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The Future of Content episode 33: Leadership Coaching with Jen Dary

37 Min. ReadDigital strategy

The Future of Content Episode 33 with Jen Dary

Key ideas

  • Coaching and counseling are different mediums used to reach for the same result.
  • In uncertain times like these, the only thing we have control over is how we show up every day.

Often, when we think of coaches, we think of someone involved in the life and performance of an athlete, or someone who is responsible for pushing us and bringing out the best in us. Jen Dary is a leadership coach, mom, business owner, and the founder of Plucky, where she works with individuals and companies to create healthy dynamics at work, and her idea of coaching is very different.

Sometimes we think that coaching is going to be a retention tool, but my view of coaching is that whatever is happening underneath the surface of a person is going to happen quicker and more efficiently after coaching sessions. So if your issue is that you’re having trouble with a coworker or a challenge with work-life balance, we’re going to get real clear on it and get some tools and structures to lift you out of that quickly. And I really do understand that feeling of ‘are we opening a can of worms?’

Whether we see a coach or a counselor, we’re going to get constructive feedback. Some of that feedback may be hearing things that we need to but may not want to. For Jen, feedback is a critical piece of her role as a coach.

The whole content of feedback is what are the words and the order of words that I say to not have a negative impact on the person I’m giving feedback to. Giving critical feedback means having to take an editing tool to figure out how to convey the exact tone and touch that the person needs.

Jen doesn’t believe in asking the usual coaching or one-on-one questions. She digs deep in her sessions, and through products and services offered by Plucky, teaches others to do the same. 

I have a one-on-one starter pack, which is for managers. There are questions that any manager can use, and I have the manager pack for managers of managers because they’ll arguably ask a different level of questions—more strategic than team-level. The cards help cut through the staleness. We’ve all played into our roles for so long that any deviation will be a bit of an energetic lift. It can be hard to bring up something that you’ve never talked about before, even though we may want to.

As a coach, Jen focuses on bringing out the leader in those she works with. We may not see ourselves as people with influence, but Jen does.

I think that leadership is something that every person has the potential for. I would even say that people are leaders in some tiny part of their life. If you’re at the grocery store and you see someone trying to figure out who goes first in the line, and you tell them to go ahead of you, that’s a leadership moment. We all have threads of leadership. Some of us have so much leadership at home—if you have kids, there’s a lot of leadership there.

There is more to leadership and coaching than one might think. Jen works hard to bring a creative and unconventional approach to coaching, and it is refreshing!

Stream episode 33 now, or subscribe on your favorite podcast platform below.

Episode transcript

Note: This transcript may contain some minor wording and formatting errors. Apologies in advance!

Todd Niekerk: Welcome to The Future of Content. I’m your host, Todd Nienkerk. Every episode we explore content—its creation, management, and distribution, by talking with people who make content possible. Our goal is to learn from diverse perspectives and industries to become better creators. 

The Future of Content is brought to you by Four Kitchens. We build digital content experiences for ambitious organizations. 

Today, I’m joined by Jen Dary, leadership coach, mom, business owner, and the founder of Plucky, where she prepares the next generation of leaders to lead with empathy, vulnerability, and confidence. Today, we’ll be talking about the content of coaching. Welcome to The Future of Content, Jen.

Jen Dary: Thank you. Thank you for having me. Sometimes it’s so fun to talk about the liberal arts versions of tech. I feel like your questions and thoughts about content is not the required courses, right? It’s like an elective, but it’s even more spicy.

Todd Nienkerk: It’s a writing component.

Jen Dary: Yes, exactly! 

Todd Nienkerk: We all remember those. So we’ve known each other a long time. We first met at the very first Bureau of Digital Owner Camp before it was even called such a thing. How long ago? 10 years ago, I think? Hard to believe. 

Jen Dary: I think that’s right because Plucky is eight-and-a-half and it was a good year-and-change before I started Plucky. Dang! A decade later!

Todd Nienkerk: And for those listening who are in the Bureau of Digital is a professional organization, that’s actually really closely related to what we’re going to be talking about. Professional organization of digital creative professionals. It’s like a support group for people who own agencies or run teams or do digital project management and stuff like that. It’s where we all get together and kind of cry on each other’s shoulders and complain about stuff and then go to dinner. It’s great!

Jen Dary: It’s literally called my funnel. 

Todd Nienkerk: I mean, just you reel in the leads. That’s fish in a barrel. Yeah. So let’s actually, let’s talk about that a little bit. So what is Plucky and what do you do at Plucky?

Jen Dary: So like you, so lovingly said, Plucky is a coaching and consulting firm. And what I generally mean by that is that about half my time, or maybe a little more at this point is spent one-on-one coaching with either current leaders or managers or emerging leaders or managers. And we can get into that in a minute for why I think that’s such a crucial population to coach. But that is a big chunk of my work. And then in the other part of my life, work life, I teach. So I have a course called, “So Now You’re a Manager,” and it really handles that kind of onboarding ramp into the identity of a leader. Some with power, someone who has impact at a greater scale than an individual contributor. And those, I just graduated my 21st cohort, those groups. So that has been going for a good while now. And we’ve seen a lot of people come through and that is really fun for me because it’s groups and not one-on-one. One-on-one is awesome too, but you know, it’s a different thing. 

