Dana says you’re worth it.

Dana says you’re worth it.


Artist Dana Woolman
Michigan, USA

Ann Rea: (00:01)
There it is. We’re live. Okay. So I’ve got bonked on the nose by art.

Dana Woolman: (00:09)
I know. I saw you on Monday. Oh my gosh.

Ann Rea: (00:14)
Stupid stupid frame. Alright, well everyone, my name is Ann Rea. I’m a fine artist. I’m a mentor to artists all over the world, and one of them is Dana, and she is sitting on the planet. Where are you? In Colorado? Where are you? 

Dana Woolman: (00:29)
No, I am in Michigan. You know the mitten? 

Ann Rea: (00:37)
Yes. Because I grew up in Ohio. Not far.

Dana Woolman: (00:41)
Right, right.

Ann Rea: (00:42)
Not far from you. Okay. So everyone, let’s learn a thing or two. Before you joined the program, Dana, what were your top two challenges? What were the– what was like messing you up? 

Dana Woolman: (00:58)
Well, like most of the students here, we’ve been artists forever, and I had some time, I’m retired, partially retired teacher. And so I had some time and I was, you know, making my art, making my art, making my art. And it just kept piling up and piling up and piling up. And so, yeah, so I’m just like, “Hmm, I need to really learn how to sell this.” And so I got an expensive website. 

Ann Rea: (01:30)
Oh, well how did that– was it complicated too? 

Dana Woolman: (01:34)
My gosh, yes. Yes! I watched many YouTube videos trying to learn how to do this. And being a teacher, I like to learn, so I was like, “You know what, I’m going to figure this out no matter what.” But it wasn’t.  

Ann Rea: (01:47)
Did you?

Dana Woolman: (01:48)
For the most part, but it’s not perfect, that’s for sure. And– 

Ann Rea: (01:54)
Yeah, go ahead.

Dana Woolman: (01:56)
And as I learned in the program, I was a little premature with that because I didn’t know my niche. 

Ann Rea: (02:03)
Right. So, hey, everyone listening, the first place to start is not a complicated e-commerce site. Okay. That is the tail wagging of the dog. That is the cart before the horse. Right? You’re going to spend a ton of money and a ton of time, and you’re probably not as patient as Dana, right? 

Dana Woolman: (02:25)

Ann Rea: (02:26)
And so go get yourself an Instagram shop for free to start. Alright. That’s okay. But anyway, so you probably spent a bunch of money, a bunch of time, and all that time you spent, you could have been selling your art. 

Dana Woolman: (02:40)

Ann Rea: (02:41)
Alright. So that was one challenge. 

Dana Woolman: (02:45)
Let’s see, another challenge. Well, you know, I thought I was confident, but as I’m learning with the program, I wasn’t as confident as I thought. I was like having real conversations with people about my art. I was just kind of like I had the mentality of you know, starving artist and I know it’s awful. Yeah. Yeah. So, you know, so I taught for all these years and made fair money. Not great money, but fair. And, you know, I do love teaching, so it is fun. But anyway, yeah, my confidence was not there. 

Ann Rea: (03:25)
Was there like a particular instance that you remember that you were trying to have a conversation and you realized, “Oh damn, my confidence isn’t quite there yet.” Did you have– can you recall an instance?

Dana Woolman: (03:39)
Yes, you know, a couple of instances. I was in an art show, north of me, and just talking to some of, not even the artists, but some of the people who were there. I just didn’t feel confident. And, you know, I didn’t want to talk art speak, I guess. It’s just, it’s really not my thing either doing the gallery thing. It’s just, it makes me feel icky and yeah.

Ann Rea: (04:04)
Yes. How did you feel? So you’re attempting to have a conversation, not probably unsure of how to guide that conversation in a way that felt authentic and confident. Right? 

Dana Woolman: (04:14)

Ann Rea: (04:15)

Dana Woolman: (04:16)
I felt awkward. Awkward. Not confident at all. And like the person was during the headlights. 

