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It’s around 11 p.m. on a Tuesday night when I decide to ring singer-songwriter Ananda Sen, an unusual time for an interview. But I’m not worried about calling too late because an email from him has just popped up and reads, “I’ll be up really late tonight so you can call me anytime at 1-800-I-can’t-believe-I-committed-to-doing-a-song-every-week-what-was-I-thinking.”

On this particular night, Ananda’s mind is clouded by a combination of writer’s block, deadlines, and a bit of sleep deprivation. And sleep isn’t in the near future. If anything, Ananda’s night is just getting started. “I have my friends who play piano and bass coming in tomorrow to record,” he explains. “So I’m going to be up all night writing this song.” After pausing briefly, Ananda sheepishly admits, “I actually have no idea what I am going to write about.”

We decide to speak again on Thursday, and though Ananda is as friendly and charismatic as before, I can trace the fatigue hanging behind his every word. When asked if he’s feeling tired, he responds, “I actually haven’t slept in 36 hours because I was recording all last night. Between the time I talked to you on Tuesday and yesterday evening, three different songs were in incubation [in my head], and by midnight, I forced myself to just choose one.”

That’s the second all-nighter Ananda has pulled in three days. But to anyone familiar with the lifestyle of a musician, perpetual writer’s block and late-night (rather, all-night) recording sessions are nothing out of the ordinary. Then again, these all-nighters aren’t a one (two or three) time deal. In June 2007, Ananda pledged to write, record, produce, and post one free MP3 song on his website (www.anandamusic.com ), every week, for 52 weeks straight.

The first week of September marks the beginning of just week ten, and the enormity of Ananda’s undertaking is clear.

But Ananda is determined to defy the skeptics: “It’s amazing what you can pull off when you set a seemingly unrealistic goal. Everybody thought it would be kind of a disaster, so that made me want to do this more.”

“Everybody” doesn’t just refer to friends and family; it includes a wealth of well-respected professionals, artists, record producers, entertainers, and entrepreneurs. Though Ananda may be an unknown to most music listeners, he’s no stranger to the music industry.

Born into “a very musical” family and raised in New Jersey, Ananda starting his singing career at the early age of three—singing and playing tabla alongside his older sister on stage. Chuckling lightly, Ananda knowingly points out, “We’re Bengali, so we sing and dance and do all those artsy things.”

Ananda dazzled audiences at talent shows and school choir performances. While honing his fondness for classic rock music, he became the lead singer of a few bands in high school, a transition his parents weren’t particularly “thrilled” about. But Ananda eventually gave up rock bands and headed to the University of Pennsylvania, where his vocal training and knack for musical arrangement made him an essential asset to campus a capella groups.

“My sophomore year, a bunch of guys wanted to start an a capella group, but quickly realized that they didn’t really know anything about music,” he remembers. “So they approached me to help them out, and I ended up re-auditioning everybody, arranging the music, and teaching them how to sing.”

Penn Masala, the world’s first Hindi a capella group, was born that year, with Ananda serving as the Music Director. Together, the founding members established the framework for what would evolve into one of the most popular musical groups in the South Asian diaspora.

It’s easy to detect Ananda’s modesty, as he bashfully grazes over the professional and academic achievements most people would boast about: a B.A. from the University of Pennsylvania, a J.D. from Stanford University, and jobs in radio promotion and law with major as well as independent record companies (Capitol, Hollywood, and Century Media). Ananda had even started his own record company with his former Capitol Records boss, putting out two albums, before eventually calling it quits.

He explains, “Traditionally, lawyers have been pretty influential in the music industry, so I figured getting my law degree would help me start a record company.”

On paper, Ananda has achieved all the professional goals he has pursued, but on the inside, something has always felt missing. “I was pursing all these careers that side-stepped what I really wanted to do,” he reflects. It was shortly after this realization that Ananda decided to quit his job as general counsel at an independent record label to pursue music full time.

Though originally a vocalist, Ananda has evolved into a multi-faceted, multi-talented musician whose reach ranges from playing a handful of instruments (“tabla, keyboard, guitar, whatever I could get my hands on”), to writing and producing all his own music (“I spend all my disposable income on recording equipment”), to learning all the necessary engineering and technology (“I sat for literally six hours last Sunday reading music software manuals”).

