Living the Creative Life: Humor and Wisdom from Lee Silber

In this inspiring episode of Painterly Life, host Shannon Grissom sits down with Lee Silber—surfer, entrepreneur, award-winning author, and speaker—who has built a life around creativity and authenticity. Lee shares how his eclectic journey, from selling surfwear to writing bestselling books, shaped his approach to living creatively.

Together, they explore the importance of embracing your unique voice, using life experiences as fuel for art and innovation, and finding freedom from creative blocks. Lee also offers fresh insights on the role of technology and AI in today’s creative process.

Whether you’re an artist, writer, entrepreneur, or simply someone seeking more inspiration in life, this conversation will leave you motivated to live authentically and create with courage.

Chapters

• 0:00 Introduction to Creativity and Entrepreneurship
• 2:01 The Importance of Authenticity in Art
• 4:44 The Journey from Nonfiction to Fiction
• 7:42 The Wild Idea Club: Merging Stories with Lessons
• 9:24 Finding Your Unique Creative Process
• 11:13 Balancing Multiple Creative Outlets
• 13:16 The Power of Public Speaking
• 17:26 Overcoming Creative Blocks
• 18:46 The Role of AI in Creativity
• 21:36 Embracing Change and New Technologies
• 26:52 Conclusion and Resources

Transcript

Shannon Grissom (00:05)
Hi, I'm Shannon Grissom. Are you looking to ignite your creativity? Or how about be inspired by a steady stream of muses? Welcome to Painterly Life, the podcast that celebrates those who create, inspire, and innovate. So whether you're looking to spark your next big idea, reignite your passion, or simply soak in some creative energy,

This is the place for you. Painterly life, where every guest is a new muse, just for you.

Welcome to the Painterly Life podcast. I'm your host, Shannon Grissom. I'm really excited about today's guest. Lee Silber has surfed waves, sold shades. He's written 24 books and even gone homeless for research. He is a creativity wizard, an entrepreneurial wizard. So welcome, Lee.

Lee Silber (01:13)
that was a great introduction. Thank you so much.

Shannon Grissom (01:16)
You're

welcome. So you started out surfing and selling sunglasses. How did this whole thing evolve?

Lee Silber (01:27)
Well, if we're talking about creativity, I've always had that ability to come up with ideas, to take my ideas and create them into some form, usually art or some sort of a promotion or anyway, creativity isn't just the arts. I mean, if you're resourceful and you could fix something with just the things you have around, like a MacGyver, that's creative, right? Yeah. If you're able to articulate verbally what you

you know, like an actor or someone. There's all kinds of ways. So I found out that even though I fought it and fought it, I studied business and economics and accounting, it just was not a good fit for me. And so I was always beating myself up. I am dumb. I am not as good as everybody else. Why can't I just get this? And I don't know why or how, but anyway, I went to art school and I realized, okay, A, I'm amongst my people.

And B, I found that I'm actually really good at this. And other people say, I can't draw, I can't create, I'm not resourceful. And I'm thinking, well, I'm all those things. So finding that ⁓ confidence in something that I was good at, which is creativity, was the beginning of a long stretch of mediocre success.

Shannon Grissom (02:46)
Now you've actually lived your books. I mean, I'm thinking about going homeless, your time in Hawaii. So what was that experience like?

Lee Silber (02:58)
I always felt sometimes when you read something or you watch something and it doesn't feel authentic, right? It's hard. It's like you can't explain it, but you know it when you see it. Like this is real. This person has either lived this or they did enough research that they really understand it and they convey that. And it's not in a polished perfect way. It's imperfect. It's so true in music. You'll hear

those songs that were created by computers or something and it's just off. It just doesn't sound, there's no soul. So I felt like if I'm gonna write about a character or a scene or a situation, I should live it. And that included spending a lot of time with someone who was dying. And we met every Wednesday and she wanted me to write her life story, which I did. ⁓ I immersed myself as a undercover painter. I worked as a, in...

an office doing plant maintenance, all kinds of things so I could see what it was like to be in an office. And then, of course, as you mentioned, I actually lived on the streets for a while, a week, to see what it was like to be homeless. So my character who was homeless was, I thought, more real.

