Sunday Music: The Tortoise's Path (Feat. Doechi, Westside Gunn, Questlove, Mike Birbiglia, And - My Own Anxieties)

We all know how the fable ends, “slow and steady wins the race.” In the creative/creators world, I'm increasingly convinced that the tortoise approach to artistry builds something more lasting than the hare's sprint to fame. I didn’t expect it to show up from 4 perspectives in the past week, but it did, and I wanted to share my current thoughts on building slow - because I know this will hit extra hard with my fellow Personal Archive authors out there.

It’s fall 2024, Doechii is just then but also finally “officially” blowing up (at least by my standards, which means I’m noticing how I’m getting emails/texts from all my music buddies asking “have you heard this NEW album from this NEW artist yet?”), and she shows up in my podcast feed with Ebro Darden. I’ve been impressed with her lyricism and her love for the hip hop of my youth, which is simultaneously forcing me to appreciate her but also wonder how much throwback I can handle without just going to the sources. I know she’s young, so I’m curious what she’ll say.

Probably unsurprisingly, Doechii tells Darden, "I've been into a lot of MF DOOM, OK, rest in peace… Yeah, I've been into a lot of MF DOOM, Westside Gunn. Love him. He's so talented. Super. So incredible."

Fact check: I’m impressed. It’s not just the Missy and Nicki and post-KRS without being Kendrick vocal range expansion kit I was expecting. She dropped DOOM, which felt obvious (plus, I’ve since seen her on Nardwuar), but - Westside Gunn too? You already know how I feel about Griselda (and DOOM).

Fast forward to April of 2025 when Jeff C., who is my favorite “I still listen to all the underground stuff” buddy, sends me a message with a one day old Westside Gunn song called “EGYPT.” I press play and - he sampled the Doechii interview mentioning him. I play it, I love it, it’s got this whole recursive artistic appreciation loop energy, executed flawlessly, and then I ask the obvious question -

“What did Doechii think???”

And she of course went a little crazy in the best ways, putting a message on X that you can read yourself because she says what to kiss and what to choke on in the most pro-social fist pump of getting shouted out by somebody you look up to way (with slightly more colorful language).

I’m taking all this in when I realize I’m still hung up on a few very particular details here. Doechii’s got to be like, 25, and Gunn’s got to be like 40, and, she’s talented, but is this too much success too fast? Is there any turning back to her because, while I’m sure Gunn wishes in a way he was more famous or successful, the reason Doechii is looking up to him (and DOOM) is because they can totally operate on their terms. She’s about to find out, probably the hard way, if that option is there for her.

Hello tortoise, hello hare, it’s your old friend Matt wondering about creative longevity again.

Down the rabbithole I go (which feels like I shoutout Dave Nadig too because now I’m stealing his entire show name and way of life).

Here’s the timelines. Doechii dropped her first SoundCloud tracks in 2016, established her foundation with a project in 2019, followed by a self-funded EP in 2020. One viral TikTok moment in 2021 accelerated things, leading to her Kendrick Lamar label signing in 2022. Singles and touring in 2023. The Alligator Bites mixtape explosion in 2024. She's 26 now, and while eight years isn't a lifetime, it wasn't overnight either.

Meanwhile, Westside Gunn started releasing music in 2005, took a five-year hiatus due to “personal” and “legal” issues, co-founded Griselda Records in 2012, and has been consistently building since. He's 42 now. Never had a Billboard hit. Never needed one.

And here's where it gets THE MOST INTERESTING – Doechii's biggest hit right now, "Anxiety," was actually recorded back in 2019. It's a song from before the machine got behind her, before the expectations, before the spotlight intensified. And, some corners of the internet are already turning on her precisely because she's "too big" now.

This was the moment I feared. When? Now. Yes, that’s a Slick Rick and Spaceballs mashup joke for you. I’m proud of it and caffeinated enough to make it.

As I’m processing what this all means, and listening to Westside Gunn’s 10-minute long EP Heels Have Eyes on repeat, I wake up one morning to take a break and put on a podcast, when Questlove on Mike Birbiglia’s Working It Out shows up top of my feed. The muse finds me. I look for her, but she always finds me.

