We're previewing the Rochester Fringe Festival 2026 — and the main thing you need to know right now is that Penny Sterling is bringing her show HAVE I EVER TOLD YOU ABOUT to the Focus Theater (Sibley Building) on September 20 at 5pm and September 23 at 7pm — grab $20 tickets at rochesterfringe.com, and yes, go to as many shows as you can because we mean it.

Check out the episode on Just Can't Not wherever you get your podcasts or on Lunchador.org!

https://player.captivate.fm/episode/84d6e819-479d-4ec3-803d-fbfe80ec103d/

I promise it's not just another one-person show: Penny's built this as a choose-your-own-adventure of stories — an odds-and-ends set of hilarious, weird, and tender tales that ranges from small-town pies to a legendary KGB-bribing rum‑raisin ice cream caper. We talk about how her storytelling balances entertainment, education, and inspiration — the classic Fringe turn of taking you low and then slinging you high so the laughs and the lessons land harder. I loved hearing about her craft (she trains as an actor, rides to write, and insists on genuine truth rather than easy jokes), and she also plugs other Fringe bits like Catharsis Time and a walking story plus some photography on the side. Come for the grin satisfaction, stay for the human stuff — this is storytelling that makes you laugh, think, and maybe buy a slice of fruit pie after the show. Get your tickets, bring friends, and meet us downtown Rochester for Fringe — we’ll see you at the Focus.

Mentioned in this episode:

Joe Bean Roasters

Visit joebeanroasters.com to get fresh roasted specialty coffee either by the bag or with a Perpetual Joy subscription!

Well, that music means it's time for another episode of Just Can't Not.

Go to rochesterfriends.com to get your tickets for as many shows as you can go to, because you should go to as many shows as you can go to.

And I'm here with a guest.

Guest, why don't you introduce yourself?

Hi, my name is Penny Sterling and I am a storyteller from Rochester, New York.

Yes, you are.

And you have two shows on September 20th and September 23rd.

That Sunday and Wednesday at the Focus Theater, which is in the.

In the Sibley building downtown.

Third floor, beautiful venue.

5 O' clock on Sunday, 7 o' clock on Wednesday.

Tickets are $20 at rochesterfringe.com and the show is called have I ever told you about.

Why don't you tell me a little bit about this show and then we'll dive into other stuff.

Well, this show is basically an odds and ends.

So it's like the Contractual Obligation album.

Okay.

I've got all these extra songs.

I'm just gonna put them all together on the.

On the oblig on the album.

That's almost what this is.

I have a whole bunch of stories that I have told in different places over the years.

And everybody who has heard them goes, when are you gonna put that in a show?

And, like, they don't really fit very much into, like, most of my shows are about me and being transgender and what it's like to be a lilt, which is my term for later in life.

Transitioner.

I like that better than a lot of people say trans elder.

Yeah.

It's also like, you know, I hear just myself, like, they're called me a geriatric millennial.

Oh, my goodness gracious.

Elderly millennial.

And it's like, how about we just.

We're just.

Okay.

Yeah.

Okay with things.

Yeah.

Let's not label everything, you know, like, you know, on, off, you know, Danger.

That's a good label.

You know, Poison.

Good label.

You know, it's like, human beings don't need labels.

Yeah.

And I love that this is your Dave Barry column moment.

Like, this is like, oh, well, I got a whole bunch of columns.

I guess I'll just throw it into a book.

Yeah.

Kind of.

Sorta.

Yeah, There's a whole bunch.

And I have more stories to tell than I have time to tell them.

So what I'm doing with this is kind of a.

Remember the old choose your own adventure books?

Absolutely.

Well, I am doing a choose your own fringe show with this and it's not on the website because I was like, how am I going to present?

And it finally hit just the other day.

So my posters and my advertising, I. I've mocked a. I mocked up a cover of a choose your own friend, choose your own adventure book that has.

It's about me and it's like all these different imperences of me throughout the years and just like all these stories are different things that happened to me throughout the years.

