Rethinking Success Work Life and Rebirth our true self with Lisandra Rickards

Rethinking Success, Work & Life to Birth Our True Self

Lisandra Rickards is Chief Entrepreneurship Officer at the Branson Centre of Entrepreneurship – Caribbean, where she has developed and delivered scaled initiatives to thousands of Caribbean entrepreneurs. Before joining the Branson Centre, Lisandra conducted economic and statistical research for the best-selling books Freakonomics and Superfreakonomics. She has an MBA with First-Year Honors from Harvard Business School, and a B.A. in Economics from the University of Chicago, where she graduated Phi Beta Kappa and Student Marshal. In 2008, she was featured in the CNBC documentary The Money Chase: Inside Harvard Business School.


How are you living? Are you working to live or are you living to work?

In this episode Lisandra shares multiple insights on success, work & life. Including how she had reached her limit of achieving for the sake of achieving; and it was time for a break and figure out what she enjoyed and could blossom and radiate in.
If you’re feeling exhausted, overwhelmed or unsure – Lisandra’s journey and story will sure to transform you.


Resources discussed:
  1. Career Leader – The CareerLeader assessment helps you identify your business skills, interests, and motivators. Based on your results CareerLeader will define potential career paths and why you match these options.
  2. Clifton StrengthsFinder – The Clifton StrengthsFinder 2.0 helps you uncover your natural talents. There are 34 different talents called themes and the assessment provides resources that show you how to build your personal strengths into your work.
  3. Acumen Plus course on Storytelling
  4. Udemy
Find more tools on our resource page.



Connect with Lisandra Rickards:

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Text: 347-875-0531

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Hello, everyone. Thank you for tuning into another episode of Carry on Friends, the Caribbean-American podcast. I am really excited for you to listen to this episode. My interview is with Lisandra Rickards. She’s the CEO of the Branson Center in Jamaica. When I go through my interviews with the podcast, there’s actually a plan when guests are asked to be on the show, there’s a topic that I suggest, and I have an idea of what I want to go through, what the interview flow is going to be like. This interview was totally not the direction I wanted to go, but it was the direction it needed to go in, because I needed that. So Lisandra was a messenger for me that morning. I told her after we recorded, after we had ended the recording, how much that interview was just timely for me. I was in this place at a crossroads and she was just feeding into my soul, some of the things that I was just like yes, I thought it was just me, and yes, that’s where I am, and yes, thank you for those messages. When you listen to it, that’s not—you may not be there or you may be there, but I think the conversation we had was just very important. Lisandra is highly qualified. She has such a diverse experience, but she spoke to something that I know that a lot of us can relate to at some point. I just can’t wait for you to listen to this interview. Lisandra, thank you for being the messenger for me during that recording. As I really relistened to that interview in finalizing it to go live to the community, it was just like notes after notes. It was just like when di word good or when di message good, it jus’ good. So I hope you enjoy listening to it. Here’s my interview with Lisandra.

Kerry-Ann: Lisandra, welcome to the podcast. 

Lisandra: Thank you. I’m so excited to be speaking with you today. 

Kerry-Ann: Awesome, awesome. So Lisandra, tell the community of friends a little bit about who you are, island you’re representing, and all that good stuff. 

Lisandra: Well I’m representing Jamaica, I’m born and raised. I’m currently the CEO of the Branson Center of Entrepreneurship-Caribbean, which is an accelerator for entrepreneurs. It’s based in Kingston. I also love a lot—I have a lot of different interests. I’m an avid reader. I’m very into Eastern Philosophy right now and meditation. So we can talk about any of those things. 

Kerry-Ann: Awesome, awesome. Tell us a little bit—well tell the audience a little bit about your story, because I know that you’ve studied and worked here in the US before your role at the Branson Center. So give us a little—just a quick high view of that journey. 