Shannon Grissom (04:15)
It really makes a difference. feel like that authenticity is so important. When I licensed my art on golf club head covers, I hadn't been golfing at the time. My dad was now the golfer and so it was a big part of our life, but I didn't golf. So I started taking lessons and I totally got into the game after that. ⁓ I really, I agree. It needs to be authentic.

Lee Silber (04:40)
Yeah, it's not a quantitative thing, but sometimes, you know, I mean, let's talk about De Niro. You talking to me? I mean, he was a method actor. And that's, guess, what I'm trying to say is to get into the character, he would become the character. And I think for any form of art, you really have, they always say, know, Mark Twain said, write what you know about, musicians have used, you know, their own heartbreak or...

trauma or whatever to put in their music and those songs seem to resonate more with people because there's something in there that it's human, it's identifiable, they can relate to it and I don't think you can fake that.

Shannon Grissom (05:23)
No, you can't. You you've written fiction and nonfiction. Well, out of any of your books, what book changed you the most?

Lee Silber (05:34)
Well, I should mention something. So I had a literary agent for years and she told me after having success in nonfiction, I said, I want to fiction. She said, no, you can't do it. It's just impossible. Nobody does both well. And I thought, great pep talk coach. Thanks a lot. So I started small. I started with just a book of short stories and it won an award.

So I didn't go, neener, neener, neener. I just said, OK, all right. And then I wrote a novel, and it did really, really well. And ever since, I've been able to write fiction. For me, writing isn't something that is painful. And I've heard so many quotes. It's like sitting there until the blood forms in your forehead, from your sweating blood. I find it very easy. I find it very natural. I love it. I mean, I don't golf. I write.

It's my hobby. when your hobby is what you do for a living, you're living the dream. And so the books, ⁓ I don't know if anyone out there will relate to this, but as creative people, we're more in tune to our intuition. And I think we have more of a belief in something like a force, the universe. You know, I've written songs that I don't even know where it came from. It doesn't even sound like me. I'm not a big country music fan. And the song came out country. I don't know how that, but we're...

we're pulling things from who knows where and we're channeling them out through our art, our creativity. And so some of the books that, and I'm not sure if I'm ever gonna answer your original question, but some of the that came to me, I don't know where they came from. Mostly dreams, to be honest with you. find like, I seem to wake up and then go back to sleep for a little while and in that little time where you're not deep in sleep,

I get some really strong, powerful images and messages and ideas and I write them down and I sit with them for a while and if it still sounds good a week later, I'm like, okay, this is something, there's something here. So the books I feel were just meant to help people and someone sent me the idea so that I would be the one to write them to make that kind of a difference. can't think I ever wrote anything that didn't have a message in it.

that I thought would make a difference. don't feel like writing just for the sake of entertainment. There's nothing wrong with that because that is a way to help people escape. I wanted to do something, even in my fiction, there's something in there that when you're done reading it, you hopefully learn something or thought it created a way for you to think about something important and evaluate it in your own life.

Shannon Grissom (08:21)
Well, and I think your nonfiction does that as well. And so it's kind of like they cross over. So you're getting messages in your fiction that are inspirational. And then in your nonfiction, yeah, it's got the nuts and bolts, but it's also got that other component to it. So that's what's really cool about your writing.

Lee Silber (08:43)
There was a book of the, I've written 27 books and they're all like my children. I don't have a favorite. Okay, I do have a favorite, but I won't tell you. It's like you shouldn't tell your kids. No, you're my favorite. The other one's, dang. But there was one called the Wild Idea Club and A, it was a collaboration with two other writers, which I really enjoyed. But we thought who wants to learn? The idea was how to get you the ideas from a company from the bottom up.

I got the idea from watching Undercover Boss. I thought when the boss would go undercover, they would talk to some of the frontline workers and they would realize, wow, these people are really smart. They don't have an MBA, they don't have the title of vice president, but they had great ideas. So how do we get them up? And I thought we could just write this book as a how-to, but let's turn each point we want to make, how to do each thing, into a story. And I thought that was my favorite. was listed as nonfiction, but each...

chapter was a different story and I thought, if we can anchor an idea to a story, they'll remember the story about Tony, the pizza guy, yeah? And there was a message that went with Tony and I thought that's probably the best of both worlds where Ken Blanchard was the master of it with One Minute Manager. It was a story, but even The Energy Bus, which is a more current book, they're parables.

