Hustle and Heart: An Interview with Jessi Alexander


I'm so excited to launch a new series on my blog: Hustle and Heart.  Every other week, I'm going to be highlighting people I admire because they have pursued their dreams.  I think it's so important to share real-life stories of people who have followed their passion and created a life for themselves that requires "Hustle and Heart."  The people I'm going to be featuring aren't letting life simply pass them by each day.  They have decided to write their own story, even if the journey isn't always easy getting there.  

I can't think of anyone better to start with then someone in my own family-Josh's cousin-Jessi Alexander.   Let me give y'all a quick back story on how we met.  After Jessi's parents divorced, Jessi and her mom left West Tennessee.  Josh and his family lost touch directly with her over the years (there was no Facebook or email), but they always kept up with what she was doing through Jessi's grandmother.  We all knew she was a talented recording artist, and we had even seen her perform at The Ryman back around 2003.  Fast forward to 2010, and Josh and I were on a date night in East Nashville at Eastland Cafe.  We lived on the west side of town and rarely ventured over to the East-side (if you're reading this and live in Nashville now-it was a LONG time ago...not the current hotspot it is don't judge!)  

We were sitting at the bar waiting on our table to open up, and Jessi and her husband J.R. walked inside.  Here's what's funny-Josh knew exactly who she was from pictures and started waving.  She looked at him with the strangest look.  It was as if she was wondering, "Should I know him from somewhere?"  I told Josh to get up and go re-introduce himself.  After all, their dads are first cousins.  After a quick round of introductions, we ended up chatting for a long time before we went to our own tables.  But before we did, we exchanged numbers and later that week had them our house for dinner.  From that point on, we haven't missed a beat!

Isn't it funny how time can pass and distance can happen, but one circumstance can bring people back together again?  I'm so glad our paths crossed that night, as I gained a "cousin" and friend.  Ironically, we share the same birthday; we love antiquing together, and we both love to travel.  She and I have shared in the joys and struggles of being working moms, and I'm blessed to have her in my life.

Today, I'm excited to share my interview with her for the very first "Hustle and Heart" interview.

Jessi Alexander, Singer/Songwriter, Nashville, Tennessee

Jessi Alexander, Singer/Songwriter, Nashville, Tennessee

In as few words as possible, describe your 2016?

Here are 2...clean slate.

In as few words as possible, how do you hope to describe your 2017?

Enjoy the gravy.

Okay Jess, I'm going to need you to explain that one!

So "enjoy the gravy" is my way of saying it's time to sit back and enjoy what I've been working towards my whole adult life.  I turned 40 a few months ago, and sometimes there's a tendency for there to be a bit of comedown from that milestone.  I have a husband, 3 kids, a great career, and I need to reflect and enjoy everything I've worked towards accomplishing.  

Did you always know you wanted to write music?

I think I always knew I wanted to write music, but I didn't know it was actually a job.  It wasn't until I was living in Murfreesboro that I started hearing words like "publisher."  I knew there were authors/journalists, but I didn't know of anyone that wrote songs as a career.  I had an awakening when I was at MTSU.  I realized that I could write songs for a living!  I had already been writing songs; in fact, I had picked apart songs as a young child and put my own words to them.  I had gotten frustrated reading sheet music, so I started creating my own music by ear.  I actually won a writing contest in the 4th grade.  I think it was a poetry contest.  I also journaled all through my teens and 20s.  If you think about it, journaling isn't a far cry from songwriting.

So your love for music started at an early age.  Do you remember how it started?

I grew up with my dad being an avid record collector and a fan of so many genres of music.  I was an only child-there weren't siblings to keep me entertained.  So, I listened to music.  Records really connected me and my dad, especially after the divorce.  My dad encouraged me.  I actually would get lost in journeys with his albums.  I wasn't just listening to them-I was devouring them-researching them.  Let's say I was listening to Willie Nelson...that would turn into realizing he had written Crazy and then I was on a scavenger hunt for more information.  I think I was probably 6, 7, 8 years old when this started happening.

But my real "transformative moment" with music came when I was around 10 years old.  I lived with my grandmother during the summers in Jackson, Tennessee.  I was kind of a tomboy, but she took me to the Miss Tennessee Pageant (she promised there would be music)!  I will never forget that night I went.  A contestant sang "Sweet Dreams" by Patsy Cline.  It was my first "full-body-stop-you-in-your-tracks-your-life-is-forever-changed" moments.  I know God whispered in my ear that day.  It wasn't the singer, but the actual song that changed my life forever.  I guess my grandmother sensed it because when we got in the car, she took me straight to Walmart to buy Patsy Cline's Greatest Hits.

