In this collaborative YouTube video, Matt Ragland and his coworker Charlie (CharliMarieTV) discuss the nuances of maintaining side hustles alongside full‑time work at ConvertKit. They explore whether side projects must be monetized or can remain purely for creative fulfillment, share personal motivations for keeping side hustles "on the side," and examine how side hustles can complement a primary job. The conversation includes real‑world examples, such as a teacher who uses a side hustle to fund his passion, and addresses three audience‑submitted Twitter questions: (1) Should all side hustles be monetized? (2) What to do when a side hustle could become a main hustle? (3) How to manage side hustles without burning out. Throughout, they emphasize balance, intentional time management, the importance of aligning side work with personal fulfillment, and the value of documenting the process to demystify the journey for others.
Questions this video answers
Charlie says she barely monetizes her side hustles, using only occasional sponsorships, and feels no pressure to earn money because her full‑time job covers her bills. She believes you shouldn't feel forced to monetize, though you should get paid for valuable content. Matt agrees, emphasizing that side hustles can remain passion projects without immediate financial pressure.
Charlie advises checking personal fulfillment and considering the extra admin work (e.g., sponsorships, finances). She would keep it enjoyable and only scale if it aligns with her goals. Matt adds that enjoyment is key; he reflects on his own side‑hustle experience and notes the importance of team collaboration and problem‑solving that he gets at his day job.
Matt stresses understanding your available time, clear communication with family, and dedicated planning of ideas. Charlie highlights balancing life, avoiding pressure to grow too fast, enjoying the journey, and giving yourself slack to prevent burnout.
Chapters
Hi everyone, my name is Matt and welcome to my channel. I'm so glad that you're here today because I have my first collaboration video with my friend and coworker from ConvertKit, Charlie. Charlie has an amazing channel that you should totally check out, and in the video that we have today, we talk about side hustles because we both have side hustles. We both work at ConvertKit, and one of the things that we talk about— should all side hustles be monetized, or can you do something for fun growth practice and it still be okay? Is it okay to keep your side hustle on the side? We also talk about burnout and time management, and how do you manage side hustles alongside full-time work and not burn out. So check this entire video out. Also check out the video that I did with Charlie on her channel. That's going to be linked below and above. Really glad that you're here. If you're here for the first time watching my channel, there's a lot of what I talk about is creating and cultivating a side hustle that is meaningful to you. So I hope you'll subscribe and continue to check out some other videos. Hope you're having a great day and enjoy this video between myself and Charlie. Thanks everyone. Matt here. I hope you're having a great Great day and welcome to my first collaboration video. I'm really excited to have my friend and coworker Charlie here. We work together at ConvertKit and she has an amazing YouTube channel where she— well, why don't you tell us what your channel's about?
Well, I'm the designer here at ConvertKit. I'm the marketing designer and I talk about design on YouTube and my life as a designer in London.
You're such a good teacher and you really explain things well, but what I really like is I like seeing how people who are working full-time jobs and enjoy those jobs still have these side hustles where they're fulfilled and they want to keep doing them and it's consistent. And you're sharing not just about your side hustle, but also your job and how that fulfills you as well. And that's something that I think to me is kind of underrepresented in side hustles.
I think so too. I feel like often there's this sense in all of the things that you read about like how to start a side hustle or whatever, it's always about, "Oh, you're going to do this until it can be full-time." No one really talks about the fact that your side hustle can just stay on the side. So we're going to talk about it.
That's how both of us feel. We were talking about it along with some other people that we work with that it's something we're like, "Wait, we don't really want to quit to do any of these things." But it is something that fulfills us. It's a creative outlet. The work that we do at ConvertKit, which is helping creators build an audience and make a living off the things that they care about. In a way, we get to practice that as well.
I think that it all fits together and your side hustles become a part of your career in a way because it's part of you and what you do, especially if you work somewhere like us where your company is very supportive of your side hustle. I can definitely see how others would not feel that way and might worry, you know, that you're going to then leave and doing this full-time. It's alright if you wanted to keep your side hustle private from your workmates. Just on the side.
