Putting a price on creativity is never an easy task. How much is an idea worth? And how do you price creative work when the time spent producing it tells you so little about the knowledge, experience, and process behind it?
I had encountered questions like these in my own work, which was what first drew me to Blair Enns. As I read his books, I became interested not only in his ideas about selling creativity and expertise, but also in the path that had led him to those ideas and how his own thinking had changed over time.
As Blair told me in the interview, his path began with a very practical problem: how to sell creativity without giving it away. From there, his work developed into a much broader exploration of creativity, expertise, selling, pricing, and value. And that’s where our conversation began.
What first led you to become interested in how creativity is sold? Was there a particular experience or realization that drew you toward this question?
I grew up professionally in ad agencies and design firms. In my very first job, my boss said to me, “You seem fearless; I’m going to put you in charge of sales”, which we called “new business development.” I was initially interested in the challenge of selling creativity because I was handed this responsibility at an age when I didn’t know anything. I knew very little about advertising, and I knew nothing about selling. So, I simply watched how it was done in the advertising agency. I started to mimic what I saw, but I was never comfortable with that.
Fast forward a bunch of years, I wanted to start my own business. I thought, “Well, sales are so broken that I can help other creative professionals get better at selling their creativity without first giving it away for free in a pitch.” So, I built a business around what I called Win Without Pitching.
The business has always been targeted at creative professionals, and it was really about selling creativity. But there were many outside of my target market, such as consultants, HR professionals, financial planners, etc., that also saw relevance in my approach. But these people weren’t selling creativity. They were selling other forms of expertise, either advisory services or some sort of practitioner services. I took the signal from the market and changed the value proposition from selling creativity to selling expertise. Turns out, it wasn’t just selling creativity that was broken. Selling expertise in general was broken.
There’s an interesting relationship here between creativity and expertise. When you say that you initially set out to understand how creativity is sold, what exactly did “selling creativity” mean to you? How did you see the relationship between creativity and expertise?
In the origins of my work, I realized that there were peculiarities of the creative mind that made selling difficult. The first one is that creative people, when they structure a business like a design firm or an ad agency, tend to structure a business that is poorly positioned. It’s too broadly relevant to everybody because when your superpower is solving the problem that you have not previously solved, then you will go in search of problems you have not previously solved. You will shape your business to allow you to do anything for everybody effectively.
Then, I came along at the beginning of my business and said, “No, your personal need for variety is at odds with your business’s need to focus.” When you focus, you stare at the same problems, and you solve the same problems over and over again. You benefit from repetition and start to deepen your expertise.
That was the first challenge that creative people had with selling. They’re poorly positioned, which puts too much pressure on the sales. You’ve got to talk people into why they should hire you when you have innumerable direct competitors, all these generalists, creative professionals, and firms competing against each other. So how do you differentiate yourself?
Well, you get in a room, and you present to them, because creativity also happens to be tied to autonomy, which is when you eschew processes and systems. You reserve the right to think differently, to treat it differently, which you have to do if you want to exercise your creativity. If you’re a generalist, you’re valid to everybody, you’re relevant to everybody, but different to nobody. You will try to get yourself into a presentation because creative people excel in a presentation.
In my first book, The Win Without Pitching Manifesto, I said that they love presenting so much they’re willing to do it for free on the pitch. That is the fundamental problem that I set out to solve. Turns out that the solutions, the model that I developed to help creative people get better at selling, also applied to other forms of expertise. But at its heart, this model really was developed to help the distracted creative professional overcome some of their personal proclivities and get out of the persuasion business.
How did that initial interest eventually develop into your first book, The Win Without Pitching Manifesto? What made you feel the need for a manifesto, and what drove you to make such a strong statement at that point in your career?
If you’re an expert at something, you need to declare your focus, like what’s your discipline and who’s your market. That’s the first step in positioning your business relative to others. But the secondary differentiator is perspective, point of view, or ideology. Simon Sinek, who wrote Start With Why and Leaders Eat Last, has a great line: “Don’t go looking to sell to people who need what you have. Try to sell to people who believe what you believe.”