That moment listening to "Sweet Dreams" ignited me to sing with emotions.  Here's what's so crazy about it being a Patsy Cline song.  Fast forward to my first record label-MCA.  Around 2003-2004, I was a brand new artist at the label and they released a greatest hits record with her songs.  I was able to pick any of her songs I wildest dreams came true!  I also got to honor Patsy at the Country Music Hall of Fame a few years ago at her exhibit.  They asked me to perform, and I was able to meet her daughter that day-talk about coming full circle!

Jessi Alexander, Country Music Hall of Fame, Patsy Cline Exhibit, 2012

Jessi Alexander, Country Music Hall of Fame, Patsy Cline Exhibit, 2012

Did anyone give you advice that still sticks with you?

I think there are 2 kinds of people-people that thrive on slaps on the wrist and people that thrive on pats on the back.  I think I really found "launching off" points from people's doubts.  In this industry, so many people are naysayers and will tell you are crazy "to do this."  I think those moments are when I pushed myself.  I also have had people to give me advice about work ethic.  You have to show up everyday and be present to win.

Do you have a favorite quote?

"Not all that wander are lost."  I love that quote because there have definitely been times that I felt like I was wandering, but it turns out, I was really headed somewhere.  

Most people probably don't know what it's like to be a songwriter everyday.  What's a typical day like for you?

People would be shocked to know how regimented and "normal" it is.  We have offices we go to, and most are on Music Row.  We have a schedule, and lots of days it can be 9-5:00 or 10-6:00.  That part of our day can be very regimented.  I have someone that keeps my calendar and helps with scheduling who I co-write with each day.  

When I show up, I may sit in front of a complete stranger or someone I've written with regularly.  Songwriting is a craft, but it's also based out of inspiration.  Some days you are out of titles...sometimes your cowriters have nothing.  But we've done it so much and so long, we can take nothing and make it into something.  A simple title that would mean nothing to someone, we as songwriters can look at it from a different angle.  It's a dance we are doing-sometimes I lead; sometimes my co-writer leads.  I can ride on someone else's energy, or maybe they run off of mine.  Here's what's crazy-no 2 songs are the same.  For example, "I Drive Your Truck" (Lee Brice recorded) took 3 co-write sessions.  "Damn Country Music" (Tim McGraw recorded) took an hour and a half to write.  I was fired up and in the right place, right time, right people. 

Okay, this might be hard to answer, but what's your favorite song you've ever written?

"Damn Country Music" rang the bell for me. If you boil it down my truest passion-it's economy and simplicity in songwriting.  I like to say a lot with very little words.  I was inspired by Hank Williams, Sr. growing up.  Words that he wrote like "I'm so lonesome I could cry" inspired me.  Simple words and lines, but they say so much.  I feel like in "Damn Country Music" I was able to nail that with every line.  What I do with songwriting is take topics and expose them for what they are.  This song was about having a love/hate relationship with Nashville.  There is heartbreak and rejection daily.  There are tons of "nos."  Yet, every now and again there's a "yes" and that makes it all worth it.  Other songwriters have told me that we nailed it with "Damn Country Music".  Hearing comments like that is when I knew I've done my job.  

It’s the sweetest highs, the lowest lows
It’s needing yes, and hearing no
Just another soul sold
Believe me, I know
— Damn Country Music
Jessi's kids.  One of the twins sporting the kid version-"Dang Country Music."

Jessi's kids.  One of the twins sporting the kid version-"Dang Country Music."

The other song that still is a favorite of mine is "Mine Would Be You" which Blake Shelton recorded.  That song is such a journey.  As songwriters, we tend to attach things to our past or to an experience.  There are so many layers to this song...I incorporated so many things from my life into that song.  I tried to say so much with so little.  

What’s your all-time high...your good as it gets?
— Mine Would Be You
Jessi performing with Blake Shelton

Jessi performing with Blake Shelton

Those are both awesome songs.  Let's talk about a song that was outside the country genre for you and just happens to be one of your powerhouse songs.  I'd love to know more of the backstory behind "The Climb" that Miley Cyrus recorded.

The day that I wrote that song it was written in the 3rd person.  "He can almost see it...that dream he's dreaming."  I think I wrote it in the 3rd person because it was too painful to go there.  It was like self-therapy, yet in the 3rd person.  Very bizarre.  There are times I'll be writing and won't realize it's about me until 1/2 way through it.  I had been an artist for about 5 years and as lots of women do, I found myself comparing myself to other people.  I was doubting myself.  I remember visualizing what it's like to run a race.  But instead of having my eyes forward, I was constantly looking at who was coming up behind me.  I realized that if I'm so worried about everyone else, I'll trip over my shoestring or fall behind in the "race" I'm running.   I became aware that I have to focus on my own goal and cultivate my own dreams.  In writing The Climb, the guy in the song was like the runner image I had in my head.  What's crazy is that people have come up to me and said they've used that song as inspiration in marathons!

