It's not like he hasn't been here before.
Former unified flyweight world champion Brian "The Hawaiian Punch" Viloria (36-4, 22 KO's), has fought and beaten and lost to the A-listers in and around his division.
The one guy he hasn't faced, consensus best flyweight in the world and pound-for-pound entrant, Roman "Chocolatito" Gonzalez (43-0, 37 KO's), he fights on October 17 at Madison Square Garden in New York.
The challenge and the reward should he overcome said challenge however, Viloria explains, is unlike any other he has experienced in his career despite often finding himself caught between being champion and contending for a title.
And while the challenge is just as, if not greater than the reward, one thing Viloria says he's wanted all along is to be considered among the world's best, with or without a belt around his waist.
"To get on the pound-for-pound list, I think that's one thing I really, really wanted to be on before I hang up the gloves," said Viloria.
Now, on the tail end of his colorful professional career, Viloria gets to do just that, against a man who many view to be one of the best little fighters of all time.
Gonzalez can be found up as high as number two on The Ring magazine's pound-for-pound top ten, sitting right underneath Floyd Mayweather himself. By comparison, Manny Pacquiao is found at number six.
The Nicaraguan knockout artist has certainly earned his chops, continuing to beat whoever is put in front of him and with relative ease.
The last man who gave Gonzalez a good run, Juan Francisco Estrada, is also coincidentally the last man who defeated Viloria.
Since Estrada however, Gonzalez has strung together nine straight knockout victories and is looking extremely mighty. Some say he's even more dominant at flyweight than Mayweather is at welterweight.
But, being no stranger to this type of adversity, this won't be the first time Viloria will face a top ten pound-for-pound fighter.
In 2011, Viloria fought and beat The Ring's number nine pound-for-pound entrant, Giovani Segura and he did so with relative ease.
On full display was Viloria's devastating knockout power, as he beat Segura up so badly he caused a hematoma to swell into a grotesque ball of blood on Segura's head. Doctors had no choice but to stop the fight to prevent further injury to Segura and the Mexican-American was never the same again.
After unifying the flyweight titles for the first time in nearly 50 years by defeating the dangerous Hernan Marquez, Viloria was on the cusp of breaking through the top ten, sitting just outside of it by a few paces.
"I think this is the biggest chance I have to do that, to crack the top ten pound-for-pound list and just to put up great fights," said Viloria.
"I think that's my intention in each and every fight -- to go out there and put in one of my best fights and to show everyone that I can still be on top."