Love Michael’s work. I found the part about dialogue super interesting. It seems he’s blessed with some funny people in his life, as well. There are times when his wife or sister will rattle off a great punchline and then his job is to capture that.
Question for Michael: I’m curious how you organize your writing life. If i understand correctly, writing Situation Normal isn’t your full-time deal. How/where/why/when do you find the time to write your stories?
Thanks Lyle! You're right, I am blessed with funny people in my life. In fact, there have been times when I've thought about starting a social media account just to share my wife's random quotes.
To answer your question about organizing my writing life, let me start with a little context. I make my living as a freelance writer, mostly in the ad tech space. That kind of work pays well, but there are some ups and downs (more on that in a moment). It's also important to understand that Christina usually has a full-time W2-type job with salary and benefits, although at the moment she is between jobs, which makes life interesting. Anyway, I mention that because I think it's important to understand that I'm not alone in this, and if I was alone in this, my work, both in terms of output and the stories I tell, would look very different.
OK, so now for the actual organization stuff. Remember those ups and downs I mentioned? I tend to have somewhat intense weeks, followed by down weeks. It's just the nature of freelance comms work. But on the bright side, that work usually means one meeting at a set time, followed by hours of work that I can do at any time. That flexibility really helps a lot. But the real trick, and it's really not a trick at all, is to make the most of the down times because I do have days when there is zero work, and I don't want to waste those. I maximize those days in a few ways, but most of what I'm doing is falling back on the skills I learned when I was on staff at various pubs earlier in my career.
First, I make an editorial calendar. It's nothing fancy. Actually, it's just color-coded items on my actual calendar. That really helps me plan, obviously. But it also helps me see the big picture. Here's what I mean by that. If I have one big piece a month, I feel like I'm really earning my subscribers. Or, put another way, that one big piece is going to be the reason readers find me and stay with me. But those pieces take more time to pull off than a typical story. For example, the piece about going to the porn convention took a few days to report and I wrote it over the course of several weeks. But looking at my editorial calendar in January, I could easily see that the porn piece was going to be my big piece for that month, which allowed me to schedule other big (difficult to execute) ideas for future months.
Second, I bank stories. If you don't use an editorial calendar it's always going to feel a little hand-to-mouth. But if you do use a calendar, you can bank stories and use that story well to plug gaps in your schedule. It helps to have evergreen stories that can fit into any gap. BTW, you've got some evergreen stories, my friend!
Third, I write best in short bursts. I learned do this as a reporter because, well, I had deadlines, and sometimes those deadlines were measured in minutes and hours. I don't recommend that approach, but if you've built that muscle, you might as well use it. Anyway, what I've found is that I can get a lot out of a sprint, and so I make sure that I'm sprinting everyday, and when possible, multiple times a day. The challenge, for me anyway, is that it's one thing to sprint to a news deadline, and it's something else to link together countless sprints for a long-form piece, or a novel. It took a long time to get comfortable with making incremental progress like that, but after pulling off a few bigger projects that way, I guess I'm a believer in the sprint life.
Wow, what a generous and insightful answer! I’m not nearly as organized as you are about my writing. But I should definitely be more organized than I currently am. I do know what you mean about bigger pieces. I’ve had some of those, as well, and it usually means they took me a bit longer to get done, so that makes sense.
That's a tough question for me. I've always been good at creating and (usually) hitting self-imposed deadlines, but that's probably anxiety and fear and self-loathing -- a potent cocktail i do not recommend.
That said, here's a trick. I tell myself that I only need to sprint for 10 minutes. It's a lie, but lies can be really useful, if you deploy them strategically and remember not to believe them in an internalized way that becomes a greater truth. Anyway, this particular lie is all about getting you to the sprint, not getting you through the sprint. Basically, you're saying to yourself, "look, dude, this writing session isn't going to happen, but that's ok, because you just need to phone it in, you know, check the box." the box you're checking is the minimum viable writing (MVW) you need to do that day to have something tangible you can point to that proves to you (or anyone who might be asking) that you did, in fact, write that day. In basketball, there's a word for this: layup. Can you hit the deadline? Maybe, maybe not. Can you write a brilliant piece? Maybe, maybe not. But can you show up for ten minutes and just type something? I think so. That's the layup. It's a way of saying, I don't got this, so I'm just gonna do the thing I know I can do.
