Developing Confidence with Chris Kazi Rolle and Kerry Ann Reid Brown

COF 031: Developing Confidence – The Struggle of You vs. You with Chris Kazi Rolle


Chris Kazi Rolle is a Bahamian American Strategist & Matchmaker known for helping people create winning strategies for business, life & love. Kazi has certifications in life coaching, crisis management, conflict resolution and business management. Kazi’s work and life is the focus of the Bruce Willis and Queen Latifah award-winning film, The Hip Hop Project.

In this episode:Developing Confidence – The Struggle of You vs. You;  Chris gives insight on the challenges we often face with ourselves when trying to develop confidence. He also shares strategies on how we can begin to develop confidence.

Connect with Chris on Social Media

Twitter @chriskazirolle

Instagram – @chriskazirolle

Facebook – Chris Kazi Rolle


This episode is brought to you by  What other personal development skills do you want to learn? To give you the opportunity to check out their service, get 10 days of free unlimited access to or take 30% off any membership for a limited time.

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Connect with Kerry-Ann on Social Media:

Kerry-Ann on Twitter – @carryonkerry
Carry On Friends on Twitter & Instagram – @carryonfriends



Alright friends, welcome to another episode of the Carry on Friends Podcast. And you know I’m all about training and learning and development and resources, and that’s why today’s episode is brought to you by I have been personally using since 2011 and it is an amazing resource. offers video  tutorial courses in a variety of topics whether it is software, whether it is a business skill, whether it is a personal development skill. So what I want you to do for me today is check out, go to You will see a link where you can try courses for free, unlimited for 10 days; free, unlimited for 10 days you could try So go to to try for free for 10 days.

Today’s guest on the podcast is Chris “Kazi” Rolle. And I’m so excited that Chris is on the show today because I met Chris New Year’s Day at an event, “The New Year” event and it was so amazing. He gave a really wonderful talk on relationships. Chris is a matchmaker and a strategist and he is known for creating winning strategies for business, love and life. And in this episode, we’re talking about building confidence, the struggle of you against you. Trust me when I tell you that Chris and I had a really amusing conversation and I can’t wait for you to listen to it. I’m going to have all of Chris’s information in the show notes, so make sure you go to the blog and you check out all the information that I have there for Chris. So I’m not going to keep you waiting any longer, here is my interview with Chris “Kazi” Rolle.

Kerry-Ann:Hello everyone, welcome to another episode of the Carry on Friends Podcast. Today, my guest on the show is Chris “Kazi” Rolle. Chris, welcome to the Carry on Friends Podcast.

Chris:Yeah, yeah.

Kerry-Ann:Alright, yes.

Chris:Happy to be here.

Kerry-Ann:Great, great, great. So excited. So before we get into the topic of the show which is “Developing Confidence: The Struggle of You Vs. You”, tell our community of friends more about who you are.

Chris:Well, Chris [02:34]is my name. Born and raised in Nassau, Bahamas, came to America at 14 and worked in the music business and transitioned out of the music business into personal development and have been here ever since.

Kerry-Ann:Cool. So you said “yeah yeah” in the beginning, so tell the people which island you are presenting right now.

Chris:Well you know the Bahamas has multiple islands, but I’m from the capital which is called New Providence or Nassau.

Kerry-Ann:Cool, cool.

Chris:And I grew up in – actually grew up in foster care. My mom is actually Jamaican and she…


Chris:Yeah, and she moved from the Bahamas at about 26 years old and had a beautiful baby boy on an island with another Bahamian. So my dad is Bahamian and my mother is Jamaican. So I represent the 242 and the 876.

Kerry-Ann:Alright, alright. We love it, we love it. So you mentioned that you worked in the music business, so after 10 years of working in the music business, what made you move from artist development to personal development?

Chris:That’s a good question. I was – a lot was happening in the business where there was a website – a college kid named – I can’t remember…

Kerry-Ann:It was Napster.

