When a bullied boy grows up

Comic Gary Gulman reflects + your overwhelm management strategies?

What happens when, as a kid, you are ridiculed, shamed, and taught that it’s not safe to be yourself?

You may become a shrewd observer of those in power and notice the clumsy ways they yield it. To help it go down easy, you may develop the skill of blocking jabs with humor. It may also become harder to let small slights go because they touch an old bruise.

And You may, of course, become a bully yourself.

I talk about all these possible paths with comedian Gary Gulman this week on Death, Sex & Money.

If you don’t know him, immediately put Gary’s two specials in your queue: The Great Depresh from 2019, and 2023’s Born on Third Base.

Gary was a smart, sensitive kid who was pushed around a lot growing up. He was much younger than his older brothers, who tried to toughen Gary up after their dad left when Gary was a toddler. “They were trying to be like deputy fathers in my family,” he says, “but they were unfit.”

Then Gary came up in the standup scenes in Boston and New York at a time when insult comedy was the reigning style. Gary did his best to work around them. “Those guys are surgeon-like in their ability to hurt your feelings.”

But Gary developed his own kind of forceful pushback. He’s aware he carries several chips on his shoulder — for rich kids who grow up to believe they earned their life of ease, or more generally, for powerful people who punch down — and that’s who gets skewered in Gary’s comedy.

GARY: I'm great to be friends with, but it's also difficult to be friends with me because I am very sensitive to disloyalty. Or criticism.

ANNA: you mean a feeling like they didn't have your back in a moment you thought they were going to?

GARY: Yeah, totally. And it's hard for me to forgive that because I'm so loyal…There are certain people I don't talk to because they were mean to a friend of mine and, and they'll be like, why do you not like that guy? And I'll say, I have never even met that person, but they were mean to a friend of mine….

ANNA: When you, like, observe what you see as, like, Social bullying among grownups. Like, what happens? Do you, do you intervene?

GARY: I mean, I don't yell, but I'm blunt. I'm very, very blunt. And certain infamous people will come into The Comedy Cellar, and I don't work there anymore for a number of reasons, but one of them was certain infamous people were accepted back there and would snub them or tell them, ‘No, we're not talking. I don't have any respect for you.’

So I say these things and I burn bridges.

Sometimes, this kind of moral clarity is warranted. Other times, though, it can get mixed up with stubborn righteousness.

Gary admits that this doesn’t always serve him:

GARY: My wife taught me this…she said it's important when you argue to argue a kind manner. But I was raised to try to win every argument, no matter what it took.

And frequently you could be very mean, and, but as long as you got your victory, which was always Pyrrhic, then, then you would feel, you would feel you won the argument because you made the other person feel bad or lose their cool.

And, and so, and it's not always easy to have rules of engagement, which means you don't say something mean or cruel or something that's going to linger….

So that's been really helpful. And then she's very forgiving. And so I'm very lucky and, and so I in turn try to be very forgiving with.

But outside of my, my marriage, I'm very sensitive to betrayal or criticism.

We timed the release of this episode to coincide with the run of Gary’s one-man show, Grandiloquent, in New York City.

You can listen here.

But I have to tell you, this week, I’m finding Gary’s self-aware reflections very useful. Four weeks into 2025, this has been a span of days when my cool New Year’s resolve to only focus on what matters cracked into a million little darts of overwhelm.

Too much is provoking me!

In the news and in everyday life. And you know what I do when I’m overwhelmed/scared/provoked? Lash out with defensiveness or righteous indignation. Usually, it’s in my head or under my breath. When it finally leaks out, it’s to my husband and kids, who get the less polite version of me, God love them.

So, instead of leaking, I’m trying to channel the overwhelm…as Gary does. And I get to lean on some very thoughtful and funny people to help. Tomorrow is my show at SF Sketchfest, and we’ll talk about losses, injustices, heartbreaks, chaotic uncertainty — AND how to move to softness and find some humor amidst all that. But we also might have a few moments when we just can’t help it and get bitchy!

There are **very few** tickets left if you can be in San Francisco on Friday evening and watch what happens in real-time. We’ll share the audio with all of you in a few weeks.

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So - what are YOU doing with your overwhelm?

Part of what’s thrown me off this week is the breakdown of some more healthful information consumption habits, such as concentrating on intentional phone use and taking in news at set times. But that gave way this week as I tried to track what was up and what was down and whether online Medicaid portals were functioning. 

How’s it going where you are? After the election, Americans —particularly Democrats — stepped away from political news. Did you? Have you stepped back? How are you spending your info-gathering time this month? Tell us! Let’s help each other!

If you have any other hot tips this poll doesn’t capture, please share in the comments.

Desspite my backsliding this week, I have two recommendations for things that have helped me mix up the stimuli I’m exposed to:

• Radio Paradise - I’ve been streaming this fun, electric, throwback-in-the-best-way radio station since I read this delightful profile in Alta Journal.

• Libby app - I’ve been digging in and putting some miles on my library card with ebook reading and audiobook listening via Libby. In the past several weeks, I listened to Gary Gulman read his book Misfit, along with Rachel Kushner’s The Mars Room and Thomas Frank’s Listen, Liberal. On the ebook side, now that I’ve finished Playground by Richard Powers, I’m moving on to Elizabeth Strout’s latest Tell Me Everything.

So far, none of these have been comfort reads, but I do appreciate the ways they’ve complicated and deepened my understanding of my existential unease.

Until next week,

Anna

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