When You Know it’s Time to Take a Scary Risk

Original Hamilton cast member Seth Stewart on taking risks even when you’re terrified, and the surprising ways those risks can pay off.

In my favorite episode of the TV show How I Met Your Mother – “Lucky Penny” – protagonist Ted tells his kids how finding a penny on the ground created a seemingly random series of events that caused him to lose out on his dream job. 

Because of a chain of events that includes finding a penny, buying a hot dog, camping in line for a wedding dress sale, and jumping a subway turnstile, Ted misses his flight to Chicago and his dream job goes to someone else. But as the series progresses (spoiler alert!) you learn that the Chicago job was only what Ted thought was his dream job – his real dream job (and dream to add a skyscraper to the New York City skyline and dream to find the love of his life) actually come true because he didn’t get the Chicago job.

It turns out sometimes even unlucky pennies are lucky. 

It’s fiction, sure, but the best fiction is the kind that hits on something you recognize, something real –  a silent rhythm of life that artists turn into song.

If Ted Mosby never picked up that penny he might have never realized his big dreams. And if Seth Stewart still had cartilage in his knees, I might never have seen the original Hamilton cast perform on Broadway.

True story.

Seth is kind of like my penny, and his story reminded me that sometimes the beginnings of the most wonderful things are preceded by the feeling that everything has come to an end. Because something is about to end – you just don’t know right away which thing it is.  It’s a pit, a fog, a darkness – a scary, scary but necessary place.

Seth has had a lot of endings and beginnings; he’s stood on Grammy and Tony stages as part of teams accepting awards on TV while millions watched. He’s danced on tour with artists like Madonna and Jennifer Lopez. He’s  seen himself on a billboard in Times Square. If you’ve ever listened to the original cast albums of Hamilton or In The Heights, you’ve heard his voice.

But what drew me to Seth initially was a 10-second clip from a PBS documentary called In The Heights: Chasing Broadway Dreams, about the cast and creative team of the now Tony-award-winning Broadway show In The Heights. The documentary followed the In The Heights team as they prepared for their Broadway debut. I stumbled on it one day in 2015 while doing research about Lin-Manuel Miranda, the writer of In The Heights and Hamilton (after seeing the now infamous HBO video of Lin I’d started looking for more about this writer who resonated with me so deeply and so instantly).

I had no idea what I was in for when I watched that documentary.

No.

I-

dea.

I had no idea how much tension my heart would release when Karen Olivio said she sometimes feels like a “fake Latina” because she doesn’t know Spanish. I had no idea that because of that documentary I’d shake Lin’s hand one day. No idea that Lac (i.e. Alex Lacamoire) would give me a hug after we talked about music. No idea that Chris Jackson and I would one day talk backstage at the Richard Rogers about how his kid in the documentary was doing today. I had no idea that one day Seth Stewart would bring me behind the metal grates at the Richard Rogers stage door and walk me onto the spinning stage that David Korins designed, the one I’d just seen spin and illuminate artists I’d admired up to that point from afar – mostly through the blaring speakers of a 2007 Honda Accord in Central Florida.

It all started because of my research on this writer guy Lin and Seth Stewart’s torn meniscus.

As soon as I started watching the documentary I was hooked. But then there is this moment where Seth mixes up this yellow powder into a glass of water in his kitchen. He tells the camera people that its glucosamine and that he has to drink it because he doesn’t have any cartilage in his knees because he tore his meniscus. “Ugh…just smelling it makes me cringe.” He drinks it anyway, and that is when my life changes.

Because it is in that moment I know the kind of people I want to interview for this blog, and I know that I want Seth to be one of those people.

I listened to the Hamilton cast album for the first time on a December night in 2015 and its intensity made me feel like it was okay to be relentless.

Relentlessness sounds great when you read it in a book, hear it in a speech, or see it in a meme, but the daily practice of it – going forward again and again after every “no”, pushing through even when it feels like all of your intensity will forever be ignored – can feel pretty terrible. Relentlessness sounds like a motivational meme but it’s really much more like cringing while smelling your glucosamine and then drinking it anyway.

