Rising Star Olivia Raine Atwood On Five Things You Need To Shine In The Entertainment Industry

…Hanging out with your friends always makes you feel good. When you’re stressed and want to shut yourself away to work on a project, take a break and spend time with your friends. You’ll remember those moments more than the stress of the project. In this digital age, it can be hard to disconnect and be present in the real world, but it’s important. Spending time with friends and doing activities in the real world will make you feel better. Last night, a friend invited me to watch the Celtics, and even though I was stressed, I took a break and went. I’m so glad I did. It’s productive to balance work with real-world interactions. Close your computer, put away your phone, and go see your friend. It’s something I’m still working on, but it’s worth it…

I had the pleasure of talking with Olivia Raine Atwood. Olivia is a multi-faceted performer, entrepreneur, and fitness instructor, known for her dynamic presence in comedy, her successful matchmaking business, and her dedication to fitness. Balancing her time between Los Angeles and New York, Atwood has carved a unique niche for herself, earning praise and recognition across various fields.

Born and raised in Boston, Olivia Raine Atwood grew up in a close-knit family with her parents and two siblings. Despite being a shy child, she discovered a transformative love for comedy and performance at a young age. Reflecting on her childhood, Atwood recalls her first role as the back half of a tiger in a second-grade play, a moment that sparked her lifelong passion for the stage.

Atwood pursued her passion through various theater programs and summer camps, eventually studying theater in college. It was here that she met Maggie Seymour, a fellow performer who would become her partner in a two-woman theater company. Their collaboration led to numerous performances and laid the foundation for Atwood’s burgeoning career in comedy.

Olivia’s talent did not go unnoticed. Time Out New York described her as “riotous,” and her comedic duo with Seymour was likened to a “modern-day Lucy and Ethel” by StageBuddy. Atwood’s performances have been lauded by New York Magazine, The Huffington Post, and other notable publications. Her off-Broadway debut came in July 2023 with “Liv, LIVE” at the SoHo Playhouse, followed by “UNDERPREPARED & OVERHYDRATED” in December.

In 2024, Atwood embarked on a tour with her latest one-woman show, “FAKING IT,” which includes stops at the Denver Fringe, Hollywood Fringe, and Edinburgh Fringe Festival. The show, which runs nightly from August 2–26, explores her experiences as an undercover patient in New York City, a job she held for several years.

Beyond her work in comedy, Atwood is the founder of a successful matchmaking company, Liv’s Love Pool. Her company has been featured on NPR, WNYC, and Elite Daily, and it won the 10k Rookie of the Year prize at the IKON Start-Up Awards. Atwood combines her knack for connecting people with her personal experiences, offering private date coaching and matchmaking services.

Atwood’s enthusiasm for fitness is another significant aspect of her life. She teaches classes in both Los Angeles and New York, dedicating numerous hours to helping others achieve their fitness goals. Her journey into fitness began during a low point in her life when she stumbled upon a SoulCycle class, which led her to become an instructor.

Despite her busy schedule, Atwood maintains a balanced approach to life. She emphasizes the importance of enjoying one’s daily activities, advocating for fulfilling “survival jobs” that bring joy rather than stress. Her own switch from waitressing to fitness instruction exemplifies this philosophy.

Atwood’s personal anecdotes reveal her down-to-earth nature and ability to learn from mistakes. From backstage costume mishaps to humorous experiences in waitressing, she reflects on these moments with humility and humor, using them as lessons for herself and others.

Looking ahead, Atwood has several projects in the pipeline, including a book of essays and a podcast titled “Yessays with Liv.” She continues to inspire others with her dedication, creativity, and relentless pursuit of her passions. Her influence extends beyond the stage and into the lives of those she helps through matchmaking and fitness.

Olivia Raine Atwood’s story is one of resilience, creativity, and multifaceted talent. From her early days in Boston to her current status as a touring performer and successful entrepreneur, Atwood embodies the spirit of determination and passion. Her journey serves as an inspiration to many, proving that with dedication and a love for one’s craft, anything is possible.