Yeah. We're never going to get to all your questions because my answers are so long.

Shannon Grissom (10:12)
That's okay. Don't need to get to any particular place.

Lee Silber (10:17)
For the

listeners, I don't know what the questions are. I specifically said I don't want to know because I want the authenticity of hearing it for the first time and not having prepared the answer that everyone might want to hear but to tell the truth about what I really feel about something.

Shannon Grissom (10:32)
Okay, here's a random question. What's your secret talent that nobody knows about? I thought that might be a little hard because you've got so many talents and you share them with everybody. what's what?

Lee Silber (10:40)
Whoa.

All right, all right.

No, that's a good one. And I'm probably going to regret this. I'm good at taking something that exists and making it better. Meaning, all right, there's two ways to look at that. So what you're saying is you see an idea and you steal it and then turn it in your own. No, no, no. It just provides a starting point. Meaning to start from scratch, staring at a blank page or looking at a blank canvas or starting with it.

an empty Pro Tools or GarageBand window. That's frightening. But if you know, okay, I want it to sound like this, I want it to look like this, but it's gonna be me. I'm gonna put my spin on it. It's just a place to start. So that's a secret talent. I'm good at finding something that I have an idea and I see something that's either in a different industry or a different...

It's not related, but it gives me the starting point. And then I build from there. And by the time I'm done, it looks nothing like the original. But I don't know if that's a gift or it's just a secret that I wanted to share that some people who's like, I have writer's block or I have artist's block or I have whatever. Maybe that's the answer is don't start from ground zero or start from scratch. Find something to base your art on and then make it yours.

Shannon Grissom (12:16)
Kind of like surfing the fridge and seeing what you can make with what's there.

Lee Silber (12:21)
There's my secret talent. I'm very good at the leftover whatever dish that turns out pretty good.

Shannon Grissom (12:30)
So as a songwriter, author, speaker, how do all these creative talents work with each other?

Lee Silber (12:41)
Well, go ahead.

Shannon Grissom (12:43)
Well, I just wondering, you know, I know I, no matter what I'm working on, something's going to have a heavier focus at time. Do they all just, do you juggle them all at the same time or do you have something that you focus on for a while and then kind of, how do you do that? Do you eat, when you eat dinner, do you eat one thing at a time on your plate or do you just have a little bit of everything?

Lee Silber (13:09)
Well, you know, because ⁓ you read the book ⁓ Organizing from the Right Side of the Brain And so I'm more of a whole brainer, which I think a lot of people are where you're you have a sense of both in different times, maybe in your your art, your very right brain, but then you're able to balance the books and and stay organized or be on time. Those are different parts of the brain. having the whole brain approach. But what I like about what I do is

If you imagine, picture yourself driving down the freeway and if you're just changing lanes, you're still moving forward at a good speed. So all my things are sort of related. So when I, like every right-brainer, get bored with something, which doesn't take long, I could just change lanes and I'm still moving forward. But imagine you did something completely off-brand or totally unrelated to what your goals are.

It's like you're getting off an off-ramp and taking a meandering drive through the countryside, which is fine, but you're not going to get where you want to go as quickly. And so that's how I look at having a variety of things to do that are sort of related and they are just, it's like changing lanes. I should write that down. That sounded pretty good.

Shannon Grissom (14:28)
It's

a really good analogy, really good. So you've done over 1,500 presentations. How did you get started speaking?

