Setting Goals and Loving Yourself with Pete Holmes

Comedian, podcaster and creator/host of The Pete Holmes Show, the eponymous Pete Holmes is proof that self-belief can lead to success. Although the show was canceled after two seasons, the perpetual optimist is not letting it get him down.

His podcast You Made It Weird is a one-on-one conversation with a range of guests from notable comedians to spiritual leaders. Aiming to find the weirdness in others, Holmes is at his best while openly discussing his own life in the podcast or standup. His demeanor is never false whether laughing at his own sexual endeavors or discussing spiritual adventures.

I recently sat down with Pete before his shows at the Toronto Just for Laughs festival to learn more about choosing friendships, self-assurance and relating to his fans.

You’re very open about yourself in the podcast and in your comedy, how do you think it helps you relate to the audience?

A hundred percent. Before the podcast you’d have to bring the audience up to who you are and what you are about as a person. If they’re already fans of the podcast, which is like 90% of people who see me do standup unless it’s a club; Friday and Saturday might just be random people, but for the most part it’s fans of the podcast and then they already kind of know where you’re coming from and your perspective. There’s a shorthand so you can jump into it way faster. The first ten years or so of standup you had to have all these jokes that explain who you are, you know what I mean?

Telling your story?

Yeah a little bit, I used to. Even recently I’d have to say “I look like a youth pastor!”

Now they just know.

[laughing] Now they just know that I’m like a youth pastor, yeah, or that I was married or that I am interested in certain things. Before, if you look at my Comedy Central Presents, it’s mostly me being like, “Hello I’m not manly,” “I’m straight but I stand like this,” and “I like these types of things,” and “I’m non-confrontational.” Now they [the audience] just know all that so you can get into it faster and they’ll be more generous. With the podcast, if they really get to know you on it, it’s not them going to see a comedian. It’s silly to say this but I think it’s true. They get the feeling that they’re going to visit their friend. It’s like Pete’s in town or Marc Maron. Well I listen to Maron so if I weren’t a comedian, I would completely understand the feeling of, “Oh Marc is visiting we have to go see him” as opposed to, “Let’s go see if he has new material.” It’s more about wanting to go see that person we know so much about.

Does it make awkward though, with fan encounters where it is kind of one-sided, everybody knows everything about you?

The word is parasocial, that’s the big word meaning one-sided. No, not at all. It’s not like an obvious question; I get that a lot from fans actually. They go, “Is it weird that I know so much about you and that you don’t know anything about me?” I think what’s weird is that I’m okay with it! [laughing] I’m fine with it. It doesn’t make me uncomfortable. You would be surprised how every show there is somebody who has, if not my exact story, very close to my exact story. I just met Dan (Taylor) who’s a Christian college graduate. People come up and tell you how they’re similar, or you helped me through a divorce or a crisis of faith. I just met somebody and they were like, “I lost 150 pounds because of the David Wolfe (#185) or some of the vegan-y episodes.” These people, they do know me and if they tell me the ways in which we are similar then I can know them faster as opposed to being like, “I’m from Cincinnati.” They just start with how we’re similar, and then I can know them pretty quickly.

How do you gain perspective in terms of career or your life? How do you reflect back in order to make yourself a better person?

Hmm, I usually require a little bit of time. I mean, I get credit for talking about my divorce for example but I didn’t really start talking about it until I had been divorced for about 5 or 6 years. So I’m a big believer in giving things time. In fact when people listen to things on the podcast there’s usually a lag. If I say something just happened, it probably happened a month ago, you know what I mean? Cause I take that time to digest it and kind of find the perspective on it.

Like things with the show. When my show was canceled I wrote that letter that went on my Facebook and people liked it. The truth is I had known the show had been cancelled for about a month when I announced it.

So you had time.

I didn’t write the letter but I had time to go through the all stages.

To gather yourself?

Yeah, I gathered myself. Cause you really did go through every discernible – I think I said that in the letter, every discernible emotion. But by the time I announced it I had gained that perspective and was able to share that. I guess the answer really is just taking your time, not rushing.

