There are moments from his Scotland career, opportunities to grace a World Cup that slipped by, for example, that still sometimes keep Steven Naismith up at night.
“Too many, too many!” Naismith said.
“At least one, maybe two in every campaign.”
Although he never quite made it to a major tournament as a player, the former Kilmarnock, Rangers, Everton and Hearts striker was a fine servant for his country, earning a place in the national team’s roll of honour with 51 caps and now serving Scotland for the second time on the coaching staff in the capacity of assistant manager to head coach Steve Clarke.
So, he was as delighted and as proud as any Scot when Clarke led his team to a second consecutive European Championships last summer, even if he had a wry smile as fate denied him yet another chance to experience a major tournament.
“There was real jealousy there because you're just on the back of beating Spain at home,” he said.
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“It's a significant moment – you go, 'if we do what we have been doing, we make it'. I'd missed out as a player. You're coming to the end, and you're trying to hang on, and you don't make it.
“I've spent the last 20 years thinking about it from a player's point of view, then you get the opportunity at coaching.
“Listen, these are these moments in football [the Hearts job] that come along and you've got to make the decision. I made it. And fortunately, the manager has seen that I can add value at the moment.
“It is slightly different, the condensed period that this is - we could be sitting three months' time at a World Cup. What a target that is to have for three months' hard work.
“That probably helps, how condensed and how big it is. It's small margins. One result can be the difference. We're sitting in a group where everybody will sit there and feel they've got a chance here to go through.
“That tells us that if we really focus, really have that fight and determination to do the stuff that's not necessarily ability-related, you put yourself in a good opportunity because we've got players in the prime of their career who have been to tournaments and who probably have ticked every box.
“This is just the next one, so it's there and you can see what's there at the end of that. So, the optimism has to be high.”
Perhaps unsurprisingly given that Clarke has again seen fit to employ him, Naismith is a huge fan of the Scotland head coach, who he places among the very best managers he has ever worked with throughout his long career in the game.
He was dismayed then to see the criticism that came Clarke’s way after a hugely disappointing Euros, but while he thinks that his legacy as a Scotland great is secure no matter what happens in this campaign, Naismith believes that qualifying for the World Cup would underline his boss’s status as one of the best to ever grace the Hampden dugout.
“That's just this culture nowadays,” he said.
“I think in every job you can see it. I've seen it as a manager myself, going through a period where it's not perfect. Everybody's just thinking perfection happens now and we just keep going with perfection. It's not realistic.
“Don't get me wrong, the manager's the first person to say, we need to go to the next level, so he's always pushing. But you cannot take massive jumps, especially in international football, when you've got the players for such a limited time.
“You're putting a lot of onus on the players and their intelligence and their understanding. I think he's bridged that gap really well. He's not got bogged down with anything. He's not had that zoomed-in lens to go, ‘We need to change this’. It's all very structured, and that's why we have been successful.
“Yeah, I would [put him in the top bracket]," he continued.
"Again, every manager's different. I think I've personally taken from different skill sets of managers, and how they work, whether it be the tactics, the man management.
“But I think where the manager is in his career, you can tell the experience he’s had from the many years at Chelsea, working at that level as a coach. Obviously, he had a stint at West Brom that had success, but very quickly things change. That calmness, the tactical understanding and knowledge of what you need, through probably a time in football where it's rapidly changed from the slow changes that happen year on year. So yeah, I appreciate the learning I've managed to gain from him.
“Even just the qualifying percentage of his results is up there at the moment. Like anything, in 20, 30 years' time, we'll look back and go, ‘he was really successful’.
“But I think if you manage to go to a World Cup, it's some achievement that will definitely put him right up there with the best.
“Things have changed, formats have changed, the calendar for internationals has changed, but before he took over, we were in a place where everybody would have chopped their hands off to get to a World Cup or a Euros.
“Now, for a generation of kids, it's been normal. That tells its own story.”
