The New Zealander started last year's Vuelta a España with the brief of working for Steven Kruijswijk and maybe chasing a stage win, but ended up infiltrating the upper echelons of the overall standings and, after switching his focus to riding for the general classification following the Dutchman's exit, finishing 10th in Madrid.
Having entered his second Tour de France with no objectives beyond stage victories, his approach was once again turned on its head on Sunday's stage through the Jura mountains. Bennett finished seventh in Chambéry, leading the second GC group on the road alongside Nairo Quintana, Dan Martin, and Simon Yates, and now finds himself 10th overall – an evolution that must now be embraced.
"I've done quite a 180 on that one, actually," Bennett said with a grin, speaking to Cyclingnews in Périgueux ahead of the start of stage 10.
"I wasn't expecting to have any sort of ambitions for GC. I didn't think I'd be following the guys like that on a crazy mountain stage, but I had a really good day."
As was the case at the Vuelta, when he had to wait for Kruijswijk after a crash, Bennett again has that nagging sense of 'what might have been'. He crashed on the opening-day time trial in Düsseldorf and then sat back on the uphill finish to Longwy on stage 3. Those time losses didn't warrant a second thought at the time, but now it's difficult not to dwell on them.
"You're throwing away seconds and now I think they're going to be really important, actually," said Bennett.
"Maybe it's not all bad. Maybe it means I've just been cruising around at the back the sprint stages and haven't had the stress or anything, so maybe that's good. But yeah, I can't go back and get that time back."
Even so, Bennett acknowledges that a top 10 finish "is actually possible, which is cool". He currently lies 3:53 off Chris Froome, 47 seconds behind the race leader's teammate Mikel Landa, but over a minute ahead of Louis Meintjes and Alberto Contador.
"I'm trying not to get too excited about the prospect yet. It's definitely possible but I can't have anything go wrong – everything needs to go absolutely perfectly, and I'm going to need some super days," he said.
"I know what happens in the last week – guys like Contador and Meintjes aren't just going to lie down. I expect them to go ape shit in the mountains on the short stages, so I'm going to have to, I don't know, get creative.
"I should probably stop riding last wheel as well…"
Bennett, whose career seems to be moving through the gears since he joined LottoNL-Jumbo in 2015, is hoping his path to the Tour will have given him the freshness to compete with the best in the second half of the race. The 26-year-old has done four stage races this year, finishing no lower than 11th, his last outing seeing him win the Tour of California – his first pro victory – back in May.
"Planche des Belles Filles [stage 5] was the first intensity I'd done since California," said Bennett. "I did an altitude climb and we'd ridden long and hard but no intervals or anything, no intensity.
"I came here and was under the pump with intensity but you have a few days like Planche des Belles Filles and you come into form really well. So I'm hoping a few guys have got it wrong and were peaking at Dauphiné or something like that, or the first week, and I was going come in underdone and get some speed in me as I go along.
"I don't know. We've only done one week, and that's the crazy thing."