Madonna: Resilient AF

The Queen of Pop is a master of coming back stronger no matter what Life throws her way. Inspired by her live performance, I'm diving in to show how she models thriving in business and art.

This newsletter is coming into your inbox later than it usually does because I unexpectedly went into a research rabbit hole and got very into learning just how distinguished our fair queen is. I hope you enjoy reading this as much as I enjoyed writing it.

First, Some Backstory

Did you see that some concertgoers are suing Madonna because she started her show late? Yes, she took the stage two hours later than when audiences thought she’d start. And yeah, a 10:30pm start time is considered extreme here in the States. But, so what? I was one of those concertgoers, seeing the second night of her Celebration tour in DC. Now, mind you, I didn’t *want* to attend a concert that started at 10:30pm. And if you told me that ahead of time, I’m sure I would have passed. I’m a tired mom.

BUT.

I’m also a tired mom who has never seen Madonna. I’m a tired, 45-year old mom whose childhood was shaped by Madonna’s influence, and yet I have never seen her perform live (except her one-song GRAMMY Awards opener in 2006, while I was working for The Recording Academy. And it was awesome, click the link for a treat.).

So, in this case, I was thankful for what I didn’t know at the time of the ticket purchase—which, I’ll admit, involved a feverish text to one of my best friends to see if she wanted to go, all while I was eight months pregnant and living in a completely different state but was so excited that I would soon be in Northern Virginia, near my bestie again, and no longer pregnant and ready to have a full Madonna experience. Which, evidently, also means a late start time.

FWIW (and this is by no means the purpose of this newsletter, but a point that deserves some noting), in response to the concert attendees who are suing because they had to wait two hours sipping bad wine in the Barclays Center—which is the real crime here—I’m sure the concert organizers know that Madonna goes on late. There’s no hiding that. But it was the organizers and venues who weren’t going to put Madonna’s real start time on the tickets for fear of losing sales. I understand that from a business perspective. But also, maybe if they had, you’d have people organize their evenings like my friend and I did once we saw on Twitter/X that she was starting two hours later than expected. We enjoyed a longer dinner with drinks that were not 32oz Bud Lights or bad Chardonnay served in individual bottles.

And judging from the swarm that left the restaurant when we did to cross the street into DC’s Capital One Arena, making it there at exactly her actual start time (thank you, Twitter); others got the memo as well.

Because here’s the thing—from the moment she started singing, I was so glad to be there to behold what felt like a curated exhibit. Because what Madonna serves is art. Art, entertainment and moxie is the Nation of Madonna’s GDP.

She’s not “keeping people waiting” she’s starting exactly when she wants to start, which is 10:30 on the dot and she ended at exactly 12:30am. She’s a professional who works on real timelines and deadlines just like you and me. It just happens that when a world-class performer delivers a superior product, people are willing to bend their lame, suburban routines. (At least I was.)

That is talent mixed with star power, and this newsletter is here to honor that.

But Also!

And you may recall that last summer Madonna got a very serious bacterial infection that landed her in the ICU and postponed her tour. It turns out that it was likely life-threatening. And she came right back to her tour, driven as many performers are, to get back to work and serve her fans. This sixty-five year old was not deterred, even after a life-threatening, intensive care hospital stay.

Not only is she a model of someone who has taken setbacks and thrown them right back at life, her concert reminded me that she’s one of the biggest stars in the world (a merit she keeps earning decade after decade) with staying power that no one can argue. In a way I didn’t imagine, her performance elicited emotions and a few art-as-business observations. Here’s a reminder that:

• No one but Madonna is the Queen of Pop. And she’s earned her icon status over and over since the early 1980s.

• All current pop stars owe credit to Madonna for paving the way. (See the star-studded video at the bottom of this post with Beyonce, Diplo, Kanye, Katy Perry and more paying homage.)

• She’s created a long-lasting business by not playing it safe. She didn’t conform to public opinion: she led it. Very few people could push boundaries so boldly and also attain that level of mega stardom. We take for granted how she deftly negotiated a brazen public persona and mass public appeal. No one had done that. You could be niche and loved by a few or you could be generic to appeal to the masses. We see newer pop stars (Gaga) repeating this now, but there’s only one person who paved the way.

