A few years ago, Anna Margaret Hollyman was on vacation with her husband in the Caribbean just after New Year’s where local tradition holds that everyone must jump off a cliff into the water, just after the page turns on the calendar. With a crowd forming, all hooting and hollering, Hollyman was enjoying herself quite a bit until the chants turned towards her to take the plunge.

“It was perfectly safe, but I stood on the edge and just couldn’t do it,” recalls Hollyman, in reflecting on the moment she knew she might finally make good on her idea to make her directorial debut “Maude.” “I think the actor in me was so humiliated that I was like, ‘Well, there’s an audience, so I’ve got to jump now.’ It was such a metaphor for this movie where I kept saying I was going to jump in, I wouldn’t jump in and then finally a group of people – no less than 10 – my husband included, were constantly on repeat, being like ‘Just make the movie, make the movie.’”

That number surely would’ve been even bigger had more people known that Hollyman was even considering going behind the camera, since the actress has cultivated a robust fanbase on the film festival circuit following leading turns in such films as Lisa Robinson and Annie Howell’s “Small, Beautifully Moving Parts” and Zach Clark’s “White Reindeer,” not to mention the many memorable shorts she’s starred in. Gifted with a wry sense of humor and a beguiling air of mystery around her as one can often see the wheels turning in her head without knowing exactly where she’ll land, Hollyman has been continually called on by writer/directors with distinctive voices to carry out their vision, so it was likely only a matter of time before she embarked on a film of her own.

She does not disappoint with “Maude,” a 10-minute delight in which she plays a young woman named Teeny, who unexpectedly finds herself at the luxe home of a high school classmate (Megan Ferguson) after answering an anonymous online ad for a babysitter. The realization causes Teeny to wonder about her station in life as she pushes around the woman’s baby around town, using the assumption of passersby that the baby is hers to imagine herself living the life that she wishes she had. Like many of Hollyman’s signature performances, “Maude” is instantly inviting, demonstrating the same wit in her visual choices as she’ll often imbue in any given piece of dialogue, yet grows bittersweet as it wears on, simultaneously showing the promise Teeny still holds and alludes to all the times that she, and other elements out of her control, have gotten in the way. Honoring its short form with a heck of a punchline, “Maude” doesn’t only end with an uproarious finale but one that lingers since Hollyman gives Teeny such depth.

Shortly before flying into Park City for the premiere of “Maude” at Sundance — now with a real newborn of her own, Hollyman generously spoke about how she overcame her own fears to take her rightful place in the director’s chair, the aforementioned support system that encouraged her to take chances and how empowered she felt in setting the tone for the kind of family-friendly set she wanted.

Anna Margaret Hollyman in "Maude"I may be connecting dots where there aren’t any, but from the roles you’ve played, I’ve always thought of you as a bit of a cerebral actress, where the action can be working out your thoughts onscreen, and had the sense there’s an an attraction to characters that live in their imaginations, which isn’t to say they have their head in the clouds, but they’re constantly thinking about what’s not right in front of them. “Maude” would seem to fit that description, so is that actually a throughline?

I never thought of myself as a cerebral actress, but I see what you’re saying. I remember my friends Lisa Robinson and Annie J. Howell, who did “Small, Beautifully Moving Parts,” said to me once, “You really are at your most comfortable in a closeup.” [Lisa] said, “I do feel the intimacy between you and the camera, when you’re processing things is where you feel the most comfortable,” which is strange for a lot of actors because you would think you’d feel the most comfortable in a wide [shot] or when you don’t have such a intense, intimate lens upon you. With the filmmakers that I’ve worked with, like [“Social Butterfly” director] Lauren Wolkstein, [“Woman of the World” director] Allison Cook and even [“The Mink Catcher” writing/directing duo] Sam Buck and Marie Schlingmann, there is something about them being female writer/directors where they bring out this side of things that all women respond to, and I do think this movie is an extension of a lot of characters that I play, which is why I’ve enjoyed playing all those characters so much. I am in my head a lot of the day [laughs], thinking through a lot of hypothetical situations or imagining what could be or how I would react in certain situations, partly because it’s interesting and fun for me, but also because I think everybody lives like that.