Lisandra: Sure. Growing up in Jamaica, I always wanted to do something that would impact the economy and help lift people on a larger scale out of poverty. So all in high school, I was very focused—well probably in the later years of high school, I was very focused on I want to do economics. The University of Chicago came to Campion (that’s where I went to high school) and recruited students from Campion. They were big in economics, and still are. I applied and I got in with a scholarship, so I moved to Chicago when I was 18. Very cold, very windy, very much a change from Jamaica. Boy, I mean, when I later went to Boston, I would think back on Chicago years, and Boston winters were like summer day compared to Chicago. So that was actually very hard to adjust to, and it’s a very challenging program at that school, but it really taught me how to be very analytical in how I think. By the third year, the winters were getting to me, so I took a year abroad in Spain, in Seville, Spain, and became fluent in Spanish, traveled a lot to all over Europe, and just really came into my own. For the first time, I took off that laser focus on grades and achievement and academics, and discovered that I was actually more a Bohemian, that I loved roaming around the place, Europe. I went to Rome by myself, traveled on a bus from Paris to Rome, walking around by myself. I loved just the freedom and how philosophical everyone was. The whole culture in Seville was working to live and not living to work, which was very different from North America where you’re judged on what you do. In Spain, it wasn’t about what you do but how you were living. So I’ll just give you a quick example here. I lived with an older, grandmotherly type of woman. She’d be out until 3 AM every night, having a [inaudible 05:51]with her friends, a little beer. That was just life there. 

Kerry-Ann: It’s so funny that I’ve heard similar stories of when people go to Europe and the lifestyle there which is more living life itself to be enjoyed. Whereas over here, we’re just—like in the US, it’s a constant working, grinding, working, grinding, working, grinding, and not really taking the time to take care of yourself or to live in the moments or enjoy the fruits of the labor so to speak. 

Lisandra: Totally. There’s music, the whole—just walking down the street, you’re walking in history; the architecture, the art, music, the food. It’s just life. That year changed my whole life and my whole perspective. I came back to Chicago in a very intensive pre-PhD Economics program, doing honors statistics, honors calculus, honors econometrics. Coming back from Spain right back into that was jarring to say the least, but I stayed on that track. I graduated and then I started working for the author of “Freakonomics”—he wrote the book, “Freakonomics”—and doing a lot of academic research. It was really at that point where everything I learned in Spain, but I wasn’t implementing in my life, came to a head and I said I don’t want to do a PhD in economics. I’m not an academic. I want to live life and enjoy life more and do something that’s more in line with who I really am, but I had no clue at that point what that was. It would take me many years to kind of figure out what that was. 

Kerry-Ann: What I’m sensing from your story so far, that’s really resonating with me, is the ability to incorporate new experiences to kind of reframe what plans we had without those new experiences. It’s like opening the possibility of what else, because a lot of times we go in where this is laser focus, this is the plan. It takes going out on a limb for something completely out of our comfort zone and to just kind of look at different possibilities. Okay, so you decided you didn’t want to have a PhD in economics. How did you end up at the Branson Center? 

Lisandra: Yeah. Well I have to tell you that whole—I mean I have to go through that journey with you because it’s a real awakening that took many areas. So people think find your passion, find your passion, but it can take you years to figure out what that really is. It’s not you do a vision board and suddenly you find your passion, it doesn’t normally work like that… 

Kerry-Ann: Thank you. 

Lisandra: … and it didn’t for me. 

Kerry-Ann: It hasn’t worked like that for me, so I’m glad you say that. 

