Skipworth, 25, was delisted by Adelaide two years ago after 44 senior games and six years at the club.
He entered the 2007 NAB AFL National and Pre-season Drafts, but failed to attract the attention of any of the 16 clubs. So when an opportunity with the VFL side Bendigo Bombers arose, he decided to take it.
"I saw an opportunity through Matty [Knights] and Sheeds [Kevin Sheedy] to come over and train with Essendon, and I thought that was going to be my best avenue back into the AFL," Skipworth said on Tuesday, after Essendon claimed him with the third selection in pre-season draft.
"I made the move away from friends and family and my girlfriend and came over, and I initially was going to give it a crack for a year and I ended up doing my knee and had to sit the year out.
"I thought, I can't leave on that note, so I gave it another year and it's worked out well."
Knights, who coached Skipworth for the first year he had with Bendigo, recently had the pleasure of telling the former Crow he was about to be handed another chance in the big time.
"I've been rapt the last few days. I've known for a few days now, my family as well," Skipworth said.
"It's been a roller-coaster ride so far. I've experienced everything and I'm just glad to get another opportunity with Essendon.
Knights said Skipworth was a perfect fit for the mid-age player bracket of 23-28 years that the Bombers lacked, and would be an asset after showing his willingness to work with the club's youngsters.
"Hayden is a great fit both from a playing perspective, and also with his development and mentoring with the younger players; it's nothing short of sensational," he said.
"This has just been while he's been on the Bendigo Bombers list, and that says a lot about a person."
Skipworth said he was already entrenched within the Bombers' ranks, having lived and worked with some of the players.
"I had David Myers, Tayte Pears and Kyle Reimers live with me in the Samsung club house last year, so those boys I've had my eye over all year and have tried to fast-track their development and help them become regular footballers," he said.
"I've also worked a lot with Scott Gumbleton. He's had an unlucky run so far but he looks like he's on the right track."
What for many would be a daunting task has not proved so for Skipworth, who said his AFL comeback was made possible by his undying passion for the game.
"I guess it's not hard work when you really love something, and I haven't seen it as hard work as all," he said.
"I just really wanted to play some more AFL games."
