woman on a computer with a mic

Ep. 41: Your Questions Answered

[Updated Feb 2019]


The first episode where I answer listener questions!!

The Carry On Friends Podcast is were Career, Entrepreneurship and Caribbean Culture intersect. I asked listeners to send in there questions and I got great feedback. I selected a few of those questions and will do the other questions in another episode.

The questions were:

  1. When is a good time to quit your job to follow your dream?
  2. How important is strategy when starting or running your business?
  3. I also answer a listener question asking what I miss from back home (Jamaica) that I’m unable to get in America.

Do you have a question you’d like to ask? Email hello@carryonfriends.com to submit questions that may be asked and answered in a future episode of the podcast.

Email hello@carryonfriends.com for more information.

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[Updated to remove reference to the C+E Advisory Connect.] 


Hey everyone, this is Kerry-Ann, and welcome to episode 41 of the Carry on Friends Podcast. Today’s episode is a little different. It’s new for me. This episode is “Your Questions Answered”. I’m going to try it out. I asked a couple of people who I know listen to the podcast and reached out to them and asked them if they had any questions they wanted to ask me on the show and I would try to answer their questions. So I’m glad I got a couple responses. If it goes well – tell me if it goes well. I will continue doing this.

Before we get into the episode, please remember to share the love on Twitter, Facebook and Instagram. I’m not sure which platform you’re listening on, but we are on iTunes, Stitcher Radio, tune in and of course you could listen to the episode on the blog. On social media, we are on Twitter, Instagram and Facebook at Carry on Friends.

So now that we’ve got all of that out of the way, I wanted to share why I’m doing this episode. This is summer, people are still kind of hanging out. I think this is a great format to engage, submit questions and give them my answers on the particular questions that they have. The questions were either career based, entrepreneurship based or culture-based because Carry on Friends is we are a career and entrepreneurship and Caribbean culture intersect. So I’m very excited and I’m looking forward to answering these questions as best as I can.

My first question is a career-based question. At what point would you feel comfortable quitting your job to follow your passion full-time? Is there an age limit on that? So the easiest part of this question is no, there is no age limit. The harder part of this question is only the person making the decision about quitting their job knows what that comfort level is and that varies for different people. It’s really an individual question and there is really no right or wrong answer. If you’re going to quit your job full-time, you have to be strategic and classy about it. So strategic is because at the end of the day, quitting your job comes down to can I afford it. That’s the first reality, the first thing that I think about. Can I afford to quit my job full-time to do my passion? It’s a question because you lose the predictability of a salary, you deal with insurance and if you have a family, if you have kids, those things come into play. That’s a decision where you have to sit down with family and you have to figure out your responsibilities and how you’re going to be able to meet those when you don’t have that consistent revenue coming in. Do you have a certain amount of money set to the side and that you can maybe use as a cushion while you build your business? Questions I would have are do you absolutely need to quit the job right now, where are you in the process, have you already started this passion as a side hustle, have you gotten so much traction that at this point, you have so much business that you can stop your job full-time and do the side hustle because it’s growing into a full-time business. I know of people who have quit their job to do their passion and the side hustle and make it a full-time business. Is challenging, but they have done it because they’ve gotten to a point where okay, my business is here, in order for me to take it to the next level I have to give up on my full-time job.

That’s a decision that the person who is making the decision can best answer. I say classy because if you’re going to quit your job, and sometimes I feel like I’m saying this and it’s a given, but it’s not, classy is because you don’t want to burn your bridges when you are quitting a job. You always want to leave on the best of terms, you keep it above board because you never know if you’re going to need a reference, referral or something. So I would keep it classy that way. I hope that answers that question. One more thing, in terms of being strategic, you want to lay out like a three month, six month, one year kind of plan because I also know of people who quit their job to follow a passion and you know what? It’s not working out and so, they want to go back full-time. So you know having a plan to help you through this transition because it’s going to be a transition. For some people who are very lucky, they are up and running and things are going very quickly, and some people, it may not work. In the Caribbean, and I say it all the time to my kids, “puss and dog don’t have the same luck”. Not because something works well for one person means it’s going to work the same way for you, not because it went badly for someone else means it’s going to go badly for you. So it’s really, really looking at it from a holistic view, a personal and a business standpoint and seeing whether this is something you are truly comfortable with. Again, there is this thing about getting out of your comfort zone, but really it’s an individual decision and those who will be immediately impacted by the decision that they are making which is a spouse, a partner, children etc.

So on to the entrepreneur question, and I have a couple of them. So I’m just only going to pick about two of them because I really don’t want to keep this episode long, and maybe hold those off for another episode, because I still have a culture question and I want to end it on a really fun note. So for an entrepreneur question, the first one I have is how important is strategy when starting or running your own business? Some folks say forget strategy, I just want to execute. What do you say to them? To that person, I’m like that’s like jumping in a car without a map and say, “Yo, let’s drive.” A strategy is really important, it’s your compass and you need that. My personality is such where I am – in some aspects where it counts, I’m going to be methodical or it’s going to be about the structure because I know that without the structure, you can be floundering. You don’t know what you’re doing because you’re just winging it, and winging it when it comes to business may work in some points, but in terms of longevity, it doesn’t. So you need a plan. You need to have some kind of structure to make sure you’re maximizing your efforts. Then the other part of that, it needs to be iterative, you need to review it. 

