Monica Holmes started her catering business in her home kitchen as a single mother seeking to provide for her family. From waiting tables at O’Charley’s to crafting her love for cooking into a 44+ year-old catering business that employs three generations of her family, learn about her tenacity, creative flair, and succession planning as she follows her wanderlust to travel the world.

How did you get started as a caterer? I was working in a restaurant and one of my girlfriends there … We both love to cook we would get together with a group of friends and you know maybe about once a month. We would all take turns and cook dinner at each other’s house and we would always have a theme like it would be Italian or Indian or whatever. I loved food and I was curious about it. I didn’t really know much about it, but we played around a lot just trying different things. Then a friend of hers who was in the film business asked her if she wanted to cater a dinner for a film crew and then they started calling us back and started telling other people about us and it just eventually, after about a year, grew into a business. We both quit our jobs waiting tables at the original O ‘Charley’s on 21st Avenue. That was a long time ago. She was married, got pregnant, had a baby. And then she decided that it was too much to cater with a baby and I was a single mom. My son was eight when I started. So, she quit I kept going and then It just kept growing a little bit more and a little bit more every year. Now, 44 and a half years later, it’s still here but a lot bigger than when I used to do it out of my house and load up my Toyota Celica with food and haul it around town.

Will you tell us about your roots – your desire for independence and your education?

Well, I ran away from home three days before my 16th birthday and got married. My parents, of course, were surprised. They did not know and they were not happy, but it really was the best thing for me to get out of there. I was a junior in high school when we got married and then since it was such a long time ago … they made me drop out midterm in my junior year. So, I did that, but then I went back my senior year and I graduated with my class in 1973 and, at graduation, I had a year-old child on my hip, my son Chris. I was married till I was about 20 and then I was not happy… I left and moved out and started over. That’s when I started working at the O’Charley’s. But before I did that, I was working, I was a makeup artist for Revlon. So, I had a whole other career. I had about 25 stores that I called on in Nashville and they wanted me to move to Arkansas and to be a rep and have like three states. But, I was a single mom. I had a young child and there was just no way I could move. So that job went away and I met a woman who was working at O’Charley’s and she told me she said, “You know, you could come work here.” She said, “It’s really fun and we make good money. So, I worked there for several years and I met some of the best friends of my life.

Has creativity always been at the root of what you do?

You know, I think that I’ve always had a creative side, but I think it’s just, it’s evolved as I’ve gotten older. And, you know, I look at what I do with catering. I mean, to me, it’s performance art … because … there’s many levels to it. You have to … not only do the food, but you have to think about how it looks and just kind of visualize the entire event and the energy… Hopefully, when I retire at the end of this year, I can … get back into doing pottery or try painting and just doing some different stuff that I don’t have time to do now.

Are risktaker and thrill seeker also part of the Monica Holmes trifecta?

I think I used to be more of a risktaker in my younger years. I’m getting a little more chicken as I get older, but I’ve always loved to travel… I can remember being a child and lying in bed and thinking about telling myself, “Okay, so when I grow up, I’m going to travel and I’m going to go places all by myself and nobody can tell me what to do.” And I can still remember nights just lying in bed and thinking about it. So as soon as I could start traveling, I did. And a lot of times for me, the only way I can escape my job, which is very stressful when I’m here working. When it’s on … it’s a lot. It’s stressful. So, you know, being able to leave for four or five days or sometimes a couple of weeks, you know, I can unplug even though I still have to check email. It’s really the only way that I can escape.

Don’t miss her story about a most unusual reunion she had with her sister while traveling.

How has dance served as a springboard for you at a different phase of your life?

I have taken dance since I was a child and, you know, from ballet to jazz to tap. I helped teach a children’s buck dancing class in Nashville several years ago. And really, I’ve taken about every kind of dance that you can imagine. You know, I’m not good at any of them. …I’m not taking any classes right now, but again, that’s another [thing], when I retire, I want to maybe go to Vienna or Argentina… I love the tango, I love the waltz, so I would like to go take some classes someplace exotic and learn how to do it.

We continue to talk about her sense of style that has become part of her signature. Her comment, “Your body is the perfect gallery” speaks volumes.

What advice would you offer to single mothers not only with respect to juggling but also following their dreams? It’s hard to follow a dream when you’re following a toddler but … it can be done you know. Single moms come in all different shapes and sizes and with varied support systems and I had some support from my ex-husband’s parents. They helped me so much. When I worked on the weekends they kept Chris. They were a very positive influence on him and really helped him become who he is because … I was a child with a child… I certainly don’t recommend having a child when you’re a child. It’s not the best, you know. It worked out for me. Single mothers just need to keep at it, keep plugging along and network where they can — for their jobs … it’s complicated.

It’s hard, but just live a good honest life and be open and let people help you where you can and hope it all comes together.

