There’s an idea that the longer you work at something, the easier it gets. In many ways, that’s true. The technical knowledge–from how to play guitar to how to structure a sentence–become engrained in the mind after years of repetition and practice. The basic rules are sorted out and memorized, and they’re not quickly forgotten. At the same time, there are many aspects of doing the same line of work for years that don’t get easier, and require concentrated effort no matter how long you’ve been doing it. Industry standards and strategies change with the introduction of new technology and trends, requiring people to keep up if they want to thrive. In creative fields, burnout must be avoided at the same time as artists examine themselves and the world around them in search of new inspiration and ideas. It’s not for the faint of heart, which makes the longevity of Hoodie Allen and his creative success all the more impressive. Over nearly ten years and numerous mixtapes and albums, Allen (Steven Markowitz) has constantly pushed himself to experiment with new sounds, connect on a real level with his fans, and keep going strong. With the recent release of his new album Whatever USA, Hoodie Allen has proven he still has the drive and the talent to make it all happen.

A new album and a busy press schedule means very few days off, even including your birthday. Allen and I talk on the phone the Monday after Whatever USA drops, which also happens to be his 31st birthday. He’s in the car after doing a live-streamed performance for Billboard, and acknowledges with a chuckle it’s not your standard birthday. “They were like ‘It’s our first time ever having someone on their birthday’ [and] I’m like ‘that makes sense, I can see that being a rarity,'” he says. Still, the ebb and flow of album promotion is something he welcomes after the long writing process.

That writing process resulted in something not quite like anything Allen has put out in the past. Whatever USA is still a Hoodie Allen album, brimming with energy and confidence in the lyrics and performance and mixing live instrumentation with captivating beats in the music. But there’s a distinctive feel to it that sets it apart. It leans farther into the acoustic side of things than anything since Allen’s Americoustic EP in 2013, and finds him looking inward more frequently and pointedly than something like his 2017 album The Hype. Songs like “Hometown Kid” and “IDK WHY” see him not only express a universal search for our place in things that crosses every young person’s mind all across the country, but examining his own place in life in a movingly open fashion. Whatever USA is not just a reflection on Americana themes of self-discovery, exploration, and nostalgia, but a deeply insightful look into Allen’s mind as he grapples with those same concepts on a personal level.

That the album contains such a strong theme is a testament to Allen’s writing, especially considering the central theme of the project came relatively late in the process. Of the theme, he says “That kinda formed with the title track, when I made that, which was earlier this year in January. Before then I had been working and writing and recording a lot of songs and it was a little bit more of a mixtape in the sense that there wasn’t any cohesion really.” After writing “Whatever USA,” he ended up scrapping or reworking much of the material he had, which he says he’s glad he ended up doing. He also explains that waiting for a theme is something he enjoys while writing because it allows him to better capture what he’s feeling and experience in those moments. “Your own life experiences inform a lot of the things you feel and that you want to write about in the moment. For me, I came to it, and when I did I felt very happy that I had waited to conceptualize it all,” he says.

The personal nature of Whatever USA is something Allen definitely sees as an asset, and something he works hard to present in his music, even while collaborating with producers or album guests like Christian French. He explains it’s a balance between getting new input and still maintaining a core vision across these partnerships. He says, “I think that’s why it’s important to collaborate production-wise and feature-wise with like-minded people who you think also have something cool to say.” Allen has never been one to put on an act or public persona as a celebrity. The person you hear in the music is the same person you talk to when you meet him and the same person who still goofs around on Twitter with fans. When it comes to being the real him at all times, Allen says “I think that’s what has allowed this process to be so fun and the reactions I’ve gotten so far are so great because I do think people are resonating with it on a personal level.” This is especially admirable in 2019 and the era of overwhelming social media access, which he agrees can often create pressure for artists to create a seperate public image for fans.

The pressures of the industry have also changed rapidly over the years, especially for independent artists like Allen. “The way people consume music just over the last decade or half-decade has continued to change almost on an every two year basis,” he reflects. While labels have infrastructure in place to make some of these pivots, Allen explains independent artists have to be quicker on their feet, citing the shift in focus from album sales to streaming numbers as an example of how artists have to adapt. While it does create added pressure, he’s not backing down from it. “I like it though. I think it’s a really interesting challenge, and you gotta be able to keep up and move with the business side of things as well as the creative,” he says. In fact, the business side of music is something he has an eye on in the future when he retires from recording (which is not anytime soon, don’t worry). “I envision one day when I feel like I no longer have something to say that’s worthwhile to put on record that I would like to be one of the creative leaders in this sort of business,” he muses, explaining that he wants to help artists like him carve their own path just like he has done.

