Charlotte Ward •

125: Freelancing in Support with Nicole Jackson

About this episode

Week 40 Topic: Freelancing in Support Nicole Jackson joins me for the first time, as we explore the balance between creating content and creating consultancy.

Nicole Jackson

Transcript

Charlotte Ward: 0:12

Hello and welcome to episode 125 of the Customer Support Leaders Podcast. I'm Charlotte Ward. This week we're talking about freelancing in customer support. So stay tuned for five leaders talking about that very topic. I'd like to welcome to the podcast today, Nicole Jackson. Nicole, it is lovely to have you join me for the first time to talk today about freelancing and support. But first, would you like to introduce yourself?

Nicole Jackson: 0:47

Yeah, thanks so much for having me, Charlotte. I'm happy to be here. I'm Nicole Jackson. I'm a consultant and contractor in the online customer support space. In March, I left my full-time salaried position to pursue a lifelong dream of being my own boss, and I'm loving it. You can learn more about my work and everything that I'm doing at solid supportstrategy.com.

Charlotte Ward: 1:12

That's awesome. Thanks so much, Nicole. Now, lifelong dream is is great to finally get there in this year of all years. Congratulations. So maybe you could tell me kind of first of all, why it's been a lifelong dream to be your own boss. What are you seeking out of this career move?

Nicole Jackson: 1:34

Yeah, so it has been a wild year for sure. And being my own boss is something that, you know, appealed to me since I can remember, since I was a small child. And I never really knew what that would look like and what I was going to be doing. And, you know, things became a little bit more clear in recent years once I felt as though I had enough experience in a particular area, uh, where, you know, somebody once told me, you know, when when everybody starts coming to you with their questions, you know you've got it. You know, you you've got something that to share with people, and it's time. And and, you know, I reached that point. And um I also learned that I have ADHD as an adult. And that also made things become a lot more clear. And I love being able to work in a flow that makes sense to me. Um, and you know, with my schedule, and that makes sense to my brain and my body. And uh, yeah, so I've been it's been going well.

Charlotte Ward: 2:44

That's great. So um it's been a journey, and it that there's that element of freedom and working in a way that suits you. So um, and in an area that you have developed expertise in. Um I I would love to kind of explore uh what happened next once you once you realized this was the thing, you had the expertise, everything was all of the stars aligned to make this the year that you did this. Um what happened next? What was your kind of opening strategy to get into uh freelancing?

Nicole Jackson: 3:18

Yeah. So I took you know a multi-pronged approach really, and I had a limited amount of time to kind of get things up and started. Thankfully, you know, I've been doing this a while. I know a lot of folks in this space. Uh, but the first thing that I did was get myself up on different freelancing marketplaces and just you know trialing a bunch of different marketplaces to see what they had to offer. Um, ultimately, I remain on one of those, um, and that's called Upwork. And uh I, you know, I've met a lot of clients through there. Um I've also you know done my own individual outreach when I come across companies that just seem like a good fit and found them that way. And I've also uh had folks reach out to me on LinkedIn and you know, we build a relationship there and and they've become consulting clients. So um it's really I mean, there's a multitude, you know, of ways that I've uh met folks so far.

Charlotte Ward: 4:24

Mm-hmm. And to identify particularly like one platform where you you're having more consistent results, I guess, in terms of the the quantity and quality of work probably helped. Um I'm kind of interested like in have you do you do you have a particular strategy, like how you package up what it is you do exactly?

Nicole Jackson: 4:51

Yeah, so I think you know, in terms of how I market myself, that continues to evolve. Um, you know, really I started out broadly in the beginning, you know, because you want to get work and experience and clients under your belt. And now at about this, just a little over the six month mark, uh, I I feel like I've reached a point where I am more clear about what I'm doing, what my customers are looking for. And I am planning on, you know, reevaluating all of that. Um thankfully, or at least I'm thankful, that I didn't spend a lot of time developing content in the beginning. I think that was a great tip that I learned in the beginning was you know, you can spend a lot of time developing content for lead generation, but the best way to get started is to just get yourself out there, and that can come with time and you know, build that alongside it, but don't wait for that in order to, you know, put yourself out there. So, in terms of you know, getting clients on those marketplaces, more important, in my opinion, than you know, the way that you maybe what you're including in your profile is the consistency in applying and you know, creating proposals for clients and just following up, right? Being timely and being really communicative, uh, and communicating in that message what you're going to do for them, you know, and I think that's really the consistency there is what has worked best for me.

Charlotte Ward: 6:38

Yeah. One one thing that I think is often a challenge when it comes to articulating what you can do on a support side for organizations is it's kind of it's a bit nebulous, isn't it? I think uh quite often organizations don't necessarily know what they want. So do you find that you're kind of as as part of that proposal process, maybe even clarifying what you think they need? Is there kind of a a bit of a kind of clarity that you need to bring before you before you win them over?

