542 - When to Reboot Your Work + A Better Option than Beating Yourself Up with Zak Rosen

0:00Sometimes a project gets stale and you're not feeling it anymore or it feels broken or like it never quite hit the mark in the way that you intended it to be a project. That is a necessary, super vital part of the creative journey that you have to work things out in real time. You try things and they don't work and they help you get insight on how to rethink it the next time you go out. On today's show, I have a chat with podcaster Zach Rosen. He's been on before. before he came on the last time he was bringing his show, The Best Advice Show, clips from that show. And now he's just gone through a rebrand of that show himself.

1:06It went from The Best Advice Show to a show called Weirdly Helpful. And it just seems like such a good pivot, such a good rebrand. It just seemed like such a good version of this that I wanted to take him onto the show, talk about it, to see if there was anything that you could take from it or that I could take from it because we all need to. There's always gonna be another moment to pivot or rebrand or whatever. That's just part of the process. And so this episode is designed to help you tap into that to figure out what you might need to pivot and how you might need to think of that. I hope something in this conversation does that for you.

1:46We also go through the process of what he does on his podcast and I ask him what is weirdly helpful to him in making his show and then he asks me that question and I share one I'm going to come back at the end with a synthesis of our two answers but filtered through the topic we're talking about this I'll be back at the end with a crawl call to adventure called what's wrong buddy and it's going to help you diagnose what in your creative practice might need a reboot. So stick around for that. Sounds fun. Sounds exciting to me. Hope you love this chat with Zach Rosen as much as I did. On the creative journey, it's easy to get lost, but don't worry, you'll lift off.

2:33Sometimes you just need a creative pep talk.

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4:41This is what's so great about Quince. Built to wear for a long time and still look good, plus they partner with factories that meet rigorous standards for craftsmanship and ethical production. Refresh your wardrobe with Quince. Go to quince.com slash pep talk for free shipping on your order and 365 day returns. now available in Canada too. That's Q-U-I-N-C-E.com slash pep talk. Free shipping and 365 day returns. Quince.com slash pep talk. So the first thing I want to talk to you about, Zach, was you're making this pretty big pivot in your show. You've been doing, how long were you doing the show before this move?

5:23For about five years. Yeah, okay. Over five years. And really consistently and tons of episodes. Yeah, yeah. And now you're making this big shift, rebranding it. It's the same feed. Could you talk a little bit about why you made that move? Because I feel like as a creative, there are lots of moments where you feel the urge to reinvent yourself. And it's hard to know whether it's the right thing. It's probably there's a lot of anxiety in it. But also excitement when you need refresh. So I don't know. I'd love to hear your thoughts about it. I feel like there became a moment and I think those happened years ago and I was just kind of ignoring it until recently there became a moment when people would ask me, what's your show?

6:08And I'd say, oh, it's called the best advice show. And when I said the best advice show, I didn't feel that proud of the name. like I was kind of just like rushing through the the title so I could like start telling them about like specific episodes because I was I was always proud of the stuff that I was making but the name I felt like it was really alienating to some people or could be some people would be like wait best what who who is this guy what is he talking about like not knowing that I'm being tongue-in-cheek or not knowing the kind of double meaning of it like what's your best advice which was my intention.

6:42And then the word advice, people are like, oh, no, no, no, no, no. I don't have advice. That's for smart people. That's for Tim Ferriss. You know, like I'm, I like, I like learning about other people's advice, but I couldn't possibly have anything worth sharing. And my whole project is about, no, no, no, no. We all have like this weird stuff that we do that I think counts as advice because it is helping us make it through our life in some way. And so I started paying more attention to, wait, if you don't like telling people the name of your show, maybe that's a problem. And because I hear you about the anxiety piece, like, is this the right thing?

7:23I didn't have much to lose. I don't make my living off this show. I make my living helping other people with podcasts. And I hosted a parenting show. And this has always just been my passion project. But a project that I've believed, long believed, like, wait, I think this could be something. Maybe I could make a little bit of money from this. And with not much to lose and this urge to be proud of the name of the thing, I started brainstorming. And I was like, wait, what is this actually about? And the episodes of The Best Advice Show that I love the most are when people come on and tell me something that I was just not expecting.

