Uptown Bourgeois is an art space for the creative works of freelance writer, editor, author, and content creator Jefferey Spivey.
Podcast: Failure + Female R&B Stars

Podcast: Failure + Female R&B Stars


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You’re listening to the Uptown Bourgeois podcast.

I’m your host, Jefferey Spivey.

Let’s be weird, snobby, and intellectual together.


This week, I want to talk about failure.

That was Barbara Corcoran, businesswoman, Shark Tank investor, real estate commentator.  She has an estimated net worth of $80 million and is often associated with success.  Which makes that clip all the more inspiring.  That excerpt was from a 2013 TED Talk at New York’s Barnard College. And there, she spoke so candidly about the motivation behind her success and some of her greatest failures.

Failure happens to everyone. To business moguls like Barbara Corcoran.  To our heroes and our foes.  To our friends, family, and co-workers.  And of course in our own lives.  As a freelance writer, I feel especially predisposed to failure.  I don’t have the safety net of an annual salary or the backing of a corporation.  So, when a project falls through or an idea doesn’t stick, I feel the financial, and emotional, ramifications almost immediately.

Experiencing failure is inevitable.  Regardless of how talented or supported or knowledgeable you are, shit just goes wrong sometimes.  It’s what you learn from that failure, and what you do afterward, that makes you a better person.

William S. Burroughs shared a lot of truth there in less than two minutes.  It’s crazy to think that a lot of the people we look up to go through the same experiences in their creative process.  Bad first drafts, ideas that lose their luster over time, pieces that no one else understands.  Really, writing, and any creative art for that matter, involves a lot of failing. It starts at a personal level before you even share your creations.  And it continues once others get their eyes on it.  Time and time again, we fall down in our attempt to create a great piece of art. And it sucks.

But what happens on the other end is something magnificent—a great story.  Or a great think piece.  Or a great painting.  Or a great song.  The more we fail at making something, the better the final product becomes.

And though I’m approaching this from a personal standpoint as a creative, this really applies to everything.  It could be an email you’re sending or a letter you’re writing to your dad or a room you’re decorating in your house.  You might have to keep trying, and you might keep failing, but there’s so much value in what you learn along the way.

That was Elizabeth Gilbert, you probably know her as the author of Eat, Pray, Love, but you should know her as the author of Big Magic,an excellent book about creative living.  What she talks about here is so profound.  About returning home to writing, and about loving writing more than hating failing at it.  

Perhaps that’s what’s ultimately important.  Failure sucks, even when you love something.  But you keep coming back because your love for your art far outweighs the disappointment or the fear you experience when you fail.  

In my personal journey, I think this rings true.  I wrote my first novel when I was 19 years old. I shopped it to agents until I got my first round of rejections.  Then, I stopped.  But that book idea nagged at me for years.  Then, 12 years later, I pulled out that dusty manuscript and started rewriting it.  And now, a literary agent is reading the first 3 chapters of that new manuscript as we speak.  I keep getting pulled back to writing because failure could never make me dislike storytelling.  

And for any of us to succeed at anything, we have to love it so much that failure is just a teacher for us and not a deterrent from our dreams.


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Each week, I publish one new essay or think piece; always personal, but always through a universal lens.

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To find out more, visit www.uptownbourgeois.com.


Just slightly switching gears, I want to talk about failure from a different POV. This week, Rolling Stone published a piece by Elias Leight about female R&B singers.  The lead-in was about Ella Mai and her song “Boo’d Up”, which currently sits at #11 on the Billboard Hot 100, and is leading a female R&B renaissance of sorts.

In the article, Leight revisits a lot of R&B singers’ careers in which they had brushes with mainstream success but longevity, or at least a full breakthrough, eluded them. It references Jhene Aiko, who released a successful EP in 2014, but failed to find the same level of success with her two subsequent releases.  It also broaches Tinashe’s career.  She had a hit with “2 On” but hasn’t had a Hot 100 hit since, despite a slew of singles, a mixtape, and proper second album.  

The article shines a light on how things are changing, and how a new crop of R&B hitmakers is on the rise.  But I want to talk about the failures for a moment.

One—success in this context is being defined as a high chart position or significant sales.  Not necessarily a creative peak or well-written song.  Two—failure, though never outright declared as such in this article, is defined as failing to match or best the performance of a previous project.

I find this interesting for a few reasons.  First, music success in general is something that’s shifting and changing every day. With streaming has come a lot of new tricks and strategies to chart, and also a lot of new definitions and metrics to deem a project successful.  So, in the case of someone like Jhene Aiko or Tinashe, who may not be topping the mainstream charts, it doesn’t mean that they’ve failed.  Perhaps they just haven’t mastered the new tools to game the system for streams.

Second, I’d much rather an artist push their art to a new level than chase trends to land a chart position.  If you can release a body of work that you’re proud of, and that your fans enjoy, then that could be considered a success regardless of the sales or streams.

In the case of Tinashe, her career stall might not have anything to do with trends in R&B.  

That was Zachary Campbell—if you’ve never watched one of his YouTube reactions or reviews, you are depriving yourself of life’s joys.

Perhaps with her latest record, the failure has nothing to do with the chart position and everything to do with the fans’ perception of her artistry.

And last, artists continuously experience failure, even after they’ve secured record deals or landed hit songs on the charts.  We all go through this process at all levels of our careers.  Success does not make us immune.  It just teaches us to look for the lessons in our failures and use them to turn things around next time.


New on the blog this week, read the companion piece to this episode, titled “A Brief Meditation on Failure”.  

Thanks so much for listening to the Uptown Bourgeois podcast.  Check back for new episodes every week, and subscribe on iTunes, SoundCloud, Google Play, Stitcher, Overcast, PocketCast, and now iHeartRadio so you never miss out.  If you love it, share it with your friends.  If not, shoot me an email at jefferey@uptownbourgeois.com and let me know what you’d like me to talk about.  Until next week…

The Uptown Bourgeois podcast is written, produced, and edited by Jefferey Spivey, and is an official property of Uptown Bourgeois, LLC.  All original music is provided courtesy of RMVD.

Bourgeois Brief: The Weeknd Launches Creative Incubator for Toronto Artists, Common Helps Starbucks with Racial Bias Training, Nijla Mu’min Joins Queen Sugar Directorial Team & More!

Bourgeois Brief: The Weeknd Launches Creative Incubator for Toronto Artists, Common Helps Starbucks with Racial Bias Training, Nijla Mu’min Joins Queen Sugar Directorial Team & More!

A Brief Meditation on Failure

A Brief Meditation on Failure