Chris:Napster, yeah a lot of stuff changed during that time and there was a fear that the music business was not going to be around for a time period and then even the music was changing, so I kind of wasn’t as motivated. I was working with some of – Sean Combs, our producers, and they wanted me to kind of put a certain type of music out there and I wasn’t really into that. And so I had started an artist development program for young artists who wanted to not be what the radio said you should be, what corporate America said you should be. I’m all about originality and finding your unique voice. And so in working with those young people, things kind of just snowballed from there. And I met Russell Simmons, and Russell Simmons, he was kind of shifting as well and he was doing more things to try to empower artists who use their voices in a more political and socially conscious way. And he loved what I was doing and became a big supporter of my work and then he brought on Jay-Z and all of the different artists and executives to help me in developing this next crop of young artists and executives. Bruce Willis and Queen Latifah actually made a movie about the whole program I created. And so that kind of put me in a different world, I was getting calls to speak all around the world. And everywhere I would go I would connect with the audience in a way that was so impactful upon me and I said well you know what, I love this thing, I love the music but I really like working with artists and working with people and engaging them on how they can make their life better and how they can heal from things of their past and make their time on this earth meaningful. And so I discovered [05:34]and Tony Robbins and Les Brown – never even heard of them years prior, but at that time, I kind of started exploring this whole world of personal development. I would say more I stumbled into it; it wasn’t something that I directly said I wanted to do, but sometimes you do stumble into your purpose but you know when you are there.

Kerry-Ann:You know you just said something about meaningful. The tagline for Carry on Friends is “Live Meaningful. Build Stronger. Achieve Abundantly”. Because it is through living a meaningful life, then all other things sort of fall into place because now you have a better sense of your purpose and that allows you to build whether stronger connections, stronger brands or businesses and then ultimately you have more achievements as a result of working from your whys or the meaningfulness of why you do it. So I’m glad you mentioned that. You said you enjoy helping people find their voice, and this episode particularly is about developing confidence. And earlier, I was speaking to a fellow blogger, Caribbean American blogger, her and her family represent Guyana. We were talking about confidence in terms of Caribbean Americans. And it’s a unique position because when we are amongst ourselves in a group, when we are cheering on Usain or cheering on the Bahamas relay team, we have this like bravado, like yes, but I think when we are on our own, by ourselves or maybe in a corporate setting, I don’t know – I can speak for myself, that confidence don’t necessarily come through the way it would if you and I were just sitting there and we’re watching a race or something. So tell me a little bit as to why you think that that’s the case for me as a Caribbean American and potentially others.

Chris:I think when you come to America, you know you’ve grown your whole life watching America on television and wanting to just visit this place that just seems like amazing. Because I remember watching the toy commercials as a kid and everybody just always seem so happy and they seem like they always had the cool toys that my family couldn’t afford so I couldn’t get access to, so I always dreamt of coming to America. So then when you come, you are like this small peon in this big country with all these other people; you don’t feel like you necessarily belong because this is not your home. And so it’s like me against the – and do I fit in with the people and the places that I go and when I open my mouth, will they understand me or will they make fun of me and the way that I – I’m speaking English, but I don’t speak it the way they may speak it, and it’s a lot of them against me. So that confidence is – it’s hard to feel confident when you don’t know where you belong, you don’t see yourself in a sense. And so I think people like – a lot of the rappers who come from the West Indies like Doug E. Fresh and Busta Rhymes and Heavy D at the time, they – when you find out oh those dudes are Caribbean, like it kind of makes you feel like my voice can be heard and I can feel confident when I’m in a place where I can have my voice hurt, but when I’m around other people where I don’t see myself or see the way that I speak in those circles, it is hard to be confident and just say even though I’m not one of you guys, I’m somebody, what I say matters.

Kerry-Ann:Yes, yes. So what advice would you have for someone like me or someone listening who will find themselves in a corporate setting for a business meeting or maybe networking for that reason because you have this insecurity, what advice would you give for us in terms of developing that confidence to – you found your voice, what advice would you give in terms of helping us find our voice and to lean into that truth of our voice?

Chris:I think first, it’s about knowing the people who came before you; Sidney Poitier, Harry Belafonte – they are Caribbean Americans. So when you know that you have a vision of somebody who came before you, then you could say hey, I can be like them.


