Shucking the day job and hitting the open road is a dream for many, but for aspiring comedians, it’s a mandatory step to full-time success alongside countless open mics, late gigs at half-empty clubs, and competing with loud drunks and bar televisions all to hone their craft and launch their name. For The Cherokee Effect Comedians, we interviewed four performers who made the journey from 9-5er to professional comedian to learn how they did it and how today’s aspiring comedians can too.
Today we're featuring longtime UCB performer and teacher Will Hines, who has written, directed, and appeared in many web shorts for Upright Citizens Brigade and CollegeHumor and currently works as UCB's Associate Academic Supervisor.
Where were you in life when you first tried comedy?
I was a computer programmer, and when I was 29 I took an improv class. That’s probably the clearest dividing line of not doing any comedy then deciding to do it. But it’s a little bit blurry, because I actually did open mics in a very haphazard way for a couple of years before that, and I was trying to write and submit it to The Village Voice and the New York Press and it always got rejected. But taking an improv class at the UCB in 1999 was the first thing that stuck in terms of doing comedy. I just wanted to meet funny people, because as I got older I was being surrounded by more and more boring, resigned people, and I had been friends with a lot of funny people in college and high school.
So was comedy always in the back of your mind?
Only as a personality trait. My family always identified themselves as being funny, very self-consciously. We’d watch Saturday Night Live and analyze it as if somebody would care about our official opinion, and we would be very committed to our inside jokes, very formally, the way I think a lot of families are. But being a professional was unfathomable to me; I never assumed that I would be talented or lucky enough to be able to do that. So when I took the improv class at 29 it was just to get back in touch with a part of myself, more of a creative-voice, social thing.
How did the improv class feel different than your sporadic attempts at comedy before it?
The only difference was that the UCB community liked me more. I did standup at various open mics like Rebar and Detour and Faceboy’s open mic but I was too shy to ever talk to anybody and unremarkable in what I did. But when I took the improv class, I just made friends with the people in it – we would go out after every class and go see shows at the UCB together so that locked me in.
When did you start to get the feeling that improv could one day be your full-time gig?
I think it was when I was 33 and had been doing it for four years, and friends of mine were starting to go on auditions and submit to shows, which was a concept that was foreign to me – someone submitting for a show was like an exotic concept. Two friends of mine submitted to write for The Man Show – a small-time show, relatively speaking – but just that seemed like the most glamorous thing, like “Wow, you actually submitted for a show.” But they were friends of mine, and I started thinking “Well maybe I could do that – I bet you I could write jokes for a show.” I think I submitted for David Letterman that year, and just submitting for it made me feel fancy. Friends started to show me their packets for shows like Conan and I started to feel like one step away from the people who were doing it. It was all about being friends with people who made me feel like doing it was possible.
Once that momentum started to build, how did you balance comedy with your day job?
I didn’t. I destroyed my day job life, I destroyed personal relationships, I destroyed security so that I would be more available to do creative things. I mean, I didn’t see it that way… [laughs] …but I turned down promotions, I did not spend time at work, I was going to the UCB theater, I was just more interested and invested in spending time with comedy stuff very deliberately.
We could look back and say “Oh, how do you make the move from working at a computer programming job to working as a comedian full-time,” but as I was doing it, all I was worried about was being better onstage as an improviser. Just having a clearer comedic voice – all I cared about, for real, was doing well at that night’s show. I wasn’t thinking of what professional thing would come of it. If I walked onstage at the UCB theater and the audience laughed and my teammates thought I was funny, I was a success. All I wanted to be was good at that. I wasn’t thinking about headshots or auditions. I mean, it started to enter the periphery of my vision when I started submitting to things, but I wasn’t thinking about it really out of lack of confidence. I could imagine being good on the UCB stage because I was there, but I couldn’t imagine beyond that. So all I worried about was that.
It sounds like that ended up being an advantage in a way.
Yeah, it’s kind of serene. I had a sort of serenity vibe – a lack of expectations.
But you still had to pay the bills…and invest in your own performing at the same time.
You just have to drop to your knees and be cool with that. And just assume that stuff will work out – it’s a little bit of a leap of faith. Because when I have the day job I worry about losing it and even when I was saving money I was like “How much to save?” I started thinking “What if I got married and have a kid? I don’t have anywhere near enough for a college education, how would that happen?” But I always just assumed I’d worry about stuff as it became real. I didn’t get married – if I got married, well, me and my wife might start worrying about saving money for something. If I had a kid then maybe I would’ve not destroyed my day job. But I’d be going out with a girl, she and I would break up, and then my improv team would ask me to do more, like that just took over my life more. The girls said go away, the improv team said stay. That happened a lot. So you don’t need that much money to live that way – people like to pretend like they can solve the future, but I think that’s an illusion. People with day jobs are like “I gotta save money, I really couldn’t do it without this,” but yeah you could. I mean you need two months of rent – you need to envision being able to get the next two months’ rent, then you just do it.
And that’s how you do it?
Yeah, but I’ve gotten really bad at it. It’s been years since I’ve sat down and done a spreadsheet budget for a month-to-month. I mean I’m not in debt, but I live small, I don’t accumulate huge expenses, and I just don’t think about money that I get. When I was a computer programmer I made a lot of money for a year and a half then quit, and I saved that money and didn’t touch it then used it as a down payment to buy an apartment three years ago. The mortgage payment is no different than rent, just that initial down payment is really intimidating – that was money I saved ten years ago. That kind of made me feel more secure. Sort of. [pauses] I think I’m a weird case. I floated into it – I never had career ambitions, I never had artistic ambitions. I wanted to meet funny people and get better at improv, and I didn’t care if I had to quit my job to do it. I think because all of life feels temporary. I just don’t worry about it beyond a couple of months.
