#175 – Jennifer Schumacher on Learning From Agency Mistakes

Transcript

[00:00:19] Nathan Wrigley: Welcome to the Jukebox Podcast from WP Tavern. My name is Nathan Wrigley.

Jukebox is a podcast which is dedicated to all things WordPress, the people, the events, the plugins, the blocks, the themes, and in this case, learning from mistakes in website development agencies.

If you’d like to subscribe to the podcast, you can do that by searching for WP Tavern in your podcast player of choice, or by going to wptavern.com/feed/podcast, and you can copy that URL into most podcast players.

If you have a topic that you’d like us to feature on the podcast, I’m keen to hear from you and hopefully get you, or your idea, featured on the show. Head to wptavern.com/contact/jukebox, and use the form there.

So on the podcast today, we have Jennifer Schumacher.

Jennifer has been working with WordPress and web development for over 15 years. Her journey began with a spark of curiosity in university, building her first WordPress website after a YouTube crash course. Then evolving into freelance gigs, team collaborations, and eventually running a white label agency working alongside other agencies around the world.

Jennifer’s experiences have exposed her to the highs and lows of agency life. Projects that run smoothly, but also cultures that can become toxic, people burning out, and the all too familiar frustration of unbillable hours, and broken processes.

This inspired Jennifer’s lightning talk at WordCamp Europe 2025, where she shared some of the most common, and painful, mistakes she’s seen agencies make, and what can be learned from them.

Jennifer walks us through her path in the WordPress world, and we discuss three real world mistakes agencies make. Web support that drains your soul, the design handoff from hell, and work more, bill less, and smile anyway.

We talk through support, bottlenecks, frustrating design to development handoffs, and the dilemma of over servicing clients without fair compensation.

Jennifer shares her candid perspective on why processes and honest communication matter, not just for the bottom line, but for the mental health and building sustainable teams. She also discusses how transparency, learning from failure, and continually improving processes can improve agency life.

Jennifer’s approach is refreshingly open about both the mistakes and the solutions, aiming to help others avoid repeating them.

If you found yourself frustrated with agency workflows, or are hoping to build a healthier business in the WordPress ecosystem, this episode is for you.

If you’re interested in finding out more, you can find all of the links in the show notes by heading to wptavern.com/podcast, where you’ll find all the other episodes as well.

And so without further delay, I bring you, Jennifer Schumacher.

I am joined on the podcast today by Jennifer Schumacher. Hello, Jennifer.

[00:03:26] Jennifer Schumacher: Hello. Nice to be here.

[00:03:28] Nathan Wrigley: We’re here on Contrib Day. It’s WordCamp Europe 2025. Now, because it’s Contrib Day, that means you haven’t yet done what it is that you are going to do at WordCamp Europe. But you’ve got a presentation, like a lightning talk. So you’ve got 10 minutes to stand on the stage.

The idea is that you are going to be talking about agency, WordPress agencies, how they mess up, I’m going to use that word, and how they can learn from their mistakes.

So before we get into that, just tell us a little bit about you.

[00:03:56] Jennifer Schumacher: I started web development about 15 years ago, maybe a even more even. I was at university, no money, on a freelance platform, and somebody asked me if I could build a website. I checked on YouTube, okay WordPress. I said yes, and then I sold a website. No idea how to do it, honestly. But then YouTube helped me figure things out, and that’s how I started and fell in love with it. No way to turn back.

Went for it, did a couple of freelance gigs and then, you know, joining other team members, joining other people in the freelance world, building like groups, working on stuff together, working on projects. And then it grew, got bigger. We got bigger projects. We built a white label team working for the agencies, collaborating with other agencies. And that’s what I have done over the past years. So that’s a bit of my background.

[00:04:47] Nathan Wrigley: Yeah, that’s perfect. Yeah, that’s great. I think your story sounds like a lot of people’s stories in that they, if you began 15 years ago, the web was still very much discovering what it was going to be. And you drop in and learn as you went along. I think maybe now that’s a little bit more difficult. I think if you drop in these days, it’s maybe more challenging. There’s so much more competition out there and things like that. yeah, your story kind of mimics mine except that you grew an agency and I didn’t, I just stuck as a one person, and that kind of worked out for me.

[00:05:15] Jennifer Schumacher: Yeah, it’s like the people network, right? You meet different people and then you get to know each other, and then you start learning, and then you think about the opportunities. And then either you say, okay, this is a path that I want to take, or you don’t, right?

