Mauricio Pochettino has managed Tottenham Hotspur valiantly in recent years, leading the club back into the Champions League and making contenders for the Premier League title. However, the Lilywhites have fallen short.
Last year, in a two-horse race for the title, Spurs somehow managed to finish third. On the European stage this season, they've lost both of their 'home' matches at Wembley and are in real danger of a premature exit from the Champions League.
Despite standing unbeaten in the Premier League this season, Spurs have looked far from their best. In such a fierce race for the top four, it appears at this stage that it's Spurs who will miss out. If that happens, then it will raise serious concerns as to whether the Lilywhites have reached a glass ceiling in their quest for greatness.
Spurs' quest is long-term but players need to live in the here and now, which means these three need to think about moving on.
Erik Lamela
Arriving amongst a flurry of activity as Spurs splashed the cash earned by Gareth Bale's sale to Real Madrid, Erik Lamela initially struggled to shine in the Premier League. Slowly but surely though, the Argentine has shown his ability.
Now 24, the former Roma man will want to be playing Champions League on a yearly basis. Spurs cannot yet guarantee that and still have the financial battle that will come with their stadium expansion. Lamela also has his international career to worry about and Argentina have a steady supply of top-class wingers.
Dele Alli
The hotshot of English football is deemed to be one of the most talented up and coming players in the world. Whilst we've heard that time and time again from the British press, the evidence is there to back up the claim.
English football's biggest restriction in recent years has been the lack of variety in experience; it's been a long time since an English star plied their trade abroad during the prime years of their career. Alli could be an exception though, if he takes the plunge.
Alli faces a dilemma - stay with Spurs and follow the same, well trodden path led by many English players before him, or fulfil his potential with one of the biggest sides in the world and lead the way for a new age for English football.
Hugo Lloris
The 29-year-old has been very patient and loyal to Spurs in recent years, sticking by the club and their vision of returning to Champions League football. Had they not finished in the top-four last season, it's highly likely that the French international would have moved on.
Captain of the side and his nation, it's a massive year ahead for Lloris and Spurs. If they finish outside of the top-four this season Lloris, who will be 30 next summer, then the Euro 2016 finalist is likely to seek a move on once again.