8:02Some weird thing like, oh, wait, really? You know, like just those. I want to be delighted. And I found that weirdly helpful is a more precise encapsulation of that impulse. And here we are. It makes sense. And the thing that is really interesting to me about that is people that listen to my show know that I never shut up about the idea of taste. And I get why that, you know, I just talk about too much. But I just think it's a concept that I've like tried to imbue with a specific meaning that's maybe not inherent in it where it's not just like what you like. It's also kind of like your taste buds creatively.

8:48It's like – As you told me years ago, get high on your own supply. Was that my episode? That was your episode, yes. So I'm still talking about this. Yeah. But, uh, I, that feeling of that's your kind of taste saying you're the word, the name of your show. Yeah. You're having this visceral taste reaction to it. And I think listening to that is kind of the creative secret is like, you have to know how to be aware enough to notice when you're having a recoiling moment or, or, and if you can make yourself feel something good with your work, that's like, that's the Holy grail. I think. Yes. Yeah. So yeah.

9:28And like when I'm telling people the name of the show now, like they smile, they're like, ah, like they, they get it more clearly than the best advice show, which is vague. And then, and so became some of the interviews that I was doing, they just became like, you know, what's your advice? Like anything for anyone. And it was just kind of way too big that the entryway. So my door is much smaller and it's like a weird looking little ramshackle door, but the people that are going to want to knock on it and come in, I'm hoping, you know, we'll be more excited to, to come eat. I really like that. And I think it's, it also feels like, uh, another kind of side of this is I think a lot about like coining phrases more and more as a creative prompt, as like a part of the process, whether it's a book that you're making or a podcast episode or whatever, a concept, whatever it is, for two reasons that's been on my mind a lot.

10:27One is I'm interested in pop philosophy. I don't really know what I'm talking about in that world, but I like consuming stuff from that realm. And one of the things that I think is really interesting about philosophers is that they go about imbuing new meaning in old words or coming up with words or coining little phrases. And I also really respect Cal Newport does this so well. He always, like, he's, I've just noticed like, oh, like there's something really powerful if you can come up with a two word thing that encapsulates a feeling that we have that we're not speaking to or something that we need to be able to work with.

11:08And I think even like my picture book, Invisible Things is a little bit like that. Like trying to, trying to give a concept, a face in a shape so that we can have a conversation about it. So I like weirdly helpful just feels like one of those where it's like, oh, you've done all. And you're also having to like realize all the baggage that people bring to words and how we have to get rid of words sometimes, all that kind of stuff. So I think it's, it's a really interesting creative problem to solve to name something. Thank you. It's been very, is the word innervating? is that the one that gives you energy i think um i can just say energizing with the what am i trying to do here it's been very energizing it's been uh really it feels like a new beginning or a rebirth of sorts and that was another reason why i was doing it i'd been making the show for five years still excited about it but also feeling a little bit of why um yeah why continue and this has given me new meaning and new reason to get to it.

12:11Yeah, I love that. Last thing that it brings to mind for me is this notion of writing on stage, like this idea of like working it out in real time by making stuff, by putting stuff out there, not waiting till you have the perfect name or the perfect everything. Creative Pep Talk as a name came from my blog back in the day. I had a blog called art directions, which was very similar to the content of the podcast. And I, at some point created a, like a feature that was like an interview series thing. And I called it creative pep talk. And when I came up with that, I thought, Ooh, that sounds even better than the name of this blog.

12:52Like I like that. And then that, but it came from doing stuff and putting stuff out and not just waiting until I had it all perfect. I think that's a good argument for that. No, I think that's, I mean, Creative Pep Talk, you know exactly what it is. And it feels more like you. Whereas art directions, or art direction. Yeah, art directions. It's like, it's too art, it's too like art school. It is. You know, like there's the art speak when like people are trying to like apply for a grant. And it's like, wait, what the, what are you saying? You can swear on this show, by the way, on my show. By the way, enervating is the opposite of energizing.