[00:05:27] Nathan Wrigley: And have you ever worked for other people in website building? Have you worked for other agencies, or been an employee? Or has it always been you and the agencies that you have run?

[00:05:36] Jennifer Schumacher: I never have been like an employee per se, so it was more like a contractor, but either freelance or for the agency that we built. But the nice thing, and why I really loved this was it was in different roles, right? Sometimes I was the designer in the beginning, or I was the developer. Later on I did develop myself, but that was in the WP Bakery days. So I don’t do that anymore to be honest.

Yeah, so it was design then more development. And then later on I moved more into project management. And then in the most recent years, there’s so many things that I, after all those years, you know, it’s nice, I love WordPress, but certain things make me sick. I was like, God, no, I don’t want this anymore.

Certain stress levels that I’ve reached where I said, no, I don’t want to do it the same old way as usual. This is something that my talk will be about, to be honest.

And the last couple of years have been more about process improvement. Doing things faster, less stress, and then also all these unbillable hours that many people just hide below the table. So this has been my focus for the last couple of years.

[00:06:41] Nathan Wrigley: Okay. Well, I’ve got to say it’s very, very nice to meet somebody who’s really open and honest about their successes, but also things that they consider they could do better. Let’s use the word failures. I think most people kind of hide that stuff, but it’s really interesting that you are doing a presentation where you are raising that as, okay, I messed this up, I messed this up, I messed this up, and here’s how I took it as a, you say learning opportunity, which I suppose is the best way to parse any of those kind of things.

Why are you doing a talk though at WordCamp? So this is kind of a more of a community question. It’s not really about the presentation itself. I’m just curious as to why, what is it that you get out of it? Do you just enjoy sort of hanging out at these events or, why have you decided to do it?

[00:07:20] Jennifer Schumacher: How can I explain that in the best possible way? I’ve met many great people over the years, but I’ve seen many of them who got frustrated about certain things in part of the culture at the agency they worked at. I’ve seen toxic cultures as well. I’ve seen many projects that started off very nice and then it became frustrating over the time. And then towards the end, people were not getting paid according to what they actually delivered.

I’ve seen people that later on actually quit and they said again, I don’t want to do it anymore. That they were so frustrated, especially in project management, I’ve seen a couple of them just drop out. It’s like, you know what? Not doing it anymore. And I don’t think that that’s worth it.

If we don’t talk about what goes wrong, if we don’t acknowledge about stuff, these things that could be better, and then say, hey, you know what, let’s figure out a better path and resolve this kind of stress because we deserve a better team that’s in sync, then what are we doing? If we just continue and say, well, that’s agency life, you know? That’s how it is in agencies. No, it’s not supposed to be that way.

If you just accept it and just go with it, then it’s going to be that way. I think it’s worth sharing that, because if you don’t ask the question, how can it be better? You’re not making anything better to be honest.

[00:08:38] Nathan Wrigley: Okay. Thank you. So let’s hope that the wisdom that you impart will land with the people. But you’ve got this idea of three real world agency mistakes. That’s what you’re going to focus on in your 10 minutes.

I have a question around that. So obviously you’re going to highlight the things that went wrong, explain how you tackled it. Do you ever get the sense though that there’s ever, and I’m doing air quotes, a perfect system? Have you ever landed on something where you think, okay, that’s it, I do not need to improve that thing anymore? Or is there always room for improvement?

[00:09:09] Jennifer Schumacher: Well, that’s a good question to be honest. I’m German. Many Germans try to be perfect to be honest. But I don’t think perfect exists, and isn’t imperfect perfect. Because the thing is like, learning is a journey, so if we set up a system and then we figure out, okay, let’s try that way, and then we work with it and then see, what can we tweak, what can we improve? And isn’t that what makes it perfect, right? Because we keep improving things.

There are new things coming out now, you know, AI is everywhere. So, are there certain things that we can use that help our system? We just keep tweaking it. So, no, perfect system. Do I want one? No. Is it fun to keep tweaking things? Yes. So I think you’re just trying to get started, build a certain setup and try to improve it over time.

[00:09:58] Nathan Wrigley: Yeah. So that would’ve been the way I would’ve paraphrased it as well. You kind of get something which feels like it’s good for now and then the technology changes, WordPress adapts and you have to figure it out a new. Okay, that’s great.

So there are three things that you’re going to tackle. Maybe you could’ve done 5, 10, but the time was probably the limitation. What are the three things that you are going to mention? What are the three things which agencies make as mistakes that you have encountered?