Lee Silber (14:39)
I owned a surf shop. mentioned I was a surfer when I was younger. the principal said, well, all the kids in the neighborhood near one of my shops, ⁓ look up to you. Because you're a young entrepreneur, you're a skateboarder, a surfer. Will you come and speak at career day? thought, ugh. It's terrifying. Not just the speaking part, but the fact that these are eighth graders, middle school. Challenger Middle School I said,

Okay, and when I got there, she said, well, it'd be cool if you could just skateboard on stage. And then she said, but the exit is over here because you're probably not going to make it to the end. These kids are brutal. Okay. This is going to be scary. But at the end, I got a standing ovation from these eighth graders and that feeling of that. Cause I told them, I said, some of you out there are going to go to a four year college and you're going to get a job and you're to have a long career with one company or in an industry. And some of you.

are going to go to a trade school or start a business. And I want you to know they're equally okay. And that message really resonated because I'm sure some, I'm getting a little teary-eyed. Some of the kids in the audience were thinking, well, I'm, I have terrible grades. I'm not good at math. I'm never going to make it in a four-year college. wouldn't, my grades wouldn't get me in and I wouldn't make it even if I got in. But that doesn't mean you're less than, than the others. And I wanted that message to get across. So,

A, I felt like, wow, I really have something to say. And B, it was very powerful, the applause. mean, won't lie, that was pretty cool. I felt a little bit like a rock star, which I guess is my ultimate dream, which I'm still chasing, but it felt close. So I thought, boy, if I could do this all day, every day, wouldn't I be happy? And so I signed up with SkillPath Seminars, and I taught creativity and design.

And I did five days in five cities all day. And you know what? At the end of the day, I wasn't tired. I was energized. That's a good place to be in your work, where you work eight hours, well, six hours. But you're not exhausted. You're pumped up. And I did that for a long time.

Shannon Grissom (16:53)
Did you ever have any random experiences that didn't go as planned in all those?

Lee Silber (17:01)
Where do you get these questions? Maybe I should have previewed the questions in advance. Yes. I'm known for bringing the fun to my presentations and I like a lot of audience interaction. Sometimes that's the best lines or the best things come from that. So I had people, and this kind of relates to our audience, you could do it along with us. So I said, take your hands and clasp them together. Just clasp your hands. And notice which thumb, you're just naturally stuck on top. Now switch your thumbs.

and it feels uncomfortable. It's awkward. So what we want to be doing is things that are in our wheelhouse that were strong, you know, use our strengths that we're good at, that we enjoy. And that feels like the natural way you put your thumb. So there was a person in the, I think maybe the second row. And I said, come on, we're all doing it. Let's do it. And he slowly raised his hands and he had two claws. And so I, and this was in the very beginning of the speech. I thought, and I was,

devastated. I don't even remember how I finished, but I felt so bad for him and me, if I'm being honest, because I thought that was a really horrible moment. so after all those speeches, I still remember that one and another one where I kept telling the meeting plan, I'm like, am the wrong person for this group. They're stockbrokers. I'm a creative person. This is never going to work. They're like, no, they want you. And about halfway through, we took a break.

Well, we're just gonna finish on our own. can just go. And I thought, But that's twice out of 1,500 that went sideways. But those stick with you. And thanks for bringing them up and rehashing all that trauma.

Shannon Grissom (18:33)
Wow.

You

Lee Silber (18:49)
Honesty and authenticity, that's what this show is about. You made me cry, you made me laugh, you made me smile.

Shannon Grissom (18:52)
You

Been watching too much Barbara Wawa.

Lee Silber (19:00)
Right, what kind of tree would I be? Palm tree.

Shannon Grissom (19:04)
So for anybody who's feeling stuck creatively, have any tips to get them back in the saddle or started?

Lee Silber (19:14)
Well, mean, when you make a movie, you don't always start with the opening scene. I maybe the actor's not available or the location isn't available or whatever. And if you had to wait for that, would, you know, slow things down. It'd be harder. So they just film whatever is available at the time. And it's like that with any project. Start with the easiest part first and the smallest, the simplest. So you can get a little bit of, once you start or once you've begun your halfway down, meaning any

part of it, whether it's just getting your supplies out, whether it's ⁓ just scribbling something down or whatever, any place you can start, start. Because the fear, procrastination isn't really, that word is, it doesn't sound so bad. Well, it kind of does sound bad, but what it is, is it's fear, right? We're afraid. I don't know if I'm good enough. I don't know where to start. Will anyone even like this? And there's all kinds of fears that make us stop.