And then the last thing I’ll say is that, there is sort of a product— Little wing of this house over here, where I’ve invented some different tools that people can use when they’re working together. And, uh, that’s a very creative part of the world over here. And I’ve really enjoyed as a founder, but also, again, not only as a business person, but as a creative person, I’ve really enjoyed making this a multishaped or multifaceted business, and not just, “I’m a coach, I coach all day long,” you know? It’s more fun for me, and maybe people listening who are founders might find their way into a more fulfilling long-term situation if they can wear several hats. 

Todd Nienkerk: And one of these tool kits or tools that you built is, just as an example, is like a big oversized deck of cards that have really good questions to ask people during one-on-ones and check-ins that go beyond, “So how are you doing?”

Jen Dary: Totally. Talking about content, really, what would happen, Todd, is that I’d be coaching someone and we’d have a big question that came up. Like for example, I just used the other day, “Why is manager the right role for you?” So there’s a nice juicy question. I would be coaching someone that would just come up kind of anecdotally.

And then I would say, “Okay, that’s good.” At the end of the coaching session, why don’t you take that and use that with your one-on-ones next week? You know, you have managers reporting to you, ask them all that question. And we had just seen it proven out that this person was able to unravel a lot of self-awareness, but there was this hesitation, like I’m not Oprah. Like, I don’t know if I can just show up with that kind of question to a one-on-one. So I was like, this is weird. I’m observing this over and over. Well, that one is pretty literal, right? But even if you just said, “What do you want to be doing 20 years from now?” There’s another one. That’s a little more—

And people would be like, “Hmm, I don’t know if I know.” I mean, you’re talking maybe sometimes about extreme introverted mathlete types who have gotten promoted into let’s just say engineering leadership. So I was like, well, this is interesting because we have a thing that works and we have a population that it could work well for, but there needs to be cred in the middle. Like you need your identity to shift into being the kind of person who brings these things up instead of just how’s the sprint planning going. You have to elevate it. Right. So I thought, “Oh shoot, they just need something to blame that on. So I made these cards and I thought, “Here” —

Todd Nienkerk: I’m going to pull from the deck and read the card, and yeah, not my fault.

Jen Dary: Exactly. And that really was a thing. It seems such a simple thing, but I realized that it was like an identity stretch for them and all this stuff works. You just sometimes don’t believe that it’s your identity yet. And so it’s a funny little product. It sells very well. It’s really exciting.

Todd Nienkerk: So these— This might be a little bit of a tangent, but I’m just now drawing a connection between this, what do you call this product by the way? We should give it a name. 

Jen Dary: Oh yeah. So I have the one-on-one starter pack. So that’s for you or just plain old managers. Right? These are questions that you pull as a manager. And then I have the manager pack that’s for managers of managers, which arguably you’re going to ask a different level of questions, more strategic team level. Stuff like that. 

Todd Nienkerk: Okay. So you sent us a couple of those years ago when you first created the starter pack. And it wasn’t long thereafter that I started noticing other things kind of pop up in different areas of my life. That involved cards with evocative questions, right? This is like a thing now. This is a thing.

Jen Dary: Totally. I was probably the influencer Todd, let’s be real. 

Todd Nienkerk: You put it out into the world and it manifested and yup. So for example, my. My wife picked up, you know, one of these like decks of cards that are sort of like allegedly games, but they’re really like, we’re going to have structured conversations about things. Uh, and, uh, and, but don’t blame me, blame the cards. I just drew the card. It’s not a tough question unless you think it is. You know, we’ve been together 20 years and still like, oh, I didn’t, you know, I didn’t realize that about, you know, it’s a surprise every day because of the cards. So these, this tool, this way to, to kind of blame it on the card, blame it on the tool, right.

I’m just a vehicle for answering this for asking this question. I’m not inventing it. That’s a pretty smart way to do it. Do you find that that’s a way that a lot of people have to kind of step into a manager or leader role? Or is that more of a, well, I’ve been doing it a while and now I feel stale and I need something new, or both?

Jen Dary: It’s a good question. I think the staleness is riffing for me on what you just laid out in your own personal relationship, right? We have played into roles for so long that it would be a little bit weird if we talked about something different, or if we showed up and I, instead of ordering pancakes, I started ordering like an omelet. You know, we have these routines and patterns with each other. So any deviation from that is going to be a bit of an energetic lift. There’s going to be an eyebrow raised, there’s going to be a turn of the head, like, “What’s happening over here?” Right? You’re not doing what’s expected. And that can be hard, right? It can be hard to bring up something that we have never talked about before, or that, “I’ve never met you before and I’m going to throw something out.”

