Day, who came through the youth system at Arsenal before playing two years with Howe at Bournemouth, is assistant coach at Crawley under manager Scott Lindsey.
In this Q&A with Tribalfootball.com, Day discusses his influences and how the game has taken him across the world.
Jamie, you can through the famous Hale End academy at Arsenal - how big an impact did that education have on you?
"I think Arsenal was the best (experience) and most difficult one because it's a fantastic club that, from the age of 8, took really good care of me on and off the pitch developing me as a player and person and had great traditions and history to respect.
"But as I got older it became more difficult to break into the first team and in the end it became a frustrating place to be but I still have fantastic friends and memories."
As you mentioned, you were part of Arsenal right at the beginning of the Arsene Wenger revolution...
"Arsene Wenger changed the philosophy of Arsenal Football Club from food to training regimes, which benefited all players from young to old. His methods were different from English coaches, which was refreshing and certainly helped me in my coaching pathway."
After the Gunners, you left for Bournemouth - where you had Eddie Howe among your teammates. How was he as a player?
"Eddie was a very cultured centre back who was very comfortable in possession, but also showed an aggressive side to his defending. He was fairly quiet but always took an interest in coaching.
“I think he has done a really good job at Newcastle. It's always going to be difficult to catch the big 4, but he has brought stability and the club and fans closer together again.
"I believe he will manage England one day."
Going back to Dean Court, what do you make of Andoni Iraola's impact at Bournemouth?
"Iraola had a really good (last) season and showed the decision to bring him to the Premier League was the correct one. His knowledge has helped the club move forward.
"They're showing progression in the right direction and I think they have a great future in front of them.”
Arsenal, Bournemouth... but you also spent time in the non-leagues - has such different experiences helped your coaching?
"All these experiences, good and bad, have been a fantastic learning curve and ultimately made me a better coach. My objectives have always been to develop and create good people with hopefully winning games along the way."
And before you made a return to Crawley, that experience included a stint in charge of the Bangladesh national team...!
“It was an amazing experience working in different countries, learning new cultures, and working with new players and mentalities. Bangladesh has a strong football following that just needs to invest more money to help future development.
"I think some Asian countries want success but want the quick, easy route to it, not wanting to put foundations in and investing.
"But you can see the countries that have done that, like Japan, now reap the rewards."
Before we sign off, Jamie, what have you and those at Crawley made of the decision to scrap FA Cup replays this season?
"I think it's disappointing, especially for the non-league clubs, replays have always been a tradition in the FA Cup and should remain."