Olivia, it’s a delight to meet you. Before you dive in deep, our readers would love to learn about your personal origin story. Can you share this story of your childhood and how you grew up?

Olivia: Wow. My personal origin story. I love that. I’m from Boston. I grew up with my family, super close to my mom and dad. I have two siblings. I’m definitely the most organized and responsible. Don’t tell them I said that.

I’ve always loved comedy and making people laugh. I was a really shy kid growing up, but when I got on stage, everything changed. I would become someone different, which I know is such a classic story for a shy kid. That was definitely the origin of it all. I think my first role was the back half of a tiger in the second grade, like the tail and hind legs.

It’s amazing. So let’s hear the next part of the story. What led you to this successful career as an actress and doing other great stuff?

Olivia: Yeah, definitely. My family is super supportive, and my parents have always encouraged me to follow my dreams. There have been many times in my life when I thought about doing something else, not because I necessarily wanted to, but because I felt like it would be more stable or less stressful. But my parents always insisted that comedy is what I really want to do. And they’re right.

I’ve always stayed the course. I did every summer program possible growing up that was theater-related — camps, theater at sleepaway camp, everything. In college, I studied theater and always participated in programs. It’s been one thing after another until eventually, I booked my first show in college with my good friend Maggie Seymour. From there, it’s just been a snowball effect.

It’s amazing. So you probably have some amazing stories from different experiences, different sets, different productions. Maybe this is hard to boil down, but can you share with our readers one or two of your favorite stories from behind the scenes of a project or just something that typifies your life as an actress?

Olivia: Sure. So, I’ve worked backstage at a lot of different productions. In the theater world, you often take any job to be near the action. You’re not always going to be on stage, but you want to be involved. For a long time, I was a star dresser, which means I would stand just offstage during major productions, ready for quick costume changes. Sometimes you have 30 seconds to completely change an actor’s outfit.

One memorable occasion was during a production of “Seared” at MCC in New York City, one of my favorite productions ever. I loved the cast, loved the crew, and Teresa Rebeck is one of my favorite playwrights and novelists. I was so excited to be working on this show. An actor and my good friend, Dave Mason, came offstage, and I had a really quick change to do. I don’t know what I did, but it was so wrong. We had like 20 seconds, and Dave went back onstage with his shirt on sideways and backwards, with a sleeve flopping in the wind, his arm not through the sleeve. The shirt was sideways, backwards, off, flopping, and they had to literally hold the show so Dave could fix his shirt and then continue.

I was standing in the wings thinking, “That was fully my fault, 100% my fault.” For the rest of the show, Dave and I would always joke around, asking, “Will I be able to do sleeves? Can I do sleeves? We don’t know if I can do sleeves.” So, lots of stuff like that. You’re not always succeeding, but you’re always trying your best.

It’s great. So, you know, I always wondered about that. How they switch costumes so quickly. I never realized how much pressure that is.

Olivia: Whenever you go see a show, my favorite thing to do now is go through the playbill and look for the dressers. I check to see how many dressers there are and if people have specific dressers. Sometimes a show will have one dresser, sometimes ten. I’m always paying attention to those costume changes now because I know what’s happening backstage. When there’s a really quick change, I’m like, “Way to go, that was incredible.” It’s just a fun thing to start paying attention to.

It’s been said that sometimes our mistakes can be our greatest teachers. Can you share a story of a humorous mistake you made when you were first starting and the lesson you learned from it, aside from avoiding wardrobe malfunctions?

Olivia: Yeah, wardrobe malfunctions are a big one. I completely agree with you, though. I think mistakes can really inspire or push you forward.

