Phyllis .

Cyndy Porter grew describing herself as "ugly" and "stupid". After she struck gold and was able to retire at 38, she began her own business with the goal of making other women feel beautiful. With her branding and sales experience, Cyndy is now and image and stylist expert with a thriving business.

Watch the video, read the shortened transcript below or click here to listen to the Spotlight on eWomenNetwork Podcast interview at


(Partial Transcript with some edits from Interview below) 

From Ugly Duckling to Cinderella Story

PHYLLIS SMITH: I have to say when you applied to be a guest on my show I loved what you said. I’ve never done this before where I pull out what somebody writes about or describes about them self, but I just had to read this because it says so much.

Here is what you wrote, “I was born severely pigeon toed and had to wear special braces and shoes when I was young. Kids made fun of me for the way I looked and walked. I remember not only feeling lonely but totally alone like I had no life, no liveliness. In the first grade I was so insecure I would hide from eye contact. Sit and eat the buttons off my clothes. I was told by the school psychologist, he’d peek in window and he’d call home and he would tell my mom – “

This I cannot believe, “she’s mentally retarded”. Not only did I grow up believing I was ugly, but I also grew up believing that I was stupid.

Oh my god, how does one recover from that Cyndy?

Glowing Up: The Business of Personal Image & Self Esteem

CYNDY PORTER: It’s interesting because I’ve told my story, but I have never heard it said back to me. It does make me realize how far I’ve come. I was that sad young girl and it stuck with me through most of my life. It really wasn’t until my early 30’s after all of that bad experience continued to set me up for bad decision after bad decision.

I don’t remember if I shared with you when I wrote that to you that what I learned after 20 years of therapy is that when we start life feeling so badly about ourselves and feel like we are not enough we go into the world and look for evidence from other people that what we believe ourselves is true. When young girls and women don’t believe in themselves they will all the time do what I did which was not set good personal boundaries, allow people to mistreat me because I always felt I must’ve deserved it. For me it culminated in an abusive marriage and all kinds of things, but thankfully there was something in me that drove me to have a different life and I left all of that. It’s almost like I was completely a different person from where I sit today.

PHYLLIS SMITH: Sounds like you had to do a lot of work to get to where you are now. Because your business started out as a portrait photographer you obviously had this creative side. How did you let that creativity play out? Say as a child did you use that as an outlet in anyway?  

CYNDY PORTER: You know what, I didn’t. I was never creative. I was pretty much just a sad and lonely child that couldn’t find my way and I didn’t start to come into my own until I, I didn’t believe I was even smart enough, until I got into college and started to slowly believe in myself. When that happened, I started to turn things around. I think what we need is to start to see our self succeed at something. If you don’t believe in yourself and you’re not succeeding at anything you probably don’t want to put yourself out there because you just believe you’re going to fail at everything you try, right, when you really have low self-esteem.

When I started to believe that I was smart, I was capable, and I could get good grades I threw myself into college academically and then I took that and threw that into work. My first profession was not photography, but sales and marketing and I worked for HiTech for probably 18 years. What I tell people is in a way I was lucky I was not happy and so for me it was like my addiction of choice was work. It easily could’ve been a much more unhealthy addiction, but somehow I found work and I think I was trying to prove to myself and to the world that I was worthy and so I worked harder than everybody else.

PHYLLIS SMITH: You even describe yourself as a work-a-holic and if you had to choose an a-holic that was probably the best way to go. Did that play out in all relationships? When you’re a work-a-holic you don’t have time for any personal relationships. So how did that play out for you?

CYNDY PORTER: I got lucky that when I was in Colorado and I was in this abusive marriage I was given an opportunity to go across the country and go to work for what we now know as the internet, but at the time I had no idea what that thing was. There’s this thing called the internet and one day we’re all going to use it and advertise our companies on it and we have this startup and we want you to come work for us. I took about a 50k pay cut in order to leave the current job I had and go work for this thing called the internet and that small company got purchased by AOL and I was lucky enough to watch the stock split 8 times before I retired.

I probably would have burnt out, had a nervous breakdown, or something else unhealthy if I hadn’t landed with stock options and I didn’t have any good relationships. My friends were the people I worked with and when I “retired” at 38 I knew that what I needed to do was take time off to chill and I had still hoped that I could meet the right guy and have a child. I got super lucky that I met him quickly, that he wanted to have a child, and now I have this amazing husband that I consider a soul mate and he treats me like gold and I have this amazing now 14-year-old son who makes me happy every day. I feel really blessed that I was able to turn a negative situation into the life that I have now.

