S2 Ep24. Law, Love and Authentic Living: Kimberley Caines-Best’s Story

In this heartfelt episode, Aderonke Bademosi Wilson welcomes Kimberley Caines-Best, lawyer, wife, parent and dedicated gratitude practitioner for a rich and inspiring conversation. Kimberley opens up about her journey from dreaming of becoming a lawyer as a young girl to becoming a powerful force in her community. Through her thoughtful reflections, she shares the transformative power of gratitude, the value of stepping outside your comfort zone and the magic that unfolds when women uplift one another.

The conversation begins with Kimberley exploring how her most cherished roles wife and parent shape her daily life and sense of self. She offers insight into the challenges and joys of being a biological and step-parent, and the personal evolution that comes with nurturing a blended family.

As the discussion unfolds, Kimberley takes us back to her early passion for law, sparked by an essay she wrote at just six years old. From there, she walks us through her professional path, from practicing civil litigation to serving as in-house counsel. Along the way, she reflects on her studies in the UK, what keeps her motivated in her career, and the deep sense of purpose she finds in her legal work.

Grounding her busy life is a heartfelt commitment to daily gratitude. Kimberley shares her personal rituals, from jotting down moments of thankfulness in her planner to filling a good things jar throughout the year. A practice that serves as a gentle reminder to pause and appreciate life’s big and small blessings.

Listeners will also enjoy learning a few delightful surprises about Kimberley. She has a fondness for diners and comfort food from around the world, a quirky fear of iguanas (which she amusingly likens to public speaking), and a deep love for musical theater complete with performances in local productions and a cherished family tradition of music.

When asked about her proudest accomplishment, Kimberley’s answer is heartfelt and immediate: her daughter. She speaks candidly about the powerful lessons she’s learned through motherhood and the pride she feels in watching her daughter grow.

The episode wraps with a look at Kimberley’s efforts to make a lasting impact. From founding the Women’s Legal Network to creating a support group for stepmoms in Bermuda, she emphasizes the importance of building spaces where women can feel safe, supported and empowered.

Throughout the conversation, Kimberley returns to key themes of vulnerability, honesty and courage. She encourages listeners to trust their instincts, address unmet needs, and take bold steps to foster connection and community, reminding us all that growth often begins just beyond our comfort zone.

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Transcript

Aderonke Bademosi Wilson (00:01.366)
Welcome to another edition of ABWilson's Heart of the Matter, a podcast that uses overwhelmingly positive questions to learn about our guests, where every episode uncovers extraordinary stories of triumph, growth, and empowerment. Hi, I'm Aderonke Bademosi Wilson. My guest on today's show is Kimberley Caines-Best. Kimberley is a wife, parent, lawyer, and grateful. Kimberley, welcome to the show.

Kimberley Caines-Best (00:37.324)
Thank you. Good morning, Aderonke. This is awesome. Thank you for having me.

Aderonke Bademosi Wilson (00:42.188)
Well, thank you. Well, let me just say thank you for saying yes. And I never take for granted when people say yes to being on the show. So thank you for saying yes and carving time to be on the show. So, Kim, I want to start with your first two descriptors, wife, parent. What does that look like for you?

Kimberley Caines-Best (01:10.358)
Yeah, that's a great question. First, it's very different sitting in this seat on a podcast. I listen to a lot of podcasts, so being the listener is very different from being the interviewee. But yeah, I just appreciate you creating this space. When the query of three words, it was really hard to reduce myself to three words, and I really wrestled with, do I use the words that describe what I do or who I am. And wife and parent are two roles that I'm leading my life with at the moment. I'm a biological parent, but also a step parent, which has been a journey for me over the last decade. And it's been a space where I've grown a lot. And so I really thought it was important to highlight those words of wife and parent for your audience.

Aderonke Bademosi Wilson (02:09.582)
Hmm. And tell me about being a lawyer. Do you enjoy it? And I've interviewed quite a number of lawyers or just even talked to lawyers and many have changed professions, like the former lawyers. So tell me what brings you a spark about being a lawyer.

Kimberley Caines-Best (02:24.604)
I love that. I was one of those people that at six years old wrote that I wanted to be a lawyer. And I wrote an essay when I was in school in the second grade. To this day, my mom still has that essay. And I guess it was a North Star for my professional journey. And when I got called to the Bermuda Bar, my mom had it framed and it hung in my office for many years at my first firm.

So I always wanted to be a lawyer. I had an image of what a lawyer was, but through exposure and professional experience opportunities, learned that there are different types of lawyers. So my journey has evolved over the last 15 years. So I started as a litigator, primarily to help people in my community. I was a civil litigator. And then as my career trajectory unfolded, pivoted into an in-house role, so lawyer for a company and I've had the opportunity to work for two companies as in-house counsel, which has been really rewarding. But I love the ability to be presented with a problem and find a solution, whether it be for clients or business partners. I use a lot of skills that just come naturally to me. I'm quite inquisitive, curious. I ask a lot of questions, but I also like the challenge of reconciling the law with a situation. And it's hard to believe it's been 15 years. I moved back to Bermuda in 2010, and here we are in 2025, but grateful for the professional journey that I've had today. But yeah, I was one of those kind of, I wanna be a lawyer when I grow up, and never really deviated from that goal.

