Business for Self-Employed Creatives

Jaimee Finney is a lot of things - a designer, a writer, a speaker, a coach, a mom, and so much more. She's the co-founder and CEO of Picture This Clothing, a company that turns your art into clothing. She's always experimenting her way into new ideas about what she wants to do.

In this episode, we talk about how hard it is to answer the question "What do you do?" when you do so many things. And how trying to simplify it into a definition others understand can place unnecessary limitations on your abilities.

We discuss our belief in optimism and how it's not just about looking on the bright side, but an active practice in finding the good in life. Even through the pandemic and a series of heavy personal events, she focused on the positive and came through stronger than before. One of her greatest strengths is her ability to help others understand the tools they already have within them and organize them in a useful manner.

Her biggest piece of advice is to not put all your eggs in one basket. Having side gigs and other sources of income, along with doing different types of work, are what have given her the freedom to choose what she wants to do. So while some might say, "you do too many things," we believe that allows us to create new opportunities we wouldn't have if we stayed in one bucket.

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Connect with Jaimee @jaimeejaimee and @picturethisclothing

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00:45 If you can endure a three-day road trip with someone, you know it's good. You could work together.

03:20 You look at Walt Disney, and you look at Jim Henson, and the vision they had, and how much resistance they got for their ideas early on. But they found a way. They had a dream. They had an idea. They had passion, and joy, and fun, and playfulness, and they brought that to the world in a huge way. And I just think that's hugely inspiring.

06:41 I feel like I have a lot of ideas, and things I want to try, and things I want to make. We're always trying things. We always have ideas, and so getting them out of our head and into the real world is just a practice for us. It's a life. It's who we are.

What is it that's pulling your focus? So if it's pulling your focus, see it through, finish it up, and throw it out in the world and see what happens. That's how our business, Picture This Clothing, was born. It was a proof of concept.

09:14 What I started doing was figuring out how to just do. Do things, but not just start, actually finish. And so what I learned through that process, a couple of years’ worth of trying sprints and basically applying the product design process to my life, is something that I call Tiny Challenges, and it's kind of a silly little thing. But basically, you define a small window of time - it can be five days, seven days, ten days, whatever, one month - but do something very small for that amount of time. It's always a part of a bigger goal. You break it down into a really small manageable pieces, and you chip away at it slowly over time. You'll look back and go, oh my gosh, I just made like a 30-day body of work. That's huge. That's progress.

12:09 I’m a great collector of domain names and lost ideas. Something that I really learned over time is, just get this small nugget of the idea, enough to get the idea out, enough for it to be good enough quality for people to understand what you're doing, what it is, and how to work with it, how it's intended to be engaged with, with quality and thought. But don't dump every dime into your idea until you know it's worth it. 

14:26 You ask if there's a process. I think having an idea, writing stuff down. Because you may get started on it and then get distracted in 1000 different ways, and actually come back to the idea. I think documenting your ideas is really important.

15:14 I think having a product, you depend on different things and different bodies of knowledge. I've done service providing as well, where I was coaching, where I was teaching, where I was doing workshops and conferences, and all of that. And the biggest difference for me is we have something that we have to physically ship to a person.

19:14 I don't think we're a clothing store at all. First of all, we're an experience. And so, just in case people are unfamiliar with what Picture This Clothing is, you print out a coloring sheet of a dress, a T-shirt, we have beanies, face coverings, and then we have leggings as well. So we have a few products, and you print out the coloring sheet. You design it any way you want. You upload a smartphone photo to our website. We send it back ready to wear. And that's what Picture This Clothing is. And so it's all about that design experience that you have at home. And it always was that, even before the pandemic.

26:38 It always drives me crazy when people shut it down without thinking of the bigger possibility, or the bigger vision.

30:09 People love experimenting, and playing, and sharing their own ideas and their own imagination, creativity, and we all talk about it and try things. And so that part's really cool. 

33:43 Something that we've always done, but that really played well with the pandemic, was not having all our eggs in one basket. And I think as a self-employed sort of person, that's something I learned many, many, many years ago. Even if I had a full-time job, I was usually freelancing, designing websites for people or logos or whatever, on the side. I almost always had side gigs. And so even now, even though Picture This Clothing is the thing that requires most of my attention, I still have another business on the side. Ken still has another business on the side. So we have other things bringing in income. Don't rely on just one source of income at any time, if you can help it. 

38:02 It's a struggle when people go, “What do you do?” to answer that. I do a lot of stuff and I hate being dropped into a bucket. Like, I am a writer, I am a designer, I am a CEO, I also do our books and our finances and I can do strategy. I am a social media person. And we wear a lot of hats when we're self-employed, do we not?

I remember trying to simplify and say I'm a designer, but then it completely undermines my abilities. I am, in many capacities, a designer, but I am also much more than that, and I know that. And I think I'm limiting myself and holding myself back by simply trying to slap the label on so that people understand. And then I'm getting work that I don't want. And I'm like, No, this isn't what I meant. This isn't… No, this is an ill fit. And it’s my own doing, but untitled. I'm untitled.

43:34 I've been just really rethinking my own branding, and my personal brand, and what am I? How do I describe who I am and what I am? What do I really want to be doing? You know, people always ask that question, "If you had a million dollars, and you could do anything that you wanted..." Well, I'm not saying that I have a million dollars, but I'm saying I can do anything that I want to do. And I've put myself in a position where I've worked hard enough and that I can decide that I want to do this, or I want to do that. And I'm trying to decide what is it exactly that I do want to do for a while? And I never know. I've never had the answer. And I kind of just end up where I end up, and I do what I do until I don't want to do it anymore. And then I start experimenting my way into something else. And so that's where I'm at.

47:07 I've worked really hard to be able to make that a part of my life. And I'll keep working really hard. Like I love working on things I love working on. I just want to keep that freedom, you know? I want to keep that freedom because that's everything to me.

47:49 I don't know that I can prevent any burnout from ever happening again. But I know that I have the tools to survive, overcome and be resilient. That's what I'm really good at in my own life. I practice this regularly. And I find myself up against the wall regularly and needing to put those tools into practice. But I do feel like I always come out on the other side, and I'm okay. And I'm still going, I'm still fighting. And I think that there's just if there's anything I can do to help people understand their own toolset and how to apply it to get themselves on the bright side, that's probably one of my greatest strengths, and what I hope to be able to give to people. I believe that everybody has those tools within them already. It's just really discovering them and organizing them in a way that that's useful.

51:17 I know there's so much more to it than just looking on the bright side. I am not naive to this and not impossibly optimistic even, but I am a hardcore believer in optimism. It's a part of my soul. It's a part of who I am. And I can't help but to keep moving forward with hope. I will tell you that it's not easy at all times to do that. It takes practice and it takes thoughtful focus, dedication to mindfully choosing, like, what's good today. What's something good that happened?

52:11 Don't put all your eggs in one basket. I just think that's really helped me not get stuck. It keeps my options open and keeps my freedom as my underlying… and when I say freedom, my ability to choose. My ability to not have to go work for someone else unless I choose to. I hope I can always retain that. But I think having five or six little baskets with eggs in them has given me that freedom.