Improvisation: An Art and a Gift

A little over a year ago I moved to Chicago for work, consulting specifically. At the time, my expectation — as is the case for most consulting jobs — was that I’d travel to the client Monday-Thursday, rack up hotel and airline perks/rewards, and expense most of my costs, etc, etc. You know, live the glamorous, road warrior lifestyle of an young, ambitious, 20-something year old consultant.

However, my experience did not quite match my expectations. Shortly after moving here, I was staffed on a “local” project. For those not familiar with consulting, “local” typically means your client is either in your home city or the work can be done entirely remotely, or stated plainly, from home. My local project; however, was in the Northwest Suburbs of Chicago.

For me, this meant an 1hr 20mins commuting, each way, Monday-Thursday, weekly. UGH. The point here is not to rag on the firm I worked for, nor complain about my situation, as I am grateful for my consulting experience. But nonetheless, the daily commute and routine work became exhausting both physically and mentally. Quickly, from a mental health perspective, I found myself venturing into a dark place.

A little GIF to ease the mood.

A little GIF to ease the mood.

Naturally, I brought this up with my therapist — yes, I see a therapist #shatterthestigma and together we brainstormed some activities I could pursue outside of work that could help reinvigorate my attitude towards life. Needless to say, given the context of this article, improv classes were mentioned. After some small discussion, it was determined that I would sign up for Improv Level A, an 8 week course, at The Second City Theater here in Chicago.

I would take part in the course, see what I thought and go from there.

Probably you, right now: “FINALLY JACOB! I thought this article was about improv, not mental health.”

The stars of  Whose Line is it Anyway  

The stars of Whose Line is it Anyway 

I’ve always had a fascination towards improvisation. I remember watching Whose Line is it Anyway on ABC Family as an adolescent and being equally entertained and amazed at the craft. I had always been proclaimed to be “witty” and “funny” by my family and friends, but never done anything “artistic” or “theatrical”. I loved sports, not theatre; I was a class clown, not the court jester.

Yet, there I was at 24, at the recommendation of a mental health professional, walking into a bright room, full of 15 strangers from all walks of life, without an idea in the world of the what the next 8 weeks — unbeknownst to me at the time, 9 months — would hold.

Now, I could write an entire memoir/expose that traverses my experience from Level A to E, featuring all the highlights and lowlights, that story of our first time on stage, that one time that one tall guy did that hilarious thing that you really had to be there to see so it wouldn’t make sense in text anyway, etc. But in the age of 140 characters and disappearing photo messages, I’d probably lose your attention, if I haven’t already.

Flash forward those nine months. This past week, I, along with my talented friends of JarFar have completed all five levels (A-E) of the Second City Training Center classes. Eight members from that initial class full of strangers made it all the way through together to the end. We also picked up some rockstar personalities along the way that helped complete our ensemble’s dynamic.

At its core, Improv is more than just making shit up on the fly. It is “governed” by a set of “rules”, which serve as guidelines more than anything else that enable an improviser to be successful. These “rules” can be converted into multiple principles that can be applied to life, business, love and beyond.

Now the juicy stuff. Below are five (six) core principles and takeaways I learned while taking Improv classes at Second City. While I could write about more, I don’t want to lose you.


Are you still here?


Alright, now the good stuff.



1a. The Power of Presence (Be in the Moment)

Those who know me know that I am a consistent practitioner of meditation. While Improv is a much more active practice than meditation, the relation is evident. In improvisation the goal is to create a good, enjoyable scene. However, without a script or a guide as to what might unfold, a good scene can only happen when each improviser is fully immersed in its creation. Every good improvisation you’ve ever seen resulted from the players being present with each other in every moment, reacting honestly to whatever transpires.

An improv scene, much like life, is built moment upon moment. Breaking concentration in the moment creates a disconnect, both from within and to those around us. It is only when we are present in each of these moments that we can capture the beauty being created right before our very eyes.

There is beauty in each moment, don’t miss it.

1b. The Power of Listening (Listen with Intent)

In conversation, we have all been guilty of turning out once we know what our response will be. The now cliché Stephen Covey quote which reads: “Most people do not listen with the intent to understand, they listen with the intent to reply,” holds true more often than not.

Active listening is a core tenant of improvisation and it goes hand in hand with being present. In improv, listening to not only what is being said, but how it is being said can drive forward a scene in unforeseen — no pun intended — ways. In any conversation, in any setting, things like body language, tone, rate of speech and vocabulary are indicators of what the speaker is really attempting to convey. When we listen actively, we not only create the chance to truly hear what the other person is communicating, but we also gift ourselves the opportunity to respond honestly and sincerely.