I think I knew early on that if I was going to be a successful consultant, I needed to have a book. A few years in, I didn’t have a trophy book that would represent me. I had a book that I was selling for $1,000 a copy on my website, but that’s a different story. I needed a book that would go out into the world and not earn me money directly but help build my reputation.
I wrote weekly then, as I do now. I wrote a lot of material and kept wondering about the book. Then, in 2006, I wrote a blog post at the end of the year that said 12 resolutions for the new year. I’m a big fan of manifesto and aphoristic styles of writing, so I thought I would take this kind of grandiose style, almost like Nietzsche or Confucius. So, I would write these 12 proclamations. For example, the first proclamation was, “We will specialize.”
I was quite nervous about this writing style because it’s not the way I’d been writing to that date, but I had always wanted to write something this way. I published it and got feedback for weeks. People said they printed it out and mounted it on their wall. Then I thought, “Okay, so every once in a while, I want to speak in this voice,” because I felt like I was trying to start a revolution. I honestly believed that and still believe it. I felt that this entire industry is broken. How they sell is broken. And everybody is following the same broken playbook.
I wanted to start a revolution, and revolutions have manifestos. So, I turned that blog post into a book, and it’s sold over a hundred thousand copies, and it keeps selling well every year. By that date, it was the most edgy and bold ideas that I had. And it worked pretty well in the same sense. I have a book, so people respect me more and hear me more.
Expertise seems to have been central to your thinking from the beginning. Looking at your own trajectory, when did you begin to see yourself as an expert? And as your own expertise developed, did it change the way you understood what expertise actually is?
I think I felt largely like an expert, even when I started the business, for two reasons. Number one, I’m a male with high testosterone. I’m going to think these grandiose thoughts of myself, regardless of whether they’re true or not (laugh). That’s the chemical advantage.
Number two, I was so convinced that I was operating in a space where everybody was wrong. You know, if you think everybody else is insane, then clearly you’re the insane one. But I had such positive traction from my very first clients. When I put my first work out there and started to get hired, I had my clients try the things that I had been doing in the previous couple of years, and they worked.
Any form of imposter syndrome just evaporated. I knew in my bones that the way everybody was doing it was wrong, and I got validation pretty quickly. I was so lucky to stumble into an industry where there was nobody saying what I was saying. And there were almost no competitors. There was one established competitor that I could find in the beginning of the internet days. Now, I probably meet a dozen a week.
The Manifesto was published more than fifteen years ago. When you wrote it, what did that Blair imagine the next chapter of those ideas, and of your own work, would look like? Looking back now, how different was the path from the one you imagined then?
I can’t say I recall any specific visions that that Blair had about where this business was going. I would say that, looking backwards, it’s all pretty clear, but not exactly a straight line. There have been ups and downs. But I find myself over the last few months saying to those around me that I’m so grateful that I started when I did. And I didn’t stop. It’s just the value of time.
I’ve written about this. It’s like in investing. If you invested for 25 years, in what period did you accumulate most of that value? It’s in the last, most recent period. It’s the same thing with a career. Today, where content marketing is effectively broken or disrupted, it’s very hard to break in and start doing what I’ve been doing for 24 and a half years. I feel very fortunate to still have an audience and to have already built the authority out there.
I think at the time I had a vision of writing more books. I’ve written three. I’ve just finished the fourth, and I’m about to start on the fifth. I write books faster now, and I couldn’t have predicted how long it would take me to write one. It took me years to write a book, but that’s getting quicker.
Without having a very detailed vision, I think you could look at where I am today and where I was 16 years ago when that book was published. You can see, in hindsight, a very logical, relatively straight line. I’ve just kept doing what others have stopped. I’ve seen others around me change their focus, broaden it, switch things, stop writing, take breaks from creating content. I just have not stopped.