Citing musical influences like Sting and Led Zeppelin, Ananda’s music is an eclectic blend of worldly influences, combining beats and rhythms from various regions of the world with his soulful, soothing voice. Some songs are slow and emotional ballads, like “This Unknown.” Others songs have a more reggae feel, like Week Three’s “Haunting You,” or even a Latin flair like Week One’s “Overthrown.” In “Set Me Free” (off Ananda’s debut EP), Ananda melds the influences of East and West by using hypnotic bhangra beats to compliment a fast-paced, upbeat melody. And yet while Ananda’s music is versatile enough to jump from one genre to the next, his songwriting and voice stay consistent and complementary to one another (even when he sings a few lines, impromptu style, during the interview). His lyrics are comprised of versatile, deeply insightful verses, and complex rhyme schemes. But above all else, when Ananda sings, his sound is so natural and soul-felt that you can’t help but wonder how he ever considered pursuing any other profession.

“One day, you wake up, and it all just seems so simple,” Ananda confesses. “I had built my entire life around music—I spent thousands of dollars on recording software and equipment and musical instruments for making my own music. So at some point, I asked myself, ‘So, is this a hobby or a profession?’ Because if a hobby consumes all your time and money—then is it still just a hobby?”

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The answer seems self-explanatory. Ananda’s philosophical realization triggered a whirlwind of events, which included quitting his job and shooting two music videos. “I figured,” he says, “if I’m going to actually do this, then why not go at it in a spectacular and all-consuming way.”

And by spectacular, Ananda isn’t referring to all the glitz and glam that most star-studded musicians dream about; he’s talking about his commitment to write and record one song a week for one entire year-a completely innovative approach to making music these days. “This whole thing doesn’t really make any sense because I’m not making any money off of it,” he explains from a very practical standpoint. His motives are simple and straightforward. Ananda wants to establish a connection with listeners and doesn’t believe that the traditional route of putting a CD out every two years can do so.

“It’s boring to have a website that says, ‘come back next week for a new tour date or screensaver to download.’ A website should have something new for the listener every week, like a television show,” outlines Ananda.

Inadvertently, Ananda’s music venture reflects “the real-time phenomena” of today: from blogs to instant messaging, reality television to webcams. Now you can add weekly music downloads to that list. While most artists rewrite and rehearse until they have recorded a perfect song, Ananda only has seven days. “A week is just about enough time to write and record a “studio-quality” song,” says Ananda. “I haven’t pre-recorded any songs, so I don’t have any buffer, and each week I’m putting together the song for that week itself.”

In essence, Ananda is demystifying the music-making process by making his songwriting and producing almost completely transparent for the listener. If he’s sick one week, his voice may not be as strong. Or if he has a lot of shows another week, the song for that week may have to be simpler and stripped-down as a result of his having had less time to write and record. By frequently blogging about website additions such as a new music videos or posted lyrics, Ananda is baring all for his listeners.

When asked about what fans have been saying, he mentions a message that a 17-year-old girl sent to him on MySpace. Given the nature of MySpace, I’m expecting this girl to be a typical musician’s “groupie,” charmed by his soulful voice and acute, boyish good looks.

But of course, Ananda is more down-to-earth than your typical star-studded musician. He makes no mention of his female fan following, which is obvious from the comments on his MySpace page, and instead goes on to explain that the young girl is the sister-in-law of Vinay Chakravathy, a 28-year-old South Asian doctor suffering from leukemia. In the message, she expresses her utmost gratitude to Ananda, who wrote “This Unknown” specifically for Vinay.

While the ride through the 52-week venture will undoubtedly be shaky, emotional, and challenging, Ananda is showing no signs of looking back. “It’s going to be a pretty exciting year, and I feel like the songs will just get better and better as it progresses.”

“Now,” he adds, “I just have to figure out how to get some sleep.”

Rupa Dev is a recent graduate of the University of Illinois, Urbana-Champaign. She currently resides in the Bay Area.