When I first talked about the idea for “Maude,” it was based upon my own experience and fears that I was going through at the time. The way I like to deal with my own anxieties and fear is through self-deprecation and humor, as much as possible. If I can laugh through humiliation and fear, it always feels a little bit more palatable to me, so when I came up with the idea [of], “What if you just were babysitting the child, people assumed you were the mother and you simply didn’t correct people and you saw where that choice took you,” when I would tell other women about that idea, nine times out of 10, every single woman I spoke to said, “Oh yeah, I used to do that all the time when I babysat.” I even had a girlfriend [who] went into a store a few years ago, where a shopkeeper mistook her for a woman who was married with a child and she said, “Oh, your husband just came in here with your baby and the baby looks so great and your dog,” and my friend, for some reason, went along with it. [laughs] And pretended that she had this life that she didn’t. She called me afterwards, laughing and horrified with herself, like, “I don’t know why I did that, but I just felt like bad for the shopkeeper. She was so convinced I was someone else, I didn’t want to correct her out of politeness and then the other part of me was like, ‘This is kind of funny. Why not?’”

So I think that there’s a part of me and maybe in a lot of women that I know who, like the other characters I’ve played, who live with one foot in the imaginary or the hypothetical of what could be and I think women in particular are constantly examining their identity because we have these archetypes that have been presented to us and that [we] feel [we] have to take on or live up to or check off. It’s either like the mother or the career woman and then there’s this overarching umbrella of like…”and you’re supposed to have it all.” And I know for most of my girlfriends, it’s almost like you have a second adolescence when you start taking on an adult identity, like becoming a mother or a wife or a businesswoman. If you’re running your own company, for example, you constantly wonder if you’re passing, like “Do I look like a grownup? Do people respect me? Do people think I’m a capable human being in the world?” There’s so much self-doubt that’s under the surface. That’s why it’s interesting to me to be in movies that explore what could be behind door number three – what life might be like if they had chosen a different path.

Anna Margaret Hollyman in "Maude"Did you plan to star in this from the start?

I did. I went back and forth [a little] because having never directed before, I thought it was a little too ambitious to direct and act in it, but one of the things about [living in] Austin that’s really wonderful is that it has this really supportive, vibrant film community, so it just took the edge off a little bit. I figured if it goes horribly awry, it’s fine, I only have myself to blame as the lead. [laughs] And truth be told, I live in this indie realm, so I felt like it was a way for me to push myself forward creatively and professionally because even though I love working in independent film — it’s my home and it’s where I always want to work — there’s always this expectation that you’re supposed to have this “breakthrough” or “breakout” on a more commercial level, whether that’s booking that HBO show or finally getting on a network show and “making it” and I think there’s a little part of me that still has this secret hope that that would happen, but also there’s another part of me that’s accepted that that may never happen, so if that’s the case, I really wanted to try to see what it felt like to take control over my own career. In casting myself, it felt like for a moment I could let go of that insecurity of knowing if you’re going to get the part. And [making “Maude”] has changed and shifted my entire attitude about casting and auditioning in general. Can you tell the short was just like self-therapy for me? [laughs]

If it was, you fooled me.

The short was an exercise in self-confidence for me in a lot of different ways and for different reasons. I’m always afraid of being too ambitious or maybe not qualified enough to do something and instead of letting those [fears] take over in my head, I was just like “Let’s do it. Let’s push forward. Let’s try it. What’s the worst thing that could happen?” And I’m really happy that I did. It was just actually filmmakers I’d worked with saying to me, “You should write and you should direct” [that gave me the confidence]. Annie [Howell] said to me, “Write the script, just think of it as a creative exercise and go from there, just to prove to yourself that you can do it.” And [actually] as I’m talking to you, there’s a notebook on my desk that’s embossed and it says “The Untitled AMH Project” that was given to me by Samantha Buck and Marie Schlingmann a few years ago and they said, “This is for you. You need to start writing.” My friend Jason Klorfein, who is one of the producers who I’ve known for years, we met for lunch in New York a year-and-a-half ago, and he said to me, “I really think you have a unique voice — a writer’s voice — and I think you just need to write something. I’d love to make it with you.” He gave me the confidence as a jumping off point because I had had this idea in my head for years. So I really chalk it up to the support of all these talented people who I’ve had the privilege of working with who all became my coaches. Any time I had a thought of pulling back or maybe we should push the date, or [thinking] “I don’t know if I’m ready” or “Maybe I should cast someone else,” I had a great support group of people going, “Nope. Stop. Move on. Keep going.”

What was it like finding your precocious co-star?