Aderonke Bademosi Wilson (04:21.974)
Congratulations. I think that shows your clarity as a child, even if you may not have known all the facets of what being a lawyer looked like or what it meant. You stayed on that path. And not a lot of people can say that actually.

Kimberley Caines-Best (04:40.491)
Thank you. I wondered at times if it was too restrictive for me. I did consider other opportunities, but when I, I guess, resolved within myself what I wanted my professional journey to be, it was being a lawyer. And you're correct, I learned a lot of different things along the way and had the opportunity to study in the UK, which was such an enlightening experience. I know we have a shared love of the UK and London in particular. It was, yeah, it's been a great, great journey, not without its own challenges, but it's been one, it's been a good journey.

Aderonke Bademosi Wilson (05:15.158)
And the third word you used as a descriptor was grateful. Tell me about that.

Kimberley Caines-Best (05:22.741)
I'm in a place of gratitude and it is a posture that I try to maintain on a daily basis. I do have a practice of gratitude and I've particularly had to hold onto that heart posture for coming out of what's been a pretty challenging time personally. And I guess the lesson for me has been that there is always something to be grateful for even when life isn't going as planned or as expected.

And so when you're on those mountain tops and life is great, it's easy to list off the things that you can be grateful for. But when you're in those valley moments, when life is life-ing, it's a lot harder to find things to be grateful for, but there are things. And so I just want to continually be reminded of the things that I have, tangible and intangible, that I'm grateful for. So that was the reason for the word.

Aderonke Bademosi Wilson (06:21.11)
And you said you have a practice of gratitude. Tell me about that please.

Kimberley Caines-Best (06:25.685)
Yeah, I will note daily items or things or conversations or people or experiences that I'm just grateful for. It can range from this conversation will go on my list for today, but it could also be a beautiful sunset or it can be waking up or being able to move my body. There's a whole spectrum of things to be grateful for, but it's simple. There isn't much magic to it. I know that there are books and journals that you can use that have prompts, but for me, it's just a part of my planner, which I, at the end of the year, will look back and reflect. I also have a practice where I keep a jar on my kitchen table of one good thing that happened during the week. And at the end of the year, New Year's Eve or New Year's Day of the following year, I sit down, put all of the cards in chronological order, and review the good things that have happened.

And it's a great reminder, because as much as I'd like to remember what happened on February the 25th, I can't as I age. And it's become a practice that I've employed for the last few years. And it's such a great, great opportunity to feel like, yeah, this year was challenging, but there were still silver linings and there were still moments that sparked joy for me.

Aderonke Bademosi Wilson (07:45.602)
And what do you do with the cards afterwards? Do you keep them?

Kimberley Caines-Best (07:48.477)
I keep them in my night table drawer. I put them all together, they're little index cards and I put a clip on them and I just keep them in my night table drawer.

Aderonke Bademosi Wilson (07:57.87)
Mmm, that sounds wonderful.

Kimberley Caines-Best (08:00.044)
Thanks.

Aderonke Bademosi Wilson (08:04.814)
Kimberley, I would like our listeners to learn even more about you. Please share three interesting things about yourself that our listeners may not know and friends will be surprised to learn.

Kimberley Caines-Best (08:19.167)
I love this question. As one who asks questions as part of her career, I love when people ask me questions. So when I saw this question, I was like, yes. So the first thing is I love diners, which I think some people might be surprised to hear. I love just going into a diner and I've been to diners all across the States and here in Bermuda and around the world. And there's just something comforting about going into a diner. So I love diners. There's one near my husband's parents' house in New York. Whenever we visit, I'm like, we have to go to the diner. So I love diners, milkshakes, that comfort food. So I think I realized there's just something just really authentic about a diner. No pretense. You just get to go in, be yourself. So I love going to diners. The second thing is I am absolutely petrified of iguanas. Those close to me know that. Yeah, I don't know what it is about that particular reptile species, but I am scared of iguanas. I backpacked through South America in my second year of university. And I remember we were walking into this park and it was full of iguanas in trees, on the ground, like, really, really long iguanas and just had a moment of sheer panic. Like I could not bring myself to go in and this is like 20 years ago. So I am not a fan of reptiles. So I just do not like iguanas. And I actually in a talk compared that fear to the fear of public speaking, that we all have fears of some sort and how to overcome them. But I don't necessarily think I've overcome that fear yet.