Where do you find perseverance, where in you do you feel, “I’m going to get through this?”

Well I mean, I think the answer as silly as it sounds is self-love. Believing in yourself and external validations are nice; they are necessary for what I do. I mean you go out and you tell jokes and you hope it’s externally validated. But something that I am a little bit known for is enjoying my own stuff. As long as I am doing the work that I would like to see in the world I believe there are people that one, will enjoy it and two, will probably support me. So as cheesy as it sounds loving yourself and just kind of having faith, just going with the flow when something ends, like the TV show. I look at that as a huge win.

I used to say when Conan gave me the show it’s like he gave me the keys to the Ferrari. A Ferrari? This is crazy and he did! I thought the Ferrari was having a show, but the truth is the Ferrari is this body of work that he helped me make. Which is 80 episodes of a show, that is 40 hours of material which is incredible, and I still have the Ferrari it’s just not going where I thought it was going.

Do you set goals for yourself?

I do, yeah I am a big goal person.

Are you a one month, one year, five year, ten year…

I do it all.

One month, one day?

Oh yeah, I set goals.

I am a list-maker so I am, “Yes I need to do this.” 

Yeah, yeah, yeah! It helps right, it helps you?

It helps me get my thoughts out of my head. If I am thinking, “Oh I need to do something,” if I put it on paper it’s out there officially, okay now you have to do it! Then you aren’t just stewing over it.

Of course! There is a bit of a ritual to that but whatever helps. That is part of what helps me. What I do is, I will freestyle all my goals for 5 or 10 minutes and really be preposterous. Really, everything you could ever possibly want and then you go back and underline the ones that are really, really important to you. Then you go back and apply a time to those. So if you want to be on the cover of Rolling Stone for example, you might assign 5 years for that. But if you want to stop forgetting to brush your teeth you just say, just start doing that now. You’re a grown man! Brush your teeth before bed!

[Laughs] Exactly.

Yeah, I love goals. It was a big goal of mine to do Conan before the time I was 30 and I said that when I was 21 or 22. I was 31 [when I did it], but I got divorced so I always say that threw me off for a year [laughing], but I was 31 and that was a big deal. Then since I most recently set goals I have been really surprised with how, when your subconscious knows what you are aiming for, it kind of activates things. It looks out. It changes what you are looking for.

Maybe if you didn’t have those goals, you wouldn’t see the signs in your way or where the road blocks are in order to go through them.

That’s right, that’s a big thing. I love Joseph Campbell and he talks about following your bliss. Religion uses terms like God’s will and sin, I would so much prefer thinking about the path you’re supposed to be on, the thing you are supposed to do, the thing you are meant to do, made to do. Then I look at sin, whatever that means, just as the things that are impeding it, stopping your progress, stopping your growth. So yeah, I love goals [laughs].

With having friends in the comedy world, do you find there is a healthy competition?

Yeah, that’s a good question. I think at the beginning that’s more of a factor. I’ve said many times on the podcast that you gotta make sure you’re hanging out with people who are going at it the way you want to go at it. It’s also very helpful to have friends that are somewhat ahead of you. I think you need to have a couple different tiers of friends. You don’t have to do this, but this is what I notice a lot of people do. Friends that are doing better than you, then friends that are doing what you would like to be doing in the way you would like to be doing. I’m talking about work friends because standup is such a sparse, spread out world that you do kind of have to find your calling since you’re not going to be put at a desk next to a person.

I found Kumail [Nanjiani] because Kumail was very serious and very, very funny, that was important. Kumail and I are still friends and T.J. Miller and I are still friends. It’s been a decade with all these people. With [John] Mulaney and I, I have been very open about the fact Mulaney was so, so funny and that was part of why I wanted to be friends with him, because I couldn’t afford to have people in my life that I couldn’t… because what are we going to talk about? Movies? I want to talk about comedy. I want to talk about how he’s writing and his process and what’s happening. You do hear about a lot of things. There’s a word on the street sort of sense to things where they will know about a show or they did a show, just simple things. I’m not talking about big auditions or something. I am just saying they will be like, “Have you done Tuesdays at blah, blah?” You know it’s a good show because you’re talking to a good comedian. As opposed to running the risk of someone who doesn’t know about that show, and you don’t know about that show, and neither of you go anywhere. I know that sounds kind of network-y and climb-y.

