Kerry-ANn & Mikelah

Ep. 16: Is a Side-Hustle Right For You?


Seems like almost everybody has a side hustle or more than one. But is having a side hustle right for you?

In this episode we ask the question: Is a side-hustle right for you? Inspired by the post “The Rise of The Side-Hustle”.

We discuss:

1. Good reasons to start a side hustle;

2. When starting a side hustle is a bad idea.

3. Challenges to starting a side hustle and;

4. Where to get help as you pursue your side hustle dreams.



Kerry-Ann: So today we are tackling the subject, well the question rather of whether a side hustle is right for you and its inspired by the blog post a few months ago called the rise of the side hustle, and that was off course inspired by everybody having a side hustle, so let’s talk about it, Mikelah.

Mikelah: yeah I think, I said this already in the last podcast, living in New York everyone has like two to three. I don’t know anybody that just has one. So sometimes it’s really about evaluating if that life really is for you, are you pursuing something out of you passion, or I you are just, well everybody else has one I need to have one too. So I think it’s interesting the shift of people wanting to do more, having multiple and having multiple interest. I really think that that is where the rise came out of. I have my main stream, this is what I do, but I also have other passions outside of what I do every day that I want to explore and I think that exploring those it gives you the option to say, hmm, I really love what I’m doing and can I make money from this. A lot of people’s dreams are to take that side hustle and make it their only hustle. So I think that shift is really interesting but going through the groin pains of going through a side hustle and nurturing it along with whatever your day job and your nine to five requires and your personal life requires of you, can you do it and how much are you willing to sacrifice to have the side hustle.

Kerry-Ann: well it comes back to your initial point that it’s you passion, because there are going to be some low points, if it’s not something you are passionate about you are just going to throw it out the window really quick.

Mikelah: I think you definitely figure out whether it’s a true side hustle that you want to pursue in those hard times. It’s so easy to walk away because no one is putting the battery in your back to do any of it, so you can quite easily walk away from it and not feel any remorse unless you are really passionate about it. 

Kerry-Ann: so let us look at some reasons why a side hustle is good. We already explored one, which are you having passions and interest outside the nine to five. What are some other reasons why having a side hustle, passive income or multiple revenue streams as Pat Flynn would say.

Mikelah: my boy Pat.

Kerry-Ann: – yes

Mikelah: and if you guys have not heard Pat Flynn podcast on passive income, it’s definitely a must listen if you are interesting in the idea of passive income. I think reasons to do a side hustle, like we said we talked about passion, we talked about passive or supplementive income but also maybe you want to grow in a way that you don’t have the opportunity to do in your nine to five. I know with me personally, my blog was my resume piece in digital, because I was doing more of traditional stuff and it constantly came up in conversations and that allowed me to, it might now have the numbers but it has, it shows that I have the knowhow. It showcases what my skills are and it’s just me, it’s not like I have a team of people and somebody else is doing it for me. But it allowed me to understand digital from a much smaller perspective, because most companies they have an IT team, or a digital team or most likely have a marketing team who knows something about digital now. Whereas I’m, marketing, writing, PR, those skills, learning SEO, learning coding, how I can develop thins from little to nothing, and if I can get it from little to nothing, I was able to grow. So even in what I do now, I can make quick graphics or I can look at something and say, well we need this and the third, and this is what its missing from a consumer perspective, or the image isn’t tagged right and how, why can’t we get any data on this. I can ask the right questions because I have already went through looking for it, and I think another reason to really look into the idea of the side hustle is…

Kerry-Ann: ok while you remember

Mikelah: no it’s going to come back when we are like on the next topic

Kerry-Ann: another reason to explore a side hustle and it’s a double edge sword, but we did talk about massive income right. 

Mikelah: We didn’t go details bout it, we did touch upon it, but we didn’t. I think what massive income means to you and I might be very different. 

