Interview by Jonathan Kersting
Entrepreneur turned comedian Maya May dishes 3 top tips for career-switching during COVID-19.
Maya May was previously a career entrepreneur and channel partner with over a decade of experience in project management as well as product and operations development. Ms. May is no stranger to adversity, and she knows the value of going against the current and doubling down on your dreams. While the story nationally has been focused on the negative impact the pandemic is having on the comedy scene, Maya is performing a virtual comedy tour from her living room. A fixture at comedy festivals and college campuses across the country, she is well acquainted with the challenges faced by young people and recent graduates in today’s job market.
Necessity is the mother of invention, and Maya is an advocate of positive thinking and the ability to adapt in times of crisis. She has three top tips for career switching that need to be considered by those looking to jump ship from their current job, or for those who want to pursue deeply held lifelong interests:
Transcription:
This is Jonathan Kersting, with the Pittsburgh Technology Council and TechVibe Radio, bringing you the TechVibe RAdio One Mic Stand. Today's is gonna be a ton of fun. I guarantee at least three laughs or I'm giving you all your money back. It's as simple as that. We're stretching outside our bounds here a little bit. We've been trying to talk to folks anywhere and everywhere that I think have a cool, fun, inspirational story that can kind of help you get through your day, learn some new knowledge, pick up some new skills. And today we're talking to Maya May, a stand up comedian, which I'm very excited about, who has a little understanding of tech. And it's done some pretty crazy entrepreneurial things in her day. And I'm just so excited to talk to her because I think she has some awesome insight. And just a great way a great vibe of helping us kind of navigate COVID to navigate life in general.Thanks for getting up early in California there and zooming in with me. Much appreciated. Thanks for joining me.
All right. Yeah. Thanks, Jonathan. I love that intro. I felt very special. I was like, Yeah, that's right.
I am helping people get through life. I was reading through some of your stuff. And I was like, this is great stuff. That's why I want to talk to you as far as that goes. Before we put this thing into high gear. What's your background real fast? Cuz I mean, obviously, I think it's always cool. When someone's a stand up comedian. It's like when I could actually like start over again. I think I would try to pursue something with stand up comedy. There's a sign it says I would love to try. It probably fail miserably out of it. Man, I'd like to give it a shot. And you had the you had the chutzpah to go and do that.
Say you can start anytime, like you could literally cut this show right now and go stand out like, yeah, you know, I actually I started at 36.
Yes. It's actually a lot older than most comedians, start. Most comedians start around 20 to 23. And I'm one of those people that's like, I want to do it. I've wanted to do it my entire life. Yeah, I had tried a open mic when I was in my early 20s. And it was it was actually a mixed open mic. And I did poetry because I have an MFA.
Right.
Yeah. So I went to do poetry. And then there was a comedian. And I was like, ah, I was like, Oh, that sounds terrible. But like, I remember hearing it and going,
I think I could do that. And there was a it was a in a bar. There was a baseball game going on. I think it might have been the World Series. So I got up there and I started with my I started to do my poetry, but I got nervous. And then I started rambling, because when I'm nervous, nervous, rambling Wrangler, I'm a Rambler. But I'm a Rambler storyteller. And so I started riffing about a bunch of things. And I was getting laughs And I was like, Oh, my God, I love this. This is so much better than poetry. This is amazing. And then I didn't do it for like, 15 years. What?
Fast forward into 36. So so so what were you doing professionally? Like actually put like bread on the table? And then deciding that, like, you know what, I think I want to revisit this whole stand up comedy thing.
Yeah. So my background is in education and events. I lived in Buenos Aries for eight years. Yeah, it was actually it was it was pretty interesting. So I had a language exchange event there. And so I kind of got into like the education space. Like that's kind of always been like, I like teaching people, right. And so when I moved back to the US, it was in the education space, I was working for a language learning school. And I found myself in meetings, not being able to behave. thing with me, I find myself having to cut up and see if I can make people laugh.
Like it when things were like out of like, if I saw something that I thought was like crazy or weird, I'd comment on it. And I find myself in my head going, this isn't professional Maya, this isn't how this is how grownups behave. And so it became this, like internal battle with myself of like, what's appropriate in the workplace versus who I truly am, like, you know, I just want to be me. And so I ended up going to, there was a wine shop down the street from my office, and I went in there. And I had gone to a few open mics just to watch comedy. This is often and the woman the store manager, I recognized her. And she turns out she was a stand up comedian. And so I told her I was again like, you know, I thought about it. So she invited me to the mic. I went to the mic. I was terrified. I mean, terrified, like in the bathroom, talking to myself in the mirror, like, you can do this. Like I had, like some jokes prepared, but yeah, how do you do to do that prepared? Like, like, what was your what was in your repertoire?