Now, sometimes you do the ten minutes, and honestly, the words you put on the page suck butt, and every one of those ten minutes was agony. in that scenario, step away from your desk, hydrate, and touch grass, as they say. Also, pat yourself on the back because you did it. you showed those demons that don't want you to get anything done who's boss. Seriously, pat yourself on the back here.
But other times, most times, actually, you blow past the ten minutes without even realizing it. The reason? Your hang up about starting was actually a hang up about finishing, or writing the best piece in the history of pieces, or some other bullshit that isn't really going to help you. in that scenario, you keep writing as long as you can. then you step away from your desk, hydrate, and touch grass, as they say. Also, pat yourself on the back because you did it. you showed those demons that don't want you to get anything done who's boss. Seriously, pat yourself on the back here.
I'm adding my belated thanks for this question (thank you, Lyle) and for this answer (thank you, Michael) and to Alex for doing this interview. I saved it from the other day because I knew I wanted to give it my full attention and that was not possible when it was first published.
I love the whole idea of the sprints and how you "fool" yourself into it. I do a version of this. After writing my novel in the morning (a piece of writing that few have asked for and they are mostly my nonpaying friends and relatives) I try to spend an hour or two on my newsletter earlier. Sometimes this means just salting away random thoughts, paragraphs, and links for me to assemble on Fridays. Other times, I have a whole piece well before the deadline. Like you, I have a kind of publishing calendar. Actually, what I have is a folder on google docs where I have titles and ideas in individual docs and then, each week, I take a look at those and the upcoming calendar to see what works best given the time of year and my life at the moment.
Still, there have been weeks when I get a new idea out of the blue on Thursday and end up writing a completely unplanned newsletter on Friday. Does that ever happen to you?
This often happens to me! I have a piece written and it’s scheduled to post for Sunday, but then something interesting happens and I know it’ll make a good story, but it’s timely, so I know that it’s one of those things where I either write it or lose it forever. Usually, I write it, unless there just isn’t time. But then I bump the scheduled piece. Thankfully, if it can be bumped, it’s probably evergreen, so this adds to the story well. A good example of a piece I wrote very late in the week is the one about getting trolled by my mom. It happened after I already had another piece set to go, but I felt like there was a timeliness there that forced me to either use it or lose it. As for the piece I bumped, it remains in the well and there’s no telling when I’ll publish it. But it’s ready to go when I need it.
-- bring Wilder into your world as much as you can
-- you can say something unexpected, something vulnerable, something a little absurd, and then because humans usually want to get along with other humans, they’ll mirror your response, and then you’re off to the races.
🙌🙌 Just wow, both of you. WOW. I mean, B.A.T. and Situation Normal are among my favourite reads already, but BOTH on the same plate? At the same time? WITH a Florida mortgage bagel AND peanut butter? Almost too MUCH wow! 🤩🏆🥳
Alex, I love that you've become friends with Michael! I love both of your newsletters! How did you hear about this writer's conference in L.A.? I am also an Angeleno! I'm actually going all the way out to NYC this week for a New Yorker staff party and I am TERRIFIED. I am but a wee cartoonist who's never met any of the other cartoonists. Your story of introducing yourself to Michael and even interviewing him is very inspirational to me. I'm going to try to be as brave as you! Fingers crossed.
ahhhh omg i would be so fuckin terrified at a party like that, i'd eat so many of the finger foods like way too many and then need to go home early cuz i felt sick.
So in LA it wasn't a conference as much as just like a...hang! I know people wanna do another one soon though so I'll def let you know! there's a bunch of us out here!
i also am fingers crossed for you please report back and let us know how it goes
I have never met Liza, but I love her work and follow her Substack (and possibly all her social media). Just read your interview btw: a damn pleasure, great work! I very much hope I get a chance to meet her this week.
I will absolutely report back! If anything, you're making me realize I should probably make a Substack post about it. I'm still pushing through some imposter syndrome, so I have to remind myself that these experiences are fun to write and read about!
Alex, I would LOVE to be invited to the next L.A. writers hang. Oh my goodness. I would be overjoyed. Thank you for writing such kind replies, I really appreciate it.
