Following Your Passions on the Road to Success

If you’re a reader of my blog, you know that I often recommend that you stop looking to the gatekeepers to give them validation, but instead work on developing your own shows and your own work so you do the work that inspires you.

So I was incredibly proud and impressed when I found out that one of my former students, Gabe Caruso, had done just that.

Gabe had studied improv with me in Chicago before moving to New York two years ago to get his M.F.A. in musical theatre writing at New York University. And recently, Gabe and his thesis partner, Sangwoo Simon Lee, found out that they had received the Amas Musical Theatre’s Eric H. Weinberger Award for Emerging Librettists for their new show, “Settle Down: A New Hip Hop Musical.”

This week, I asked Gabe to share with you some of his thoughts on winning the award and also give his advice on following you passions. Enjoy!


Even though I spent a few hours preparing the application for the Eric H. Weinberger Award, when we received an email saying our show had been selected out of all of the applicants, part of me believed it was a scam. We were asked to stay quiet until the press release went out, so when we had the W-9 forms sent to us to receive our award, I kindly informed our contact that we would be waiting until the press releases before sending in our social security numbers. I was THAT skeptical.

As a writer, I have a hard time believing that people value my work. In my brain, I have always been able to justify awards I have received as people being nice, and not much else. For example, when my play, “Dundee,” won Best New Play, and I was awarded Best Playwright by The Chicago Reader, my brain reminded me that the award was not voted on by a jury of theater professionals, but instead anybody who clicked on a link. I was able to justify this award as me having an engaged Facebook following. When it comes to my writing, if there is a way that I can knock myself down a peg, I will find it.

I also carry a lot of doubt with me as an artist because I am horrible at auditioning. I hate it. In Chicago, I auditioned for everything I could, and failed over and over again. It seemed like the only auditions I “passed” were to get into classes where I could fork over hundreds, if not thousands, of dollars. I am grateful for these failures because they pushed me to create my own work. It’s much harder to not get the part you are going for when you’re writing the script, and producing the show yourself, so that’s the route I went. It felt much better than my Second City teachers yelling “Gabe! Care about anything!” during my auditions. (And yes, that really did happen.)

At NYU, I learned that this self-doubt is just part of being a writer. When I first showed up to the M.F.A. program, I had the biggest case of impostor syndrome. I was earning my master’s in musical theatre writing, despite having seen probably less than 10 professionally staged musicals in my lifetime. I grew up on Disney movies, sure, but I would never have considered myself a “musicals” kinda guy. I applied because I felt that I had a unique skill set in both rapping and long-form storytelling, and this was pretty much the best way I knew how to combine my two passions. Even my generous scholarship was no match for my brain and its ability to find excuses for my success. And sometime around the second semester, I realized that almost everybody in my class felt the exact same way that I did.

So maybe that’s why this award means so much to me. Sangwoo and I poured our hearts into this story, and it wasn’t all rainbows and sunshine. We had a steep learning curve, as most collaborators do, and it took us quite a few months to be able to understand each other’s artistic strengths and languages. It didn’t really help that not too many hip-hop musicals exist out there, so for a lot of our process, we were making up our shorthand/process as we went along. We wrote some great songs, and some flat-out awful ones. We made our faculty advisors cry, and laugh, and on at least one occasion, we made them laugh when we were trying to be serious. Not the best feeling in the world, but thank God for the honest feedback. (That song was BAD.)

While my work has been performed by talented actors, many of whom I consider close friends, everyone has always had day jobs. In March of 2020 I was so excited for our thesis to be presented, as that would be the first time that my work would be presented by professional actors. I was beside myself. The previous year, as first years, my classmates and I had stage managed the second years’ thesis projects, and we knew what to expect in these readings. Then on a sad day in March, our department chair came in to tell us that the theses would all likely be canceled due to Covid. It was heart wrenching.

We finished writing our show, but Sangwoo and I recorded all five parts ourselves. It was a far cry from what we were expecting, and to be honest, it was very difficult to find the motivation to finish our show.

We experienced another blow when we pitched our show to a very well-respected musical theater university. When we said that three of our five characters should be played by non-white performers, we were told this could not be accommodated, and so they were going in another direction. That was another kick in the teeth because it felt like I had self-sabotaged in an unexpected way. I would be lying if I didn’t say I spent the first several months after graduation being a depressed and mopey mess. But life has picked up, and very recently, thanks to this award, I have been re-energized.