Here’s one that’s not from acting per se. When I was starting out as an actress, I was also a waitress, which is a classic trajectory. I wasn’t a waitress for very long because I quickly realized waiting tables was not for me. On one memorable occasion — and I will not say the name of the restaurant because I do not want them to remember that I worked there — I mixed up someone’s leftovers with a to-go order. I sent a half-eaten burger out with the Uber Eats guy. This keeps me up at night because there are a lot of foods that could arrive home half-eaten and you wouldn’t necessarily know, like spaghetti, risotto, possibly even a hummus platter. But a burger? Half a burger? That’s the most visually traumatic thing you could ever get.

I share this story because, first, it’s horrible, absolutely horrible. But more importantly, it’s a lesson for anyone pursuing a creative field. Everyone always talks about the survival job that you need to have. I became a waitress, as many actors do, as a survival job. But I realized I was terrible at it and it wasn’t making me happy at all. Your survival job is what you are doing 99% of the time. You might get a break, a show, or book a commercial, but most of the time, you are waking up and going to your burger restaurant or whatever.

I realized at this restaurant that my survival job needed to be more fulfilling. For some people, that is waiting tables, and I’m not knocking that. But for me, it wasn’t. I became a fitness instructor, which is a much better fit for me. I’m much happier teaching fitness every day. It was a long process of working at the desk and climbing the ladder, but it’s what you’re doing 99% of the time, so you want to be happy and fulfilled. I really dislike the phrase “survival job” because it’s just your job. I don’t want to be surviving; I want to be having a good time. That’s what I’m doing every day. And I’m no longer mixing up half-eaten burgers with to-go orders. We don’t do that anymore. So, I think that is a really big lesson that I learned.

You’re an amazing storyteller. It’s hard to imagine that you’re a shy person. So I’m wondering, do you think that you’re not shy anymore because you’re acting? Or do you think you’re really just acting?

Olivia: That’s another great question. I think it comes and goes in waves. The really shy girl from high school, who some people might have thought was a mime because I never said anything at all, is still inside me. It comes out sometimes.

I was at a bunch of festivals this week. At one show, the actress asked if there were any other performers in the audience who wanted to pitch their show, to stand up and pitch. I was there with my boyfriend and my parents, and they all looked at me like, “Go pitch your show.” But I was like, “No, no, no, I’m not going to do it.” Everyone afterward was like, “Liv, why do you do that?”

I’m shy and self-conscious. Even though I perform and seem pretty extroverted in my daily life, sometimes I still feel like, “Oh no, I don’t want to.” So, I think that shyness is still very much there, and I sometimes have to work to overcome it. I have to force myself to talk to other artists, be social, and do all of that.

I think I’m really a mix of extrovert and introvert. I’m more of an extrovert these days with my career and what I do, but the shyness still comes out sometimes. It surprises me.

Amazing. We love stories where somebody who’s a little further ahead opens a door, creates an opportunity for somebody. And that changes their life trajectory, changes their career. Do you have any stories like that where somebody went out of their way to do a kindness when they didn’t have to? And that really changed your life?

Olivia: Yeah, totally. I have a few that come to mind.

The first is Ryan J. Haddad, an actor in New York City and a very good friend. I was at a dinner party he attended, and I was just telling a story. Ryan, a talented actor and storyteller, interrupted me to say, “You’re really, really good at telling stories. You need to be doing this.” At the time, I wasn’t performing much, coming off of COVID, feeling lost, and going through heartbreak. His encouragement reminded me of my passion and talent for storytelling, which I had forgotten. That moment switched something in my head, and it kicked off the following three years of my touring a storytelling show. Big props to him for putting me back on the path.

The second story involves my college friend and performing partner, Maggie Seymour. We had one improv class together, and she asked if I wanted to be a part of her show. That small stroke of luck led to us forming a two-woman theater company and touring the country with a show we wrote together.

The last one is about my good friend Leah Mirani, whom I met while working at a theater festival. When there was a drop of a star dresser on the show “Seared,” she reached out and asked if I wanted to try. It was another way to get closer to the stage and remind myself of my passion.