Ann Rea: (04:27)
Yeah, right. Because talking about–there’s a famous saying, talking about music is like dancing about architecture. 

Dana Woolman: (03:36)

Ann Rea: (03:37)
So so many artists are so tongue-tied, so confused, so overwhelmed when it comes to having an authentic conversation with a potential collector and they don’t know what to do. They’d rather hide or write a stupid artist statement that just kills any convers any chance of having a real conversation. Okay, so that’s, so that’s– alright. So you were spending a bunch of time, probably money, ’cause time is money on a complicated e-commerce site. It shouldn’t be complicated. You guys really shouldn’t. It should be very easy to use. And you should own the URL. Don’t ever freaking pay anybody. If you don’t own the URL, it means like, you know, you got to have that. So it’s yours. And yeah, don’t do– artist statements just kill conversations. But if you’re working with representatives or galleries, they’re going to ask you to write those nasty things, which are just as difficult to read as they are to write. So you learned some things so far, right? In the program. 

Dana Woolman: (05:39)
I’ve learned a lot. It’s amazing. Yes. 

Ann Rea: (05:42)
Can you–

Dana Woolman: (05:43)
A lot, A lot.

Ann Rea: (05:54)
Good, good, good. That makes me very happy. Can you share like your top two– the top two things you learned? And then I want you to share your top two accomplishments so far. But let’s start with what you learned so we can, because that’s going to speak to your accomplishments. What are the two biggest things you’ve learned so far? Cause you’re–

Dana Woolman: (06:09)
Well, obviously realizing my mission. That was huge. And perfection is the enemy of good. 

Ann Rea: (06:17)
Yes. And the enemy of done. And the enemy of– it kills creativity. It’s awful. But we do it because we are trying to protect ourselves from criticism and rejection, and it doesn’t work. So, how did life change for you as an artist and as a person when you unearthed your mission? What changed? Why does that matter? 

Dana Woolman: (06:44)
Well, it matters because now I can have authentic conversations with my collectors and hopefully new collectors. 

Ann Rea: (06:53)
Yes. Yes.

Dana Woolman: (06:55)
I mean, I slip that baby in wherever, any conversation. Wherever I am, I just slip it in. 

Ann Rea: (07:01)
Yes, yes. Exactly. That’s all you got to do. Then you’ll just be in yourself. It’s not like this is like fake or anything. It’s just, it’s a hundred percent real. Right? 

Dana Woolman: (07:09)
Exactly. Yes. Yes.

Ann Rea: (07:10)
And it’s not just, it’s not just authentic conversations. They’re meaningful conversations. 

Dana Woolman: (07:18)
Right. And it’s so great to make those connections with, you know, people. They have the same, you know, back, well, not background necessarily, but they’ve had some of those instances in their lives too.

Ann Rea: (07:29)
Right. Because as an artist, our jobs are to, well, first of all, let’s back up. What’s our product? We’re not selling goods or services. So if you’re looking at marketing or sales strategies that are designed to sell goods or services, you’re going to be very limited, or they’re going to fail because your real product as an artist is emotion. And your job is to connect people with their humanity, which is what Dana’s doing every time she shares her mission. And then they find a commonality in their human experience. And that is inspiring. And that generates emotion. And it all works really beautifully and seamlessly. And you don’t have to feel pushy and you don’t have to feel weird, or you don’t have to feel awkward like you did before. 

Dana Woolman: (08:16)
Exactly. Yes. It’s amazing. 

Ann Rea: (08:19)

Dana Woolman: (08:20)
While it works. Right?

Ann Rea: (08:56)
Yes, it works. People don’t– they’re like, “Is it going to work? Is it going to work?” Yes, it’s going to work! It works every time. Alright. 

Dana Woolman: (08:27)
Yes. And I love it that I’m not, you know, thinking, “Oh, I’m going to share my mission here or there.” No, you don’t even think about like, “Oh, I’m going to share my mission.” Or I don’t even ask. It’s just like, like I said, part of the conversation. 