You know, I take vacations. I take time off. I’ve had periods when I got COVID. After COVID, I did not read a book for a year; I don’t know why. I just couldn’t bring myself to read anything. Therefore, when I’m not reading, it’s hard to write. When you’re not ingesting stimuli, new ideas, it’s hard to have output. I struggled through a year or two of that. But I’m out the other side now.
I wanted the ideas to go deep into the creative professions. I think they have, and I’m happy with how deep they have gone into my primary market. I would have had some reasonable expectation that they would transcend the initial target market. They’re not going to get dominance in the financial services arena the way I have in the creative services arena. But that’s okay. My passion is with my initial audience, but most of the money is outside it. I’m happy to be working with everybody in my market.
What fascinated me in Pricing Creativity was the challenge of putting a number on something as difficult to quantify as the value of creative work. What led you to become interested in that problem? And as you worked through it, did it change the way you thought about creativity and value themselves?
I had a moment when I realized I did not understand pricing or value. I’m a reader, as most writers are; I endeavored to learn what I did not know. I ordered three or four books on pricing, and I thought, “I’ll just read a few books, and then I’ll know what I need to know.” I soon realized that this is a massive field. It’s as large as the entire field of human judgment and decision-making. I started reading the canon of literature and applying this to my clients.
I was on a walk with a friend of mine who’s in my target market. He understands the firms I serve. He said, “Man, you should write a book on pricing.” and I said, “There are a lot of great books on pricing, the world does not need another book about it.” Then he said, “Your clients aren’t going to read those books.” He was right. They’re not going to read Strategy and Tactics of Pricing – 5th edition (laugh).
That’s when I wrote the book. It took me many years to write it. Then, within two years of it being in print, I realized what I now know about pricing that is not in the book could fill another book. It’s such a massive field.
For me, Pricing Creativity was an eye-opener because I came from design, so I know the struggle of getting clients to understand the value of creative work. Something that might look like a simple change to a client can involve much more work than they realize, and that disconnect inevitably affects how they perceive its value. The book really helped me understand those dynamics. But you made a point about practice being ultimately perfected through trial and error. How has that process worked in your own case? Can you think of moments, either from applying your ideas yourself or seeing others apply them, when you realized something wasn’t working as you expected and had to rethink or refine it?
Oh, yeah. I mean, I think about a lot of the fundamental principles in the book. I’ve thought of some things at the time I wrote the book. It came out in January of 2018, but I worked on it for eight years. At the time of publication, I was convinced that value-based pricing was the preferred pricing model for anybody in the creative professions. I now hold that idea less rigidly.
As I’m fond of saying these days, I care less about how you price, and I care more about whether you have a value conversation or not. If you have a value conversation where you’re endeavoring to uncover the value of what you might do or the value that the client is seeking to create, then you open the door to value-based pricing. But you can still choose to price on other dimensions, which are typically inputs of time, materials, or the outputs.
The market values the outputs or deliverables, so I see the downsides of value-based pricing and why it can be difficult for some people. It’s not a panacea. That’s just one example. Productization of services versus the customization of services. I have gone back and forth on what is the right way for you, the reader, to think about this, especially if you’re a business owner and you can shape the package of your services. Do you keep it loose and open like a loose consulting engagement, or do you package them up into very distinct services with very clear lines to mark those services?
I’ve gone back and forth multiple times on that. Trial and error like this is how all knowledge is created: conjecture and criticism. One would hope that when an author puts something forth in a book, it’s not just conjecture. They have already criticized it intellectually and in the marketplace. I had largely done that. But when you publish a book, you get feedback.
I realize, as one does, some of these things aren’t as important as I thought they were. After eight years, I pulled that book off the market because I had not yet written the second edition, and I started to feel a little bit guilty about what I knew about pricing that was not in that book. Whether it’s in a book format or something else remains to be determined. It will probably be a book, but it might also be a course.