No, it’s understandably trying to osmosis success.

You’re just trying to get a little group together. You’re all individuals but the more you can band together you help each other out a bit. Now that we’re older, literally everybody that I started with is successful in a certain way. I don’t mean huge, but they’re all doing it and doing it their own way. There isn’t a competition and I never would have said there was a competition. Kumail and I were part of comedy competitions and I don’t remember who won or lost. It was never really like that. If there is competition it is just healthy and good, it never really got ugly.

You hear stories of backstabbing.

Yeah, get away from those people. I know people who lie about having Letterman auditions to get on shows and who do the bait and switch like, “You wanna do a show with you and Kumail?” You get there and Kumail’s not there. [It’s] sneaky, bad things. Get those people out of your life.

They don’t go very far, do they?

No they don’t. They think they do! They get the perception that, “I’m trucking forward, I’m moving ahead.” We’ll never think of you when we’re putting a good show together.

Just get good people who are doing comedy – not to get laid, not to be famous and not to be rich. They’re doing it because they want to do good comedy and then they’re doing it. You can see that potential in them. Be friends with those people and there should probably only be 5 of them, so those are your friends [laughs].

It’s narrowed down already for you!

Yeah, yeah!

In regards to the podcast, have you ever been surprised by your guest’s openness and ability to communicate?

I remember when Mark-Paul Gosselaar (#204) did it, he played Zach Morris. He didn’t know anything about the podcast and within the first five minutes we started talking about his divorce and erection problems and lots of testosterone stuff. I couldn’t believe it. He seemed like he was a fan. W. Kamau Bell (#97) did it. He’s not a huge fan but he is aware of the podcast and he knew how to play the game. He got into it, didn’t resist. But with somebody [Gosselaar] like that, you should be a private person. If you had a DUI people would care, you’re really famous!

Especially since a young age and growing up in that.

He didn’t care, he was ready to go. I would say I am [surprised] all the time. An episode I really like is Science Mike (#201). He was another guy who had never listened to it and two minutes in was talking about heartbreaking, getting bullied stories and personal stuff. People talk about it. They remark on it during the podcast, “I feel like we’re just talking but I know hundreds of thousands of people are listening,” but it doesn’t matter. We’ve found this loophole. It feels good to talk to one person and let all these people listen. There’s a release to it, I know for me there is. At the beginning I used to wake up in the middle of the night really anxious, like what did I do?

What did I say?

Exactly. What did I say? I would sometimes send episodes to people to have them listen and make sure I wasn’t crossing the line or something. Sometimes I would say things about my family. Is this inappropriate? They’re like, “It’s fine, it’s fine.” Now it’s to the point where you can say anything and then that bleeds over into your life.

I used to date girls and it would be really hard for me to tell them I was married or whatever it was that was weird about me. Now it just comes out very naturally. I’m not a sociopath, I don’t just blurt it out but I don’t have any problems showing people the real me, which when you actually listen to the beginning of the podcast, that was a big problem.

Opening up?

Yeah if you listen to those early, early ones I’m not exactly comfortable with opening up. If I do there’s more pop-ups. I’m saying a lot of things like “I’m not a bad person” or “I jerked off before the show I wouldn’t normally do that.” Now I’ll just say it and I find that it’s fine. It was this big experiment. Will people love you for lack of a better term, if you show them the whole picture? That’s why I kind of resent when we’re not allowed to. By allowed I mean groans, boos or people not laughing or worse. When we’re not allowed to show the three dimensions of our being as stand-ups, it’s frustrating and I’m not really interested in that.

When you select podcast guests, is there hesitation now that the podcast has grown and people are more aware that you commit to a deeper level?

