He stopped playing for three years when he left school, he watched from the bench for countless games, and he was told he was the third-ranked hooker in his province and should look elsewhere.
But he never threw in the towel and never walked away from the challenge.
If anything, those setbacks motivated him to keep playing.
Tonight, he should earn his 50th Super Rugby cap against the Stormers at Forsyth Barr Stadium.
"When I look back to 2001 to now, she has been a bit of a roller coaster ride," Rutledge said.
"I sat on the bench for three games in 2001, and then in 2004 I got 17 minutes for the whole season behind Anton [Oliver]. She was a long season.
"It was very frustrating. But Anton was one of those players who did not like coming off and that was just the way things went.
"But I came in as a young guy and did not really fire any shots at Anton. I should have maybe tried to knock him over at training. But I just cruised along. That cost me. I did not come back for another five years.
"I went away and two years after, the Southland coach asked what my goals were and I said I wanted back in the Highlanders. By the look of him, he said that door is closed.
"By then I was ranked third in Southland, and told I should go to Tasman and go down that avenue. It was pretty disheartening.
"But I took it on the chin and said, 'No. I'm staying', and it has gone well. It could have gone the other way."
Rutledge (34) will come off the bench tonight as Andrew Hore comes back into the starting side after a week off in the only change to the Highlanders side.
Rutledge would love to start, but understands he is playing second fiddle to All Black hooker Hore at the moment.
"I have just got to keep taking my chances. It helps Jamie [coach Joseph], I suppose, that he can draw on the likes of me and Jimmy [Cowan] to help close out these games which are pretty tight. I'd rather be starting but it's working at the moment."
The player nicknamed "Cabbage" did not start a game for three years after leaving school.
Playing for the Southland Boys' High School First XV, he received several blows to the head.
"In the top four for Southland Boys', I was knocked out against Kelston. That was my third one for the year.
"Mum sat me down and said, 'This is not good. You have to have three years off.' I went away coaching.
"I hated it in some ways but it was the only way I could keep involved. I came back, played a year at fullback, and not had a head knock since."
Rutledge and the bench will be vital tonight as the Stormers' defence is put to the test. It is the best in the business and gaps will be few and fair between.
But the Stormers have had to endure a tough game against the Bulls, followed by a flight to New Zealand, and there may be doubts over whether the side can last 80 minutes.
The Highlanders will want to go into their bye week with a win in the bank. The side will not lack for motivation, with halfback Jimmy Cowan bringing up his 100th game for the franchise off the bench. A public presentation for Cowan will take place after the match.
Much will depend on the Highlanders' ability to break the Stormers line and hang on to the ball for long periods.
The Highlanders confirmed yesterday first five-eighth Mike Delany had still not signed with the franchise. He was also carrying a couple of niggly injuries but should be available for the match against the Blues on April 20.