[00:10:21] Jennifer Schumacher: First of all, I had to think a lot about, okay, which kind of situations do I want to include, right? Because over the years, you know, you collect a lot of stories, and I think the most impactful is a story. You want to talk about a specific situation where you were in. And so I was thinking about, what should I cover?

For each story I made a nice headline. I can just quickly share those headlines, and then you think about what you think that that means.

[00:10:46] Nathan Wrigley: Perfect.

[00:10:47] Jennifer Schumacher: So the first one is, support that drains your soul. The second one is, the design handoff from hell. The third one is, work more, build less and smile anyway.

[00:10:59] Nathan Wrigley: Let’s go back to the first one then. You’re going to have to say the exact wording, because I’ll probably get it wrong. What was number one again?

[00:11:04] Jennifer Schumacher: It’s web support that drains your soul.

[00:11:07] Nathan Wrigley: Okay, tell us, what went on here? What calamity befell you and your agency that led to that portion?

[00:11:13] Jennifer Schumacher: I’ve seen it in many, many agencies and if, for example, once I had a agency in Switzerland and they said, we manage one point of contact for our clients. So this was mainly the project manager, right? So whenever the client wanted something, they contacted this person.

Why was that not a good idea? Because pretty often the people that I met were just simply overworked, especially when it came to support staff. Because the client got in touch with them, they got in touch with the designer. The designer got in touch with them. They got back to the client and they were just in the middle on every little item.

And the more you have of this kind of support work, the stressier it gets. And this is something where I’ve seen a lot of things go wrong and where I’ve seen a lot of frustration just for being the person in the middle.

[00:11:58] Nathan Wrigley: That was something which was commonly, I want to use the word taught. People often told me it would be better to always deal with this one person, because that one person at least is this single point of contact. You can build up a relationship with them. Just prize that open a little bit. Has that led to problems, and what were those kind of problems? Was it that that person, I don’t know, maybe they are not a good communicator or something like that?

[00:12:21] Jennifer Schumacher: Well, the thing is, that person doesn’t, it’s just a person most of the time that communicates. This person’s never resolving the issue. So for example, the client has something super simple, I want to change the position of that button. So the client asks their single point of contact. The single point of contact, they go to the developer, hey, they want to change that button. But then the developer goes back, but yeah, but this position we cannot do, it’s not recommended.

It’s like ping pong. And let’s say changing that button takes like maybe just 30 minutes, but the entire communication about where the button should go and why not there, why it would be more recommendable to go into that spot exactly, or which size or animation they want. These kind of details take maybe two and a half hours. But now the client doesn’t really want to pay for the communication about it.

And then in the end, I’ve seen many, many agencies, they just put this under the table, under the rug, or they say it and then just don’t admit it. And if you have a lot of these support items, you have a lot of unbillable hours. And is that sustainable? No. Is that frustrating? Yes. Especially if you’re a small team and you need to bill for the time. If you’re not able to bill for it, then what are we doing here?

[00:13:31] Nathan Wrigley: So this is the idea then that in a company, let’s say that you as a freelancer are working with a company, I don’t know, maybe they’ve got a hundred employees or something like that. You’ve set it up so that you only speak with this one person in their company. But those other 99 people are funneling all of their bits and pieces through that one person.

You just get this backwards and forwards. That one person becomes a bottleneck because they’ve got to communicate with the 99 people. Any change has to go through them.

Okay, what was the second one? I’ve forgotten, I’m sorry.

[00:13:57] Jennifer Schumacher: The design handoff from hell.

[00:13:59] Nathan Wrigley: Okay, what’s that?

[00:14:00] Jennifer Schumacher: Have you ever worked, like you’re a developer and then you are working on a project where they say, okay, the design will be done by a design agency or by some other designer. And then you get the design, you’re like, well, that doesn’t fit anymore what I thought I would spend on time in the beginning. And then I get a file, it was not even clear like this page, what should be the H1?

And then inconsistent styles. And then suddenly on the mobile view, if the designer also did a mobile view, the designs do not match at all. Like, on this screen they use this size, on this screen, this size. Super inconsistent. And this is so frustrating. Because as a developer, in theory, then suddenly you have so many hours.

Then, again, you have to decide, do I log them? Do I tell them that this is not anymore a fit? And if I am not anymore making it a fit, do I look bad? And again, unbillable hours. And then either you bill them or you’re like hiding them. I don’t like that.