You also do a lot of teaching through your training programs. Has teaching helped you refine your own ideas? Not necessarily because of the feedback you receive, but because having to teach something often forces you to go deeper and can reveal gaps or aspects of your thinking that still need to be developed.
I think if you took the teaching aspect out of my business, my ideas would be less powerful. I know teaching is important, but I realize it’s the capstone of solidifying an idea.
So, let me walk you through my writing process. I commit to writing a post every week. That post gets posted to my website, and it gets emailed to our mailing list. In the other four days of the business week, I write shorter posts on our client portal called Win Without Pitching Academy. That’s where I test ideas. I’m thinking through my fingers. I’ll write four posts in a week. Then, it comes the time for a weekly post. I thought, “Okay, what am I going to write on? I don’t have any big ideas.” I will flip through the little ideas or the little expressions of ideas that I’ve already worked through. I grab one and build on that.
First, it’s a daily post that I’ve written in 10 minutes. I wrote it because I have a larger idea about something I don’t understand. There’s something I like and understand about it, but there’s more that I don’t. I write around 300 words on it. Then, I have to go deeper and write 1,000 to 1,500 words. I grab one of these starter posts and publish it on LinkedIn. If I published something on LinkedIn, I’ve almost certainly already written about it in the Academy. So now I’m getting more public feedback, both from my clients in the Academy and from LinkedIn. Then I publish the bigger post. It goes out to a larger audience. I get more feedback still.
One in four of those posts becomes the subject of a podcast I do with my podcast partner, David C. Baker. We have a podcast that is weekly. Every two weeks, an episode drops, and it alternates between me interviewing David on something he wrote or David interviewing me on something I wrote. One in four of my weekly posts will be promoted to a podcast. I will reread the post, realize what I missed or what I know that I didn’t cover in that post. I’ll talk about it in the podcast. That will further cement the idea.
Then, the next step is when the podcast is out about eight weeks later. I’ll listen to it, and I’ll already have forgotten some of the things that I knew. It’s almost like flashcards where you’re spacing them out further and further, and you’re going back to these core ideas. After I finally listened to that podcast, I now own the idea. It is now a tool in my toolkit.
It’s not until I’m teaching these things to my clients – and I don’t do a lot of the teaching anymore, but I do just enough to keep me teaching – where I start to weave the new things in, even in established curriculum that I’ve had for years. My coaches see me weaving the new things in, and they start doing the same.
All of this builds on each other. You could remove any one of these steps, and it would still work, but it wouldn’t be as powerful. It’s a Richard Feynman thing, right? It’s only when you are able to teach it at a very basic level that you can claim to understand it.
So, you keep revisiting these ideas until they become something more developed or teachable or, as you put it, a tool in your toolkit. You mentioned conversation, and that makes me think about the evolution from The Win Without Pitching Manifesto to The Four Conversations. You started with a set of principles, but over time those ideas developed into a framework that people could actually use. How did that happen? And why did conversation become the organizing idea?
The Four Conversations is our model on which we hang everything that we teach. It all fits into this model. As I quote George Box in the book, a statistician and professor on this topic, “all models are wrong, but some are useful.”
Why four conversations? I don’t know how it evolved that I started to think of the sale as a series of four linear and discrete conversations. I know that’s wrong. When I say it right at the beginning of the book, I’m not claiming that the sale actually happens that way, but I’m saying it can be helpful or useful to think of it that way.
I mean, there are certain conversations in a sale. There’s the qualifying conversation, which is fairly standard where you’re vetting the lead. There’s a closing conversation where you’re sharing a proposal. That’s fairly standard. If you want to open the door to value-based pricing, then you’re going to have a value conversation. So that’s three conversations. Then, I added the idea of a probative conversation to cover everything that happens before the first person-to-person human interaction.