And I have a. I'm going to have a sheet up with a whole bunch of very interesting titles like the 3 Day Snowball Fight, Aleister Crowley, the bugs and my friend Phil.

You know what's another one I have, it's in German so I have to actually look at it.

But it's a.

It's, you know, but I.

But it's about the, the German ghosts of Swilberg.

Oh sure, of course.

Yeah, of course it is.

And just different things like that.

And.

And of course the one that everybody loves, which is.

Have I ever told you about the time I got out of trouble with a KGB agent in the Soviet era Kiev by bribing him with a five gallon drum of black market bootleg rum race East German rum raisin ice cream?

I mean that's, it's almost.

I mean so many people have that story.

I know, but.

So it's like your version has to be good version for it to be in the show.

Yeah, because.

Because my KGB agent's name was Boris or actually Boris as he would say his name was Boris.

I will say as I have, I have a collection of friends who are the most them they can possibly be.

And they have no ability to be anything but the version of them that they are.

I like that one of them is gentleman goes by the name of Chris Carlson.

I don't know if you've ever had the pleasure of meeting him.

I met him, but I don't think it was a pleasure.

He's a whole bunch of a lot.

But the stories I've heard from, you know, from Eastern Europe and going there during the early 90s and stuff like that.

I mean so many fascinating stories and like bringing stuff over borders.

I'm like, Chris, I don't need to know all this stuff.

Yeah, well, it is fascinating and it really.

I.

One of the reasons I like telling it is because I kind of subtly like remind people this is what it's like to live Under a totalitarian state.

Yeah.

This is what it's like when the truth is secondary to the party, what it's like to not be able to speak truth to power, and the sort of things that happen in countries where this is the norm.

Yeah.

And it's one of those things that's very.

It's disconcerting.

As somebody who has dedicated.

I've dedicated my, like, my whole life to learning as much as I can learn about things.

And the.

The separation from fact, where opinion has become more.

More worthwhile than fact, than experts, is, I'd say the thing that bothers me most, obviously, you know, people being, you know, shitty people to other people.

That bothers me a lot.

But in the end, it's respect and I, you know, the experts in the world are worth our time.

Yeah.

And, you know, understanding, respecting people's journeys and opinions.

I mean, because they've gone through something.

Exactly.

And just about every story that I have heard back from cisgender heterosexual people about trans people has absolutely nothing to do with.

With trans people and absolutely everything to do with their own internalized fears, fetishes and desires.

Yeah.

And so it's like.

It's like, you know, the ones where they say, you know, stay away from my kids.

Well, first off, I.

You're.

You're like.

Usually you're just a blank ghost of a person on social media, so I wouldn't know your kids from a hole in the ground.

Right.

And secondly, you know, it's like, that's.

No, I'm.

I'm.

I have.

I've raised four children of my own, and I've always made sure that my place was a place that was safe for people to be whoever they were.

This is even before I transitioned.

Yeah.

But I think that's.

I think fundamentally that is.

It's one of those things that is such.

It's such a net good because it makes you feel better because you're helping others, that you're present for them in the moment.

Right, right.

It's.

It's not that you're being generous to somebody that needs.

That needs you to feel that way.

It's doing good for others makes you feel good about, hey, I can do something.

I can do something.

That's good.

Yeah.

It's so hard because, you know, the world has so many systemic problems and that, you know, you can get so disillusioned, especially the younger generation.

Yeah.

There's so much disillusionment and, you know, cynicism, and rightfully so in many ways, but those little Things where you're able to help somebody in your circle.

Yeah.

Even if it's a little thing, just being there and being in a welcoming place.

How valuable is that?

It's very valuable.

And it's also very valuable to show vulnerability and to show uncomfortableness.

All these times where people are like, oh, what am I going to tell my kids about you?

That I'm a nice lady, I dress pretty well, I'm kind of funny, and, you know, I cook really well.

I mean, there's.

What do you want me to tell you?

It's like we're not.

And also just the fact that so many people are afraid to talk about uncomfortable things.

Yeah.

And to accept uncomfortable.

