266: From Self-Doubt and a Factory Job to Freelance Biz Owner: Caroline’s One-Year Transformation

0:00Caroline Kuhlman was working in a sewing factory. She was exhausted, underpaid, and filled with doubt that she was ever going to be good enough to freelance. In fact, when she first signed up to work with me hands-on in my Fast Track Turbo program, she told me she just wanted to find some freelance work on the side. She said that if I had told her she'd be quitting her job in just one year, she wouldn't have gone for it. That leap would have felt way too scary. Because at the time, freelancing full-time didn't just feel out of reach. It felt impossible. But she started anyway, quietly on the side.

0:33And one year later, she walked away from that factory job and now runs her own thriving business as a freelance sample maker. This episode is about the courage to start when you're scared, the power of tiny steps, and how believing in yourself, even just a little, is sometimes all it takes to change everything. Oh, and you'll hear it right away, but Caroline and I had the privilege of meeting up in person to record this at a coffee shop. I have my nice mics, but you'll hear some ambient background noise. You're going to love this episode. Let's get to it. So can we start off like mega fucking celebrating that you quit your job in about a year from starting freelancing or what's the exact timeline?

1:14Caroline Kuhlman:So I started fast in June and then I quit my job in June. Oh, exactly a year. Yeah. Okay. Yeah, that's crazy. It is crazy. Because sometimes I think about, I got my first client in September. So it's September of 2024. Okay. And then I left my job in June 2025. Okay. So depending on how you measure it. And we're recording this September 2025. So it's one year date of getting your first client. Yes. Okay. So I want to hear a little bit about the, and you sent me a LinkedIn message, but I want to talk a little bit about the journey and the, I'm going to say, I don't want to put words in your mouth, so I'm not going to say that actually.

2:08The journey of quitting your job and going full-time into freelancing. And then we'll dig a little bit more into your backstory and the whole evolution. But I like to focus initially on, like, so what has it been, June, July, August? So three, four months since you quit. Like, talk to us.

2:29Caroline Kuhlman:Okay. Yeah. So I think I didn't know when, I didn't know how I was going to know when it was going to be time to leave. but the kind of mixture of events that helped me make the decision was there's one week where on Wednesday a potential client reached out to me asking if I was available and I had to say no to her because I was going on a work trip for corporate the next week and it was a short turnaround time so I had to say no to that and then the very next day another previous client reached out to me asking if I was available for a project and I was gonna have to say no to her as well because of yet another work trip that I hadn't said yes or no to but I knew was coming and I was the only person like who from our location who was gonna be able to go anyway so it was sort of I knew it was coming and I was like okay this feels like a moment where I have to choose my clients in these relationships that I have worked tart on or my corporate job and so so I remember I went I was I was yeah I was sitting at the sewing machine in like this windowless warehouse area where I had been working for like a year and a half and I went outside and it was like super sunny and I called my mom and I said this is what's happening

4:14Caroline Kuhlman:I feel like I'm ready to leave. And what do you think? And like both of our voices were trembling like this. And she said, I think that makes sense. And I hear you. And she's like, we're with you. We're behind you. And then I called a friend. And she also has her own business, and she had started a little bit ahead of me. She's a graphic designer. And I was like, she's a really straight shooter, so I asked her, what do you think? Like, these are the factors. You know, I feel like I have to choose between my clients and corporate, and these are the reasons, like I just said. And she was like, I think you can go for it.

5:14Caroline Kuhlman:So I was like, oh, my gosh. So that was a Thursday. And then I took the weekend to think about it. And then on Monday morning, I was leaving for that work trip that I had to say no to the first client for. and I put in my two weeks notice that morning before I left on the work trip. Oh my gosh. Did you like send an email or did you go talk to somebody? So there was a store manager at the location where I worked and so she was like, I directly reported to her and so I went into her office and I had my letter written up and I gave it to her and it was funny because she wasn't expecting me to come in that morning because I was leaving on the trip but I was like nobody had told me that I didn't have to come in just because I was leaving to go to Philly's so she was surprised to see me and then I wondered if she suspected something and I and I you know was freaking out but then I I did I went in there and um she she asked me why and she was she was like I'm happy for you so I wasn't expecting that at all and and then so I went I went on the trip and I ended up meeting some sales reps from some uniform companies while I was there and they were asking me, you know, we had getting to know each other throughout the week.

