By the time you get this newsletter, I’ll be mid-flight to the island of St. Croix. 🤿 🌊 

As I write this at my desk at 9pm on a Monday evening, I’m putting off packing til the last minute, like I tend to do. I pack well under pressure. I also might be lying to myself about that. 🙈

I wrote about my first trip to the Virgin Islands in my third newsletter drop, but I left out one of my favorite stories.

In 2008, my friends and I took a random trip to St. Thomas… we got the wellness check, I had an EPIC ass bruise… you got all this in the newsletter drop linked above. What I didn’t tell you is that I went back to St. Thomas a second time months later (referring back to afore mentioned shitty relationship), and I only had $300 to my name during that trip. I was almost out of money with two days left on the island, when I walked into a bar called Molly Malone’s in Red Hook and saw a chalk-written sign:

“Oil wrestling tonight! Cash prize!”

Oh, hell yea, I went back to Molly Malones that night. Not only did I win my oil wrestling match against a woman twice my age in a kiddie pool full of olive oil in a bikini I borrowed and win a cash prize of $160, but Kenny fucking Rogers was in the audience laughing so hard at my overzealous wrestling performance, he left another $160 at the bar to match my winnings.

I walked out of that bar with a top tier spa treatment (olive oil is fantastic on the skin, I must say), the confidence of a roller derby chick, and $320 CASH which was just enough to get me through two more days of partying before I’d be on my way.

Kenny has no idea how much he saved me that day. I had plenty of rum and even went home with a little cash. Ahh the priorities of 22.

I have a lot of stories like these, accidental winnings in a time where I had nothing to lose. Remind me to tell you all someday about winning a hand-jive competition (I have to be careful how quickly and articulately I say that in a public setting) judged by Olivia Newton John in Las Vegas, the Tom Cruise Risky Business costume win for my rent money during Halloween of 2008, or the towel, chicken wings and free beer story. Tales for another time… I was broke and thriving. What a time to be alive.

By the time I was 23, I already felt like I’d lived a thousands lives. Not because I’d experienced anything specifically or unusually traumatic, but because I was constantly putting myself in horrendous scenarios and “lucking” my way out of them.

And that, my friends, is what we call oblivious charisma.

Each time I return to the islands, it’s a reminder of a young, carelessly carefree me who’s overcome my bullshit time and again, and always always always found a way to make it a damn good story. Hey, at least I had pretty radical tales to talk about on stage before I knew how to actually write a joke.

I look forward to writing next week’s newsletter from my last day on St. Croix. 🍹 Perhaps we’ll have a new grand tale on our hands…

The Hustle

Last week’s hustle was pretty chill, and that’s the kind of week I needed preparing for St. Croix; a totally different blend of hustle-y chillness.

I was in San Fransisco having a jam sesh with my co-founder (more on this in last week’s newsletter), and guest speaking at her class at California College of the Arts.

Her students are coming up on junior reviews, and they always need a bit of tender lurv to prepare them to speak and pitch in a public forum in a way that doesn’t put people to sleep.

Queue the comedian and founder who clearly enjoys the shit out of public speaking.

It was actually pretty eye-opening for me to talk through my career; the ups and downs, and the hundreds of other jobs and crafty things I had to do to get to where I am now.

How often do we forget to reflect on all we’ve truly accomplished?

The workshop was segmented into Charisma, Confidence, Crowdwork and Storytelling.

I was a bit distracted in front of the students, referencing back to 2003 and my time at Second City Chicago, and coming to the realization that zero of the kids in the room had been born yet by then.

Despite the irony of every analog billboard being an AI ad likely written by AI, there was definitely a better quality and a less toxic “hustle culture” tech stench to SF this trip - cafes without wifi, fewer people toting their laptops everywhere or working in co-working spaces until 11pm. Way to go, San Fransisco?

But here’s the thing—I wasn’t just there to teach. I was also there to witness something. And what I saw? A generation that has everything at their fingertips, yet somehow, they’ve got less to say.

I don’t mean that in a back in my day way (okay, maybe just a little). But when I was their age, we had to actually live through some shit to have stories to tell. We made irrational, wild, sometimes downright insane decisions, and those became the stories. We got lost in cities we didn’t belong in, took gigs we had no business taking, fell for people we had no business falling for. We ate food off the ground. We played outside without cellphones. We collected experiences the hard/good way.

Meanwhile, these kids have Google Maps, digital receipts of every convo, GrubHub in 6.5 minutes, and a backlog of their entire lives stored in the cloud. The stakes are lower. The mystery is gone. And yet, they’re the ones needing guidance from me about how to be interesting and command a room.

So yeah, I was there to workshop storytelling and charisma, but part of me just wanted to tell them to go outside, make a few bad decisions, and come back when they’ve got something real to say. A little experience with a dusting of “uh-oh, that was close.”

And maybe—just maybe—do it without recording it for TikTok first.

In a world where so many are letting ChatGPT write their story, I’m glad I could use humor and a little foreign nostalgia to teach even a kid or two how to write their own.

The Chill

Some of my happiest moments in life were when I had nothing to lose.

Truth is, there’s always something to lose. Young “you” was just too naive or too in the moment to realize the possibility. What sheer freedom. 💃🏽

As I get older, it feels like I’m having to constantly put in thoughtful work to retrain myself to believe that everything is going to work out, even though young me held that belief instinctually. Funny how that works…

When I approach situations openly, being present, without panic, I’m always surprised and delighted by the outcome. But our big grown up brains often get in the way of simply enjoying life’s ride like we once did, and letting a real story unfold.

I wouldn’t want to be young me again, but I’m thankful as a comedian, adventurer and creator, I get to bring that girl back into the fold consistently because I’ve built a life of child-like playtime (comedy) blended with adult hustles (business) and adventures (islands, obv).

If you find yourself idle this week, do yourself a favor and go down a Myron Golden rabbit hole. Often times as adults, we get in our own way, and we just need to be reminded of a time where things were a little less thought through.

What I’m trying to say here is that young me was so life-trusting and in the moment, that I now have a life I never imagined (but also, did imagine in my wildest dreams) just because she decided to take all the risk. She didn’t know better, so here I am.

Her young naivety, and willingness to live and learn later, made me bold and daring in fantastical way.

I thank her, that idiot.

It’s now 10:24pm and I really should pack for this flight I’m on at 5am. 🧳 

I’M SO EXCITED TO BE BACK ON THE ISLAND—me now realizing this all caps statement feels like a facebook status from when our grandparents first hijacked the platform.

I’m a big fan of having pockets of communities in places I’m obsessed with going, and it’s fun to return to a band of friends and comedy lovers out there. As much as I love city life, I’m an island beach girl at heart. Maybe I just like the balance…

Upcoming Shows

For the sake of getting my island chill on, I’m only promoting the St. Croix shows this week.

Wednesday April 9th @ Common Cents is SOLD OUT.

Thursday April 10th @ Leatherback still has some tickets, as does

Friday April 11th @ Nauti Parrot

Saturday April 12th @ Leatherback is just about sold out.

If you’re in St. Croix, don’t wait to get tickets! Last year we had to oversell and open up standing room only/bring-your-own-chair tickets… I want to make sure you get a good view of us.

Love you all and cheers to the hustle + chill… and a little unintentional winnings from music legends.

xx NPH