Jill Valentine is the executive director of The Chicago Women's Funny Festival at Stage 773 and an original member of The Cupid Players. We talked about how women's roles in improv have changed since she started in 1999, why she likes to make bold choices in her improv, and why she doesn't give herself notes after she improvises.

One thing I have learned along the way is if you want to keep what you have learned, you need to give it away on a regular basis. That’s why teaching others how to do improv is such a privilege.

I am grateful to have gotten to study, work and perform with some of the greatest improv teachers of all time. They were both generous and patient with me and with their time. And I am humble enough that most of the time I continue to learn from my students as well.

So, today, I wanted to give you some more improv teaching tips in the hope you can become the best improv teacher ever. (Okay, maybe I might have overreached on that, but it’s just because I am so excited to share this stuff with you. Teaching improv and sharing my experience still makes me very excited about this crazy art form.)

  1. Let Go of the Results and Your Students Will Have Better Results
    As improv teachers, we think we are in the results business. We think it’s our responsibility for our students to "get it," and if they don't, we think we have failed as teachers. This is a hard one for me, because I often think my self-worth as a teacher is tied to my students’ progress, which I can tell you is losing proposition for all those involved. The reality is my job is to just share with them what I can, and whether or not they “get it” is not up to me.I wish that every student in my improv class “got it” and thought I was the greatest teacher they ever had, but that’s not realistic. The truth is, some students will put it all together in your class and some will hopefully find it later in another person’s class, but when I can let go of the results and take the pressure off myself to be the perfect teacher, the student somehow start to improve.
  1. The Importance of Warm Up Games
    This is something I learned from one of my improv teachers, Martin DeMaat: Warm-up games are essential. Some improv teachers don't see the importance of them. They want to cut right too scene work or throw the students right into doing a Harold. Yes, warm up games take time. Yes, they seem silly and not as important as going right into working on scenes or a long form. I can assure you, however, that by playing warm-up games, students can go deeper and be more grounded in their scenes, not to mention take more risks, if they have warmed up.But another important aspect of warm-up games that people don't seem to talk about is that this is where you can assess the class’s energy for that day. Each day your students will come into class with a totally different energy, and it’s important to adjust your teaching to how they are feeling.

    I remember one time my students came into class all tired and with low energy. Maybe it was the weather or the traffic for some or that they had just had a shitty day at work, but when they began to warm up, they looked like they were zombies. They had brought their day into class, which gave me an opportunity to make an adjustment. I had them walk around the room and talk about their shitty day and how they were feeling. This helped me know where they were at so I didn't need to take it personally and so I could keep adjusting to the energy. And once they had a chance to speak about how they were feeling, their negative energy seemed to lift.

  1. Keep Good Time Boundaries
    Students want to feel that they are being taken care of, and by starting and ending class on time, you are creating a safe and nurturing environment where people feel protected by boundaries.This is something I’m still working on. I am great at starting the class on time. I used to wait until everyone had arrived to start, and then I realized, why should the people who show up on time be penalized? So now I always start on time, no matter what. Unfortunately, I still run over at the end of class, which I know is not good, but I cannot stop myself. But I know the more I stick to the time boundaries, the more respect and trust the students will have in me.

Want to try a new approach to improv, or experience it for the first time? Sign up for Jimmy's Art of Slow Comedy Level 1 class, starting July 12! Use the code SUMMER to get $30 off.

A weird thing has happened to me in the last couple of years. I had realized that I like teaching improv far more than I like improvising. It seems when I am up on stage improvising, I still put a lot of pressure on myself, something I don't do often when I’m teaching it.

In fact, there is nowhere I feel more comfortable than in a classroom or at a corporate training teaching improv. Teaching is in my wheel house, and it’s something I have become really good at. I have secret, just between us: I don’t just like teaching improv; I love it. I love it a lot.

I love bringing people together who don't really know each other that well and creating an ensemble where they feel comfortable enough to be vulnerable, and then be brave enough to use it in their work. This ensemble may exist only for a short period of time -- a couple of hours or several months -- but out of it comes some memorable scenes, and sometimes, even friendships.

