From Corporate COO to General Contractor & Interior Designer, meet Kendra Roy who runs her own business in San Diego, California.
What would you do if you weren’t afraid of failing?
In this episode, we hear from Kendra Roy, an incredible interior designer and general contractor in San Diego, California, about her journey from working a stable job to starting her own business. She opens up about the real challenges she faced—especially in gaining respect as a woman in the construction world—and how building strong relationships became key to her success. Kendra also gets real about the fear and self-doubt that comes with leaving a secure role to chase a new venture and the importance of having a solid support system in place.
If you're considering a career change, Kendra’s advice is to take calculated risks and stay the course, even when things get tough. It's all about perseverance and trusting that you’re on the right path.
Episode Takeaways
Connect with Kendra
Jenny Dempsey (00:00.128)
It was in that moment when I was told essentially as this high producer that if I go on a vacation for seven days, I'm going to be fired. I was like, yeah, I think I'm done. Welcome to The Career Flipper, a weekly podcast all about career change stories from people in all kinds of industries. We talk about how they get from point A to point B and all the twists and turns in between.
If you've been thinking about switching careers, consider this your permission slip to go for it. I'm your host, Jennie Dempsey, a career flipper myself. After 18 years in customer service and experience leadership within the tech startup world, I got laid off and unexpectedly found myself flipping furniture, rescuing pieces that were headed for the trash and giving them a new life. Dressers, tables, you name it. I fixed it up and sold it.
You can check out my makeovers over on SanDigoFurnitureFlipper.com or SanDigoFurnitureFlipper on Instagram and TikTok, if you're into that sort of thing. I started this podcast because honestly, I felt really alone and a bit weird. Okay, a lot a bit weird about this career flip, but I posted on LinkedIn about it earlier this year and suddenly I'm talking to others, a lot of others who've made career changes too.
And it made me realize that it's never too late to switch lanes. And every conversation teaches me something new. So I figured if these stories are helping me feel a little more confident and a little less alone on my path, maybe they could help someone else too. So that's why I started The Career Flipper, to share these amazing journeys and offer support to anyone thinking about, in the middle of, or just past a career flip.
In this episode, you'll meet Kendra Roy, an incredible interior designer and general contractor in San Diego, California. You'll learn about her journey from working a stable corporate job to starting her own business. She opens up about the real challenges she faced, especially in gaining respect as a woman in the construction world and how building strong relationships became key to her success. Kendra also gets real about the fear and self-doubt that comes with leaving a secure role.
Jenny Dempsey (02:21.574)
to chase a new venture and the importance of having a solid support system in place. Let's get to the episode now. Hey Kendra. Hi Jenny, how are you? Hey, I'm good. Thank you so much for being here on the Career Flipper. I am so excited to have you share your story. We've been following each other on Instagram. I'm always in awe of all of the beautiful posts that you share, of the work that you do. So to have you here, bringing
how all this happened to life. I'm honored. Thank you. Thank you. And thank you for having me. I'm honored to be here and share kind of my career path and how let's stay conformed to where it is today. So tell everyone a little bit about what you do, who you are and all the things. Yeah. So I am a interior designer and general contractor.
So I have two sides of my company, which I started out was my general construction company, which is pretty rare for a woman to be a general contractor. But then also I have the interior design side of my company. So I do all of my own aesthetics, interiors, exteriors, and all that for all my projects and furniture, all that. So that's kind of what I do. I try to have it all in-house because I've learned that it eliminates
errors and it's what I'm good at. So yeah. And you're based out of San Diego, right? Yes. I'm based out of San Diego and been here for about 11 years now and I love it. So nice. Yeah. You can't beat it, right? We live in paradise. We do. So, all right, let's just get into it. Kendra, career flips. Tell, tell everyone about your career flips and the journey that got you to where you are today.
Yeah. So I don't even know first of all, how I got into kind of what I'm into. I was in college and I got my first gig in construction and also design. And I was in corporate America. I started off essentially kind of as an intern in college and I just busted my ass for lack of better term to work my way up within in corporate. So I very early on in my careers worked for REITs.