13:26Oh, damn. So it was, that's what the best advice show was. Best advice show is innervating. Really helpful is energizing to, to, to go back to that. But yeah, no, I think like, yeah. And best advice show sound and similarly, like art directions. It sounds like you're trying to like please someone else, some like unknown other person, but like creative pep talk, it's like pleasing to you. I completely, completely agree. I do think that was me being a little bit more in my professional illustrator mind, trying to impress the people and that kind of energy, which is never really great. By the way, by the way, sorry.

14:07I have someone or like a group of people in mind when I'm thinking about like those people who I'm trying to impress, which is like that I don't need to be thinking about them. Yeah. Yeah. Do you have those people? I do and I think that I at some point I always say that the the breaking point of that for me was adopting the name Andy J pizza because I really felt like it kind of happened on accident because I just made my website andyj.pizza so and then people thought that was my name yeah and then I just thought I thought it was your name for whatever at least the first year of knowing you Let's go.

14:40Let's just do it. But I think that move really felt like, oh, almost everyone I really admire and respect in this industry is probably going to think that's stupid as hell. And because, you know, I think that was partially going to school and really appreciating some of the cerebral, I don't know, top of the industry illustrators that are just serious artists. and I think, and I wasn't even at the time making picture books either. So it wasn't like, there's a whole bunch of reasons why it wasn't as obvious as it feels now. But I think after that moment, and then after, and then the starting of the podcast was a big one too.

15:24Cause I thought, I know I'm going to talk a lot about like business and marketing and all this stuff that I just feel like is going to negate my ability to play it cool in the industry ever again. And so I do think like killing that, those voices in my head were, was helpful, even though it's still always an issue, but I think it's helped. Yeah. Yeah. You have that too. Yeah. Um, and I've learned, I think as I've gotten older, I, I, those voices have, uh, calmed down, um, or have, have become less prominent in my head because, you know, like I'm not doing the same thing that they're doing. I thought I was like competing with these like auteurs or something, but first of all, I'm never going to be like them and I can, I can just be me.

16:16Yeah, I get that. I think in my, now that I'm in the picture book world, I struggle a little bit more. I had, I was talking to a picture book, um, author illustrator that I really respect earlier this year. And I, he kind of caught me being like, yeah, I want to do this, but I don't know what the industry is going to think of that. And he's like, dude, F the industry. What are you talking about. Like, this is your career, like do your thing. Um, and so I, yeah, I probably still have a little bit of that now that I'm in this new arena, but, uh, yeah, it's something you always have to refresh yourself with.

16:49So let, okay. We wanted to do your podcast concept, your premise, uh, here. And now we're going to talk about something that's weirdly helpful to you as a creative person making stuff. Um, and then we'll potentially go over to one of my weirdly helpful things, but let's start with you. And you, you know how to do this better than, than me. Cause this is your premise, but is that how, how it rolls? Yeah. Yeah. Um, I mean, I'm, I'm in the safe position as the host of the show of getting to just hear other people's and quietly judge theirs. And it's rare that I have to give my own weirdly helpful.

17:24So it's actually a little vulnerable. And I had to think about this. That's good. Yeah, no, it's, it's, I think it's a very helpful exercise to be on the side of it. So my weirdly helpful morsel is around interviewing, which is something I've been doing for my whole career, which now spans about 20 years. I've basically been doing this since I was a junior in college, and that was 20 years ago. And it's around asking questions and thinking about questions as a kind of minimalist like i so often i'm listening i listen to a lot of talk shows chat shows interview shows more so now than narrative shows and so frequently the host is asking four questions in one yeah uh or very true very true or asking a question and then rationalizing to the guest why they're asking it so andy here's an example like so andy i want to ask you like what was it like moving around all the time as a kid because like it seems like and then they go off so you have to put the goddamn period after kid yeah and don't say because because whatever your theory is about that it might be interesting, but all you're doing is taking up space that you're getting, you want your guests to walk into.