• A 65-year-old performer who simultaneously wears a knee brace and tassels on her nipples is a provocateur who trades in charisma of the rarest breed. (Sadly, I don’t have a picture with the tassels.)

Life/Business/Craft Lessons From Madonna

It’s an understatement to say that her performance in the Celebration tour was inspiring. I was bludgeoned with the fairy dust of her talent over and over again. I got unexpected chills when Like A Prayer started. I was dumbfounded when Live to Tell showed up on stage as an homage to AIDS victims (duh, I should have known that, but we certainly weren’t talking about that in 1986 when I was singing along to the tape as an eight-year-old.)

Over and over again, I was greeted with the favorites that shaped my childhood. (Shout out to my parents who had no objections when I purchased—and listened repeatedly—to the entire Erotica album. To this day it’s my favorite album. It’s a whole mood and if you aren’t well versed in it, do yourself the pleasure of listening track by track to this 1992 gem. I bought it for Fever. I stayed for Erotica, Deeper and Deeper, Bad Girl, Rain, Waiting, Bye Bye Baby, and basically every track. If you read the comments in the YouTube link above, you’ll see I’m not alone.)

Provocative, yes. Madonna has not stopped pushing the envelope. But behind the antics that distracted the media for years (and often still) is the talent, showmanship and work ethic that has sustained her effervescence.

As I marveled and enjoyed what felt both like an incredible art installation and a house party, a few lessons came through that I couldn’t ignore:

Develop your skills. At the beginning of the show, which was organized chronologically, she told the story of arriving in New York and learning to play guitar from a boyfriend, then taking the stage at CBGB. Of course is wasn’t that simple. (This 1984 Rolling Stone interview with Madonna is a fantastic chronicle of that era.) But one thing did lead to the other. It started with expanding her skills beyond dancing and her voice.

Tell your story and figure out how to make the world hear it. As she was learning guitar, she was also songwriting…which, by the way, no one really talks about. Madonna has written a whole catalog of songs, many of her own hits and others for other bands. She reflected what she saw and lived. “She grew up on Joni Mitchell and Motown and…embodies the best of both worlds,” says Rick Nowells, who co-wrote with Madonna on 1998’s Ray of Light. “She is a wonderful confessional songwriter, as well as being a superb hit chorus pop writer.” In fact, Rolling Stone named her #56 in their list of the 100 Best Songwriters of All Time. (By this time, I hope that anyone who minimizes her as merely a provocateur is starting to see that you don’t provoke and curate cultural discussion for almost half a century by being a flash in the pan. For a great trip down memory lane, check out Billboard’s list of her best songs. (You’ll See is a pure time capsule to 1995. And yes, while watching the video, I screen-shotted her hair and makeup for future reference.)

Face your fears; and for the love of god, just keep on going (aka: trust yourself). Like any confessional artist, you gotta do you. Tell your story, find the way for people to hear it and don’t back down.

Take. Yourself. Seriously. (Related: Don’t Be Afraid to Tell People to F*Off) Take yourself seriously is the alternate title of this newsletter. Because as a creator or artist or entrepreneur, this is what is required of you. It’s this conviction that stamped a Madonna-shaped impact on our culture (which allowed so many other women to chart their course to mega stardom).

But also, have fun. Let’s go back to that video of Madonna performing at the GRAMMYs. She’s singing, there are intense dance moves, but then you see it; she’s smiling. Same at her concert. Not to be ageist but I’ll say it again: SHE IS 65 YEARS OLD ON A WORLDWIDE TOUR, and clearly this woman isn’t doing it for money. (According to Wikipedia, she’s been the annual highest-paid musician three times and the annual highest-paid female musician a record eleven times.) She’s doing this, sure for the love and adoration from fans, but also, because she likes it. She’s enjoying herself. And here’s hoping all of us can create a life and an authentic 40-year career that makes us smile, even when we sweat.

See minutes 4:52 and 7:09 for an infectious smile I didn’t expect from Madonna.

The recent collab with Nicki Minaj and many other stars honoring her white hot North Star. …because, Bitch, I’m Madonna.

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PS: If you loved Madonna in A League of Their Own, and the movie in general, you may enjoy my friend

Erin Carlson

’s newsletter You’ve Got Mail and her book, No Crying in Baseball, the inside story of the movie that made that phrase famous.