[00:14:57] Nathan Wrigley: This is the idea of if you are, I guess if you’re in a big agency where you’ve got a design team, and the design team is literally in the, you know, the cubicle next to you. That’s a fairly easy point to solve because you just stand up and have a chat about it. But if you’re a freelancer, or you’re dealing with a third party design agency or something like that, it’s a real bottleneck, isn’t it?

Because you get a design, it looks great, but suddenly you realise, well, yeah, it looks great, it would make a great magazine piece. Transferring that over to the web with H1s and paragraphs, and it’s got to be accessible and color contrast has got to be good and all of this kind of stuff, that suddenly becomes problematic.

And usually the client doesn’t have that same level of expertise. So you know, they might catch sight of that design and think, perfect, do that. Do exactly what we see and then you have to have this whole tennis again of explaining, well, actually we can’t do it quite like that. So, okay, that’s the second one.

[00:15:50] Jennifer Schumacher: What I can tell you is that I’ve seen this happen nonetheless in big agencies too. I have worked also with agencies with more than 150 employees. And it always depends a lot on their internal processes and how they approve and the system, right?

Nonetheless, I’ve seen also like big design agencies, and it looked all fancy, but then it did not match up. Maybe you’re very good at selling, but if you internally do not have certain systems in place, this stuff can still happen.

[00:16:21] Nathan Wrigley: Yeah. And I also feel that when I was doing this kind of work, when I was a freelancer, I had to be all the things. I had to be literally everybody. I had to be the designer, I had to be the developer, I had to be the communicator, I had to be the marketer, I had to be the SEO. I had to be all of these things. And with the best will in the world, I’m not the best at all of those things. Probably one or two things I’m pretty good at, but the rest of them fairly lousy.

And so that kind of fits in as well. And again, the process, getting a process exactly right. You are all about sort of saving money by having a process, saving time and money by having a process, yeah.

[00:16:54] Jennifer Schumacher: To be honest, in my opinion, it’s mental health. Because if it goes on for too long that you’re charging less than what you are actually bringing to the table, that’s frustration. You bring that frustration to your home, that’s when you get stressed out. You share with your family what happened. You are like unloading the stress. You are not that much capable of being a good listener if you’re stressed. And you want to be a good listener with the people that you love. So, what are we doing here? You know?

[00:17:23] Nathan Wrigley: You also become like a double fronted marketplace a little bit. Because you’ve got the designer over here who’s giving you designs and you are sat in the middle. And then you’ve got the client over here and you are sat in the middle. And you become this person that has to communicate the ideas in both directions.

And when they say, we want this, you have to communicate that back to the designer. Do you have like a trusted designer or a design, like a network or a team or something like that, that you just more or less rely on that because you’ve figured out they know what I am typically going to want?

[00:17:52] Jennifer Schumacher: I give them guidance how I want it. Some have, you know, worked with me before, here and there, and then they already know. But I tell them exactly how we need things, and then I point things out, okay, hey, like a checklist. Okay, we need to check this, this, this, this, this. And this sometimes could take a lot of time too, depending on the people that, you know, I work with.

But it’s not that I have like a hundred percent go-to person per se. No. Maybe I can share that same thing. I did design many years ago, then development. And sometimes I need to also, you know, pause and say like, Jenny, no, don’t jump in and just do it yourself. You know, I could, but I just should not. So I just try to, let’s say, express how I need things to be done before going into development. If that’s not done, we’re not going into development.

[00:18:41] Nathan Wrigley: I think designing for the web is really difficult because it is a real skill in and of itself. You know, if you’re designing for a magazine layout, I mean, obviously there’s a high level of skill required to do that in an effective way. But then being able to actually understand the semantics of that design, and how it might look, and especially now where we’re going into a web which is not three view ports. It’s not just mobile, it’s not just tablet, and it’s not just desktop.

It’s this much more kind of, we have no idea what you’re going to be viewing it on. We don’t know the width. I think this sort of Intrinsic Design, which people keep talking about, that makes the job even more difficult, okay. So there’s number two.

Number three, what was that one?

[00:19:23] Jennifer Schumacher: Number three was, work more, bill less and smile anyway.

[00:19:27] Nathan Wrigley: Okay, go on. Did you say work more, bill less?

[00:19:30] Jennifer Schumacher: Yeah. Work more, bill less.

[00:19:32] Nathan Wrigley: That seems counterintuitive.