Listen from a place of understanding; build deeper relationships.

2. The Power of Fear (Fear is Irrational)

After Level C at Second City, all classes are required to perform in a “Level C graduation show.” As a group, we decided to get in front of our stage fright by signing up for a competition which took place exactly a week before our Level C show. I invited friends so needless to say, when it came time for that first group performance in the competition, I was nervous beyond belief.

Doubts and thoughts ran through my head: “What if we look dumb? What if we freeze up? What if we suck?”


None of this dialogue came to reality. How we performed that night is irrelevant because we had done it. We climbed over that wall and landed safely on the other side (for those interested, we actually did pretty well).

Immediately after we walked off stage, everyone’s confidence was sky high; it was evident in our facial expressions and body language. All that internal dialogue was just fiction created by my, or our — assuming we all felt the same way — minds to stop me us from doing something that freaked us out. To stop us from realizing the power, elation and sense of accomplishment that lies right beyond those doubts.

Do not let fear win. Amaze yourself.

A scene from one of our first JarFar performances.

3. The Power of the Arts (Creativity is Everywhere)

As I mentioned previously, I never considered myself much of an artist. And frankly, I still don’t. I don’t have a lick of real musical talent; I cannot draw or paint or do anything traditionally described as “art”.

Yet, just because I am not an “artist” does not mean that I am not “creative”. Since beginning improv, I have found myself embracing my inclination towards the arts and my creative side. I’ve found pleasure in allowing myself to journal frequently — sometimes infrequently — and explore an area of my being that was previously dormant. I believe that everyone has the capacity to create and be creative. Not only do I believe that you can create, but we live in a world where creating content is easier and more streamlined than ever. Not matter what your itch is, there is something to help you scratch it.

The tools to create are at your disposal, start exploring.

4. The Power of You (Your Uniqueness is Your Beauty)

If you have seen the Netflix Documentary/Film “Don’t Think Twice” you may be familiar with the practice of “I’ve got your back”. In improv, no one person is ever alone. In improv, you are an ensemble. You practice together, you perform together, you bow together and you succeed or bomb together. No one person carries an ensemble, every member makes the ensemble.

The core quality that makes any ensemble successful is the unique perspectives that each member brings to the table. Everybody sees the world through their own lenses and it is this quality that makes an improvisation both entertaining and wholly unique, each and every time.

This ideology applies to any group experience, setting or occasion. The life experience that you alone bring to the table is all you need to bring to the table. Your hopes, wishes, desires and beliefs make you who you are. And while I don’t believe that gives anyone the right to defame or harm another, I do believe that it gives you value in this world.

Don’t try to be like someone else. Be you.

5. The Power of Yes (Free Yourself to Let Life Happen)

Lastly is the word, “yes”. If you knew one thing about improvisation prior to reading this post it was probably the concept of “Yes…and”. At the most basic level, improv is simply an act of saying yes to whatever exists, and then adding to that reality. Throughout the A-E classes, this understanding of “Yes…and” as it relates to an improv scene became more nuanced and developed. However, the underlying principle never changed.

Saying yes means you are present and listening to what is being said. Saying yes means you aren’t allowing fear to tell you no. Saying yes frees up your mind to explore the potential of that reality. Saying yes allows you to be you.

I’ve tried to implement yes in my own life outside of improv and the returns have been exponential. Through this mentality I found myself living more freely and saying yes to opportunities or offers I would have previously turned down. The concept of yes has helped me create new friendships, find a new job and ultimately has enabled me to have more fun than I used to. I encourage you to try the same.

Say yes more than no for a week. Be present for what unfolds.


Time to Take a Bow

Let me set one thing straight: doing improv does not make me cool or unique or special in any way. It just adds another layer to this person/son/brother/friend/spirit/soul/whatever that is Jacob Gordon. I signed up — and paid — to take the classes at Second City; all I did was decide to take a plunge into the deep end of a pool. And guess what? I learned to swim. And you can too.

So maybe it’s piano lessons, maybe it’s a dance class or perhaps for you it is Improv as well. I encourage you to sign up, schedule, just initiate that first step. And after you take that first step…

Be present in each moment so that you can listen to yourself and those around you…

In order to push yourself over that irrational cliff of fear and dive headfirst into your creative side…

While illuminating the the desires the make you, you..

Just say yes.

Thanks for reading!

Jacob Gordon