Sometimes. I’ve had a couple people just say they don’t want to do it because it is so telling and so in depth. I always understand. There are a couple people, I’m trying to think, I don’t want to out them but there are a couple people I completely understand. They’re like, “I just don’t want to do that.” Ben Schwartz (#198) is one who did it, he was actually a really, really great episode. But he said up top he didn’t want to talk about his girlfriend. He didn’t mind talking about God or comedy, but he didn’t want to talk about his girlfriend in detail.

Then there are people in Hollywood that might be gay or secretly divorced, or secretly married! There are lots of things. I’m fortunate that I don’t have secrets like that. But you could come across somebody that everyone in the industry knows this person is married or whatever the secret is, and they don’t want to come on and pretend like they’re not.

Has your initial intention with the podcast changed?

Oh yeah! At the beginning it was an hour show and just three weird things about the person. Then after a certain point I realized it helped me uncover what my passions are, the things I’m always willing to talk about. It’s truly more than three things. It’s comedy obviously, it’s sex or relationship theory and it’s God. But then there’s subsets of all those. If people want to tell me about something; a lucid dream they had, an astral projection, mushrooms experience, LSD experience, spiritual epiphanies or any of that stuff, it’s not disingenuous. If a fan comes up to me and they’re like, “Can I tell you about this weird dream I had” or “This weird acid trip I had?” I always want to hear it for the most part. Then food – what are people eating, why, and food theory. What is making you feel good? Stuff like that.

Breakups are another thing I love talking about. I love dissecting breakups. I’ve had enough cowardly breakups of my own; that I feel like I’ve learned some lessons and I love giving people a play-by-play on how to get out or finding how they got out. It’s hard to talk about on stage as a standup because sometimes those people are on dates with their abusive partner and I don’t mean physically I just mean emotionally, which can be just as bad…

Looking at it on stage and thinking, “Uh…”

Yeah you just want to scream break up! Break up! Break up! But the truth is, it’s got to come from you, it has to come from you. There’s a certain amount of proselytizing I like to do and I want to tell people you should do this, or this, or do this and it might make you happier, better, healthier or whatever. If it doesn’t come from that person, it’s an AA thing, you need to be the one that hits rock bottom and decides to stop drinking. You can’t go to a meeting just because your friend Earl took you.

Is there a formula for an ideal audience member? Do you want it to be someone who’s listened to the podcast?

It’s a mix. It’s nice to have some strangers there as well. I’ve found in my experience, the best audiences are almost always people that are familiar with you, they’re just going to be the most generous and excited to see you. But then if there are some random people there too, that can introduce some new blood into the mix.

Do you have a preference of club or theatre?There are comedians that are big sticklers of what a perfect room is…

Yeah, Todd Glass! [laughs]

I’ve heard him rant about it many times.

He will! Not really. There are certain rooms I like more than others. I like being able to see the audience and I want the sound to be good so I don’t throw out my voice.

What is your preparation like the day of a show?

When we’re done speaking I’m going to look at my set list and try to be quiet. That’s mostly what it is. If I have a day where I’m already being funny and talking a lot I don’t need it as badly so I will try and just relax on the day of the show, so that when I get out there I really am excited to see the audience. That’s one theory, it’s never the same. Other times I do have a day where I’m just rolling from thing to thing and the show’s great. But today l’ll lay low and then have all my energy for them.  But on a double show day, most of the day is spent sleeping. You eat one meal and do the show, then you do the other show, then you’re done. It’s pretty simple.

To see Pete on tour during one of these upcoming shows, visit PeteHolmes.com

October 16th-17th - Madison, WI at Madison Comedy Fest.

October 24th-26th - Phoenix, AZ at Stand Up Live.

November 21st - Fayetteville, AR - Student Show at the Verizon Ballroom

November 29th - Boston, MA at Paradise Rock Club.

December 11th-13th - Bloomington, IN at The Comedy Attic.

Kaitlynn E-A Smith is a writer, MA fashion grad and (mostly) creative mind. Follow her on Twitter @kaitlynnsmith or on Instagram to look at her cats @kaitlynneasmith

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