I have found that it’s people like Seth and art like Hamilton that keep my knees moving.

I have a theory, in fact, that one of the (albeit, many) things that made Hamilton so successful is the intensity, work ethic, and generosity of each and every person who brought it to life. I have met more of them than I could have ever dreamed and I get the same impression every time – that these are people who have been relentless. These are people who worked hard even when there was no guarantee that a Hamilton or anything close to a Hamilton would ever be a part of their career. These are people who pursued really narrow crafts against the odds, and kept going long enough, maybe even crazily enough, to get to the point where their art would be shared in cars, through headphones, and on spinning stages.

I think the pain that relentless people endure transforms into encouragement for others, if only they continue long enough. And I can’t help but notice that all my favorite art was born of relentless individuals, often a whole team of them.

Seth is one of those people, and his interview, which I conducted a year ago now, has inspired me more than I think I even knew it would. Whenever I feel the terror of not knowing what is going to happen next, I remember Seth’s story. It reminds me that feeling the pain, cringing at the smell of what is required, does not mean you’re not cut out for what you’re aiming for. What matters is not how it smells to you, but that you drink it. What matters is not that you tore your meniscus, but that you find ways to heal and try again.

When I rewatch the PBS documentary more than a year later I notice a small tattoo on Seth’s wrist and I laugh out loud in recognition, realizing that while I’d never noticed it before (even after meeting him in person) I should have known all along. The inked inscription? “Hard work.”

Seth started performing at the age of 12, and, like Will Wells, he was an athlete first. (As I’ve now interviewed a lot of professional artists, I’ve noticed that there is often an athletic intensity directed towards their craft, especially among those underrepresented in their field.) Seth was a wrestler and football player at his high school in Ohio, but when home he was transfixed by the music videos on MTV – “an ‘80’s baby,” he laughingly describes himself – and he started dancing a lot at home. His parents noticed and put him in dance classes.

It seems like such a simple, everyday thing, parents notice an interest in their kid and put him in a class. Happens all the time. Sometimes it’s just a fun thing to fill a kid’s afternoons or help him make friends. But sometimes, it’s where the magic begins.

In high school, Seth’s parents understood and supported him, but no one else did. “When most kids were going home and already starting on their homework or going to hang out I was going to dance class. And on Saturdays and Sundays when most people had the day off I was going to dance class. So none of my friends really understood like how bad I wanted it. Because when most people were socializing in high school I was not really at the social events. I was training.”

His dance classes were 45 minutes away from his hometown, and by high school dance was more than a hobby in Seth’s life. He was going after it.

Seth’s dad taught him how to set goals, and his advice to Seth for just about anything is: “‘If you want it you gotta go get it!’” This mantra may not be inked on Seth, but it’s in his eyes.

In high school, going to get it meant mowing the lawn to save up to go to New York where he eventually took more dance classes. I ask Seth if he went to New York because there were more dance classes than in Ohio and he laughs and answers, “Definitely.” At some point so many artists make the pilgrimage to the place where their art or the artists they most admire are concentrated. Some make it their home but almost all make it a place to experience and soak up.

After these intense years of training Seth graduated high school with a partial academic scholarship and partial dance scholarship – he and his parents had an agreement that he would try college for at least a year. But after that year, Seth checked his gut and realized it was time to move on.

“I went for a year, and it was great, but then I was like ‘Ya I’m done. I don’t know what’s gonna come after this, but this is not me.’ I had to take that chance.” For Seth, leaving college wasn’t an easy decision, but he knew that “as a dancer your body doesn’t last that long,” and after so many years of training since he was twelve, he was ready to get to work.

I think some of the best things in life come after admitting “I don’t know what’s gonna come after this.” What often follows first, though, is the dark forest, a time of confusion and roaming, but also adventure.

