Say Yes To A Bigger Career

Most improvisers do improv as a hobby while they work a day job to pay their bills. Many wish that someday they could quit their day job and just do improv, but they can’t really figure out how to get there.

If you want to quit your day job or just make a little extra money in improv, you first have to start saying yes to artistic opportunities that come your way, even if  you never done them before. So if someone asks you to direct a sketch show, and you never done it before, give them a big fat yes, because it is in the realm of your art. On the other hand, if your roommate asks you to operate on his leg, that is a no.

The number one reason people say no to new opportunities is because they don’t want to feel like a fraud. But by saying no, they miss out on learning a new skill, and the future opportunities (and potential new paycheck) that new skill could bring.  Most improvisers are perfectionists, which is not an asset, and unless they can do something perfectly they are often not interested in trying. I don’t have to tell you, anyone who is great at something, sucked at it first.

This can be a hard concept for many improvisers to embrace, especially if they think they already know what they want to be successful at. I’ve often heard people say things like, “I only want to act,” or “I’m a writer,” or “I  only do short form.”

In the arts, if you limit what you do, you will limit what you make. Most successful artists in any field have to cobble together several different things to make a living, and you can’t do that when you pigeon-hole yourself. How may Hollywood actors end up directing, writing and producing? They diversify themselves to have many different skills, all while staying within their art.

I’ve heard that millionaires typically have six different revenue streams. And even if we’re never going to be millionaires, we can use the same concept for our careers. The more sources of revenue you have, the better chance you will be able to quit your day job. My income comes from teaching improv, doing private storytelling coaching, writing books, podcasting, performing shows and acting for the camera.

The Dream

When I started taking improv classes in Chicago in the late ’80s and early ’90s, my goal was simple: To get hired by Second City so I could be on Saturday Night Live. The way I saw it, the path was very narrow. All I wanted to do was act. I wanted to be rock star in the comedy world — the next John Belushi, Bill Murray or Eddie Murphy. If any of my improviser friends even thought about teaching, directing, producing, or writing, we thought they were giving up on their dream. For me, it was acting or nothing.

By the time I was in my 30s, most of my friends had figured out that to be successful, they had to give up on their dreams of being in front of the camera in order to make a living in the comedy world. Many of them were moving to New York to write for Conan and SNL. For them, it seemed natural to go from being a comedy performer to a comedy writer, but not me for me. I was still holding on to the hope that I was going to make it as an actor. I wish I could have learned from their example, but unfortunately, I don’t work that way. I learn through pain, years of it.

For me, my dream had become a nightmare. By the time I was in my 40s, I was single, teaching one improv class a week and living off credit cards and spending a lot of time in my bathtub listening to Howard Stern. I was a starving artist who was on the verge of becoming a homeless one.

Then things started to change when I started to “yes” more.

Saying Yes

I was very familiar with saying “yes” on stage doing improv. The concept of “Yes, And…” is simple in improv. When you are on stage improvising, you want to say “yes, and…” to other people’s ideas and add something to it.

But when it came to work, I was not nearly as good at saying yes because I was very narrow-minded in what I thought I wanted to do. But finally, when I was in enough pain and desperation,  I started saying yes to more different kinds of work. And what do you know? The more I said yes to opportunities that came my way, the more work I got and the more money I made. I was becoming a Renaissance man for hire.

People started asking me if I could coach them in writing a screenplay, or direct their one-person show, or teach a podcast workshop. And I started saying yes, even though I had never done any of those things before and, frankly, didn’t think I had the confidence to pull them off.

But you know what? I said yes anyway, and I trusted that if I got in over my head, I could ask for help from other artists in my field. And 83% of the time I was better at it then I thought.

Four Star Comedy Festival

One of the biggest things I said yes to that I had never done before was to co-produce a comedy festival.

The idea came from my friend, Ben Capraro, who is filled with a lot of energy and passion for comedy. In December 2011, he told me about his idea of doing a one-day improv festival at Chicago’s iconic Navy Pier with a rather large budget (in improv dollars it seemed like millions). His idea was to have improv workshops during the day and then performances from four different improv groups in front of 300 people at night.

He wanted to know if I wanted to be a co-producer.

