Meet Stephanie Windland | Singer, Actor, Director, host, Creative figuring it out as she goes

We had the good fortune of connecting with Stephanie Windland and we’ve shared our conversation below.

Hi Stephanie, we’d love to hear about how you approach risk and risk-taking.
My college graduation cap says “Do the things you’re scared of” in colorful stickers. That was my favorite quote for years. The idea of leaving your comfort zone and facing life head on was so appealing to me. I wasn’t necessarily great at it though. In many ways I did take risks but I’m also a master of justifying why I’m not ready for something. I’ve let opportunities pass me by and have kept myself stuck for years out of fear of disappointing people. The thing about risk is that you really have to find the balance in being calculated and brave. It’s good to sit down and think about the consequences, however, we so often focus on what could go wrong and completely forget to focus on what could go right which I honestly feel is more important. When things go wrong, you learn from them. There’s not much to learn from never trying in the first place. When I finally got tired of feeling stagnant for so long I decided to move across the country. I had multiple jobs that I really enjoyed (Tour guide, karaoke host, etc.) I was obsessed with my apartment and my family and friends are all there. So the decision to leave all of that behind was a big one. I had to ask myself my go to question when it comes to risk taking. “Are you making this decision out of fear?”. If I stayed in NY, that answer was yes. So now here I am in LA and it has been one of the most difficult and most rewarding decisions i’ve made in my life. I’ve learned more about myself than I have in years. I’ve felt at my weakest, stronger than I knew possible, smart, naive, brave, creative, lame, exciting, lost, and just really really proud of myself. Every lesson, good or bad, has been worth it. The misconception about the earlier quote is that sometimes facing your fear doesn’t necessarily take that fear away and that’s really ok. So my new favorite quote is “Stay scared. Do it anyway”.

Alright, so let’s move onto what keeps you busy professionally?
I would currently describe myself as “a creative figuring out her chosen medium”. Singing was my first love, then I studied Musical Theater in both high school and college. I did the whole NYC grind where you wake up at 3 AM to get your name on a list just to sing 32 bars if you’re lucky and I was fortunate enough to book a few jobs after college. However, something about the audition environment never felt right for me. I had a sense that I’d need to take a different route if I wanted to “make it”. So I began improv and performed on a few indie teams, produced and starred in a web series for two years, booked a few commercials, and continued with acting and vocal lessons. During Covid I played around with writing and directing and ended up directing a few music videos and a SAG short film which I really enjoyed. Before moving to LA I tried stand-up a few times which was terrifying but wonderful. Then timing made it’s decision for me when I moved out to LA to do film and TV and the SAG strike began immediately. All that is to say that i’m still working on finding my voice and how I’d like to use it. The entertainment industry has a way of making you feel like you either get famous or fail. As if making a pivot in your career can’t be for the sole reason of deciding you want something different, as opposed to this idea of “giving up”. So after years of doing musical theater and wanting to be an actor, I had a difficult time letting myself explore other options. Now I’m having fun with it. A recent realization I’ve had is that I’m a good leader. I like to help people feel comfortable and seen in any space which is one of the reasons I love directing so much. I’d really like to make films that combine my need for humor and my love for humans and all their idiosyncrasies. I want people to feel less alone and be able to laugh at themselves. We’re all lost in some way and trying to figure it out as we go. If I can make sense of that for others than I can make sense of it for me too.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Well I moved here a year and half ago and I’m still figuring out the city, so this will probably be the #1 most basic guide to LA. I also hate planning itineraries for other people because I get too stressed out about it being “perfect”. That being said, my go to places are Mama Shelter because the food is incredible, the drinks are amazing and you get a really great view of the Hollywood sign. The farmers market in Hollywood is great because most of my friends are from the East Coast, so being able to have an outdoor market year-round is not something that we see often. I also typically do a beach day – Malibu first comes to mind. The beaches feel clean and you can also fit in a hike in the morning with a really nice view.

I live in Burbank so I like to take people to Magnolia Ave to try Portos and explore the different vintage shops. Truthfully though my favorite thing to do is drive my friends through the hills of Los Angeles to see the views of the city. There’s this one moment when you’re on the 10 freeway driving from Santa Monica to Burbank and the entire city glitters before you. I like to play City of Stars from La La land just as we hit that spot. If I get an eye roll from my friends as I do it…even better.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I dedicate my shoutout and everything I do to my family and friends. They see me in ways that I can’t always see for myself. They show up consistently, they support my art and trust my decisions and just let me know that I am always loved. They are the sole reason I can take risks because when all else fails, I know they’ll be there to make me laugh REALLY hard about it.

Website: https://Stephaniewindland.com

Instagram: https://www.instagram.com/swindland/?hl=en

Image Credits
Alex Dreschke