Reflections on Stuck on the Staircase

Years ago, a friend of mine told me about Type 2 Fun. Type 2 fun is the less-obvious kind of fun. While you’re doing it, it might even be actively not-fun. It’s the final six miles of the marathon where your sister is cheering you on every step of the way, which you think of fondly later, but sort of hated her for a little bit at the time. It’s the time you and your best friend got stuck canoeing in the pouring rain, so cold and miserable and punchy that finally you just burst out into song. It’s the stuff of great memories, those moments when you have to face something hard, but end up feeling grateful afterward. 

I loved this concept of Type 2 fun so much that I did an episode about it in season 1. I mention it now, because when I think about Stuck on the Staircase, I think about Type 2 fun. 

Now, after the fact, it’s one of my favorite episodes. I actively enjoyed the experience of listening to it again in preparation for this module. It comforted me, made me laugh, and generally just made me feel glad for the experience of getting to learn so much as I was creating it.

But at the time I was working on the script for that episode, I wasn’t having much fun at all. I was stuck in a project management puzzle I didn’t know how to solve, one that I hadn’t even seen coming because I’d been so sure that I’d gotten myself so organized and prepared that I’d created a system that would run so smoothly and beautifully that we could all just glide along and let the machine do the work for us. 

So in this reflection, I’m going to bring you behind the scenes of Stuck on the Staircase, to how I went from feeling completely discouraged and languishing to finally coming to the place that allowed me to write the words you heard in that episode. 

I shared with you in our audio tutorial for this week that I am not naturally an organized person. As an adult, I’ve learned to carefully document things and have systems in place, but I don’t find the work of keeping myself in order particularly life-giving. I don’t need to be convinced that it’s necessary—and so I spend a lot of time doing it—but each time I get to the end of all of that organizational thinking feeling exhausted.

What I know now about project management—what it took over 2 years and 200 episodes to understand—is that project management is perhaps the most challenging part of podcasting, because it’s the puzzle that keeps shifting—but that shifting is an important part of the process. I think what’s so tiring for me about project management is that you can spend a lot of time and energy developing a great system that works perfectly—but then it changes again depending on the context and the people.

When it was just me creating episodes, and my only real goal was to make a new one every day, those checklists and spreadsheets were a sufficient project management tool, at least most of the time. As long as I looked at them every day, I could stay on top of the things I had to do that day.

But when I started thinking about monetizing, promotion, and listener engagement, my lists began to grow and become more unwieldy. Then Nate started doing this work with me, and I had to change my system further to include another person. For a while we were paying another podcast producer to help us out a few hours a week, so we had to make sure she understood our process well enough to know where she could be the most helpful. 

But it wasn’t until we began our first cohort of what we’re now calling the Kasama Collective that I began to understand just how essential project management was. 

I will forever be grateful for our first two cohort of trainees, who saw the beginnings of what we were creating and wanted to be a part of it. This course exists today because Sarai Waters, Winnie Shi, Melissa Lent, Alana Herlands, Eve Bishop, Isobel Obrecht, Elen Tekle, Michele O’Brien, Samantha Skinner, Shweta Watwe, and Clara Smith weren’t scared off by two creatives who were making no money but had an idea to teach people narrative podcasting by bringing them inside our own process. We didn’t yet fully understand what we were building, or that those first two cohorts would become the beta version for the course you’re taking now. I credit every one of our first and second cohort trainees with helping us to realize that vision and helping us to build the foundation for what we’re doing today.

The twelve modules we started with didn’t include this one, because despite the fact that I would spend hours every Sunday mapping out the week on giant post-it notes, figuring out how to give each trainee something different to learn, while also making sure they got to work on some part of an upcoming episode, it didn’t immediately occur to me that project management was something I needed to teach. 

This module exists today because Melissa Lent approached me one day and asked if I’d be open to letting her experiment with some project management tools that she thought might be able to help us out. There was a lot of creative experimentation in those first two cohorts, which was part of the fun of it. 

Unlike me, Melissa had a brain built for project management. She told me once that she watched project management tutorial videos on YouTube for fun. She’d seen my elaborate flow charts and giant post-it notes, and recognized an opportunity to grow in an area she was already interested in, but didn’t have any work experience actually doing. Her request was a gift I hadn’t known I wanted, but desperately needed. Every week my energy was zapped trying to figure out the weekly puzzle, and here was someone who wanted to not only engage in that puzzling with me, but who might have an answer to how to do it all better.

