For a different discussion since why he would get fired by his non employers is well covered.
I think he's found that too much of his success is contingent on what others do and there's much he simply can't do.
As he has stated he works for the board, they like it when he can spend as close to zero dollars on the series as possible and after stopping the losses start making money. Jeff Belskus smiles and Randy gets a pat on the back. Unfortunately that means Randy doesn't have money to spend on promotions, or to offer incentives to teams or bigger purses because unlike in the Tony George days the purse strings are closed.
He is handcuffed by the remaining 6 years of a ten year TV contract with NBC Sports Network and had further restrained by the just extended exclusive TV contract with ESPN/ABC. Even if he could come up with a better plan, even if he could think of a way to get more races on a broadcast network, he's stuck.
He has discovered that where he used to sign on with arena owners who sold tickets to the rodeos, he now has to deal with the two largest owners of motorsports facilities in the world who do not need his races to be successful or he has to deal with independent promoters, good and bad, who have to make deals with cities to use their streets and some of them are team owners. He has found races in other countries to be profitable for the series and wants to add more but now has the experience of getting shafted on what he thought was a done deal.
He has found that dealing with cowboys and their agents and the bulls and their owners was much easier than going toe to toe with Roger Penske and Chip Ganassi leading the team owners. He also has to deal with global companies like General Motors, Honda, Dallara, Firestone and a slew of other suppliers. He also has the drivers and their agents as well as their sponsors, the sponsors of all the tracks and promoters. As well as IZOD and other sponsors of INDYCAR coming and going.
He has found that venues that the fans, competitors and media believe are good for the sport don't want to be a part of the sport without a better deal. He can't charge them less to make them happy because that means less revenue for the series which makes his employers unhappy. He listened when many said the series needed new cars but car builders said they needed to be the lone supplier to meet the enforced price limits. So the new car costs less to buy but in order for the manufacturer to make a profit at the low new car price he had to agree to much higher replacement part prices. Which ended up making the team owners unhappy.
He has found a very small and sympathetic media covering his sport. While not universal he gets (HONESTLY) very little criticism from the regular media coverage and is able to get his message out as he desires. If he gets criticized on sports talk radio, it's only in one city in the USA unfortunately if the sport gets talked about on sports talk radio on a weekly basis it's only in one city in the USA.
So tell me with all that, is it so out of the question that he regrets getting into a situation where his ability to make things happen is in so many ways beyond his control and he ends up not wanting to continue?