And so in those transitional—again, I keep saying identity—but I really do think it’s a big part of it. Those transitional, or sort of off-the-beaten-path moments, sometimes we need help. We need help figuring out how to word it, or what would I say? Look at feedback. I mean the whole content of feedback is what are the words and the order of the words that I say to not have a negative impact on the person hearing the words. Like, oof, talk about content creation—feedback, critical feedback giving is, you know, you gotta take a real editing tool sometimes to that to figure out how to really convey the exact tone and touch of it.

So I do think that these questions, or also the way we see into new roles, like, “I got promoted now I’m a manager. I used to be peers with that person. Now I manage them. Someone talk to me, someone tell me how to do that.” You know, someone give me words that it sounds natural for me to say, “Well, here’s your performance review, old friend,” you know? Like it’s really hard. And it’s hard to also read books about that. So it’s very fulfilling for me to have that live. Be it in one-on-one, like I said, or in a class where we can all laugh at each other, like with each other also, um, I think it really normalizes that experience. Cause it’s not you, it’s the whole thing.

Todd Nienkerk: Yeah. There’s also, I think an element in the— And this might be a business owner versus a leader versus a manager in the company, but it took me a very long time to get comfortable with having conversations and asking questions about people’s career paths because to be completely honest, I didn’t want to know. I didn’t want to find out something I didn’t want to hear about like, “Yeah, you know, actually, I’ve kind of been looking around.” Like, how about I not facilitate that? Like that’s like a very kind of selfish thing to do, but also you’re afraid of. But then “I got to replace this person and, oh, they’re so important. And what do I do?” And it takes a long time and a lot of maturity to get to the point where you realize like, hey look, your job is to help this person have a fulfilling career. Regardless of whether they’re, you know, at your company or somewhere else. And if they decide to leave, then that is— They have the right to make that unilateral decision. And that means that they don’t belong there anymore. And, you know, find somebody who does. It just kind of speeds up— Maybe it feels like it speeds up the process. But do you actually think that it kind of slows it down because you’re making it a conversation? How does that work? 

Jen Dary: Someone just talked to me about this because I was coaching someone at his company. And as we coached for a while—almost a year—in the end, she gave her notice. And her boss was like—he was being super chill about it—but he was like, “I think I thought that coaching is going to be a retention tool and this is kind of awkward or weird.” And I was like, “I completely understand where you’re coming from.” My view of coaching is that whatever is happening underneath the surface, it’s going to happen quicker and more efficiently. So if your issue is trouble with a coworker, or a challenge with work-life balance, or things like that, hopefully, we’re going to get real clear on it and get some tools and structures to lift you out of that quickly. Hopefully, right?

If it is a deeper unsettledness with where you are, then probably it will lead to that kind of situation. But in the meantime, you’ve retained the person for a year. And so I do really understand that feeling of, “Are we opening up the can of worms? Should we just ignore it and not say anything?” To be honest, I think realistically speaking, there are seasons for both. There are seasons when, if you just had 10 people resign in a hundred-person company, be cool in the next couple months of one-on-ones. You want to be supportive of everyone, but also maybe. Don’t look under the bed, you know, just for your own sanity, because you know, you need to keep the business afloat. And so that is a moment where you might prioritize your own self-care and support. But yeah, eventually it is very helpful to have a flashlight shining ahead for who’ll be here and who won’t, but it’s daunting. I don’t say it lightly. 

Todd Nienkerk: Do you find that in producing content for these different roles, that there are maybe different mediums or different tones or different topics that work better for leaders versus managers versus individual contributors versus even business owners or shareholders? What do you think? Is there a difference or is there, is it more of a— Is it a company culture thing that dictates what kind of medium works best?

Jen Dary: That’s a really interesting question. To be honest, I think that leadership is something that every person has potential for—or even I will go so far as to say they are a leader in some even tiny part of their life. Even if you see you’re in the grocery store and you see a couple of people trying to figure out who goes first in the line and you’re like, “Oh, go ahead, you were here first.” That’s a tiny little leadership moment, right? So whether you’re an individual contributor all the way up to like chairman, whatever, you have little threads of leadership that are possible for you. Some people have so much leadership flex at home. Like they have six kids or frankly, two kids. I have two kids. There’s a lot of leadership flexing there, that you spend it all at home. And therefore what you want at work is not that. And that season, maybe when your kids are grown or when there’s not as much, depending on you at home, you might be more open to a more, uh, like specific promotion into leadership.

But I think leadership is knowing who you are. I should say good leadership—strong leadership is knowing who you are and who you are not, and making space for everyone in the room and then making the decisions. Because the leaders who are too soft in my eyes or too friendly or too, “Hey, no, we’re all flat here,” or “I got to keep everybody happy,” in truth, nobody wants to be like that. They want you to make the decisions. They want you to fire the terrible clients that are losing sleep for them every night. They want you to let go of the person who it seems like will never be fired because they’re brothers with, you know, someone here, like, they want you to take that action because they don’t have power to themselves.

