Born and raised in Bellevue, Washington, Schilling grew up playing basketball until high school.

He became a star offensive lineman who was a standout Seattle athlete as his high school won its third consecutive state championship in his junior year.

He won numerous all-area and all-state honors as a junior and a senior and was highly touted on the national level.

When the team transitioned from head coach Lloyd Carr to Rich Rodriguez during his redshirt sophomore season, he became one of the few experienced players to endure the change.

He was honored as the 2008 Michigan Wolverines football team's best offensive lineman as a redshirt sophomore before being nationally recognized as a Lombardi Award watchlist candidate in 2009.

He was activated prior to week 8 of the 2011 NFL season (his rookie year), and played in several subsequent games for the team.

When Schilling was young, he was too large to play organized football with kids his own age because Bellevue's youth leagues were regulated by weight-age limits, which caused him to take up basketball instead.

[3] During the summer prior to his freshman year, Schilling first visited the Bellevue High School weight room where he noticed the intensity and camaraderie.

[6] The championship, which came as a result of a ten-game winning streak to close the season, made the Bellevue Wolverines three-time Class 3A state champions.

[7] On September 4, 2004, as a junior, he helped Bellevue end the high school football record 151-game winning streak by De La Salle High School in front of 24,987 at the second annual Emerald City Kickoff Classic at Qwest Field by a 39–20 score.

[19][20] In July prior to his senior season, he was included in a Reebok Western All-American list in Sports Illustrated.

On September 16, 2009, they defeated the Long Beach Polytechnic High School, who had been ranked number three by the USA Today.

[29] Schilling was one of sixteen nominees for the Parade All-America High School Player of the Year award.

[39] He made his final selection in what has become a traditional recruit announcement technique by using the schools' caps in front of his extended family, including his mother who is named Joanne and a sister.

[40] Sources: Schilling did not arrive in Ann Arbor, Michigan in time for 2006 spring practice like some of his classmates.

[42] In late October, he decided to redshirt and have a second shoulder surgery after having missed weeks of practice and lost much weight.

[45] He was the starter on September 1 during the opening game loss to two-time defending FCS champion Appalachian State Mountaineers.

[49] Although, he had to stretch beyond his past experiences and natural position, he was able to seek fifth-year seniors Jake Long and Adam Kraus as mentors.

[50] With the departure of Mike Hart, Mario Manningham, Adrian Arrington, Jake Long, Chad Henne, and Adam Kraus to the National Football League and Justin Boren's defection from the team, the 2008 Michigan Wolverines football team entered the season for new head coach Rich Rodriguez with only three returning offensive starters: Schilling, tight end Carson Butler and fullback Mark Moundros.

[51] Backup quarterback Ryan Mallett transferred and two senior offensive linemen (Jeremy Ciulla and Alex Mitchell) declined to use their fifth years of eligibility.

[67] He was also, elected co-captain and participated in a season long fanmail program where he responded to Michigan fan questions made by email and on Facebook every Friday.

[74] Schilling was one of 56 offensive linemen invited to participate in the February 24 – March 1, 2011 NFL Scouting Combine.

[79] Schilling was selected with the 201st overall pick in the sixth round of the 2011 NFL draft by the San Diego Chargers.