122: Freelancing in Support with Jenny Dempsey

122: Freelancing in Support with Jenny Dempsey

Jenny, who was my first ever guest, returns to talk about how her side hustle became a full-time job, and how she’s had to find a balance that works for her.


I’d love your thoughts on this episode! Comment below, and like/love/share/support if you found this inspiring, thought-provoking, or useful!

Charlotte Ward 0:13
Hello, and welcome to Episode 122 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 back to the podcast today. Jenny Dempsey, Jenny, it’s been a little bit of a while since we last spoke, but absolute pleasure to talk to you again. And I think things have changed up a little bit for you lately, haven’t they?

Jenny Dempsey 0:47
Oh, they have? Yes. A couple of weeks ago, I started a new role as the consumer experience manager or a field sciences. And I am also the customer experience manager for fruit stand. And so I am working now in a technology industry that focuses on produce and sustainability and supporting farmers and helping consumers enjoy different types of produce while supporting these small farms across the country. So it’s really exciting. And lots of a lots of adventures come along with starting something new and a new industry that I don’t know, like the back of my hand. Oh,

Unknown Speaker 1:28

Charlotte Ward 1:31
That’s awesome. Well, congratulations first. And I know it wasn’t necessarily a direct route, because and one of the reasons that you’re here to talk to me today is because we’re, we’re talking about freelancing in support. And I know you were doing this for a while, before you landed this role. So should we kick off a little bit of a chat about freelancing and your experiences there?

Jenny Dempsey 1:54
Yeah, absolutely. And I’ll start it off by saying that it’s been a year that I have done freelancing, and at the beginning, I had nothing, I had no idea what I was getting into. And I kind of reached out to some folks in the industry that do freelancing full time, and got a lot of great insight. But where I was lacking was, I wasn’t really finding folks who do freelancing, but also hold a full time job. I’m one of those people that I like stability, but I also love to have a project on the outside that I can kind of be a little creative with. So I took on place was like last August, August 2019, I took on a contract role for a fruit stand. And it was supposed to be six months, I was going to build the customer experience department. And then that was it. And I set some goals around that. Because I was like, I know, this is going to be more time I’m already working 40 plus hours. And now I’m going to be working more. And so you know, with a focus on like self care and making sure that like, I’m not overworking, I had to set really strict goals around why am I doing this? Why am I putting more time into it. And I’m gonna be super transparent. One of my goals was that I wanted to have an extra extra, you know, bucket of money set aside. So this was pre COVID. So I could travel for a month in Europe. And so I took on this role with that goal. And I was very structured about the time and then when it comes time for it to end and I’m supposed to go travel and enjoy this month, the contract is renewed and I had the opportunity to say yes or no. And I decided to say yes, simply because I learned that I really like having that bucket of money on the side. And I also really enjoyed what I was doing. It was something new and different. The industry I worked full time in and I had been in for almost a decade, I knew really, really well. And so for me it was a matter of this creative outlet and learning something new and also having some financial backing. In the meantime, other projects would come up maybe a webinar here and there with another company or a speaking event. And so these also kind of became additional additional jobs basically, technically, they could be considered freelance, but more like project based. So I had a lot on my plate then COVID hit and changed the game and, and but it made me realise that like, time is the time and energy that you put into work. I know it’s different for everyone. But for me, I kind of pour my heart and soul into everything. And I started to see a significant decline in my like mental health in my physical health simply because even though I was enjoying what I was doing, I saw how spending 10 plus hours a day on the computer and when you can’t go anywhere else outside and really affects you and so I had to like really revisit what are my goals here? And that really kind of became a common theme when it came to freelance and stuff. What are my triggers Goal, what am I doing here. And then as time went on, and I, just about a couple months ago, and an opportunity came up to work full time, and for the company that I was freelancing for the head company that works with roots and his appeal sciences, and so I was able to, I gladly, you know, took that opportunity. And I, you know, it’s, it’s a game changer, it’s a game changer to be spending time focusing on one thing and to not know, or to know that there’s not additional work outside of that unless I choose it. And I feel very lucky in that case, but it was a lot of learnings over the last year, and I realised that I just Yeah, I like having a stable, stable job. But I also really liked doing that job with the creative outlet. So now I feel like I kind of have this wonderful opportunity to do both in one. And it’s, it’s exciting, but it came from a very long journey of figuring things out and not having a tonne of resources to be able to do that.

