Ryan Giggs finds himself at the proverbial crossroads in his career once again, but if he aspires to be anything more than just a part of the furniture at Old Trafford - he must walk out the door.
The 42-year-old has always been touted as a potential future managerial candidate at United, given that his associations with the club spans across almost three decades. And most assumed Giggs' appointment as Van Gaal's assistant manager was made with a view for him to eventually take charge.
But like most things since the departure of Sir Alex Ferguson, nothing has gone to plan at Old Trafford. Louis Van Gaal's reign of terror at the club was ended after the FA Cup victory over the weekend - with Jose Mourinho on the verge of becoming his successor.
Sky Sources: Jose Mourinho prepared to offer Ryan Giggs role on coaching staff but not as assistant manager. #SSNHQ
— Sky Sports News HQ (@SkySportsNewsHQ) May 24, 2016
For Giggs, he must look at the bigger picture. Mourinho will likely appoint Rui Faria as his assistant manager, who has been with the former Chelsea boss throughout his career - which will leave Giggs in limbo.
It's been reported that Giggs could be offered the U21 manager role in Mourinho's setup, but for someone whose ultimate goal is to manage - and to be the Manchester United manager, perhaps he should leave, and prove his worth elsewhere.
The problem is that if he were to leave and takes up another job, failure could almost rule him out of ever becoming Manchester United manager - taking the U21 job potentially could see him follow a similar route to the top than that of Zinedine Zidane at Real Madrid if things were to go very wrong for Mourinho.
Speaking to Sky Sports this morning, United club legend, Peter Schmeichel, echoed the claim that Giggs wants the top-job at United, but believes he must leave the club and prove himself if is ever to be considered for the position.
Schmeichel on Giggs: "I think to be equipped (to manage #MUFC), he has to go away, stand on his own two feet" #SSNHQ https://t.co/1EW5mUMvgL
— Sky Sports News HQ (@SkySportsNewsHQ) May 25, 2016
There are two sides; the club's side and Ryan's side. I think Ryan's big dream is to one day manage United.
To be equipped to do that, he has to go away and be a manager at other clubs - standing on his own two feet, making decisions, producing results, getting his own ideas - rather that step-up from being assistant.
I think, for him, it would to be a good idea to somewhere else. On the other hand, Ryan is a culture bearer. He is someone who has been at the club for a very long time, and it's important we have that within the club.
He is someone who knows what the club is, knows the tradition and history - knows everything about it. Whatever he decides, it's down to him and, whatever he decides, I think that will be the right decision.
But I would like to see him go away and come back some day prepared for the challenge because we've seen that, in the last three years at United, it's a hard job to be manager there. It's not something you can just step up and do.
Such is the modern day revolving-door at football clubs, Giggs could take his chance - learn his trade under Mourinho, and play the waiting game. Mourinho's tenures have never been long term. He comes in, wins trophies, and exits in the blink of an eye (usually in controversial fashion).
But maybe United is the club to finally tame Jose Mourinho - because he's at the point of his career where it's probably time to settle down. Giggs can't become fixated on the fairytale ending that may never come through.
He must reject and bit-part offer he will be offered by Mourinho, and strive for better elsewhere - because the offers are certainly going to be there. If he achieves any kind of success, United will surely want him back somewhere down the line.