“I feel like it was very natural for me to talk about what self-love has been for me in the past few years,” Diggy Simmons says gently from the other side of the Atlantic. The 23-year-old rapper-singer is in Brooklyn “just hanging out” and professing insecurities to me as sensitively as an old friend. “Getting here — to the point of even making an album — I have been saying throughout this whole process it’s been an obstacle just to let go, to allow myself to enjoy what I do, not think about what critics would say.”

It’s been six and a half years since Simmons last released a body of work. “I wasn’t putting anything out because I was in my head so much,” he confesses, explaining the wait for his forthcoming, yet to be titled second record. His debut, 2012’s Unexpected Arrival, was laced with grandeur; listenable and catchy, it told exactly the kind of narrative you’d expect from a 17 year old. The son of Run DMC’s Joseph Simmons, his childhood was televised on MTV’s Run’s House and his adolescence existed in a strange place, somewhere between already being known as a kid and having to present himself to the world as a young adult. With a touch of braggadocio, Unexpected Arrival was an album about wanting it; an album with something to prove.

“It became exhausting and not a fun process,” Simmons sighs. “I was hung up on ‘this has to be better’, or not doing the music because I wasn’t feeling the best about myself, I wasn’t feeling good enough. A lot was holding me back and a lot of that had to do with a lack of love that I had for myself for many reasons… That’s been one of the obstacles on the way to this album, allowing myself to let go and put my best effort forward no matter what the result may be. For a lot of people my age, that’s an obstacle I see often.”

His return to music is a joyous celebration of finally being comfortable in himself. Released in August, single “It Is What It Is” has become Simmons’ “perfect mission statement”, a mantra to remind himself and his listeners that being yourself is enough; a modern iteration of “Que Sera Sera”. Cinematic and warm, the track swells with strings and gospel-lite harmonies while his voice carries itself with so much understated confidence and maturity, the teenager from his debut LP is all but vanished. “I feel like there’s still pressure,” he readily admits. “I always say just because I made the album, it’s not like all these [insecurities] have gone away… It does feel like a big feat for me because I’ve gotten out of my old ways and it feels so good to say that I have music, I stopped over-thinking that process.”

Recorded in California at the start of the year, Simmons completed the album — due for release this October — in just four short months. “I didn’t necessarily have the expectations of a full project being completed,” he insists, “I was more so just excited to make music again, it always feels so good. A full album came out of it from January to May… I think we just got a great tempo over time, we had a clear vision of what it was that we wanted to accomplish with it and didn’t get sidetracked.” Ploughing his own life for lyrics surely aided the fast turnaround, from faked pregnancies to the perils of social media pressure, the record’s an autobiographical insight to Simmons’ last six years away.

“My favourite rappers have had some of the greatest personal stories in their raps,” he reasons, “I always enjoy it when I hear them do that, so it always feels right to express myself in that way… I feel like I’ve always been vulnerable, that’s always what my music has been… But compared to my last project when I was 17, at 23 you’re a completely different person. I’ve been through way more, I’ve felt way more than I did at that age. So it has been a little more nerve-wracking being like, ‘Wow, I’m about to share a lot.’ But I feel like I’ve got more comfortable with it.” Now, Simmons’ music is serving the same purpose as his heroes’ — the likes of Kanye, Jay Z and Nas — did for him. “People normalised the things that I’m talking about by telling me, ‘I relate so much.’ That’s the most fulfilling part about making the music that I’ve made – the messages I’ve had. It helps, and it’s the most awesome feeling.”

That’s what he’s cultivating, a sonic safe space of acceptance, to help both himself and his audience realise flaws and trials are universal. “I hope people are able to relate,” Simmons concludes, “and it’ll allow them to get through certain things… There’s so many different layers, it’s a life album. That’s what we are as people, we’re never one way all the time, we have this array of emotions. On one song I can be completely cocky and boastful, all into myself, and on another song I can be doubting myself and unsure. That’s what life is.”

Taken from the Autumn 2018 issue; out now and available to buy here.