Seth adventured in New York City. He lived out of a duffel bag and backpack, and “would just sleep wherever” each night, including abandoned buildings. “It was the best time of my life.”

His parents weren’t so thrilled. In the documentary, Seth remembers his parents’ reaction when he told them about his decision: “My parents had a heart attack.”

Seth was not blindly following a loosely defined passion or arrogantly leaving school thinking he could easily ‘make it on his own.’ By the time he took this risk he had years and years and years of training. And the year he spent at his college helped him learn the business side of dance. He knew that he would need an agent, and after leaving college he auditioned for an agency and landed a spot.

For six months he did “really small stuff” as he remembers it, and took any opportunity he could to dance for free for his choreographer friends in training.  Then he landed a pretty good gig for a music video shooting in Italy for three weeks. He was excited and packed up his duffel for Italy.

But a week into the job he got a call from his agent who wanted him to go to an audition for Madonna’s next tour. The audition overlapped with the Italy job, and it was in the US.

Seth’s agent wanted him to leave Italy to audition for Madonna. But Seth was not jumping up and down. He knew auditioning for Madonna simply meant he’d be one of 2,000 other hopefuls vying for a few spots – the chances of landing that job were very slim. And it would mean leaving a guaranteed job in Italy – a good one. A paying one. And to top it all off, Seth didn’t have the money to fly back to New York from Italy – he was only halfway through the gig.

But his agency believed in him. They convinced him to audition anyway and said they would loan him the money to fly back and forth, and that if he didn’t get the job he could just pay them back after he got his check from the Italy job.

It was still a big risk.

But Seth left Italy and flew back to New York for a three-day audition for Madonna that indeed began with 2,000 dancers.

Two thousand professional dancers. Who all had taken classes their entire lives.

Seth remembers it well; his audition mentality is one that rings in my ears to this day, every time I find myself in a high pressure situation: “When I went into the audition, I didn’t think I was gonna get it, so I said ‘F— it lets just have fun! I’m just gonna have fun with this. But I’m still gonna kill it.’”

He remembers how good the other dancers were too. “There was such a high bar there with all the other dancers and everybody was so good in their own way. I didn’t feel like I had any special talent, but I knew I could do everything that they threw at me.”

All Seth could do was rely on what was at that point about 10,000 hours of intensive training over 10 years. Big opportunities don’t actually come from one interview or one audition – they come from the years of training and relentlessness that precede that moment. So no matter what they threw at him – tango, hip hop, jazz – he was ready. “The only thing I could think about, besides telling myself to just calm down and breathe, was to just f—ing kill it. Here’s my chance. Go! Just kill it.’”

He perfectly describes what risk feels like when you’re about to jump and first look down. “It’s like the moment before you tell yourself to jump off a cliff, or you’re going to do something crazy. You have to give yourself that last bit of motivation like, ‘Welp here we go –  I’m here now so I might as well try and kill it.’”

He laughs. We both do. Because we’re artists and we know the ‘Welp here we go’ feeling well. We’ve both jumped off many cliffs, and it’s always a treat when you get to the point where you can laugh about it. You have to. Because when you’re in the air laughter isn’t exactly what you experience. It’s mostly terror. Because sometimes – maybe most times – you will jump and land flat on your face. Sometimes you fly, and those are the best, but the only way to fly is to cliff jump a lot; anyone who’s ever flown, even for a moment, has fallen flat on their face so many more times than they’ve caught air. The terror never goes away, you just learn, as Josh Gad so brilliantly explains in the podcast I’m binging right now (Living the Dream with Rory O’Malley), how to “contextualize it.”

Learning that the terror is normal does not take it away, but knowing it’s part of the DNA of going for something does give me that split second of courage I need to jump, even when I’m looking down.

Because no matter how many times you jump, you never know how it will turn out. You never know. This could work out. But this also might not work.  That’s both the wonderful and terrible part. You know you’ll never know for sure unless you jump, but you also know the result might break your heart. You might fall. And it will hurt.