Lisandra: So my mentor, who was the author of “Freakonomics”, Steve Levitt, he told me, “You’re a good for business school because you have a big personality, you’re a people person, you like networking. That means you should go to business school.” I didn’t really have another plan, so I took his advice and I applied to business school, and I got into Harvard Business School with a great recommendation from him. And again, this was another, just birthing of my true self, because HBS is—and I don’t know if this is appropriate to say, but I would say it’s less about the academics and more about growing as a person, growing your network, seeing the world, talking to the people in your class who are going to become the leaders of the world in the next 10 years. The academics to me was not as much in focus as it was in my undergrad experience and it was more about people and life. So I traveled again. I went to Dubai. I went to Mexico and Colombia and Abu Dhabi and Egypt and Bahrain. Just learning from my peers who had come from all these different backgrounds. Each class at HBS has 90 students, 90, whole heap a people who are really smart, come from all over the world with lots of different perspectives. I’ve just learned and grew so much from listening to them talk about their ideas in the classroom. So after that high of HBS, re-entering the real world is very jarring. Again, you’re at a pinnacle, you feel like you can do anything and take on the world. I mean it was just so high. And so you come back to mundane life of business, like an admin and figuring out what to do next. It can be a real come down. A lot of people go through this depression phase after HBS, when they re-enter the real world and it’s not as amazing as our experience was. I went through that for sure. I would say I was lost for three years after business school. 

Kerry-Ann: How did you get over that phase? What you said is totally appropriate. College and your college experiences are really building the networks, because as you see, a lot of startups and companies, they tap into their peers, the alumni. So it’s really about building the network. I’m curious, how did you get through that depression or that phase after college, where you realize that it’s mundane and you’re kind of feeling a little sad or depressed about where you are now? 

Lisandra: Yeah. Well I graduated right in the middle of the great recession. So it was not a lot of jobs available outside of investment banking or consulting for international students, which I was. At that time, I had reached my limit in just achieving for the sake of achieving. I wanted to live authentically and figure out something that I really enjoyed and loved, and could blossom and radiate in, not just feel like I’m doing drudgery. So I didn’t want to go into consulting. I didn’t want to go into investment banking. So the only place left for me to go was back home to Jamaica to find myself and give myself the freedom to figure out what I really liked. So I moved back to Jamaica in 2010. I took three jobs in three years, because I was like I’m not going to stay if I don’t love it. I’m just going to keep trying until I hit the jackpot of the thing that I love to do, but you see your peers being in private equity and launching startups and selling them for $200,000,000, and you’re back in Jamaica jumping from job to job and you feel like, did I make the wrong choice trying to find myself? Am I doing the right thing? Maybe I’m just a bad egg in the whole class. 

Kerry-Ann: I’m telling you, you’re speaking to me right now. I swear you are speaking to me, because it’s that experience and no one talks about it. So I’m glad because you sit back and you’re like, “Am I’m doing something wrong? Which part of the class I wasn’t paying attention to?” 

Lisandra: Because you all graduate at the same level, and then the choices you make determine the outcome of your life after that. So the choices I was making was bringing me closer to my true self, but early on, it felt like I was making choices that made my life stagnant. Whereas, my peers were accelerating their lives to the next degree. So I was really down on myself about that, but I felt compelled, it was a compulsion to keep trying to find something I liked, to the point where when I left my third job, I was like, “Well, I don’t think I like business period. I’m going to move back to Spain, be a waitress, write a book, maybe be a travel blogger and forget this whole business school achievement thing and just run away and be free.” 

Kerry-Ann: Yeah, sounds like a good plan. What interrupted that?

Lisandra: Well exactly at that moment, I got an email in my inbox from Lisa Lake, who was the CEO of the Branson Center and a friend of mine that I had known. She had gone to Harvard Kennedy School, so she was one of the alumni in the network. The email was advertising for a part-time position, three days a week to train budding entrepreneurs in business and how to do business better. Three days a week, not a lot of pay, just something to do. So I was like well this sounds interesting. I can do this while I write my book and save up money to get my plane ticket to move back to Spain. 

Kerry-Ann: Yes, yes. It’s coming together. This is perfect. 

Lisandra: So I took it part-time and I just fell in love with my job the first time. Just when I was giving up on the search, I fell in love. The entrepreneurs just inspired me. Being in a tough economic situation like Jamaica and still—entrepreneurship is a belief that the future is going to be better than the present. And so being around 20 people who all share that belief and were giving up 9 to 5, giving up salary, giving up everything to launch something. It just started healing me on my own search. It went from three days a week to four days a week to three years later. Just in three years after finding the thing that made me glow, I became CEO at 32. 