I had never produced something as big as The Four-Star Comedy Festival before. Even though I felt like fraud and suffered from a case of imposter syndrome, I kept saying yes, just to see where it would go, secretly hoping it would fall apart.

Thank God for my wife, Lauren. She kept saying “Shut up, and keep doing what’s in front of you.” Well, co-producing was in front of me, so I decided to do it, even though I felt I was over my head. We asked for a lot of help along the way and got it, and when we finally put the festival on in October 2012, it was a big success.

And when it was all over, I am glad I did it. It’s rare in improv comedy in Chicago to get paid as much as we paid the groups that night, and it’s even rarer to get paid as much as we did to produce the festival. And most importantly, by saying yes to this opportunity, even though I wasn’t sure I could do it, I gained more valuable skills that helped me to diversify.

Teaching Improv Online

One of my main revenue streams is teaching improv. I have been successfully filling my improv classes and workshops for the last 15 years. I have to market my ass off to do it, and I often worry that my classes won’t sell out, but usually they do.

But when the pandemic hit in March, I did not know what I was going to do. We could no longer meet safely in person, and I had a master-level class already filled. I kept pushing the start date back because I didn’t know how I was going to teach the class. I was panicking.

Second City had moved to teaching online, using Zoom, which is a video conferencing service, but I wasn’t sure I could do that. I was skeptical. I was resistant. I was terrified. Just ask Lauren.

So, before I could say yes, I started doing my research and started calling my friends who were already doing what I thought was impossible — teaching improv online.

Kevin Reome, who teaches at Second City, spent over an hour on the phone going over his lesson plan with me, and reassuring me that doing improv online was actually fun. Another teacher there, John Hildreth, gave me some advice and some games I could try online. The next day, Noah Gregoropoulos e-mailed me asking me if I would like to improv on Zoom with another old friend of mine, David Koechner.

Noah was going to teach his improv class online for DePaul University and wanted to get comfortable with the technology and record some scenes to show his class.

When I got the e-mail, I was like “Fuck you, Universe, for giving me such a clear sign.” So I said yes and tried it.

On Thursday, the three of us met on Zoom and Dave and I did a couple of scenes and they were solid. Noah recorded them and played them back to us. When I saw the quality of work that can be done on Zoom, I thought, “I can do this! It will not replace doing live shows or live classes, but it’s a great alternative right now.” It made me excited.

After that, I asked a couple of friends to do a practice session with me before my class on Monday and called Noah to help me with the technology part, which intimated the hell out of me.

By Monday, I was all in. I was scared as hell, but excited too. I taught my first online improv class to a group of very experienced improvisers, and I was impressed at how agile they were with the technology and how quickly they were able to adapt to the new medium. Their scene work was outstanding and they guided me  through the technology when I hit a bump.

When the class ended, a couple of people mentioned that they had been skeptical, but were really pleased with how it went.

“Me too,” I said. “Me too.”

I have been teaching on Zoom for six months now, and I continue to stay financially afloat even in these uncertain times — all because I said “yes.”

Once you get good at saying “yes,” you will also have to learn to start saying “no.” Next week I will talk about how saying “no” is an important part of making money from you art, too.

Interested in trying a new approach to your improv? Check out Jimmy’s Art of Slow Comedy Fall Intensive, happening Oct. 24-25. Only $129 if you register by Oct. 10! Sign up today!

Want a Bigger Career? Ask For What You Want

As you’ve probably learned by now, improv is not an art that really makes people a lot of money. Very few people make a living as an improviser. Most people are lucky if they can get paid a few bucks for doing a show.

But that doesn’t mean it has to be that way. Many artists (which includes you), CAN and DO make money from their art. But in order to become successful and get paid what you’re worth, you have to learn how to ask for what you want.

The most common “ask” in the arts is for money. Artists don’t like to talk about money, let alone ask for it. We have been so beaten down with years of performing for free and not charging for our work that what we do has lost its value. We are told real artists do their art because they love it and never do it for the money. We are so used to taking crumbs, that when an opportunity comes up where we could actually make money, we still take crumbs, when in some cases we could get the whole pie.

Money is the most common “ask” and certainly the scariest, but there plenty of others: asking to audition for a role in a play or a movie, asking for advice, asking your actor friends to do your play reading, asking someone to give you feedback on your scripts, asking a friend if they will talk to their agent about representing you.