Ann Rea: (08:40)
Right. It’s just part of you showing up for the conversation as yourself.

Dana Woolman: (08:44)

Ann Rea: (08:45)
Okay. So one thing you learned was your mission. And then what’s another big thing? I know you learned more than two things, but like what comes in your head is like, “Yes, that made a difference.”

Dana Woolman: (08:55)
Oh gosh. Like I said, the perfectionism.

Ann Rea: (08:59)
Oh, that’s right, you said that. Yes. Okay, so you got–do you feel like you’re a recovering perfectionist now?

Dana Woolman: (09:06)
I am, but I keep going back and forth, you know, a little slippage here and there. But like when I did my Kickstarter letter and I said, “Oh, I don’t know.” You know, and I did that early on and I didn’t, I felt a little icky about it at first, but then I just sat down. I was like, “Just do it. Just do it. And do it scared. And do it feeling icky at first.” But it was authentic and it was, yeah, it was amazing. 

Ann Rea: (09:31)

Dana Woolman: (09:32)
 The results were amazing.

Ann Rea: (09:34)
Excellent! So Kickstarter, before Kickstarter is a strategy that I designed. It’s a proprietary strategy that we teach inside of the program. So we’re not going to go into all the details ’cause there’s a lot of details and steps, but what I would love to know is, what were the results for you, Dana? You did it. You felt scared and you did it anyway. You felt weird and awkward and you did it anyway. And then what happened?

Dana Woolman: (09:59)
Well, I was so close to my SMARTER goal, my first SMARTER goal with some appreciation parties and appreciation letters that I said, “Okay,what do– what can I do now?” You know? And so I looked at the Kickstarter letter and I was like, I said, “I was not far from my SMARTER goal.” And the Kickstarter letter put me above and beyond like so far over.

Ann Rea: (10:23)
Okay. So what Dana’s referring to is every student comes into the program and they establish their first SMARTER goal, which is a–their art sales goal, which is specific, measurable, attainable, results-bound, results oriented, and time-bound. And e and r stand for evaluate and revise if necessary. So, what percentage do you think you surpassed your SMARTER art sales goal? Where do you think you’re at right now?

Dana Woolman: (10:53)
Oh well, I had to revise it. I was way too low. 

Ann Rea: (10:58)
I love that problem. Oh, oopsie.

Dana Woolman: (11:00)
I know.

Ann Rea: (11:01)
Oops. I sold way more art than I thought I was going to. Good! 

Dana Woolman: (11:06)
Yes. I mean, percentages, you know how artists forget the math, but–

Ann Rea: (11:11)
Oh, I have a percentage calculator online. It’s called– and I can’t– ’cause I can’t do it. And I just go to that and do the percentages. 

Dana Woolman: (11:18)
Yes. No, it was amazing. I mean, I thought, “Oh my gosh, now I have to revise my SMARTER goal because I went way above and beyond and so much sooner than I had anticipated. And so now the SMARTER goal that I wrote is, you know, it’s a little bit longer and it’s bigger. 

Ann Rea: (11:36)
\Okay, great! Alright. So if you don’t have an art sales goal, then that is your goal. You have a goal, that’s your goal. You got to have a goal. And just real quick lesson,  I teach this but with a twist. So when I started as a full-time artist, I determined based on prior year sales, I projected what I would do the next year. And so I wrote out a statement, and I wrote out this statement that clarified my SMARTER goal. And also it had a twist. And it was something I learned from Bob Proctor who hosted the movie, “The Secret” and helped Ellen DeGeneres beat Oprah Winfrey. So what I did was, I said, “I am so happy and grateful now that I have sold over $100,000 of my art.” Now what’s really important to pay attention to is like “I am.” “I am.” That statement is a very powerful statement to signal your subconscious mind, and also wrote it as if it already happened. That signals your subconscious mind that it already happened. Here’s what happens. I didn’t know how I was going to do it. That doesn’t matter. That’s not where you start. You start with the goal and then how you’re going to do it starts to come into view. Now, obviously, when you came into your view, it was the strategies we teach inside of the program, right? You did the Kickstarter, right? But let me ask you, if you didn’t have an art sales goal, Dana, and you just came into the program and you learned the strategies and you learned the tactics, but you didn’t have an art sales goal, how do you think it would go for you right now? How do you think you’d be doing? 

