Jessi Alexander moved to Nashville in 1999 hoping to make it as a musician. She found some early success but then her record deal ended, her mother passed away, and she faced many disappointments. In 2007, while in San Francisco, she had an epiphany to stop pressuring herself to succeed as an artist and just focus on songwriting. This change in perspective led her to greater success, including writing the song "The Climb" for Miley Cyrus and receiving two Grammy nominations. Although one nomination was later rescinded, Alexander has continued to find fulfillment through her songwriting and family.

1. 42 43Rolling Stone Rolling StoneMay 29, 2014 May 29, 2014
Seven years ago, Jessi Alexander
failed and flailed. She’d moved to
Nashville in 1999 as a 21-year-old,
arriving in a Nissan Sentra, hoping to
make a living making music. Then came work as a
backup singer, support from celebrated songwriters
and industry heavyweights and a major label
record deal.
And then came the part where
the record deal went away and
her mother died of cancer and
disappointments stacked
upon disappointments.
That was the part where
the people who’d been
certain that Alexander
would be the new
century’s Emmylou
Harris shook their heads
in disappointment that
she wasn’t.
In 2014, Alexander
is not the new century’s
Emmylou Harris. But she’s
nominated for two best country song
trophies at today’s 56th Annual Grammy Awards;
she co-wrote the Country Music Association’s top
country song of 2013, “I Drive Your Truck.” She’s
among the hottest writers on Music Row, with songs
recorded by a stylistically diverse, ever-expanding
group of notables that includes Blake Shelton,
Celine Dion and Miley Cyrus. And she radiates
gratitude and fulfillment. The trick was learning
to give up.
“I remember the minute it happened,” she says,
seated at a restaurant table, the day before flying to
Mexico to write songs with friends Miranda Lambert
and Ashley Monroe.
“I was on a sidewalk in San Francisco, thinking,
‘What is causing this turmoil in my heart and soul?’
It kept coming back to the pressure of being an
artist. I finally asked myself, ‘What would happen if
you weren’t?’ and the clouds parted. I realized I was
trying to get into a party where I really didn’t want
to be.”
For Alexander it meant clutching and grabbing
for every opportunity and flying across the
country to meet radio programmers who
smiled and cooed and had no intention
of playing her only released
single, “Honeysuckle Sweet.”
It meant branding and selling,
wardrobe and angles and advice.
It meant living in a world of
indistinct possibility, sacrificing
endless todays for hypothetical
tomorrows.
And so, in 2007, on a gray San
Francisco day that turned suddenly
cloudless, Alexander gave up.
She decided to write songs every
day, to focus on present moments rather
than future fictions. That November, she went to
the BMI Country Awards, watched friends collecting
the trinkets she’d failed to acquire, and thought to
herself real joys are found in doing, creating
and working.
When she related that thought to co-writer Jon
Mabe, they wrote a song that found its way to the
innocent and shining, pre-twerk Miley Cyrus, whose
version of “The Climb” topped the Billboard adult
contemporary chart for 15 weeks, won best song
from a movie at the 2009 MTV Awards, garnered
some mighty royalty checks and received a
Grammy nomination.
The Grammy thing was cause for the people who
Jessi Alexander gives up and finds success
figured Alexander would be the
new century’s Emmylou Harris to
send congratulations, flowers
and Champagne.
And then, after a night of
celebration, Alexander was told
that her Grammy nomination
in the best song written for a
motion picture category was being
pulled, because “The Climb” was
inspired by personal experience
and not specifically by “Hannah
Montana: The Movie.” She’d
been ratified and commended, and
now she was officially un-ratified
and un-commended.
“That was probably the lowest
point of my career,” she says. “I
thought that was probably
going to be my
only Grammy nomination, and it
was a heartbreak.”
People gripe about the
Grammys. They say that the
voting process is flawed, that the
best music doesn’t triumph. But
to musicians, the award remains
coveted, legitimate and respected.
The nomination made
Alexander feel valued. Having
that taken away did not. Nothing
to do but give up, something
she’d learned to do on a San
Francisco sidewalk. And so
Grammy non-nominated,
non-recording artist Jessi
Alexander went back to
work, writing songs.
Alexander is married
to Jon Randall Stewart, the
hyper-talented musician,
producer and songwriter
who co-wrote another CMA
best song winner,
“Whiskey Lullaby.”
Together, Alexander and
Stewart have a home that
rings with music and a fine
and soulful band called
18 South that plays
Nashville clubs.
And a 5-year-old daughter
and twin, 2-year-old sons who
stand a better-than-average
geneological chance of being
gifted and talented. By word and
deed, Alexander will teach them:
how to create, how to value, how
to climb and how to give up.
P.Cooper
“I
WAS ON A
SIDEWALK IN SAN
FRANCISCO, THINKING,
‘WHAT IS CAUSING THIS
TURMOIL IN MY HEART AND
SOUL?’ IT KEPT COMING BACK TO
THE PRESSURE OF BEING AN ARTIST.
I FINALLY ASKED MYSELF, ‘WHAT
WOULD HAPPEN IF YOU WEREN’T?’
AND THE CLOUDS PARTED. I
REALIZED I WAS TRYING TO
GET INTO A PARTY WHERE
I REALLY DIDN’T WANT
TO BE.”
“IT’S NOT ABOUT HOW FAST YOU
GET THERE, IT’S THE CLIMB.”