Dreamer Spotlight: Annie Bosko

Today, we're spotlighting, dreamer Annie Bosko. When I think of this blog, and why I started it, it's to share stories like Annie's. Annie has


pursued her dream with diligence, passion, and has refused to give up. I've been great friends with Annie's sister Tina for a few years, and Tina always told me I needed to meet Annie. About a year ago, we finally connected at Tina's birthday, and we clicked so quickly talking about dream chasing, and the reality of really taking that leap. 

Annie is a singer songwriter living in Nashville, and she just recently released her latest hit,

Crooked Halo


 Annie has shared the stage with Adele, Josh Groban, Dierks Bentley, The Fray, and many other talented artists. Crooked Halo is quickly garnering quite a lot of attention. The Highway has selected

Crooked Halo as one of their Highway finds

, and Seahawks coach,

Pete Carroll

and Steelers player, 

Troy Polamalu

 have also tweeted how much of a fan they are of the new hit.  

When you were little what did you what to be? 

"When I was little I absolutely knew I wanted to be a singer. My mom claims I sang before I spoke as a toddler in my crib. My first singing job was when I was 13 years old with Disney for a soundtrack. This was the "aha" moment of affirmation that I could potentially make singing my career. When I was 15, I started hostessing and singing "Happy Birthday" in Itailan at Macaroni Grill which taught me about the service industry

(and eating giant loaves of bread that taste AMAZING fresh out of the oven, drenched in olive oil).

I am a people person and that's important in my career because fans want engagement. I love shaking hands, giving people hugs and signing cd's after a show. I started singing commercial jingles and demos for songwriters in high school which taught me how to sing in the studio and find harmony parts. It also taught me about the structure of a song.

I worked at restaurants and cleaned houses for a while which I hated (if you saw my apartment you'd die laughing... messiness is my weakness), but, it was cash in my pocket and I was stuck in a bad deal for a year. Perhaps sometimes you have to do something you hate to eventually love what you do. It makes you appreciate it.

I sang background vocals for some acts, including Adele on a special occasion. This showed me that I truly desire the spotlight, however, I'm fortunate to have honed my chops with great opportunities. I can sing all my own background vocals and power through a show. "Use it or lose it." I have worked LOTS of odd jobs. I guess that's what you sign up for as a musician. I signed my first publishing deal a few years ago which was nice because it was a set salary and I wrote songs for a living. This allowed me to focus and zone in on my "voice" as a songwriter." 

Annie as the Little Engine That Could 

How did Crooked Halo come about? How long did the process take from writing to recording? 

"I was at my little sister's college graduation and I heard someone say, "Tina, she's our little angel with a crooked halo." My sister is pretty much an angel with a straightened halo, however, she's a lot of fun too. Good girls can still have fun! The song is about a female breaking the mold and doing the unexpected. I came in the room with the the idea, my co-writers built a loop (the stomp, clap) and the song kind of wrote itself. The best songs usually don't take long and kind of "write themselves." It's all about capturing the magic of the moment and running with it. We made a work tape of the song right after writing it which happens to be available on my website as a free download if you sign up for my newsletter. It was originally in first person and we changed it to third which makes it way more identifiable. For the finished track, we built it from the ground up and tracked a few live instruments later. It didn't take very long to record. I just had to make sure my "attitude" switch was turned on!"  

Walk us through you going to USC (University of Southern California), and how the shift really happened into pursuing music full time.

"I lasted for about two years at USC. It is an amazing school and my family really wanted me to go. If it were up to me, I probably never would have attended college because I am so career driven and the music industry does't call for a degree. I'm happy I did go because of the incredible friendships and contacts I made. I was working as a singer for hire while in college and pursuing my music which was really tough. I got offered a job in Europe and that was the straw that broke the camels back. I took a leave of absence and then moved to Nashville. I have no regrets, but, I wouldn't be surprised if I completed my degree one day." 

Photo By Betsy Newman

Who has been your biggest cheerleader?

"My parents, siblings and entire family have been my biggest cheerleaders. They are the ones, along with a few friends, who will walk through the trenches with you and show up to watch you play for a bunch of loud, obnoxious drunk people in a parking lot."   

What's been the biggest surprise for you during your career, or what has happened that you didn't expect? 

"I honestly didn't think it would take so long to get things up-and-running. I remember moving to Nashville and someone telling me it was a 10 year town. I didn't expect to have so many obstacles, but, I also didn't expect to have so many blessings. People that I used to geek out over are now peers and collaborators." 

