#27. Ambitious Hat Acquirers and You

Are you pulling it off, or should you never have put it on?

Hi Everyone,

After a whirlwind few days of comedy travel, from New York to Spokane to Seattle to Boston, I’m back home in Brooklyn and out on the picket lines once again! I had a great time at Spokane Comedy club and the Upper Left Festival where I saw big-time favorite people and comedians Amy Miller and Kermet Apio. Then I had one of my customary 20-hour visits to Massachusetts to perform at a fundraiser for Roxbury Main Streets and have Mother’s Day brunch with my parents and sister. Plus the audiences raised a few hundred bucks for the Entertainment Community Fund with poster sales! Heck yeah!

My family and I are big time talkers, and so we do long catch-up hangouts whenever I visit, and I always end up learning that someone I met once thirty years ago has recently passed away, and also about my parents’ extremely specific media tastes. (I now know as much about the tv shows Manifest and La Brea as any person who has never seen a single episode of either.) This weekend, I learned that my mother can tolerate my dad’s recent deep dive into Phish’s satellite radio station, but she hates when Phish covers Beatles songs. (My dad agrees that these covers are not the band’s strongest work.) In my opinion, part of loving someone, whether it’s a friend, a family member, or a romantic partner, is remembering the little things they hate, even when they will never ever appear in your life unbidden.

THIS WEEK: Despite the 76ers defeat at the hands of the Boston Celtics in Game 7 yesterday, I am bravely returning to Philadelphia for three shows on Friday and Saturday at Helium Comedy Club!

PEP TALK FOR PEOPLE WORRIED THEY CAN’T PULL OFF THE AUDACIOUS NEW HAT THEY JUST BOUGHT

Okay maybe don’t buy this hat.

Maybe you bought a wide-brimmed sunhat on vacation. Or perhaps you picked up a swing revival-looking trilby while you were shopping for an outfit to wear to a friend’s wedding. Or, just as likely, it’s possible that you ordered some kind of cowboy hat online after watching an episode of Yellowstone. However you acquired this new headwear, it’s outside your comfort zone, and you’re feeling doubts. You’re worried that despite the charge you felt holding the hat, seeing the way it alters your silhouette in the mirror, or even just imagining the person you’d be with it atop your head, despite all that…you’re not pulling it off. You’re worried people will make fun of you.

Please let me reassure you: People are absolutely going to make fun of you. That’s fine! It’ll probably only be your friends and family (the people closest to you whose opinions you value and who know how to hurt you). But that doesn’t mean you shouldn’t wear the hat. The fashion version of “you miss 100% of the shots you don’t take” is “no one’s ever pulled off a hat they never put on.” The most important component of achieving a style is attempting it!

We like to imagine that mockery comes from small minded people with no vision or ambition. And that’s true. People make fun of things they’re too scared to try for themselves. Unfortunately, they also make fun of things that happen to look terrible in a funny way! But whatever the cause of other people’s laughter, you will have seized upon a fleeting moment of joy. A chance to shake up your daily routine, to expand your comfort zone. You can’t know how it’ll go until you try it. Isn’t that exciting? And so what if the guy who works at your coffee shop calls you Big Purple Hat for the next three years? It’s nice to be remembered for something.

PEP TALKS FOR READERS

A few of this week’s requests were a little lengthy, and despite their emotional generosity and high quality of their prose, I trimmed them down just a little for the sake of brevity.

I’m way in over my head with just relationship stuff. I really just want someone to say it’ll be okay. Right now it feels like it could help a ton.
- Between a Rock and a Heart Place

The short answer: It WILL be okay!

The long answer: Whether or not it will be okay depends a little bit on your definitions of “it,” “will,” and “okay.” (For the purposes of this discussion, I think we can agree on what “be” means.)

If by “it” you mean the specific relationship (or set of relationships) that is overwhelming to you now…maybe not! It could stabilize, sure. Or it could completely fall apart even if you don’t do anything wrong, like a soggy sandwich or an H&M hoodie. There’s at least one whole other person on other end of this situation, and it’s impossible to know that you’ll remain compatible or get more compatible than you currently are. So if that’s the “it” we’re talking about, the best I can tell you is it might be okay. I know that’s not especially promising. But sometimes the “okay” in “it will be okay” means that it will be over and that will be okay. So, you can see why I’m having a little trouble making a blanket statement here.

But, if by “it will be okay” you mean that you will continue to be a person with a rich interior life, numerous skills talents and interests, and many worthwhile relationships outside of the romantic situation that is stressing you out (while also preserving the possibility of future romantic excitement and fulfillment)…then hell yeah it’s going to be okay, no doubt about it. And also, of course, you can be okay even if it isn’t.