When Miley Cyrus picked it for the movie, it had to be rewritten in first person for her to sing it and it make sense.  Immediately, a lightbulb when off, when I sung it.  I realized that song was something I had written for myself.  Everything that I had experienced as an artist was part of that song.  

I can almost see it
That dream I’m dreaming but
There’s a voice inside my head saying,
You’ll never reach it,
Every step I’m taking,
Every move I make feels
Lost with no direction
My faith is shaking but I
Gotta keep trying Gotta keep my head held high
— The Climb

Even after all of these years, I always learn something new from you about your songs.  I had no idea that it had been written in third person.  I love hearing the back story behind these songs.  So, obviously, pursuing your passion has paid off for you!  What would you tell others that are considering following their dreams?  

I think one of the most simple things they could do is put in the small work.  Of course, there's always big work.  But small work means the little things.  If you want to write, get up and write everyday.  It you want to be a chef, cook every single day.  You can do anything you set your mind to do, but be consistent.  I know so many people that have day jobs, a family and still follow their passion.  I had to treat songwriting like it was my job, before I became a true songwriter.  I had to sit down daily and write, call people to get noticed and apply myself.  That same thing would be true of anyone looking to follow their dreams.  

Also, as we've discussed today, don't compare your journey to anyone else's.  That can be the #1 crutch people have and the #1 pitfall they face.  Don't do it!

That's great advice.  It's so hard not to compare yourself to other people, but like you said, it's crucial to not go there!  I know especially with Social Media in our face 24/7, it's hard to not look at other people and compare your journey.  I've heard it said (especially because of Social Media) "Don't compare your journey to someone else's highlight reel."  

I know as an artist you've had the opportunity to meet some amazing people.  You've traveled the world getting to do your craft.  I know this is a hard question, but do you have a favorite memory or a "moment" from your career to date?

You are right-that is so hard.  I do have to say that my "most peak Mt. Rushmore moment" as a singer on a stage was a few years ago when I was in NYC for the Love for Levon Helm benefit concert.  A few artists that were there included: Gregg Allman, John Mayer, Joan Osburn, Dierks Bentley, my husband J.R. Stewart, Ray LaMontagne, Grace Potter, Eric Church, Joe Walsh, Roger Waters, My Morning Jacket, Mavis Staples, John Hiatt, Lucinda Williams, and Bruce Hornsby.  At that time in my life, I do believe it was a true "made it" feeling.  Not made it as far as fame, but all I ever wanted to do my whole life was make a living doing music.  In that moment, it was pure magic.  Dreams realized.

Love for Levon Benefit concert, New York City, 2012

Love for Levon Benefit concert, New York City, 2012

So, one final question for you, how do you juggle your career with being a wife and a mom of 3 under the age of 8?  

Okay, so you and I know it's not easy being a working mom.  There are days when I feel like I spend too much time on my passion and not enough time with my kids, and vice versa.  But, I've had 8 years of practice as a mom, and I've watched my daughter through that time.  She sees me (her mom) loving my job and that's invaluable to me.  All three of my kids see me having passion in my life.  The trade-off is that it's a juggling act.  You will need help, but in the end it's worth it.  It's the whole "air-mask" thing like on a plane.  I have to have my air mask on before I give the air masks to my kids.  For me that air mask is my music.  I have had low points, and not every day is easy.  But I know that God gives us each an individual purpose.  My kids each have their own as well.  Our goal as humans is to fulfill that purpose.

Jessi, thank you so much for being the first "Hustle and Heart" interview.  I'm so inspired by you and your music.  You truly have a gift for songwriting, and I'm so glad you chose to follow that God-given talent!


Jessi Alexander Bio:

Established Singer/Songwriter, Jessi Alexander, is the writer of some of the chart topping hits on country radio.  Alexander has penned 4 #1s including "I Drive Your Truck" recorded by Lee Brice, which won Song of the Year from 2014 CMA Awards, 2014 ACM Awards and 2013 NSAI Awards.  Additional #1s include: Blake Shelton's "Mine Would Be You" and "Drink on It."  Alexander's career skyrocketed with her song "The Climb".  Myley Cyrus recorded the song and it soon became the anthem for her box office hit "The Hannah Montana Movie" and won the 2009 MTV Movie Awards 'Best Song from a Movie'.  

If you want to learn more about Jessi, you can check out her website at:

Her album "Down Home" is incredible.  Check it out on ITunes at:

Down Home, Jessi Alexander

Down Home, Jessi Alexander