Toby is a great songwriter. I remember sitting in the Bluebird in Nashville and him coming in to play a writers night, just like anyone else. No one knew who he was, had ever seen him, or even knew that in a few short weeks he’d release his first Major label record… before he sang. After he sang everyone in the whole place knew who he was.

“Should’ve Been a Cowboy” was one of the songs and I remember looking around the room. Everyone’s faces (ameteurs all) were saying the same thing “THIS is a HIT song!”

When the next guy was on stage playing, Toby was trying to make his way outside. The guy stopped playing in the middle of his own song to ask, “hey man, what’s your name again? you were great”. “Toby” was the reply, and with that the crowd erupted in applause.

I’ll never forget that night. Something in the air said, “there goes a real songwriter”. It’s remained that way ever since.

Toby has to his credit:

BMI Awards:
2005 Country Award Winner for “Stays In Mexico”
2005 Country Award Winner for “WHiskey GIrl”
2004 Country Award Winner for “American Soldier”,
2004 Country Award Winner for “Beer For My Horses”
2004 Country Award Winner for “I Love This Bar”
2003 Country Award Winner for “Courtesy of the Red, White and Blue (The Angry American)”
2003 Country Award Winner for “Who’s Your Daddy”
2002 Country Award Winner for “I’m Just Talkin’ About Tonight”
2001 Songwriter/Artist of the Year Winner
2001 Country Award Winner for “You Shouldn’t Kiss Me Like This”
2001 Country Award Winner for “Country Comes To Town”
2001 Country Award Winner for “How Do You Like Me Now?!”
2000 Country Award Winner for “How Do You Like Me Now?!”
1999 Country Award Winner for “Dream Walkin’”
1998 Country Award Winner for “Me Too”
1997 Country Award Winner for “Does That Blue Moon Ever Shine On You”
1996 Country Award Winner for “You Ain’t Much Fun”
1995 Country Award Winner for “Who’s That Man”
1995 Country Award Winner for “Wish I Didn’t Know Now”
1994 Country Award Winner for “He Ain’t Worth Missing”
1994 Country Award Winner for “Should’ve Been A Cowboy”

With that said, you might can understand where his confidence comes from when, in an article he states:

“”I always feel like I’m a good idea away from a great song,” Keith said on the phone from a Cleveland tour stop.

“If I have a great idea, I can tell you the second I get the great idea [that] I’m going to make a great song out of it. I’ve done that so many times, I’m very confident I can sit here and tell you that.”

We can all learn a lesson from Toby, and not just about songwriting. Toby has confidence, and yeah, he has a reason to have it - but so do all of us. We all excel in one way or another, be it melodies or lyrics. And if we’re not excelling, we’re at least improving, and that should give us all the confidence in the world!