Pre-mortem: After falling in love with Spain, losing some creative juice, and debugging my churning stomach — I'm finally back with a bang! 

Below is my hero's journey of venturing into the improv jungle and finding a big part of my creative soul again. I suspect I'll be building on this post in two distinct ways: crafting something similar with my technical path (my brain's "other half"), and exploring what living with an improv worldview means to me.

: One defining moment is the early-stages of my third year of university. As a student who was feeling increasingly claustrophobic from the business & finance bubbles that I spent the majority of time in, I was craving change. This led to a mental reset and a strong willingness to experiment with the unknown/uncertainty. Coincidentally, this line of thinking led me to the world of improv and spur an unconventional career decision to spend 5 months in Tanzania (i.e. a social impact consulting internship). The hunt began. I started and dropped many creative activities and potential hobbies in the same time — salsa dance, pottery, pour painting, yoga, etc.

: Otherwise known as the "supernatural aid", or just simply "mentor". I was surprised where the inspiration came, and it wasn't just a one-shot spark. It was falling into a classic YouTube rabbit hole of comedy-esque content — a medley of 

, Sacha Baron Cohen's unimitable (and improvised) performances as Borat, and a slew of SNL skits. At one point, I made some inspiring connection to my own life: I've always prided myself in being the classic class clown that could put a smile on anyone's first through my goofy personality and clever wit. For the first time, I asked: 

: Enough passive consumption of performing arts content & improv shows slowly convinced me to commit to this new brewing passion. I attended a few comedy shows on Granville Island to get a taste of the sport; it was an easy excuse to invite a friend out on a random Tuesday night. I inquired into the lives of these comedians: their motivations, their journeys, their creative influences. I dabbled in drop-in classes across the city at several comedy houses before gaining the conviction to put some actual skin in the game. I committed to myself: the next frontier would be to integrate improv into a routine, through a dedicated training regimen. 

) was not an easy process. From the first class of Fundamentals I all the way to Advanced I, there were doubts in my mind whether I could even do this. "

You can present seamlessly in a business setting, but you're so bad on stage". 

That would be the type of negative self-talk I would feed myself. I wasn't naturally funny, I wasn't that quick-witted, I couldn't embody convincing or charming characters, I didn't have all these pop culture references in my back pocket... These thoughts crashed around like a tidal wave in my head, and really stifled my confidence as a "comedian" for the longest time. I thought about quitting this journey probably more times than I can admit (~6?!)

: It was a gradual evolution: a growing love for improv as a craft, taught to me by my first (and favourite) improv instructor Ted Hambly. A smart & standup guy (no pun intended), Ted was elegant in the way he navigated the lessons of scenework, blending practical activity with well-intentioned theory. I especially loved how he didn't shy away from going deep and difficult, even to an Improv I class. As I heightened and expanded the depth of my scenework on-stage, so too did I feel a unique feeling outside of the studio. 

A feeling of empowerment, a feeling of elevation

. On the surface, this manifested in better storytelling and increased flexibility in my personal & professional endeavours (for example, my business presentation skills received an improvement spike). 

: In the typical Hero's Journey structure, the hero encounters a woman, who acts as a "temptress" (e.g. love interest) whose main purpose is to distract & derail the hero. Crossing this boundary, the biggest challenge awaits, formally called the Atonement with the Father /Abyss. That's a lot of terminology, so let's unpack this in the context of improv. It was hard to stay attached to improv as a hobby because other life priorities came up: maximizing the last of my undergrad, travelling the world, moving to a new city, starting a corporate job. By themselves, these are also very formative experiences that require sizable doses of care, effort, and attention. You can see where I was pulled in all different directions; truly a chaotic whirlpool of competing attitudes and unforgiving outcomes. My creative child, the one who loved improv, was swept up and washed ashore in a comatose state. The abandonment of the self-generated double-monster: societal expectations & internal tensions created a "squeezing" effect, limiting the colourful oxygen my creative mind craves. 