Over the course of the next few months, we tried out a number of different project management tools, often abandoning one for another when it was clear it wasn’t working. 

By the time Melissa graduated from the program, she’d helped us to identify three basic roles within each episode: scriptwriting, audio editing, and producing (our catch-all term for all of the details involved in making sure that the episode got out into the world). She’d gotten us set up on Notion, created a master task list, helped us develop guides and strategies for social media, and then handed off her creative experiment to some of our second cohort trainees who were equally enthusiastic about project management. Shweta Watwe and Samantha Skinner helped us build out our project management process further in Notion.

When it was clear that our trainees needed more structure than the freewriting approach to scriptwriting that had worked for Nate and I, we created forms to get people started. Alana Herlands helped me to build a clear process for taking ideas through the early stages of scriptwriting, and on into the production process where they’d become episodes.

It was a beautiful system—something I never could have dreamed up on my own—where all of the knowledge we’d accumulated lived in one place, and we all knew where to access it. 

When we began our third Kasama Collective cohort in the fall of 2021, I was optimistic. I’d spent the summer refining our process in Notion, creating videos for how to edit audio, step-by-step guides for scriptwriting building personal pages for each of our incoming trainees, who I was sure would joyfully embrace all of this work that had been done before them.

But within a couple of weeks, it was clear that something wasn’t working. 

We’d settled on Notion as a project management tool because Melissa and those first two cohorts loved it, but our third cohort hated it almost immediately. The system we’d labored over to make user-friendly and comprehensive they found  overly complicated and confusing. 

By the time we began working on Stuck on the Staircase, I was frustrated, overwhelmed, and deeply discouraged. It felt like the harder I worked, the less of a difference it made. I knew that we were offering everything we’d promised—but it wasn’t working for everyone in the same way. Some of our trainees were thriving, while others were visibly frustrated. After weeks of bending over backward to try to accommodate the requests of the trainees who were frustrated by the current system, I was too worn out to see clearly how to adjust. 

It was thanks to Stuck on the Staircase, and that very arduous process of trying to understand how to manage my own languishing, that I came upon the Beginner’s Mindset. 

When I took a step back from the situation and reminded myself that I was allowed to be in process, I could finally recognize what I’d known intuitively all along: that project management isn’t static; it needs to be able to flex and adjust depending on the context and the people.

When I put aside all of the hard work we’d done crafting pages on Notion, and took a step back to see podcast production with a beginner’s view, I saw something I’d never seen before: I could break up the process into three distinct phases: pre-production, production, and post-production. For each of the three defined roles of assistant audio editor, assistant editor (or writer), and assistant producer, I identified three main goals in each of those phases. We still had the guides available for anyone who needed more details on how to reach those goals, but at least we could say to someone, “this week, you’re an assistant audio editor and you’re in the pre-production phase, so you’ll be selecting music and creating episode trailers,” or “this week, you’ll be an assistant producer in post-production, which means we’re getting the episode out there through social media and following up with our guests.” Each phase lasted one week, and each role would stay in that role for three weeks, from pre-production, to production, to post-production.”

When I presented this new idea to the team, I could see relief on their faces. One of them actually cheered. From that point on, we almost entirely moved away from Notion and back to email. It was a different group with different needs, and so we did our best to adjust. It had taken a lot of spinning my wheels to get there, but it helped people to see their roles a little more clearly. It took bringing myself back to that beginner’s mindset to be able to see it.

But here’s the thing: while those phases made a lot of sense to that particular group, it’s still not how I think about podcast production. For me, the process is a lot more fluid. Different episodes require different timelines. It’s rare that any episode behaves on a three-week cycle where every week’s work stays perfectly in its little box of tasks. 

Thinking back to the creative personality module and the Big 5 personality test, I realized that the people in our third cohort were significantly different than the ones we’d had in our first two. Without exception, every single person in those first two cohorts was high on openness, and found the process of building something together exciting and invigorating. They were also highly collaborative, which was why it was so much fun for all of us to build something together. But this was only true for about half of the people in that third cohort—not surprisingly, the half that was high in openness.

For the first time we began to understand that our program wasn’t for everyone—at least not with its current structure. But the people weren’t the only thing that was different. We were also in a very different moment in time than we’d been in those first two cohorts. 