What gets me through is remembering that the hurting does not mean you’re doing it wrong – that the falling might mean you’re doing it right –  and that perhaps it’s simply the price to be paid. (Or at the very least it will allow you to laugh in tandem with people like Seth Stewart.) The hardest parts about the things you’re pursuing are also the parts that will make you the best of friends with the people most successful in the thing you’re going after – because they have all been there and they know that it’s the shared bruises, not awards, that truly bond masters.

Every time it hurts, every time I feel ignored, every time I feel rejected, every time I wonder what in the world am I doing, or whenever I think about quitting, think that writing is a waste of time, think I’m not good enough, think this “no” is the definitive no, I stop and think…but what if this is going to be something I can laugh about one day? What if this is helping me get after it? What if I learn something vital that helps me get closer to what I’m after?

I ask Seth, “Was there ever a time when you felt like the hard work wasn’t paying off?“ And before I even finish the sentence he answers “YEAH!!!!!!!!!” in what sounds like all caps and italics and laughter. His resounding YEAH drips with reassurance that when you’re living the middle of a story it’s okay to doubt along the way.

It was when he was waiting to hear how his Madonna audition went when Seth started to doubt that any of this would actually pay off. The What if None of This Works Out?

“I remember sitting with my dad back in Ohio waiting to hear what was gonna happen with the Madonna audition, and I was like I don’t know, I don’t know what’s going to happen. And I could feel my father feeling worried for me. I was depressed and I could feel him take on my feeling, and that’s when I knew I was in a place of ‘I don’t know what’s going to happen happen.’ That’s when it became real to me that I really didn’t know what was going to happen next.”

Seth felt the full force of the panic of suspension. At this point he’d already run for 10,000 hours. He’d already jumped. What was there left to do? “At some point you just have to be like, ‘You know what I’ve done everything that I can,’ you know? It became an act of surrender.”

The place of I don’t know what’s going to happen is a very real place. It’s that moment when you’ve tossed it all up in the air and you truly, truly, don’t know where it will land, if it will land at all, or if this is where you end, forever in suspension.

It is a terrifying time.

It can be laughed about in hindsight, and it should be, but it doesn’t take away the pain and sometimes panic that lives in that place – that gap between giving it your all and the results. And unfortunately the space you create when you run and jump, the one that opens up new possibility and growth, is also an attractive space to a whole host of other nasty creatures that get in there and shout “What have you done?!?!” which often end up sounding more like “What have I done?” Why did I do this? It feels a lot like a deep wish to go backwards and start over again, a dreadful feeling of lost time and the pain of thinking that you’ve hoped so long for something that will never be.

Seth remembers thinking in that space, “‘I have no idea what I just did. Am I gonna have to move back home to Ohio?’ But that night, I gave it up.” He realized that listening to those voices wouldn’t change a thing, and that the only thing he could really do is let go. If this didn’t work out he might indeed have to move back home and start over (because at this point he was running out of money and had lost out on a lot of money from the Italy job by leaving early). He was ready to accept that. What else could he do? He knew he’d given it his all. He knew he’d killed it. He knew he’d poured out all his training in that audition. He’d given what he had, and he knew the rest was out of his hands completely. He would let it be.

The next day, he got a call:

“‘You got Madonna!'”

They told him he had to move to LA that week. So he moved across the country and then flew – around the world.

After the tour he continued going on auditions of all kinds. He had also trained in acting and was beginning to spread those wings.  Eventually he got a job for this little off-Broadway project, called In The Heights, which would go on to Broadway and win four Tony awards and make me weep on a solo road trip to Tallahassee (see: “Breathe”).

Seth’s voice actually opens the In The Heights cast album: “Great sunlight this morning” he says. He plays Graffiti Pete.

Like everything he does, Seth gave this show everything he had. The show itself also opened with Graffiti Pete – dancing while spray-painting a bodega. Seth opened the show with 10,000 hours of dance, setting the tone, trying not to drop the spray cans.