Chris:And so number two, is be excellent. You know live a life of hey is this the best that I can do, have I practiced, have I prepared myself to go into this meeting to be among these other people who are also aspirational and going after their goals. When you are prepared, it just builds your confidence. A lot of the times, the reason why we lack confidence is because we are not really sure how good we are, but when you really do the work, when you did your homework, you will go in there and say you know what, I did the best I could. And you walk differently, you talk differently when you are sure of yourself. So when you live for a spirit of excellence, you will always put your best foot forward and that makes you feel confident. 

And then the third thing is to really do your homework about the people you’re going to be around or working with because when you do your homework, whether that’s exploring their social media pages, their LinkedIn page, people care about people who care about them unless they are just horrible people. But you come into a place, you give someone a compliment or you acknowledge something of their own heritage or you say something that you know they are proud of or that they have accomplished, it brings a connection. Everybody lives for acknowledgment, so when you acknowledge someone else, it makes them feel good; now they’re opening a space for you and they listen to you differently. If somebody’s looking at you and with an eye off, “who is this guy?”, it’s a lot different than, “Well, thank you for that. And now in the spirit of reciprocity, I want to give you back what you gave me, that acknowledgment.” You can feel confident to move forward because you won people over. So it’s not always about trying to get people to understand you, it’s about trying to understand who you are talking to. So I think those three things will help you if you’re feeling a lack of confidence going into some sort of business or presentation.

Kerry-Ann:Nice. So how do we go about assessing our strengths and weaknesses so we can help build our confidence?

Chris:Yeah, I would say a lot of it is awareness. A lot of my clients, I would have them just make a list of all the things that are interesting about them whether they think it’s interesting or not, that they have either a compliment they’ve heard, things that they think are pretty cool about themselves or just random facts about themselves – just having all of that in the forefront of your mind, it just gives you a sense of your own uniqueness, your own special fingerprint, that God only made one person like you. And sometimes we forget that, we’re always thinking about what somebody else has or thinking about what we don’t have, that we don’t acknowledge what we have. And so if that consumes your mind, you will lack confidence.

I would say the second thing would be to not compare and catch yourself when you are comparing yourself to someone else. And social media can do that; you know you look at someone else’s page – these are just highlights, they’re highlight reels*, but you are comparing your whole life to these little snapshots that some may even be pre-orchestrated. We got to be very careful about comparing ourselves to other people. You know you cannot knowledge what someone has, but just saying I’m bad because they have that or they are doing 123. I mean I have friends who would go out for one day and take a whole bunch of pictures, bring out different outfits and you know just travel around with their photographer for that day to get a bunch of photos that they would then put out – what they call like drip content, they would put it out there overtime. And it would seem like they are always out and about doing a whole bunch of things, but that’s the perception they want to sell. So it’s very important to manage your consumption of social media because it will lead you to comparing yourself and it is toxic, toxic to compare yourself. So you got to get yourself during those times. If you are busy working on you, you can go and look on social media for inspiration, but it’s not about comparing. You don’t even get to that place, you may go oh that’s cool or I like what that person is doing, I’m going to use a little bit of that and what I’m doing.

So I would say, that would lead me to the third thing. It’s just get consumed with what your purpose is, like I believe that you have a certain amount of time – they call it the dash; there is the time that you are born in, the time that you will leave this earth and then the dash is the time that you spend, spend that time doing what you are here to do because you are only here for a time period. And the unfortunate thing is, until we realize that you know what, we’re on our deathbed or we have a near-death experience, then you’re like oh man, I got to leave, I got to take advantage of the time that I’m here, but other times, we kind of like squander that, preparing ourselves or doing things that don’t add on to our purpose. So I would say consume yourself with what you are up to in the world because when you do go and look at somebody else and what they are doing, you will be inspired more than you would be beating yourself up about what you are not or jealous. Some people even feel those emotions, because actually jealousy and inspiration are the exact same energy, but it’s a different polarity of that energy. So if you’re – they say “devil find work for idle hands”, so that’s why you have to consume yourself with me in an action because when you are in action and you do stop to take a rest or break and you are observing the world around you and seeing what other people are doing, that seeing them would only inspire you as opposed to you all being derailed or have your energy pulled down into a negative place because what they are doing, you would feel it’s so much better. So those would be tips that I would give someone in terms of just building their confidence.

