What’s it like to take evening classes while working full time to expand your career options? In this episode of Career Relaunch, Chris Donovan, a former telephone repairman turned high-end women’s shoe designer, shares his thoughts on doing work that’s authentic to who you are and how to deal with being an outlier when you’re pursuring a new career path. Afterwards, during today’s Mental Fuel, I’ll talk about being who you are, but doing it in a way that still allows you to resonate with the right people.

Key Career Insights

  1. Stability is nice, but at some point, you have to decide whether that stability is fulfilling enough for you.
  2. You are always going to face obstacles when you’re starting down a new path. You just have to keep talking to more people to figure out away around those obstacles. You can’t give up because you never know when you’re going to stumble upon the right person who can open a door for you.
  3. Fear and excitement are related feelings, especially when you’re doing something you never thought you would be doing. Face it. Embrace it.

Tweetables to Share


Listener Challenge

During this episode’s Mental Fuel segment, I talked about the importance of identifying one aspect of your personality that could serve you well in getting there. I call this a personality asset. What’s one part of who you are that you’ve maybe been holding back, for WHATEVER reason, but could actually benefit from showcasing? I want you to give yourself permission to let it shine. For some help in articulating the various aspects of who you are, you can download my “Personal Branding Starter” worksheet.

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Useful Resources

One of the things Chris and I spoke about on this episode was being true to yourself and making the most of who you are at work. This topic is especially relevant if you’re one of those people wrestling with whether or not to “just be myself” at work or flex who you are to meet the specific standards and expectations of your organization, even if that means NOT being yourself. This article from Fast Company entitled Should You Hide Your Personality at Work touches on this.


About Chris Donovan

Chris Donovan FootwearChris Donovan who spent 25 years repairing phones, but recently decided to revisit his childhood fascination with shoes to become a high-end women’s shoe designer. With the tremendous support and enthusiasm from his husband, he retired early and was accepted at Polimoda Fashion Institute in Florence, Italy. He’s recently found a potential manufacturer, and is now working to create and launch his first shoe line. You can follow Chris on Twitter, Instagram, Facebook, and Pinterest.

Watch Chris Donovan’s full AARP featurette:

Check out some of Chris’s shoe designs

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Episode Interview Transcript

Teaser (first ~15s): ‘Look around the room,’ she goes, ‘all these 20-year-olds, they’re fashion. You’re not.’ She looked at me, and she goes, ‘You’re crude. Do crude, and do what you know,’ is what she was saying, ‘Be who you are.’ In the beginning, I kind of had lost that.

Joseph: Good morning, Chris. Welcome to Career Relaunch. I am so excited to have you on the show today.

Chris: Hi, Joseph. I’m really glad to be here.

Joseph: I was wondering if you could just kick us off by telling us what you’ve been focused on in your career and your life right now, Chris. I understand, you just got back from a trip to Italy.

Chris: I have. I’ve been looking for manufacturing for my first line of high-end women shoes. Being new has made that a real challenge, but this last trip was very successful. I think everything’s in place for me to get my first line manufactured.

Joseph: Wow, very exciting. I want to come back to that, and I want to talk all about your experience of becoming a shoe designer and going back to school in a fashion school in Italy, but I was wondering if you could just start off by telling me little bit more about your former careers. Let’s go back in time and before you were a shoe designer. Can you tell me about your time when you worked in telephone repairs?

Chris: I started working for the phone company because I knew they paid for college. I figured, ‘Wow, that’ll be a great way to get my bachelor’s and have them pay for it,’ but it was one of those jobs that you get into that was very secure. It paid really well. I was able to move around to different types of jobs if I found one I didn’t like. I started out as an operator, which was just awful.

Joseph: What was awful about that?

Chris: I was the zero operator. I’d work the 11:00 to 7:00, so all night. You did not deal with business people. You dealt mostly with all sorts of emergencies. It was just a different crowd at night. It was really unpleasant. People will say anything if they can’t see you, so I got yelled at all night long and called all sorts of names.

I knew I wasn’t long for that one, so then I transferred to another position. I think, in my 25 years with the phone company, I must’ve had eight different jobs. I kept on transferring, trying to find something that was somewhat fulfilling, and I did not find it.