6:58Caroline Kuhlman:And, um, and so they, you know, we talked about like, how long have you been at goals? How long have you been at your job? And so it just came up about my business and that I was leaving. And, um, by the end of the week, like I had exchanged information with these two, um, sales reps from massive companies that I never thought I would be interested in hiring a freelancer. So the uniform, it was uniforms for public safety, military, and so state troopers, sheriff's departments, and police departments, and fire departments was the uniforms that we did at the company. and um the job that you had just quit right the day before the day of yes this now you're meeting these other people yes okay and so so there you know there there's like um government contracts involved and I never I just didn't see how a freelancer could fit into that and I hadn't seen it in any any um sort of small businesses or individuals working in that space in the year and a half that I'd been there.

8:16Caroline Kuhlman:So that was a total surprise and felt like serendipity that like they, you know, I had sort of, they had asked me questions about what I was doing and I had sort of almost been ready to talk about it in a way that made them ask me if I would be available to work with them. Like how, what was your thinking behind that strategy or like, how did you word that? So I don't, I think,

8:56Caroline Kuhlman:I think the, the work that I had done with you and with pitching and talking to clients, like I had sort of had my elevator pitch. So when they asked me, what's your business, I just kind of said I do sample making I do pre-production prototypes for brands and I like to work directly with pattern makers and so I kind of said my my spiel and then it it sort of was an organic I you know I was just telling them what telling them about myself not telling them like, hey, this is a service that I have. And so by the end of the week, it became, here's my information. Can I have your information? And so when I got back from the trip, like, I followed up with them and said, like, would you be open to a test project?

9:47Caroline Kuhlman:And they all responded to me right away. It was amazing. So are you working with them now? So there has not been a project that has come up. Okay. But it really was like a boost to me. that, because that was, that was, those were the biggest brands I've ever talked to, like huge, huge nationwide companies. Yeah. So that was,

10:15Caroline Kuhlman:that was,

10:19Caroline Kuhlman:because I felt like they had, we had gotten to know each other throughout the week and I hadn't, hadn't anticipated that that would happen by Friday. So it felt like just me being myself was sort of

10:38Caroline Kuhlman:enough. Yeah. And just me being my nerdy self and asking them like, what do your tech packs look like? And can I see the, can I see like behind the, like I just couldn't help myself but ask questions and stuff like that and ask them about, you know, when they do they were telling me how a lot of state troopers are like very very particular about their uniforms and want it to be really custom and so I was asking them about the process and they were telling me how they do they like to to do samples and sometimes it it is a little bit more specialized than than their regular production process is ready for and so we we're just nerding out about that and I think it felt like it felt sort of natural and I was like oh my gosh

11:38Caroline Kuhlman:maybe this it helped me feel like this maybe this is a special skill that I have that I that is valuable and and so thinking that about myself is is the milestone for me and making that decision and all those things happening within like a two-week period yeah it's really

12:12Caroline Kuhlman:I mean, life-changing sounds so dramatic, but really for me, from where I was in 2022, it's like night and day. Yeah, just three short years. Okay, I have so many questions. So first of all, you're on this work trip. So give everybody a one-liner about what you did at GALLS, because I think we don't have context yet. So GALLS does public safety uniforms, and I worked at a branch. so it was a retail location and also they they called it production a production facility but we were mostly doing hemming and applying sewing on patches so I was sewing there every day for about a year and a half so I got I I got faster and more confident with my sewing.

13:06So that was a valuable thing that I gained there.

13:12Caroline Kuhlman:And I needed that confidence in myself that that's a skill that I have. So that's what I did at Gauls. And so then you were on this work trip. And how did you balance the conversation of you're there representing Gauls on this work trip. Literally do they know the day before you just quit. and you're going full-time into your freelance business, like, how did you juggle that? And, like, hey, I'm a freelance sample maker, and, like, I'm da-da-da, but also I'm here representing my employer. So it was tricky because the regional manager, my boss didn't know if he was going to be coming and to be a part of the team on this trip or not.