Yeah, I had like about four jokes. And it was really like I was winging it. Like I think it was gonna talk about I was there talking about snow storms and snowflakes like I was like, I think I had this joke. I was like, white people are like snowflakes. I like them individually. I was in Boston. You know what I mean? It was Boston. I think that was one of my jokes. And I got laughs like that joke. Got a laugh at me laugh, man. And, and here's the thing, that's an inappropriate thing to say in the workplace, right? Like, especially in this day and age, you really get strung up.
So I've like, in my mind, I'm like, these things are funny, but I can't see them. And if you take them out of context, it's racist. And I'm like, man, like, run for public office at some point.
Oh, yeah. No, no, this is the thing, though, anybody can run for public office. Now. That's what I'm realizing. I would have known back then maybe I would have just gone straight for office.
Absolutely. So you got jokes. You get up on stage, you said you're terrified? Well, you got a couple laughs with the snowflake joke. So how did it end up?
So it felt good, right? And it also felt like, Oh, is this like a, you know, Beginner's Luck kind of situation. Because, you know, everybody's staring. They're watching me. And I was like, Okay, I think I really like this, I think I want to keep doing this. And so I kept at it, and I but then I became very methodical about it, because I do have that kind of like corporate like background. And we're on a spreadsheet somewhere like Excel, to keep your jokes.
They're categorized, like I have like political race, gender, class, or little drop downs on a little drop down this one snowflakes.
I can do an hour of snowflakes. And so I got really organized really methodical about it. Which I think if you're, I think that's a good thing about coming to something later in life. You have a mindset that's very different than somebody who it's very fresh, and it's new, and that's great for them. But we're able to as older people, and just assuming you're an older person like me, yeah. You one of these days. I'm kind of scared.
I'm 43. I just turned 43. And a lot of people think I like they assume again, like, like early 30s. I would, I wouldn't think you're 43 years old. Like people don't think I'm 48 Thank God.
Like, there's gonna be that. Yeah, so I'm hanging on for dear life right now.
Very cool. So it wasn't just all at once he went and you tried this. And he started realizing I like this, I want to do more of it. So you start making some conscious decision, say, this is what I want to do with my life. And you're able to kind of then make that pivot. from from from from your day job to making comedy, your night day job kind of gets so smooth and simple. And we're trying to inspire some people here to do the thing that you love. Now's the time to actually quit a job because this will pay themselves. It's no big deal. Right?
You know? I did, I started. It took me I've been doing comedy now for almost seven years. Okay, great. And so I in throughout that time, I, as I was getting better and better. And it became more like, oh, like, you look at milestones, right? Like, same thing in project planning. And I said, If I hit this milestone at x point, I'm going to keep going, Okay, because that means I'm my career is going in a trajectory where I will be able to get paid to do this at some point, right? So I was like, Okay, I got into the Boston Comedy Festival. That's a big deal. That was, I think, seven months into comedy. So I was like, I'm gonna keep going. And add opportunities like that came, it wasn't like there was money coming in. Right? There was there's a trick. This is the thing with comedy, like, you can't really make money at it until you reach a certain point. And HBO special, right? I mean, that's where it starts rolling it.
I'm fortunate I do the comedy market, the college comedy market, which is very similar to the corporate market, so there is money in it, but because there's money in it, it's very difficult to break in. And that that kind of for me, was the transition. So I moved from Boston to Chicago to continue with comedy because I knew Chicago has a really great comedy scene. I downgraded to a different job. I had a I was an assistant, and nobody knew I was a comedian, and been at the office. I was a different name for a while, like, I want to have two names. That'd be awesome. Yeah, I love it. I was definitely what was your other name? Keisha Kaplan.
Yeah, I had to come up with that.
So the company I was working for was Kaplan, and my middle name is Keisha. And so it was kind of like to honor those two things. And at the time my ex husband's Jewish so it was like this been like, she's like she's Jewish. What is like, we don't even understand this freaking me out.