Joseph: Did it ever cross your mind to leave the company and do something different? Or was your mind pretty much set on staying within the company because of the benefits and the stability?

Chris: I came from a background where you get into a good company, and you stay there. It felt good, especially growing up, there wasn’t a lot of stability. This was a change for me. It was something that was desirable. I think over those years, I realized that security is okay, but it’s not the only thing. You realize that you’re not going to be fulfilled just by being safe.

Joseph: Did you have any inclination that you wanted to do something else?

Chris: I’ve drawn shoes since high school, but never ever thought of it as a career because I didn’t know anybody who ever went into something like that. How would you even begin to do that?

At one point, I did check design schools in this area. There are no shoe programs in the United States. The design schools I checked were extremely expensive – no way that I could afford. Those weren’t covered under tuition reimbursements, so that would have to come out of my own pocket. Considering the fact that they didn’t have anything in shoe design, it didn’t seem to make any sense to make that leap.

Joseph: It’s interesting, because we’ve been talking about the telephone repair industry, which I’m going to call it this very entrenched industrial industry. Now we’re suddenly talking about shoe design. Can you take us back to those high school days when you were first doing those shoe sketches? What interested you about shoes?

Chris: I went to a Catholic high school. It was in the 70’s. The girls wore the ugliest uniforms you ever saw. They were thick polyester. They were mustard yellow and a fluorescent blue. The only thing they could do to express themselves was they would do their hair as high as they could, and their shoes were just outrageous.

I remember seeing one of the girls walk into class once in these extremely high platforms, and I was totally fascinated watching her walk, and figuring out how it was possible. She could walk on these massive structures. I started sketching in my notebook, trying to figure out ‘If you can do that, what else could you do with a shoe?’ It just totally fascinated me, and it never went away. I sketched shoes for 40 years – on the back of napkins, on the back of work orders, on menus, on anything.

Joseph: It sounds like this was a really long-held interest and passion of yours, and yet you didn’t pursue it right away. One of the things we talk about on this show is these turning points or these trigger points for people that make them rethink their life. I know when we spoke before, Chris, you told me that you had something come up with your health at the age of 50. What happened?

Chris: I had started thinking about what I can do to make some changes in my life, and then I was diagnosed with prostate cancer. It was caught really early. Usually, you’re not 50 when you’re diagnosed with it, but they caught it really early. I went through surgery. I’ve been fine ever since, but it gives you a different perspective that ‘I’m not here forever’ and ‘am I going to be happy on my death bed, looking back and saying, “Wow, I was the best phone repair guy”?’ and ‘oh, I was really, really safe. I always played it safe.’ It was like, ‘No, I don’t want that to be me.’

I knew I had a passion, and that’s when I said, ‘You know what? This is stupid. I got to go do something.’ The biggest fear was having cancer and possibly dying from it. It’s just like, screw everything else and just go on and do what you need to do. Who knows what’s going to happen? But you got to give it a try.

Joseph: Can you take me to the moment when you first heard that diagnosis? What’s it like to hear that you’ve got cancer? What ran through your head at that moment?

Chris: It sucks. As soon as the doctor says that, you go deaf. You don’t hear anything else after that. I had no idea what he was talking about as far as treatments go and stuff like that. It was a shock. It took me a while to figure it all out.

I remember going to my primary care, and when I walked in he starts talking to me. This is after the diagnosis.

He goes, ‘We’re going to check your blood pressure. We’re going to do this. We’re going to do this.’

I’m like, ‘Hello! You didn’t even mention the cancer.’

He goes, ‘Oh, we’ll take care of that.’

I’m like, ‘Really?’

He goes, ‘Yeah. We caught it early. You’ll be fine. There’s a ton of different treatment options, so don’t worry about it.’

I’m like, ‘Okay.’

He was right. They took care of it.

Joseph: That’s great news. What prompted you to go from getting this diagnosis to then deciding to become a shoe designer?

Chris: I always scoured the internet for things like classes, anything to do with shoes. There were no classes. There were no workshops. There were very few things available. There were places where you could go for a week and learn how to build a shoe.

