THIS is a new challenge for John Longmire.
Set to enter his 11th season in charge of Sydney, Longmire – the club's longest-serving coach and the third longest-serving active coach in the League – has enjoyed and endured his fair share of testing moments across a decorated career at the helm of the Swans.
But while the start of his coaching career included a premiership in 2012, three Grand Finals in five years stretching to 2016, and eight consecutive finals appearances lasting to 2018, the next mountain to scale is a far more unique, and perhaps daunting one altogether.
Now, Longmire is presented with the task of rebuilding a Sydney side that hasn't waded through a finals drought lasting beyond the two seasons that it currently stands at in more than a quarter of a century.
Where once Longmire's Swans returned to pre-season training every January expecting to be the last team standing on the final Saturday in September, now they come back with their eyes firmly focused on simply seeing September once again.
It presents the 50-year-old coach with a new outlook on the campaign ahead, and even a change in expectations from week-to-week. But, all the same, it still presents him with a challenge that continues to excite and motivate.
"It's a different challenge. Both challenges are big," Longmire told AFL.com.au.
"When you're at the top, we played three Grand Finals in five years, the challenge is still big because the expectations are still there. If you're aiming for top-eight, it's not good enough. Top-four isn't good enough, you want a home final. It becomes top-two, but then you want to finish on top. You're always aiming a little bit beyond where you currently are.
"You need to keep trying to improve and you're always looking over the horizon, having those expectations and aiming for the top. That was certainly a different phase. Now we're going through a phase where we're making sure we get that group together.
"It's a considerable number of players that we've turned over during the last few years. Now, we're trying to build them into a team that we know is going to be competitive for a regular finals berth. And it's regular, it's not just a once-off. We're aiming for a period where we can challenge year in, year out.
"That's where we're trying to get towards, but we're trying to do that as fast as possible. We're impatient, but there are also some realities that we need to take on board as we go."
Fortunately, Sydney is already finding gems among a young crop of highly talented and promising new players as the gradual list rebuild continues.
Of those not yet 25 years of age, Isaac Heeney has already played 100 games, while Tom Papley and Callum Mills will almost certainly reach that landmark this season. Ollie Florent, Will Hayward, Tom McCartin, Nick Blakey, Jordan Dawson and Lewis Melican are others with significant games totals under their belts.
But while senior experience is one thing, it's not a certain indicator of improvement. Sydney's win percentage dipped from 36 percent to 29 percent last season, resulting in a finish just three spots from the bottom of the ladder. It was the club's lowest finish since it 'won' the wooden spoon in 1994.
But with two more top-five NAB AFL Draft selections joining the list courtesy of the recruitment of Logan McDonald and Braeden Campbell last December, Longmire's next focus is getting that group back on an upward curve and winning games again. The familiar old task of challenging for significant honours lies in wait after that.
"The belief and experience of playing together is critical, but it's not just games itself that lends itself to improving," Longmire said.
"You don't just tick off the games and say you're going to get better, just because you've played them. You still need to work really hard, you need to be confident in each other, know each other's games, and you need to do the things on and off the field that you know successful teams do.
"We're taking that step and hopefully we take that step quickly, as quick as what we and our supporters would like us to do. But we also understand that it's a pretty big step. We're working towards getting that done and working towards trying to be a competitive team week in, week out."
Sydney's focus recently has been firmly directed towards the draft. Since being forced to match a bid on gun Academy prospect Mills in 2015, the Swans have welcomed eight first-round picks in the last six years and haven't gone without a first-round selection since trading for Ted Richards in 2005.
The club has benefited from the arrival of Mills through the prolific success of its Academy, which has also spawned fellow first-round talents like Heeney, Blakey and Campbell in recent seasons. But this hasn't stopped it from prioritising and retaining its own early draft selections.
Florent (pick No.11 in 2016), Hayward (pick No.21 in 2016), Matt Ling (pick No.14 in 2017), James Rowbottom (pick No.25 in 2018), Dylan Stephens (pick No.5 in 2019), Will Gould (pick No.26 in 2019) and McDonald (pick No.4 in 2020) have also come through the door via the draft recently, highlighting its investment in this phase of the club's future.
That, along with salary cap constraints, have come at the expense of the Swans being a major player in the free agency market. Gone are the days of the club chasing the likes of Lance Franklin and Kurt Tippett at season's end.
The earliest selection Sydney has parted with in a trade since giving up that first-round pick for Richards in 2005 was when it relinquished pick No.22 in a package deal for Mark Seaby in 2009. Last summer, the only arrival was Tom Hickey from West Coast in exchange for a combination of pick swaps. It hasn't signed a free agent, aside from delisted players, since recruiting 'Buddy' in 2013.
But perhaps that will change now. As the list continues to grow and improve from within, Sydney expects to again be the force it once was at the Trade Table in the near future. But, as is often the case, a lot of that strategy will ultimately still depend on the team's progression over the next 12 months.
"We will (enter the free agency market again) at some point," Longmire said.
"We haven't been at the forefront of that over the last few years, even though we've got players from other clubs. If our supporters are looking at where we're sitting in that space, after being pretty aggressive for a number of years, we're not right at that aggressive part of that now.
"There's a bit going on with our list management that we need to consider, both position-wise and salary cap-wise. When we look at that in its entirety, our priority has been to re-sign our best young players. That's where our energy has been diverted, into recruiting and then retaining our best young players. We've been able to do that and I'm sure that will continue, hopefully in the coming weeks. We've got a real focus on doing that.
"If we can add some players, there's no question there's always holes on a list and you can't just fill them all through the draft. Every club needs an avenue to explore to be able to do that and we're no different. If we can do that over the next coming years, we'd love to be in the position to do that."
So, after two years without tasting post-season football, is the 'F-Word' back on the lips of those at Sydney?
With the first-round picks of the last six years tipped to continue their progression this season, and with experienced leaders like Josh Kennedy, Luke Parker, Franklin and Dane Rampe still anchoring key spots on the park, the Swans appear destined to be back on the right track once again. Not that their coach is getting carried away just yet.
"We'll have to wait and see," Longmire said.
"It's not something that I dodge for the sake of being afraid to answer the question, it's just that there are so many unknowns. If you look at last year's unknowns, there's plenty of those still going around.
"What we do know is that if you work hard and you've got the talent and you're competitive, it gives you the best chance. Those are the areas that we're looking at and those are the areas from week-to-week that we can build on. That will give us the best possible chance."