I love helping people find their voice on stage as well as off stage. Nothing makes me happier than to see a shy, timid student start to make bold choices on stage or when that same student starts to speak up in the class and share his opinions or ask a lot more questions. And it gives me joy to see a more experienced student step up to become a leader.

I love watching burned out improvisers who have been through the improv ringer or who have stopped doing it for a couple years get excited and inspired about improv all over again.

I love seeing the invisible student, so quiet you forget they are even there, start to get out there on stage more, become louder and take up more space.

I love those students who come into my class bouncing off the walls with energy and talking at light speed learn to slow down and play it real and start to share a part of themselves with us without even realizing it.

I love seeing students constantly surprise me, showing me characters or taking risks I have never seen before.

I love to see them go on and find a theater where they get on a team or get cast in a show or create their own groups or shows. I especially love when students want to become teachers themselves.

I know I have said this before, but when I started out in back in ’80s, if you dared to say you wanted to be an improv teacher or director, people thought you were giving up on your dreams. We all wanted to be performers. We all wanted to be famous.

Well, I am finally brave enough to admit that while I would still like to be famous, being an improv teacher is one of the most rewarding life decisions I have ever made.

Jimmy Carrane would LOVE to work with you! Sign up for his Art of Slow Comedy Level 1 class, starting July 12.
Or sign up for one of his three Art of Slow Comedy Summer Intensives happening this summer. Early Bird Deadline for the class is June 28 and for the first summer intensive is June 24! 

This Sunday is Father's Day, and except for the fact that I already know Lauren’s going to give me a present, I am not really that excited about it. Actually, I am embarrassed. As a father, I feel like a fraud. I feel like I’m not a real father, because in the first year since Betsy was born, all I’ve had to do is rock her to sleep, feed her, change her diaper, and play with her.

To me, this is not parenting. I know, I am crazy. But parenting to me is when I have to start "teaching" them something or setting limits. I think when I can start saying "no” to Betsy and have her understand it, then I will have arrived as a parent.

To me, parenting is about being an authority figure, cracking the whip. Saying things like, “No, you can’t get a treat at the store. We’re going to go home and have dinner,” and having your kid have a complete meltdown. Or yelling something like, “Hey! Quiet down, already!”

It’s also about doing things like teaching how to ride a bike or tie her shoes. Those seem like legit, fatherly things — things that are useful. But just hanging out on the floor and playing with her stacking toys? That just feels like babysitting.

How sad is that, especially for an improviser? Why can't I enjoy this time when the majority of the time is hanging out and playing with her? Why is that not fatherly? Because that is not how I am programmed. I make fun work.

I have been cast in probably one the best roles in my life as a caring, kind, benevolent father, and all I can think is I know a hundred other people who play the part better. People say to me, “How can you not feel like a father? She looks just like you.” It’s true, but trust me, that doesn't matter when you are nuts like me.

I want to be a good father and to be the caring, kind, benevolent father that I’d like to be, but I have to believe I deserve it. And I think that starts with believing that hanging out, being present, and playing are just as valuable as teaching. Here’s hoping I start believing.

Feeling rusty in your improv? Get back into the swing of things with Jimmy's Art of Slow Comedy Summer Intensive. The Early Bird Deadline for the July 15-16 intensive is June 24. Sign up today!

My wife, Lauren, and I were lying on the living room rug playing with our 11-month-old daughter, Betsy. She was playing quietly with these wooden blocks, and I was holding one in my hand when Lauren said, "Give it to her. Give her the block."

As you might suspect I don't like to be told what to do, especially around the subject of play. I was hurt and shut down. I handed Betsy the block, but I held onto the resentment towards Lauren.

In my mind, Lauren was trying to control how we were playing, and this was a good lesson for me, because I cannot tell you how many times I have done this when I have been improvising. Hundreds of times, I kid you not. This doesn't count the millions of times I’ve done it in my life, as well.

If you don't have a clue what I am talking about in terms of improv, let me give you some examples. Have you ever done a scene where you are literally telling people what to do on stage, or where you were talking so much you didn't give them space to respond, or you "steam rolled" the scene with your brilliant premise? Or have you ever played the same angry character over and over again? All of those are attempts to try to control how a scene goes, effectively trying to control how other people play.