I saw a 2-day class on how to start your own shoe line, and it was given by a shoe designer and teacher. He was going to be in New York for 2 days. It was a Saturday and Sunday. I looked at it, and I’m like, ‘You know what? This is my chance to show somebody in the profession my stuff,’ so that’s what I did.

I signed up for the class. I went to New York for the weekend. It was me and 19 women, which was kind of funny. He went through a whole day of exercises as far as designing goes and stuff like that.

Afterwards, he had me stay after class, and he just said, ‘You have to do this. You were born to do this,’ which was the first time I’d ever heard that, especially with such input. He goes, ‘You have to go to Europe. You have to go get a Master’s. I will write you a letter to get into any school you need to, but you have to go.’

As thrilling as it was and as exciting as it was, it was like, ‘How am I going to do that? I have a house. I have a husband. I have a big fat dog. I have all these stuff going on in my like.’ I was like, ‘Who does that?’

Joseph: Was there anything else that made you nervous about going back to school?

Chris: The only international travel I had ever done was to Canada. I had not been to Europe yet. It was terrifying going back to design school, because other than what I did on my own for 40 years, it was brand new to me. I had no idea how I was going to deal with it.

Joseph: Let’s talk a little bit about your time heading back to school then. I’d love to dive in a little bit on this topic, because a lot of times, people think about going back to school and what it takes to go back to school. In your case, I know you eventually did end up going to Italy, but what was your process of finding the right school for you and applying and getting in.

Chris: Italy was the place for shoes. I knew that there were some excellent schools there. Aki, the teacher who told me I should be going, said, ‘There’s an excellent school in Florence that I really think you should go to.’ So I applied there with my sketches that I had, and I had to do a phone interview with the director there. Most students were in their early 20s. I was 55 at the time. I think there was a lot of skepticism on their end, but once he talked to me, that’s when he said, ‘We’d love to have you.’

Joseph: This was at the Polimoda Fashion Institute in Florence Italy. Is that right?

Chris: Yes.

Joseph: What was it like once you got there? I’m interested in a lot of different aspects of this, Chris.

First of all, what was it like to be 55 in school with a bunch of folks in their 20s?

Chris: I didn’t really see myself as 55 really, but it popped up a few times where I got mistaken for a janitor a couple of times. I was older than the teachers. If you see me, I look like a telephone repair guy. All I had were old jeans and old T-shirts.

These are fashion students. They looked amazing. They dressed to the nines every day. I did not look like a design student at all.

Joseph: How did people react to you when they saw you, knowing that you didn’t really look like the stereotypical student there?

Chris: I got a little bit of blowback where there was a couple of students who said I didn’t deserve to be there because I didn’t have any design background. She didn’t mention me by name but she directed this right at me. I was like, ‘Wow. It’s like you’re saying I don’t belong here.’ It didn’t bother me because I’m 55 years old, and I’m a lot older than you, and nothing really bothers me. That was the advantage of being older, I think.

We would have reviews. They call you in once a month to check on your projects and check on your graduate collection. The other students were always leaving crying. Just like you see on TV on some of the design shows: they kind of rip you apart. I know when I went in, I was like, ‘Nothing you’re going to say is going to upset me that much,’ but they were pretty nice to me. They were really nice to me. They like my stuff.

Even at that point, I’m like, ‘Are you just being nice to me because I’m old? I want you to tell me the truth. I’m here to learn as much as I can, and you have to be totally honest with me and give me as much information as you can because I want to make this work.’ They were honest. They said, ‘No, we actually think you have some great design skills.’

Joseph: It’s really interesting, because you mentioned that you didn’t think about your age as much as I think someone would going back to school that age. Was there something about that experience that made your age irrelevant, at least to you?

Chris: I was so excited to be doing something that I love to do, and the course load was intense. I had to come up with five-pair collection of shoes. I had to come up with accessories. I had to do a book. I had to do a movie, and I had to build also to other shoes to prove that I was capable of making Oxfords and loafers and pumps. It was a tremendous course load.

I was so focused. I’d never even thought about my age. For me, this is a dream. I’m going to have a great time doing this.

Joseph: One of the things I remember you talking about in the ARP video is finding your style. Can you explain to people how you found your design style and your design voice through the course of your time there at the Polimoda Fashion Institute?