14:00Caroline Kuhlman:And so the trip was going to police precincts to do fittings. And so that's what I was helping with. Okay. And so the regional manager who was over top of my store manager, she didn't know if he was coming or not, but then he showed up, I think, on Tuesday. And so I didn't know if she had told him or not. That you had just quit? Yes. Okay. Yeah, so I didn't know what information he was working off of and if he was irritated or what. Sure. And then he told me that he was upset for the first 24 hours, but then he was happy for me. Okay. I was like, okay, I'm glad we're in that. So then people on the work trip knew the context?

14:51Caroline Kuhlman:Yes. Okay. Yes, so just because it was people from all different branches coming together on this trip to work on this huge fitting project for all the police officers in Philadelphia PD. Okay. So just through the process of getting to know each other, it was like, how long have you been with Gauls? and um and so it was it was tricky I didn't know exactly what to say um but but sort of as the week went along and they were talking more about like sometimes the stores collaborate within Gauls and help each other out and so it just came up that I wasn't gonna be around anymore yeah um after one more week so okay so I kind of waited until I had some rapport with the people there to to say so it was like Thursday Friday where I was talking more about leaving and what my services are and because I had I had been open about it like that I freelance on the side okay so Gals knew this the whole time so I had I had yeah I had said that I also do do freelance sewing projects okay but I I um I didn't I had a hard time like with LinkedIn because a lot of the corporate people were on there and so I didn't know what was appropriate so I didn't really utilize that tool.

16:43Caroline Kuhlman:LinkedIn I didn't know how to navigate that but now I've been using it a lot and people are starting to reach out to me. LinkedIn has been so powerful actually even before I went kind of started really posting every week. Okay, so let's talk about the, this comes up with a lot of people. Like, how do you juggle LinkedIn while you're working full time? So Gulls did know you were freelancing on the side. Yeah, I had, I had told my boss that, um, that I think I said, like, I do freelance sewing projects on the side. And it was just a non-issue. And she didn't really react to it. So I, I mean, I kept it separate.

17:37Caroline Kuhlman:Like I only did the freelance work at home and the Gals work at work.

17:45So how come you struggled with like leaning so much into LinkedIn? You said it's because there's other corporate people on there.

17:53Caroline Kuhlman:Yeah, because we were in Richmond, Virginia. I worked at the branch, and the headquarters is in Lexington, Kentucky. Okay. And so we were quite separate from them, and I just didn't know how that would be received from their perspective. And just I think we and the branch felt like a little bit separate from them.

18:26Caroline Kuhlman:I wasn't sure what was okay and not, and if my boss being okay with it was a reflection of, like, the larger company being okay with it or not. Okay. But, because I know this because you and I worked together in Fast Track Turbo, like, you updated your LinkedIn headline, like, immediately to say your freelance sample maker. And you were engaging on there in some capacity. Yeah. yeah I think well before you quit right right so I had started I had started doing that and I'll never forget forget because we talked about my LinkedIn and then a pattern make a huge really successful pattern maker reached out to me like within 24 hours of me updating my my tagline and And I was like, whoa, this is so much more powerful than I thought.

19:22Caroline Kuhlman:So maybe it was more of a mental thing that I was.

19:34Caroline Kuhlman:seeing them separately and trying to keep them separate in my mind and not wanting to mix them together in a wrong way. I mean, I was definitely posting about Freelian's work. so yeah like I this is the first time hearing of this and we worked together like for eight months or however long like this is the very first time hearing of this so that was I was a little bit surprised but internally it's clear you were feeling it yeah so maybe it was more of an internal kind of tension struggle that that I was thinking and worrying about then

20:19um hmm I never saw or felt that on your LinkedIn okay I just saw and felt it as your freelance sample maker so this is interesting to hear yeah so okay so a big pattern maker reached out like a week or 24 hours after you changed your tagline so talk a little bit about like those early days and finding those first few clients and and your business is a little different in that your clients currently are more of the pattern makers as opposed to the brands

20:55Caroline Kuhlman:right so talk about some of that stuff so just like in fast I mean the customer research was huge that's how I learned um or that's how I decided what to put in my in my tagline was talking to pattern makers and I also talked to technical designers I talked to Jay Arbitman Arbitman yeah yeah he he's been on the podcast we'll link that in the show notes yeah such a good one so I I talked to different different people in the industry and I was like I want to do do sample making what um how do your clients how was their process with samples do they get them from their factory do you as a pattern maker sew them do you work with a pattern maker who sews them just on all these just I tried to ask as many questions as I could and be as curious as I could and and that was that was a good way for me to start gathering information but also talking to people virtually that I don't know because that was really, really scary.