PHYLLIS SMITH: It’s incredible with what you went through, as horrible as it was, it gave you that drive. It’s so interesting to follow your journey, how this horrible – you work in sales and marketing and built this 18 year almost 2-decade career and then you suddenly become like rich at the age of 38 were you could retire and then you meet this guy. It’s like a Cinderella story almost but it’s a lot of hard work that got you there, to get you to this point. Do you think that without the work, all the therapy, learning and really understanding yourself, do you think that you would be able to have gotten to were you are now in a healthy marriage, in a healthy relationship with your son, and we’re going to talk more about your business, but also a thriving business?

CYNDY PORTER: Yeah, I do think that it was equal parts hard work and luck because I think you can – you know if I had met my current husband before I had done all that work I don’t think I would’ve been in a position to have been able to have the relationship. I remember when my therapist said to me quite a bit into our years of therapy, “The challenge now is whether you can accept happiness.” It sounds funny, but the truth is if you’ve known it it’s hard to trust and sometimes people sabotage themselves because we’re comfortable with what we know, and I think a lot of times people get stuck and can’t get unstuck because they’re just comfortable being uncomfortable.

  I think a lot of times people get stuck and can’t get unstuck because they’re just comfortable being uncomfortable.  

There was something in me that I can’t describe that always allowed me, I always had this dream and this belief that I could have a better life. I was never suicidal for some strange reason, I certainly could’ve been. I always dreamt a lot, you know I’m putting on a 3-day event in September and I plan to tell my story and what I want to share is how I went from there to here and so I’ve been thinking a lot about it. I do think a big part of it is I was able to visualize or think about or dream about having a different life and I knew that I was stuck and needed help. I read every self help book ever written and I listen to everybody who would talk to me and I follow people who were more successful, and I went to a lot of therapy. 

A Personal Brand

PHYLLIS SMITH: Incredible. Now you’re an image and stylist expert and what’s so fascinating is here you went from the kid with the braces and feeling ugly and horrible and now you’re consulting others on creating their own image. How did you take that leap? How did that happen?

CYNDY PORTER: When I left the corporate world what I knew was that I didn’t want to do that anymore. It didn’t do anything for my heart. I felt like I was making an already successful company more successful and wealthier wasn’t gratifying.

I knew I was lucky to have a 2nd chance at a career and I always loved photography. I started taking photography classes. I got certified as a photographer and won some awards and I said, “This is it. I love it.” I have a type A personality, so it can’t just be a hobby this is what I want to do, and I love, love, love the craft of photography. I think it’s terrific. It’s a great combination of tech and artistic so if you’re not 100% artistic you can still be quite good at it if you work hard and practice. I always feel like my success is because I was able to work harder than everything and everybody else. Maybe that came from my background of not feeling like I measured up, but I was just used to always working hard at things.

I loved it, but I quickly realized as I was getting into it that what I loved more than photography was helping women feel beautiful, and I saw that so few women didn’t feel beautiful and I was always amazed by that. Because I felt like you know this whole concept that I had of never feeling good about myself would really as I grew up be like this whole exercise of going into my closet of trying on outfit after outfit and looking in the mirror and just feeling like I didn’t look good and leaving my house and being late for things. How can we expect ourselves to go into the world and inspire other people, do our best work, show up as the passionate smart capable confident women that we are if we leave after 45 minutes of telling ourselves we didn’t measure up?

What I loved more than photography was helping women feel beautiful.

It happens so often to so many women and so I started to put the pieces together and then I was kind of accidentally invited to go to this image and style weekend. It was like a Tupperware party for image. It was like this lightbulb went off inside of me that with everything I know I can do this. All my branding and sales and marketing experience it’s an easy jump into well everybody should have a personal brand, not just products and companies and if you study art you know that there are seven elements in art that we use in making a beautiful portrait, painting, a piece of jewelry or whatever and we could apply all of those to us personally. That’s where I said this is what I’m doing, and I found an amazing mentor out in California who I studied under and got certified as a dementia consultant and I created my own system of first personal branding and then also how to use art principles to look at ourselves and see ourselves as art so that we look our aesthetic best. 

PHYLLIS SMITH: What I ask you is to become an image consultant and stylist you talk about important – the thing you seem to love the most is helping women feel beautiful. How do you get them to feel that way but also on the inside?

CYNDY PORTER: That’s a good question and that’s hard right? If you’re used to telling yourself negative messages the approach that I take is, there are many, many people that work on the inside out. There’s therapist, coaches and all kinds of things. I basically take the approach of the outside in.

When we first start to talk about a personal brand the idea is it’s not about how you can look like the classic beautiful girl or woman that would be on a magazine cover. I don’t talk about that ever at all. I talk about how the ancient Greeks defined beauty, I talk about things that are math, art, and science related as it refers to beauty and then I teach them how to focus on what they love about themselves, what are their best features, how do we emphasize their best features, and if you happen to have sensitivities how do we learn to de-emphasize or conceal those a little bit, right?