What’s good, Josh? I got laid off from my job going on 2 years ago, had to move back in with my folks, and I’m feeling lost. I could use a pep talk.
Signed,
A No Worker

One extremely stressful situation is when circumstances beyond our control put you in an undesirable position!!! Getting laid off doesn’t mean you’re bad or dumb or unskilled. It honestly means that your bosses are bad at the “having employees” part of being a company. Work and money really put our heads in a weird place though! Like, if an asteroid passed into Earth’s atmosphere, bounced on the ground, and knocked you into a swimming pool, you’d never think: Shoot. I must be terrible at avoiding asteroids. You’d think: Wow that was weird and not great, but I am sure I’ll recover from it in time after changing into fresh socks leaving my phone in rice for a while.

This is like that, but drier. You’ve been put into a tough situation because the economy is (in many ways) fake and (in many more ways) unfair. That doesn’t make the feeling of being lost any less acute, which is additionally upsetting. Still, this sensation is extraordinarily unlikely to last forever! It is extremely probable that you are lost like car keys and not like Amelia Earhart. You’ll find you soon!!!

Hey, Josh. The past few years have been weird/devastating/beautiful all at once (also I know this is a lot of context but it's important). 

In 2018 my wife Jenny and I had a baby boy who died when he was four months old because of an ultra-rare disease that we didn't even know we both carried. We spent the next year feeling like we'd been struck by lightning and eaten by sharks at the same time. We started working with an IVF clinic (only way we could safely have another baby). Jenny got a job at a university but had an exceedingly terrible supervisor. We transferred an embryo and it didn't work. Then the pandemic started. We transferred another embryo and she got pregnant, and in April 2021 we had a baby girl (she's now 2 and thriving - she says "hey"). We moved back to our hometown. We transferred two more embryos and she had two miscarriages. And next month she's starting a new job as an administrator at our local community college.

I dunno what format you normally opt for in your pep talks, but I thought it could be a fun going-back-to-work present if she got one from you. The past several years have been such an odd blend of this really great stuff happening, and really distinctly terrible things both large and small scale. We're hoping this summer is a bridge to something consistently better.

- A Very Sincere Writer [Josh’s description]

Hi, Jenny. First of all, I’m sorry to hear about all of the sadness you’ve experienced recently but so glad to hear about all your many good newses as well.

I get occasional requests for pep talks that are not very serious, and mostly ones that are medium serious. But this one strikes me as very serious. I don’t want to NOT take this on in part because I am a relentless people-please by nature, but in equally large part because I think it’s not that useful to write this newsletter if I’m only going to give pep talks about small to medium sized issues. Oh, you’re having trouble popping all the kernels of popcorn in your popcorn bag without burning any? I’m sure you can do better! But also…you will 100% be fine either way.

So, Jenny, here is my pep talk to you. You have dealt with so many intense life events lately that I have to imagine you have an intensely honed perspective on what matters to you and what doesn’t. You have a loving family and community. You’re starting a new job with the knowledge that if it doesn’t suit your needs, you can leave. You know what matters to you and what doesn’t, what’s worth the effort and what isn’t.

You have put yourself in a position to have a happy, healthy life full of care and closeness and fulfillment. That’s such a beautiful way to live. I know your last few years have been full of ups and downs, but you also already have consistent goodness in your life. You generate it yourself, and you spend time around people who generate it for you too. You know what you’re doing, and that knowledge will help you weather the bad parts, enjoy the good parts, and not give a shit when the popcorn doesn’t pop all the way.

PICK-ME-UP SONG OF THE WEEK: Gladie - “Nothing“

I have been listening to Gladie’s 2022 album Don’t Know What You’re In Until You’re Out a lot lately! DKWYIUYO is one of my favorite records from last year. It’s a perfect driving around with the windows down album, during this, the perfect driving around with the windows down time of year. “Nothing” is another song where the lyrics are more probing than perky (in a great way), but when you listen to it, you kind of want to chase someone up and down a bunch of alleys and fire escapes. Or maybe that’s just me.

UPCOMING TOUR DATES

I’m getting started on the second leg of my 1900s Kid Tour, and the first few dates are listed here! The rest of them so far are of course on my website!

5/19-5/20 - Helium Comedy Club in Philadelphia (Three Shows)

5/31 - The Comet in Cincinnati

6/1 - Helium Comedy Club in Indianapolis

6/2-6/3 - Helium Comedy Club in St. Louis

6/4 - The Comedy Club in Kansas City