When In The Heights moved to Broadway, Seth got to the theater early on the first day of rehearsals because he couldn’t wait to see the theater.  When Tommy Kail (an artist whose intensity I also admire; he’s produced In The Heights, Hamilton, Grease! Live, etc.), saw Seth there early he pulled him aside and said “‘Hey, come outside real quick.’”

Seth remembers, “I was like ‘Alright whatever,’ and we’re walking and I say ‘Tommy, where are we going?’ He says ‘Just come on.’”

Seth follows Tommy out into the streets of New York City, into Times Square. There’s a camera following them too for the PBS documentary.

Seth walks down Broadway and stops in shock when he looks up to see why Tommy was leading him on this mystery walk – above them is a seven-story-billboard being put up in one of the busiest areas of Manhattan, featuring Seth as Graffiti Pete – leaning back in a joyous shout to the New York City sky, the In The Heights logo at the top.

I can’t help but imagine the homeless Seth walking beneath that area years ago, looking for a train locker in which to store his backpack for the night, walking where one day he would be on a seven-story billboard as a dancer, an actor, an artist.

Because of the documentary I get to watch this moment as it happens. When Seth sees the billboard everything in his face expands outwards and he immediately calls his mom. “’Yes they’re putting it up right now with the crane!’” he tells her on the phone. “There’s flashing lights around it! You would have a heart attack!’”

I laugh when I realize that when Seth told his parents he’d left college he said they “had a heart attack.” From one heart attack to another. I don’t have kids but I can’t help but wonder if parenting is a variety of heart attacks – some for your kids’ safety and others for their triumphs. How complicated parenting must be when sometimes one has to be put in jeopardy for the other – the heart attacks unavoidable.

As Seth finishes describing the billboard to his mom it almost looks like he’s having a heart attack. He says “‘Hold on mom, hold on”, and he puts his hands on his knees, and lets his head drop, his black hat off center, its rim almost diving into the concrete.

He breathes. Or rather, he looks for breath.

Anyone who has ever worked really hard for something would recognize his posture immediately.

In the middle of getting after something it’s almost all heart break and ‘heart attacks’ and ‘no’s’ and drinking gross powders to keep your knees working. If you endure as far as Seth did, you become used to that part of the journey. You learn how to work through it. You learn how to be patient.  You learn how to contextualize the pain. You learn how to keep going. And along the way, you start to grow comfortable with the discomfort, ready for the rejection part. That’s the part you know most intimately.

Before I started delving into the world of interviewing artists and being an artist myself, I never understood why some artists at award shows could barely eek out a speech because they were so flustered. I mean, most of them were performers for a living so it’s not like they could have stage fright, and most of them were winning an award for their communication skills. Why were those skills failing them now? And it’s not like it’s a complete surprise…I mean…they knew they were nominated. They put on the dress or the tuxedo and walked a red carpet for goodness sakes. Why don’t they know what to say?

But I’ve come to realize that most of the people who’ve gotten that far in their career are so much more used to heartbreak and disappointment than they are recognition. They truly aren’t prepared for a win because the thing that led to the win is their being so focused on their work and enduring the arrows and the torn meniscuses. So when they see their face on a billboard it knocks them into another dimension – their knees crumble in the pure shock and joy of it, the sudden surprising revelation that sometimes, sometimes, dreams come true. Because that’s the kind of a thing at some point you have to leave behind in the dark forest…the dream gets you started but sometimes in the middle the pressure of it can paralyze you; eventually you just have to be all ‘whatever happens, happens, all I can do is my best.’

When you learn to get comfortable with the price to be paid to pursue art, somewhere along the way perhaps you forget that the other moments are possible too. So when they happen, phones must come out, moms must be called, knees must go weak, and heads drop down in gratitude and disbelief. Yellows taxis continue taking other people places, while Seth faces the New York concrete to say thank you, his ‘hard work’ tattoo resting atop his cartilage-free knees.