Kerry-Ann: so passive income my understanding of it, it’s something that makes money and you don’t have to be involved in how that makes money. So an example of what I think is a passive income is a vending machine, right. Those people the go out, they load up the vending machine and they have nothing to do, other than you go in you put your dollar and you get your product and out. That’s somewhat like a passive income; you are not necessarily had to be in the day to day for you to make money. Multiple revenue streams, that can vary, there is I mean side hustle out there start from coaching, which I do not like the term but coaching. There is coaching, there is consulting of a variety depending on what you are skilled at. The products, I have friends who sew, I have other people who make things. You are good with your hands, and it’s a craft so you sell those and so you have a products and that’s really it, product based and service based. So from those you can generate some sort of revenue. However you structure that, that’s entirely up to you. As a side note guys, I’m battling a little summer cold, so this little rasp and I might coughing a little bit off to the side, I’m getting over my summer cold. So in terms of is it a good idea, I am looking at it from the perspective of, we live in a very, we are approaching a new terrain with the economy and the job market and the job market is not like when our parents were going to school and we have unions and we have pension and everything is so different, and for me coming off 7 months of unemployment, a side hustle is a really good alternative to keep me busy when there is no real nice to five or to develop that side hustle for it to ultimately become a nine to five. So it’s a backup plan, a backup plan of it’s a formula of something I really want to be passionate about and something I’m really passionate about and I really want to make money off of it and its also, I see it as a part of my financial security for my family so a side hustle into that instance is good. I’ve known people who here side hustle supplements their nine to five because again, you are not making as much, it’s so competitive, you have so many people in the market looking for jobs and really it’s an employer’s market basically, so you have to figure out ways to supplement that income to support your family so in that instance I think the main reason why a side hustle is good to consider. Now we can look at the wrong reasons to get into a side hustle and the wrong one follows up with what I just said. If you are going to do it for the money then it is going to be a wrong reason to do a side hustle, because as we spoke about because there is moments where, it is very hard and if you are not making the money you think you are going to make going in, you are going to give up really quick, you are going to be disappointed really quick, because building a business weather its part time, side hustle passive income, its going to take time unless you have a ton of cash sitting on and you are going to go out and get a vending machine. You still got to figure out where you are going to place that vending machine to get a lot of money. So it’s not quick and easy as many people might make it seem, so.

Mikelah: I think the fast pace at which you can develop something, even if you are like selling a product, I see a lot of these wraps and green teas and you can sell them. But if you are not truly passionate about these products I think that it shows, are you just trying to sell us or are you passionate about the product and by all means, those avenues are great and they produce income for you, but again if you are not passionate about the holistic entire lifestyle that comes with it, that also shows. Not only that, not like you can’t be multi passionate, and have a couple of things. But you can’t do them all at one time. I can’t see you one week and you are peddling this and then the next week, you are peddling something else because really, you are a walking department store. So it’s completely, I don’t know how much I trust you now, because you’ve gone from someone’s opinion that I trusted to a complete sales pitch on a constant basis. There is nothing wrong with sales and pitching, I don’t want to put it in that context, but if you are doing too much, then it almost feels like you are doing nothing, so you have to be willing stick it out, exhaust all of your resources, all of your time all of your energy, ideas behind something specific, I mean the great people who do multiple things, they grow it, get it to a certain point and then go into something else. But then it flows with their portfolio of products that they are pitching. So it’s not like they are selling a car one day, and then all of a sudden, you ae selling hand bags. I get sales is sales, but if you are selling coaching services, and then you have a book that goes with that coaching service and then you so some sort of other product that is related, or you endorse a product that is related to you brand, really think about what this hustle is going to, not only bring to your table but what you are going to bring to it and how is it going to service people. 

Kerry-Ann: part of that is your reputation because your reputation is your most valuable asset and you know, you want to protect that reputation, whether it’s a product or a service, you have to build trust. So anything that you are selling or any side hustle that you are trying to get into, it should authentically represent you, because if it doesn’t, it’s going to show, you are not going to get clients and its going to go that spiral of no one supporting you, it’s not working out, its distressing and we get into that. So the wrong reason to go into a side hustle, only for the money and you are grabbing any product. Again it works for some people but not everyone, so it’s exactly why some people do great with Avon and some people don’t. Or Mary Kay because those who do great at it, they are passionate about it. Those who don’t, oh you are looking at someone who is doing great at it and…

Mikelah: it’s nothing more than you are getting a job, another job. So if you already have one job and you don’t have a career you are just adding job on top of job.