Accept uncomfortable truths about themselves.

There was a second grade teacher who's like, I'm supposed to talk about slavery to my kids this year.

How am I gonna do that?

And I was like, I'm gonna do it by telling them.

And tell them how uncomfortable you are about this.

Tell them how it really sucks that we have a history, a tribe that we are all of.

If we are white and American, we are complicit in the subjugation of a marginalized group of people.

And how does that make you feel?

We are also.

We've fought for freedom, we've fought for civil rights, we've done other things, but.

But also we are in other people's eyes, often the bad guys because we've done bad things to them.

Well, and I think that's part of that whole journey.

Right.

Is.

I think part of being a real ass adult is knowing yourself.

Right.

And I don't think you are a real adult unless you know yourself, at least to a point.

Is living with uncomfortability and learning how to listen to somebody else.

Learning how to just be there and be present in the moment.

And that whole thing is.

Yeah, that sucks.

It doesn't mean you have to feel bad about it all the time.

You make a mistake, hey, you know, we've all.

We've all done it accidentally.

We've all done the accidental, you know, accidental misgendering of somebody.

If somebody knows you and you're present and you're a decent person, everybody feels that in the moment.

Say, okay, well, got that wrong.

Oh, great, I feel bad right now.

Fix it.

Everything's fine.

The history is important to know.

It's important to do your best.

And nobody's perfect with anything except Donald Trump.

Well, I mean, think of all the golf tournaments he's won.

He's such an accomplished athlete.

I mean, what an orator Absolutely.

I mean, think of the captivation.

It bothers me so much.

Everybody says, oh, what a great.

What a great talker.

A terrible.

Yeah, he's a terrible talker.

Yeah, he's a rambler.

He was a rambler in the first presidency, and he's even worse now.

Well, and then as somebody who has dedicated so much time to being somebody who knows how to work with an audience and using skills you've built over the years to communicate feelings and the ups and downs and the roller coaster of life, I kind of want to step back to that.

So, you know, you were in production for a long time.

You mentioned you've done radio.

You've done so many things.

You've spoken in public and been a public person in multiple different versions of your life.

When you started to.

When you start to think about, here's how I want to be a creative person in the version of you, the real version of you.

When you're thinking about, how do I want to do this, what about the one person show was appealing to you?

Well, the thing that was most appealing about it is that I knew the casting director, so I knew I'd get the gig.

Yeah, it's a great starting point.

Well, it.

Well, especially for me.

I trained as an actor.

I am a very good performer.

When you see me on stage, even by myself, you see me performing, doing things, emoting all these different physical things and things that I do with my words, the pacing, the pausing, all these things.

I'm very good at that.

And since I transitioned, I have auditioned for 19 different shows.

I've gotten two callbacks.

Wow.

And I have not been cast in any of them.

The only show that I have done that I didn't have to write for myself was, and this is really ironic, the Vagina Monologues, because the producer asked me if I wanted to do that, and I.

The two things I never refuse are stage time and fruit pie.

And so this was the stage time, and I said yes, and it was an amazing show.

I don't know if you're familiar with the Tanis Theater association of New York State.

This production swept the Tanis Awards for our category.

Got two best actor awards.

Myself and Kesha Shari both got.

I was the audience favorite.

I did a. I wrote a piece for the Vagina Monologue about how it feels to be a transgender person doing a show about vaginas and how the vagina was a metaphor for a lot of different things about how people perceive you and how they control you and how they want to control you.

And it was amazing.

It was absolutely amazing experience, and I loved it.

So before.

I mean, we're diving into so many important things.

I need to stop and talk about fruit pies for a second because you brought it up.

Oh, yeah.

I love fruit pie.

So what is your.

A number one fruit piece as a food nerd like this?

My other show is Food About Town.

I've done forever.

I love food and drink.

So, like, what's the fruit pie?

I find favorites to be extraordinarily limiting.

Yes, my favorites.

My favorite.

You can never go wrong.

I can never go wrong with an apple, a blueberry, or a cherry pie.

I love.