And even if you just expand leadership to the country and the world, we don’t all have expertise in all this stuff going on by any means. So we’re like, can you just do something? I mean, that’s how I feel when I look at the news: “Who’s doing something? Who’s stopping this?” And that’s what we want. We don’t want them to just say we’re all the same. Because power matters. 

Todd Nienkerk: Yeah. In coaching people at these different levels, do you find that there’s like a different way that you have to approach that conversation? Is there sort of like a weird power thing that some people have walking into the room or, or what?

Jen Dary: Yeah. Well, the thing that comes up for me is often people come to new manager training, right? So now you’re a manager, and then they’ll leave and they’ll say, “Damn, I wish my boss took this class.” And then we laugh about that because, you know, it’s so real that people have gotten promoted and promoted without an official training. And at some point there’s kind of like, you know, those things. The things you drive over and then you can’t back up because it will blow out your tire? That’s like prof-dev for founders who have been doing it for a while. It’s like, “Ruh-roh. Well, it would be embarrassing if I go to that class, but I also don’t know what the hell I’m doing.” You know?

So, but when they say that to me, like, Jen, you should have a, “So I’ve been a manager for 20 years class,” I always laugh. And I’m like, yeah, but these clowns—no offense to you, it’s me, too. But like these clowns would need to be taken to like Bora Bora and ah, the Tahiti manager training. Like nobody’s coming to like my virtual Zoom. They’ll sit there and then they’ll email on the side, right? Like, it’s a completely different medium that you need. And I’m not saying that can’t exist, but if you think of like, I mean, this kind of goes back to Bureau, which I’ve observed and it’s, it’s not shade to Bureau, but like when you get 10, 15, 20 powerhouse founders in the room, there is a lot of posturing, and frankly it is inefficient sometimes. And you’re like, God, can I just have a one-on-one conversation with somebody to actually say real stuff? Because there’s so much commercials going on, if I can say that? It’s not because anybody themselves is fake. It’s just what happens when you have power in the room like that. 

Todd Nienkerk: Yes. And that, um, any conversation like that has a tendency— You put it very eloquently. When you get a certain group of people in a room and they’re there to talk about what’s working and what’s not in their businesses and to share and learn. There’s going to be a lot of, some version of posturing, whether it’s like, well here, let me just sort of brain dump all the things that we’ve done and whether they’re a good idea or not. And some people who kind of overshare and people who under share. And it’s really easy for, I mean, you can tell within probably the first hour, like who’s going to be the big talker for this weekend, you know, and it’s hard. It’s really hard to facilitate that kind of group, because at some point somebody is going to get embarrassed. Like somebody is just going to have a real mirror shown to them and we’re all waiting for it. And it always happens, but sometimes you need it, right? 

Jen Dary: I mean, heck yeah. But also the weight of the facilitator in that moment is so important, even when we start talking about DEI efforts. So, you know, not to be simplistic about it, but are women sharing? And are women just being saved in the conversation? They express, oh, this isn’t working so much. Are people just swooping in to say, “You’ve been doing it wrong? Here’s what it is. Just an observation.” Are other underrepresented groups being told, “Here’s your solution”? 

People really like solving other people’s problems and it, it, you have to be really careful when you get people together in that sort of sharing space, if you don’t have firm boundaries or firm facilitation, because it immediately evaporates into kind of what you’re saying, which is one or two people are going to talk a lot and everyone else is at some point just going to sort of check out. And that’s not specific to that conference, right? That’s just every conference. So I think having very solid facilitation in these moments, especially when you’re with people in great power, is the only way I will attend a conference like that anymore, because it’s a waste of time. And it’s just thin.

Todd Nienkerk: Something that I’ve found works well in those environments in terms of constructing content and rhetoric—and I’m actually doing it right now—is always framing it in terms of, “Well, this is what I’ve found has worked for me.” And not, “You know, what you ought to do is this.” But rather “Well, in my experience… ” And there’s all kinds of these professional support groups out there. One of them—I forget if it’s EO or Vistage—I think it’s EO that has a rule. I forget what EO stands for—probably like Entrepreneurial Organization, I think is correct. Hey, let’s, let’s go with it. No offense to anybody at EO or, you know, I don’t mean anything by that, but one of their rules is at any point during one of these kinds of meetings, you can never tell somebody what to do. And you can only talk from firsthand experience. So not, “I’ve seen people do this or that”, or, “You know, I have a friend who did…” you know. Nope. Your experience says, “This is what happened to me. This is what worked for me. This is what I’ve observed,” and leave it there. And don’t tie that to, “You ought to do that.”

