Andy Barcham has already clambered out of League Two twice.
Now the Pompey newcomer is banking on his Fratton Park switch to once again elevate him out of the bottom division.
It was Wembley which formed the backdrop to a glorious play-off victory for Gillingham in May 2009 with Barcham at the heart of it.
The former Spurs youngster was an automatic choice in the team who defeated Shrewsbury courtesy of a last-gasp Simeon Jackson header.
The left winger ended the season as second-top scorer with nine goals in his 41 games for the fifth-placed finishers.
However, 12 months later Mark Stimson’s men were back in League Two after suffering relegation, costing the former Pompey defender his job.
In 2010-11, new boss Andy Hessenthaler’s team missed out on making the play-offs by goal difference.
Barcham then sealed a switch to Scunthorpe, securing the midfielder a route back into League One, having been out of contract.
Now, two years on, Barcham has a new home in Pompey – but his ambition to escape League Two remains undiminished.
He said: ‘I know what promotion is like, I had it at Gillingham and they were good times.
‘You’d probably like to go up as champions so you don’t have to worry about possibly not going up through the play-offs.
‘We did it through the play-offs, though, and it was fantastic and a great way to get out of League Two.
You get the game on Sky, the semi-finals, the two legs – and we got our day at Wembley. That was the added bonus.
‘We had a great team. Simeon Jackson was our striker and has since gone on to bigger and better things but we had a very good side and did very well.
‘He was probably the most recognisable one out of that team and we stayed together when we went up, too.
‘We then gave it our best shot in League One but it just wasn’t meant to be.
‘We got to play in League One, there were some big teams in it such as Leeds and what really killed us was we struggled away from home. That is why we got relegated.’
Barcham featured for Scunthope in League One, scoring 11 goals in 84 games, before signing a three-year Pompey deal.
And armed with his League Two knowledge, he’s hoping he can help lift the Blues out of the bottom division.
He added: ‘It is a tough division to get out of but if you can get a good run going and a good start then it can be done.
‘Everyone will look at it and think they can have a go at it this season and we are no different.
‘We are in the bottom tier and everyone to do with the club wants to push on and start working our way forward, towards where the club should be.’