What I found is that what happens is as you start to focus on what you love about yourself . You start to know what colors and what textures and what shapes make you look your best in and you look in the mirror and you see reflecting back at you somebody that you’re proud of, somebody that you admire, you know that you feel good about. Then you go into the world and whether it’s in an elevator, a classroom or an office and you hear people say, “Oh my gosh, I love that color on you.” or “You look so great today.” or “I love that color on you.” or “You’re glasses look awesome.” Doesn’t that boost you every time and gives you some self-confidence and it’s to bad that we rely upon the external world to make us feel better about ourselves, but it really does work and so I really focus on that. Like taking baby steps to who you are as a person, what does that look like, do you know that your most powerful communication tool is how you look. It happens in nano seconds. People judge us, and we judge ourselves. If we can start to put ourselves together in a way that we take baby steps toward looking in the mirror and learn what we love about ourselves then we carry that with us. look in the mirror and you see reflecting back at you somebody that you’re proud of, somebody that you admire, you know that you feel good about.   

PHYLLIS SMITH: Describe it, what is a personal brand because you’re talking about looking at things you know, what do you love about yourself and then kind of work with that and accentuate that. Is that a personal brand or do you also help people sort of decide what that is.

CYNDY PORTER: Yeah, so when I work with my clients. We always start with personal brand because that’s the most important. I think if things aren’t like your best colors, shapes, patterns, or proportions but you are showing up being true to who you are authentically then that’s the first battle. Are you showing up in a way that you communicate who you are, right? In order to do that you have to know who you are. I take them through a series of questions, thought processes, exercises and I also do, you mentioned the exercise you did in your program, I do exercises so that they get feedback from each other and so it could be as simple as sometimes when I’m speaking in a group we have a stick it or a post it to put on their back and everybody will be given a pen and you walk up to them and say what is your first impression. There are always positive you know, pretty, gorgeous, creative, interesting, professional, lively, or whatever and then they get to pull that thing off their back and I usually have them think about number one how they see themselves and number two what they want to be written on their back.

So, I’ll often say if you were to get up and leave the room and we were all to say, Isn’t she blah, blah, blah, blah, blah.” What would you want that to be and it must be five or fewer adjectives, right? You can’t have twenty. Is it that you want to be edgy or is it that you want to be smart or is it that you want to be interesting or creative? What is it really that makes you, you? Then once we get to that core then how does that look? How does look in an outfit? How does that look in an earring? How does that look in hair cut? What make up is that? What eyewear is that? That’s the first step and then this other thing I was talking about with the aesthetics I all that owning your style and that’s more of using art elements to make you look your personal best on top of communicating your personal brand. 

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Elements of Art

 PHYLLIS SMITH: You talked about the seven elements of art. I don’t know what they are. What are they? Can you name them off?

CYNDY PORTER: I will try to so there’s line, proportion, shape, scale, value/contrast, color, and texture.

PHYLLIS SMITH: You consider all those things when you’re considering how you want to look. What I also think is interesting to is when you talk about a personal brand you’re not just talking about like one outfit you’re talking about creating a closet that is your personal brand. 

LCYNDY PORTER: So many women when I talk to them about their brand they’ll say something like I’m a mom and I’m a wife and I’m an accountant and I’m a soccer mom and it’s more like what they do then who they are. I think if you can get to core set of values and adjectives that describe who they are in all occasions of their life then you dress to those values and adjectives but then also to the occasion. So, you would show up differently for a black-tie affair then you would to go to a ballgame, but both outfits would communicate who you are as a person.

PHYLLIS SMITH: A simple black dress, but then there is a twist on the simple black dress that would fit into your personal brand.


PHYLLIS SMITH: Do you find that to know what your personal brand is, is that like your gut? Like for me it was this is what I love. When I see other people wearing, oh wait I can to.

CYNDY PORTER: Yeah, it’s usually more complicated than that. It’s something that I try to, you know whenever I try to take up less time when I’m working with people and I just can’t because the thing that and I think it takes us longer sometimes to unpeel the onion so I do a series of different kinds of exercises that get to your subconscious as well your conscious and I think that if you could go back to a time in your life when you were uninhibited and people said, “No, Phyllis you shouldn’t wear that or you don’t look good in that.” You know all that should have happened in your life, if you’re lucky enough that you didn’t have critical people around you then you might still have it, but a lot of us must go back to for example to who was your chosen icon, right? Was it Wonder Woman or Pippy Long Stocking or Cinderella or were you a tomboy or did you love like flowy dresses or did you like overalls. If you can go back to that time that will help you get in touch with your instincts. It usually takes a fair amount of work because we have so many should on how we feel if we need to show up that uncovering all of that and then putting it back together for a way that you feel is appropriate for your lifestyle takes time.

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Podcast Host and Author, Phyllis Smith

Director, eWN Podcast Network
Content Manager, eWomenNetwork

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