Asking for what we want can be terrifying. Typically, artists avoid asking for what they want because all sorts of messages from childhood will come up like, “Asking is bad,” or “I don’t want to bother them,” or “They won’t like me,” or “That will piss them off so much that I will lose the job.” And what sane artist wants to go through any more rejection than they need to?

But asking for what you want is essential to having  a bigger career and checking account.

So how do you get over your fear of asking and start doing it? You have to start believing you are  not doing something wrong by asking, actually it’s a good thing.

You have a right to ask for you what you want, just like everyone else has a right to say yes or no to your request. It’s ok to ask for more money, a bigger advance on your book, or green M&Ms in your dressing room. Just like it’s ok to for them to ask you to do the show for free, get a smaller advance, and ask you to provide your own M&M’s in your dressing room. As my friend Darryl likes to say, ” Your just transacting business.”

You have just as much right to say “no” as they do. They can take of themselves and so can you.

But I want to warn you that the more you ask for what you want, the more you will get what what you asked for, and while that may seem like a good thing, when you actually start getting what you want, it may be scarier than you think.

Jimmy’s Ask

I was once cast in a live industrial show — an acting job for a corporate client — where four of us had to play the guys from the SNL’s Da Bears sketch. I had auditioned for it, and it went extremely well. That afternoon, my agent told me she was going to ask for $1,000 for me. As I hung up the phone, I immediately felt anxiety and fear because I did not ask for what I wanted. I was hoping the agent was magically going to take care of me. I was setting myself up for a resentment.

So I called a friend who suggested I call the agent back and tell her what I would like to be paid. I was scared shitless, but I did it. As my voice trembled, I said, “I would like to be paid $2,500.”

My agent seemed stunned, and balked a little at it. The next day, she called me back. Her voice seemed somewhat flat and professional (I think she was in shock), and she wanted to let me know that the client had agreed to the price.

My agent was also representing another actor who was kind enough to give me a ride to the gig, which was out by the airport. On the ride back to the city, we started to discuss what we were getting paid, and she said when our agent had originally called, she said the job was only paying $1,000, and then the next day she called and said it was $2,500. It never dawned on me that by me asking for more money that I would be helping my other cast members to get paid more as well.

No One Is Going to Take Care Of You Except You

Learning how to ask is important because we have to learn how to advocate for ourselves. No one will take care of us until we start taking care of ourselves first.  Once we start doing this people will becoming out of the wood work to work with us.

This is something I need to keep re-learning. Whenever I’ve run into problems with people over money, such as the theaters I have taught for or performed at, it’s always the same thing: I have looked to them to take care of me, thinking they owe me something. But really, I had it backwards. We are adults, and it’s time to stop looking for others to take care of us and instead for us to take care of ourselves by asking for what we want. If we do that, we all win.

Each Gig is Different

If you want to go from starving artist to a thriving one, you have to stop always taking what is offered to you just to be liked. But you also can’t become so demanding that you are always drawing lines in the sand and walking away. Believe me, I have done plenty of that and the only person I was hurting was me and my checking account.

Instead, try to be flexible. Go into every situation with an open mind and try to evaluate what would work best for you. For example, I know if I am doing private coaching for six college kids for in improv group in Omaha, there is only so much they can pay me. And if I am going to do a corporate improv workshop for a pharmaceutical company, I may charge ten times what I would charge the college students.

A good rule of thumb that I use when I set a price for something is to ask myself what amount would be too low that I would have a resentment if I did it for that price. You can also ask yourself what price would be so high that you would feel shame if you charged that. Somewhere between those two numbers is a good price to shoot for.


Want to try a new approach to improv? Jimmy Carrane’s Art of Slow Comedy Level 1 Class starts Sept. 16! Sign up by Sept. 2 to save!

How improv can help your career

I recently got a call from an old improv friend. He was calling me to tell me that he had gotten a new job.

He was excited, almost giddy. He told me that he was now the head of human resources at a prominent TV station. And he said, “I can thank improv for this new job.”

I was a little confused. So, I asked him to explain.

“In my last job, I was a trainer, and I was hired because of my improv experience. And this job I got because of my training experience,” he said.