Chris: Going to Italy changed everything. I’m so glad that I took the trip because I see everything in a completely different way now. I didn’t have any influences in the last 40 years, and it’s not like I sat there and copied other people. These were all ideas that just came out of my head, and I try to articulate it on paper.

When I got there it was a fashion school. Everybody’s walking around looking beautiful, except for me. I was trying really hard to figure out what they were trying to teach me.

There were at least three different points in the beginning that I thought I was going to quit because I wasn’t getting it. They were trying to teach me ideas of collection and research, which were totally new concepts to me. At one point, one teacher came over to me and said, ‘You know I’m really worried about you. You’re not getting this.’ I go, ‘I know I’m not getting this. I’m worried myself.’

There was a light-bulb moment. One of the teachers came over to me. I was trying to work on my book, and she comes over, and she was looking at my images and all the stuff I was doing.

She looks at me and she says. ‘That’s awful!’

I laughed and like, ‘What do you mean?’

She goes, ‘You’re trying to be fashion.’

I go, ‘It’s one of the top 10 fashion schools in the world.’

She goes, ‘Yeah, look around the room. All these 20-year-olds, they’re fashion.’ Then she goes, ‘What were you?’

I go, ‘Well, I was a telephone repair guy.’

She looked at me, and she goes, ‘You’re crude. Do crude, and do what you know,’ is what she was saying, ‘Be who you are.’

In the beginning, I kind of had lost that.

As soon as she said that things, started changing. I’m like, ‘You know what, I know what she’s talking about.’ As soon as I did that, all of a sudden, all the other teachers were like, ‘You’re getting it. This is exactly what we’re looking for.’ I ended up graduating at the top of my class and opening the final show, which really made me happy since that other person said I didn’t belong there.

Joseph: Absolutely.

Chris: It was a turning moment. It worked out amazingly well. They actually ended up sending some of my shoes to Dutch Design Week for one of their design shows. It was a great experience.

I think one of the funny things though is, when I was leaving and we’re having dinner with one of my teachers, I said, ‘What’s the possibility of me actually getting a job when I go back?’ He looked at me and he goes, ‘None. You’re 55, and you’re just starting out as a designer, so probably not.’ Coming home, I wasn’t sure exactly what I was going to do.

Joseph: One of the things that I noticed—and I know nothing about shoe design—when I look at your shoe designs, they are quite, for lack of any sort of technical term here, they’re kind of raw and industrial looking to me as an average layperson. It seems quite niched. At the same time, your voice really comes through. I can completely see how you designed those shoes. It seems like you really found your niche by allowing yourself to be you.

Chris: One of the big things that I’ve learned is that you got to be authentic in everything you do. I’m not going to fake knowing something. I’m going to be totally honest and open. My whole story has been totally honest and open. People understand that. People know that you are who you are.

I think that comes across in my designs. I think it comes across in the way I do business. I know I don’t know everything. I don’t have an ego that way. I will search out people who can help me, because trying to do this with absolutely no knowledge would be… Oh, god. No, I need help, and I look for people. It’s amazing how many people really want to see you succeed.

Joseph: Speaking of diving into an area that you might not have a lot of experience in, can you tell me about your process of taking your ideas now and trying to actually manufacture them? What’s that process been like for you?

Chris: Extremely difficult.

Joseph: I figured.

Chris: Right from the start, when I went off to school and stuff like that, there were all these obstacles. Some of them seemed almost insurmountable at points. The very first thing that happened when I was going to leave Boston was I went to the Italian consulate. I had all my acceptance papers from Polimoda and everything, and I was applying for a student visa.

The woman behind the counter said, ‘You can’t do that.’

I’m like, ‘Why?’

She goes, ‘You’re too old.’

I had to go back like five times to prove that I was actually going back to school in Italy.

All along, there’s been problems. What I’ve learned from that is, ‘You know what? I’ve gotten through and I’ve achieved so much to this point that, no matter what comes up, there’s always a way. You will figure out a way.’

When I started looking for manufacturing, there was no roadmap. There was no menu of how to do this. The whole process can seem quite secretive. Manufacturers can’t talk about who they work for. You have no idea where shoes are actually made, in what factories, where they are. You can not go into Google and type ‘Italian Shoe Factory,’ because nothing’s really going to come up. You just have to keep on figuring out ways of discovering.