[00:19:33] Jennifer Schumacher: Yeah.

[00:19:33] Nathan Wrigley: Most people would say work less, bill more.

[00:19:36] Jennifer Schumacher: Well, everybody likes to say that, which is unfortunately, the truth is not always how it works, right? So, how about this? Have you ever been on a project where time goes by in the beginning, everybody’s excited? All fits, looks good. We’re progressing and then the client comes back with feedback and then there’s a change. Maybe it’s a change request, you know, okay, we add some extra hours.

But then there’s something that either we did not notice, for example, oh, this doesn’t work in the Safari. And suddenly we need to work a bit more to make it a fix. But the budget is really tight. Anyway, we need to fix this. Or the client wants something, oh, but this should also animate. You animated this, but also this needs to be animated.

Details. Detail here, a detail there. And then suddenly you notice like, well, the budget we had is not anymore available, but the client is still asking for things, and even saying stuff like, that should be included. How could you charge that extra? Or it was not communicated early enough like, hey, you know what, client, our budget is getting tight. If you are requesting more things, we will need to invoice you extra down the road.

Of course you want to say, okay, if there’s something wrong with our work, we will cover this internally. You don’t want to be somebody who says, okay, I did a mistake, but I’m not correcting it, haha. But if the client is requesting more stuff, you need to let them know in advance. Because if you let them know later, they also go like, huh? Where does that come from? Why didn’t you tell me that this has got more expensive?

And then suddenly you cannot charge them for that. And now you worked more, but you are effectively billing less if you take your effective hourly rate, what you actually delivered and work.

I’ve met agencies, freelancers, when they would really calculate their effective hourly rate, they would be crying, sitting in the corner of the room and crying. This is frustrating, right? And nobody likes that. But anyway, they expect you to sit there smiling and just pretend like everything was good.

[00:21:33] Nathan Wrigley: Do you always do that with your clients though? Do you have that approach of, we must smile through this, even though things are not necessarily working out? Because that was one of the things that you wrote in your description. Let me just find it. You wrote, it’s about laughing, learning, and maybe even recognising a situation you’ve been in yourself.

So do you try to have that sort of humorous approach when things are not working out? Can you always laugh? Because sometimes these things can be so profoundly, well, annoying, let’s go with that. It’s difficult to laugh, I think.

[00:22:01] Jennifer Schumacher: I think it depends a lot on your personality. I can tell you something. So I live in Spain and in Mexico. I’m German, but I don’t live anymore in Germany. But I think when you meet different cultures and see how they react, how they treat certain situations, that made me open up my eyes and see like, okay, you know, you always have the choice. How do you react to this? This is your choice.

And if you get frustrated and you dwell into the pain and just continue again and again, and in the same cycle, then that’s your choice. What’s the other end, right? You can just say, hey, you know what? It was a mistake or this happened. I’m not happy about it, but the only thing I can do is appreciate that it happened because it gave me the opportunity now to learn from it. And that’s the super different perspective.

Some people are not capable of thinking like that, but I prefer to think like that, because it makes me feel better and it makes me look at possible solutions and focus on that. Instead of me looking at the situation, focusing on the issue and the problems.

[00:23:07] Nathan Wrigley: I think it’s very difficult in the moment sometimes to be so, I’m going to use the word sanguine. Just to be so measured about it because you know, something doesn’t work out. Maybe the first reaction is a buildup of anger or something like that. But to have that, to be able to in your head, parse that and say, you know what? The anger probably won’t get me anywhere, but viewing that as a learning opportunity.

Because you go into pains, that’s what you say over and over again. Treat it as a learning opportunity. It’s almost like Zen Buddhism, or something like that, you know, it’s kind of trying to turn a bad situation into a good situation.

But you are also at pains to say, well, it feels like you’re at pains to say, just don’t keep repeating it though. You know, if something bad happened, learn from it, but then adapt the process. Make the process different so that it doesn’t happen a second or a third time because, well, that’s crazy making.

[00:23:57] Jennifer Schumacher: Yeah. But that’s, again, the reason why I think I really love the opportunity to be here and to be having that speech at WordCamp. Because, I get frustrated just thinking about it, I’ve seen so many great people just do the same thing over and over again, because they think that’s it and that’s how it is in agencies. It doesn’t matter if they work at this agency or that agency.

Maybe some do it a bit different here or there, but the same problems come up and they do not really think about, how can I resolve this? New project. Like, new projects will fix it, or let’s sell more. Let’s fix it in the next project. Let’s fix it in the next project.