Interesting. Wow. So this is obviously this is this, this this slow ramp of kind of getting to where you wanted to go? Yeah, got to where you wanted to go. Cuz now you're doing comedy full time, right?
Yes, I am. And so when I moved to LA, because that's the thing with comedy, you have to either go to LA or New York, truly, if you want to get your career to the next level. So that was like, kind of for me, like, okay, like, I went, I took three months, basically traveling back and forth and doing shows in both places. And that's risky, right. But at the time, I had a job. And I was like, You know what, this is what I'm to do to save up money, do this, and I did. And then I was ready to make the leap. Right? Like you got a plan when you're making the leap, and moved out to LA. And within a month of being in LA, I got my first agent, my college agent, okay. And that again, was like a milestone, like, I didn't screw up.
So far, so good.
Like, they didn't just mess up my whole life. Ah, you know, when we're making leaps like this, there's always the like, Did I just mess up everything, right.
And so got my agent, got my first booking. And the first time I got, you know, I, you know, get flown out. And Funny enough, I just moved from Chicago and my first gig was three hours outside of Chicago.
I could have driven here.
So now I'm going from 75 degree weather in California, to hair, it's freezing snowflakes, everywhere.
Coming up a lot. And and you know, had to drive three hours from O'Hare to get to this school, like kind of in the middle of nowhere. And I remember like when I got paid for that show, and it was more for one show than I made in my corporate life in a whole week.
And I was like, Oh my god, somebody's paying me to be me.
Wow, that's gotta be a pretty gratifying moment, huh?
It was huge because it was what I've been working for. And so to actually have it come to fruition, and to know that all of the sacrifices that I've made and really like just going regardless, like I'm very much like of the like, you just keep going. Like I'm relentless like that. And so I realized at some point, I was like, you're going to have to make it as a comedian, because otherwise you're never going to stop like, you're just going to keep going, going going. So yeah, so that that that right there. What for me was enough to confirm that it was really, it was really time to like, go for it, then.
So I did, I spent all 2019 traveling, touring, performing at festivals, getting invited to my first festivals to perform like having a car pick me up.
That would be boring, inviting. They're like, they're like, man, Maya we need you.
Great, and then talk to my agent.
I'll see if I can do it.
And I and then and then 2020 was supposed to be my year. Right? Like it's gonna be the breakout year. And is in February. And this is a I don't watch TV. So I had no idea what was going on.
Oh, no.
I had not heard of COVID.
I would hold the podcast up to talk about why you don't watch TV and how you didn't know about COVID Oh, my goodness.
So I stopped watching TV in 2004. And I I can say Wow, it was partly because I didn't like having the news dictate how I feel right? Like I'd wake up in the morning, the news would be like, you're gonna feel this way. And I was like, You know what, I don't want my day. I don't want to be a pinball. Right. I don't want my day to be dictated by what's popping up in the news. I want to control my own moods, my own destiny, if I will, if I want to feel sad, I'll feel sad all on my own.
That's why I have to watch three, four new stations in the morning before work. So I feel like I need to see this, this and this. And then realize the truth is somewhere hanging out there in that gray area.
Really, Jonathan, in here, the truth is in here. We all know who we are at our core. And so I was like, You know what, I don't need the news to dictate that to me. And so part of my whole new year's resolution was like literally like, No, I'm just not interacting with the 24 of COVID 20 comes back you might have a little bit of a heads up.
I was in the gym and they have TVs at the gym and I was like what is this thing they're talking about and this is COVID-19.
Anyhow, I always see you probably as much knowledge as the rest of us because they would know who the hell is going on so what the heck out and I and so it was March already and so my gym and everything literally shut down like that next week and then I panicked for a little bit cuz I was like oh my god like how can I travel do comedy if I can't travel economy like this I had all these tours planned good stuff like all sign up for 2020 and everything Oh, Watson get cancelled like one by one like.
Exactly. And so then my adaptation response kicked in. I love it. Yeah, like, you know what, like, you love comedy, comedy can happen anywhere, any place very much like I love the virtual format. My I my agency switched very quickly, they said, do you want to do virtual shows? Hell yes.
I want to be virtual in the year 2020.
A lot of people were like, Oh, that's not real comedy like doing that they need to be they need to be be corrected.
