Jay Live. (Stay tuned here for ticket information!)

Ask Jay LIVE is a live question and answer experience, where you can come directly up on the screen, face-to-face with me, and ask your question.

I’m so excited about this experience we’re building for you. I love seeing real people. I get so much from talking to a human. The emotion on your face. The tone of how you ask a question. It’s so rewarding for me.

When you ask your question in the comfort of everyday conversation, it doesn’t need to be polished or pre-rehearsed. It doesn’t need to sound like an academic submission. You don’t have to nail every word on the first try.

You can simply speak.

We can be human together. You can be honest and I can be a little messy.

I can also have an easy back-and-forth with you, asking follow-up questions, helping you get to what you actually mean.

This isn’t a one-and-done exchange. It’s happening every single month, beginning in January. That’s how community forms: not through big moments, but through repeated human interaction.

For me, this special New Year’s project is a chance for you to be heard and to feel supported in a real way.

And for me, it’s a beautiful way to build a community of people who are choosing purpose, over and over again.

Throughout the year, we partner with brands that support intentional living and personal growth. As we step into the New Year, we’re highlighting a few favorites that align with fresh starts, meaningful habits, and the intentions we carry forward.

Connect your email, and you’ll instantly get a CRM with enriched customer insights and a platform that grows with your business.

With AI at the core, Attio lets you:

👉 Try Attio Pro for free

On last Friday’s episode of my podcast I spoke with the incredible musician Jahnavi, whose music is based in sacred song and mantra. Her music is so spiritual and powerful, but in her interview she describes how she’s a human being who has material wants and makes mistakes, too. We talk about finding confidence in herself and finding herself through music. If you’ve ever struggled to find your voice, and are searching for a way to serve and connect to this moment, Jahnavi’s story is an inspiration.

If you want to feel inspired, learn practical tools, and hear powerful stories, follow and listen to On Purpose on:

If you’re a reader of this newsletter, chances are you’ve dealt with your fair share of challenges that you’re seeking wisdom to work through.

Try This: What’s one question you’d love to ask me? And are there specific types of questions you’d want to hear from others? Write them down and get ready for when tickets open to my very first Ask Jay LIVE event of 2026!

Relationships take care and attention, but managing them shouldn’t feel complicated. Attio offers a clean, intuitive way to keep track of important people, conversations, and commitments, all in one place.

Whether you’re running a business, supporting a growing project, or simply juggling many meaningful connections, Attio helps keep your communications organized without overwhelm. Clear, flexible, and easy to use, it’s designed to support thoughtful relationships at every stage.