I adore all of those things.

And I also love mixed berry pies.

I love lemon meringue pies.

I like key lime pies.

Not a big fan of strawberry.

Not asparagus.

What's the word?

Rhubarb.

Rhubarb.

Strawberry rhubarb pie.

Not a fan of that.

Yeah, but they're just basically, if it's a.

If it's a fruit and it's done well, I love it.

I make a lot of them myself.

Well, and I think it's also what an opportunity to celebrate the seasonal bounty of our area as well.

I think it's embracing that time.

It's embracing time both there and then.

See, look at this.

This is my radio pivot right here.

Embracing the version of version that things are right now.

Is that something you found is important in creating your shows?

I remember I went to go see the one where you're doing the bicycling.

Oh, yeah.

Mounting Washington.

And that was a tremendous show.

But when you're thinking about creating one of the shows, how much of it is it just reflecting on the past?

And how much is it reflecting on the version you are in the moment right now?

A lot of it is reflecting on where I am right now and what the story of my past can bring of value to people who want to watch it.

Both Entertainment, payment and education and everything.

I used to teach public speaking, and I said that I broke down my.

The way I did.

I broke down public speaking into four categories.

Informational, inspirational, educational, and entertained.

Null and.

Yeah.

And that's the sort of thing that you would do when you say stuff like that.

And you put things like entertain and all in it.

It makes people laugh.

It also makes them remember, and it also shows how you can do it.

And so I try to put all of those things into all of my shows.

Education, inspiration, entertainment, education, inspiration.

And what are the.

Whatever the, the other one.

The other one?

Yeah, the fourth one.

Whatever it was.

The other one.

It's.

Yeah, it's just me talking.

Who's, who's listening?

So I've been thinking a lot about the one person show locks.

I've.

I've been to a lot of them and at Fringe, both here in Rochester last year and in Pittsburgh in April.

Inspirational.

That's the one.

Pittsburgh.

I love Pittsburgh.

And it was so much fun going down there and seeing some, you know, different versions of one person shows and, you know, different.

The ways to do it in many different ways.

Some are in, you're using clowning, some are doing, you know, very, you're very serious.

And I've seen so many different versions.

When you're writing, when you're writing out your show, how, you know, do you do tests?

Do you, do you do it first and then record and then write what you've done, or are you more of a writer first?

I am a rider.

R I D E R I don't listen to music when I'm riding my bike.

I don't listen to movies when I'm driving my car either.

I'm usually just going over stuff in my head and how do I want to put it and how do I want to have that?

I know the story because I was there.

I know how it made me feel.

I know how to like put the pieces together most of the time.

But there's always sticking points.

You know, I want this to be something that is not so heavy that, you know, I, you know that people are like weeping and crying and like, you know, gnashing their teeth.

But I also don't want to substitute comedy for truth.

Yeah, genuineness, right?

Absolutely.

I think that's the core to me of the one person show is there's a genuineness to it.

And I love that you brought up that conscientious thought about the dynamism of the show.

I think the most successful ones I've been to have that there's that up and down.

Right.

And you're purposefully, you know, you're not tamping the audience down, but you are, you're preparing them.

And then when the up happens, the laugh happens, it's a bigger laugh.

Yeah.

Because you've brought them down a little bit into that, you know, into some of the harsher realities of things.

And then you, when you bring that light, it's so much brighter.

And then when you bring down, it can be so much more impactful too.

I just love that the finesse I Think finesse is the thing I think about the most with a successful one person show.

Yeah.

Yeah.

It is actually very, very, very important to have what I call the turn.

Several turns and stories.

The one mounting Wall street.

And the turn was how this thing happened to me.

And then the misery that it brought up and then the resolution that.

That up and down came.

And where I say, huh, it turns out this is a show about being transgender.

After all that right there is the money shot.

Because then people realize, oh, my God, everything about being transgender, you have.

If you are transgender, you have to speak about being transgender.

Yeah.

It's horrible.

It's horrible in.

In some ways, but it's necessary in others to get.