Jen Dary: That’s so classy. And you’re reminding me that for me, the difference between coaching and consulting is that consulting is I’m the expert. You ask me questions. I tell you the answers, so you do what I said. Coaching is when you have your own answers. You just can’t see them yet, or you’re not brave enough yet, or a million other reasons. So you’re going to say stuff to me, and then I’m gonna ask you questions and then I’m gonna make some observations and then you’ll know what to do. That, um, there’s probably a medium space consulting or something, you know, where it’s like mostly coaching, but every once in a while I’m like, “Hang on a second, I got to tell you a little truth here,” you know? And that spectrum is similar to what you’re describing, which is, are you a person who is out telling the world, you know, how to solve all their problems? Are you also a listener? And are you a person that lets someone else find their way based on a couple of tidbits of experience you’ve had to share?

Todd Nienkerk: In this process of coaching and providing observations and not consulting—not giving advice—what do you do to try to understand— How do you construct that? How do you, how do you make observations in a way that, you know will lead somebody to their own conclusion while also not kind of putting your own consulting and then therefore like, you know, opinion, spin on it?

Jen Dary: Well, that’s an interesting question. I was just coaching someone, I don’t know, five hours ago, about something similar where she has a crossroads coming up in her career. And so there’s a bit of transition happening or she gets to decide a lot of directions soon. She has a few options ahead of her. And she’s kind of paralyzed. You know, there’s a few options and she’s not sure there’s pros and cons to each. So I said, tell me about a time when you had a similar situation previously in your life, like where you had a number of options and you had a big decision. But not a big decision—yes/no. A big decision between three, four. I said it could be like college childhood, like whatever. And she came up with an example and then I said, okay, what, based on that, how do you do best with decision making? Did you make a good decision because you took a walk on a mountain? Did you make a good decision? Because you mulled it over, you called your mom, you made pros and cons lists, you meditated, you did tarot cards. Like what is the recipe for you, this individual in front of me, how do you make your best decisions? And then based on the data, literally, she was like, “Well, this time, the best way I made a decision was this; this other time when I had a crossroads decision with this,” I said, “Oh, interesting. So both times, you went away for a couple of days by yourself and you came back and you had heard yourself, so great. What are you doing this weekend? Can you go away?” You know, and that is the kind of thing that I think is interesting to track because in my eyes, life is a giant science experiment. We are running hypotheses and experiments all the time, and you can just live your life forward like that, or there can be moments where you say, “Hold up, this is actually not brand new to me. I have had an experience previous to this that has a similar vibe. What did I do last time? Did it work? Did it not work? What can I replicate this time, now that I know more about myself?” And also you’re definitely going to have a crossroads in the future. So, what do you want to mess around with this time that would give you knowledge to leverage next time? So it’s sort of this, you know, for me, I’m asking her based on your experience, tell me your deal. Like, what’s good about that? I might have opinions, but she’s giving me specific anecdotal data. And I think guiding her back to that helped her figure out, “Oh, I have done this before. It’s not as daunting as I think. I made my peace with the decision last time and I didn’t have regrets, so I can do that again.”

Todd Nienkerk: And that kind of approach is very similar to what therapists do, right? It’s listening, it’s asking probing questions. It’s kind of turning the mirror to the person speaking and asking them to like, think through things or clarify things and in doing so they’re actually clarifying it for themselves and not necessarily, right? All of that stuff. Do you think that that, that coaching is drawing from therapy, or therapy is drawing from coaching, or where do you think that interplay is? I guess by the way, also, I should probably say that, I know I’m misusing the word “therapy.” It’s probably like “counseling.” I’m probably using the wrong word.

Jen Dary: Well, that’s okay. We’re ballparking words. That’s fine. In my experience, and I have had therapists and coaches in the past, but in my experience, therapists are way more listeners. So they might ask a question, but then they’re listening. And coaches are like, “I’m going to get in there with you.” So a therapist—again, this is so broadly speaking, right? It’s mostly my interpretation, but for me as a coach, I’m taking notes the whole time you’re talking, and then I will stop you once in a while like, “Hang on. Let me read some things back to you. What does that sound like to you when I say …” Right? And so I’m like playing with you in the mud here, like, okay, well that’s cool.

And then I actually have these postcards that— People say such smart shit all the time, Todd. Can I say “shit?” People say such smart things all the time—

Todd Nienkerk: People say smart shit like, “People say smart shit.”

Jen Dary: Exactly. Boom. But they don’t know, they said these things. These things could be like on bumper stickers or like T-shirts. So I write these things down and then like once a week on a Friday, I watch some TV show on my couch, and I go back on my notes and then I have these postcards, which obviously your listeners cannot see, but it has a space to write the quote. And it says, “[Blank] said this on [blank.]” I write the date and on the back, it says, “Hey, so-and-so, one time while you were talking, you said this really smart thing.” And so then I write a little thing on the bottom—here’s content, right? And I send it to them, and people get to see how smart they are. It arrives in the mail. Some of my clients are like, “Behind my desk is like wallpaper, because I have all these postcards from you.” And it’s these reminders of “you are so smart that one day, and you said this really real thing.” And I have to be kind of careful, because sometimes that smart thing is like, “I’m realizing my boss is a jackass.” And then I’m like, “I can’t send this to the office. I’m going to stick this one in an envelope.” You have to be kind of savvy. But coaching to me is not just listening. It’s very interactive, or at least the way I do it. And there’s probably not a canon there. 