22:08Caroline Kuhlman:I remember it was frustrating because I would prepare and plan, and you looked over my questions, and you were supporting me, but I was literally shaking every time I talked to someone. And so it was just my nervous system was completely overloaded, and it was hard to get through the conversation when my body's freaking out. But I stuck with it and kept doing it, and that was so valuable because I needed to understand sample making in the context of brands and freelancers as it's happening right now. And so what are the pain points? What are the... What does sampling look like at a factory that I could improve upon or help the brand be more ready and all the context of...

23:27Caroline Kuhlman:I lost my train of thought. That's right, you're good. The context. Yeah, the context of, like, Like, where does this piece of the puzzle fit in in the prototyping production process? Yes. So, like, you ultimately discovered that your niche socketed into the pattern makers are your clients. So, currently. Yes. The pattern makers work with the brands to create the patterns. Yes. And then for various reasons, they want to outsource the sample making. Yes. So even a super sample making is a big, almost like a hidden time, hidden big chunk of time that pattern makers are not losing, I'm trying to say.

24:24It's taking up a lot of time.

24:26Caroline Kuhlman:It's taking up a significant amount of time for pattern makers is making the samples. If they do that themselves, it takes up a lot of their time. So that's where I, that's the main thing that I noticed tonight. And so I said, I can help with that.

24:55and

24:56Caroline Kuhlman:So that's what I've been that was one sort of prong that I was one approach that I was taking and then I also was reaching out to design agencies and so I kind of explored that avenue and And that just turned out not to be the people who need my services. They're mostly going to their factories for the samples. Ah, right. So that was something that I needed to explore and learn and then sort of be like, okay, I'm going to focus on the pattern makers. And then I do, sometimes brands do reach out to me, but I have found that they are really excited to get a sample but they don't necessarily have their technical design and their pattern making to the place that I would like it to be to to make the best sample that we can and it'd be a good investment for them yeah so it has that has been a really good learning experience too is explaining, you know, why I asked for them to have a tech pack for me and to have the pattern.

26:19Caroline Kuhlman:Most of my experience on Upwork was talking to people who wanted me to make a sample without a pattern. And without a tech pack. And without a tech pack. And I said, they wanted me to, it was a good learning experience to see how they would phrase things. because they would say they would want me to sew from a picture. What does that mean? Here's this picture, make it. Yes, yes, or sew from an example or another garment that they had or a combination of things. So that was really interesting, and I decided, I kind of did two big pushes on Upwork where I was on there every day and sending out as many pitches as I could, and I never did end up working with any brands on there.

27:10Caroline Kuhlman:They were most, as far as I'm understanding, it was difficult because some of the postings had so little information to go off of, but I believe that they were all brands who were looking for sewing help in different capacities, and so it wasn't the right fit. Okay. didn't didn't result in a project but um now now if i go on there i can sort of see all right i mostly have chosen not to go on there and spend my time there because i can sort of see okay i don't think they're ready and and they don't have the um perspective that I have on what is a good approach to product development. And so we're on a different playing field.

28:05Caroline Kuhlman:They're still set on, like, they just, can't you just make a, sew a sample from the photo? Yes. And it's too, you're just on different levels of, like, or different, you're reading different books about, like, well, yeah, I could sew something, and, yeah, but it's not in the best service of them. Right. Okay, so it's so interesting, right, because you reached out to design agencies thinking that could work, talking directly to these smaller brands via Upwork. Both of those kind of hit dead ends. Right. But you found a sweet spot with the powder makers. So has that exclusively been your clientele to date, mostly?

28:49Caroline Kuhlman:I have, there has been one technical designer who was sort of maybe acting more as like a project manager. So she does design and technical design. And then she had hired the pattern maker and then me as the sample maker. Okay. So that was cool, and that was really good learning experience to see what is her perspective. And also her managing the project was a little bit different than when the pattern maker is engaging me for my service. So I think...

29:47It's been all with other freelancers, though. Right. Yeah. Right. I have not done a project directly with a brand. Yeah.