Jenny Dempsey (04:33.758)
developing and kind of designing for commercial spaces, malls, shopping centers, high rises, things like that. And it just kind of developed and evolved into what it was, which was developing and building all sorts of different types of construction. So I loved it and it was amazing. As I progressed in my career, I made my way up to COO of a corporate company.
that I had worked for for quite some time. And it was, you know, 12 hour days, you know, seven days a week. And it was the grind. I loved it, but I hated it because all the passion and all the projects I was doing, they weren't mine. Like, you know, I was building this company. I was building this portfolio, the clientele, all this, but it wasn't mine. And so about four-ish, five years ago,
I decided, actually it's been longer than that, man. Time flies. I started, I decided to leave corporate and, start my own company, which was probably the scariest thing I've ever done. yeah. Gosh. So yeah, so that's when I started my, my first company and I had absolutely kind of no idea what I was doing, to be honest with you. I, I was kind of flying by the seat of my pants and I was scared. And, know, I think the biggest thing, well,
The reason it is the scariest is the money, right? Is the money and also for me, was also the, can I actually do this? You know, I was kind of my harshest critic. I didn't think I had the confidence or I had the capability to do it on my own. I needed the man behind me, you know, to get the money, to get the jobs, to get the clientele. And I think that was the biggest thing, but money was obviously the scariest part of it, right? Which is, my God, if I, what if I don't get jobs and what if I don't have a source of income coming in and how do I keep it steady? And that was the biggest, scariest.
component of it. And then, you know, kind of, I don't want to say we were kind of lucky, I got my first complete new ground up house remodeled to design it and build it. And it was very exciting. Like I remember getting my first check, the deposit and I was like, Holy cow, like this is actually happening. So wow.
Jenny Dempsey (06:47.906)
When you were making that decision, you're working in corporate, you know, the 12 hour days, seven days a week, and you were feeling like, like this is just so much, it's not mine. What was that kind of decision making moment where you're like, no, I have to leave? Like what, what was going through your mind? Cause you knew it was like jumping into the deep end. You mentioned not sure if you could do it and there's the money thing, but you still did it. And that's like, what was it that made you still do it?
Well, there was an incident that occurred. I I had a pretty hostile work environment. You know, it just got to the point where it was just like, you know, it wasn't enjoyable anymore, right? But I actually, it was a work-life balance thing that came down to the wire for me. So I was supposed to go out on a trip. I mean, I never vacationed. I mean, I never did. And I remember I was, a trip I had planned forever, I was supposed to go. And essentially my boss at the time was like, you can't go, cancel it. If you go, you're fired. I mean, essentially.
And it was in that moment where I was like, you know what, this is not sustainable. You know, especially as I know later on in life, I want to have a family and actually have a work-life balance. It was in that moment when I was told essentially as, you know, this high producer that if I go on a vacation for seven days, I'm going to be fired. I was like, yeah, I think I'm done. Yeah.
And, I think the biggest thing that also like was kind of a moment is at the time I, you know, I was, seeing someone and, and, you know, he had his own company and he created his own work life balance of how many hours you work. Right. I think that everyone thinks you have to work these 12 hour days or you're not going to fulfill the task. Right. Or I remember when I first started my company, I was like, some days I'd work one hour and other days I'd work 12 hours. Right. And I had a really hard time understanding that like, you can actually produce.
just as much in a couple hours as you can, right? right. Yeah, so was really bad. was trying to figure out a work-life balance. Yeah, that makes so much sense. And that sounds like such a, I mean, it's a smart decision, working smarter and being able to take those breaks, whether they're a vacation, whether it's just a day to go around town or whatever it is and to be able to create that structure, that totally, totally makes sense. And so you made the decision and then
Jenny Dempsey (09:11.81)
You know, you're in it and you're feeling like you mentioned, you know, can I even do this? Like that kind of like almost imposter syndrome and just the self doubt coming up. Like, can you talk more about that? Because I feel like so many people listening will not make decisions simply because they may not believe in themselves or they may just be so held back by those self doubts that it's like, what will everyone else think type of stuff, you know?
you know, so I think for me, like again, it was, there was two things that were at play. One, I'd always been, had a security blanket, right? When you work at a corporate job, like I said, you have a security blanket, you know, when you're getting paid, how much you're getting paid in the security blanket, right? And so when you transition where essentially, you know, you eat what you kill, that's, that's the first part, right? But also what was a big scary thing for me was just also all like the public social media stuff.
