This is a passage from Dr. Phil's interview with Romo that I thought relevant in relation to his actual thinking and events at the time:
"It was actually weirdly made easier when I felt like they were in good hands. That part of it, it gave me a feeling of, ‘okay, I wasn’t necessarily thinking this right now, but it was coming around the corner pretty soon,’ and then it was... I know I’ve given everything. But I will continue to do this until 58 if it took to win a Super Bowl, it’s like I’ve got to get out of my own way in some way and be a dad, and do something else."
The article's title is correct from Romo's perspective. In addition to Prescott running the offense competently, the offense gained a superb running back in Elliott. The offensive line was effective and cohesive. Receivers were adequate or better and Witten was still there. The defense was beginning to show signs of promising improvement in certain areas. Special teams had an solid duo in Dan Bailey and Chris Jones. Garrett & staff had coached to a degree that more aided than prevented the team from finishing as the number one seed in the NFC. Ownership had been drafting well for several years.
All things considered, Romo could see the team being in good hands with all those factors in consideration. However, Romo does add he 'wasn't necessarily thinking this right now' even though he knew 'it was coming around the corner pretty soon'. So the thought of retirement was being pondered but was not decided by him. Additionally, Romo stated 'I will continue to do this until 58...' with 58 being an obvious Romo crownie exaggeration but it reinforces the conclusion he was not going to retire at the end of the 2016 season under different circumstances.
What were the different circumstances? There was only one. Jones and Garrett's refusal allowing Romo's return to the starting lineup. Romo's driving motivation was leading the team--this franchise--to a championship. Jones and Garrett's external decision made Romo's inner decision to:
a) stop seeking a goal he had no control of achieving any more and
b) focus on both the other important aspects of his life and re-direct his career self-motivations
--pretty gosh darn easy with the cards that were dealt to him. And yes. Romo's health was a strong discussion point between Candice and himself but it was not the 'final nail in the coffin' some allude it to be. The analogy is appropriate though if some people wish to rename one nail 'Jones' and the other nail 'Garrett'.