Conversations on Passion: Matt Stillman of

Conversations on Passion is an interview series with those who have found and are living their passions in some form. If you'd like to be profiled, send me a note at

In April of 2009, I started an experiment in Union Square in New York City. I sit out there with two chairs, a table and a sign that says: “Creative Approaches To What You Have Been Thinking About”.

This is what I first read about Matt Stillman. I randomly came across his website,, two years ago and then proceeded to read every one of his recounts of the conversations he had with the people who showed up at his table.


From coping with relationship issues to handling destructive pets to making important career choices, Matt's given creative approaches to the problems people bring to him. Drawing on the knowledge he's acquired of an absurd amount of facts and by looking at life through a slightly different lens than most of us, he's helped thousands of people think a little differently about the personal battles we face.

I recently had a chance to sit down and have a Skype call with Matt to discuss his own passions, how his life has led him to this point, and to get some creative approaches on how to find passions and incorporate them into our lives.


What is passion to you?

Of course there is the etymological meaning of passion, which is to suffer and to experience deeply. Like the Passion of Christ. And there is something about passion that has a sort of suffering edge to it. For me passion is something about "What do you burn for?" And that has a negative and a positive, a front and a back, an active and a passive aspect.

What are some of the positive and negative sides you see?

I think something about the experience of passion, if you immerse yourself in it totally, starts to burn you up. It starts to transform you. If you stick your finger in a fire, there is pain, but there is also transformation. It might start to roast, it might permanently change shape, but it might also make you more acutely aware of where you want to put your finger. Passion is something that you need to interact with to see how it shapes you, because you may not need to be around it, you may need be warmed and lit by it instead of being burned by it.

What are you passionate about?

I'm passionate about play and about service. With play I think there's at least two types of play: finite games are played to be won, and infinite games which are played to be played. Neither is better or worse, but they lead to different experiences. Often my experience with passion is that people take it to a limited field of play; they are hoping to use their passion to win or to elevate or to beat someone or to get status or to have a title.

Other people use their passion as a way to experiment with boundaries and see where it could take them, that has nothing to do with them in the end. That's where service can come in. And that's a shift between a me-centered or an other-centered.

There are plenty of groovy hippies, who want to serve the world and don't care about “me”. That's cool, but you need to feed yourself, take care of yourself, and not deplete yourself. And you also have the counter to that who is the wall street “dick”. The one who says, “I'm passionate about mergers and acquisitions, and I'm going to make money so I can win,” and that ends up serving no one but himself.

I try to figure out how to move with my passions instead of feeling fixed to it. And how to keep other people involved and relating to it in new ways.

Tell me a little more behind what got you started doing what you do in Union Square?

I was taking a class in 2009 called Creativity and Personal Mastery, when near the end of the course, one of the assignments was for everyone to write a love letter to the other people in the class. And so I received a 24 page book from my classmates, and what every single one of them said was that I was really incredible at helping anyone look at seemingly any problem in a really creative and helpful way. I didn't always solve the problem, but I helped them look at it in a new and creative way. And that I should find some way of doing something with that.

It was really moving and touching. I had heard that before, but never with 24 pages all at once. And I also hadn't heard it in a time when I suddenly had a lot of space. I had just been laid off from a consulting gig a few weeks prior. This was the middle of March 2009, and the economy had just collapsed.

I decided to offer a creative approach to myself and got two folding chairs and a table, set them out in Union Square on April 1st, 2009, and on the very first day 30 people showed up. I was amazed, I didn't know what was going to happen. I thought I'd do this and ride this out until something else happened or it made itself clear what it is. After a while I decided to blog about it, and it's been profound and moving and touching and amazing and surprising.

What about some of the other projects you're working on?

I've been a professional plate-spinner... I've done a whole bunch of stuff since then: I've turned that experience into a little business, offering creative approaches to businesses and people, I teach the Creativity and Personal Mastery Course now, I'm an author and have written a few books, I'm a landlord, I'm a part-time CrossFit Coach, I have a sitcom sitting with an agent...and I'm interviewing for regular straight jobs as well. I'm also launching a skincare business.


Why interview for regular jobs if you have all of this other stuff going on?

I've been a hustling plate-spinner for a long time and there's been times when it has really gone well and there are times when it's definitely been dry and that's dependent on a lot of things. I think it's important in life to not just paint with one color, to use an artist's analogy, and I've been painting with the freelance, hustler's color for a long time. I think if you're a real artist, you need to have a range.

Would you say that you're passionate about coming up with Creative Approaches?

I've definitely been passionate about what I'm doing in Union Square, but I've had different degrees of passion. There have been times when I've burned for it and all I've wanted to do is be there and then there are times when I'm warmed by it, and I've put a little distance. I'm always delighted by it and I have a great affection for it and I love doing it. It's one of the places I feel very much at home, but my energetics towards it shift. It always feels like play and service. I try to get the other people involved, and it's always for the other people. I've heard very kind things and I'm very grateful for that, but I try to make the focus on sharing what happens and not on me.

Would you consider yourself passionate about other things as well?

I would, and I think play and service come up in those as well. I'm interested in smashing things together that don't always make sense. I'm interested in making things on opposite ends come together and see what happens there. My book of biblical erotica is an example of that. Like really, “Biblical erotica written in Elizabethan English?” Many people have found it very thoughtful, profound, and helpful.

Do you find your projects have changed the way you approach your passion or how it manifests itself in your life?

I think that mostly my projects have been based around this core theme of play, service, and improvisational exploring. And that kind of comes out in starting something, seeing what rises up to meet it, and seeing how that moves it. If no one had showed up that first day I was in Union Square, I couldn't tell you how that would have changed it, but people rose to meet it. And there have been other things that people haven't risen to meet.

Can you tell me about a time when things didn't work out when you applied your passion and how you dealt with that?

One example was when I was involved in a political science, economics think tank, where we met weekly for two years to write new economic break out thoughts. It was fantastic, we had book-sharing and collected documents and wrote text and conducted interviews. Then I had something disruptive happen in my life, and similar things happened to two of the others, so we had to take a step back. The fourth person was upset and felt we had abandoned the project, and decided to move on without us. Eventually it became a book that I wrote the foreword to. I learned stuff from the process, but I don't have much to show for it in terms of money or depth.

How do you think your life experiences have shaped the way you approach these projects and your passions in general?

I would say that my experience studying long-form improvisational comedy with Amy Poehler and the Upright Citizens Brigade, was hugely formative for me. Also, being raised by mystics doing deep spiritual, introspective work and being open to not dictating where things would go, was really influential.

What tips would you give to others to help in finding their passions?



Try one thing that you think would infuriate or make your parents ashamed. Sometimes it takes you in a direction that you normally don't think of. It's a pattern break. It's easy for people to say "I like this," or "I like that," but what about to say, “What would make my parent's angry at me?” Not that you should or shouldn't do it, but it takes you in a different pattern.

Express gratitude to people who've made a difference in your life. Tell them where you are in your life and how they helped you to get to where you are. We have the illusion that we have succeeded and failed on our own because we live in a very individual world. If pushed, people will say they had help along the way, but will say it's ultimately been their own experience. But everyone experiences periods of feeling lonely and lost, and expressing gratitude and really being specific about how someone has helped you is touching, but it also opens up doors. They may say here's someone you should meet or a book you should read, and it reveals the hidden web of support, insight and direction we often feel lacking. It helps you deal with passion in a different way because you don't need to burn alone.

Follow Matt on Twitter: @stillmansays