Just so you know, I know what I am talking about because I have been guilty of these things for years, and I’d like to apologize to all of the improvisers who have been affected by me playing this way. Whenever I have tried to control a scene, the motivation has always been the same: Fear. Control is just a more PC name for fear.

As I look back at all the times I went out on stage and tried to control the scene, it was usually because I held myself back and was afraid to get out there, or because I was afraid that other people on my team were more talented, getting more stage time, and getting more laughs, and I needed to put to a stop to it.

The great thing about improv is the audience is the judge in all of this. They know when someone is trying to control another person’s actions on stage by “steam rolling” a scene or not allowing someone else to speak. The audience may not be able to articulate it, but they won’t laugh as much or applaud as loudly.

If you are a smart enough player — even if you refuse to listen to your teachers, or directors or teammates — you will eventually realize the audience is telling you the truth. And as painful as is it, it might be in everyone’s best interest to let go of your control schtick.

Play is a sacred thing. There are no rules to it; just ask Betsy. That is what improv classes are all about - trying to relearn the skills that have been beaten out of us over a lifetime so we can play like we did when were 11 months old. Control stops the play. It replaces the joy and spontaneity with fear and anxiety. It makes it 100 times harder to be creative.

If you have been guilty of being controlling as I have been, I get it that habits are hard to break. And if you get anything from this silly little blog, I hope it’s that you have become aware that by trying to control others really doesn’t work — in improv or in life.

Feeling a little rusty in your improv? Get back in shape with Jimmy's Art of Slow Comedy Summer Intensives, July 15-16, July 29-30 and Aug. 19-20. Sign up today!

When people first work with me, especially after the first class, they say things like, "Your class is like therapy," or "That scene was not funny," or "Oh my God, in that exercise you made that person cry."

Generally, people view this as a bad thing. I get it; emotions are scary and it’s not what people are expecting in an improv class.

But the truth is all I did was create a space for people to feel comfortable enough to express those kinds of emotions, and by expressing emotions, the group will bond at light speed. What  connects people faster than someone being vulnerable?

I think all emotions are necessary in comedy, including sadness, so when an exercise or scene causes someone to cry, they are providing a gigantic gift for the rest of us, including the teacher. They are helping all of us who are having a hard time accessing that emotion to be able to feel it themselves.

And if everyone, including the teacher, does not try sweep those messy emotions under the rug and instead embrace them, they have the opportunity to do some pretty cool work.

I have seen it firsthand class after class, workshop after workshop: When someone is courageous enough to access tears and the group gives itself permission to feel the sadness, too, it will always inspire some amazing scenes. Typically, after someone is vulnerable, the group listens better, they are more emotionally connected to each other, and their scenes are truly funny.

Yes, funny. Just because sadness has been expressed does not mean we are going to see a whole slew of melodramatic or heavy scenes. By one person expressing sadness, something gets released for the group, and now the players have more colors of paint to use on the canvas.

They do this without any effort, just by using the natural emotion that is present in the room, they have tapped into a vein of gold.

I totally get that my approach to improv, The Art of Slow Comedy, is not for everyone. I know that I have just as many fans as I have people who think I am bat shit crazy.

But I do think the arts — and especially improv — is a healing profession. If it’s true that laughter is the best medicine, we give out more medication than most 24-hour Walgreens.

And the more we allow ourselves to be vulnerable, the more we have an opportunity to heal the audience and, most importantly, ourselves.

That is why I teach the way I teach, because it gives me an opportunity to heal myself. And God knows I need it.

Looking to go to a deeper place with your improv? Sign up for one of Jimmy's Art of Slow Comedy Summer Intensive, happening July 15-16. The Early Bird Deadline is June 24!

(Who's the funniest one in the pic above? Hint: I'm the one with the sunglasses).

When I started out in improv my goal was to be the funniest one on stage. In retrospect, that wasn’t a very noble one goal. At the time, it seemed important to me for many reasons — primarily, if I stood out from the rest of the group it would prove to myself that I was the star I believed I was destined to be and that I had made the right choice. Every class, every rehearsal, every show was a test to see if I was the funniest one, and if I was not, I felt I had failed. I was devastated. I was depressed.

After having been around the improv scene in Chicago for more than 30 years, I have seen just as many people who are the so called "stand outs" or the funniest ones in their shows go on to have successful TV and film careers as people who weren't.