Well, you know, comedians weren't necessarily tech people, right? Like, a lot of your listeners might be tech people. But for comedians, like tech for us is like a little like, ah, for a lot of us. And for me, I embrace it. Because when I was coming up as a comedian, I got a lot of my rehearsal time in my bathroom in front of the mirror, because I couldn't I have a child like, I'm a mom. So I couldn't just go to mics the way everybody else could. So for me, I'm used to performing to silence in the sense that like, on I don't mind. Yeah. Like, my timing doesn't rely on hearing laughs Right. Yeah. Again, you don't need the crowd in order to get the vibe going. So you know how to like put the punch line when you want it to go and all that kind of stuff.
Yeah. And so then all of a sudden, like, as the world started to catch up with virtual as colleges started to realize they were going to be virtual, then all of a sudden, the gigs just started rolling in.
Ah, that makes you so happy to hear that. That's fantastic. Cool. Cool. Cool.
Yeah. So it's in it made it possible to go, Oh, wow. Okay, I'm making more money now. And so in the beginning of COVID, I did I took a corporate job, because I was like, I don't know what's going to happen.
Exactly. Right.
Yeah, with that job, too. What's that? You quit that corporate job now that I did I take that job.
So it's not the kind of job that I could just quit. So I had to so I told them, I would like to transition out so I am transitioning out because I can't leave my team. But that still goes a long way. Absolutely.
I didn't want to be like See ya, wouldn't want to be I'm having so much more fun over here doing this comedy.
Drop on out here. Boom.
Literally, always Mic drop.
Wow, you got a mic there with you. Unbelievable.
That's so cool. Oh, my goodness. So say 2020 was virtually your year. So that's pretty cool.
Yeah, in my tour is called the my MA is virtually there. For like, almost their career wise, and you know, in almost every person. And I think it's been it's been a ton of fun. And I again, like I think the key to 2020 is adapting like, that's what I tell people like you just have to, because it's not really about what you want. At this point. It's about adjusting to what is Yeah. And and figuring out how to exist in that.
Yeah. Well, you got these three kind of key points, that I think these are good, easy takeaways for people. I think they're they're kind of very actionable. When you talk about like assessing the situation, taking care of your environment, and then mapping out a strategy. You give us a little more information on that.
Yeah. So this is almost like the I call it like the things that I've learned about managing and adapting to crisis by being a stand up comedian, right? Okay. The comedian, when we get on the stage, the very first thing that we have to do, and that's virtual or in person is assess the situation of the crowd, right? Because you're stepping into right.
And so that's true, whether you're stepping into a meeting or whether you're stepping into really like any, you know, social event, it's like you survey the land, you look around and you go How is everybody feeling? How do I feel in this environment? Right, right. Right. And by being an it's really about being present, right? That's exactly right. At the end of day, it's called being present, being aware of your surroundings actually caring about what's happening now, right?
As I like, and I don't watch the news. I'm a better person, I really do it and I think it's partly to because I would almost consider the news to be what a heckler is. Right. So you step on stage and if you have somebody trying to distract you from what your goal is, which is in my case, maybe jokes, the news can kind of distract us and keep us. You know, it's like, we want to have our eyes on the prize. So again, it's like being able to say like, Oh, what is my purpose here? What is my intention in this exact moment, and then being able to continuously return to that. So it doesn't matter what's happening in the news, it doesn't matter if somebody drops a drink in the showroom. It doesn't matter if your coworker is saying something off putting during a meeting and frustrating you. Like, that's a heckler. Right, like that coworker that you're like, Ah, you know, just with their vibe or with Oh, yeah.
Yeah. And so from from stand up comedy, I, you know, what I learned is like, you have to let those kind of situations just roll off your back, right? Like, you assess, you adapt. And then you make your plan for where you want to go. And I, you know, we talked a little bit earlier about, like presentations and things. And it's like, that's, when you're a comedian, you get to set your environment, right?
The thing is taking account What's there in front of you? Right,
But we all do. We all get to set our environment, right.
So we're not consciously doing it, though. But I think if you're conscious about doing it, then you can make some better decisions and set it up to your favor, right?
100% 100%. And that's, and that's, to me, that that's the secret sauce in life is remembering day in and day out that this is our life to lead. And we can we can control that we can control it and we can have fun doing it. Like we can have fun doing it because you're not having fun, then man, forget it. Like it's not cool that it's fun. Yeah. So how does that turn into like mapping out a strategy that say you kind of do assess the situation, you're taking into account. So at that point, then, especially if you're a comedian, you got to do this all probably within like a flash to a certain degree where it's like, you have this like, weird part of the brain that you don't know, is working that's doing all this work. And all of a sudden, Wow, now I got I got a strategy. How do you map out that strategy? so quickly?
