1. Make sure his heart is in it. These races aren’t for the fainthearted and he’ll have to decide if he really wants to make a run, which may effectively bump fellow Florida Republican Marco Rubio from the race.
2. Make sure his family is up for this. The candidate’s entire family — and especially his spouse — have to be willing to endure a lot, and, in this case, give up the luxury of a relatively private life.
3. Figure out how to handle his brother’s legacy, which is looking a lot better than it did when George W Bush first left office. Jeb is not going to able to brush it off with “I’m my own man.” So, he will need to figure out how to embrace some parts of his brother’s legacy and leave aside others without ruining the extended family Thanksgiving dinner.
4. Remind voters how conservative his administration was and what he accomplished in Florida.
5. Explain his K-12 education reforms on his terms. “Common core,” a project he supports to raise national school standards, has been misrepresented and distorted by many on the right, but actual voters know little about it. He can begin to set the record straight.
6. Figure out how to deal with the anti-immigration-reform right. Can he win without them? Does he need to figure out how to make peace? Ironically, his book that advocated a path to legalization without citizenship is now where the right wing is.
7. Get a team that is accustomed to the new 24/7/social media universe. The media environment is nothing like it was when he was governor, and he’ll need a top-notch team to help him figure out the 1,000 news-cycles a day atmosphere.
8. Don’t make the Rudy Giuliani mistake of waiting for the Florida primary. Bush will be expected to win that; moreover, he will need to make sure he’s in the top tier of candidates before the race gets to the sunshine state. That means a lot of visits to Iowa and New Hampshire and constructing a network of supporters.
9. Take his education reform message to higher ed. If he can show how to slay the student loan behemoth, attacks college price gouging and supports alternative credentialing programs, he’ll become a rock star with youth voters and their debt-laden parents (or grandparents).
10. Be the environmentally friendly advocate of domestic energy production. Bush protected the Everglades but has remained a supporter of energy independence and safe energy development. That is an appealing combination in the general election and with younger voters.