When we began the Kasama Collective in January of 2021, vaccines were not yet available to most of us, and life was still happening online. For the better part of a year, we’d barely left our homes. We’d all but forgotten what it was like to get together with friends or go to a concert or a party or go on vacation. Most of our trainees were unemployed, or in jobs that didn’t require a lot of time or creative energy, or in school with classes still meeting online. Teaching these materials live on Zoom calls and doing online work sessions to create episodes together felt like a gift to all of us, because for months, life had been lonely and maybe a little boring. We bonded over these modules, over the challenge of building something new together. We all naturally gravitated toward that beginner mindset together, creating something we didn’t yet have the vocabulary to name. It was a hard and beautiful season of life, one that I will always be grateful for. The Kasama Collective exists because of those unwieldy first months of learning together.

But I am equally grateful for the challenges presented by that third cohort, when the world had opened up and every single one of our trainees had demanding full-time jobs. People were busy and tired, no longer eager to attend meetings on Zoom. 

It was while we were working on Stuck on the Staircase, when I was learning to develop a beginner’s mindset all over again, that Nate and I began to get a vision for the course you’re taking now. We realized that there was a need to create materials for people to learn that didn’t require them to always be on their screens. Thanks to one neurodivergent trainee, we spent a lot of time thinking about accessibility, making sure that we provided transcripts for everything, and only made things as complicated as they needed to be. We moved away from Notion and toward a simpler structure, one that only taught the trainees what they needed to know. And we started thinking about how to build these  modules in a way that didn’t require live teaching, but that could allow for people to come back to them again and again in the future, so that if life got stressful or they got behind, the teaching and training would still be there for them when things slowed down. 

And so we adapted once again. Even now, as we’ve built this course, we’re seeing ways to adapt again for future classes. It’s taken me a long time to understand that that is actually a good thing. That it’s only when we get stagnant and resistant to change that we stop growing. So if you’re languishing now, or feeling frustrated with a coworker or just not feeling like things are lining up in your life the way you’d hoped they would, I hope that this module encourages you. I hope that you’ll know that you’re in good company even in the languishing, and that where you are is not just a valley, but a place to learn and grow.

So if you’re languishing, or getting stuck in a project management puzzle, take a step back—take a break if you can—and develop a beginner’s mindset. Sometimes that means asking someone else’s advice, maybe even from a different industry. My therapist friend Emily ultimately was the one who unlocked both that episode and that project management puzzle for me. She reminded me that nobody really has it all figured out, and that having that expectation for ourselves isn’t realistic. Once I could give myself permission to learn something all over again, I was able to see the problem differently and come up with a solution that maybe wasn’t perfect, but at least provided 

some relief.

One of the best things that came out of creating Stuck on the Staircase—and all of the challenges we had in once again adapting our project management system, was that we recognized an opportunity to bring in someone who could oversee that process better than we could. 

A couple of months after this episode was made, we asked Melissa Lent to come back to work with us—this time as a project manager. She joined us while that third cohort was still going, so she got to see all of the places where the old system was breaking down, help us identify why things weren’t working smoothly anymore, and advise us on how to adapt to the situation. Part of that work was this course as you’re getting it now. 

I said at the beginning that if there’s only one thing you take from this module, it’s the ability to adapt and adjust. While I still don’t love project management, and I’m endlessly grateful for people like Melissa, something I’ve come to appreciate is that the changing demands of this work mean that it never gets boring. Even the ability to accept the changes and recognize them as opportunities for growth and improvement has a subtle art to it. Over time, I’ve come to appreciate this as one of the greatest gifts of this work, that our autonomy and ability to change production schedules or shift workflows means that there’s a lot of grace built in. I love that we’re in a medium where even big-time podcasters can say, “you know, this week was a hard week, and so I didn’t meet my deadline in the usual way.” 

I’ll never forget hearing Ira Glass in an episode years ago. He was obviously sick, and his voice sounded awful, which he admitted. I remember thinking, “why couldn’t they just wait until he was better to record?” I understand now that even at This American Life, they’re moving fast, having to adapt. Some weeks the plane flies smoothly. Other weeks you have to make an emergency landing. But one way or another, we adapt. Each time, we learn a little more about how to do this work better—and how to extend grace to those around us when they’re having their own crash landings.