I find it’s not too long after these big moments that an artist is ready for a new direction, a new dark forest. The best artists don’t get addicted to billboards, they get addicted to growth. And they come to learn that the latter only comes with challenge.

After In The Heights and an intense twelve-year career in the arts, Seth began to transition out of performing. He moved to Florida for an e-commerce start-up company he helped found that was on the brink of success, attracting investors. And 10 months into working intensely on it in Florida, he got a call from George Washingto-I mean-Benn-I mean-Chris Jackson.

Chris Jackson can be heard as George Washington on the Hamilton cast album and was the original GW on Broadway. He was also the original Benny in In The Heights and sings one of my favorite Moana songs.

I was lucky enough to experience Chris’ voice, kindness, and presence backstage at Hamilton, and I swear when you talk to Chris Jackson you stand a little taller – not because he’s so tall (he is), but because when he looks at you it’s like he’s almost willing you to be more, giving you permission to be everything the world tells you you can’t be.

When Chris called  Seth from New York years ago, only a handful of people knew about the Hamilton project. Seth remembers it well: “Chris called me and he was like ‘Hey they’re doing this thing and you should be up here. You need to be up here.’

But Seth was moving on. He was in Florida. He was ready to direct his intensity elsewhere. Seth remembers saying, “‘Chris I’m working on this company – I can’t get up there.’”

Tommy Kail called too.

When I had the life-changing-penny experience of seeing Hamilton on Broadway, I recognized Tommy walking around before the show, greeting a few members in the audience at the Richard Rogers. I laughed as I remembered Seth telling me the story of when Tommy called him in Florida, asking him to come up and be a part of this little off-Broadway project. I also thought about how the day I interviewed Seth on the phone was the day I decided I had to see the original cast perform Hamilton on Broadway no matter what – because talking to Seth confirmed that the connection I felt was real and that the intensity and work ethic I perceived was indeed electric; I had to see them do the thing for myself. I was going to find a way. And I did (with a lot of relentlessness and risk inspired by Seth, as well as some lucky-penny-style magic).

Seth remembers the Tommy call well: “Tommy had called me as well and was like ‘Hey do you wanna come do this thing?’ That’s what Tommy always says, Hey do you wanna come do ‘this thing?’ We’re doing ‘this thing.’ Seth and I laugh a lot at Tommy’s use of ‘this thing.’ It’s such a small and generic word for what would become one of the biggest phenomenon’s of my lifetime. But I love that it starts as just “this thing.” It kind of has to. Otherwise there would be way too much pressure and the thing would never get the chance to exist.

So when Tommy calls Seth, it’s just “this thing.” Because the truth is, it really is. At this point it is not the Hamilton we know today. It is just ‘this thing’ like a million other ‘things’ that creative people are working on with all the hope and little expectation. There has to be joy in building the thing and doing the work and finding the people to bring the thing to life. Because after that, whatever happens, happens.

But Seth didn’t want to do another thing at this point in his career. “I was like ‘You guys I’m down here.’ And Tommy said ‘Well we would love to have you if you can come up here.’”

I can’t help but wonder what it was Tommy and Chris saw in Seth during In The Heights that made them keep calling him in Florida. I can only imagine that everything I learned about Seth from this interview, everything I saw from the documentary, everything I deduced from his “Hard Work” tattoo, shined through every second of the In The Heights process. People with great taste like Tommy want to continue working with great people. People with experience like Chris recognize when character meets talent. I can only imagine they remembered Seth’s Sethness and wanted him as part of this next thing. Seth even deduces, “They knew my work ethic from Heights. They knew what I was about.” Even when you’re not auditioning you’re auditioning. It’s kind of an exciting thought –  that those who do their work to the best of their ability when no one is watching are the ones one day people will watch.

You never know who is watching, but, like Seth at his Madonna audition, the trick is to dance like no one is.

Tommy encouraged Seth to come back to New York. But Chris would not take no for an answer. As Seth remembers (and imitates to me doing his best Chris Jackson/George Washington): “Chris was like ‘Seth get your a—up here!!!’”

