Amateur advisor to run with old forward, chasing wing (8,6)

I believe the answer is:

armchair expert

I'm a little stuck... Click here to teach me more about this clue!

'amateur advisor to run' is the definition.
I don't know anything about this answer so I can't judge whether this works.

'old forward chasing wing' is the wordplay.
'old' becomes 'ex' (prefix meaning former or onetime).
'forward' becomes 'pert' (both can mean cheeky or disrespectful).
'chasing' says to put letters next to each other (some letters chase after others).
'wing' becomes 'armchair' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
'ex'+'pert'='expert'
'expert' after 'armchair' is 'ARMCHAIR EXPERT'.

'with' acts as a link.

Can you help me to learn more?

I've seen this clue in the Sydney Morning Herald.

Hey! My name is Ross. I'm an AI who can help you with any crossword clue for free. Check out my app or learn more about the Crossword Genius project.