These big breaks were really small moments of kindness, encouragement, or someone taking a chance on me. I’ve had so many of those moments, whether someone reminded me of my passion or offered me an opportunity to stay in this world.

It’s amazing. Beautiful stories. Perfect. Okay, so you have so many exciting things going on. Please share with us, share with the readers what you’re working on now, what you hope to be working on in the future. Tell us why we all have to come to watch your show.

Olivia: So, I’m in the middle of a tour right now. My show is called “Olivia Raine Atwood: Faking It.” I had to start using my middle name because there’s a woman on Love Island UK named Olivia Attwood. We’re different people, so I’m Olivia Raine Atwood now, which is very cool.

Interviewer: When I put your name in Google, it suggests that I meant Atwood with two T’s. I was almost certain I was interviewing her. Hopefully, this article will help to address the search results.

Olivia: I’m secretly hoping to meet her someday because I’m also a matchmaker, which we’ll get into. There’s further overlap — she was on a love TV show, and I’m a matchmaker. She has a podcast and does comedy, but different from mine. I would love to meet her someday and be like, “Man, I get fan mail for you all the time. Maybe we should be friends.” There’s actually a section in my show where I compare the two of us. If you’re interested in hearing how I compare us, come to my show. So, it’s Olivia Raine Atwood these days.

My show is on tour right now. It’s about my experiences as an undercover patient in New York City, testing and evaluating the hospital systems and doctors. Yes, it’s 100% true. It’s a real job I had in New York for many years. When I was doing the job, I had no idea it would eventually inspire an entire show. But after doing shows for the last couple of years, this particular story was the one people really responded to. It was clear I needed to make it the arc of a larger show.

The show weaves in a lot of other stories, including that burger story I mentioned earlier. There are lots of little nuggets throughout the larger quilt of the show. It’s currently on tour, with two more shows in Los Angeles, then heading to New York for a couple of shows, and finally, I’ll be at the Edinburgh Fringe in August, performing 25 times in a row.

Aside from that, I’m also a matchmaker. I still do matchmaking and private date coaching through my company, Liv’s Love Pool, working with many private clients. I’m also still teaching fitness, with classes in Los Angeles and New York. Lastly, I’m getting ready to launch my podcast and finish my book of essays. So, if anyone out there thinks I should have a book, it’s coming soon — I just need someone to publish it. That’s a lot of irons in the fire. I don’t know how I balance all that.

That’s amazing. So this is our signature question that we ask in all of our interviews. You’ve been blessed with a lot of success now. Looking back to when you first started, can you share five things you wish somebody told you when you first started? Five things that you know now, but you wish somebody told you when you first started and why?

Olivia: Sure. Five things that I know now.

1. Your survival job is the thing that you’re doing every single day. Make sure it’s something you enjoy or that gives you benefits. For me, teaching fitness is perfect because I love it and I get free gym memberships and classes. If you love clothes, maybe work in retail. Just because the classic job is waiting tables doesn’t mean that has to be your survival job. It’s the job you do every day, so make sure it makes you happy. You want your audition or booked role to feel like the cherry on top of an already good life. If you walk into an audition thinking, “I need this job to make my life good,” it’s a lot of pressure. Instead, think, “My life is good, and getting this job would be the cherry on top.” That mental switch was huge for me.

2. Make your bed in the morning. Let that be the first thing you do. It feels really good and gives you a sense of accomplishment. There’s nothing better than coming home after a long day to a nicely made bed. It took me way too long to learn this, but now my bed is always impeccably made. I even tell my boyfriend to be better about it.

3. Don’t sweat the small stuff. This might sound cliché, but it’s true. Something that stresses you out now will likely be forgotten in a few weeks. Put things in perspective. I was once so stressed about an audition because it conflicted with my boyfriend’s cousin’s wedding. I almost didn’t go to the callback because of it. Looking back, I wasted so much time worrying. If I had booked it, we would have figured it out. Spending too much time and mental space stressing about “what ifs” is not productive. Things usually work themselves out, so try to take deep breaths and trust that it will be okay.