I have actually been in shows where I have been the "stand out," the funniest one, and it really has not made a difference in my career.

So why was it so necessary for me to try to be the stand out? I am fascinated by this, maybe even obsessed with it, and I’ve come up with a theory based on my own life and wanted to share it with you to see if maybe you had a similar experience.

I grew up in dysfunctional family where I was pretty much neglected growing up. I fought with my other brothers and sisters for my parents’ attention. I was not good at sports, or good looking, or good at school, so I had to carve out a niche among my siblings. So I developed a wicked sense of humor. I was the fat funny one. I had a quick wit and more importantly, I knew how to make my parents laugh. Especially my Dad. No one in my family could challenge me for the title of the funniest one the same way I could not challenge my brothers at being good at sports.

Then I found improv, and I was around people who came from similar families as I did, except they had more confidence and they were funnier than I was. I was jealous and threatened that I would be replaced as the funniest one.

Because being funniest meant that I was loved. It was my whole identity. It was my role in my family and losing it felt like I was being abandoned. As a fat, insecure teenager, entertaining my family and friends was important, because being funny was really the only thing that I got my self-worth from, so I tried to protect it at all costs. Yes, I was a sad clown, as sad as it gets, but that’s who I was for the first 20 years that I was in improv.

Coming to this conclusion — as well as group therapy twice a week, a loving wife, supportive friends and a little spirituality — has helped me realize that I don’t have to be the funniest one to be loved. Having a big, full life outside of improv has made it feel not as important to be the funniest one. And recently, having a daughter has been an even bigger help.

It’s not completely gone, but it doesn’t take over my life as it once did, which makes performing and teaching that much more enjoyable.

If you’ve suffered from the same crazy thinking that I have, I’d love to hear what things you did to overcome it.

Short on time? Come study with Jimmy Carrane during one of his Art of Slow Comedy Summer Intensives! Happening July 15-16, July 29-30 and Aug. 19-20. Sign up today!

In improv, we all want to get noticed and be liked by everyone at the same time. The problem is, it’s hard for those things to coexist. To get noticed, you are going to have to have a strong point of view, and that will piss some people off. And not only is that okay, if you start pissing people off, it just affirms that you have found your point of view.

Take Stephen Colbert. Regardless of whether you agree with his politics or not, we can all agree he has developed a strong point of view. And it did not come overnight either.

If you watched him during his first few months at the Late Show, you could see him trying to find his footing as he transitioned from the bombastic character of Stephen Colbert from The Colbert Report to being Stephen Colbert, host of CBS's Late Show. Could he be as political as he was on his show on Comedy Central? What would be the new point of view of the host?

At first, Colbert was trying really hard to appeal to what he thought a mainstream audience would want. He didn’t know if it was ok to be political, because that might offend some viewers, so we just got a watered down version of the authentic Colbert.

The show struggled a bit at the beginning to find its voice, but when it did, it never apologized for it. It never looked back. Colbert has hit his groove. Now, Colbert is openly criticizing Trump. He’s become the jester who is not afraid to take on the king, and he looks like he’s having a lot of fun doing it, too.

As soon as Colbert wasn’t afraid to piss people off, he found his voice, and surprise, people have connected with him more. Ratings have soared.

Colbert has certainly had to weather more criticism though, even from President Trump himself, who called Colbert a "no talent guy" and "filthy." On the one hand, getting criticized is hard, but on the other hand, it’s pretty amazing that the president of the United States is talking about you.

I get that getting criticism is hard. But the bigger you get and the stronger your point of view is, people will start taking shots. It’s just human nature. Just know that if you’re starting to receive criticism, it’s actually a good thing. It means your comedic voice is getting stronger and people are starting to notice.

When I was little kid, the first thing I ever wanted to be was a stand-up comedian. I loved the idea of standing up in front of a crowd and making them laugh. Then when I was 18 years old, I took my first improv class, and I have been side tracked from my original vision for the last 35 five years.

Improv has been very good to me; I have had a fair amount of success as both an improv teacher and performer. But creatively, nothing has been more fulfilling than when I have gotten back to my original vision of writing and performing my own material.