Because there's so few of us that are out.

There are a lot more that are not, a lot more that are not.

Yeah.

And so it's kind of incumbent upon us.

We've gotten to almost a tipping point, and that's why there's such a huge fucking backlash.

Can I say the answer?

Oh, yeah, go for it.

Okay.

There's such a huge fucking backlash to that because we are expressing joy and freedom and we are very much outside of the patriarchy, even though.

And that's why we have so many, like, terfs, Transgender, exclusive radical feminists.

Although they're.

I don't consider them feminists because 100.

No.

So I call them.

I don't call them that.

I call them feminism, appropriating radical transphobes.

But no one seems like that.

But anyhow, I can't imagine why.

I don't know.

That's what I say to that.

Yeah.

So.

And a lot of times I'm like, you know, you are serving the patriarchy by doing this.

He goes, no, you're the man.

You're the patriarchy first.

I'm not the man.

And just because somebody is a man does not mean they're serving them.

Like, I'm actively working against.

Just by my existence.

I am disproving the patriarchy.

The fact that men should be, by Right.

Running everything.

And it makes people nervous when somebody becomes.

Someone transitions and becomes successful.

One becomes confident, becomes happy.

Yeah.

God forbid somebody is happy being the version of themselves that they've always been.

Yeah.

And it's like happiness is such a radical thing when you're talking about, you know, people who have been just denigrated over so many years.

I kind of want to go back to something you briefly mentioned during.

During that last section, was that there's an obligation.

It's.

I don't know, it Seems like it's many things at the same time.

It's a responsibility.

It's a.

You know, in many ways, it's a great thing to be able to do, to be somebody who has the skills to be a.

To be a great order and a great storyteller.

So it is a responsibility to talk about, you know, the trans existence and your experience doing it.

So my unfair question is, do you.

Do you feel that there's a show coming up in you that won't be touching on trans identity at all?

Do you think that's something you want to do?

That is you're writing it?

I don't think it's something that is possible for me to do.

I am friends.

That's all we had.

I mean, shout out to Bill Hicks.

I mean, the angry white guy is a very successful model.

Yeah, absolutely.

And then I transitioned and I tried to get back into standup comedy, and again, I found I was substituting truth for laughs.

I didn't want to do that, but I had to do.

Whenever I do stand up comedy, I have to address the fact that I am transgender.

I did a show called Parents and Children, Husbands and Wives that was about being all of those things, and there was very little transgender content in it.

And there are people who were a little bit miffed by that.

And so one of my favorite comedians that I worked with and as a human being and everything else, his name is Malcolm Whitfield.

He's now in la.

Hey, Malcolm, I know you're watching because you follow me everywhere.

Yeah, no, he does, but we talked about that one time.

We talked about that a lot because he was a black stand up comedian, and I was a transgender standup comedian.

And how you had to bring.

You had to.

He had to bring up his blackness in every standup show that he did, and I had to bring up my transness in every standup show that I did or every show that I.

Because that's what people expect.

And it's.

I don't know if that's.

I would love to have this get to a point where that doesn't matter.

Yeah.

And I also am trying to, in some ways, plow the road so that the next generation of trans person doesn't have to be trans and make that the most important thing about who they are and what they're doing.

There are shows, like, I see shows that I don't know if you remember.

Good Omens.

Yeah.

Did you watch the series?

I didn't watch it, but I'm familiar with it.

Okay, well, there's stuff in the second part of it.

For example, there is a husband and wife where the wife is pretty obviously transgender, and she's also a poet, and she runs a bookstore, and she's, like, an influential person in the circles that they're in.

And those are the things that they focus on with this character.

It's not a major character, but those are the things that they talk about.

They never talk about the fact that, oh, she's transgender.

Your husband married a transgender woman.

That's never a discussion.

But she is, you know, she's clockable, and so am I, and I will ever be so.

And so one of the things that I do is, like, you know, I'm here.

I'm trans, and I am going to be charmingly transgender and try to make you as uncomfortable as I can and then make you as comfortable as I can through humor, mostly.