Kerry-Ann: Awesome. It’s really grounding to hear the story, because on the outside looking in, I could a seh, “Bwoy, you see if me go to Harvard Business School, wah? When me done, this is what’s  going to happen.” For you to share your story, which thank you so much, to say well, that’s not always the case. You go on different paths. In your story, it’s like be okay with this different path. I mean, yes, you’ll have some comparison and you’re feeling—you question it, but it’s pushing through that keeps you to ultimately figure out or fall into. It seems like you’re meandering, but you’re really moving towards where you really wanted to go. Thank you so much for sharing that. I can’t even begin to tell you how God sent you to tell me that story this morning. 

Lisandra: I think the key is to hold to the feeling, really pay attention to how you feel doing different things, and keep acting in the direction of things that make you feel good. Once you do that, the universe will bring things into your domain and you have to say yes to them, in order to keep moving up on the path towards feeling good in what you do. 

Kerry-Ann: Yeah, absolutely. Yes, thank you so much for that Lisandra. So Branson, I’m very familiar with Branson Center, I don’t want to assume the audience is. So you mentioned that it’s an accelerator, so just talk a little bit about what’s happening at the Branson Center in the Caribbean and what you see in the future for entrepreneurs within, not just Jamaica, but I believe the center services other islands. So tell us a little bit about that. 

Lisandra: Yeah. An accelerator helps entrepreneurs who have—they’re not in a startup phase, you’ve already launched a company, you’ve gotten some traction and now you’re really ready to expand and take your company to the next level. So that’s the place that we play in right now, not the startup phase but the scale up phase. We took a shift actually, because when we just started, we were in the startup phase, but we shifted because of this belief that economic growth, changing our economies in the Caribbean, making them more dynamic requires more activity. It requires not just starting small and staying small, but building something that lasts, that grows, that employs people, and that really makes a difference. So in order to get more transactions, more deals, more IPOs in our Caribbean economies, we need to give entrepreneurs the tools that maybe they don’t have as easy access to these tools as an entrepreneur in North America would. So we do mentorship. We do business training, investment readiness training, as well as access to funding. So we have a group of partners that are equity investors or even loan, they give loans as well. We introduce our entrepreneurs to them, prepare the entrepreneurs to present to them, and also prepare the investors on how to invest in the scale up stage of entrepreneur and match the two together. So we do the three things: mentorship training, access to finance, and we have a great brand, Virgin and Richard Branson backing all of our activities. 

Kerry-Ann: So it’s very interesting, I know Sir Richard Branson is backing the activities, but I want to back up a little bit. So I know that these are—this is for entrepreneurship in the startup phase. I guess in the US, we have those entrepreneurs who are kind of still in full-time and those who are kind of doing a side hustle thing. Do you find this happening in Jamaica? And then we could get back to those who are doing full-time entrepreneurship. Do you find people who are doing both, or if they’re doing both, they’re only in the startup phase and there’s not anyone doing both who are in the accelerator phase? 

Lisandra: That’s a really good question. There are a lot of people in Jamaica doing both, because our economy doesn’t support a lot of risk, number one. So in order to fund your startup, you have to be working to fund it. You have to work to fund yourself. This necessarily means a lot of startups that start small and stay small, because my strong belief is that if your attention is divided for a long period of time, something has to give or it restrains your growth ability if you’re too divided. The reality is that you have to live. And so how do you do both? We had an author at the center who wrote this book called “The 10% Entrepreneur”. These are people who start companies while they’re in a career. He put a statistic that people who start companies while they’re already doing something else, have a higher success rate than the people who just jump into something full 100 right away. However, at some point, you have to make a choice to go full 100 in your company, in order to give it the best chance for success. The question that every side hustle person has to ask themselves is: at what point do I make that choice? 