But then they don’t think about a fix. And I have a couple of people who I really think like, God, you’re so good at what you do, but why do you do this to yourself? Why don’t you think about how to get out of this mess? And I think that’s what I want to do, what I want to share because you have to focus on how to solve this. Otherwise, if you don’t make it a priority, you’re stuck where you are.

[00:24:50] Nathan Wrigley: I guess also, each one of us really genuinely does have, so I’m focusing on a freelancer at the minute, you know, so you’re not in an agency, it’s just you. We all really genuinely do have a unique set of attributes which make us the way we are. And it may be that you just have to lean into those. You’re good at this thing, you’re not so good at that thing, so maybe that gets outsourced, or maybe you just have to approach it in a different way. But it’s very, very hard.

I also think that over the last 10 years, we’ve lived through a cycle of YouTube videos where people are trying to pitch us the perfect solution. In 10 minutes I’ll teach you how to revolutionise your agency. Some of that works, I’m sure, but there seems to be quite a bit of snake oil there as well.

And what i’m trying to say is, just because it’s in a YouTube video or somebody is shouting from the rooftops that they’ve got the answer, it may be that that answer actually won’t work for you because that’s not who you are.

[00:25:43] Jennifer Schumacher: Yeah. Well, that can be too. The thing is like, if you see those fancy videos on YouTube with these nice titles, they put them because that gives them a better click rate because people are more like, okay, well, I want to see if I just say like I have something that’s way high work. If you think that that’s a good idea or not, that’s up to you. It’s not a big selling point, right?

So they write it that way just because of the enticing title makes you click. So that’s also, you know, it’s your human brain that follows this kind of direction. Yeah, so I think a big part, just as you mentioned, resources, YouTube. For me, the biggest part has been asking. And that’s why I loved, we started white labeling, working with other agencies, I learned so much from them. So much.

And just sharing, I have one CEO that I once asked, he had built an agency with over two hundred employees, and they started out as four many years ago. I asked him for lunch. I asked, I would love to know how you did it. What was your motivator? How did you decide who to hire? How did you find the right people? What were the big decisions or risks that you took.

And I think that is so important. Why not? What do we have to lose? I think, why not open up conversations and just ask, how are you approaching this? And I think this kind of stuff gets lost a lot. It’s not just only just sitting there and looking at YouTube videos. Who else could I ask? How do you deal with this?

[00:27:12] Nathan Wrigley: I have a question, which is maybe one that you don’t want to answer because it’s quite vulnerable. But what is your biggest mistake? What’s the thing that if you look back over your career you think, oh boy, that was a calamity?

[00:27:23] Jennifer Schumacher: I have one and I think I’m not, well, it is embarrassing. Yes, it is. But why not? It’s like a learning opportunity, right?

So when I was younger, oh God, I don’t know how many years ago, it was like 10 years maybe. So I thought, okay, I want to build a team, I want to do this. Let’s make it at an agency. We have clients, we have projects, okay, cool.

So I searched for people. I got an office and we were all there. And I thought, okay, I also want to be great with our culture because I think, you know, the team is what matters because only if the team is happy, we can make great work. I wasn’t going to be the one that’s sitting there with a whip, you know, like, do this, do this, do this. That was not how I envisioned myself.

But I focused so much on this team that I did not notice that I did not yet learn enough how to be a good salesman. Few months later, I ran out of money.

And because I was not yet intelligent enough about putting up boundaries that certain clients were like, oh, what? That should be included. Why was that not covered? And we just went in and covered it and not communicate, okay, that we stopped covering certain things for free. We did not yet know how to charge certain things on time.

So we were still like, or I was still, did not resolve it. I did not think about, how do I need to do it so I don’t get myself in the situation that I would have a hard time getting out of, especially financially? And then I had to say, okay, that’s it. Pack my bags. I then started a job in sales. And then I had to learn, damn, how do I sell? How do I communicate? And that I did for a year and a half. And when, again, made more money outside of the job, I did quit.

[00:29:06] Nathan Wrigley: Okay, so that was a real learning opportunity, wasn’t it? You went, the whole thing collapsed but the key bit that was missing was sales. You pick yourself up, got a sales job, learnt the sales portion, and then kind of began again. I guess it worked out the next time.

[00:29:18] Jennifer Schumacher: Yeah. This time, we’re still here.