Charlotte Ward 6:07
Yeah, yeah, that makes sense. You raise some really, really interesting things that, first of all, the flexibility and freedom that it gives you to pick and choose what you want. And secondly, the the learning opportunities that freelancing can present it to anyone who kind of it comes, I think, from that ability to pick and choose, right, if you’ve got the luxury of it not being your main income, you can be fussy about what you take on. And you can take it on for any number of reasons and learning, I think is definitely one of them. And then the final thing is that structure that you had to buy, to kind of the day to day, like as time went on, so I mean, I think I like particularly I’d like I’d like to touch on kind of the learning aspect and the structure. I mean, how did you? Was it like, was it a little bit like going back to school again? When when? Yeah,

Jenny Dempsey 7:07
yes, so much like going back to school. And, and, and it was advanced without mud, many study guides, like it was just like, yo, here you go, like you’re hired, especially in freelance roles they hire you on because you are supposed to be an expert in this particular area, and you’re supposed to know how to do everything. And being my that was the first time that I had done anything like that. And I don’t consider myself an expert. So but I consider myself like, I know things through experience. So when I jumped into that, and they’re like, well, you’re the expert here. I was like, oh, gosh, like it was slightly terrifying. And, and yeah, I had leaned a lot on the customer service communities support driven cx accelerator, and, you know, really like asking questions like, how do you guys do this, and feeling like the newbie on the block, when, in my full time job, I’ve been there a decade or you know, over a decade in that particular industry, and really knowing it, like the back of my hand, and then suddenly, like, yo, here, I’m supposed to be an expert in this. But I really know this. And like, it was just quite a jumble of learnings along the way. And,

Charlotte Ward 8:15
yeah, finding ways to draw the lines between what you do know and what actually, like seems scary at first, but isn’t really a million miles away. I mean, if you’ve been in support long enough, we all kind of accept that everything is a little bit different everywhere. And I think once you once you’re willing to accept that, you know that every team, every role is going to be a bit different. There’s always going to be learning, you know, yeah, and I yeah, I think that’s that’s kind of what I’ve come to appreciate over the years is feeling like this story in this kind of strange kind of double headed monster of the newbie, and the experienced person in the room at the same time.

Jenny Dempsey 8:54
That’s a very great picture. Right. And it’s so it’s so true.

Charlotte Ward 8:59
Yeah, I mean, nobody needs to picture me with two heads. But sure, I seem like I’ve got two heads on the best of days anyway. But the other the other thing that you talked about there was was the structure that you kind of came to apply and the kind of as part of that kind of self care and as part of just being able to get through the work, I guess, as well.

Jenny Dempsey 9:19
Yeah, it was a new experience of learning how to set boundaries and especially for you know, freelance roles when there’s typically like, if I were only doing freelance roles, it’s mostly my time I get to pick when I work and I get to do it, but because of it had the structure of a full time role and a very strict schedule of like, you know, nine to five type situation and I had to make sure that everything I was doing for the freelance role did not impact anything I was doing in the full time role. And also being so clear with my management at the full time role that I took this opportunity on and I’m you know, pretty transparent. I prefer over communication because why not? And Um, you know, so I was very clear, letting them know that that’s what I was doing outside of it and how it would not impact anything because you know, if they see something on LinkedIn, like, it’s always good to just like communicate that and they were open to it, which is also a plus a lot of companies out there might not be open to someone who works full time to have outside, they were definitely supportive and open to it. And, and then I had to figure out the rest of the structure. And so sometimes I would do it in the mornings before I started my full time job. And then I would, you know, I was like, This is too early. So then I’d go to the evenings and I’m like, oh, then I’m like, not eating dinner. And then, you know, then I’m working. I was working seven days a week, and, you know, 10 hours a day on Monday through Friday, and then, you know, a few hours every Saturday and Sunday. So then let’s talk about structure wise, I had to restructure all my exercise and, you know, kind of get outside type things, even if it’s, you know, only in small doses. And then social things like, let’s, you know, just because we couldn’t go out there were still zoom calls to hop on. But here I had been sitting at my computer already for 10 hours a day, do I really want to go back on the computer. So there were a lot of things around it that I had to factor in to, you know, restructuring and making sure that I took the best care of myself and I will 100% say, I failed so many times, like, and I learned from each one of those, like, there were so many days where I was like, yep, this is going to be an anxiety attack day, like I know it, I feel it, or some type of stress, or you know, I get stressed stomach aches or things would come up and I was like, Okay, this is teaching me something. What am I going to learn from this? And then I would have to go back and revisit, like, let’s see what the structure is. And where’s my mindset? Sometimes it’s not even about the day to day structure was like, Am I doing this for the right reasons? Is this really what I want to do? Is this worth it? I had to ask myself to Yes, there’s extra money, but is it worth it? What what costs, because there’s always a cost for it. So there was a lot of little individual things in that structure and the learnings that I had to just do I like there, there’s really no answer that I could Google, I had to just do it and figure it out myself and have a lot of pain in order to like, you know, figure out what it is what I really want to do here and I feel like that’s a privilege. And I know that’s a privilege and I want to acknowledge the fact that like, this isn’t it was challenging and ways but I also understand that it was a gift as well.

Charlotte Ward 12:26
That’s it for today. Go to customersupportleaders.com/122 for the show notes, and I’ll see you next time.

Transcribed by https://otter.ai


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