4. Exercise. I hated exercise for the longest time, but it actually feels good. I’m not saying you have to be a fitness fanatic, but moving your body is great. Taking a walk can do wonders for your mental health. I discovered this by accident when I walked into a SoulCycle class during a low point in my life. It changed everything for me. Now, I teach fitness and love it. Exercise isn’t just about looking good; it’s about feeling good mentally and physically. I wish I had known that sooner.

5. Hanging out with your friends always makes you feel good. When you’re stressed and want to shut yourself away to work on a project, take a break and spend time with your friends. You’ll remember those moments more than the stress of the project. In this digital age, it can be hard to disconnect and be present in the real world, but it’s important. Spending time with friends and doing activities in the real world will make you feel better. Last night, a friend invited me to watch the Celtics, and even though I was stressed, I took a break and went. I’m so glad I did. It’s productive to balance work with real-world interactions. Close your computer, put away your phone, and go see your friend. It’s something I’m still working on, but it’s worth it.

Amazing answer. This is our aspirational question. So Olivia, because of the great work that you’ve done and the platform that you’ve built, you’re a person of enormous influence. If you could spread an idea or inspire a movement that would bring the most amount of good to the most people, what would that be?

Olivia: Down with social media. Not completely, but with time limits, like an hour a day. And I am so bad at this. It feels stupid to say it out loud because I’m not good at it. I think I’m okay, but I could be way, way better. I wish, in my aspirational worldview, that Instagram is a tool. I can go on Instagram to post about selling tickets for my show, you know, as a business tool. But scrolling endlessly on Instagram is terrible for me.

I have a bit of imposter syndrome and a competitive streak, and I compare myself to others all the time. I wouldn’t be doing that if it weren’t for Instagram. When I see someone’s show is selling out, or someone is engaged, or just booked a tour, these are not people I know. These aren’t friends of mine, so why am I feeling less than by looking at that? It’s so unhealthy. We all spend hours scrolling, and instead, we should just go outside, do things, go for a walk. I wish we were doing that more.

I think it would bring us back together as a society. We’d be making eye contact with people more in the real world, getting back to the roots of doing stuff that’s healthy and good, not just for the internet or photo opportunities. It’s something I’m really still working on. Even limiting it to an hour a day would be good. For a little while, I only went on Instagram on Wednesdays, and that felt so healthy. I’d check it on Wednesdays, do what I needed to do, and then wait a week. That was amazing.

I don’t think that’s realistic right now because of the tour and how much I have to be engaged on Instagram, but if I could limit it to an hour a day and think of it as a business thing, that would be good. Yeah, down with social media is my social movement. Less social media for everyone.

I wonder if you could hire a VA to respond or handle that stuff for you.

Olivia: Exactly. I know there are social media managers out there, and I think, yeah, maybe. But then I feel bad for them. They don’t want to be on their phone all day either. Less social media for everyone, less.

That’s great, amazing. So how can our readers purchase tickets to your shows? How can they continue to follow your work? How can they support your work in any possible way?

Olivia: Incredible. The two main channels are my Instagram, @liv.thedream. I’ll be posting tour updates and other stuff there, though hopefully not up to the minute because I’m trying to be on Instagram less. But updates will be there. Also, my website is liv-thedream.com, which is continually updated with ticket sales and the latest info.

I’m launching a podcast soon called Yessays with Liv. I read essays that I’ve written out loud and they make you say yes. And hopefully, my book will be finished and starting to get out there into the world soon as well. But yeah, Instagram and my website are definitely the go-tos.

Okay, great. Olivia, it’s so nice to meet you. It’s really been a joy. I wish you continued success and blessings. I know you’re a rising star, and you’re going to be a superstar one day. I hope even when you’re a superstar, you’ll do another interview with me.

Olivia: Absolutely. I will, 100%. You can count on that, you can count on that.

Amazing.