And it still actually gets to me to this day where I'm like, but that designer is better than I am, or that general contractor is a man and he's been in the industry for 25 years. Why would somebody hire me? And so it's actually even funny, I still have self doubts about my ability to do something when you see other people's product or whatever, and it's hard to not do this comparison analysis.
But then at the end of the day, have to remember like, I am a package and I'm selling myself to clients and I stand behind my work ethic, right? And the quality that I deliver and also just kind of, you know, who and what I am. So I have to always like remind myself that, that I am, you know? Yeah. Yeah. It's so hard to not do that. my gosh. I feel like I understand that like furniture flipping like, you know, I've been doing this.
maybe year and a half, almost two years now. And so, and I look at all these other people on Instagram doing the same things and I'm like, theirs looks so good. And I look at mine and I'm like, it looks good, but then I zoom in and I'm focusing on all the little imperfections and I'm like, no, it's not as good as theirs. And then I'm like, maybe I shouldn't be doing this. And you just kind of go down this rabbit hole. But I like how you mentioned, that doesn't necessarily go away. You're constantly working on it and having those conversations with yourself.
Jenny Dempsey (11:31.458)
to show like you're doing amazing work and you just gotta keep kind of going on even though those voices are there. Yeah, I know. mean, it's, you know, I think one of the biggest struggles is that I had in through the course of my career is more on the construction side, you know, too, is that as a woman in the industry of construction, right? It's I have learned that you can't demand respect, right? And a lot of these guys are kind of like, you're a girl. You don't know what you're talking about. And I don't mean to call that part out.
But in construction, there's just very few women who are general contractors or in construction. so I've really had to learn how to, I guess, listen and gain respect within the industries. And it's all about relationships. Right. I mean, it is all about relationships in both industries, the interior design world, know, distributors, manufacturers, I mean, everything. And that's the biggest thing. And actually advice I'd probably give anybody is that.
is as you enter in any career, it's all about relationships, the building of them, right? And the trust factor. I mean, that is really the biggest thing I think that I've learned or that has helped me in my career. Gosh, it's so, it's so important. So true. And it really like, it strengthens those relationships. You learn something from someone you have, like your people, like I know someone and I trust them to do good work and they trust me to do good work. And the power of that is like, it's incredible. Like,
Yeah, it is. absolutely is. Because even with what you're doing, if I buy pieces from you, have to know when they're arriving at my site, they're exactly with how I've described them. And they're so, like I said, it's for humans at the end of the day. there's always going to be errors. so I guess, again, what I've had to teach myself is that I've made so many mistakes, so, so many mistakes between contracts.
or design or construction. I, with each every time, I'm like, okay, I've made the mistake. Yeah. I'll it again. Right. And so you learn. But, during those mistakes, I mean, it kind of gets hard to be like, ugh, I'm giving up. Like crap. know? But that's actually how I continue to learn and evolve. Right. So.
Jenny Dempsey (13:44.024)
No, totally. I feel like sometimes I will just take pieces of furniture and just work on them to make those mistakes because I want to make sure that when I'm doing something for an actual client that it's like, that doesn't necessarily happen for that. It will and it has, and I always own it. I think there's also that too. Owning that and really like, yeah, I did this and I'm going to do better next time and I will make up for blah, blah, all the things. yeah, no, that's such a big, a big part of it. Accountability and
Yeah, sometimes it goes beyond just the actual work, like, but the people, like, are they punctual? Are they, do they say what they're going to do? Do they deliver on their promises? I mean, building those relationships is so, so crucial. I love that you brought that up. No, I mean, and that's why I brought it up because it is because, you know, I do believe that in almost any industry, whether you're on your own or whatever, you still have to rely on other people, vendors, suppliers.