Kerry-Ann:I wrote down every single one of these, like one of the [15:21]things you just said, jealousy and inspiration; same energy, just polar opposite. And based on that, it’s really just a thin line; it’s how you take that energy and use it. Are you going to look at that and then stew in it because that’s where the jealousy comes in or are you going to look at that and then you are going to act, that’s where the inspiration comes in? So I mean this was – that was just amazing. But you are right, comparison is the thief of joy. And if we are just constantly absorbing or consuming these social media images – I think I posted a quote where someone said, “Don’t compare your life to someone else highlight reel” which is what you said. And that’s what Instagram or social media is, it is a highlight reel, and it’s good to look at it but understand that – just take it with a grain of salt and then you just dip back out, so all amazing. And for me, going back to what you said, the awareness and the preparation, is really key. You know sometimes we feel overly confident and we don’t prepare as much, but that preparation makes all the difference. I just love that. So yes, I will put these in the show notes, awareness – so be aware of your strengths, we all know our weaknesses. But I love that you said make a list of the things that are interesting, the compliments, the things that you think are cool because maybe we spend too much time thinking about the things that are not so cool or not so interesting that we should remind ourselves. I just love that. I just love that. So thank you for saying that, because we don’t do that enough. We’re consumed like oh, I need to lose some weight, I need to do this, I need to do that, and never taking in like you know what, my voice actually sounds good on this podcast. You know what I mean?

Chris:I’m not only talking from expertise, I’m talking from experience. I definitely have been guilty of seeing somebody else over there and just so consumed by them that there is no space for myself. And they say all things in moderation. I think it is going to look around this beautiful planet and meet interesting people who are just so different than you and be able to appreciate them. But it goes into a level of extreme or imbalance when you are so enamored by somebody else that you forget yourself and it’s just unhealthy really, it breaks down to that. And so at some point, there were friends around, and I didn’t include this in terms of building confidence, you have to be around people who acknowledge what’s in you and believe in you. And like the people in the faith-based community, they say speak into you; they speak words of encouragement, they acknowledge the gifts that you have. Sometimes we don’t see ourselves, so they remind us, they bring us back to who we are. There is an old saying, “you can’t see the picture when you’re in the frame”, so having a community of people to acknowledge what’s great about you. And I’ve had mentors and I call them angels in my life who have reminded me like you are great as well, it’s great that you can appreciate other people but they remind me of that. And I think that’s what makes me effective as a coach and working with different people, is I could say I’ve been on many sides and I could say hey, I have figured out this path and along this path, I remember the directions that I took to get to where I am and so I could tell you hey, don’t do that. Do not spend your time consumed with somebody else’s gifts, talents and abilities. The conscious mind can only hold a certain amount of information at one time and whatever you constantly do in the conscious mind, it then stores it away in the subconscious and the subconscious just operates from what is being stuffed into is on a repeated basis. And so if you want to shift it, you have to spend more time consistently doing the thing that you want your subconscious mind to…

Kerry-Ann:To now do, yeah.

Chris:And so that’s why I say making that list and putting it around your house; make art or pictures that remind you. I have a wall in my house that’s just of great moments that conjure up a certain type of energy in me. And I keep those around as a reminder of my own greatness. Because the other thing is, I just love people and I love seeing the greatness in people, and I think that – that’s why I said the word in balance*, because I think it’s a great skill to be able to do that and not be so self-centered. That’s the opposite end of the spectrum where you are so consumed by yourself that you are not aware of other people’s greatness. So it’s all about being balance, in balance where you can acknowledge other people, the beauty and other people, talent in other people, but also still aware of your own…