Todd Nienkerk: Well, let’s take a short break. And when we come back, let’s talk about your upcoming e-course.


Hey everyone. We’ll get back to the episode in just a moment. I wanted to quickly tell you about Four Kitchens. You probably know that Four Kitchens creates websites, but we do so much more than that. We help nonprofits increase donations, we help universities enroll more students, and we help media companies streamline their streaming platforms.

Our team of Web Chefs can help you make better use of your content scale, your web team, and create world-class digital experiences to find out more about how Four Kitchens can help visit us at Now back to the episode.

Todd Nienkerk: Welcome back to The Future of Content. Our guest today is Jen Dary, leadership coach, and the creator of a brand new e-course called “Everything is Fine: 11 Habits to Create Stability at Work.” So you’ve created a course before. “So Now You’re a Manager” is the first one, and now “Everything is Fine.”

Tell us about where this came from and, um, what this e-course is all about and like, how is it structured as a piece of content? 

Jen Dary: So the difference, the big difference between “So Now You’re a Manager” and this one is “So Now You’re A Manager.” It used to be, pre-COVID, two days in person; it is now three half-days virtually, but “Everything is Fine” is purely content. You and I never talk. You take the class, right? So it’s through a platform called Teachable. Uh, the reason it exists is, gestures at world around her. You know, like it’s rough out there. And, you know, it’s quote-unquote “candidate’s market.” So people are quitting their jobs every hour and everybody is like, “What is happening?” You know, it’s been two years of pandemic. I don’t need to go on with the disasters around us. But, I have just noticed two months ago, pretty much, every time I hung up from a coaching call, I was like, “All right. I either got to send them flowers or jump on a plane and take them out to lunch.” Like every person was rough. And I think it was Omicron time. And we were like back into that, and it’s just, who can plan anything and people are tired, and all that. And I thought, “Oh God, what can I do to, hold everyone’s hand? And not just sit quietly with you, but also be like, ‘Hey buddy, why don’t you try this today?’” You know, like how, how can I put myself out there?

And really a lot of my job, Todd, the challenge of it, and for Plucky going forward, is scalability. I am one person. I’m very good at my job, but I’m one person. So I can only do a very good job with the number of hours I work. So things like the product is not only an opportunity to provide a different price point for people who can’t afford coaching or coming to a training, they can spend 35 bucks on a pack of cards and add that element of, um, prof-dev. But it’s also my ability to scale. So when you come to think about an e-course, something that I don’t need to be live for, I came at it with this vibe of “everything is fine,” which is that meme, which is like the world is burning down around you but you’re just like, “No, no, no, it’s fine.”

And, uh, I really wrestled speaking of content, I wrestled for a few months with, um, what was it? Would it be 30 days of stability? Should it be four weeks of stability? Should it be like, I don’t have control over whether you started on a Monday or a Thursday, so that’s tricky. And also 30 days of content, like, oh God, you don’t— I mean, go do Peloton. You know what I mean? Like you don’t need 30 days of content from me; that’s a lot.

And I, I mean, I was in thesaurus for hours. So in the end habits seemed like the right vibe that I was going for here. Little micro things I can show you, teach you, talk you through examples, and then you can put it into practice and you get to choose. You want to do it every day? Great. You got 11 days. You want to do it once a week? Great. You want to do it once now, and in a year? Fine. You have access to the course. So, and then the reason I did 11 is that 10 is just too classic. Yeah. Shake this up. And now I’m like, Ooh, this is a template with which I teach many courses—11 habits for whatever, getting promotion, you know, all kinds of stuff.

Todd Nienkerk: I also am reminded, uh, we were talking about, you mentioned the thesaurus thing. How much time it’s we probably both spend in thesauri, trying to figure out more articulate ways to, to be in the world. Uh, you are a graduate of the Iowa writers’ workshop, if I remember correctly.

Jen Dary: I went to the summer camp.

Todd Nienkerk: I remember having a conversation with you 10-something years ago about Garner’s Modern American Usage and Chicago style—like just geeking out over style. It’s so esoteric, but, uh, it’s so much fun, right? 

Jen Dary: Oh yeah. And we didn’t even talk about this, but two weeks ago. I finished my first book.

Todd Nienkerk: Congratulations. That’s awesome! Fiction, nonfiction? What are you doing?