The pressures of the business and social sides of music aren’t the only pressures Allen feels. In the lead-up to the album, he often described this project as a rediscovery of himself, which he partially attributes the need for to the rigors of being an independent artist. Allen knows this better than most, having been independent through his entire career. “I always feel this sort of innate pressure that I don’t know, maybe a lot of artists feel it. But I always feel like every album is a make or break thing,” he explains. He elaborates that he’s always thinking about the time a person takes out of their life to listen to his music, and how each time someone listens, it might be the last time they check him out if they don’t like what they hear. He calls this a “huge amount of responsibility,” and from the weight in his voice as he explains this, it’s clear he doesn’t take it lightly. “I always keep that level of pressure on myself in order to try to make the best stuff that if I did have one chance, that I would make the most of it,” he reflects.

The other part of the rediscovery came from a realization Allen had while writing what would become Whatever USA. Speaking about the personal nature of the music, he recalls “I think I had lost a little bit of that early on writing, I felt like I would listen back to some of the songs I was doing and I was like ‘oh..’ I was referring to them by other artist’s names. I’d be like ‘This is like the Brendon Urie song. This is the Juice WRLD song.'” While he has nothing against those artists, he says the last thing he wanted is to have someone think of another artist as their first reaction to his music, instead wanting to remain entirely his own person and artist. Again pointing to how much content we’re flooded with when we look at our phones, Allen says there’s often an urge to categorize artists into certain boxes as shorthand, and is proud of his success on pushing back on that. “I think that for me still being able to do it, still having so many people who are invested and interested in me, it’s a validation of there’s a lot more than placing a label on something if you really listen to the records,” he says.

What also stands out about Allen when he talks about his music is both the respect and trust he has in his fanbase to follow his thought process and grasp the music he’s making, and his desire to make something that will be meaningful to them. As an example, he brings up how listeners have different “ears.” He explains “Some people listen and they’re listening for flow, they’re listening for lyrics, and other people are like ‘does this pass the beat test? What’s the beat sound like to me?'” On Whatever USA, he says he wanted to keep the album condensed to its nine song length in order to make sure it was strong no matter how someone approaches it. He also keeps this in mind when figuring out the art, marketing, and surrounding materials for an album. “How can we match it and elevate it to make it something that people will feel is iconic in a sense? That they’ll want to keep and have with them five years down the line, ten years down the line. Not just ‘that was really cool’ for three months,” he says.

In September, Hoodie Allen will begin the North American portion of Phase One of the Whatever USA Tour, something he was keenly aware of when making the album. He explains he doesn’t consciously write towards having cool live moments, but will try to identify them once he has a project written. That said, he is excited about what’s to come on this tour. He says “You can find out when you start practicing–like I’ve started band practice right now–and we’re starting to figure out wow, we’re really gonna be able to transform this live, it’s gonna be really cool.” All of his touring experience feeds back into the personal thesis found on the album. “There’s been this running theme, which is kinda funny because I do live in New York, but I feel so connected to the Midwest and these small towns all over,” he explains. He says seeing the reaction of fans throughout towns of all sizes drove him towards the homey theme of WHATEVER USA, citing the “big fish, small pond” message of “Hometown Kid” as a prime example. He’ll have a willing audience when he hits the road. As he tweeted gleefully when it happened, the album was streamed a million times in the first day, a fact that he says makes all of the hard work, anxiety, and stress worth it at the end of the day.

Over his nearly-decade long career as an independent artist, Hoodie Allen has adapted and grown while still maintaining the central core of emotional honesty and musical wit that fans so personally connect with. On Whatever USA, he’s continued to innovate with sound and subject matter while simultaneously delivering one of his most personal projects ever. Whether it’s on the business side or creatively, Allen has the knowledge, charm, and determination to extend his career as long as he’d like to. Wherever rediscovery takes Hoodie Allen next, it will be well worth taking the journey with him.