Kerry-Ann: So for these people—and I will go to the entrepreneurship because I know that you are sharing your stories with the entrepreneurs, but even still in both cases, like what are some of the mental hurdles you find that are most impacting both groups? What are your thoughts on helping people to kind of get through that? Because I mean, this wasn’t initially part of what I wanted to ask you, but your story resonates with me. And so I’m curious as to how you see that manifesting in those who are doing both the side hustle and the entrepreneurship, or those who are just in that entrepreneurship space where the mental aspect plays a huge role. 

Lisandra: It’s really about fear and risk. And so the fear is that if you jump full time into the company that you really want to do, you won’t be able to support yourself and you’ll have to quickly return to corporate life. It’s not an unwarranted fear at all. The question is just to how do you de-risk that choice. So the people who have made that leap, had to save a lot to start building their company, get enough traction before they make the leap. Even then, some of them fail and some of them have to find a part-time job to support. This is Jamaica which is—it’s very hard to support yourself if you haven’t built that traction and that track record before. So the question is really contextual. I would classify myself as someone in this category, not in the side hustle category because my time is completely taken up by everything at the Branson Center. When I think about okay, what would I do after having this amazing experience at the Branson Center, where do I go next. 

Kerry-Ann: Right. What’s next? Yeah.

Lisandra: Because if you work for Virgin and the vibe and the culture, you can’t just jump into a traditional corporate structure after that. There is nothing to do after the Branson Center for a previous employer of the center than to start your own business. That is the only thing to do after the Branson Center in my view. 

Kerry-Ann: Well I read a quote somewhere that Sir Richard Branson said that you want to treat your employees the very best that they’d want to stay, but that you could treat them and develop them in a way that they could go out and do whatever else they want to do, but they’ll probably stay. So this experience is like wow, what do I do after working at a company that allows you so much creative freedom? It’s like take that energy and kind of start your own. 

Lisandra: Right. I would say 80% of our past employees have launched businesses. Actually, one of them called me the other day, they just got funded. Two of them are just getting more work than they ever even knew they could as their own startup. So our previous employees are doing as well as entrepreneurs as the entrepreneurs that we actually serve. 

Kerry-Ann: That is awesome. That is awesome. I know a couple people who’ve gone through the Branson Center and it’s a testament to the power of the program and its space within the Caribbean. Now as we wrap up a little bit, what’s your takeaway or what advice would you give to anyone thinking of going back to graduate school because they want to figure out, they don’t like their jobs? What would you say to an entrepreneur, anyone who’s listening to this right now, who could fall in a variety of scenarios when it comes to life? Because I like what you said at the top of your show, you were done with achieving for achieving sake. I think that was just so powerful. What would you say to anyone now in a place of, they’re in a rut, they don’t know what to do next with their lives? What would you say?

Lisandra: It starts with you. It doesn’t start with school. So you have to learn who you are. We have an idea of who we are, but that idea is not always the full picture. In order for you to get out of the rut, you have to go deep, not up but down into yourself in order to understand what makes you come alive. So I did that in the early days when I just left business school. I did about 15 psychometric tests. 

Kerry-Ann: No, don’t laugh because I have a lot. I’ve done Gallup. I’ve done Myers-Briggs. I’ve done a whole bunch.

Lisandra: So you have to start there. I did Myers-Briggs. I did StrengthsFinder. 

Kerry-Ann: I did that too.

Lisandra: Yeah. Predictive Index which is one that’s owned by or that’s licensed by Virgin. So when I just got my job, they gave me Predictive Index. I’ve done CareerLeader. That’s the best one. 

Kerry-Ann: I love that one too. That one is my favorite. I love these things. 

Lisandra: I can’t believe you did CareerLeader. You’re the first person I’ve met outside of myself, that has done that one. 