I don’t know how it evolved, but the business is called Win Without Pitching. The first book is called The Win Without Pitching Manifesto. One of the proclamations is to “replace presentations with conversations.” So, a core philosophy of mine is that you’re not in the persuasion business. Quit trying to talk people into things. If you’re a properly positioned expert, you can simply go looking for the next person to help, and you determine if you can help by having a conversation.
I’m fond of saying you can present to people, or you can be present to them; you can’t do both. When you’re in presentation mode, you’re not conversing. You’re sending the signals that you’re not listening or not interested in listening. You’re trying to talk the client into something. Now, if you’re selling expertise, I say the sale is the sample. If you’re trying to sell an engagement where you are the expert advisor, it does not bode well when you show up in the sale, and your first interaction is not listening and not conversing but trying to convince. We don’t want advisors who are trying to convince us of things. We want advisors who will listen to us, ask intelligent questions, help us weigh the pros and cons, the trade-offs, and help us make a decision. Not somebody who’s going to convince us. If that’s what a proper advisory relationship looks like, then that’s what the sale should look like. Therefore, the sale should be a series of conversations.
Maybe the other statements did not become as big as the conversation one, but I had a moment when I realized each of these 12 proclamations could be its own book. There are four that I call the “money proclamations,” so basically, I wrote a book on that called Pricing Creativity. But the first proclamation on specialism, and the second proclamation on “conversations not presentations,” are the foundational ones.
It’s not surprising to me that I’ve gone deep into them, which is addressed in the probative conversation. But maybe I should go back and look at the rest of the proclamations and see if there are more books there (laugh).
That’s interesting, especially because some of those proclamations seem to have taken on a much bigger life than others. It makes me curious about the ideas that took a different path. Are there ideas you’ve developed over the years that you feel never received the attention they deserved, or that you personally find more interesting than the ones you’re best known for?
Probably the idea that I have held closest to my chest, and I have written the least about, is what I call process-framed case studies. We have a training curriculum on it, but it’s aged out, and I’m about to redo the curriculum and do a public workshop on it early next year.
I’ve not seen this idea anywhere else. It seems to me to be quite proprietary to us. It’s the idea that every expert, especially in a crowded market, should have a codified way of working. In fact, that’s a benefit of repetition. I would say to these really well-positioned design firm owners, “Listen, if I get you to dig a ditch, you’re going to do it to X effectiveness and at Y efficiency. But if I get you to dig 50 ditches, the 50th ditch will be better on both dimensions.” It will be a more effective ditch, and you’ll be more efficient. And not only that, but you will also have developed a modified way of digging a ditch. You will have formalized how you assess the ground, how you determine which tool to use, what the shape of the ditch would be, how wide it has to be, etc. And that’s just the benefit of repetition.
If that’s true, then it follows that if you’re an expert in what you do, you have a codified way of doing what you do. So, I think you should codify your model into a visual diagram. In the sale, in the second half of the qualifying conversation, when the client will ask you, “Well, how’s this going to work?”, you should be able to pull out a map, some sort of visual model and say, “Here’s how it works. Here’s how I apply my expertise.”
Every model will roughly follow the same four steps: diagnose, prescribe, apply, reapply. Diagnosis of the problem, prescription of a solution or a therapy, initial application of that therapy, ongoing reapplication as necessary. Everybody will follow that roughly four-step model. In the beginning, when you’re not really an expert but more of a generalist, your model will be generic and indistinguishable from everybody else. But if you narrow your focus a little bit and you add time and repeated application, you will, just like the ditch digger, come up with your own novel way of thinking about this problem. You’ll develop this perspective, point of view, or even ideology that we talked about initially. Your methodology will evolve to be a little bit different and will have something special in it. And if you keep going, you may actually develop protectable intellectual property.
Now, fast forward a few years, your model is really interesting. And you say, “This is how we think about your problems and how we go about bringing a solution to bear.” You walk through these four steps, but there are things in there that are specific to you, that speak to your ideology or your fundamental perspective on these issues. That’s great, but everybody’s got a model or should have a model that they can walk you through. The next thing to do is to take your typical before-and-after case studies, to break them up and to reassemble them in a manner that proves that you actually follow this model. So, at the end of the diagnostic phase, here’s what we found. At the end of the prescription phase, here’s what this prescription looks like.