That baby Mabel is probably the best behaved, calmest actor I’ve ever worked with. [laughs] She’s now almost two, and I remember when I wrote the script, Jason was like, “Just write it. Don’t worry about it too much [about casting the baby]. We’ll figure it out.” Then my other producer Bettina Barrow came on and she’s a mother as well and she’s like, “I have a baby. My friends have babies. It’s not a big deal. [We’ll find one.]” It was probably totally delusional [to think] “Great, we’ll do the baby later. That’s not going to be the hard part.” But when I finally [finished] the script, I just went, “Oh my God, I did what they tell you exactly not to do with your first film – which is don’t put a baby in.” They always say if you want your film to get into film festivals, put a baby in or put a dog in and I’ve got a really cute dog, [so I thought], “Maybe I should put the dog in as well” and I knew I had to pump the brakes. [laughs]

But the baby actually [is the daughter of] a couple that works at the restaurant [my husband] owns and Mabel is like the most chill, cool, laid-back baby. I asked her mother if she would consider it and I just knew that when we were doing the schedule, the only thing that mattered was the baby’s schedule, so I said, “We’ll shoot around her schedule.” This is a testament to Yuta Yamaguchi, my [cinematographer] — we just sat and talked about how we could get the baby in and out as quickly as possible. Usually, that meant getting her in at the beginning of the day and shooting her in a wide and then doing a closeup and that was it. One and done. And [Mabel] was amazing. The only time she cried was when we were doing the scene with the barista, which was actually the last day of shooting, and it was later on in the day, so she was tired. Paul Soileau, [who played] the barista, actually started singing a song called “Mabel” that he made up on the spot for her and she got completely calm and quiet. That’s when we grabbed the shots of her in the coffee shop was he’s singing and as soon as he stopped, she started screaming. As soon as that happened, I’m like, “We’re done! We’re good! We have our shot.”

Then we had the baby music scene, which is also because of my producer Bettina, who has a two-year-old now. Originally, I thought it should be this thing they have in Los Angeles, where it’s a Mommy and Me Crossfit workout in the park thing where you basically run around with your stroller and someone yells at you to do push-ups. And I was like, “That’s great. We’ll just do a couple women in yoga outfits with strollers and it’ll be easy because we don’t need babies in the strollers.” And Bettina was like, “Oh no, no, no. You want a music class? I can give you a music class. I go to a music class every week. We’ll just have the music class and we’ll shoot it.” That was 100 percent my producer being amazing because I was trying to avoid putting more babies on set, we actually did the opposite. But then when we shot that scene, it was like baby “Lord of the Flies.” We got them all in a room and then suddenly there was this like flash flood alert on our phones. We had to shoot with this crazy storm outside, so no one could leave and these children were trapped, singing “Old MacDonald” over and over again. I think they were so confused, like “Mom, what kind of music class is this?” [laughs]

You shoot so much of the film outside, where it looks perfectly sunny. Did the weather cooperate with a lot of the shoot?

It was a nightmare. That was the other thing. I was like, “Cool, you put a baby in this movie and then you went ahead and did another scene with multiple babies and then most of the movie your wrote is all exteriors,” which beyond the fact that the weather is temperamental [in Texas] and could in a moment’s notice, just downpour, the sound can be really problematic. One of the exterior scenes we shot on the street and at a certain point, we were like, “Is a parade of elephants going to come down? Every single type of vehicle drove by us probably three minutes into every scene. We could probably put together another short film with just me and the other actor pausing and staring at each other in silence as a gang of motorcycles drove by or a schoolbus full of screaming children. There also was a point where there was supposed to be torrential downpour because we had to redo the schedule, but thankfully the weather held out. It looks pretty consistent weather-wise, but yeah, note to self, don’t do an entire movie outside.

Anna Margaret Hollyman in "Maude"The house of the parents Teeny babysits for is amazing.

I know. I was so obsessed with the type of architecture that’s very indigenous to Austin, which is very clean and modern. Because there’s a lot of glass, the exterior comes in, so you have this lush green environment coming into these pristine, neutral spaces. The exterior house was actually my mother’s friend’s house and then we cheated it — the interior is with my friend Maya’s house. Once again, it was through the generosity of our friends and family that they allowed us to come into their homes and Austin is a character in the movie.

The nursery has this incredible arrow wallpaper, so when Teeny walks into the room, it’s like a reflection of the anxiety she’s feeling. Was that something you created or there to begin with?