[00:29:20] Nathan Wrigley: That was the low point. That was the thing which you did worst. Maybe you’ll be good at answering this question. Some people are a bit shy when you ask a question like this. What’s the thing that you think you’ve done best?

[00:29:29] Jennifer Schumacher: Oh. What? The best.

[00:29:30] Nathan Wrigley: Yeah. What’s the bit that if you look back over your 15 years, I mean, it may not be exactly one thing, but can you summon up something which you think, actually, do you know what? I’m really proud of me for that.

[00:29:41] Jennifer Schumacher: I’m really proud of me for opening up and saying like, you know what, that’s not how it has to be. I don’t want this anymore. I want to see how I can improve this. I must say that my husband has been a bit of an inspiration here too. He’s the kind of person that’s like, ah, I want to work less. Like, I don’t want to work that much. And he finds a way to do it. He always does. He always finds his way around. It’s like, how come that he figures that out and I don’t? And I’m like, sitting here stressed.

And there was also this thought like, do I like this stress? Do you know these people who are addicted to this kind of stress? And they just think they need it. It’s like, do you really think you need it? Do you really think that that’s what you want? Yeah, this is what made me think. And I’m happy that decision, saying like, you know, no. I don’t want that anymore.

And i’m still having things to learn. You know, there’s still things that I’m working on. Totally. I think having that in your, like a little angel, I don’t know, or figure in the back of your head saying like, you shouldn’t do that. Can this be better? Think about it. That’s what I’m proud of.

[00:30:47] Nathan Wrigley: Being honest with yourself, even if that means some uncomfortable realisations.

[00:30:51] Jennifer Schumacher: Oh God, yeah. Tell me. Admitting to yourself like, damn.

[00:30:56] Nathan Wrigley: Yeah. Yeah. I know what you mean. We often have a culture of, okay, just work harder. Just keep going. Just keep doing the same thing because I’m pretty sure the process over there is bulletproof. Just keep going, and maybe being a bit more open with yourself and trying to learn from the mistakes.

[00:31:12] Jennifer Schumacher: And I think when you see somebody, it’s not cheating the system, but it’s kind of like doing it faster and being more relaxed and even having time to do some extra stuff, and you’re like, I want that. Why am I not striving for that? Why the hell I’m just focusing on being more busy? I think you start doubting things.

[00:31:31] Nathan Wrigley: Yeah, that’s interesting. There’s always somebody in my life who seems to have way more free time than I do. There has to be a reason for that. And probably that they’ve just figured it out and allowed themselves the time off.

And I always found that curious. I would find myself sitting at the desk doing the busy work, just because it felt like I needed to be shackled to the desk because that was where work took place. But really, I probably would’ve been way more productive if I’d gone for a walk for half an hour or just did something a little bit more for me, and then come back, regroup, start again. I never did learn that.

[00:32:05] Jennifer Schumacher: Isn’t that, like it sounds so weird, but isn’t that kind of the expectation of society that you should be sitting there on that desk. How come you’re just going for a walk? How come you’re just saying, you know what, I’ll just get my hair done. Let’s just relax a bit and then I get back with a clear mind to that issue. Why not? But no, society expects you to be available, to be at the desk. That’s how you look good.

[00:32:29] Nathan Wrigley: And it’s curious, we’re in such a fortunate position. I mean, obviously if you work in an agency and they provide you with a desk and you have to be there from nine to five, you’ve got that. But there’s a lot of people in our industry who don’t. You know, they’re working out of a spare room in the house. Maybe they’re doing it out the kitchen or what have you. And you can, you genuinely can, take time off and do other things and work a little bit later because you gave up some time during the day. You can be flexible. I think that’s one of the most remarkable things about the industry that we’re in. It’s utterly brilliant.

[00:32:57] Jennifer Schumacher: I read the other day on my phone an article, it was about a bank where they were saying like the four day work week. And they were saying like, now that AI is around the corner, it’s a no brainer. That’s going to happen. Because we will be able to get more efficient with how we do things. And I think, isn’t that beautiful to more focus on outcomes instead of like the nine to five.

Well, depends also how you manage the agency and everything. And I’ve seen many, they said they want to call their employees back. For example, in Mexico, like I live partially there. Many, many people got called back. But others in Germany I’ve seen, they still keep a hybrid model. Some days they just say, okay, we do a day here, a day there. But many developers said like, nope, staying at home.