18:53Do you know what I mean? I mean, this is a thing I've thought about tons and I've gotten better over time to be like, okay, I know the kind of arena where I want to go. What is the simplest way to ask a question that gets that open? And then, then I will often, often instead of adding tacking on all that extra stuff yeah i will put a note of this could be a follow-up comment if it feels like it's going to push the conversation into an interesting place that's in your prep yeah okay that's really smart yeah yeah and i should say like i am totally guilty of asking oh these these big questions all the time and so i'm and i'm often cutting them in post i'm when i'm when i'm cutting the interview i'm like okay let me ditch the second two-thirds of that bit so we can just get straight to your guest yeah and it's a really simple thing but i find it also people also do it in real life and i shouldn't treat real life like i shouldn't i shouldn't judge people for their question asking skills in real life but i do you can't help it i can't help i think about the same thing yeah and i'm often in my head just like okay stop period that's a good question so why did you keep going and and i think all of us actually someone gave me this advice on the show my friend autumn brown whose whose podcast i i edit she that she hosts with her sister adrian it's called how to survive the end of the world and autumn learned this thing i think it's in like the facilitation world when you're you know in dialogue with a group of people and you're reflecting on something or asking a questions you do this thing called wait that you ask yourself itself it's an acronym wait why am i talking you know and often as hosts we're taking up space because i don't know we're nervous to have one of our heroes on like there's good good reasons to be to be mumbling um more but we don't need to be and when we ask ourselves that question wait why am i talking i think our questions become a lot more precise a lot more austere and generous.

20:58You know what I mean? Yeah, I definitely know what you mean. Because I've thought about prepping for an interview in a similar way to writing anything. So in the person you're talking to, it's not completely unlike when you go to write something, you're interacting with a specific part of yourself. So you're asking a part of yourself something. So you're creating this dynamic. And so going into it, I try to strike a balance between plotting and pantsing. So I'm like, I have a plan, but I don't want to ruin the organic nature of the conversation by forcing this way. But having the plan helps. It helps me feel prepared.

21:42It does all kinds of things. I wonder if you, when it comes to writing an elegant question, what things have you learned that are weirdly helpful in doing that? Well, there's a great producer, reporter, host, Alique Spiegel, who used to, she created Invisibilia. She was a producer on This American Life for a long time. I think she might be back at This American Life right now. She does this great interview on Transom, which is how I learned mostly how to make radio, transom.org. They have a podcast called Sound School, hosted by Rob Rosenthal. You should go and listen to her episode because she's such a master at this.

22:26But she says this thing. She says, make your mind like water when you're plotting out an interview. And so what she means by that, I think it's like she's trying to actually imagine herself in this conversation that she's going to have like the next day or whatever. And imagine the different directions that it can go. And then thinking about, okay, so if it goes this way, like if this question provokes like this really emotional response, then I could go here. That's interesting. Like a flow chart. Kind of a flow chart. But then like you were saying, like, don't be married to it. So make it kind of anticipate where it can go, because that's going to kind of train your brain into, OK, it can go this way, it can go this way, but I'm going to flow.

23:09Like I'm going to flow with wherever it goes. But at least like I will have like the proper gear, you know, to navigate if and when it does go to this place. And it is this contradiction. Like, you know, we go into these interviews sometimes with like these 15 questions we want to ask. And I'm sure you've had the experience where you ask one and then you're off and running and then the other 14 don't get asked. And that's OK. But at least as long as you're kind of spending time in the world of like, what might this be? What might this feel like? I think that can be pretty helpful. When you're doing these, do you have an end goal in mind?

23:43I know we're talking about kind of being loose with it. Yeah. But yeah, do you have an end goal in mind with each guest? Like, oh, I kind of know where I want it to go? Yeah. I mean, with weirdly helpful specifically, it's actually easier than like your show or other shows because I am going for the weirdly helpful thing and just building up to it and helping people realize what theirs is for themselves. Sometimes people don't have it all worked out. Usually they don't before coming on. So I'm just trying to hold their hand and get to this thing and celebrate this weirdly helpful thing that they do, which is different than like interviewing someone for, you know, like a biographical interview or interviewing them about a specific piece of work.

24:26Sure. Do you know what I mean? But I am trying, I am, but the way, because my show is very self-helpy, I am trying to find like a takeaway. So there is a similarity to that. Yes, definitely. It's not just a journey. The other thing that comes to mind, though, that I want to know what tricks you found for helping someone unearth these things that they know because. Yeah. No, I'll do that as a follow-up. Look at you. You caught yourself. Look at you. I did. I'm learning. It's so fun trying to help people unearth it because, yeah, how do I get there with them? I'm really interested in, you know, in Seinfeld, Elaine is like, I think it might be the Bizarro episode where she's like, I can't come into this apartment and talk about the excruciating minutiae of everyday life.