I think there’s this idea out there that if we don’t get on SNL, or land a job writing for Colbert, or worse, if we move back home and stop performing altogether, we have failed in improv. But the truth is, improv can be a tool that helps us develop all kinds of muscles and skills that are valuable in life, even if we don’t end up “making it” in comedy.

Improv teaches you how to be comfortable speaking in front of people, how to collaborate well with others, how to be more creative, how to have more confidence. It teaches you how to be a better listener, salesperson, writer and communicator.

Hearing about my friend’s new job made me think about how many other improvisers I have known who have landed great jobs in un-improv related fields because of their improv background.

We rarely hear those stories, but they are just as important as the ones about the people who get a spot on SNL.

I am grateful my friend called me and shared his good news with me because I need to remember this not only for the students I teach, but more importantly for me.

Because even though at 55 I have been fortunate enough to make my living by teaching and improvising on a regular basis, I still don’t know where I am going to end up. I actually hope there is something great in store for me in my career that has nothing directly to do with improv, yet has everything to do with the skills I’ve learned through this art form. I can’t wait to find out what that is.


Feeling a little stuck in your improv? Go deeper into your scene work in Jimmy’s Advanced Two-Person Scene Tune-Up, happening June 1. Save $30 when you sign up by May 18!

What’s Next?

Recently Saturday Night Live hired two very talented, hard-working and funny cast members from Chicago: Chris Redd and Luke Null.

When Chris Redd got hired, he had moved to LA and was getting parts in movies and TV shows and had even done his own stand-up special, so he was already getting noticed. But Luke had more of a Cinderella story: He got hired from a showcase at iO Chicago.

Although many people in the Chicago improv community are happy for both Chris and Luke, when something like this happens, it also tends to cause people to feel sad and depressed and wonder if they should just give up on improv altogether.

For those of you in the Chicago improv community who also auditioned for SNL in that same showcase, or those who simply knew Chris or Luke from around town, I want to let you know that just because you didn’t get the gig doesn’t mean you don’t have talent. It maybe be cliche, but everyone has a different path.

This is a concept that has taken me decades to understand. For 25 years I would be jealous whenever one of my friends got big-time success, or really any kind of success. It would make me question my own career path. I would ask myself: “What’s next for me? Where’s mine? What am I doing wrong?”

If you’ve been doing the same thing lately, I have something important to tell you: You have done nothing wrong. Just because someone else succeeded doesn’t mean you won’t.

You are wonderful, and special and unique. Honor that like you would your choices on stage and listen up: Your career path will not look like someone else’s. The hardest lesson to learn is to stay in your own lane in the pool. We think that we “should” want what other people in our improv community want, or we should get what other people get, and if we don’t there is something wrong with us.

There is nothing wrong with you.

Following other people dreams for me has always ended in a nightmare because I never got to find out what I really wanted. There was a long list of things I was “supposed” to want because that is what my friends wanted. Then when my friends got a writing gig on a network late night talk show or big role in a movie, I felt despair. “What am I doing with my life?” I’d moan.

This was crazy. I was crazy. The only thing that really worked for me was when I did the next right thing. The thing that was right in front of me. And those have been the times in my life where I have been the most creative and felt a sense of purpose. For me, it has been these times of despair and self-doubt that have lead me to write another one-man show, or write a book or create a podcast.

If you truly believe you are an artist like I do, these times of self-doubt are golden opportunities that can help your art and your vision for yourself evolve into something new.

These times of questioning are important times of growth. It’s like in adolescence when your voice changes. It sounds awkward at first, but eventually it gets richer and deeper. Asking yourself “What is next for me?” is both a scary and exciting place to be for an artist, but the change will be good.

And that is where I am today. I really don’t know what is next for me. I am afraid that being married with a baby at 53 is different than when I as 27 and living at home and selling office supplies. Back then, I turned my experience into a hit show, but now I wonder, what am I meant to do next?

At least today I know that all I need to do is stay in my own lane, because if I don’t I will drown to death. I just have to trust and do the next thing right in front of me. And I can truly be happy for other people’s success because I know I am on my own path.

Are you an experienced improviser looking for a new approach? Check out Jimmy’s Art of Slow Comedy Level 3 class, starting Oct. 25, which ends with a performance for family and friends. Early bird special ends Oct. 14!

How to land your comedy dream job

Today more than ever the opportunities for improvisers are abundant. There are so many classes to choose take, groups to be a part of and places to perform — which can be a blessing and a curse.