Dana Woolman: (13:19)
I think I would be doing well, but not as well because that art sales goal, I mean, that was, I was so close to that first goal. I just had to get it. I mean, I could taste it. So yes, I have to go for it. 

Ann Rea: (13:36)
Yes. Yes. It’s very motivating, isn’t it? And you have to define it correctly, because if you use wishful thinking and you overestimate, it’s no good. If you are to think too small, it’s no good. It has to be attainable, but it should scare you a little bit for sure. Okay. So, that’s awesome. I love that you did that. Alright, now, if you could go back in time and give yourself advice about maybe, even your younger self, version of you that decided that she wanted to be a fine artist and you could travel back in time and your time machine and give her one piece of advice, what would you tell her? 

Dana Woolman: (14:26)
I would tell her, you can make money selling your art and you can make the art that you want to make and make really good money selling your art and take this class.

Ann Rea: (14:39)
So for someone who was sitting on the fence, they weren’t sure about applying, they were like, “Oh, is this some scam? What the hell is this?” I mean, what would you honestly say to somebody who had reservations about applying or investing in themselves? 

Dana Woolman: (14:54)
I would say get off the fence. Spend the money. You’re worth it and you can do it. If I can do it, you can do it. 

Ann Rea: (15:04)
There you go. I didn’t say that you guys, but to give credit where credit is due, Dana did the work and she shows up for class and she’s active in the Facebook group. You get out of things what you put into them. So Dana, I’m very proud of you because you have done that. You got over yourself and you wrote the damn letter anyway, and you got over yourself and you determined your mission and you started sharing it anyway. But I bet at the beginning it was felt awkward and weird. But look at you now. Now you’re comfortable talking to potential collectors. You don’t have any issue.

Dana Woolman: (15:49)
And I’m selling prototype projects all over the place. 

Ann Rea: (15:52)
Yay. Yay. So what Dana’s referring to is the prototype project. So what’s different about Making Art Making Money™ School of Business is this, my students sell their homework and they either sell their art or they don’t sell their art. Either way is fine because if they don’t sell their art for the first time, they’re going to find out why. If they do sell their art, they’re going to find out why. And the more of those prototype projects that they do, the closer they get to determining their niche, which is the keys to the kingdom. It’s the ultimate objective of the program. A lot of artists are confused about what a niche means. Were you confused, Dana? Did you understand what the term meant and how it related to you selling your art? 

Dana Woolman: (16:42)
No, I really didn’t. Not really in the beginning. 

Ann Rea: (16:46)
Yes. Most, most artists don’t. So allow me to explain to those listening. Knowing your niche means that you know four things. But before we go there, let me preface this. Your niche is not about you. It’s not about your art. It’s not about your genre. It’s not about your subject. It’s not about your medium. It’s about this: your niche is knowing who wants to buy your art, why they want to buy it, and where and how to go find more people just like them. If you can’t check all four boxes, sorry, but you’re going to go out of business or you’re going to struggle mightily and you’ll only get art sales here and there. You won’t build up a consistent rhythm if you don’t know your niche. So that’s what Dana’s working out with these prototype projects. And I’m sure, you know, you’re gaining a lot of insight, but let me– I don’t want to put words in your mouth. How are they going? Are you getting that critical feedback that’s helping you?

Dana Woolman: (17:45)
I am. And honestly, I have lots of referrals that I haven’t even gotten to yet. 

Ann Rea: (17:51)
Oh, poor dear.

Dana Woolman: (17:54)
I’m still working on my, you know, the relationships I have right now.

Ann Rea: (17:59)
That is excellent. That’s music to my ears. 

Dana Woolman: (18:03)
It’s amazing.