So I'm sure you know, a lot about systems theory, right? A little bit. I feel like I feel like this audience would know, I don't I don't normally talk about systems theory. But I, you know, when you're a comedian, you have to take in all of the variables, right? each variable is going to affect other the affect the outcome, right, the output. And so when you work that muscle over and over again, what ends up happening is you're able to make those decisions so much more quickly and so much more effectively. All right. So when you encounter a situation, or for me, like if I, you know, was working a joke over and over again, trying to figure out how to get this particular job to work. And I'll change this wording or that wording of this, as you're doing that, and you're kind of seen in real time, what's more effective, in a way, it almost becomes automatic, like that's the new autopilot, right? And so it's a very agile way thrown out. And another great way for us to be able to adapt on the fly, right? And so when I think about planning, like I had planned out an entire year for comedy of how things are supposed to go based on variables that I had at hand that we all until March 13, or the whole day, it was right, yeah.
And then everything changed. And I was immediately even though I just heard about COVID. That week, I was already at the sporting goods store, picking up weights, because I knew my gym was going to close within days. Or you're going to sell out. So I was ordering stuff online. Like I was getting, like everything that I needed to be able to control my and I was able to think like that, because again, it's that constant being present and aware of where we're at at any given point in time. And so when we're planning out our strategy and our future, it's about being able to plan it, but also being able to adjust like, I think sometimes when we make plans we get so stuck in this idea of like, this is how this is going to go. If we're a comedian, I can't do that. I can't go this is how this joke is going to go. Because maybe maybe I'm gonna get a different response. Maybe they're just gonna stare at me. And I'm gonna go Oh, that's not working. I have to quick on the fly.
You did up? Yep. So like being a stand up comedians, a lot like being like a startup technology company where it's like you go in knowing the direction is what you want to sell them what you want to develop them what you want to do, but then the market changes you look, they're not laughing. They're not buying, you got to switch it up a little bit. So it's this kind of like a universal mindset of how to live an effective life, I think to a certain degree, right?
Oh, 100%. And just like with tech, it's not profitable right away.
Exactly. You tend to burn a lot of money for a while, a long while and maybe you're never going to be Make money at it, maybe it's gonna fold.
Often probably will.
But it's about solving problems like and I think, you know, in the tech world, almost everything is about solving a problem. It's like what is the need? You know, that's how Airbnb Airbnb came about. It's like, oh, we're solving a problem of people needing housing when they're inexpensive markets, it's a tripped up the thought, and then look, the whole market changes and now they're having to shift to a different strategy. And so it's so very similar and I tell people this all the time I was like, being the same things that make me good at business are the same things that make me good at comedy. And that's been
there. Yeah, that goes hand in hand man that goes hand in hand. What a fun conversation with you. I just love it. Like it just shows like how often I get to talk to a really cool stand up comedian talking about like, on basically business strategies for lack of a better term. So it all kind of works out been like that. Oh, my goodness, my I'm so glad we got to talk. So where are you appearing next? Like over the over the fall? Like, virtually? Where are you going to be?
No, I am at Jefferson University today. Tomorrow. I'm at Rhodes College. I think Jefferson is I think it might be in Pennsylvania and Rhodes is in Tennessee. It's okay. A lot of times now I'm doing like two shows a day yesterday, I was in two different states. Back to back. It was I was in the same state I was in because it was Mansfield University and University of Scranton, which I think are both in Pennsylvania.
Yeah. All right. Absolutely.
Yeah. So yeah, it's exciting. It's fun to be able to but it feels very like I'm in the matrix like I just like dial into the matrix. I show up I tell some jokes.
Get home, make some coffee. Put the kid to bed. It's all good to go. Thank you so much for taking the time to talk to us here on the Techvibe Radio One Mic Stand your story is super fantastic. So glad I got to meet you. What a double dose of positive vibes today. Love it. 100% my You are the best.
Thank you. Thank you, Jonathan. This has been a ton of fun. I love laughing with people. And so this is the best one. I hope people get some good tips out of this too. I'm sure they will. Thank you so much.
All right. Thanks.
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