Nicole Jackson: 7:16

A lot of times. Yeah, that's a great point. And so, you know, your profile, for example, you can tell your story, but it's not really explaining to the client how your experience relates to their project. And that's why I think you know, the cover letter, the proposal, that's really your opportunity to create that story of exactly how it it impacts them. And yeah, I find that there's you know, typically, you know, clients will fall into those two buckets. Um, either they're really clear about what they're looking for, and that's great. I know that my job will be so much easier for it, and I really appreciate seeing that. And then maybe there are three buckets. The second one would be uh the the folks who are upfront about the fact that they don't know what they don't know, but they're trying and they want to be better and they're looking for somebody to help them with that. And you can again, I appreciate seeing that, right? They understand that they're not the expert, they want your expert opinion, and so great, you know, happy, happy to help them clarify. And then uh you'll see folks who are extremely vague, it's very clear they don't know what they're looking for. And those are I take on more on a case-by-case basis. Um, there's similar to, you know, helping a customer when you're doing support, there's a lot of reading between the lines of are they actually looking what they're asking for? Or, you know, can I read into this a little bit more and help them clarify or even you know, discover new opportunities that they weren't aware of before? Um, you're really doing the same thing and and just reading a lot in between the lines. So those, you know, I again, they're more of a case-by-case basis, and I'll judge it completely based on, you know, sort of the job description that they've created, whether or not to reach out and learn more.

Charlotte Ward: 9:21

I I think that's a really interesting parallel that ultimately what you're doing for clients on a freelance basis often is solving problems for them. And part of that um it is just a huge parallel to support, right? That we have to read between lines, figure out actually what that what it is this customer in inverted quotes is trying to do, what they're what the problem is they're trying to solve, and you help them get there.

Nicole Jackson: 9:46

Yeah, exactly. And you know, thankfully for those of us in this space, you know, we're really great communicators and we have so much experience doing that. And a lot of other folks and other jobs that are on these marketplaces, you know, you might not necessarily have had that same experience. So I really see it as a huge leg up.

Charlotte Ward: 10:08

Yeah, yeah, absolutely. So now that you're six months in, just touching on something that you said earlier about creating content and how you let you've left that to later in your journey and you took that advice to just get out there and start doing the work. What where are you now on creating content?

Nicole Jackson: 10:27

Yeah, so I'm really in a space right now where I'm, like I said, niching down further. And so really the brainstorm phase of what that looks like, things that I'm going to be removing from my plate. And um, yeah, so I'm very much in the planning phase of you know, the next quarter, what that looks like, and then thinking about 2021 already. What does that look like? Uh, you know, I've got projects on my plate now that I'll that I'll wrap up, but also thinking about where I want to be in 2021. And ultimately for me, that's more consulting, more strategy, and less executing. And so just, you know, finding um ways to to make that shift. Um yeah. So the content in terms of you know, the rest of the quarter for me will likely look like a few blog posts and you know, some email content for followers. And um, on the flip side of that, I've also been working on a podcast with a few other customer support leaders, and that's called Support Night School. And the mission there is really to share with folks who are trying to get into online customer support our best tips and strategies for getting into and starting in this space.

Charlotte Ward: 11:53

That's awesome, a fellow podcaster. Then I look forward to listening to that. Have you any idea when that will be broadcast? What are your plans there in terms of getting that out to people who want to get into this space?

Nicole Jackson: 12:07

Yeah, absolutely. So we are creating a limited series of six episodes to cover this topic. And we just wrapped up recording on episode five this past week. So episodes one through four are currently up and can be found on your major podcast uh platforms and also at supportnightschool.com.

Charlotte Ward: 12:33

That's awesome. That's awesome. Uh, congratulations on uh getting some out there already. That's I think I think like like you were saying, getting into podcasting, I think it just mirrors getting out there and consulting as well. I think you just kind of have to go, don't you? It's like you can really overthink it.

Nicole Jackson: 12:54

Absolutely. Absolutely. And this is something that uh, you know, we had been thinking about doing for a long time. And, you know, 2020 was the year to set out and do that for a few reasons. Uh, you know, one being that there have been so many people who have lost their jobs or taken pay cuts and are looking to get into something A, perhaps a bit more stable, um, that also is really remote friendly. So, pro tip for all of you listeners and customer support who are asked by friends and family also about what you do and how they can get started in this space. Um, that's really where this podcast was born from, was out of us being asked so many times by friends and family, um, you know, how how they can get started and get that same sort of flexibility and stability. So um it offers some great tips. And if you are sick of repeating yourself, also feel free to point them to supportnightschool.com and they can check out some great resources there.

Charlotte Ward: 14:00

I most definitely will. Thank you so much, Nicole. Great luck with the podcast and thank you for joining me. And and and good luck with like the continued journey into content creation and and really finding your niche in 2021. That's it for today. Go to customersupportleaders.com forward slash one two five for the show notes, and I'll see you next time.

A little disclaimer about the podcast, blog interviews, and articles on this site: the views, thoughts, and opinions expressed in the text and podcast belong solely to the author or interviewee, and not necessarily to any employer, organization, committee or other group or individual.
© 2026 Customer Support Leaders
Made with in the UK & AU