For me, I want to continue to do a side hustle because yes, it does fulfill me. But I would never want— sometimes people feel like maybe they want to leave a job for, say, maybe they're happy where they are, but they're like, gosh, I could make so much money, so much more money going somewhere else. It's not that you have to monetize every side hustle. We're going to talk about that in a second. It can be a way that if you're monetizing a side hustle on something that you care about and something you find interesting, then that supplements the thing that you are really excited about doing in your day-to-day.
Definitely. So what I've figured out, like, over the past few years is that I need several things to feel fulfilled, and I can't get them from one role. Like, so I need to be designing first and foremost because I'm a designer and like, that's what I love to do. So that's what I do at my day job at ConvertKit. I also need to be teaching and connecting with people, and that's not really— I wouldn't be hired at a full-time role to both design and teach. I wouldn't be doing enough of either of those things almost to feel fulfilled, even if that was a role, because I wouldn't be designing full-time. So I get that teaching side of things through my YouTube channel and through speaking at events and things like that. I also like to make things and just explore design as art in a way or just for fun, you know. And I have an online store where I design t-shirts and prints and sell them there. And all of those things come together and like make me happy and make me feel like a fulfilled creative individual. And if you take away any one of them, things start to like feel a bit off and I don't enjoy any of the things as much. So, I need that balance and I think figuring out that balance it's tricky, but it could be a reason why a lot of people feel unfulfilled in what they're doing. It might not be a case of changing jobs. It might be a case of adding a side hustle.
Another thing that came to mind when you're talking about this is we have a customer at ConvertKit, Dave Stewart, who's a teacher and just like Teacher of the Year kind of teacher, and he makes more money on his side hustle. It's been in his teaching job, then his teaching job. But it's something that, like, because that happens, he's able to continue teaching, which is his passion, with this, which is his passion. And he wouldn't— he'll never have to worry about, like, oh my gosh, I'm gonna— because I've seen so many friends who are in teaching go do something else. You're like, I gotta make more money, man. I totally get that, totally get that. But like, for Dave, he was able to do this. And I, you know, That's always something that I've really admired. So we've had a few questions from Twitter.
Yeah.
Thank you for asking, people. We both did. She got some more responses.
Thanks, tweet.
The first one, shared friend Corey Miller. Corey asked, "Should all side hustles be monetized or can you do something for fun growth practice and it still be okay?" You want to take the first crack?
Definitely.
Yeah.
Definitely. I barely monetize my side hustles. I would say, like, a little bit through YouTube sponsorships every now and then. But what I love is that I don't have to feel pressured for those side hustles to earn money because I have a job. I feel like I can protect them a little more and be really picky with what, you know, monetizing things I do. I don't have to be at the mercy of AdSense, which YouTube has been having a lot of issues with lately, because the full-time job covers my bills. So anything I earn on the side hustle is a bonus. I do think that you shouldn't leave money on the table. I mean, you deserve to be paid what you're worth and be paid for the content that you're putting out there. Right.
I certainly share that opinion.
Yeah. But you shouldn't feel pressured to monetize your side hustle.
Yeah. I agree. I think it's the other side of that coin that we just talked about with Dave where I love that people can continue to do things that they really care about. And not have to worry about like, "Oh my gosh, when am I going to monetize this?" or "How am I going to monetize this?" Like you said, you can be patient. You can be careful with it. You can give it the time that it deserves rather than trying to like shove something through maybe before you're ready.
And then I think it keeps it fun as well. It doesn't make it another stress in your life, you know, worrying about the financial side of things.
Totally. Your friend Inez and mine, even though we've never met, Inez asks, "What do you do when a side hustle looks like it could grow into a main hustle?" And I think this is a great question. Well, I wonder what you think about it.
I think, like, I take her question to mean, for me anyway in this situation, it would be a decision that you have to make. You know, do you want it to be a main thing? Because just because it could be, doesn't mean it has to be. It's really important. So checking in with yourself and thinking about what fulfills you. Do you actually want to do this thing full-time?— if I was going to do my YouTube podcast, you know, content creation as my full-time thing, I would have to get real smart about sponsorships. I would have to, you know, be all up in the finances and that sort of thing, lots of admin that I do not enjoy. And so I would rather keep it to be the enjoyable thing, and if the odd sponsorship comes along and it's the right fit, then I'll do it. But I don't have to worry about finding that and, you know, working in that way. So just think about what it would mean What would change about your side hustle if it was to become full-time?
It's a good way to think about it.