When I talk about plan, I get it, not everybody is into business plans, but you need to write something down. It could be really simple. I do a little thing in Excel or I do a little thing in Word, which everyone can work for you. I use both depending on what my mood feels like. You could say three months, this is the strategy or it could just be one strategy. For example, at the top of this year, I said this is going to be a buss out year for me. I laid out the strategy for this year in terms of myself, the podcast, the brand. Some things require a lot of intention and effort and then those are seeds that you are planting and other seeds kind of sprout up along the way, or opportunities along the way because you’ve set a goal and intention. It’s really amazing what happens when you set a plan and you’re working towards it and things happen. If you’re just kind of winging it all the time, it’s much more difficult to even measure success because you didn’t create like a benchmark at the beginning, you didn’t say oh I wanted to do this by a certain amount of time.

So a strategy is also helpful to help you evaluate where you are and what else you have to do. I get it, some people, they aren’t into strategy, and I’m that strategy person. This is part of the reason why I’m starting the C and E advisory connect because I get a lot of these questions in terms of creating a strategy. When you’re in a situation, it’s very hard to create a strategy because you really can’t step outside it to see, and having an accountability partner, a buddy or a mastermind group, sometimes those help especially if planning and creating strategy is not a strength for you. You are just the one that goes out and implements and execute things, so balancing that out is very important. So yes, strategy is important because for you to execute, you need to know what the end result should be and you need a strategy to help you move towards that end result of whatever it is.

The next question is at what point in your entrepreneurship journey do you outsource work? Benefits versus costs. Now I can totally, totally relate to this because most of us, when you start up, you don’t have any money. I’m barely making money much less to put money out of my pocket to pay somebody. Maybe for the first couple of months, maybe a couple years, you can do it yourself, but at some point, you are growing and there is a lot to do. So the first question is, is this the best use of my time right now? I had to go through that last year. Am I the only person that could do it? Can I do it? Absolutely I can do it. Do I need to do it right now, or am I the best person to do it and is my time best spent doing something that no one else can do? But there are other things that I can outsource that will free me up time, because the cost and the benefit, yes I just paid somebody on Fiverr $10 to do something, but at the same time, I’m able to have a continuation and maintain traction and some kind of activity. 

The other thing is business development. You think of if I invest in this person to help me do this, it frees up more time for me to go out and do revenue-generating activities. That is really the key. You look at the systems you have in place. You look at the things that absolutely need you to do, things that you can automate and things that you need to get someone else to help you to do. The cost is you are going to have to invest some money in order to create opportunities for you to make more money. You have to invest in it first before you can see the benefits of it. Outsourcing work is really about, will this free me up to do an activity that helps me generate revenue for my business. If it’s a yes, then it’s just something that you say well, if I’m paying $10 or $75 to somebody for doing this project, then I need to make sure that whatever revenue that I’m generating, I’m getting $100 or something. So you can see either you want to break even, so at $75 or higher so you can break even with the cost of outsourcing someone, or you could get a little extra. That is how I view that. So I hope that answered that question.

Like I said before, I have two other questions, and these questions, they have some part b’s to it and I think it will take a little bit more time to answer these questions. I promise I will get to it in another week or so, and maybe get some more questions in the meantime. So for the culture questions, I will just end with this one: is there anything you miss from home that you are unable to get in America? If this is the first time you are listening, I was born in Jamaica. I’ve lived here for a very long time, over 20 years, but I went to high school in Jamaica as well. I miss a lot of things about home. I think the thing I miss a lot is just surrounded with food. There is something absolutely different about when you go there and eat the food. It does not matter what it is, even certain franchises, I would not call their names, but it’s just the way the food tastes. It’s so different. I miss that. I miss food. Whenever I go to Jamaica, it’s always about I want to go here to eat, I want to go there to eat, I want to go here to eat. I always come back with some – not some weight, a lot of weight on.

The other thing I miss is just the beach. I took for granted – I come from Montego Bay, so I’m very close to the beach. I pass it every day back and forth because I lived close to the water, and my dad and his side of the family, they literally live by the seaside. I just miss going to the beach. You take it for granted. When I moved up here, every summer – well, every time we went back to Jamaica, because you know you go back summer, Christmas, whatever – when I was younger, I didn’t spend as much time at the beach, but as I got older, whenever I go to Jamaica, I’m like my office is on the beach, you want to see me, come link me. I no longer went to go visit aunty, uncle, cousin this, I just stayed on the beach all day. I tell people, if you want to see me, this is where I am, come check me. 

So I definitely miss that and the vibes. When you are around family and you’re going back home, it’s just like this energy of fun and joke. I still have that here when my family comes over, we run joke. In Jamaica, we say we run bear gimmicks, which is just making fun of someone in a family setting. When it’s in Jamaica, it’s just a different energy, just this different vibes; sitting on the veranda, the breeze blowing, just cooling wherever we are chilling out. So I really miss that, the food, the beach and the vibes. So that’s really what I miss.

That is it for this episode. I really enjoyed answering these questions. If you have any questions that you would like me to answer on the podcast, you can always send an email hello@carryonfriends.com or you could tweet us at Carry on Friends and leave something on Facebook. I would definitely love to hear from you. So on that note, this ends “Your Questions Answered Volume 1”. Until next time, 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.