And so it's just, it's crucial, you know, to, you know, time is money and what have you in any job, right? And so I think it's just having your network, your group and what have you. So, yeah. absolutely. Absolutely. And then, you know, kind of shifting just a little bit to another thing that you mentioned was the money thing. And this is, this resonates so much with me too, cause it's kind of, I mean, if you, especially in San Diego, like it's so expensive. So if you don't,
If you're going to do this unconventional path and start your own thing and carve it out, not having the money like you have with the stable paycheck is really scary. It's so scary. I know that holds so many people back. for myself, I got laid off and couldn't find anything again. And so it was terrifying. my gosh, even if I wanted to.
you know, and then the timing wasn't good. I applied at a coffee shop, but it's schooled out. And so all the jobs are being taken right now. So it's just like not having that is so frightening, but having kind of making these calculated risks when doing these decisions. think sometimes like I know with furniture flipping and maybe you could speak to this for your own. Like, you know, I knew how much I had in that kind of like safety bubble that I created and saved for.
Jenny Dempsey (15:57.87)
And so I was able to make decisions based on that and set kind of some goals and timeframes around that a little more calculated risk. And it made me feel, well, it still makes me feel a little bit, I don't want to say better, but like, you know, a little bit more supported. And so I'm wondering, like, when you were kind of navigating that early on, how did you keep going, you know, even though it was bright full and not having that regular paycheck and kind of unraveling from that kind of stability and almost scarcity mindset?
You know, it's so originally going into it. I, you know, was kind of like I said, shooting from the hip. And I what I realized after I just like was doing as much as I could, which was networking and talking to people and trying to, you know, just get a clientele. And one of the things I kind of actually made a mistake on early on was I thought that to start my company, I had to have all these like accessories like this fancy website and hats and shirts and all this stuff, business cards and like all these accessories.
to kind of prove that I was a company or I was someone. And so I got into office way too prematurely. And so I think I made a lot of errors and mistakes when I first started my company thinking I needed all the tangible items when really what I actually just needed was me out in the public eye meeting with potential new clients. And so I kind of made some mistakes there when I drained that bucket of money, you know? And then so what I then had to figure out was, okay,
I got to go grind, right? So I got to go and actually get clients, right? Because now I have all these tangible things, but I don't have the clients, right? And so I made a mistake there, which I would not have done if I knew what I knew now. Because I just, know, like, again, I don't think, I think that a lot of people, they're going to hire you for you, right? And for what you're going to provide. And, and, you know, I also think that you have to mesh with whomever you're going to be working with, right?
personalities, but it was scary. So, you know, I was spending money and some money wasn't coming in. And so I had to literally just grind. And so I started a couple of projects and, it was very early on. I actually got burned on one of my projects by one of my contractors and I probably lost 20, $25,000. And I was ready to call it. I mean, I was like, done. Like, I can't do this. Right. And honestly, like what kept me going was just.
Jenny Dempsey (18:20.322)
you friends and family being like, got this, like get back up and figure it out. But yeah, I mean, there's been many times in my career. I'm like, can't, I can't do this. It's scary. And, and, and I, like I said, when I, when I had a contract or screw me over early on, I mean, I was, I was done. So it was, so yeah, you just, I mean, it was just really just, I love what I do. And I knew that I could keep persevering. I just had to like, get out of my head. Yeah.
my gosh. no, that totally resonates. And something that I hear when I've been talking to others and similar or different career paths, the one thing that comes up is like, is this real? Is this a real job? And so when I heard you say, you know, kind of, you know, whether it's the fancy website or, you know, the swag or business cards, I'm wondering if there was, was there anything like that where it was like you wanted it to be more, like you needed it to feel more real than,
maybe it felt at the time. even know with like furniture flipping sometimes I'm like, is this a real job? Like, can I actually do this? I question it probably more than I should, but like sometimes it just feels like maybe I do need more things that really prove that I'm, you know, able to do this, but really what you said, they only want you, like they want you and how you show up and what you bring to the table. Cause you do it like nobody else.
and you bring your own unique spin and sparkle to it. And I think that remembering that, you don't need business card, you don't need this, because people are going to remember you for you. I mean, that's exactly it. And I still have to remind myself that, you know, and like I said, what I want, the other thing I've also learned is as I've gone through the careers, when clients are interviewing me, I'm interviewing them just as much now, right? And that because otherwise you can get into a situation where it's like, this is like I said, it's just not a good.
fit. so I guess that also helps me know that like, they're hiring me, right? And I don't need all this swag, as you said. And but it's still it makes it makes you with your confidence feel like you're more credible. You're more legit. You're you know, you're you're as equal as the big guys, right? And totally. Totally. No, I guess.