Yeah. And would it stay as enjoyable as it is now?
I think that enjoyment factor, because one of the reasons that we enjoy doing our side hustles is because maybe we get to just focus on the thing that we enjoy with it. And one of the things that— so I did kind of side hustles freelancing for 2 years leading up to working at ConvertKit. The thing that really struck me during that time, and I'm glad that I took the time to realize it, is that I really enjoy working with a team and with other people. And I even like working on a, like, on a single product solving a big problem over time with a bunch of smart people. And that's what I get to do.
And you perhaps wouldn't have those same level of problems in a side hustle for perhaps maybe like 10 years, you know, if you were building it up by yourself. Oh yeah. But because we are a company, we're a software company, we've got lots of users, you encounter all those problems that you then get to solve.
Every day. So our last question comes from Danica, and Danica asks, "How do you manage side hustles alongside full-time work and not burn out?" So for me, that is— we actually talked about this on Charlie's channel as well, so we'll link to that video right below. It's an important question. We'll give a lot more detail in that video. But the thing that I believe is really important, I'll just give you the quick synopsis, is really understanding your time. And for me, as you all know, I'm married, I have a 2-year-old, Kanan. And when you involve other people like that, then you have to be really clear about your time and what your intentions are. And you have to be really dedicated to those times. And The second part of that, besides the communication piece, is really capturing your ideas and planning them out as best you can. So when you have that time to side hustle, you're just sitting down and you're getting right to work. Or some of the other things.
Those are really good tips. The time management side. On the burnout side.
Yeah, I'm glad.
I think it's easy to feel a lot of pressure with your side hustle, especially when you see a lot of other people taking a side thing and making it their main thing, there's that pressure to grow it fast, to be really successful like immediately, and that adds a lot of stress and it makes it easier to burn out because you're going to work longer hours on it, etc. Think about what your side hustle means to you and what's important in your life. And if it is important enough for you to spend every waking hour on it, then great. But for me, I like to live a balanced life. I like to have time off and I like to— like, it's the journey, it's not the destination, right? So you've got to enjoy the getting there, and if you're burnt out all the time, it's probably not going to be worth it. So cut yourself some slack. It might seem like everybody else in the world is like working harder than you and like achieving more, and you should be working harder.
I don't—
do you feel that pressure?
I feel— oh yeah, totally. We were talking about it earlier. I was like, gosh, I got to get some more subscribers. So now, like, Mr. Bunch of Videos with No Subscribers person, like, that's the thing.
Yeah, and this is something we compare ourselves Like, we can't help it. That's— I think it's human. Burnout can— like, that can lead to burnout because it's gonna put a lot of pressure on you, and you're putting pressure on yourself. Once you realize that, I think you can hopefully ease the pressure off of it as well. It's a side hustle. It's only you really that's accountable to it. So if you need to take some time, exactly.
I think the more that you document your own process, not only will you look back and see like, these are all the things that I've done, and feel really proud about that— I hope you feel proud about that— but also you're going to start to dissipate some of those myths for other people that think it just happens like that. And like, oh, you can see Matt went through this, Charlie went through this, and this is how their side hustle, this is how their channel, this is how their audience developed. And it's really easy to compare your beginning, your middle, to someone else's end journey. Maybe not end journey, but like, don't— if you're on step 2, and that's okay because everyone's on step 2 at some point, Don't start comparing yourself to someone on 8, 9, 10, whatever they are further, like just further down the line. That's okay. Trust yourself in that process in getting down the journey.
And everything always looks easier than it actually was. So yeah.
I get feedback from people like, "Oh, this looks so effortless." I'm like, "What?" I put so much work into this. Okay. Yeah. Super easy. And I think one of the things that I want to do with this channel also is to document the process so that it does share, like, this is what it's like. This is what it is. Yeah.
I would say we both do work hard. We both enjoy what we're doing and try and live a balanced life as well. And side hustles are a part of that.
Exactly. Well, thanks everyone for watching. Make sure you give this a thumbs up and subscribe if you haven't watched it before. And make sure you go over to Charlie's channel. We'll link to it above and below. For everything here, but she does amazing work. And can't wait to see you next time. There were some other questions on Twitter, and I'm going to be doing more videos answering those because I think they were really valuable. So thanks to everyone who submitted a question, and thanks so much, Charlie.