: This is where the hero finds themselves in a phase of "

" — the point of realization where a greater understanding is unlocked. I consider this point to be right before graduation, where I gradually picked up the pieces of my core identity. Or rather, I 

to pick them up — there was a looming fear that if I didn't manage the transition into the corporate world intentionally, I would lose my entire essence in the process. Yep, a bit dramatic. But at its core, the realization centered around strength of a multivariate identity (fondly called "kaleidoscopic" these days): the idea that being a creative generalist with a weird atypical hobby is a competitive advantage and a barrier against other narratives. 

H. Evolution: It took me a full year after to return to the realm of improv — 

 — and then another year to embrace this part of my identity. When I finally acknowledged myself as an "improviser", I felt liberated. I brought this philosophy with me to varied settings, including job interviews, first dates, and creative circles. I could feel a physical phase shift from Old Sam to New Sam: improvising felt fluid, felt natural, felt whole. As the observer of my own actions, I could abstract out all of the improv principles I applied in-field, everything from heightening  and escalating for dramatic storytelling value, to understanding character subtext as a proxy for human behaviour. I could link these principles with product management tightly, proving how my mindset as "builder" had evolved. I hosted a 3-part improv workshop series for ambitious tech folks in On Deck — as Feynman says, 

. The renewal of intrinsic confidence is arguably the most valuable output out of this exploration, because for the first time in my life, there was a greater calling that led me to a real, raw craft. Obviously there's another long ass memoir post about how my entire worldview now is anchored on the principles of improvisation, but that'll be saved for another time. 

I. Atonement: The toughest part about celebrating this unique creative spirit in me has been my historical reluctance to lean into improvisation hard. This means outside from the context of the stage, I had to integrate this antifragile philosophy into the web of my life. Unfortunately, the first year of COVID made it near impossible to accomplish this goal. The dreary dailiness sapped away the degree of flexibility I had, and my receptiveness to living a life of diversity and variety that I prided myself in before. I started slipping: even in the case where I could share this art with my closest friends on my 24th birthday, my demonstration was short-lived as I didn't have enough conviction to bring people on the full rollercoaster ride. But this too is the destiny of a improviser: rolling with the punches when scenes become borderline unsalvageable, knowing there's always a way out. 

J. Gift: I think this is the most interesting part of the Hero Journey's because it implies continuity and (semi)permanence. When it comes to improv, the natural advantages of increased resilience and comfort within ambiguity spring up as gifts. At an emotional level, my ability to connect is greatly expanded — whether it's the first time meeting someone or it's the umpteenth time, improv is a constant back-and-forth dance that predicates on 

. Making the other person feel seen, feel valued, and feel good. That's likely the primary reason why I usually get the feedback, "I feel comfortable around you" very quickly into any new relationship. Improv oscillates between being a pattern matching exercise and a first principles approach — I know that I need build from the bottom-up using inductive reasoning tools like heightening, platforms, and subtext, but by nature the rules are always bending and shapeshifting. So it's up to me to play in my own sandbox, and share the gift whenever and wherever I can :)  

To be honest, I found it difficult to write my story this way. After reflecting on this process, I realized the hero's journey is an idealistic way of depicting a series of struggles until a cathartic conclusion. Of course, real life doesn't operate in such a rigid fashion. People may go through unpredictable cycles of behaviour, a sinusoidal wave of change and growth. The idealistic version strips away the complex nuance of the day-to-day and the basket of heavy emotions. The story gets reduced into a simple order of operations that you'd learn in Grade 3 Math. It's almost as if assembling some hero's journey were as easy as stacking and toppling dominoes one by one. But to be fair, this type of tale is the easiest to embody — for those seeking an 

 branch of truth, being the hero doesn't seem all that bad.

My hero's journey representation is one version of a journey to finding yourself. Mine is unconventional by all standards, and I've learned over the years to shout that with pride rather than dilute the message with doubt. From the last exploration: narrativizing is a way to find meaning. As cliché as it sounds, we're all the main characters of our own lifelong series, right? 

Then, the ultimate goal is to find a narrative about yourself that resonates with you & make sure everyone knows your story. You're the product, now go optimize for distribution. 


Here's to leading a life as a hero, whenever you most need it and feel it :) 