Yeah.

But that's.

That's what I see is important about that.

Like, okay, trans people are just people, and they are happy, which pisses off a lot of successful white men who.

Have you ever noticed that?

They're never happy.

It's the thing that drives me the most crazy is there's so many people that are living on.

You know, they're not in the.

They're not part of the mainstream.

Right.

They're not part of that one path.

Right now.

I'll reference, like, you know, my wife Carrie is, like, a wildly talented designer, and she's found her place to sell at furry conventions all over the country.

And I've had the distinct pleasure.

And it's not my space, but I've had so much pleasure going and communing with the furries and being present there.

And, yeah, it's not my space, but she made me a character.

I wear the thing.

I tell them, like, hey, she made it against my will.

Yeah, it's a funny line.

But in the end, I'm there.

I want to be respectful of the people who are trying to be.

Okay.

Yeah.

That are trying to be happy.

They're trying to express themselves, and it's not my thing, but who the fuck cares if it's my thing?

It's making their lives better, and it's.

Not hurting anybody else's life.

No.

And I think that's the thing is, like, why do you.

Why do you worry so much about other people being happy?

It's your responsibility to make yourself okay.

See, that's not the that's not the message that is ever brought out in cisgender, patriarchal culture.

It's the closest you get to happy, the closest anybody gets.

And I know this because I was.

I pretended to be a man for more than 40 years.

Grim satisfaction.

That is the closest that anybody gets to happiness.

And the grim satisfaction isn't for the thing that you attain.

It is for the thing that you.

Well, the thing that you attain is making somebody else lose.

That is usually where the grim satisfaction comes from.

Domination.

Domination, absolutely.

And that is a horrible thing to try and maintain because if you are dominant means that people are going to always try and knock you down.

Yeah.

And so that's what we have as a society.

And I think it's.

To me, it's one of the great joys in life is to help bring people up.

Right.

It's the thing that makes you feel the best about yourself.

It's the thing that makes an impact on others.

And.

And wait for it.

This is my pivot at the half hour mark of our show.

You know what?

Instead of Grim Satisfaction, you know what's even better?

Grin satisfaction.

And if you want a grin, you should go to.

Have I ever told you'd about the shows on September 20 and September 23 at the Focus Theater that, you know, Penny's running?

I gotta say, as somebody who's been to one of her shows, a couple of the shows before, they are a delight.

They are so talented and the, you know, the expression of the entire journey, but of so much of yourself.

This is a show you definitely want to go see.

Get your [email protected] and, Penny, where else can people find you if they want to check out the rest of your work?

Well, I'm also going to be doing a story and a show called Catharsis Time.

Oh, that's a great one.

I haven't talked about it yet this year, but it's a fantastic show that held every year.

Yeah.

At Fringe.

Yeah.

And so I've got.

I've got one for that.

I'm.

I'm doing a story for that.

And there's two of those are on the first and second Saturday of the festival.

Awesome.

Yeah.

And I think the pro.

The, The.

The.

The store.

The, the topic is resilience, I believe.

I can't imagine you have anything to talk about that on.

I'm gonna talk about.

I'm gonna talk about walking.

Oh, I love that.

Yeah, it's.

It's my.

It's gonna be all about walking.

Yeah.

So, yeah, so that's one of the things that I'm doing.

I'm also doing a lot of photography and I've been doing some having some stuff displayed in different galleries.

So maybe something happens.

I'll let you know and we could talk about photography for a while.

That would be awesome.

Anytime.

It's somebody I've always wanted to have over in the studio.

So I'm really glad we got a chance to do this today.

You can also follow Penny over at at Penny Sterling on Instagram.

Other shows and if you want to learn about other shows, check out other shows on the Lunch at our Podcast network.

Go to lunchadore.org to look at all the shows right after this.

We're recording an episode of Reader's Advisory with one of their Rochester Book Club episodes.

Really excited about that and make sure you go to rochesterfringe.com and we'll see you out on the fringe.

This has been a presentation of the Lunch Podcast Network.

La.