When I did my first solo show, “I am 27, I Still Live At Home and Sell Office Supplies," all the stars seemed to line up to make the show a success. I worked with the right director, Gary Rudoren; I was at the right theater, The Annoyance; and it was the right topic — kids moving back home with their parents. It ran for a year and half, and I will always look at this as the high point in my career.

My one-man show was really my love of stand-up combined with what I had learned from Del Close: that truth is funny. In those days we would do honest monologues taken from our lives as the "opening" for Harold shows. The monologues were always my favorite part of improvising, even more than the scene work, and they fostered my obsession with truth in comedy. Del believed you could just get up stage and tell a story without having to elaborate on it and you could get a laugh. He was right 80 percent of the time. I became fascinated with how you could be revealing and funny at the same time. I still am.

So far, I’ve done a total of four one-man shows, and I’ve learned that a good show is a result of a good process. With “I’m 27,” I had a great process and a great show. Gary had me improvise stories I had been telling for years. We never wrote anything down. Instead, I just had the script in my head, and once the show was up, we continued to work on it, making it tighter and tighter. When we finally closed the show, it wasn’t the same show we had opened with. It was tighter, and I was a better performer.

And now, more than 15 years after my last one-man show, “Living in a Dwarf’s House,” I’m finally back to writing another one. I’m trying to combine stories about having Betsy, my Dad dying and being on a plane where they thought I was terrorist. And it's the most fun I’ve had in a really long time.

Though I’m writing things down this time, I’m still enjoying the process. I am writing with the help of Lauren and phone calls with Gary, and I feel my confidence coming back to me. I’m getting to do what I loved so much about the first one: express myself in an honest and revealing way. It’s nice to get back there.

This summer, heat up your improv! Sign up for one of Jimmy's weekend-long Art of Slow Comedy Summer Intensives, happening July 15-16, July 29-30 and Aug. 19-20. Early bird price is only $229!

Friday is my birthday. I will be 53 years old. In improv, that makes me ancient. Each year I have the same birthday ritual: I go into a major depression. It usually stems from thinking about how I wish I was more successful, more famous, and have more money — like my friends that I started out with back in the ’90s do. It then ends up with me getting pissed off at God, yelling at him with a fist clenched to the sky saying, "Why haven’t I made it yet?" This is annual ritual is designed to make me feel crappy about myself, and so far it has never let me down.

But this year is different.

Yes, I still want all those things my friends have, but the desire isn’t as burning. I don't feel as desperate. I think the one thing the podcast has taught me is that no amount of success will take away my low self-esteem, self-loathing and self-hatred. That is separate work from my art.

There’s no question that improv comedy has given me a way to express myself, but somewhere along the line I misused it as a way to validate myself. That is always dangerous, because you cannot fix your insides with something outside of yourself. Success, fame and money can’t fill that gaping whole inside me; it’s not possible.

Lately I feel more gratitude for the things I do have. Especially my family — my wife, Lauren; my daughter, Betsy; and my cat, Coco — and all the people around us who have given us so much love and support.

If you’ve been reading this blog on a somewhat regular basis, you have noticed that my own personal forecast has gone from cloudy with a chance of thunder to partly sunny. I owe that to my little joy machine, my daughter Betsy Jane. People say kids will change you, and after ten months, I am realizing they are right, and I am looking forward to even more changes in myself. Being a parent is the hardest, most demanding, most rewarding thing I have ever done. I still question our choice of having a kid, now more than ever since she has started to crawl and it’s hard to keep up with her at 53.

When I look back at my tiny little career, the things that I am the proudest of are the things I either created or were a part of that were built from scratch. I don't why, but they have always been the most fulfilling and rewarding. I think about my first one man show, "I'm 27, I Still Live at Home and Sell Office Supplies," or being part of Jazz Freddy, or starting the podcast Improv Nerd. All things created out of thin air, and now Betsy is on the list. She is my best creation yet.

So, happy birthday to Betsy’s father. She is the greatest gift he could have ever gotten.

Heat up your improv skills this summer at one of Jimmy Carrane's Art of Slow Comedy Summer Intensives! Spots are still available for his weekend workshops on July 15-16, July 29-30 and Aug. 19-20. Sign up today!