That’s why it’s important to map out a vision for your career before you get in too deep.

Do you want be on the writing staff of The Daily Show? Perform on Saturday Night Live? Tour the country as a stand-up? Direct, produce or teach or be a screenwriter or start your own improv theater or just be a great improviser? All of these are great goals, and to get there, it helps to be clear about your vision.

For me, creating a vision isn’t just about thinking about where I want to go. It’s about writing down my goals and getting suggestions from other people about how to achieve them. It’s like creating a road map for your improv career. Just know that it will never be a direct route to your vision. You will find obstacles and opportunities all along the way, and that is the fun part.

I did this when I was creating Improv Nerd, and I have to tell you that the results have turned out pretty well so far. About two and a half years ago, I sat down with a couple of friends and came up with the idea for a show where I would interview improvisers. They suggested that I improvise with the guests, but I was reluctant, probably because I was scared. But I listened to them, and now that is one of the things that really makes the Improv Nerd podcast stand out.

Here are three steps to take to create your vision:

Step 1: Ask two trusted friends, and not over beers, to sit down with you and ask you this question: “If time and money were no object, meaning you had at least $10 million in the bank and all the time in the world, what would like to do?” Spend about an hour or so talking about your vision while your friends write it down in as much detail as possible. Don’t get caught up in how it’s going to come true. That’s not your business. It will never happen the way you think it will happen anyway. Just get your vision down.

Step 2: Ask your friends to give you simple action steps to start working towards your vision. They should give you about five to ten things that are fairly easy to achieve. If your vision is to write for the Daily Show, for example, and you haven’t written in years, one of your action steps may be to write jokes for five minutes a day. Another action step may be to look into classes that can help you put a writing packet together. The action step isn’t to take the class, it’s simply to look into it. Remember to be gentle and keep the action steps realistic. They are there to build your confidence.

Step 3: Now here’s the hard part. Start taking the actions. For me, I can’t take any action alone. The problem is I think I can, but then I end up taking no action at all. To make it easier, call a friend before and after you take each action step. If one of the action steps they give you is to watch The Daily Show every night for next four weeks, ask your friends if you can call them and leave a message after you watch each episode. This ensures that you’ll actually do the actions steps. Some people call this accountability.

Even if your action steps are very small, you’ll start to feel a shift just by taking them. Feelings may also come up, some positive and some negative. As I moved toward my vision with Improv Nerd and accomplished more, feelings of anger and sadness came up, not the joy and the excitement you would expect. If this happens to you, don’t let those negative feelings stop you. They’re growing pains, and a sign that you’re heading in the right direction.

You may also find that as you move toward your vision that other things that you thought you wanted don’t become as important. This is ok, too. Your vision is flexible. For me, as I moved forward with Improv Nerd, I realized that auditioning for TV commercials wasn’t as important to me as it had been before, and I’ve decided to let that part go.

“Hey, Jimmy, but what if I’m just starting out in improv and I don’t have a vision?” That’s ok! Just know that in a couple of years you might want to have a vision for yourself. For now, let fun be your guide. Pay attention to the things that you do in your life that you enjoy doing and make you totally lose track of time, and know that those things might be in your vision someday. I know for me, when I teach and write I have such a great time that I am unaware of the time – a signal that those two things are probably part of my vision.

Remember, this vision is not etched in stone. It’s a starting off point to help you get some clarity on what it is that would really make you happy in your career. Yes, it may change, and just like any good improv scene, you gain more clarity as you continue making discoveries.

OK, here is your first action step to help you get started on your vision. (Kind of scary isn’t it?). Let us know what you vision is in the comment section of the blog below. What would you like for your improv career if time and money were no object? I look forward to reading them.


TWO-PERSON SCENE WORKSHOP, JAN. 4: Good two-person scenes are the foundation of any good show. No amount of cleverness or fancy editing is going to fix bad two-person scenes. To polish your two-person scene work, sign up for Jimmy’s one-day workshop. Spots still available! For more information, click here.

FUNDAMENTALS OF IMPROV, JAN. 6-FEB. 10: Learn Jimmy Carrane’s unique method of the Art of Slow Comedy. Suitable for those who have never improvised and seasoned improvisers looking for a new approach. For more information, click here.