The financial woes of celebrities and some of our favorite music artists being splashed across popular print publications, music websites and blogs is nothing new or groundbreaking. As a society, we get somewhat of a sick kick out of seeing these difficulties played out in the court of public opinion, as well as in the real courts. But there’s something especially stinging and cautionary about seeing one of the greatest voices of a generation in Lauryn Hill try to grapple with the reality of staring down potential financial ruin.

There was a time when Ms. Hill seemingly could do no wrong when it came to crafting timeless Hip Hop and R&B music. To a generation of music fans in the 1990s that experienced a vast collage of styles and genres in black music, from thugged-out East Coast Hip Hop to Teddy Riley-esque New Jack Swing, from coffee house Neo Soul to raunchy, sexualized R&B, Lauryn was a steadfast constant, but was always a surprise. She helped to helm some of the music of the era that is most recognizable and most loved and respected.

From songs with a Pan-African, Caribbean twist and influence that introduced us to musical heroes of the past (“Fu-Gee-La”, “Turn Your Lights Down Low”) to those that made us believe wholeheartedly that we could upset the system and change the world (“Everything is Everything”), to R&B concoctions that gave inadvertent relationship advice that young women would listen to for hours on end in their college dorm rooms (“The Sweetest Thing”, “Ex-Factor”, “Killing Me Softly”), our Lauryn was untouchable. She was a super woman with a mic, a voice and a flow that could move mountains with a simple inflection and transition in her tone.

But eventually, it seems that what happens to all of us eventually happened to Lauryn too: life. Between the peak of her musical success with The Mis-education of Lauryn Hill and the release of her MTV Unplugged album, Lauryn seemed to suffer a pretty public yet carefully concealed breakdown. And between birthing six children, a relationship with Reggae royalty Rohan Marley that was long rumored to be abusive on many levels, the back-and-forth, on again off again drama between herself, Wyclef and Pras, several failed attempts at a Fugees reunion, continuous erratic and disturbing behavior in her few and far between public performance, and even fans learning of her long time affair with Wyclef, the years would go by and Lauryn would become more of a mere mortal with each passing day.

But as of late, Lauryn’s biggest challenge has seemed to come in the form of Uncle Sam knocking incessantly at her door and coming to collect. Earlier this week, it was reported from several news outlets that Hill just narrowly avoided potential jail time on charges of tax evasion. In 2012, Hill pleaded guilty to not paying federal taxes on $1.8 million earned in 2005, 2006 and 2007. At that time, her attorney said she would pay restitution at the time of her sentencing. It was revealed Monday in court that Hill has paid $50,000 of a total of $554,000.

Hill was originally scheduled to be sentenced on April 22 after pleading guilty, but has been given two weeks by U.S. Magistrate Judge Madeline Cox Arleo in order to make restitution, with the new date of sentencing set for May 3. Hill has claimed that her reasoning for not paying said federal taxes is from having to go into solitude due to threats made against her family, to protect her children and, from a statement made by the entertainer on her Tumblr page, to avoid “being manipulated and controlled by a media protected military industrial complex with a completely different agenda.”

At this point, Lauryn Hill’s story is equal parts history lesson, cautionary tale and cliffhanger/mysterious thriller. But the most important thing that we should take away from Hill’s example may very well be financial literacy case study. The truth is that we don’t know why Lauryn Hill avoided paying her taxes, and it’s truly not any of our business. If she had to go underground to protect her children, then that’s what she had to do. Or, if she’s just a former music star that didn’t feel the need to give the government, it’s supposed slice of the pie, that’s her prerogative, as well. But too many times we’ve seen artists and musicians with just as much talent as Hill that have had to go through a similar set of circumstances and have had to pay the price, no pun intended.

To some, this might just be a case of an irresponsible artist getting her just due. And to others, this is probably pretty painful and saddening to watch, knowing that Hill was such a musical beacon of light for so many of us at one point. But regardless of who you are, where you come from or what your opinion is on this situation, Lauryn’s example should give you these takeaways: handle your business, have your house in order and know where your affairs stand. Otherwise, you really could be singing the blues…and I don’t mean on stage in front of a capacity crowd.

Ron Grant is a freelance journalist and blogger originally from Detroit and currently residing in Orlando. He is a contributor at HipHopDX.com, is the lead writer for Orlando-based indie music label Conscious Mind Records and runs his own independent music blog, The Music Nerdvocate. Follow him on Twitter @RonGreezy.