Ann Rea: (18:05)
That’s Awesome. So what Dana’s referring to is referrals are when someone refers Dana to another potential collector so that Dana doesn’t have to do the work. They’ve done most of the heavy lifting for her. She didn’t have to sell herself. She’s already been sold. Now why is this important? Because when you get referrals, you keep all the money, all of it. And people who are referred to you are 82% more likely to buy from you spend more money and be more loyal. It’s the foundation of all luxury marketing and sales referrals. And if you’re selling art, you need to understand luxury marketing and sales because art is a luxury. And there are some very important distinctions between luxury marketing and sales versus mainstream marketing and sales. So, damn, this is good. I’m so glad here. My referrals! Awesome. I love your problem. Good for you.

Dana Woolman: (19:07)
Yes. Yes, thank you.

Ann Rea: (19:09)
This wasn’t a problem before, so I’m glad it’s a problem now.

Dana Woolman: (19:13)
It wasn’t a problem before and you know, I looked at my list of collectors before I started the program and you always instill the idea of work with what you have. And I thought, “Well, yes. Work where you are and work with what you have now.” Yes. And I thought these people are not going to be buying, you know, the big ticket items. But you know what? I asked them anyway

Ann Rea: (19:37)

Dana Woolman: (19:38)
And they have helped me out. So it’s been amazing.

Ann Rea: (19:41)
Yes. What a lot of artists don’t understand is that you are the best person to sell your art. Because people who care about art, care about the artist. They don’t care about the middleman. They don’t care about the gallery owner. They don’t care about the art representative. They care about the artist, and that’s your advantage. That’s your superpower. All you have to do is make yourself available for a conversation and they will help you. And what my students get to do is blame me if they feel goofy or awkward about doing any of the homework assignments. They can just say, “Oh, this woman named Ann Rea living in San Francisco, she’s making me do this. It’s part of my homework.” I mean, doesn’t– I mean, have you used me as an excuse? I encourage people to do that if they feel awkward. 

Dana Woolman: (20:32)
I have. I have asked people if they will help me with my homework, but I don’t really say, you know, it’s you and I don’t really say you. 

Ann Rea: (20:40)
That’s okay. I don’t care how you do it, Dana. I just care that you get the results. That’s all I care about. And I’m really happy for you, and I’m really proud of you. And I hope that this interview, like 300 other ones I’ve done, shows artists that it absolutely is possible. If you have sold your art already, then it stands– it’s good enough, period, good enough. And if you’ve already sold your art, then it stands to reason that if you had a proven roadmap, and you had an expert mentor, and you had a supportive network to cheer you on. You could be selling more. But if you want to struggle, keep doing what you’re doing.

Dana Woolman: (21:21)
Don’t struggle.

Ann Rea: (21:22)
Don’t. Don’t. I mean it’s so much fun selling art. It’s so inspiring. It’s like getting paid twice. So anyway, thank you so much for your valuable time and attention and for sharing your experience. I really appreciate it. It helps other artists to hear from other artists, and know that, you know, if they’re feeling awkward in their conversations or if they’re struggling with complicated e-commerce sites, you’re not alone and you don’t have to live with it.

Dana Woolman: (21:53)
Exactly. Thank you so much. 

Ann Rea: (21:55)
Alright, take care, Dana.

Dana Woolman : (21:56)
Thank you.

Ann Rea: (21:57)
Thank you. Bye


Side-step 50 common mistakes that most fine artists don't know even know they're making.

Side-step 50 common mistakes that most fine artists don't know even know they're making.

Ann Rea

Ann Rea, Fine Artist & Mentor

Ann Rea is a San Francisco-based fine artist. She created Making Art Making Money, the leading and most reputable business program for fine artists since 2005. Rea’s art and business savvy have been featured on ABC, HGTV, Creative Live, The Good Life Project, in the book Career Renegade by Jonathan Fields, the San Francisco Chronicle, Art Business News, Fortune, and Inc. Magazines. Rea’s artistic talent was commended by her mentor, art icon Wayne Thiebaud. 

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