Isn’t that amazing? We actually shot in three houses technically and that’s my producer Bettina’s nursery. I always wanted that to be her nursery and I loved the thing that kept happening naturally, [where] there were these very kind of neutral spaces and these very dynamic prints or patterns kept coming up along with these accents of pink. So we started to play with that, the idea that this trend-driven, post-millennial pink, if there is such a thing, starts to pop up throughout Teeny’s day as she moves through the day and takes on this identity [of a mother]. Maybe it’s a little too on the nose on my end, but [in] the first scene, [the baby’s mother] Priscilla is wearing this neutral pink dress, but that’s the first scene where you can really see this pink color in stark contrast to the black and white. But I was 100 percent dependent on all of my friends’ impeccable taste. I wouldn’t know the first thing about production design and we did a little – my sister did production design – but honestly, it was just as simple as arranging props in certain places and adding a bowl of grapefruits in the background to come through with that leitmotif of the pink. Really, we were just grabbing things as they came.

The baby’s parents are played by Megan Ferguson and Nico Evers-Swindell, who I only learned after the short are a real-life couple. Did they come as a package deal?

I’ve been a big fan of Megan’s for a few years now and my producer Bettina is one of her closest friends, so when she first proposed the idea, I was like, “Oh man, if she would do it, that would be amazing. She would be the perfect Priscilla.” She’s one of the most interesting actresses out there and she has a really unique range in terms of what she can do comedically, but she also has this old Hollywood look to her, so when Bettina said, “Hey, Megan and Nico are two of my best friends. If I could get both of them to come down with their two kids, would you be open to that?” And I was like, “Would I be open to that?!?” They flew down with their two-year-old and three-month-old and I feel so lucky that they decided to do it because they just are already, visually, as a couple one of the most attractive couples I’ve ever met and it was important to me that Priscilla [has an] enviable career, but that her partner is enviable as well, but now that I have a child of my own, I really don’t feel that I expressed enough gratitude towards them because oh my God, it is hard [enough] traveling with one child, but to travel with two and then when you both are acting in a project, I’m incredibly impressed that they decided to do it. I plan on buying them many, many drinks at Sundance to thank them.

Megan Ferguson in "Maude"It was funny because the last place I saw Megan was in “The Fundamentals of Caring,” in which her character was pregnant, so I thought this could’ve been a stealth sequel – to see what happened after the baby was born.

Yeah, maybe it was actually. [laughs] I don’t know. I wrote [“Maude”] before I got pregnant and I wanted it to be a creative and an intellectual exercise for me, but I also didn’t anticipate that it was going to prepare me a little bit for motherhood. I said this in my Sundance video, but I was very scared about becoming a mother and how it was going to affect my career because so much of what I do is dependent on me being transient. It becomes a little bit more complicated once you have a kid in the picture and when you have a couple like Megan and Nico hopping on a plane with their two kids to do my first movie, I started to go, “Okay, it’s not easy, but they’re doing it.” Then the set itself was helpful in the sense that it was very mother-friendly and I realized, “Oh, I can make this work for me. I’m just going to have to make sets that are a little bit more kid-friendly or mother-centric.” That just meant that sometimes in between takes you have to go use your breast pump. Both of our still photographers, one was five months pregnant and the other one had a seven-month-old strapped to her chest while she was taking pictures and that was really exciting to me.

Meanwhile, I was three months pregnant and in all my years now, I can say confidently, [filmmaking is] not easy, period, but [making “Maude”] made me realize that you can kind of design what type of set you need to have and want to have. You can set the tone. And as I continue on as a director, I thought I can make changes to make [the set] a bit more inclusive for everybody and for women in particular [to be] more comfortable. That’s what I hope. Because I think that definitely needs to happen. Obviously, there’s a whole [bunch of changes happening in the industry right now], but the most valuable thing I think I got out of the whole experience is [realizing] okay, you can be more than one thing. You can define what you need and what you want in order to move forward in your creative life as well as what you need in your personal life. The two aren’t mutually exclusive.

“Maude” premieres at the Sundance Film Festival as part of the Shorts Program 3, playing on January 19th at the Temple Theater at 9 pm in Park City, January 20th at noon at the Broadway 6 in Salt Lake City and at 9:30 pm at the Redstone 1 in Park City, and on January 26th at 1 pm at the Holiday 4 in Park City.