[00:33:42] Nathan Wrigley: So people listening to this podcast, hopefully some of them will think, do you know what? It’d be really interesting to chat this through with Jennifer. You know, she seems like she’s got some interesting ideas around that. Do you have a little community of people that you vent your anger, vent your frustration with? Do you have a little clique of people where you share the ideas that you’ve been discussing today?

[00:34:01] Jennifer Schumacher: Besides my husband.

[00:34:02] Nathan Wrigley: Yeah, how do you keep yourself sane? Yeah.

[00:34:04] Jennifer Schumacher: I do not yet have a big community, but I am working on this. Because I think it’s great just to share. I was in this mess, in this chaos until I realised, like I had this awakening moment for more like 10 years. So 10 years, I kind of would, was like lying to myself, I feel.

So I would love to share more. I want to do a LinkedIn live show. So I’m preparing that kind of stuff just to share, like we do, like a bit of talking. How did you do that? And just this story. I have a great network of people that I’ve met over the years with great stories.

And this is something that I want to share. I also wrote a book for freelancers, where I just share the exact same thing because damn, I wish I would’ve noticed certain things earlier, to be honest. Because 10 years is quite a lot, you know? And especially when you start out and you’re freelancing, oh God, I just charge way less. I just shouldn’t think about it.

But you know, I didn’t even know how much I was worth. I didn’t even know how to protect myself so that certain situations I could say ahead of time, you know what? That’s it. This entire project management mindset, or building the system, it didn’t occur to me for so long. I just thought, no, let me put this in a book and then, why not?

[00:35:21] Nathan Wrigley: So, where do we find the book? Or where’s the best place to find you, which then might link to the book?

[00:35:26] Jennifer Schumacher: On LinkedIn. And just, first of all, my network, I just want to get some feedback and then improve it. And then let’s see what else I can put in it. I also can share you something, maybe that’s something you found interesting. There’s this writer, Ryan Holiday. He has a great, great book that’s just called Growth Hacker Marketing. Read it. I love it. And I love the way how he writes this book because it’s so honest. It’s so transparent.

And I wrote it the same way he did. I took my entire inspiration, how I wrote it, based on his book. And I also have a couple of stories that I share at the end of the book from other people out of my network. How they did resolve, for example, the cash flow issue, right? How they approached the entire setup. Where how they even were able to sell their agency. You know, like build it and sell it.

That’s what I mean, ask others. Ask others how they did it. And then not getting stuck on these fancy YouTube videos for people that say they have the solution. But I think it’s so much worth it just to have conversations and learn and listen.

Maybe you do not have to take everything that people say, but maybe just can take a bit here or there and then build your own. That’s what I like.

[00:36:34] Nathan Wrigley: Perfect. Jennifer Schumacher, thank you so much for chatting to me today.

[00:36:38] Jennifer Schumacher: It was a pleasure to be here, to be honest. Thank you.

On the podcast today we have Jennifer Schumacher.

Jennifer has been working with WordPress and web development for over 15 years. Her journey began with a spark of curiosity in university, building her first WordPress website after a YouTube crash-course, then evolving into freelance gigs, team collaborations, and eventually running a white label agency working alongside other agencies around the world.

Jennifer’s experiences have exposed her to the highs and lows of agency life, projects that run smoothly, but also cultures that can become toxic, people burning out, and the all-too-familiar frustration of unbillable hours and broken processes. This inspired Jennifer’s lightning talk at WordCamp Europe 2025, where she shared some of the most common (and painful) mistakes she’s seen agencies make, and what can be learned from them.

Jennifer walks us through her path in the WordPress world, and we discuss three real-world mistakes agencies make: “web support that drains your soul,” “the design handoff from hell,” and “work more, bill less and smile anyway.”

We talk through support bottlenecks, frustrating design-to-development handoffs, and the dilemma of over-servicing clients without fair compensation. Jennifer shares her candid perspective on why processes and honest communication matter, not just for the bottom line, but for mental health and building sustainable teams.

She also discusses how transparency, learning from failure, and continually improving processes can improve agency life. Jennifer’s approach is refreshingly open about both the mistakes and the solutions, aiming to help others avoid repeating them.

If you’ve found yourself frustrated with agency workflows, or are hoping to build a healthier business in the WordPress ecosystem, this episode is for you.

Useful links

Jennifer’s presentation at WordCamp Europe 2025: 3 WordPress Agency F*ckups and What I Learned from Them

The presentation on WordPress.tv

Growth Hacker Marketing book by Ryan Holiday