I wonder if Chris already knew that this thing was something really special.

Chris reminded Seth that he can always come back to business, but that this was happening right now. Seth remembers even his dad saying “‘I don’t know why but I have a feeling you should go back up to New York.’”

But just like leaving Italy, this was not an easy decision. It’s so hard to remember, but in these moments it’s really so unclear what you should do. In this actual moment for Seth in Florida his business was already going somewhere and this thing could go nowhere – at the time it was just an off-Broadway thing too, and off-Broadway does not pay well at all, especially when it comes to affording living in New York City.

But Seth decided to jump. He told his business partner in Florida he was going to New York but that he still wanted to work on the business while he was there. “I thought to myself, ‘Alright well the people that I trust, Tommy, Chris, my parents are telling me to go up there.” So he decided to trust that and take another leap, letting whatever might happen, happen, but not totally giving up the business either.

But without Seth in Florida, the company dissipated.

I thought about this part of Seth’s story when I watched the Hamilton documentary on PBS (highly recommend!) and producer Jeffrey Seller announces that this thing is going to Broadway. Seth’s smile touches his ears and out of his eyes seep a kind of joy that makes you forget this isn’t the first time he’s heard he’s going to Broadway. When I see that moment in the documentary from my couch all I can think about is how a few phone calls from New York to Florida can change everything, how one thing you think is on a roll might just be a temporary stepping stone to something totally different, and how being an artist means surrendering to things that may go nowhere.

Maybe the path to somewhere is paved with nowheres.

When I saw Seth perform on stage at the Richard Rogers theater in June of 2016 (he was in the original company and the understudy to Lafayette/Jefferson), I saw what 10,000 hours looks like, and I will never forget it. I could feel the collection of hours that every person who helped build the show had invested into all the things in their career up to that point that went ‘nowhere,’ a palpable underscore that I believe is one of the reasons for its success, one so powerful that I was so in it that during intermission the couple next to me asked me hopefully if I was an understudy. I smiled and said no but secretly thought yes, yes I am. Not because I have Broadway talent or aspirations, but because in every way at that time I considered myself an understudy to all that the creation of Hamilton represented; it has been my greatest mentor and teacher during my own middle-of-a-project struggle.

It’s why I did everything I could to see it on Broadway – it was so much more for me than loving the cast album and wanting to see the show. I needed to go to Dagobah.

Hamilton helped me through the terror of the middle of a project, and it would not exist without people like Seth. Because great works of art demand people who take the concept of hard work so seriously that it’s inked into their arms – it requires time and sacrifice and so many people training for so many years in a thing that might never pay off. Shows like Hamilton are a beautiful gift of collective risk and glucosamine powders.

I ask Seth, “If the homeless you could see you now what do you think he would think or say?”

His answer surprises me, and then I realize it shouldn’t have.

He pauses, and then says “My first gut reaction was to say ‘Do more’ but I already do so much. I don’t necessarily need to do more. But I don’t feel like I’ve made it yet. I’m not exactly where I want to be. Yet. I’m not satisfied I should say.”

This kind of dissatisfaction is not inherently negative. It’s in fact quite the opposite of being ungrateful for or unhappy with the present. It’s more about an unrelenting hope of what can be. “My hunger at 32 is still the same as it was as 20, and I’m very thankful for that. Success to me is not necessarily what you’ve accomplished. It’s more about the experiences you can have in your life. And I just want to have a multitude of great and amazing and breathless experiences.”

His motivation builds as we finish our conversation and he proclaims with joyous realization, “I’m not F-ing done!” He laughs. We both laugh. “I’m nowhere near it. I feel like I’m in the beginning. I feel like I’m starting out again. But I’m excited about whatever’s about to come next. I’m excited to achieve and I’m excited to share it.”

A few months after our call Seth Stewart is announced as the next Lafayette/Jefferson principal for Hamilton on Broadway. And you just know he killed it.