Well, someone else has done this. Who do I think I am? All these things. But if we just quiet that voice and we just make a quick, successful start, we can say, okay, all right, yeah, I'm on my way. I can do this. And your brain kind of relaxes and there you go.

Shannon Grissom (20:36)
So when you're writing, what's your favorite snack?

Lee Silber (20:40)
That's a good question vodka no You'll end up reading at the next thing oh what the heck was that Well, I do feel a lot of a lot of writers When they are artists in general when they struggle sometimes it's the time of day like if you start When you're at your lowest ebb of energy you're already, you know

struggling. It's hard. if that's the only time where you get up really early but you're not quite awake or you have to stay up really late after the kids go to bed and that's when you can create, you have no choice, you got a little chocolate, a little cappuccino, something to get your energy up. But if you have the choice of when you can do your art, you really should look at your own inner clock and say, this is when I'm most alert, most excited, most motivated.

most creative and try and don't give that time away. Save that time as you and use it. So whether you can create your own schedule and use your best prime time or you have to kind of raise your energy level. What's interesting is, and this I won't go deep into it, but we creative people, we don't want to be like everyone else. We don't want to work nine to five. We don't want to, you know, we like to stay up late, get up late, you know, many of us. And so

We want to be a little different, a little special, a little unusual, a little unorthodox. And so sometimes that quiet time that happens after midnight and it goes till two is the best time. There's nothing on TV. Well, that's an old, now there is because you could stream anything. But there's less distractions, I guess is what I'm saying. So, but basically it comes down to energy and prime time.

Shannon Grissom (22:30)
Yeah, yeah, I really like what you... And keeping that time sacred is so important. my best creative time is first thing in the morning. But I get up in order to have quiet time based on what's going on. I'm up at 2:30 in the morning every morning. And so I've got this weird artist schedule, right? So I get up and that's... I get more done between then and eight o'clock than most people do.

I have a whole day in there. And then no matter what happens during the rest of the day, I put in my creative time. So yeah, it's, and if I don't, it goes to hell.

Lee Silber (23:11)
Yeah. Oprah used to say if you don't get your exercise in first thing in the morning, there's less, the chance of you ever doing it keep going down as the day progresses. And I think that's true of art too. Unless you do it in the late in the evening.

Shannon Grissom (23:27)
Yeah, yeah, there are people that are better at night and not me. don't have my brains gone by then. And I have to follow when it's there. Or at least when I can be a direct channel for whatever's coming to me. So what you working on now? What's your latest project?

Lee Silber (23:50)
You know, you could hear about things and panic, right? Because AI is freaking people out. And I'll be honest, I'm not thrilled as a creative person when it can make music, it can write copy, you know, it can create just about anything. And as a creative person, that's frightening. ⁓ On the other hand, as we talked about authenticity, I mean, at this point, it's not there yet. Sometimes you'll read something and it'll sound...

That doesn't sound like a human wrote that. You know, can even sense it. So, but then I thought, well, why fight it? And so I've always had an idea for an app, but the barrier to creating it was I'd have to pay somebody to write the code and I couldn't afford it. It was too expensive. Thousands and thousands of dollars to create an app. Now I can do it with AI for next to nothing.

So I'm working on an app. It's still me. It's my idea, my design and everything, but under the hood stuff that I'm not good at, ⁓ AI can do it for me. So it's providing an opportunity that I wouldn't have had without AI. ⁓ So what is it? Either fight it or embrace it. There's a better way to say that. But what I'm saying is I did freak out for a little while, but then I thought, okay, how can I use this to my advantage?

what I'm doing. It's an app. I have two names for it. ⁓ one is Kachow, which I'm probably not going to use, or Hashmark. it's, I think that's the one that's going to stick, but it's about throughout the day, taking note of when someone gives you a compliment, you accomplish something, you do something well, or you're acknowledged for doing something well. It's a simple app. You know, just keep track of those and you try and basically win the day.

