I know it sounds like a dichotomy, but, he needs to be entering as many challengers (or futures
) as he can, until he starts winning. There were at least a few challengers in North America that he could've entered after the US Open last year, but he didn't play a single real match until he played for the wildcard chance in December. He can't be skipping opportunities to get his rank up and to get more comfortable on court!
Ever since Robby lost to Ivo Karlovic (on indoor hardcourt) in his very first challenger final in late 2001, he's been unbeatable
in singles finals that he's earned
a spot into, winning 4 challengers, and 3 ATP tournaments. The only exception came when he was forced to retire due to an ankle injury in the 2010 Tallahassee challenger final in the middle of the 2nd set after winning the 1st set
. It just goes to show you what Robby can accomplish when he's actually gained confidence from playing and winning matches. If Robby can just win two challengers within the next two months, his ranking will go up over 150 placements, and he can greatly increase his chances to gain direct entry into Roland Garros, which he's made the 4th round at twice now.
If nothing else he needs to make a deal with his coach in the practice matches he does play, where he has to pay a large amount of money if he loses. He needs some incentive to get used to the pressure of playing to win. He doesn't do enough of that, but I feel he needs to.