Kerry-Ann: and that’s important, even if you don’t have a side hustle it is still a full time job because you have to develop it. So the wrong reason to have a side hustle, number two we just mentioned it. I’m going to give the Jamaican version, follow fashion. Like do not copy what you see, other people success does not mean that carries over to you and I guess the same can be said that other peoples failure will not carry over to you. Is just that you have to go in it for the right reason, not because you see someone else is doing it, and that’s hard in the social media age of Instagram or whatever you see other people doing well and you want to try it too. Don’t look at what other people are doing you got to do it for yourself and what you can offer. What is the one that that you can differentiate yourself from what other people are doing?

Mikelah: yeah, and don’t look at others success and think that you can replicate it, don’t let this, the life that you perceive because you are not there 3 am in the morning when that person is doing the work, so although they might look like they are just hanging out with friends, or having a good time, they are all over the town, their Instagram look amazing, they are all over the place but you also don’t know the amount of work that goes into what else they do. Don’t measure your gaging whether you want to do a side hustle, on someone else being able to do the things that you want to do and thinking that’s you way to get there, I know Dame Dash did an interview with power 105 a couple months ago I believe and he was talking about the only way, the only thing he has ever done was to have his own business and he was completely down playing anybody that has the nine to five as a man and it was a lot of back and forth. It was an interesting conversation, but don’t hear ding dah speak and then he is telling you oh yes I’m putting down you all because Dame Dash told me, no keep your job and build your side hustle. His life style and how he came up is not going to be exactly yours. While they are some that are probably very similar, like that, it’s not for everybody.

Kerry-Ann: It’s not and I think we also have to keep in mind that not only with Dame Dash, but with anyone else, the circumstances, timing is everything. So the time they started it could be right, it could be wrong and the circumstances, everything affects when you determine to start a side hustle. It’s really important but at the same time you have to figure out, in addition to whether you are passionate about it, you know supplementing your income, you have to figure out the most important thing is whether you have the time to have a side hustle.  It is one of, or the biggest challenge to having a side hustle, time management. With the regular nine to five, we have a hard time managing time, much less adding on a second job again, even though it’s a side hustle it’s a second job and if you have a second job, it’s a third and so forth to dedicate. Because now you are cutting into your time, you have to either give up something or you have to cut back on other things. When considering a side hustle, do you have the time, where are you going to find the time to dedicate to the side hustle and in our work life, balance episode we talked about; maybe it’s not bringing on social media as much. Social media can be an important part of your sales process but you may need to cut back on the scrolling up and down once you are done. Engagement is great but you might have to cut back. Maybe its cutting back and DVR-ing some of the shows or watching them in the summer when there is reruns. 

Mikelah: Or staying home from that fete.

Kerry-Ann: Yup, no party no going out, no drinking, none of that

Mikelah: you can have happy hour at your house, by yourself

Kerry-Ann: pretty much, by yourself. And even with that, you might have to do it, you need the extra money that you need to put into the side hustle so you still might have to do that. 

Mikelah: You need that cash flow. 

Kerry-Ann: absolutely, because you know it, you paying hosting, you’re paying themes, you are paying for

Mikelah: someone to fix your site when it’s down.

Kerry-Ann: you got to be paying for a lot of stuff, and it’s not…

Mikelah: and it’s just for online business, if you want to do something that physical, where you have a location, or you have to meet people and really travel, you know you want to be cognizant of the issues that may arise that you need cash flow for. So even though, I think the digital age has low barrier to entry so they are so many but you still have to be able to maintain, you know those maintenance fees are not by any means a small pie. A small piece of the pie, it’s relatively small to have an e-space rather than a physical space but you make it work and you make the sacrifices in other areas like you said in order to finance your side hustle. 

Kerry-Ann: So we spoke about time management, we spoke about cash flow and let me back up on time management a little bit because a lot of the times when you start a side hustle is you as a sole-trepreneur, that’s another thing there and you now have to manage your productivity, your efficiency and setting up certain systems and processes and that’s going to be my shameless plug for my new side hustle that is coming soon, so stay tuned for that, but it’s important because, especially when you are running a business by yourself, you need to have certain things in place because without it you can make costly mistakes, you can lose money. You know if you make a mistake, you can’t pass that off to the client if it was your mistake. Or you overlooked something that should have been included. So developing a system and having some basic systems in place to run your business is important, so if you don’t have that you are going to run into a lot of challenges. 

Mikelah: yes that is definitely true.