Do you look to the near future the same way?
Yeah. I’m 42, I started thinking – which I think is way later than most people do this – but I started thinking “I better save up for, like, a retirement, or what if I do want to get married? I’m a terrible prospect right now – how do I remedy that?” I do think about it, but I don’t have any awesome solution. Like I think maybe I’ll book a national commercial or get a part on a TV show and get a windfall for a couple of years and save up like that, but I think the story of somebody working a job for their whole adult life that pays well is a myth that doesn’t occur as much as people think.
For someone who is around improv students so much, do you have advice for what they need in order to consider a full-time comedy career?
Saving enough money to pay rent is good, but that’s not as much as people think. I guess I envisioned myself being a really good performer at the UCB, which is a weird thing to envision, but I did envision that and it did happen. So commit to some vision of yourself – not even the biggest ever, maybe two levels up from where you are, and be comfortable thinking about that, be nourished by that.
Are there certain mistakes you see improv students and aspiring full-timers make over and over?
Well the first one I can think is when people give up early and take themselves out of the game. The most talented people I’ve seen along the way gave up and stopped. So a lot of those people go away if you wait. You’re intimidated by these people who are better than you but will probably be gone if you wait a year, two years. The second thing is depending on money or fame as a barometer of success because those things are out of your control. So I’d prioritize quality of what you do and quality of your friendships and partnerships – that’s very valuable.
So one mistake is depending on the wrong things for validation, and others are impatience, a sense of entitlement like “Oh, I’ve paid my dues, I deserve this” – no, you don’t deserve it. If you’ve gone into any glamor or entertainment industry you don’t deserve any of it because it’s a completely indulgent pursuit; nobody owes it to you. I think also eventually narrowing your focus is a good idea – I’ve had trouble with that, like you try to do everything at once…that’s okay for a while, but the more you focus the better off you are.
What do you mean by that?
Like I have this trouble where I’ll do acting and writing and directing and people say “What are you?” and I’ll be like “I don’t know.” Sometimes I’ve sort of thought of myself as one of those – lately I think of myself as more of an actor than anything and I get more traction. People spread the word about you if you have a simple story.
And you radiate “actor” once you decide that?
I suppose so. You give out signals. For me it was seeing my friends doing things that I thought I could do. But when I was in college I switched majors three times kind of recklessly – I went from chemical engineering to economics to math education to journalism, and graduated with journalism. I was a journalist, then I was a computer programmer, then I was trying to be a writer, now I teach acting. That’s all sorts of crazy switches that a lot of people wouldn’t do. I moved to Cape Cod for a while when I was in my mid-twenties sort of for no reason then moved to New York City, didn’t know anybody here – I might just be insane, when I look back, but I just didn’t need to know what was going to happen.
All that unpredictability almost seems sort of comforting, as opposed to being able to guess your own future.
There’s a good side to it. [pauses] Yeah, my life’s more interesting than I thought it would be. It’s also more harrowing – not only am I not impervious to insecurity, I definitely have Sunday night anxieties of like “Oh my God, oh my God, I am not going anywhere.” I have friends at UCB, like students who are jealous of me like “Ooh, how’d you get on this improv team?” “How’d you get so far?” And I’m like “So far?! What are you talking about?” And I guess I used to think that about people who were performing a lot at UCB. I mean I have a weird life. Like this Monday I did standup at a comedy club, I did punch-up last week for a friend’s Comedy Central show, taught an improv class, auditioned for a movie three weeks ago – and that stuff happens a lot, and none of it has come to any major-league glamorous fruition, but my days are a weird hodgepodge of things, any one of which I would’ve thought was impossible when I was 30. Technology makes it weird – friends will do podcasts and make pilots and invite me and I’ll just be in them, but I’ll forget about them then hear about them later.
So how do you market yourself as a comedian?
You have to decide what to label yourself. You’ve got to give people a simple story that they can spread the word on. Like I said, I think of myself as more of an actor – I can tell my friends I audition for things, then they’ll tell people. I guess because of UCB I have a lot of friends I can tell, and word gets around. Here’s a really weird one – a few months ago I wrote a text-only video game that describes rooms and then you the player type in commands and you get more descriptions, and I told a friend of mine in the UCB LA theater about it and she’s friends with Rian Johnson, the guy who directed Looper and Brick, and he played it and tweeted it today. Isn’t that strange? So that isn’t a career thing at all, but word gets around. If I could just do that about a real successful career thing that’d be nice, but that’s the most effective networking I can think of – just doing stuff you’re passionate about and sharing it with other people who are sympathetic to it. Word gets out.
Or just be awesome. Like when Kate McKinnon came into UCB, everyone found out about her right away. She was really nice and really great and better than almost everybody, and really precise about her performance and really funny, and I think I saw one show of hers and I started talking to all my friends, “Have you guys seen this Kate McKinnon? I saw her show and she’s amazing” and people were like “Yeah yeah, she’s awesome.” So be really good. And people naturally rave about what they’re excited about. Word of mouth is definitely the best advertising.
Twitter is also a good model for this. You can ask your friends to retweet your tweets or just write one they want to retweet, and the latter method is the only one that works. So I think for promoting yourself, give yourself a label that people can describe you as and you’re comfortable with, a goal or direction or desire, and then just do stuff that you like and people hear about it. Jermaine Fowler is a standup in New York who is really good, nice, pretty young – I directed a video he was in a year and a half ago and I saw him doing standup at UCB last week and he walked up to me and I was like “Oh I heard you did a good standup set last week” and he was like “You did?” and I said I was talking to someone, I don’t even remember who – I don’t know. Word gets around. I’d say a lack of confidence and a need to know where I’m going resulted in a faux-zen-like wandering into the New York comedy scene, which has gone okay.
Photo credit: Benjamin Ragheb