Shannon Grissom (25:47)
Oh, I love that. it really helps you. Cause your whole, everything you do is focused on the positive. So that's just the perfect tie-in to what, what you do. And I love, you know, there, there, there are things that scare me about AI and there are things that I love. You know what? found it to be really cool for dream interpretation. Oh my God. It is great. I, know, so I'll

Lee Silber (25:57)
Thank you.

Who ever tried that?

Shannon Grissom (26:14)
because it calls my stuff. It's things that I wouldn't think about or I'm like, don't want to see that. ⁓ So I key it in and I'm like, dang, that was good. You got to try.

Lee Silber (26:27)
I will, that is good.

Shannon Grissom (26:29)
⁓

I mean, I've tried it for more practical things, but this is fun.

Lee Silber (26:34)
No, I believe when I have these dreams that they're sent to me, like I said, sometimes it's to create something, but sometimes it's just to warn me or push me in a certain direction. But I want to add something about AI. Again, kind of in my thing, the impediment was it was too costly to do an app without this kind of assistance. But so many people say, well, I would write a book. My grammar is awful. Not an excuse anymore. Right? The ideas are what's unique.

and you have that, the AI will just fix it. And sometimes when I put something through that filter, it changes too much. So I will just take some suggestions from it. I don't use all of it, but it will correct the grammar. And so we talk about procrastination. You said writer's block or artist's block. And sometimes it is that fear of, I want it to be perfect, but I don't know if I can ever get it perfect.

But actually, you could get it close to perfect now, and that's not an excuse. You have ⁓ a personal assistant if you want to embrace that.

Shannon Grissom (27:39)
it's, it's, you know, I, as a solopreneur, I can't do everything myself. There's just not enough time. do as much as I can, but it's really helped me out a lot. I mean, even for the transcription of these podcasts episodes, I just plug it in and it, and it transcribes for me. And there's very little correcting that I have to do it. So otherwise it would take me hours to do that. So yeah, it's awesome.

Lee Silber (28:05)
One more thing, recently, we have to go. I knew it.

Shannon Grissom (28:10)
We have no little... Yeah.

Lee Silber (28:14)
Well, I just wanted to add. people now ⁓ are reading less than ever. And I realized that as a writer. So I decided that I want to create an audiobook. So I recorded an entire audiobook in a studio, sent it to Audible, and they're like, it's not good enough. Like, And so I kind of gave up on that idea. And then just recently, if you publish through Amazon, their KDP, On Demand Publishing, that it will...

turn your book into an audiobook with an AI reader. It's not perfect. And it took five, it only took five minutes to do it. wow. ⁓ I, and it costs nothing by the way. So I'm just saying there is, we're in a window now where if you're not interested in it or you don't think it's for you, ⁓ just revisit that and see if there's some way you can use this to your advantage. Like you said, to help you with your business, to do the,

the things you're not willing to do or don't do well, maybe it's what you need to get over the hump.

Shannon Grissom (29:19)
And really even for the woo-woo things like the dream interpretation, anytime I can get some insight on what's going on in my life, I'm going to be more productive. So it's good. So where can people find out more about you?

Lee Silber (29:37)
⁓ it's easy. full name is L-E-E-S-I-L-B-E-R-LeeSilber.com. I've got free things. I've got all kinds of information that I'm a giver. I got that from Seth Godin. He said you give to get. First you give. It's like a checking account. You can't write a check against an empty balance. So you do for others. And then if you ever need a favor, you can ask for it. And you have some balance in that.

account where you've given and given and given. So I'm trying to give away as much as I can.

Shannon Grissom (30:12)
Well, you can tell on your site, it's all kinds of good resources for folks. So I encourage you all to visit. Well, thanks, Lee. You've been totally inspiring. This was fun.

Lee Silber (30:24)
Yeah, I love the questions. There's a couple in there that were really, really good. Good for you. Awesome, thank you. You can put a hash mark on your hash mark. Ka-chow, ka-chow.

Shannon Grissom (30:35)
I will!

Yeah, so you'll have to let me know when that app comes out. That's great. Good. Well, thank you, everybody, for watching and being joining us on Pingerly Life. Please be sure to like, subscribe, and we will see you next time. That's a wrap.

Lee Silber (30:41)
D

I know.