With this award from Amas, my skeptical brain doesn’t have much of a leg to stand on. This was an award, juried by theater professionals, and they chose us as this years’ “emerging librettists.” It was a blind selection (from what I know), and our show rose to the top. I can’t say this was because of my friends’ votes, or because somebody put in a good word for me. I can’t tell myself that this show that I helped create doesn’t have power, and I can’t tell myself that I don’t deserve this.

No matter where my life has taken me, I have always relied on my writing to get me through the day. I wrote stories in grade school. I wrote sketches in college. I started a blog in Louisiana, because I was too broke to do anything that cost money. I wrote dozens of shows in Chicago, and for the first time in my life, after writing for literally three decades, I have now been awarded money for my writing. It is truly an incredible feeling, and I cannot thank the good people at Amas enough for the confidence they have given me and Sangwoo in our show.

I hope that you find this as inspirational, and not self-serving. I wanted to share this feeling with you because so much of being a writer or an artist is hearing “no” or “not now” or “not you” and we hardly ever take the time to realize that these are just learning experiences.

I remember one night in Chicago, I was an opening act for my friend Mic One (rapping), and after my set, I had to rush across town to perform with my Second City group. Mic One’s producer at the time stopped me and asked me where I was going. I told him, and he told me something that stuck with me ever since. He said, “If you want to be successful, you have to choose one. You’re great at rapping, but if you want to make it, you have to give up comedy. Or if you love comedy, you have to give up rapping. If you keep trying to make both work, neither will.” I have lost more nights of sleep to that thought than I ever thought possible, wondering which I should be following. However, whenever I’d try to follow just one, I’d miss the other too much, and find myself falling harder into them. For years I kept them separate, and once I started combining them, everything began to start clicking.

So my only bit of advice that I can offer is this: Do what you can’t not do. Find what makes you happy, and follow it. Don’t care about how varied your interests are. Follow them. Don’t stop doing them just because you can’t make money doing them. Do things that you’re not good at if they make you happy. You’ll get better. When you get good enough to show people, show them. Listen to their feedback. Figure out if it’s helpful. If it is, take it. If it isn’t, forget it. Just keep doing what makes you happy, and don’t worry about not being able to make a job out of it.

I have never been able to earn a living as a writer, but I still do it, almost every single day.

I hope that you can find that one activity that makes you happy, and that you follow it as often as possible. I don’t care if the dog you drew looks like a horse. Show me that picture. And then show me the picture of the dog you draw 20 years from now. I really cannot wait to see that one.

Improv: Not Quite Children’s Play

I have heard improv teachers over the years describe improv to the lay person as something that “gets us to play like when we were children — like when we played house or on the playground – pure, spontaneous and no judgement.” I have even used some of this language in my marketing.

But lately, as the parent of three-and-a-half year old, I believe that image is false.

I have watched my daughter play with other toddlers, and I’ve realized their natural instincts are to want to control the play. It is about conquering versus collaborating. They are toddlers and they want to get their way. I hear a lot of “No” and “You can’t do that.”

The whole idea of “yes and”-ing and agreeing to the imaginary circumstance in a child’s play scenario does not come automatically to these little creatures, as I once believed. And there doesn’t seem to be an expectation to this, even if the child’s parent happens to be an improv teacher.

The other day my daughter had a play date with one of her friends from preschool. And my daughter was constantly saying “No” to her friend’s ideas while they were playing.

“We’re playing picnic!” Betsy would say.

“How about we have a tea party at the picnic?” her friend would say.

“No, there’s no tea at the picnic,” she’d respond.

After one too many “No, you can’t do that” responses, her friend wanted to go home. She was in tears and wanted her Mommy.

I was almost in tears, too. Lauren did a great job of holding Betsy’s friend and calming her down, and it was clear she did not want to continue to play with my daughter.

Who would?

This broke my heart.

I was angry at my daughter for behaving like this to her friend. I also could identify with her friend and I felt sad for all the times I had been told “No” in my house as a kid. Her friend was showing me how I feel when I am shut down by other people.

As painful as this was to watch, it taught me a lot, and it made me grateful that as improvisers we are “trained” to agree on stage to the imaginary circumstances that our fellow improvisers put forth. We are learning the very important skill of negotiation.

As improvisers on stage, we agree to the who, what and where of the scene, and that is foundation for our play. And when we don’t agree to those basic things, the scene sputters and stumbles. We don’t even have a chance to play because we have killed it before we got started.

When you say “no” to someone else’s ideas, it affects the relationship with the other player on a cellular level — the same way it affected my daughter’s friend.

So the whole idea of “yes, and” may not be as innate as I once thought, but luckily, it’s a skill that can be leaned and that’s why to get good at improv, you have to keep doing it because you are literally rewiring your brain to say “yes” to other people’s ideas.