Late reply but I am reporting back on the party! I met Liza!!! She was soooo nice! I seriously b-lined to her the second I saw her, haha. I also wrote about the whole experience and was honestly inspired to write about it based on you telling me to "report back", because I foolishly hadn't even considered writing about it before, which is kind of insane. Thank you for your support, Alex. It really helped.
truly tho - the early internet was a place I long for and miss dearly. I'm tryna write about it, hopefully will have something to share w the world soon.
I'm a big fan of the CPEU, which is why I'll be dedicating my life to making YouTube videos documenting all the hidden easter eggs in each of your newsletters that hint at bigger crossover events to come – and I'll be leaving toxic, hateful comments for anyone who even lightly disagrees with my assumptions!
RAH! I loved learning more about Mr. Estrin's life and his processes. Esp., Alex, that you asked how he remembers the entirely of the conversation. I asked him this a long time ago and he got all cagey on me so this was extremely satisfying.
ALSO
-Was the plain bagel with peanut butter TOASTED? They are so much better toasted and if you’re going the PB route you’re already flouting tradition anyhow.
-Did Mr. Estrin accidentally eat any mortgages while visiting Florida and dining at his sister in law's breakfast table that doubles as a desk for her mortgage processing job?
-Yes that photo of Mr. Estrin and his dad is truly incredible.
-“One thing journalism taught me was how to ask open-ended questions and then shut the fuck up.” YES
Anne he was cagey with me too for like A WHILE. Like over a year, he wouldnt answer. Finally I just went to his house and camped out in the bushes and when he came out in the morning wearing a robe drinking his coffee to get his morning paper, I sprung out and still he wouldn’t tell me so I decided to be a sneak and engaged him in a long long convo about all sorts of details I knew he’d be incapable of forgetting: my thoughts on the mayor, taxes, pigs with three feet (they are lucky in Chile), and my thoughts on inflation (it’s got something to do with all those balloons they keep shooting down). then when his mind was full of little details he’d need to remember, i asked him. and he told me, and I screamed ‘that’s how you journalism’ so loud that three different police precincts were called. i was arrested but let out immediately because michael got into long great convos with all three of the officers and by the end we were all friends and went to Chili’s for a burger and a beer.
We’ve trademarked it, and we’re in talks to license it to The LA Times because while they do struggle to journalism sometimes, they really need a tagline.
Sorry if I was cagey. I must've been drinking from my Nicolas Cage coffee mug.
Yes, the bagel was toasted. In this particular part of Florida there aren't any bagel places putting out fresh bagels, so you get supermarket bagels, and you gotta toast those, unless you're a freak of nature, which I'm not.
I didn't any mortgages in Florida. Caroline's desk is next to the dining room table, so there's very little risk of mixing up food and mortgages. Also, almost every document she touches is digital, which is good because if mortgages are edible, my three nephews would probably eat all of the mortgages along with all of the chicken fingers. They're growing boys, but for real, those dudes can eat.
I'm glad you like the photo of me, my dad, and my sister. I'm really glad Alex made me find it. And the timing of his request was perfect because my sister and I always feel a little sad around Super Bowl Sunday because that was a show our dad did for two decades and we both have really good memories of working with him.
Love Michael’s work. I found the part about dialogue super interesting. It seems he’s blessed with some funny people in his life, as well. There are times when his wife or sister will rattle off a great punchline and then his job is to capture that.
Question for Michael: I’m curious how you organize your writing life. If i understand correctly, writing Situation Normal isn’t your full-time deal. How/where/why/when do you find the time to write your stories?
Thanks Lyle! You're right, I am blessed with funny people in my life. In fact, there have been times when I've thought about starting a social media account just to share my wife's random quotes.
To answer your question about organizing my writing life, let me start with a little context. I make my living as a freelance writer, mostly in the ad tech space. That kind of work pays well, but there are some ups and downs (more on that in a moment). It's also important to understand that Christina usually has a full-time W2-type job with salary and benefits, although at the moment she is between jobs, which makes life interesting. Anyway, I mention that because I think it's important to understand that I'm not alone in this, and if I was alone in this, my work, both in terms of output and the stories I tell, would look very different.