Kerry-Ann: Listen, I’m going to find my results. I keep my results and I look at them. So I did like a whole bunch. There was like some free ones. I love CareerLeader. The Gallup one was kind of—was good because it says like—I can’t remember, just a whole bunch of stuff. Yes, CareerLeader. What else did you do? I’ll put these in the show notes. 

Lisandra: The other one, Extended DISC, which you can do for free on Tony Robbins’ website. So those are the ones that I can remember off the top of my head. 

Kerry-Ann: I did a DISC one, but that was—I interviewed at the—true story. I was doing an interview and the company was using—I think Dave Ramsey has some kind of DISC reporting our personality thing. So I did that because the company, I was in the last phase, they offered me the role. I didn’t take it, but they wanted to do this personality thing to see where I would fit in the company. That was interesting, but I love these personality tests. I absolutely love them. 

Lisandra: Me too. I do every single one that I come across. DISC I would say is second to CareerLeader. I would use the version that Tony Robbins does for free, but of course, you have to give up your email to get that one for free. So that’s the very first step. You can’t just do one, you have to get a 360 view of who you are. So one of the things that was a big aha moment for me was, I have a very high score on my aesthetic environment. I need a beautiful, harmonious environment to do good work. So I was in cubicles, the claustrophobic offices. I need windows. I need light. I need tall ceilings. I need just a beautiful environment. The Branson Center is a very beautiful space. So that was one big thing that I didn’t even know about myself. So once you do that, then the next step is to start taking action towards the things that fit the profile you now have of yourself. So I wouldn’t start with school actually. I would start with a side hustle or some kind of volunteering or remote work or three days a week part-time, Upwork, Fiverr. Just start taking actions to doing a job, some kind of work that fits your profile. And then coming out of that, you’ve done that for maybe a year or so, then you can make that decision, okay, is the best thing to go to school, is the best thing to launch a company, is the best thing to go and work at a startup, what’s the best thing for me. 

Kerry-Ann: That’s good. That’s good advice because it’s not enough to take these assessments, it’s to act on them and figure out where you fit, and then being iterative. I’ve tried this, that’s not working, try something else. As long as you’re kind of refining or moving closer to the things that you eventually discover you’ll be better at. So that’s really good. 

Lisandra: I just want to add that your actions—so I think that I missed my calling as a writer. 

Kerry-Ann: I’m waiting on that book now. I’m going to keep asking you what’s going on with the book. 

Lisandra: Right. So I love books. I love reading. I love writing. And so one of the things I’m doing right now to take actions towards the things that give me energy is, a Udemy course on writing and improving your writing style. I just finished a storytelling course on +Acumen, a free one, with my team actually, where we had to start presenting by telling stories, which just filled me with so much joy that I signed up for like 10 courses after that. All of that gives me energy. So just a little side bar that you don’t have to go to graduate school to continue your learning in the direction of the thing you enjoy. 

Kerry-Ann: Awesome. That is so awesome. Well Lisandra, thank you so much for being on the Carry on Friends Caribbean-American podcast. Thank you for sharing your journey. Really, the interview went completely different than what I, in my head, thought I was going to go. Just thank you for putting in perspective that our life can only make meaning when we are intentional about finding out more about who we are and not the what we’re supposed to be doing, and taking a page as much as we can from the European playbook or travel, work to live and not live to work—just stands out. Reminders that I could just calm down and do some self-care. If I don’t feel like doing something, I could watch Avengers and eat ice cream and just relax and pick up something. So thank you so much for sharing that. 

Lisandra: Yeah, that’s when you get your best ideas, when you turn your mind off.

Kerry-Ann: Boy, I tell you, you’re speaking to me this morning. 

Lisandra: We could talk for hours about this stuff. 

Kerry-Ann: So we could talk for hours, but we’re going to sign off. Everyone, again, thanks for listening and like I said at the end of this show and I love to tell everyone, walk good. 

Okay, friends, I hope you enjoyed this episode of the Carry on Friends podcast. For a recap of this episode and other great articles, please visit the blog at


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.