Kerry-Ann:You know what you just said there before, you just said the conscious mind could hold but so much and whatever it can’t store, the subconscious mind take over which is your autopilot, the autopilot because the subconscious just controls everything. And in order to change the autopilot that we fed to the subconscious, we have to change what information we put into ourselves, and that is so key because – and which is why developing confidence is so hard because we are trying to – as we say tape over or dub over what we’ve done in the past, and that is challenging because the subconscious, because it’s now on autopilot, it’s comfortable and the minute that we have to change that, it feels different and it feels wrong. So I think that’s key that as we are changing, it’s not going to always feel comfortable because we’ve been on autopilot for so long. The other thing that you said which I actually practice, years ago I read in a book, it said to have a compliments bank. So I don’t have pictures on my wall, but whenever someone sends me a text or even the other day, your email, you said you liked the podcast, I took a screenshot – click and I save it in my ever* notes. So whenever I’m feeling a little like I don’t know if I should be doing this, I just go back over and look over those things to remind me because I’m hardest on myself, and so in order for me to step out of my way as Jullien says, get out of my way, I look at how other people perceive me because like you said, they are speaking into my life. And they have done that by offering kind words or supportive words to tell me that hey kid, you are doing great, keep doing it. So I think those are really two powerful things or that’s a powerful tool that I wish a lot of us would start keeping, whether it’s a wall of events like you’ve mentioned or it’s simply just keeping comments and just reviewing them when we are in a space of doubt. So as we wrap up, what’s one advice that you want to give to anyone from the Caribbean, anyone who’s Caribbean American and they are struggling or they are trying to figure out where do I fit in all of this, who is still saying yeah I hear what you are saying Kerry, I hear what you are saying Chris? What’s one advice would you give to them in terms of finding their voice and living meaningful?

Chris:That’s a good question because to drill it down to one thing, I would say – I’m probably a little resistant to say this because I know that religion and spirituality could be all subjective and divisive, but I would say build a greater relationship with a higher power, because it has helped me with recognizing that I am here for a purpose and I have been given certain gifts, talents and abilities to help me complete that purpose. And if you think about the creator, like a better example, Steve Jobs and the Apple computer; the Apple computer has specific programs that Steve Jobs put into it to fulfill a particular purpose. And so the better you understand the purpose that the designer had for the machine, then the better this machine will work which is why you read the manual. So as the machines created by God or the Creator or whatever spiritual belief that you may have, I would say the more you understand why you were created, the better path you will have to accomplishing your goal. For instance, I’m from the West Indies right, and growing up there I lived in foster care and then I lived in multiple homes. I lived with white people, I lived with black people, I lived with younger people, I lived a whole lot – I saw whole lot of different families of different dynamics. I knew a lot about different religions and different cultures, and came to America and kind of had a similar experience and worked with the Jewish people and Russian people. I know so much about the inner workings of people and I read a lot. And I feel like it’s all been pre-orchestrated. And I think as I recognize that God has been or the Creator has been working in my life and all of this is by design, I’ve been able to see it clearly. There is a speech by Steve Jobs actually. It was a Stanford speech…

Kerry-Ann:I know it. I know what you’re talking about. Go ahead.

Chris:And he says when you look back, the dots connect and when the dots connect, you see the full picture. So I believe that the more you understand that there is a design to your life and you have to figure out those clues which start with your own gifts, talents and abilities, then you will be able to figure out all right, this is the purpose that I’m here, and whether that means leaving my hometown or home country to another country, there is a plan for me and I know that doors are opening. And so if I’m in a room that I can’t believe that I’m here sitting across from this celebrity or this business person – whoever I’m sitting across from, I belong here and there is a force that’s opening the way for me to move forward. And unless you are aware of that force, aware of that purpose, then you could doubt hey, is this for me, how did I end up here, I shouldn’t be here. And I’m just speaking from experience, that has been a great tool for me along the way, spending that quiet time and asking what am I supposed to do now, why am I in this particular relationship, why am I in this situation, what is it that I’m supposed to see and knowing that the answers will come and show themselves. That’s probably been the greatest tool that I’ve used along my journey to understand this thing called life and to be successful at it.