Kerry-Ann – the other big challenge to starting a side hustle is mind set. Again that is going back to looking at what other people are doing, you feel insecure there are some doubt there, you are not sure, it’s like this merry go round for lack of a better word. You go up like yeh my idea is nice, I feel good about it and the next minute you are like man, I don’t  know if this is a good idea. And then there is fear, you know, I don’t know if it’s two of three days ago, I sent a text to Mikelah, I said Mikelah, I need to do this, but boy my belly bottom, I’m scared. Because part of having a side hustle or having a business, is putting yourself out there and that’s a scary feeling. You know why it’s scary? Because the idea of the potential rejection that is going to come. So mind set it like a huge deal, that’s why you have a lot of these coaches out there, because you need the reinforcement and the right mindset, or the ping pong back and forth of, between I feel good, I don’t know if I feel so good. That struggle is real, on a daily basis. 

Mikelah: it is, I think it’s hard to look at your ideas and business from an objective stand point so I think people ae turning to coaches and cheerleaders, if you will to kind of champion them. It’s not that they don’t have the confidence or they don’t have the idea. It’s just that they are a little unsure about executing it because like you said you are putting yourself out there, and you need to be able to channel that in a way where you can kind of like…once it’s out there I just think it’s like, you just need a shoulder to say hey, this is how I’m feeling let me get it out and maybe I can go back o how I’m feeling.

Kerry-Ann: Which is what, happens, it’s like oh my god, and I just need to tell somebody I’m having the jitters. 

Mikelah: Having your try, you got to have a try.

Kerry-Ann: you got to have your support team and that happens and also, because you are so close to it, it’s like it’s really personal, it’s like your baby. So someone else is just going to say, its fine, they are going to help you with whatever mind set you are dealing with and, but that mindset is part of the challenge, you have it every day. You might not hear the superstars talking about it, but they got their own people.

Mikelah: yeah and I don’t think that feeling really ever goes away. I think that if you ever try something new or learn something new, or experience something new, that unsettled fear sets in and then you just have to say to yourself. I’m here, I got the idea, I’m going to go ahead and do it. 

Kerry-Ann: and so the other challenge I think in starting the side hustle is really defining or fleshing out your ideas clearly to have like a really good offering and then finding your market which is big. You have your idea you need to flesh it out a little bit and then you got to find your market. I think that’s a big challenge that we will have because you don’t want to be in a situation where you are selling to the same people over and over again, that’s one challenge. So yeh, finding the market and flushing out the idea is another big challenge with starting a side hustle.

Mikelah: yeah I think also too even with fleshing out your market and identifying your demographic, don’t be scared to just go with the idea and then kind of see how your market falls into place. I think a lot of people start with the idea, oh I want to do this for everybody. And then they work with a few of those everybody’s and they are like wait a minute I can’t bring this in because I don’t, once you start dealing with a lot of people you find that who you don’t want to deal with or what you don’t want to do and in figuring out what you don’t want, you narrow down things and the market that you do want and that’s also a great learning experience. Those are the growing pains that come with having this idea and now flushing it out all the way. Most people think I have to have this 10 page business idea, I need to  get a loan, I need to do this, I need to do that, I need to at least have $10,000 dollars in the bank, and you don’t necessary need that to flush out who your market is. Survey your friends and family, see what the need or identify a need in the market, no matter how small or how big it is, I mean the home shopping network is filled with like new things, products, gadgets, all of those infomercials you see, that started out as somebody’s small idea. A vegetable peeler that does it in 4.5 seconds, somebody’s buying it because I see it in the stores, so you know doesn’t think that it has to be the final, or release it perfectly. Whatever your side hustle is, whether it is the service, or it’s a product you know friends and family are a great test. Test it on people you don’t know as well, you know you’ve done surveys.

Kerry-Ann: yes and you know, I think in doing those surveys it can help you determine whether you should push forward or kind of just like stay put.

Mikelah: and sometimes a market isn’t ready for what you want to present. I mean look at Steve Jobs with apple, it took him forever to really get it to a place to where he was proud of. It took him years and that was his one hustle.

Kerry-Ann: and I mean also, there can be limitations, as to technology, right. Now w have the I- watcher, know we’ve been seeing it on side trek or some sci-fi movie back in the 80’s right.

Mikelah: living like the Bensons. 