And then the third thing is if I could choose an alternate career, as much as I love being a lawyer, I would love to be a Broadway actress. I think there's just something magical about bringing joy to people. And so to fan that flame of desire, I've done two musicals here locally with the performing arts charity Troika. Once on this Island and Beauty and the Beast, again, many years ago. And it was just so fulfilling to actually, you know, have the rush of the performance and hear the buzz of the audience and singing. And what's really cool is my first foray into musicals was Annie and my daughter has her current love is Annie. So it's been nice to kind of have that shared love of that musical with her. But I would love to be a Broadway actress in some form or fashion.

Aderonke Bademosi Wilson (11:10.446)
So are you a singer? Do you have a singing voice?

Kimberley Caines-Best (11:14.131)
I do, but I'm not going to sing right now, but I do. I come from a pretty musical family, so I do sing. I also play the violin. Yeah.

Aderonke Bademosi Wilson (11:25.75)
Okay, wow, I definitely did not know that. Wow, thank you for sharing. Thank you.

Kimberley Caines-Best (11:30.497)
No worries.

Aderonke Bademosi Wilson (11:35.416)
Kimberley, can you tell us about a recent accomplishment or success that you're particularly proud of?

Kimberley Caines-Best (11:43.436)
Yeah, I thought this was a really good question. I'm naturally inclined to, when I think of successes, and this has kind of been my journey, at least through my mid-30s of external accomplishments, but the one accomplishment that I'm most proud of would be my daughter, would be the birth of my daughter. And it's not recent because she's four, but just how she continues to show up in the world, the lesson she teaches me of how she engages with the world just warms my heart. And she is a great teacher and doesn't even know it. I had her later in life. I was one of those individuals, I guess, that focused on their career, got married later in life and then had her in my late 30s. So when she arrived, it was quite traumatic. She is by far my greatest accomplishment or success that I am daily proud of and just so grateful that I get to be her mother.

Aderonke Bademosi Wilson (12:53.016)
Thank you for sharing that. Can you tell us about a time when you made a difference in another's life? What were the circumstances? Paint a picture for me.

Kimberley Caines-Best (13:03.393)
Sure. It's such a gift that when we get to help people, I can't remember who said the quote, that, you know, service is the rent we get to pay for living. An opportunity or time where I've helped an individual, as I was reflecting on this question, was I've created spaces for women to come together, groups of women to come together and be vulnerable and also share of their experiences and there are two in particular. When I co-founded a group called the Women's Legal Network with another lawyer and it was a space where we created for female lawyers to come together to talk about navigating careers as women and then created opportunities for us to learn about negotiation as well as emotional intelligence. And so that was about four or five years that we did that work and it was really rewarding. And then similarly, I created a group on island for individuals, women who are stepmoms, because it is a journey that often women go through and don't have an outlet in which to share that. That group started during COVID, so it's been a little harder to gain traction, but the opportunities that we have had to connect have been so rewarding. And what I realized is that these opportunities to help others came from a need that I had. So being able to provide that outlet and that form was so rewarding. Yeah, and I just consider it a gift to have been able to be entrusted with people's interests and desires. And so I would always leave those spaces feeling so encouraged and so inspired and energized.

Aderonke Bademosi Wilson (15:05.292)
I always feel there's something magical when women come together, when their energy is in a room. There's a magic that takes place and a connection and a sisterhood that leaves you feeling rewarded. I'm not quite sure rewarded is the word I'm actually looking for, but it leaves you feeling, with a feeling of connection, that you've been in a space of understanding. And for me, that feeling carries on for a while after that space has moved on.

Kimberley Caines-Best (15:52.406)
Yeah, I would absolutely agree with you. I think me seeing the value of women coming together, I went to an all-girls school from the age of five. So I've seen the power of women coming together and I've seen the value of sisterhood. And I am just so grateful that I have amazing women ahead of me on the journey of life, beside me and coming behind me that I can do life with. I wholeheartedly agree with you. I know we were in a shared space recently with amazing women and I know I left on just on a buzz thinking, my gosh, and you think, when's the next time I can get together with women and experience this again? So I absolutely agree with you that women, there's an energy that women bring together. And especially when there's authenticity and vulnerability present, you leave that space changed.

Aderonke Bademosi Wilson (16:49.836)
What were the key strengths and qualities you relied on to make a difference with these organizations that you created?

Kimberley Caines-Best (16:59.989)
The first would be stepping out of my comfort zone and realizing that, you know what, maybe somebody else isn't going to take the first step. Maybe it needs to be you. And not in a braggadocious way, but in a there's a need, maybe you have an answer for this need. And getting my own kind of ego and imposter syndrome out of the way and recognizing like, hey, I have this need, maybe there are other people that do as well. Being transparent, being honest was also really important, particularly in the space of community for stepmoms. And just not being afraid to ask for help. And so that was really important as well. And yeah, I think those were the main things that I relied on and not being afraid to appear foolish or make a mistake and all of those things that kind of keep you in your comfort zone. Because there's that quote that, you know, life begins at the edge of your comfort zone. And with both of those experiences, the response was what was so rewarding and validating. I was like, okay, yeah, I wasn't out in left field thinking that I was crazy for doing these initiatives.