Greenwich, Westport, Scarsdale


Meet Lisa Cassella, 51, who’s had the courage to reinvent her life and career when things weren’t working—and more importantly, not making her happy. She’s found her bliss with a career in real estate, but it didn’t happen overnight. Daily gratitude, trips outside her comfort zone, inspiring mantras and a little bit of disco give her the confidence she needs to live her life with zest and purpose.

Here’s what she did to get there and what you can borrow from her positive mindset in your own life!

Set the Tone Each Day

“I feel most competent and successful when I'm doing something that I love. I'm probably the most successful and confident in the morning because my day hasn't started, so I get up and read something inspirational. I write down some affirmations and what I'm grateful for. It’s hard to think about something different every day that's you're grateful for. But throughout my life, I've had to reinvent myself a few times and it took me a while to figure out what I wanted to do. The last year I've been doing real estate, and it's for me. I really love doing it—it gets me up in the morning, it's exciting, and it's fun. I don't mind working basically 24/7 because it makes me feel good.”

Live in Abundance

“In real estate, if you're doing a deal and it falls apart, you don't feel very successful. You don't feel like you negotiated it well or, you just feel like you did something wrong—even though, you might not have done anything wrong at all. I just try to live in a world of abundance, not scarcity and remind myself there's another deal out there, I did the best that I could, and I just have to move on from it.”

Why a Smile is Your Best Accessory

“Confidence to me feels like walking on air. You're just confident. It's like wearing your favorite outfit and knowing you look fabulous. It's euphoric. It's feels good. For me, I try to wear a constant smile on my face. I may look crazy to some people, but even if I'm not feeling good on the outside, the least I could do is smile at someone and say, ‘Good morning’ or ‘How are you today?”

Attitude is Everything

“My best confidence role model is my best friend who has battled breast cancer twice now. She just turned 50 last year and she never once felt sorry for herself. It was never about her cancer. Even when I went out to visit her shortly after she had surgery, she was still so positive and had the right mindset. She persevered and moved forward and didn't dwell. I love that she's strong—and she's also the first person that tells me when I'm wrong—which I love that.”

Everybody Makes Mistakes—And That’s Okay

“My confidence boosting pep talks sound like, ‘You can do this.’ I think about times that were tough in my life that I've overcome and ended up better on the other end. Everybody makes mistakes. I've learned that if something happened that doesn't make me feel good, I’m allowed a couple of minutes to dwell on it. And then I'm like, ‘I'm going to move on because I've felt it.’ I find myself doing that a lot. Even with parenting, I’m like, ‘Should I have done that?’ You feel bad about something that you might've said to your child. You're thinking about the therapy bills 20 years from now. But then it’s like, ‘I can't dwell on that. I just have to feel it, feel bad about it and move forward.”

Trusting Your Instincts

‘“I always think of Maya Angelou’s quote, ‘When someone shows you who they are, believe them the first time.’ It reminds me to trust my instincts. I think women especially will second guess themselves—I know I do. It’s nice to be reminded that certain things are out of your control. That you need to trust your instincts and believe in yourself and what you're seeing. And that you can't change anyone. That something are just not in your control.”

Playlist Bliss

“I listen to a lot of Prince, and a lot of George Michael, and a lot of disco. There's not an unhappy disco song. It’s all about making love, and dancing the night away, hanging out with your friends, and the party that's happening, and the good times. That's what I listen to if I'm going to work or meeting a new client. I put on my disco playlist. I mean it sounds kind of corny when I say it, but I'm 51 years old. I had older cousins that loved disco in 1978. And so, it also reminds me of being happy as a kid.”

The Power of Reinvention

“I've always had the ability to reinvent myself when something's not working. If a career is not going in the right direction, I've had to move on. I think women my age, have had to reinvent themselves a couple of times. Whether they took their time out in the workforce to have children, or to care for an elderly parent. Then they try to go back in, and maybe it's just not the right fit anymore. I think that my willingness to try something new, even though I'm scared about it is a good quality. It makes me unique. Not everybody's willing to go out and take a boxing class even though they've never hit anything before. And it was terrifying, and it was awful. But it's been like three months now and I love it and I cannot wait until Friday when I get there. I feel challenged by doing something that I haven't done before. I was doing kickboxing, but then I realized that my knees hurt too bad. I couldn't do it anymore, so I tried regular boxing. I had to push myself to get there. I'm wasn’t 100% comfortable with it. But I’ve bought and sold many properties because my husband's a contractor and we flipped houses for a couple of years. The first flip is really hard. And then the second flip is easier, and the third flip is even easier than that. And it's just continuing to do something even though it's challenging.”

Who Says You Have to be Perfect?

“I'm very much a creature of habit and I really like to be comfortable. But this year, part of my resolution, was to push myself out of my comfort zone. In real estate, you have to touch base with people, you have to make phone calls. I don't like making phone calls, but I do it. I write handwritten letters and notes to people. Thank you letters after they meet with me. I make lists and notes to myself to make sure I do this today or remind myself to be grateful for my family. You don't have to be perfect. Just because you do something, it doesn't have to be 100% perfect. You're going to make mistakes. And a mistake doesn't matter. It's how you handle it, how you get up from it. I really have to remember that.”