But he knows when that day arrives, the Manchester United midfielder will be able to look back on his career and say he squeezed every last drop from it. The 29-year-old, who is recuperating after surgery to cure the serious bowel condition ulcerative colitis, has been ruled out for at least the rest of the season amid legitimate fears his career may never return to its previous heights.
Although Fletcher has so far declined to hook up with the Scotland squad for Wednesday night's friendly against Estonia at Pittodrie, Strachan is a huge admirer and is keeping the door open for him to come and run the rule over the new Scotland set-up as soon as he feels up to it.
"There's an open invite to come any time and sit in to be a part of it, to listen in to the coaches and hear what they've got to say," said Strachan. "I've spoken to him a couple of times. He just has to get himself feeling better – and feeling better about himself – to get back.
"No matter what happens to Darren, on the day when he does pack in football he can look back and say: I gave it my best shot and got as much out of the game as I possibly could. He's playing for a wonderful side and has some great memories already. There are some great footballers who end up being bitter for the rest of their lives because they finish the game and think they should've done more with what they've got and maybe get envious about what people are doing now. Darren will not have that. There are others such as Gary Caldwell (who scored for Wigan against Southampton yesterday) who will finish and know he did the best he could do with the ability God gave him. Those are special people and you admire them."
The news of Fletcher's surgery came just hours after the former Coventry, Southampton, Celtic and Middlesbrough boss took over as national team manager, but such early setbacks are hardly new to the 55-year-old. Strachan recalled losing Kevin Thomson to injury on day one at Middlesbrough and saw the club's talisman Adam Johnson sold to Manchester City, while his first match as Celtic boss resulted in a 5-0 defeat to Artmedia Bratislava.
Fletcher's absence is compounded by the fact two other senior players who might once have been assumed to be mainstays, Craig Gordon and James McFadden, are suddenly nowhere, but Strachan hopes others can step up and assume part of the leadership burden. "I hope there are some strong leaders in there," he said. "I don't know them all, but I know a lot are strong characters. Gary Caldwell is a terrific lad and I saw him the other night against a strong, physical Stoke side when he and Shaun Maloney were the best two players on the pitch."
Kenny Miller is another such figure. Strachan has been around the Scottish scene so long that it seems he has previous with almost everyone, but his past life with Miller is particularly interesting, having signed him for Celtic then sold him to Derby.
In all likelihood, the 33-year-old will have to start from the bench on Wednesday, having fallen behind the likes of Steven Fletcher and Jordan Rhodes in the Scotland pecking order, but such a minor indignity did little to stop him travelling from Vancouver.
"Kenny has that presence about the place, he's good with people," said Strachan. "If he's still as fit as he was two years ago then that's fine, it means he can still do the same. I said to him I might try something else to start with, but you're still in my thoughts and there's no doubts about that. I don't know how long you are going to play, but do you want to come across or not? He said he did. So I thought, fine."
While a goalkeeper of Gordon's class is unable to find a club, Strachan is delighted to inherit his long-term successor. Allan McGregor was occasionally a thorn in Strachan's side in Old Firm battles, and a cursory viewing of the Macedonia match shows how integral a figure McGregor has become for his country. The 31-year-old, now at Turkish outfit Besiktas, has a capacity to make headlines on the front pages as well as back, but having dealt with the occasionally wayward antics of Artur Boruc, Strachan is hardly a novice in that regard.
"I keep watching games and I saw him against Macedonia and thought the game was eeksy-peeksy," said Strachan. "Then I looked at it again and thought: he's made four absolutely brilliant saves. You can't ignore that.
"He is a good goalie and they get better when they get to their 30s, I think. It's a bit like centre-halves, that's them at their best round about that time. He's a bit of a character, but I saw one of them making a wonder save the other night – Artur Boruc. That's a real character. McGregor is playing at it compared to Artur!"
Of all the 28 members of Strachan's initial Scotland squad, none has had a more unlikely journey than Charlie Mulgrew, a man who was let go as a teenager by the then Celtic manager only to make himself unignorable as cover for multiple positions on the strength of form which made him last year's Scottish Football Writers' Association player of the year.
"I never had a cross word with Charlie in my life," said Strachan. "I just think there were a group of players at Celtic who needed to get out. Some have flourished like Charlie, some have collapsed. If you look at a lot of the Celtic lads, they can either go away and kind of grow up or go away and die.
"They've been protected by Celtic and actually look good because they're playing with really good players. Then they have to get into the real world. Because of the Under-21 rule, the young ones weren't really getting games yet were living in a fantasy world of picking up bonuses.
"Charlie moved at the right time because if he'd stayed another year then I think his whole drive would have collapsed. What he did was get out there, take a few knocks at Wolves, Southend then get to Aberdeen and play better and eventually make his way back to Celtic as a real mature man."
Strachan named a big squad, mindful of getting through the weekend's games relatively unscathed, with a renewed focus on attacking players with a trick or two such as Chris Burke and Ross McCormack, while the likes of James Forrest and Matt Phillips keep their places. "It's playing with people who can beat people, do something different but still be able to work hard at the same time," Strachan said.
He is mulling over two possible team selections, and will see how things transpire at the weekend and in training before deciding who makes the final cut. "I've got two teams and two formations in mind," he said. "I am excited. I'm excited with the goodwill that's been handed out by everybody to me. But you don't get too excited otherwise you'll get too disappointed."
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