In his third year at the famous road race the Yeovil rider has made it into the top 20 in all four categories he has entered - Superbike, Supersport, Superstock and Senior.
Jessopp will be wearing number 18, which corresponds to his grid position, and whatever happens in qualifying and practice will not affect that placing. And he cannot wait to be mixing it with the best.
"To be seeded in all classes in only my third year is awesome," Jessopp said.
"In practice the top 20 just go out in pairs, so I could be alongside [John] McGuinness (reigning Senior TT champion) and to think of that is crazy. Although I have beaten them in other races, at the TT they are still the people I look up to and have so much respect for.
"Now I am in among them all."
Jessopp will have to push the fact he is up against his idols to the back of his mind, though. He needs to be beating them and building on the impressive reputation he has built for himself - one which has earned him his seeding in the first place.
"We are going into it the same as last year - although obviously hoping to go a little bit faster. I finished 14th in the senior last year with a top speed of 128.5mph, which for my second year was awesome," he said.
"It will take me all week in practice to get anywhere near that speed again because I have spent a year on the track. We want to push that speed up to what they call the 130mph club.
"I am starting in 18th on the track and no one is going past me and then hopefully we can make up a few places. Top ten would be the dream. But for that at the TT you need no bad luck and lots of good luck."
Jessopp has upped his game in road racing this year, with his Ridersmotorcycles.team deciding to go it alone in Supertwin with their own ER6 Kawasaki, as well as adding Supersport to the list for the first time.
"I have never ridden Supersport on the road before, but the Triumph 675 tested well in Spain. It is new for the team and we are learning all the time," he said.
"They [Supertwin] broke down in every race last year. It was a shame because they were faultless in practice, but then had mechanical failures in races. So we decided to take it into our own hands. It is a massive project."
Before the TT (May 28 to June 10), Jessopp will first be racing in the North West 200 (May 10 to 14) looking for better results than his sixth and seventh place finishes in in 2015.
"Every bike I sit on I want to be aiming for podiums. That is of course easier said than done because of how good the riders are, but that is the target," he concluded.
Thanks to the Western Gazette for the use of this story.