Kerry-Ann:I am having a moment with that one take away. And I can say this, that you being on this show in that one moment was predestined. Weeks ago, I posted that same exact Steve Jobs quote which says, “You can’t connect the dots looking forward, you can only connect them looking backwards.” And I had that quote because I have been on this journey of following the patterns in my life and that also stems from a speech by another Caribbean American, Haitian-American, Christine Souffrant. And she said the same thing, like the patterns – the only way – you know because someone listening might say yeah they are talking about your purpose, but I don’t know my purpose. It’s looking for the patterns, that’s what Christine said. Look at the patterns in your life because if you go back and look at the things you like to watch on TV, the things you got involved in, you start to see a pattern developing and you just kind of follow those patterns. It’s so amazing that you just brought that up, this podcast is a part of a pattern. All the things that I’ve done – and I’m just kind of like you said, you trust that higher power and you just kind of – you follow those patterns and just kind of move in that gut feeling that you have. As Steve Jobs said, you got to trust in that in your gut somewhere, it’s going to connect. And that’s what you did. You looked back at your life experiences and you are like I did this, I did that, I did this, and it’s all starting to make sense. So I really think that’s really powerful. Look at the patterns, this is what Chris just said, look at the patterns in your life and then you have to trust that, you know you have to believe in that higher power that is creating this pattern in your life for you to live in your purpose. So I really, really, really believe you are supposed to be on the show Chris. That’s what you said, it was just like so amazing. I’m like jumping in my chair because you just said that. I literally posted that to my Facebook page may be about a week ago and I said – and Ginger commented because I said you know what, the patterns are in focus.

And my take away outside of that and all of that, is in order to develop confidence, we need time with ourselves. You said God and that’s part of it, you need time with yourself and God, because a lot of times we could get feedback from other people, but we also need to be by ourselves to kind of really drill down, we have to really be honest and be aware like you said. Get rid of the comparison or figure out why are we on the jealousy spectrum and not the inspiration spectrum of the same energy. It really comes down to time with self, time with God to really step outside of yourself. So many people say this, it’s not until they disconnect that they reconnect. And that’s important in terms of developing your confidence and really winning the struggle against yourself. So I’m so excited about this, it’s like yeah! So island people, you guys are innate that you are entrepreneurs, it’s innate that you have the spirit of excellence. We come from a long line of people who were just excellent, from the Marcus Garveys, the Sidney Poitiers, the Harry Belafontes. We come from a lineage of excellence and we continue that, but we also have to understand that personal development is part of that process. So Chris, Kazi, thank you for being on the show. You are so awesome. Thank you so much.

Chris:Yeah, this was awesome. This is a unique space. I don’t know of any space that is like this per se. So to have that expression, and I was just watching something on Facebook, a video of Richie Stevens, I think is the artist’s name, and he was just talking about Rihanna.

Kerry-Ann:Rihanna’s work. That’s the big topic now.

Chris:Oh yeah, you know. So it’s kind of – I know there is some tension between it, but he did also acknowledge that what she’s doing is she is creating a space now that maybe in the future, songs like her song with Drake will just be the norm and so it opens the door for other artists coming from – she’s from Barbados right?


Chris:Yeah Barbados and Jamaica to be in mainstream because people just know that sonic. So I would say for someone like yourself and what you are doing, creating this space where we could feel like that’s a space exclusively for us.

Kerry-Ann:Right you know, we’re here. We are here and we’re making waves, we’re doing things but we’re doing it so quiet that no one’s really knowing and we are not really like I said to Alysia* in the previous podcast that if we’re trying to set examples for the next generation, then we have to be visible examples. You can’t set an example that no one can see. So it’s been a year and it’s been – I really enjoy it and it’s growing and believing in the platform that this is why I’m doing it. I want to see representations of myself. I want to see what’s powerful. Oprah is great, but I tell you there is a whole galaxy between me and Oprah right now. I need to see – you know like she’s a great standard for success, but shouldn’t be the only standard for success. And there are many steps or levels before she got to where she got to. So we need to also recognize that there are other people who are doing great things and we should tap into their experiences and figure out what they’ve done and how we can improve on what they’ve done and how they could teach us. And you know what, it’s all about live meaningful, build strong and achieve abundantly because we have to do the thing right. That’s how we do it. Done know! Yes so I’m so excited. Thank you so much for listening. And we’re so grateful for Chris to be on the show. I’ll have his information in the show notes so you could connect with him. And until next time, walk good.Chris:Walk good.


Kerry-Ann Reid-Brown is Founder & host of Carry On Friends one of the first podcasts dedicated to the Caribbean American Experience. She is leading the way for Caribbean Podcast as the founder of Breadfruit Media, the first Caribbean podcast production company; and founder of the Caribbean Podcast Directory a place to discover podcasts by people of Caribbean Heritage.