I used every power of the social media to meet other shoe people, ask them questions. I found out different ways of searching out information through hashtags and all sorts of other stuff, to find out all these little bits of information. Some of it was useless, but it got me to the point where I was like, ‘Oh, I’m beginning to find some factories.’ I started writing to them, which is not the normal thing to do, but what do I have to lose?

I just started writing to them, saying, ‘Listen, I’m looking for a manufacturer.’ Some got back. Some ignored me. It was difficult finding anybody who would actually talk to me.

Most manufacturers, I’m discovering, are very, very hesitant to work with somebody new, because factories aren’t creative. They don’t look and go, ‘Oh my god, you’re amazing.’ They don’t really care about that. They care about, ‘I got to produce shoes and do this, and we’ve got to have lines.’ They have big, big companies coming in all the time producing 50,000 pairs. That’s their bread and butter.

Then you have this new designer that comes in and says, ‘I want to do 300 pairs.’ You don’t carry a lot of weight. You just have to throw yourself into it, talk to as many people as possible, and get as many network connections as possible to actually find a way to get there. You just don’t give up. You just keep on trying.

Joseph: What exactly did you do in your most recent trip to Italy that you just made a few weeks ago?

Chris: I was actually accepted into a project team. They work with me. They’re actually very excited about my stuff. It’s going to be a luxury shoe line, but it’s also going to be really different.

That’s funny. They kind of said the same thing you did, that my designs are masculine and feminine, but also raw at the same time. I’m not one of those people that go for pretty. My first designs that I’m having done were inspired by wood lathing. I was watching the guy do these incredible, wild, pepper mills. I’m like, ‘Wow. I could really use your ideas to make some incredible heels.’ That’s where that came from. That came from woodworking.

Joseph: The last thing I want to talk about, Chris, before we wrap up by talking a little bit more about your first shoe line, is just some of the things you’ve learned along your career journey. I know you’ve touched on a couple of them already, but one of the barriers we talk about on this show is related to fear. I’m just curious, what’s something that you’ve learned about fear during your own journey?

Chris: Our natural reaction to fear is to avoid it, I think. I understand why, but what I’ve learned is that, if I’m nervous about something or if I’m afraid of something, it probably means I should head in that direction as opposed to running away from it. Because if you want big things to happen, and if you want to achieve big things, I think, you need to face all that stuff. You take that fear and kind of reframe it.

I heard a story, this woman was talking about fear. She was on the bunny hill in skiing. She was 40 years old, going as slow as possible down this very slight hill, and she was terrified. She looked next to her, and the kids were flying by her, screaming and laughing, having a ball, falling down. They’re both experiencing the same thing. It’s just that the kids were looking at it differently than she was.

She said, ‘I was thinking of it as fear, and they we’re thinking of it as excitement, because it’s kind of the same feeling.’ It’s true. It’s like when I get scared, it’s more like, ‘You know what? This is exciting. I’m doing something I never thought I’d be doing, and I’m going to go into it head-on. Who knows what’s going to happen. I’ll survive it.’ I faced every fear that comes along, and it’s been pretty amazing.

My biggest fear growing up was the cancer, because there were people in family who died of it. I suddenly realized, ‘You know what? That’s even doable. I was able to fix that. If it comes back or something else happens, I’m going to face it head on and deal with it.’ You just face the fear and see where it takes you. I’m very happy with the way things are going.

Joseph: Is there something that you have learned about yourself through this process by finally pursuing this dream of starting your own shoe line?

Chris: I have changed so much. It is unbelievable. I used to actually be timid about all these kind of stuff.

Again, being authentic is awesome. I mean all you can do is be yourself. What you want matters. You can achieve anything as long as you just keep on doing it. Sometimes, you have to figure out different ways of doing it. I’m tremendously much more resilient than I was. I’ve become much braver at all these things. I’ve become much more flexible, and I’m seeing things in a really different light. When someone says no to me I’ll just figure out another way to do it.

Joseph: When you look back on your process of changing careers, given all these ways that you have evolved in terms of resilience and bravery, when you think back to when you were just toying with the idea of starting your own shoe line, what’s something that you wished you had known at that time that you now know?