25:24Like she's feeling disillusioned with Jerry and George and Kramer. And that's why she's spending more time with Bizarro Jerry, because they're more bookish and interesting and extroverted. But I really love the excruciating minutia of everyday life being like, what are you how are you getting from getting your kids out the door and to like sitting down at your desk? like what are you standing up and like staring at your phone while you eat lunch or are you you know sitting down at the table and like what is that like so the tricks I think are like take me to this part of your day when you're doing this weirdly helpful thing and just tell me like what does it look like um because all these weirdly helpful things I'm I'm realizing are just like these things that we're doing like in between the big things in between the meetings and the birthdays but like just these like in between things when lauren is going into the shower and feeling a little bit like another day it's a big day i need to cheer myself up so she's she lathers a bunch of soap on her belly and uh and draws and draws in it uh and just draws a often a piece of pizza actually um but just yeah just some she calls it her daily shower belly and And it's just like this thing that reminds her like, oh, I'm I'm a fucking idiot kid looking out for joy and delight.

26:44So so that's pretty cool. She came on the show not realizing, I think, what her thing was or why she was doing it. And I and together we realize, oh, it's like you are tapping into this kind of banal joy and what a gift that is to give to yourself. And so I think it's like, just take me into your day. It's very intimate, you know, like take me into like this quiet part of your day. Um, it's not a trick, I guess. It's just more like being really interested in this thing that people are doing without much thought, but realizing, oh yeah, I guess this weird little ritual is a thing. It's a weirdly helpful thing.

27:20That's, that's really good. And I think it gets at why I asked that question. I feel like these things are examples of stories that we have to tell. So I'm really interested in how a story you have to tell often it's a transformation of a character. It's a transformation that you had. And so when I try to come up with stories or episodes of the show, or if I'm working with someone who I'm trying to help them come up with a story, I'm always looking for different ways in to what do you know? You know, the writing, what you know, this is what I think it's kind of about is like, well, what do you know from experience?

28:04And it's hard to name because they become anything that you really know you into or in live, you integrate it on a subconscious level. Yeah. You know? So I, I, I like your, your trick. I think it's a good one. I like what do you, so you ask explicitly, like, what do you know? I, I, there's a few different things I'll use, but one of my favorites, wasn't outlined as like a story technique, but it's by a guy you might've heard of him because you're in podcasting. His name's Eric Newsom. You know, this guy, I thought his book make noise was really great. It's back here somewhere. Boom. I thought it was really insightful for all kinds of reasons.

28:45But one of my favorite things that I pulled from it ended up being a story thing. He says in his back pocket, he always has a question that usually leads somewhere interesting. And it's, if you're in, if you're interviewing an illustrator, you say, what do illustrators get wrong about illustration? Or what have podcasters get wrong about podcasting, whatever. And I love that because it really gets at something that you probably learn from experience and something that you feel passionate about. And it really is, it has the makings of an arc of a act one, act three of like, you think it's this way and then you end up thinking it's this way.

29:25Totally. That is a great question. Yeah. That's one I think about a lot. Do you ask that a lot in your interviews? I do. Uh, I do. Yeah. I would say I throw it in there when I feel like I don't, it's, it's rarely that I feel like, Oh, I don't know where to go, but more like this person has, if I feel like they're able, the kind of person that can articulate their point of view, that's a really good question. Yeah. Not everybody, some artists that you interview, you have to approach it in a totally different way because they, a big part of why they do what they do is that they don't verbalize what they do.

30:00So yeah, that's a totally different kind of interview. Yeah. Yeah. Yeah. So, all right. Well, I love that. I think, do you have any last bits to add on that? Sometimes it's so pretentious, but I think of questions as bonsai trees. Okay. Yeah. I love that. I, it's not, I'm, I'm here for the artistry. This is, let's get the pretentiousness out there. I, I, that's one of my big beefs actually, is that artists because of, you know, so many things, but probably a big partial part of it is the way the internet makes fun of things. Yeah. We can't get arty about talking about stuff. Like I, like that's my favorite way to think about and talk about stuff, but I love that.