Birbiglia tells Questlove, in a back and forth on the times in their journeys when they weren’t quite making it (at all!) and were feeling jealous or envious or both about the people around them who were, “The thing I realized about jealousy - if you want what someone else has, you can’t just one-for-one have what they have and be you at the same time.”

If you truly long for what someone else has - fame, status, money, career, whatever - you can’t just wave a magic wand and have it without also fundamentally changing yourself.

We’ve arrived at the heart of artistic anxiety. A young artist wants it all now. But what happens if you get it? This is the whole Sly Live’s! documentary that Questlove released (which is beyond exceptional by the way, and do pair it with Sly’s memoir which is one of my top 10 memoirs, easily).

Birbiglia and Questlove spend a minute talking about André 3000’s appearance in the documentary. He blew up young and fast and is doing the improvisational flute thing now, as you probably know. André explains the problem of early fame, and how you’re both giving and taking so much to and from the world when your success is happening, that as soon as it’s withdrawn, you don’t know where to put your energy or where to draw it from and it’s crippling.

The hare needs fuel. It needs a lot of it. And when it runs out, it’s got to take a nap, and we know what happens in the race when the hare is sleeping.

The tortoise’s path doesn’t require the same sourcing of success as fuel. Westside Gunn, Birbiglia, Questlove - they’re trying to teach us something totally different from their journey and the peers they’ve observed. The audience you get from sudden fame has ownership of their own expectations on you. And they have it in size. It changes your ability to move the need going forward, it changes the speed you feel like you’re supposed to operate at, it changes your ability to slow down and not have it feel like failure because… anxiety.

Gunn sees it too, and it’s even on the EP. On the song before “EGYPT”, on “DAVEY BOY SMITH”, there’s an extended outro where he’s just talking. He brags about making a tape in a single night while "your favorite rapper ain't dropped s*** in how long?" Then he winds up even harder and throws out, "I don't even like to rap, that's the thing about it. I'm not a rapper. See, y'all like rappers. I'm an artiste. I'm a specialist. I'm a culture curator." And if he hasn’t made it clear enough, which again, this comes BEFORE the Doechii podcast sample, he goes full tortoise TED talk with, "I'm 'bout to take it back when posters was on the wall. So I can make sure your kids got me on they wall."

There’s the real ambition. To be the poster on someone else's wall. Not just any kids either, but the kids in the know, from the parents who are hearing this EP. Gunn wants to be the rapper other artists name-drop in interviews. Gunn wants to be as famous for being "unknown" in the mainstream as he is revered by those who matter to him, who have taste.

I think Gunn’s sampling of Doechii is one of the most perfect encapsulations of what it means to consider different artists at different stages of their journeys I’ve seen in a minute. The idea that he sampled her and she shouted him out too - its an awareness of how creative influence flows in multiple directions. The underground can sample the mainstream as much as the mainstream can borrow from the underground and there’s still something new in each iteration.

I still feel like I’m right to worry about Doechii. The pressure, the sudden visibility, the - have you seen the “Anxiety” video (thanks to Ryan M. who said I had to watch it, btw)?! She’s living the transition and hare-on-fire moment in real time and we have to see how or if she’ll get through it. Her biggest Billboard hit is officially a song from five years ago that’s only big now and, extra Lizzo style, truth hurts.

But then I remember that the race doesn’t belong to the swift. The only finish line that actually matters belongs to the true artists. It belongs to the ones who figure out how to last, who figure out how to tortoise shell up and protect their own artistic momentum, who figure out how to win their way, one way or another.

Maybe Doechii will navigate it all beautifully. I hope she does. Either way, I’m taking notes from her and Westside Gunn. And Birbiglia and Questlove. And, my own anxieties, which are racing eternally.

Move at your own pace. Make art that matters to you. Cultivate the respect of those you respect. Let the external validation be a pleasant surprise rather than the destination.

The tortoise’s path is all about the pace and not burning out before the finish line.