Obstacles you've experienced along the way? How have you dealt or overcome them?

"My first major obstacle was after my short run on American Idol four years ago. My ongoing joke is, "I made it to American.. not quite Idol." It was a very tumultuous and vague process. I see judges on singing reality shows reaping far more exposure and benefits than the contestants. I could always change my mind if I were on a different show at a different time in my life, however, with American Idol there were numerous incidents that led me to believe I wasn't being groomed as a token winner. I was stuck in a contract that didn't allow me to play shows or sign a publishing deal for almost a year after which defeats the purpose because you only have a small window after a show like that to capitalize on the exposure. I got really angry and channeled it all into my songwriting. It's never been enough for me to be just a "singer". My goal now more than ever is to prove I'm an "artist". 

Knowing what you know now, what would you tell your 21 year old self?

"I would tell my 21 year old self to chill out, enjoy the ride and don't take things too seriously. Also, don't make decisions out of fear or be too concerned about what other people are doing." 

Where did you film Crooked Halo, such a cool video really showcasing so much. How did the idea come to you?

"We shot the "Crooked Halo" music video up the coast of California, from Venice Beach to Paso Robles. I grew up a tomboy in California. I was always climbing trees, playing outside, surfing, riding horses, riding bikes with the boys in the neighborhood. I remember one time they were jumping off a ramp on their bikes and I wanted to prove I could as well. I ended up scraping the entire side of my face. I wanted to feature groundbreaking females that could hold their own in a man's world with grace and beauty (which I think dudes totally dig). I put up a Facebook post which led me to finding a video of professional surfer, Frankie Harrer, surfing in Teahupoo, Tahiti (one of the deadliest surf spots in the world). I found Alana Smith, professional skateboarder, with the help of a friend. She holds a Guinness World Record for being the youngest X Games Medalist. I recruited the beautiful and fierce motorcyclist, Karen Gorham, at Neptune's Net on PCH. Jaye Ganibi is a real authentic cowgirl and sweet friend of mine. Lastly, I wanted to showcase the innocence and free spirit of a little girl to go with the line, "Still barefoot, wide-eyed running through the field. Tell her that she won't and she sure will." My little niece, Kate Boskovich, was perfect for it because she is so sweet, gorgeous and authentically herself."

Even though Sirius XM's station The Highway believes Crooked Halo is a "Highway Find," you've really been at this for awhile! What advice would you give to young singers loosing hope?

"I first picked up a microphone 23 years ago, got my first job in the music industry 15 years ago and have been in Nashville for 8 1/2 years. Everyone has always looked at me and said, "I can't BELIEVE you haven't made it yet." LOL! There's always going to be someone who's dad has more money than you or is related to a celebrity. You just have to stay the course and "run your own race." Pray, meditate, daydream and have a vision so clear no one can tell you anything different." 

Favorite part of you job?

"My favorite part about my job is when someone messages me or comes up to me after a show and tells me a song of mine has touched their life. It's standing on stage in front of tons of cheering people, but, also shows like the one I played a few nights back at a halfway home. Seeing people uncontrollably cry or jump up out of their seat. Bringing hope to the human spirit."

Who would be a dream collaboration for you?

"That's tough. Steven Tyler, Butch Walker, Eric Church, Dierks Bentley, Imagine Dragons etc…" 

Quotes to keep you going?

"Now faith is confidence in what he hope for and assurance about what we do not see." Hebrews 11:1

"Actions breeds reaction"

"It is not the critic who counts…." by Theodore Roosevelt 

"Luck is when preparation meets opportunity."

What have you given up to pursue this dream, to give your dream life?

"I have given up a lot to pursue my dream. I moved away from my entire family, have had failed relationships and missed a lot of weddings, dinners etc. It's competitive and very time demanding." 

One thing you wish people knew about you or wish they knew about Crooked Halo would be....

"People that don't know me don't realize how hard I've worked to get to this point. They don't know about the sleepless nights, the 10,000 hours spent developing my craft, the doors that slammed in my face, the deals that were promised to me and fell through at the last minute. You endure a lot of emotional turmoil being in such a crazy business, however, it's all worth it for the amazing blessings that come too."

Thank you Annie for sharing a slice of your story with If You Can Dream It Do It!

Follow Annie on her journey








Watch Crooked Halo's Music Video :


So excited for Annie, and I know in the short time of knowing her, she's already taught me the value of persistence, patience, and endurance. 



Lindsey CaldwellMUSICComment