OK, so now for the actual organization stuff. Remember those ups and downs I mentioned? I tend to have somewhat intense weeks, followed by down weeks. It's just the nature of freelance comms work. But on the bright side, that work usually means one meeting at a set time, followed by hours of work that I can do at any time. That flexibility really helps a lot. But the real trick, and it's really not a trick at all, is to make the most of the down times because I do have days when there is zero work, and I don't want to waste those. I maximize those days in a few ways, but most of what I'm doing is falling back on the skills I learned when I was on staff at various pubs earlier in my career.
First, I make an editorial calendar. It's nothing fancy. Actually, it's just color-coded items on my actual calendar. That really helps me plan, obviously. But it also helps me see the big picture. Here's what I mean by that. If I have one big piece a month, I feel like I'm really earning my subscribers. Or, put another way, that one big piece is going to be the reason readers find me and stay with me. But those pieces take more time to pull off than a typical story. For example, the piece about going to the porn convention took a few days to report and I wrote it over the course of several weeks. But looking at my editorial calendar in January, I could easily see that the porn piece was going to be my big piece for that month, which allowed me to schedule other big (difficult to execute) ideas for future months.
Second, I bank stories. If you don't use an editorial calendar it's always going to feel a little hand-to-mouth. But if you do use a calendar, you can bank stories and use that story well to plug gaps in your schedule. It helps to have evergreen stories that can fit into any gap. BTW, you've got some evergreen stories, my friend!
Third, I write best in short bursts. I learned do this as a reporter because, well, I had deadlines, and sometimes those deadlines were measured in minutes and hours. I don't recommend that approach, but if you've built that muscle, you might as well use it. Anyway, what I've found is that I can get a lot out of a sprint, and so I make sure that I'm sprinting everyday, and when possible, multiple times a day. The challenge, for me anyway, is that it's one thing to sprint to a news deadline, and it's something else to link together countless sprints for a long-form piece, or a novel. It took a long time to get comfortable with making incremental progress like that, but after pulling off a few bigger projects that way, I guess I'm a believer in the sprint life.
Hope that helps! It's a great question, btw!
Wow, what a generous and insightful answer! I’m not nearly as organized as you are about my writing. But I should definitely be more organized than I currently am. I do know what you mean about bigger pieces. I’ve had some of those, as well, and it usually means they took me a bit longer to get done, so that makes sense.
Don’t let my answer fool you. I’m completely disorganized in other aspects of my life.
Michael that answer was amazing. follow up question: how do you motivate yourself for the sprints when the thing you're writing isn't due in an hour?
That's a tough question for me. I've always been good at creating and (usually) hitting self-imposed deadlines, but that's probably anxiety and fear and self-loathing -- a potent cocktail i do not recommend.
That said, here's a trick. I tell myself that I only need to sprint for 10 minutes. It's a lie, but lies can be really useful, if you deploy them strategically and remember not to believe them in an internalized way that becomes a greater truth. Anyway, this particular lie is all about getting you to the sprint, not getting you through the sprint. Basically, you're saying to yourself, "look, dude, this writing session isn't going to happen, but that's ok, because you just need to phone it in, you know, check the box." the box you're checking is the minimum viable writing (MVW) you need to do that day to have something tangible you can point to that proves to you (or anyone who might be asking) that you did, in fact, write that day. In basketball, there's a word for this: layup. Can you hit the deadline? Maybe, maybe not. Can you write a brilliant piece? Maybe, maybe not. But can you show up for ten minutes and just type something? I think so. That's the layup. It's a way of saying, I don't got this, so I'm just gonna do the thing I know I can do.
Now, sometimes you do the ten minutes, and honestly, the words you put on the page suck butt, and every one of those ten minutes was agony. in that scenario, step away from your desk, hydrate, and touch grass, as they say. Also, pat yourself on the back because you did it. you showed those demons that don't want you to get anything done who's boss. Seriously, pat yourself on the back here.
But other times, most times, actually, you blow past the ten minutes without even realizing it. The reason? Your hang up about starting was actually a hang up about finishing, or writing the best piece in the history of pieces, or some other bullshit that isn't really going to help you. in that scenario, you keep writing as long as you can. then you step away from your desk, hydrate, and touch grass, as they say. Also, pat yourself on the back because you did it. you showed those demons that don't want you to get anything done who's boss. Seriously, pat yourself on the back here.
this is great. i'm gonna see if i can get christopher walken to do a live reading of it
I'm adding my belated thanks for this question (thank you, Lyle) and for this answer (thank you, Michael) and to Alex for doing this interview. I saved it from the other day because I knew I wanted to give it my full attention and that was not possible when it was first published.