Jenny Dempsey (20:35.918)
And the other thing you said that really stood out, you the support of family and friends. Like you talked about, you know, networking for business, but I think there's something so crucial about also having that support system of family and friends that are cheering you on, you know, rooting for you. I feel that too. I'm like, I couldn't have done this without the support of my partner, of my friends, of my family, of my dog. Like, you know, like just everything kind of coming together into this full community of support.
personally and professionally. I mean, do you feel that same way too? Like how important to have that, that support system? 100%. I mean, if it wasn't for my husband, I like don't, you know, I think there was many times I probably would have given up and, and, you know, he's my biggest fan and cheerleader and supporter. And it is also hard because, you know, with owning your own business, you know, there's so many pros and cons. And I have to remember just like with any job is like, okay, I got to shut it off.
Right? But the problem is, is again, as a business owner, sometimes you can't. And so it's just finding a balance. But yes, it's, you know, having a support system, especially to get through the first couple of years is absolutely crucial because you need someone to talk to you. You need someone to, you know, yell and and be like, my gosh. Right. Yes. Exactly. Those moments when you're like, what is this person talking about or what did I do? I can't believe I did this.
just throwing ideas around like, do think of this one? Is this or these colors or I don't know. Like, my gosh. The idea bouncing 100%. I mean, it it very much is. And it's also like to know that you get opinions, right? And to kind of help better whatever it is that you're doing. Totally. I like I said, I stout my designs.
all the time. I'm like, my God, is this going to come together the way I envision it? mean, my deepest thinking hours, 3am. I wake up and I'm like, have an idea. my God. Okay. That's so fun. I literally just wrote like a blog post about the 3am. What is it about 3am? It's the same thing. I'll wake up like wide awake with like these ideas. Honestly, that is how this podcast came to life. It was like probably like, I don't know, maybe like 314 in the morning. And I was like, my gosh, this idea. What in the world?
Jenny Dempsey (22:53.334)
like, yeah, I don't know. I wish I could tell you it's like, my witching hour and it is it's a real thing. mean, I wake up and I have all these ideas like, I should have done that or no, I should do that or you know, and I don't know. Yeah, it's so it's so wacky. It's so wacky. No. So so you're on you know, you are working with clients and you are doing you know, all it sounds like all different sizes of projects, you know, from contracting to interior design, how do you kind of
juggle both of the worlds? they're, they are, I mean, they're in the same under the same roof, but they sound also very different. And so when you have your own business, sometimes we, we do things that are maybe a little different. Like for example, I'm doing furniture filming, but I'm also podcasting. They're very different worlds, tech and you know, in the garage, cupboard and paint. And so how do you kind of navigate both worlds under, you know, it together and, and do that.
So my interior design side of my company is what I'm really trying to grow right now. That's when I just started. So it's a second tier company. And that's what I'm really trying to develop and grow. I've been doing it forever, but I never really marketed it. And they're two completely different worlds. They work together, but they don't really. So typically, you know, the construction is the dirty, ugly, and everybody hates it. But then everybody loves all the pretty stuff, right?
And kind of the way that it came about how it has now evolved is I was designing all my projects, but I just wasn't getting paid for it. Yeah. Right. So I would, I would have, you know, a client call them, you know, I'd be doing their construction and it's like, well, what do I do? I don't know. Where do I put this and what do I do? You know, and it kind of was like, well, let me just do it. I know how to do it. Right. From, from the, the, from designing layouts to the architectures to.
all the entitlement process to then going into construction and then being like every client, especially in residential is like, well, I don't know what time.
Jenny Dempsey (24:51.95)
paint colors. And so then I was doing it and I loved it so much. And I'm like, why am I not doing it all in house? Because what was happening was, is they would hire someone else, a designer, right? And I would have to work with the designer. And a lot of times, and this is no offense to any designers, designers don't understand construction. And so a designer would be like, I want to move that wall.
