There's a version of New York success that works exactly the way it promises. The title comes. The name gets made. And somewhere along the way, you notice that the thing that was supposed to fill you up hasn't. Ambition can run dry even when it's working. Remember, fruit isn't what you produce. Fruit is what your life produces in someone else. And that's what we're going to talk about this week with Caitlin.

Caitlin moved to the Upper East Side in August of 2024 for her career as a consultant with a prominent executive search firm. She came with a clear ambition: to make a name for herself in this city. She started attending Church of the City in 2025, and it was there that she powerfully encountered the presence of God. Then, in the middle of a personal crisis, Jesus stepped in and invited her to do something that made no sense on a résumé: lay down building her kingdom, and join him in building his. Today, Caitlin carries a real burden for the Upper East Side. She's seeing God move in power through one-on-one conversations, often with total strangers, in her neighborhood and in her workplace. At Church of the City, she hosts a community group, serves on our connections team, and leads with our Send Saturday teaching and equipping team.

In this conversation, we talk about what it actually looked like to lay down ambition, and what that cost. We talk about how a vision for evangelism took root, and what it looks like to start a conversation with a stranger on a New York block. And we talk about what she'd say to the person who has done everything right and still feels the ambition running dry.

A Manifesto of Fruitfulness invites you into real conversations with people from Church of the City New York who are learning what it means to bear fruit. Not in what they produce, but what their lives produce in someone else—in a marriage, a friendship, a block, a job. Doug and Lisa have been part of Church of the City New York since 2019, though their story starts long before that — thirty years of marriage that began in Atlanta and led them to Denver, Amsterdam and Hong Kong, some of those cities more than once, before New York finally became home. Doug spent over 35 years in the insurance industry, starting as an actuary and now serving as Chief Risk Officer for a large retirement and life insurance company — a career built, in his own words, on trusting what he can't fully control. At Church of the City, Doug and Lisa lead a community group and mentor couples preparing for marriage. Doug also serves on the Board of Overseers.

We're going to talk about what it looks like to hold money loosely instead of tightly. Why they believe you genuinely cannot out-give God. What it cost them to wait years for New York to open up, and what it meant to quit a job with no plan for what came next. And what thirty years of marriage has taught them about showing up for someone else's life instead of just your own. Doug and Lisa have a lot of hard-won wisdom to offer for anyone who desires to live a fruitful life. We are so grateful for our conversation with them and are excited to share it with you.