Do you have any advice for entrepreneurs today? Well, for me, when I got involved in some catering groups and I would go to conferences in Las Vegas with thousands of other caterers and sit in on sessions… I just learned so much. …I think when I finally got involved in some stuff like that … that’s when my company really started to take off because before that I was just making it up as I went along. I mean, I just was doing the best I could and I think getting involved in some organizations and with other caterers… I learned so much and that’s what really kind of took me to another level.

Do you have a mentor?

When I would go to those conferences there were some very large catering company owners that I met and I got to be friends with them. If I had any questions or issues, I could pick up a phone and call them. So, I did have several, and still I have people like that … because you’re always learning, even as long as I’ve done this … there are situations that come up that you go, “What the heck am I supposed to do now?” There’s a lot of social media chat rooms with caterers that we belong to. I’m looking at those daily and just seeing the struggles that only caterers [may face.] … There’s a lot of value in having those relationships with others in the business.

What is your favorite food to have on hand? – Cheese, always. Always good cheese. Preferably stinky cheese. And I love, when I go to Trader Joe’s, they have this Greek spiral phyllo thing. I think it’s a tiropita. I like to keep a couple of those in my freezer. And if I have somebody [visit] … I can pull it out and put it in the oven. You know, that’s always easy. And, of course, a bottle of wine.

Advice to your younger self?

Pay more attention to stuff. Maybe even keep a journal. Keep notes and Don’t be so hard on yourself too. You know, like just give yourself some grace, but stay focused and just being present. You just pay attention, you know, just don’t let your guard down.

Where do you find your sense of style? – I don’t know, that’s a hard question. You know, I just, I’ve always loved clothes and I used to collect vintage clothes … I would do clothes for videos. I would rent my vintage clothes out for a lot of the music videos back in the in the 1970s and 80s … I’ve sold thousands of pieces… I like so many different things and it’s just part of who I am. It’s in my, I guess it’s in my DNA.  

How do you stay cool under pressure — especially when you’re managing an event?

I think I appear to be calm. And I am for the most part, but I’m sort of in mama bear mode because when I’m on an event. I’m really watching everything and just making sure it’s all working and going the way it should be… And, when a client tells me that they’re nervous, I said, “you know, don’t, don’t be nervous. Let me, let me take that on.” You know, so I appear to be calm, but there’s always like a little fire in my belly, a little and sometimes kind of butterflies. It just depends on the event.

Tell us more about succession planning and why it’s an important step for you and for your son.

Chris was eight when I started catering and he was born in ’72, so he’s got a birthday coming up. He went to culinary school when Opryland had a three -year culinary program… He did that years ago… I baited him. I told him if he did the culinary program at Opryland that when he graduated he could come work at Clean Plate Club and that I would give him a percentage of the company. So, he graduated in 1999 and he’s been with me since 1999… Both of his sons — who are now 28 and 22 — work with us full-time and his wife Lisa is the office manager.  

Our conversation continues as we talk about the growth of her business, how it has become part of her identity and how succession planning and transition can be both challenging and healthy. In addition, we touch on the intergenerational (three generations of her family) in the catering business which is likely a bit of a novelty.

How do you suggest that others find the way to carpe diem and live life to the fullest? Well, travel, I think, is always a great avenue. Whether it’s international travel or — you know, if you’re not comfortable with that – [to] just to get out of your normal day-to-day thing… Go drive, even if it’s just three or four hours away to see some different stuff… Go to some museums … eat some different food and just see different sites and clear your head. I think travel is, in my opinion, is always medicine.

We [FiftyForward] believes that service [to older adults] is important, how might that ring true in your life?

It’s really important. I think in my younger years I didn’t even really realize that. But, you know as we age, we become more vulnerable ourselves. You really start thinking, oh gosh, I need to work on myself or work on things and just do better at being kinder to people and maybe dropping a card in the mail to someone… I try to do that with my mom, you know, like drop her a card if I’m on the road somewhere and it means a lot to people just to have a little acknowledgment.

What is one piece of advice that your parents or an older adult might have shared with you that at the time you thought was silly but now that phrase rings true in your everyday life?

I’ve had like my ex-in-laws you know, they were always, even though I divorced their son, you know, they were always very supportive and encouraging. And so I think it’s always those cards that you drop in the mail to someone, you know, words of encouragement to someone that have a lot of impact. And I just remember not always specific people, but I’ve had many people encourage me along the way … and it helps.

How do you squeeze the day?

I try to exercise every day if I can, like either do Pilates or I’ve started a rowing class lately … [and I] just try to stay in a positive space and take a nap if I am feeling not so good … or cranky or go for a walk.

But yeah, I just I’m grateful to be here and because I feel like you know at this point, you know, you’re sort of on borrowed time… I’m just happy to be here… I have my grandsons and now I have a great-granddaughter and [am] just enjoying life and looking forward to some more free time after I retire.

In this podcast, learn about her multi-faceted catering business that grew from a small operation using her home kitchen and deliveries with her Toyota Celica to 45 years later with a team of employees including three generations of her family and big trucks. This is a story about evolution, continuous learning, tenacity and zest for life.