Five Questions: Annie Howard and Betsy Lippitt

Annie Howard (screenwriter, playwright, and actor) and Betsy Lippitt (writer, closet revitalizer, and professional actress) are a creative duo currently producing an original dark comedy digital series called Detox: The Series.

They met way back as 8-year-olds in the same small town in Massachusetts that I grew up in, and eventually made their ways to Los Angeles where they currently work and reside.

One day while at my brother’s house in Central Massachusetts, I came across an article about Annie and Betsy and their web series in the local newspaper and had to get them on Five Questions. We met up a few weeks later in L.A. and talked about fighting for what you love, the frustration of living a creative life, terrible dating advice, and the beauty of psychedelic flowers. Meet Annie and Betsy.

What does failure look like to you?

Betsy: I hate this question because I’m very averse to failure. It makes me super uncomfortable, the thought of failing. I’ve said this to Annie so many times. I’m such a perfectionist that I do get frozen, paralyzed by that. Something I’m growing into is learning to enjoy when things don’t go the way I think they should go and not be afraid to label something a failure. A failure is just not meeting the mark that you set for yourself. It doesn’t have to have much more meaning than that. A failure for us with Detox would be if we didn’t make it. So as I’m evolving my relationship to failure and being less afraid to make mistakes or less afraid to try things that I could later perceive as a failure, I am finding that I’m much happier. 

Annie: Without sounding like a victim, I’ve never gotten anything I’ve ever wanted. Into the college I really wanted, the job I really wanted, the relationship. When I’ve felt that there’s one thing that I want, I’ve never gotten it. My whole life. Yet I live a very blessed existence and a full and rich and happy life. It’s just that none of my dreams have ever come true.

I come from this place that I truly have nothing to lose. Ever. The failure for me would be to leave L.A. and accept a life that I don’t want. But I won’t do that until I’m beaten into such a bloody pulp of rejection that I have no choice other than to do that to avoid throwing myself into the Pacific Ocean. That’s where I’m coming from. Ride or die. I don’t have a choice. I can’t imagine myself doing anything other than this even though I’ve never done this professionally. I’m not fully ready to quit. I’m just going to keep doing it until I’m either successful or when I feel ready to quit.

What does success look like to you?

Annie: Someone asking me to do another project if they see my work. Or any other opportunity that comes from this piece. That would be amazing. And if not from this piece, then I plan on making another piece. Getting more opportunities, continuing to be able to get my work produced. Whatever that looks like.

Betsy: I would like to say that, in the broad sense, success is being self-expressed and feeling content with what I create. And there’s that side of me that also wants recognition from the gatekeepers. People who do give you the dumb fucking note, “Put zombies in it.”

Annie: Or “No one wants to hear a story about this. Nobody likes this story. It makes people feel bad."

Betsy: And I want that person to be like, “Oh, this is good.”

Me: I love that shit. The stuff that makes you feel bad. 

Betsy: Oh, then you’ll love Detox.

A lot of those gatekeepers have very little faith in human beings and their audiences. And these notes we’re saying are real. They’re from lady gatekeepers. So what I want…I don’t want to call it validation, but it’s the understanding, the recognition that I want from them. 

Annie: It’s funny because I’ve always viewed myself as a contemporary of women like that. I see myself as inspired by Lena Dunham, but I am just like her. We are colleagues. Which is not realistic because she has Emmy awards and lots of money and she can make anything she wants, but I still see her as my contemporary. I want to sit and discuss themes with her. 

Betsy: Our dogs go to the same doggie day care so I also feel like her contemporary. [Laughter]

What's one thing you don't know now, but feel compelled to know before you die?

Betsy: You don’t know what you don’t know. 

Annie: Is that true? I’m pretty aware of some shit that I don’t know. 

Betsy: I’m tempted to say, “This language or I want to learn how to play this instrument.” But that’s not really true because if I really wanted to, I would just learn it or at least try. So that can’t quite be right. 

Annie: I want to know how it feels to have an opportunity to inspire people and touch people. All the time with my work. I had that experience once with a play that I wrote. 

Betsy: It was a beautiful play. 

Annie: Someone came up to me after this play—I wasn’t in it, but I wrote it and the writers were introduced at this place so the audience saw who I was—and this woman came up to me afterwards and told me she had never heard about—it was about grief, the play—and she said, “I have never seen grief expressed that way. So true and honest and it’s exactly what I needed to see.” And she was crying and she said, “Thank you so much.” And I was just like, “This is what I want to do for the rest of my life!” [Laughter] I said, “You’re so welcome! Thank you!”

There are writers and actors and creators and artists who get that kind of feedback from their fans all the time, people who have been touched the way that I’ve been touched and moved by art. I want to give that to people and know how that feels. 

