We were lucky to catch up with Lindsay Benjamin recently and have shared our conversation below.
Alright, Lindsay thanks for taking the time to share your stories and insights with us today. I’m sure there have been days where the challenges of being an artist or creative force you to think about what it would be like to just have a regular job. When’s the last time you felt that way? Did you have any insights from the experience?
This is such an interesting question because it is not black and white for me. I grew up wishing to be famous by the time I was twenty. While I did have an agent and pursue auditions for film/tv/singing/music and loved it, I still felt I was having an identity crisis. Performing is in my blood. Being creative is in my blood; but I knew there was another side of me wanting to explore and find out where my priorities lay, especially as I got older.
I decided to take the route of a business professional and focus on the 9-5 grind. Having a family has always been incredibly important to me and I thought that is what you needed to do to get that. For a while, it did provide me with a sense of stability and this confidence that I would find the love of my life and have this amazing career as a businesswoman, but it still didn’t fulfill me and I was grasping at straws trying to be this person that everyone else wanted me to be, or what I thought everyone else wanted for me.
In life, there are times when you have to make financial choices that keep a roof over your head, but I know now that I am happier and fulfilled when I have the flexibility and freedom to make choices for myself and where my life is heading through the type of work that leaves me with room to explore multiple unique opportunities. Music and singing will be my forever number one love, but I also enjoy living a life filled with adventure, romance, and the ability to carve a path that is my own. This path is individualistic to me and it could change direction at any time, and I am perfectly fine with that.
I am happy being creative, and I am happy with a regular job because I know things are always in flux. There are choices in life. You can choose the direction you want to head.


Lindsay, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I got into the industry when I was a little girl. My first show was a musical called Mary Poppins when I was six. That is where it all began. For many years I was a big part of my community’s Local Theater productions until I got an agent when I was a teenager. From there on out, I was auditioning for movies, commercials, TV, Modeling, and much more.
I realized that I actually enjoyed just writing and performing music so I started a band and performed throughout Manhattan at legendary venues like Mercury Lounge, Webster Hall, Bitter End, Bowery Electric, and much more. I’ve written many original songs, and have music videos that you can find on youtube, SoundCloud, reverb nation, Spotify, etc.. When I was 22/23 I wrote my very own one-woman cabaret show with 20/30 songs and was able to sell out the venue each night. I am very proud of that show because I wrote and performed it all on my own and learned that I am absolutely capable of anything I set my heart and mind to.
During Covid, I moved to South Florida and was trying to find ways to be creative during a pandemic, so I played with the idea of a podcast and interviewed 20+ artists on my Instagram live about their budding careers. Even though I am incredibly proud of creating a platform for underground artists to have a voice, it also taught me that I had lost my confidence in my own art and it truly motivated me to get back into gear and find my way home again.
Life is bumpy and you can lose your way momentarily, but it’s the art and the world around you that can lead you back again.


Any resources you can share with us that might be helpful to other creatives?
I grew up when social media was just getting started, before it was the monster it is today. I played outside, went to the ice cream shop, and the mall, and called my friends on landlines. I did not have an iPad or phone until I was probably 18 I think. At that time, I don’t think people were using phones or the internet the way it is used today. Facebook had only opened to colleges and I don’t think I even had an Instagram since most of my friends were on myspace or live journal.
The point is, while there are pros and cons to social media, I’m at a point in my life where there are so many oversaturated apps. It is an entire full-time job to build a popular platform for yourself without understanding algorithms and marketing. Gen Z does a great job at going viral because when you are a kid, teenager, or young adult, your mind isn’t thinking about the mortgages, or friends’ weddings, electric bills, or the IRS knocking on your door. They have the time and patience to sit and really learn what you have to do to get noticed online. While I am glad I did not have social media as a kid, I still think it would have been great for building my career, and I think I would have been able to really hone in on my craft virtually.
What do you find most rewarding about being a creative?
For me, it is my therapy, my release. It is incredibly rewarding when I take lyrics or my journal entries and turn them into a story or entire song. It is like a scrapbook of my personal journey and it showcases how far I have come, and how much room I have to grow and build even more.
When I create something, whether it be a song, a podcast, a one-woman show, or a mini-play, the sky is the limit. There is no wall except for the one I build, and with that is the power to knock it down if it gets in my way. It is an incredible feeling knowing that you built the world around you, and it has chapters and lessons and helps put everything into perspective. Not only do your writing and art get better as you go through more life experiences, but you develop unmatched confidence that can be quite impenetrable.
Contact Info:
- Instagram: https://www.instagram.com/_lindsaybenjamin_/?hl=en
- Facebook: https://www.facebook.com/lindsbenj
- Youtube: https://www.youtube.com/watch?v=SUaFMsd_VWs
- Other: https://www.reverbnation.com/lindsaybenjamin

