There's been steady production, big pay days, physical setbacks, and yes, more than a fair share of disappointment for both player and organization.
Romo continues to keep an optimistic perspective as he begins his ninth year as a starter. In an exclusive interview with NFL Media's Desmond Purnell, Romo explained his forward-leaning mindset.
"You know I'm not into the looking back kind of thing," Romo told Purnell when asked how he'd sum up his career. "You know when I'm done playing I'll do that but right now it's about improving and I'm not done growing as a football player, I have to keep getting better.
"If I don't get better, it doesn't help our football team. We weren't good enough before and it just means that I have to be a better player to help this team get to where we are trying to go and that's my ultimate goal each year."
In reality, Romo has been plenty good enough in his time in Dallas. It's the cast around him that never seems to be up to snuff. The Cowboys are a shiny McMansion built on a bum foundation.
Year after year, it's Romo who pays the price for that shoddy craftsmanship.