In a closing conversation, or even before that, when you’re walking the client through your model, they think, “Oh, that’s interesting. But the other firm I talked to also showed me a fancy presentation on their model.” Then you show your case studies where you’re now proving that you actually use this model. And from that, the client will draw an inference: little variability in process equals little variability in outcome. You actually follow this model. I can see it. I can see myself in it. I can see how this is the way that you consistently get high-quality outcomes. So, it’s a way to take control of the sale, to say to the client, “If we work together, here’s how it’s going to work,” and to offer them one of the highest levels of reassurance that I know of that everything is going to be okay.
When it comes to selling expertise, closing is about just reassuring the client that everything is going to be okay. There are a lot of nuances in there that I haven’t covered, but that idea, the ideas around, and the curriculum around process-framed case studies, that might be the most valuable thing I know.
Earlier, you talked about your writing process and how writing helps you develop and refine your ideas. That relationship between writing and thinking becomes particularly interesting with AI. As you’ve started using AI in your own work, what has it taught you about the way you yourself think? Has it changed anything?
It hasn’t taught me anything about how I think, but I absolutely love AI tools. It is a fascinating time to be alive and in business. I would not want to be starting my business right now, though. I mean, it’s so easy to come up with a product, but it’s really hard to find a market and break through the noise while everybody’s spinning up AI products.
We use it for all kinds of things. Internally, I use it for a little bit of marketing writing, but I would not be where I am without the thinking that I’ve done. Writing is the medium that lets me do this thinking. Thinking in public by publishing this writing is how I built this business. The last thing that I’m ever going to do is let AI do my writing and, therefore, think for me. I am quite bemused at the volume of experts out there who are handing writing and critical thinking skills over to AI. It is not going to take long for the world to get stupid.
Looking back at your career and work so far, what questions remain unresolved? Which ones are you still trying to answer, and what keeps you coming back to them?
The question of the day is: if you can’t build your reputation through content marketing, how do you build it? I’m working on that one right now. How do you sell? How do you break through as a human in all this AI slop and automated outreach? Those are related problems.
But there are all kinds of things. There are pricing models that I haven’t fully explored, where I have initial points of view that require more work and more writing, like subscription models. I see the value of subscription models, but at the same time, the world is oversubscribed. There’s no shortage of things for me to write about.
When I started this business, I thought, “I’ll start writing and, in a few years, I’ll learn everything there is to know.” That’s just ridiculous. I’ve just turned 60. If you had told me 25 years ago that at 60, I would not even be contemplating being done, I would have thought, “That doesn’t sound like Blair.” But I’m not even contemplating being done. As long as it’s intellectually interesting, I’ll keep going. I don’t see an end to it being intellectually interesting.
There are some questions that I started back then, before Win Without Pitching and the Manifesto, that are still here, that I still feel that I don’t have the answer to yet. There are different questions. When you solve a problem, what’s the prize? The prize is the ticket to the problem that you created by solving the problem. And so, you keep solving problems. You don’t get to a complete list of all problems solved. That’s just not the way life, curiosity, and creativity work.
Finally, looking beyond where you are today, do you have a sense of where your work might go next? Are there new directions you find yourself drawn toward?
I think you can draw a line from where I was 25 years ago, when I started, to where I am today. The lesson that I’ve learned is that I have just kept going when others have not. From that, you can’t just keep drawing a straight line. There’s always something else to do or to think about. Always. If you can’t see something else, it’s because you’re not solving the problems that are in front of you. Solve the problems in front of you, and the next problem will be revealed. They don’t stop. The problems stop when you stop.
You can learn more about Blair Enns’s work on his website. You can also connect with him via LinkedIn.