Chris: I wish I’d known that everything’s always going to be all right, that you’ll get through anything. You’re smart enough and capable enough to deal with anything that comes along. Nothing is so big that you can’t handle it.

Back then I just thought this isn’t a possible journey to take on, when in reality, it really wasn’t. Now that I look back, that would’ve helped me a lot.

Another thing that’s really important: surround yourself with supportive people and people who are honest and who tell you the truth. You don’t want people who are going to just, ‘Oh, you’re wonderful. Blah blah blah.’ No, you need them to tell you the truth and be positive about it. Don’t surround yourself with negative people. That’s really important, because you don’t need to hear that kind of stuff. You need to be around honest, positive people who are going to support you and tell you what you need to hear.

Joseph: That’s a great tip, Chris. That’s something I’ve actually been thinking a lot about in my own life, maybe just because I’m becoming a little bit busier. My life’s a little fuller. I’m just making a conscious choice to decide who, not deserve to be in my life, but who I want to have in my life, and who I think adds something positive to my life instead of draining me all the time. I’ve been actually thinking a lot about that.

Chris: You don’t need anybody who’s going to drain. That’s awful. When I first decided that this was kind of a journey I was going to go on, my husband said, ‘We’ll sell the house if we have to.’ It always chokes me up. It’s like, ‘You’re totally all in. You’re willing to change your life to let me follow this dream.’

People like that, those are the kind of people you want.

Joseph: I want to wrap up, Chris, by talking about what you’re doing now. It sounds like you landed your first project. Can you tell me a little bit more about your first shoe line? You talked a little about the style, but can you just describe it in a little bit more detail?

Chris: To me, the foot doesn’t have to still be in a shape of a foot. You can take it, and there are no rules. I want to bring that to my lines. I want you always to look at my shoe lines and go, ‘Oh, that’s really different,’ or I always want you to know, ‘Oh, that must be a Chris Donovan.’ I love pushing the limits on what a shoe could be and just do all sorts of crazy things.

I also know that if you want to have a shoe line, you have to make it so that it will be wearable. People are going to see some of my stuff and go, ‘Oh, we have to go check them out in the store.’ They’re not necessarily going to buy my most outrageous designs. They’re going to want to still share in my designs, but they want to wear a flat or a little heel. I’ve got to take my ideas and filter them in such a way that they still speak of who I am but also make them practical for work or for everyday use.

I’ve learned a lot. I’ve changed. It’s interesting. You also have to know machines, how do they make these in the machines. There’s a lot of rules where seams can go and all sorts of stuff when I’m drawing I wasn’t thinking of, but I’m learning all that now.

Joseph: I have to say, in looking at your shoes, at least the ones that I’ve seen just online, they are absolutely distinctive and very unique. Chris, if people want to check out your shoe designs, where can they go to take a peak of them?

Chris: You can find me on Instagram as ChrisDonovanFootwear. I’m on Facebook, Chris Donovan Footwear. My website is also ChrisDonovanFootwear. You can see some of my stuff in all those different locations.

Joseph: We’ll definitely include all those links in the show notes. Again, I would recommend people to check them out. They are very cool and very surprising.

Chris, I just wanted to thank you so much for taking time out of your busy day to tell us little bit more about your life as a telephone repair guy formerly, and most recently, your journey to become a shoe designer and the lessons you’ve learned along the way. Congratulations again on landing your first project, and best of luck launching your first luxury shoe line.

Chris: Thank you, Joseph. I’m really excited.

About Joseph Liu

Joseph Liu is dedicated to helping people relaunch their careers and have more meaningful careers. As a public speaker, career consultant, and host of the Career Relaunch® podcast, he shares insights from relaunching global consumer brands to empower professionals to more effectively marketing their personal brands.

About Joseph Liu

Joseph Liu helps aspiring professionals relaunch their careers to do work that matters. As a keynote speaker, career & personal branding consultant, and host of the Career Relaunch podcast, his passion is helping people gain the clarity, confidence, and courage to pursue truly meaningful careers. Having gone through three major career changes himself, he now shares insights from building & relaunching global consumer brands to empower professionals and business owners to build & relaunch their personal brands.