I love the whole idea of the sprints and how you "fool" yourself into it. I do a version of this. After writing my novel in the morning (a piece of writing that few have asked for and they are mostly my nonpaying friends and relatives) I try to spend an hour or two on my newsletter earlier. Sometimes this means just salting away random thoughts, paragraphs, and links for me to assemble on Fridays. Other times, I have a whole piece well before the deadline. Like you, I have a kind of publishing calendar. Actually, what I have is a folder on google docs where I have titles and ideas in individual docs and then, each week, I take a look at those and the upcoming calendar to see what works best given the time of year and my life at the moment.
Still, there have been weeks when I get a new idea out of the blue on Thursday and end up writing a completely unplanned newsletter on Friday. Does that ever happen to you?
This often happens to me! I have a piece written and it’s scheduled to post for Sunday, but then something interesting happens and I know it’ll make a good story, but it’s timely, so I know that it’s one of those things where I either write it or lose it forever. Usually, I write it, unless there just isn’t time. But then I bump the scheduled piece. Thankfully, if it can be bumped, it’s probably evergreen, so this adds to the story well. A good example of a piece I wrote very late in the week is the one about getting trolled by my mom. It happened after I already had another piece set to go, but I felt like there was a timeliness there that forced me to either use it or lose it. As for the piece I bumped, it remains in the well and there’s no telling when I’ll publish it. But it’s ready to go when I need it.
Great question!
dear alex,
i love you and i love this.
things i specifically love about this:
-- peanut butter
-- you are your only real competition
-- bring Wilder into your world as much as you can
-- you can say something unexpected, something vulnerable, something a little absurd, and then because humans usually want to get along with other humans, they’ll mirror your response, and then you’re off to the races.
thank you again, both of you!
love,
myq
NO THANK YOU MYQ ilu more and more by the day and not to mention the minute
🙌🙌 Just wow, both of you. WOW. I mean, B.A.T. and Situation Normal are among my favourite reads already, but BOTH on the same plate? At the same time? WITH a Florida mortgage bagel AND peanut butter? Almost too MUCH wow! 🤩🏆🥳
dawwww thank you Rebecca!
Love, love, loved, and went right over and subscribed.
woohoo
Awesome! Thank you, Mary!
I love reading the two of your separately, but together: pure comedic genius!
the crossover episode that people didnt know they needed! Thanks so much Jillian :)
Alex, I love that you've become friends with Michael! I love both of your newsletters! How did you hear about this writer's conference in L.A.? I am also an Angeleno! I'm actually going all the way out to NYC this week for a New Yorker staff party and I am TERRIFIED. I am but a wee cartoonist who's never met any of the other cartoonists. Your story of introducing yourself to Michael and even interviewing him is very inspirational to me. I'm going to try to be as brave as you! Fingers crossed.
ahhhh omg i would be so fuckin terrified at a party like that, i'd eat so many of the finger foods like way too many and then need to go home early cuz i felt sick.
do you know Liza Donnelly? I actually did an interview w her last year she's great! https://botharetrue.substack.com/p/comedy-through-cartoons-an-interview
So in LA it wasn't a conference as much as just like a...hang! I know people wanna do another one soon though so I'll def let you know! there's a bunch of us out here!
i also am fingers crossed for you please report back and let us know how it goes
I have never met Liza, but I love her work and follow her Substack (and possibly all her social media). Just read your interview btw: a damn pleasure, great work! I very much hope I get a chance to meet her this week.
I will absolutely report back! If anything, you're making me realize I should probably make a Substack post about it. I'm still pushing through some imposter syndrome, so I have to remind myself that these experiences are fun to write and read about!
Alex, I would LOVE to be invited to the next L.A. writers hang. Oh my goodness. I would be overjoyed. Thank you for writing such kind replies, I really appreciate it.
amazing!!
Late reply but I am reporting back on the party! I met Liza!!! She was soooo nice! I seriously b-lined to her the second I saw her, haha. I also wrote about the whole experience and was honestly inspired to write about it based on you telling me to "report back", because I foolishly hadn't even considered writing about it before, which is kind of insane. Thank you for your support, Alex. It really helped.
https://esjule.substack.com/p/i-went-to-a-new-yorker-party
omg!! that is so dope and great I'm excited to read this !