Jen Dary: So it’s a memoir. I was very sick about five years ago, six years ago, almost. And this is a memoir of that time and, uh, it’s called I Believe in Everything. And it’s a really good book. And I’m now talking to agents and trying to get that out there. So, it’s so funny, you talk about the source there. Like, I mean, when you have a piece of writing that is such great length, you can’t— It’s not a newsletter, it’s like a fucking book, you know? So I, especially at the end, I had to go away to a hotel for a night. So I could, just in the same mental time, read the whole thing.

Cause by the end you’re like, “Wait a second. Is that the same tone that I used early or not?” You know, you can’t dip in micro, it’s such a big piece. And I mean, honestly, by the end I was like, “Do I even speak English?” Like none of this makes sense anymore. 

Todd Nienkerk: Wow. What an undertaking. Okay, please come back when you begin your book tour and we can talk about that. Oh, that’s really awesome. That’s quite an accomplishment. 

Jen Dary: I thank you. I have been working with a writing teacher for a couple of years, and she’s awesome. And she always tells me,  “Oh my God, you’re going to be such a get for some publishing house because you just like, are willing to sleep on anybody’s couch and just like, go do a book signing or a book tour there.”

And I’m like, “Oh yeah. I’ll rent a taco truck and drive around the country.” You know, that to me, that because without getting too far into it, the message of the book is, uncontrollable things will show up in all of our lives. This is very similar to “Everything is Fine,” right? Uncontrollable stuff shows up. There are ways you can get through that. And this is not tips and tricks—it’s literally the life story that I lived. But even if you don’t have the problem that I had, the health problem that I had, you can do hard shit. There are ways to be very deeply brave, either in support of someone going through something crisis oriented, or if you are in a crisis. It’s all very related, Todd, to my work in the world, which is coaching, which is like, you got you; you’re you; you know yourself. 

And so if you can kind of remember that it’s not lonely, it’s actually you keeping yourself company. Whether that’s in a health situation or a work situation or a management situation, you know, like in all these ways, I guess my work in the world is to just remind people that you’re okay and really hard things will happen. But, uh, at the end of the day, everybody’s pretty broken and it’s the people who are pretending they’re not that I don’t want to hang out with at all. You know, I’m just like, “All right, well, you’re just in denial, but come talk to me when you realize the deep-seated problems you have, then we’ll be friends.” 

Todd Nienkerk: Going back to your e-course, “Everything is Fine”—creating stability at work. So this, this was created in reaction to everything that’s been going on in the past, you know, well, a long time, but particularly the last couple of years. What role does stability play for people at work in general? And why is that a desirable thing that you’d want to achieve?

Jen Dary: Well, part of it is this landscape of folks leaving their jobs, right? So I’m not even necessarily talking to the people who have left. I’m thinking about the people who are still there. So you have this ever-shifting landscape—you show up at work, person to the left has just left. You show up at work the next day—person two tiers above you has left. And that kind of transition—this is just one example—but you show up and you don’t really know who’s going to be here. What’s the pipeline look like? Like all of those questions could have a major impact on how you feel confident about the work you did that day. If you feel like it was a good quality, are you covering three people’s jobs? All of that. If you go home and the world is highly unstable, which it is right now, this is a recipe for major burnout. So we have to balance something. We have to get something stabilized, right? And the first habit that I talked through with people is, you literally have to draw two circles and you have to, in one circle, write everything you have control over. And then the other circle, write everything you don’t have. Just this exercise reminds you that you are not in charge of world wars, you are not in charge of terrorism, you are not in charge of pandemics, like all this kind of stuff. And just naming it sometimes is really helpful.

What are you in charge of? Well, you are in charge of your own persistence. You are in charge of are you kind to, people are in charge of what you eat, how much you sleep, you know, tangible things like that too. But conceptually, I think it’s important to remember, you are in charge of the way you show up to a room. So that even is stabilizing also outside of work. But when we talk about, you know, the unease, the dis-ease that folks are feeling right now with the world around them, if you’re the calm, stable person that shows up in a meeting, oh my God, you’re valuable to that meeting, you know? And, and what a gift you are to the folks on your team, if you’re able to laugh about something that goes wrong and say, “Well, everybody else see on Monday, we’ll try it again.” You know, we are aching for people who can reassure us right now. And it doesn’t mean blindfolding ourselves. It just means, “All right, let’s get in here tomorrow. Let’s try it again.” And, uh, my notion of stability at work, I think, is trying to get more people in that space of bringing peace and ease to a room, then I think we’re in better shape.

Todd Nienkerk: That’s a really good reminder now it’s becoming very personal. It’s a really good reminder of just how I try to be at work in, in my role. And there are some aspects of that that I’m really good at, and there are some that I’m really bad at. I found that I’m really good at, “Oh, this is like a moment of crisis in the business and we’re going to have to deal with this, and it’s hard, but you know, we’ll get through it.” And I can be very calm and steady and thoughtful in those moments. But when, what tends to get under my skin and makes me not present because I don’t start to get flustered or, you know, stressed or angry, but I do get distracted and I get distracted by really little things. It’s like the big things actually center me, but it’s the little things that kind of spin me out. So even yesterday, there was this, you know, project that we were trying to land for the past year. And then they decided to back out of it on the day we were going to start and we’d already had approval from a committee—and it was a small project, so it wasn’t like a huge deal—but it was still like the principle of the matter. We turned down other stuff reserving this team for you. And now you’re just like, “Oh, nevermind. We’re just not going to do it.” Caring not at all about our good-faith efforts, you know, I’m already getting worked up about it right now.