Martin DeMatt and Jay Sukow believed that improv can changes lives. I never really believed that until I became a parent, and I hope these skills are something I can teach my daughter soon.

Want to try improv for the first time or looking for a new approach? Sign up now for Jimmy’s Intro to the Art of Slow Comedy Workshop, happening Jan. 25!

Finding ways to have more fun

We are told all the time in improv just have fun up there and everything will take care of itself.

But what if you don’t have fun in your real life?

Well, then you are screwed.

I am speaking from experience.

I cannot give something away that I don’t have. And when I try to fake fun on stage or in life, I look and sound fakey.

So what do you do if you are miserable and your life sucks?

Well, I can tell you if you want to do better improv, the problem may be that you aren’t having enough fun in your life.

I should know. I have been doing extensive research on this topic for over 40 years, and I have not made any progress until the last couple of years since we had my daughter Betsy.

Now that she’s a little over 2-and-a-half, that kid is at the age when she’s all about play. Everything is about having fun.

She wants to play tipping me over.

She wants me to call her Miss Hannigan (Carol Burnett’s character from the movie Annie) or Miss Hanna for short.

She wants to call me Daddy Warbucks (again from the movie Annie).

She wants her stuffed bear, Chloe, to not only change her stinky poopie, but look at it and smell it. (I have taught her she can’t touch or eat her stinky poopie, because that is what good dads do).

Brooms are guitars.

She makes up songs in the back of the car.

Everything is a game with no rules.

Everything is play.

What she is in life is what I would like to be on stage: She is free.

For me, I believe in the cliché, “Those who can’t, teach.” That takes nothing away from my teaching, I am great teacher who keeps getting better. But it is not lost on me that the reason I was attracted to improv in the first place is, unlike my daughter, I did not get to play as a kid. Yes, I am trying to get my childhood back and help others do the same. I just did it not think it would take being a father to get me there.

I’m not saying you have to have kids to have fun, but you do have to find ways to have fun in your life in order to bring fun to your improv. So, go bowling. Or plan a murder mystery party. Or sing in the car. Or use a British accent when you order your take-out. Just find a way to make yourself play, and you’ll be amazed how much more free you will feel  in your improv.

Learning how to play

You would think as an improviser I would like to play in my everyday life. You would think I would at least know how to have fun and be silly.

I am sorry to disappoint, but I don’t. A couple of weekends ago it became very clear that this might be becoming a problem.

On Saturday afternoon, my wife asked me if I would play with our cat Coco or Moosh-Poosh or whatever name we came up for her that week. I agreed so I would not be accused of not playing with the cat. I really don’t see the point of playing with a cat, now that she is no longer a kitten. It does not surprise me that Lauren is afraid that if we are ever lucky enough to have kids that I won’t want to play with our kids. This is real fear of mine as well. Playing is not in my DNA.

So with Lauren watching I threw a string of plastic gold beads on the hardwood floor so Coco could chase them. It was the most excruciating four minutes of my life.

Then on Sunday, Lauren wanted me to do something with her.

Lauren: Do you want to go on a walk to the park and throw the Frisbee?
Me: (long pause)
Lauren: Come on, it will be fun.
Me: (longer pause)
Lauren: It’s beautiful out.
Me: (longest pause….) Oh, ok.

I did not want to go. This is not my definition of fun. Fun for me is anything I can do while I am horizontal. Taking a nap, sitting by the pool, getting an MRI. If I am laying down, chances are I am having a good time, and if I can incorporate reading into the activity, I am in heaven.

So, Lauren dragged my sorry ass to the park where we started to throw the Frisbee to each other. I say it was a Frisbee, but it was not a real one. It was a promotional one that you get at a bank, which we all know don’t throw as well as real ones. Anyway, we start to toss it around, and all I keep thinking is, “When is this going to be over?”

Most people lose time when then do something that they enjoy. When I am doing something that I enjoy, I am usually checking the time, counting the minutes until it will be done. It does not matter if I am at a movie, on vacation, or having sex. The best part for me is when it’s over. For me, it’s hard to hold onto joy because I don’t believe it will last, so I’d rather avoid having any joy at all.

After 10 minutes of playing catch with the wobbly promotional Frisbee, Lauren says my favorite expression: “OK, that’s enough, let’s go.”

I’m not going to lie. I was grateful to go home into the air conditioning. But I was also grateful that I have someone like Lauren in my life who forces me to have fun and experience joy, because I clearly don’t know how to have it on my own.