I forgot to mention how happy that last sparkly lady GIF made me. Damn the early internet was a wondrous place.
then get ready to have your mind blown - https://gifcities.org/
truly tho - the early internet was a place I long for and miss dearly. I'm tryna write about it, hopefully will have something to share w the world soon.
the power these gifs hold over me...
i vERY much look forward to your nostalgic internet post.
I was honestly drawn to Substack because I missed LiveJournal and early internet blogging in general.
we are returning to the weird internet
I'm a big fan of the CPEU, which is why I'll be dedicating my life to making YouTube videos documenting all the hidden easter eggs in each of your newsletters that hint at bigger crossover events to come – and I'll be leaving toxic, hateful comments for anyone who even lightly disagrees with my assumptions!
(Seriously, though, love you both!)
hahahaahaha this made me big LOL
We won’t rest until we’ve put out enough material to validate your excellent life choice to become the most prominent toxic creator covering the CPEU.
Seriously, thank you, Geoffrey!
RAH! I loved learning more about Mr. Estrin's life and his processes. Esp., Alex, that you asked how he remembers the entirely of the conversation. I asked him this a long time ago and he got all cagey on me so this was extremely satisfying.
ALSO
-Was the plain bagel with peanut butter TOASTED? They are so much better toasted and if you’re going the PB route you’re already flouting tradition anyhow.
-Did Mr. Estrin accidentally eat any mortgages while visiting Florida and dining at his sister in law's breakfast table that doubles as a desk for her mortgage processing job?
-Yes that photo of Mr. Estrin and his dad is truly incredible.
-“One thing journalism taught me was how to ask open-ended questions and then shut the fuck up.” YES
-Awesome GIFS!!!
Anne he was cagey with me too for like A WHILE. Like over a year, he wouldnt answer. Finally I just went to his house and camped out in the bushes and when he came out in the morning wearing a robe drinking his coffee to get his morning paper, I sprung out and still he wouldn’t tell me so I decided to be a sneak and engaged him in a long long convo about all sorts of details I knew he’d be incapable of forgetting: my thoughts on the mayor, taxes, pigs with three feet (they are lucky in Chile), and my thoughts on inflation (it’s got something to do with all those balloons they keep shooting down). then when his mind was full of little details he’d need to remember, i asked him. and he told me, and I screamed ‘that’s how you journalism’ so loud that three different police precincts were called. i was arrested but let out immediately because michael got into long great convos with all three of the officers and by the end we were all friends and went to Chili’s for a burger and a beer.
THAT'S HOW YOU JOURNALISM is my new favorite line for everything.
We’ve trademarked it, and we’re in talks to license it to The LA Times because while they do struggle to journalism sometimes, they really need a tagline.
This is all true. 💯
Sorry if I was cagey. I must've been drinking from my Nicolas Cage coffee mug.
Yes, the bagel was toasted. In this particular part of Florida there aren't any bagel places putting out fresh bagels, so you get supermarket bagels, and you gotta toast those, unless you're a freak of nature, which I'm not.
I didn't any mortgages in Florida. Caroline's desk is next to the dining room table, so there's very little risk of mixing up food and mortgages. Also, almost every document she touches is digital, which is good because if mortgages are edible, my three nephews would probably eat all of the mortgages along with all of the chicken fingers. They're growing boys, but for real, those dudes can eat.
I'm glad you like the photo of me, my dad, and my sister. I'm really glad Alex made me find it. And the timing of his request was perfect because my sister and I always feel a little sad around Super Bowl Sunday because that was a show our dad did for two decades and we both have really good memories of working with him.
aw man I'm glad that photo helped bring back some good memories. He truly seems like the best dude and dad and everything else too
Great interview. Very interesting! We both published pieces about porn on the same day!
its true everyone also go read Kevin's piece its really good: https://kevinjamesdoyle.substack.com/p/my-favourite-porn
Kevin’s piece was really strong! You’re right, Alex, everyone should go read it.
awesome interview alex! michael's newsletter is absolutely hilarious 😬
Thanks Peter, yea Michael is a legend
Thank you, Peter!