Jen Dary: I’ll coach you. I got you; I got you.

Todd Nienkerk: And anyway, I’ll cut it short, but the point is that, like, I could not focus on any meetings for the rest of the day because I’m just thinking like, “Oh, I’m going to have words. I’m drafting, you know, the emails in my head and like, and of course, like I sleep on it the next day. It’s like, all right, look, just write a level-headed, but firm note that says, “This is poor form, and we’re not going to work with you in the future as a result of this.” But, I’m just going to spell it out and it’s unemotional and that’s it, and be done with it. But I will admit that, as satisfying as it was, I felt like, “Oh, okay, I’ve closed the book on this. I’m going to walk away.” I found myself going back—and writers are like this, rereading it and relishing it. And so throughout the day, I’ve just cracked open the email and be like, “I’m going to read it again!” Now I’m distracted by how good the email was, how happy I was at writing it, right? So like this tiny thing, this relatively small project has sort of spun me out for a couple of days. And by tomorrow I’ll be fine. It’ll be done, and I’ll move on. But like, have you, like, what is it about big stuff versus small stuff? Like, is that just a thing that we’re all different about? How does that work?

Jen Dary: Well, you know, it’s funny. One of the habits is about working with annoying people, which everybody has someone at work or home, probably all, where you’re like, “This person just annoys me. This is so annoying. Everything you say is so annoying, I hate your face.”

You know, like there’s someone around you where you’re like, “Oh my goodness!” And you know, it’s, I kind of say in the video, like at face value, this habit of working with annoying people either sounds mean or exactly right. Because that’s why I put it in there because I really like taking risks and saying the things that nobody else is going to say.

And I think people are sometimes very annoying, but what I point out in this habit, is that it’s not actually the person, it’s their behavior. So if you can separate that and with your clown show client over there, it’s not actually the human, probably, it’s the behavior. And in that case, it’s trickier, right? Because that’s the behavior of a group or the behavior of a company, which is more complex. So I walk people through an exercise of identifying all that annoying stuff. And then the next part is you have to identify what is that person afraid of, if you had to guess. And then by looking at that, it creates the tiniest little sliver of like, “All right, you are also a human, probably afraid of the investors getting pissed, so you had to make a tough call last minute, you pulled the rug out from under Four Kitchens. You made some enemies, but that was maybe the better bet.” You know what I mean? Like you’re, there’s a little space for that, but of course— 

Todd Nienkerk: Well, geez, Jen, thanks for wedging that empathy, finding that tiniest crack to just jam that in.

Jen Dary: Listen, I’m going to send you flowers! And I’m also going to study the best text message comebacks the next time I do it, because of course we all reread all that shit—text messages, emails—because it reminds us that we have a backbone and we stand up for ourselves. So that’s great. Fully endorsed. 

Todd Nienkerk: Well, Jen, thank you, so, so, so much for your time. It was a pleasure seeing you again; it had been far too long since you and I talked. Always a hoot. So how can people, sign up for your e-course? Where can they reach you? Tell us.

Jen Dary: Yes. All the things. All right. So That’s the URL that Todd will put in the show notes. Do you have show notes? Todd’s got you for the website. And then, you know, I’ve got an Instagram, I’ve got a Twitter, things like that. In terms of the e-course, what you’re going to want to do is go on my website and look at Events. So under Events, it’s the upcoming manager trainings, and also this e-course will be on there. We launch next week. Maybe the podcast will be out before then. 

Todd Nienkerk: It’s already out now. Yay!

Jen Dary: So go buy the course, right this second. Uh, and yeah, I mean also people should just email me, drop me an email. I really love when people just say hi. I’m very good at emojis. So you could just email me something about the most annoying person you work with, and I would send you an emoji back and quick notes. So I just, you know, I feel like I’m super approachable in those ways. And you can just say hi, I love when that happens.

Todd Nienkerk: Well, everybody take her word for it. It’s true. Thank you. Thank you. Thank you, Jen. 

And of course I’d love to hear from you. Yes, you, dear listener. What do you want to learn about the future of content? Feel free to send show ideas, suggestions, or examples of the content you create. You can email me at We’re also on Twitter @FOCpodcast. To learn more about Four Kitchens and how we can help you create, manage and distribute your digital content, please visit And finally, of course, make sure to subscribe to The Future of Content so you don’t miss any new episodes. 

Until next time, keep creating content!