Kerry-Ann: so sometimes the technology and what you need for an idea is just now yet available for you, so there are a lot of different things. As we wrap up I just want to touch on something Mikelah said. We get these ideas, that we need a very elaborate business plan; we don’t need any of that. We need to have some kind of summary, maybe one page or two pages as to what it is you want to do, but it doesn’t have to be elaborate, you don’t need the financials in there, you know, you just have to make sure its clear what you are trying to create or what you are trying to do and the other idea, the other thing in terms of starting a side hustle. What you go in as the initial vision, is not always going to be that vision, it doesn’t have to be perfect you just have to accept that it’s going to be different iterations of it as you go forth. And iterations are good, It means that your refining, you are getting better, so it does have to be perfect on its first go and that is why I like that book, “Rework”, I did a review on it, it shows, you just want to put it in market, like you said Mikelah, test it out and ten refine it and then come back and do it better. You just have to step out in faith and I just have to take my own advice so hopefully in another month or so I’m stepping out in faith. 

Mikelah: September, 2015.

Kerry-Ann: yes, coming soon

Mikelah: coming soon

Kerry-Ann: so ummm, so as we wrap up, so where can you look to find support if you are looking to start a side hustle?

Mikelah – I think definitely finding meet up groups, industry professional groups, on Linked reach out to people, email them, have breakfast with tem, have coffee, start to pick peoples brains in terms of, it took me a while to find you and I’ve been doing this whole blogging thing for a very long time and I have a small tribe of bloggers now and it’s just now I’ve been blogging for almost 8 years and it’s just now that I am really finding that tribe that will keep me going. It’s in the last I would say year and a half two years or so, that I’m really, like ok I have my cliché and if I have issues I can go to this person, that person and we all are very supportive of one another. We are continuously sharing links, or giving you this idea for this template, and those things really keep you engaged in your side hustle because let’s face it. Your friends or family may not really understand what you are doing or what you are going through. Even if you really do express it, you know Kurt is not the most tech savvy person, so I can tell him exactly what’s going on and he will listen and we will be like ok, but he is not going to suggest anything because it’s not his world, so his support comes in a completely different fashion, then sometimes I need more than just a pat on the back and know it will be ok. I need, “get yourself together, just write this blog post and keep it moving”, “or launch this thing and keep it moving”. 

Kerry-Ann: and that’s important too because I have had situations where people are like oh my family isn’t supportive. It’s not that they are not supportive, it’s just that they don’t understand and you have to make sure that you understand that your family is there for emotional support, they are your sounding board, but they are not going to tell you what to do. 

Mikelah: but at the very same token, if they don’t understand and they are our demographic, then you have like, it’s almost. So you can, like my mom just recently starting reading my blog, she is like so that’s a nice little website you have there, and then it’s not like I told her to read it, but now she is actually engaged in it because she is spending more time online. So I don’t expect that of my family or friends but I will talk about marketing ideas with her and sometime they will give you a certain insight that you are not even thinking about and you almost take it for granted that they don’t understand and there are time that they do. So don’t stop telling them.

Kerry-Ann: like Mikelah, I’ve been building my tribe, I would say for the past year, so this year will be two years since I’ve been blogging. Since I went to blog conferences last year just started building my tribe.

Mikelah – I told you about blog conferences, it’s a great way, that’s a great way to connect with people

Kerry-Ann: connect with people on twitter or conferences, I’m almost sure that for most thing that you are trying to do there is a group somewhere, there is a chat, there is a group on Facebook, there is something that you can connect to people. Reaching out to a set of people that you trust, you admire their work and you have a group going and it’s not enough to build a tribe or be a part of the tribe, be active.

Mikelah: yeah, be engaged.

Kerry-Ann: give information and you will get information, that’s just kind of how it goes. That’s just some of the ways to get your started in considering your side hustle. I mean get a team, get some support somewhere, as much as you are by yourself you can’t really do it alone. I hope that this episode was helpful as you embark on your side hustle or decide whether or not a side hustle is for you and you know, you don’t have to but if you are considering it I hope you enjoy it, you find the information helpful and we will catch up on the next episode. You can tweet us @carryonkerry and Mikelah @styleandvibes or @missMikelah so thanks for listening.

Thanks for Listening

Thanks so much for joining us again this week. Have some feedback you’d like to share? Leave a note in the comment section below!

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Connect with Us:

Mikelah: @Styleandvibes | @mikelahkrose

Kerry-Ann: @carryonfriends | @carryonkerry




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.