His previous bands, The Little Flames and The Rascals, didn't make it past the first album before he left both.
And his side-project with Arctic Monkeys front man Alex Turner, the Last Shadow Puppets, only released one album as well.
But now the singer-songwriter is on course for his second solo record – and he'll debut new songs at Barrowland next week.
"It's looking like it'll be an upbeat record and I can't see that changing," he says.
"There's a few tracks in the bag already, and hopefully after the tour we'll go in and record them, and try them out.
"I'm just excited for the next record, it's going to be really strong. I don't want to jinx it, but hopefully it'll be out by the end of this year.
"It just feels so right, and I've felt so comfortable in my life, really. I don't want to stop this – I don't want to do anything else as I love this so much."
Miles was recently quoted as saying he'd love to work with American singer Janelle Monae if the chance arose. But for the upcoming recording sessions he's pulled in a bigger name to collaborate with, in the form of the Modfather himself, Paul Weller.
"Me and Weller are going to try some bitsthis month, and we'll see what happens there," he says.
"We are just going to try a couple of days in the studio and see what happens – it may not work out but hopefully it does, and it'll be great. Sonik Kicks [Weller's new album] is great, I love the song The Attic on it.
"I get inspired by him without a doubt."
After years of trying to make it with various acts, and becoming best-known for being pals with Alex, the past year has seen Miles start to step into the spotlight in his own right.
His debut album Colour of the Trap's relentless barrage of anthemic guitar-driven tunes won him many fans, helped by his commitment to non-stop gigging.
Now he's set to play to a sold-out Barrowland, on April 21, in his biggest gig yet.
The Scouse singer feels that these size of shows are something he's gradually built up to over the past several months.
"Every week or day or month has been a gradual step," he says.
"When we started playing the songs off the first record it was to 150 people in clubs, and we've built it up and built it up just by getting better.
"People can relate to the songs, and they have really grown themselves, just as I have. It's a great place to be at, where we are now and I'm well up for it.
"Songs such as Come Closer have big choruses you can sing along to, and a lot of them on the first record can be like that live as they have got those chanty bits, even the ones that aren't singles."
The show coincides with the release of a one-off EP, called First of My Kind, that's being released for Record Store Day, in which Miles also tackles Tom Jones's early track Looking Out My Window.
"If anyone has never heard that Tom Jones track then they should, as it's amazing," he says. "I think we'll be playing that on the tour, and it's rocking. I love Jones' early stuff, he's great. He's very cool."
But that's not the strangest thing Miles has been involved in recently, after he ended up playing royalty at a charity event in Monaco, called the Rose Ball.
"It was quite a strange one," he chuckles.
"We'd been asked to play by a princess in Monaco. The theme of the party was the swinging 60s and it was all for charity.
"Who better than us to play that! It was fun – we had a ball."
l Miles Kane, Barrowland, Saturday April 21, sold out, 7pm