Well, you can't just move that wall. There is a load bearing wall. There's a header. And so the things that, know, again, it kind of evolved was, is I know construction and I know how to kind of help clients value engineer their projects. Cause you know, designers can design beautiful, pretty spaces, but there's also costs that go behind it. And so with the different type of clientele, you know, I really try to work with them to build what they actually want me based off budget and also aesthetics and also, you know,
whatever, right? So I don't have that sense. Yeah. But so I kind of wear two different hats. I wear my my my pretty interior designer hat, right, where I get to dress up and wear high heels. And then I wear my I'm in the field like I am right now. I just went to Home Depot and got bags of concrete for my guys. So it's very polar opposite roles. And I, you I love it, though. So yeah.
I love that. That's such a, that's a fun variety of things. That's, that's so cool. And I'm curious, so like where you're at today, if you had some advice for, you know, yourself when you were still in that corporate job and you were, you know, not able to take that vacation, is there something that you would have told yourself then that you know now? you know, I think the biggest thing would be is to have, if you start to have any doubts, you know, about
what you're doing and you have a dream or an aspiration is to not hold out on it and just take the risk. Be calculated with your risk. But really go for it or come up with a plan. Come up with a plan to understand what would it look like? And that would be the biggest thing is it's just that. mean, it's just really is to, if you are...
Jenny Dempsey (27:08.662)
If you are unhappy with what you're doing or you have this big, big, bold dream or goal or idea, like go with it. Figure out how to make it work. Because if it's meant to be, like you will figure out a way and you know, we're us as humans are very resilient and you know, you'll figure it out. Right. So I guess that's my, my two cents on that. Yeah, no, that's so, it's so inspiring. And it's so hard sometimes to remember that when you're in the hustle and bustle of all the things and
you know, got projects in your plate and can't take a vacation. And I think when we have the opportunity to hear, you know, people like you sharing this, we have an opportunity to step back and be like, yeah, no, I'm not gonna let go of this dream. not, you know, I can be smart about it and still take the risk. Like I have a friend right now who she's burnt out from her job and her kids are about to go to college. And she's like, I'm gonna make a plan. Like I have my...
you know, two year plan where I'm taking, she wants to be a photographer, but she can't just leave her job to do that with kids in college. So she's taking a class now, you know, in the evenings. And then eventually, you know, she's going to phase into it. And I'm just like, I think there are ways to make things happen on scales that we are, that are the calculated risks, just like what you said. Like, I think that's so important, but yeah.
Thank you so much Kendra for, just, feel so inspired by you, you know, for the work that you do in this industry and for, you know, you just being so bold and creative with what you do. And I want people to be able to connect with you, to see your work, to, you know, if they have questions or honestly, if they're in San Diego to hire you, like how can people find you? How can people connect with you?
So I'm on Instagram with Kendra Roy Designs and also on my website with KendraRoyDesigns.com. And yeah, I would love to connect with anyone listening and would love to work with you. So. Thank you so much for taking the time. Thank you Kendra. appreciate it. It was great talking to you. Thanks for tuning in to this episode of the Career Flipper. Be sure to connect with Kendra using the links in the show notes. If this episode hit home for you.
Jenny Dempsey (29:20.716)
Like if you've ever found yourself banging your head against the wall, stuck in a job that drains you, but scared to make a change? Share it with a friend who's feeling the same. I get it. We all hit those moments where we're exhausted, unsure, and questioning if we really can make a big leap. Reading and viewing the show is such a small action, but it makes a huge difference, and subscribing means you'll get more real stories like Kendra's every week.
Your support helps me reach more people who are right on the edge of making their own brave move and need just a bit more courage to lead. You know, before I got laid off, I spent years in customer experience leadership, helping companies and teams refine how they support customers. That journey didn't just end with my job. It has impacted over 12,000 students worldwide through the online courses that I've created before I got laid off.
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What I love most about doing this podcast is knowing that maybe, just maybe, it'll nudge you or someone you know who's feeling stuck to finally take that leap toward their dreams. I know the fear of the unknown can be paralyzing, trust me I know, I'm right there with you, and it's really tough to take that first step when you're not sure if things are even going to work out. But if I can ask one thing.
It would be to put your shoes on, take that shaky but brave first step, and just see where it leads. You don't have to have it all figured out right now, and the truth is, none of us do when we start. Just know that it's possible, and I believe in you. I really do. So keep on your path, my friend. What's the best that could happen?