Betsy: I think I’m still stumped.

Me: That’s cool! We’ll just go with languages.

Betsy: And the banjo. When I was a child I played the harp. I would like to play the harp again.

Annie: It’s hard to practice instruments in L.A.

Me: It’s hard to practice the harp in L.A.

Annie: “We can hear you!” That’s what my neighbors do! And then I’ll play my guitar and start singing, I’ll make up lyrics that are mean to my neighbors and go, “You chose to live in a city! And I’m playing the guitar at 2p on a Sunday and it’s not invasive!

How do you define being “in love”?

Betsy: Surrender. That’s what it is to me. 

Annie: I don’t know. 

Me: Shortest answers I’ve ever gotten.

Betsy: Well, you think things are supposed to be a certain way or you’re supposed to feel a certain way and you’re like, “Am I feeling it? Is this it?” And you’re constantly questioning yourself when I think you do know deep down. Your mind—that primitive mind—gets in the way. I always knew. Even when I was friends with my husband I was totally in love with him. I wasn’t aware of it at the time. But I was very aware of where he was in the room at all times. That’s not a normal way to relate to somebody. When I was able to say, “OK, this is it.” Then it really was and it shifted. And it was love so easily. It doesn’t have to be complicated.

I don’t know if that’s true for everybody, but that’s what’s worked for me.

Me: Annie, you sticking with I don’t know?

Annie: I’ve been told that loving someone is accepting them for who and where they are. I’m sure that applies to romantic love, but it also applies in a broader sense of How to Love. I do practice that. I’m a very loving person to most humans. Unless you come at me hard like a psycho, then I’m not into it. 

Me: That’s fair.

Annie: But being in love? It’s hard in hindsight to look at things like that. People that I have genuinely been in love with and then—it’s hard to know what the causes of those emotions really were. Actually, as I get more clarity on the causes of those emotions I recognize that it probably wasn’t really love. So I don’t know. Maybe one day I’ll know.

Betsy: What if I was like, “You should just surrender?” You would punch me in the face.

Annie: I would be like, “Stop coming at me, bro!” [Laughter]

It has been suggested to me before though.

Betsy: “You should just surrender” isn’t really that helpful to somebody. 

Me: Because you don’t know until you know. It’s the worst goddamned advice.

Betsy: Exactly! When you’re in the moment, you have the option to freak out or surrender, and my advice would be to surrender. But when you’re not in that moment, it’s not useful.

Annie: But I’ve also surrendered to my experience of being in love and the other side of that—one option is that you can have somebody be like, “Oh this is rad! All or nothing, let’s get married!” And other options are they can sleep with prostitutes or they can leave you for another woman or they can get back together with their girlfriend that they cheated on with you and then not tell you.

Betsy: Yep.

Annie: That’s the other end of surrender. Excruciating heartbreak or a lifetime of happiness. 

Betsy: I know, I know. And that’s why it’s so fucking scary. I get it.

Annie: So it’s not that I haven’t surrendered to that, it’s just that the results didn’t come out the same.

Betsy: That’s why I say I think I’m just lucky. I don’t think it’s something I did where I deserve it.

Me: I think everyone deserves love. In a sense that we’re all human beings and we’re all made from the same stuff.

Annie: Totally.

Me: However, I completely agree with you. It’s a high fucking risk. If you’re not willing to be vulnerable, then you’re fucked. If you are, then there’s a possibility…

Betsy: …there’s a possibility that you’ll be fucked.

Me: But you also start seeing that in other people. There’s a possibility of greatness as well. In every step you take. 

What will you miss the most when you’re gone?

Betsy: It makes me think of the play Our Town. Have you ever seen it or read it?

Me: Yes.

Betsy: I think it’s the third act, towards the end. This girl has the opportunity to go back and watch one day of her life. And she realizes that just being alive in every moment is incredibly miraculous. Even the smallest, mundane, small-town things that happen, can be really profound. Your question makes me think of that because if I were to come back and be like Emily from Our Town and look at any moment of my life, I imagine myself being like, “Oh! I was an idiot! I wasn’t aware of how incredible life really can be. It’s magical. And deep.”

Annie: Hmm. I’d say flowers. [Laughter] No, I’m serious. Flowers, man, are so psychedelic and trippy and so cool. The colors and shapes and geometric perfection of these dainty little things. I’m always astounded by flowers.

It kind of encompasses everything you’re saying. You have to be super present and in awe of this force that’s so much greater than anything we can comprehend to create a flower. And no two are even close to being exactly the same. 

If there’s an afterlife I’m sure they have some really cool shit like that, but who knows?