270: From Laid Off to Fully Booked: How Bre Replaced Her Salary in Under 2 Years

0:00Imagine getting laid off and 18 months later, you're making more than your old job and you are booked solid as a freelancer. That's exactly what happened to today's guest, Bre Simpson, but the road there was not easy. From grief and burnout to walking away from bad-fitting clients, Bre shares the unfiltered truth about what it really took to build her freelance business. In this episode, she walks us through how she went from a$250 tech pack to five-figure projects, the systems behind her success, and the mindset shifts that kept her going when nothing was working. Her story is proof that even when everything falls apart, you can rebuild something even stronger.

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1:04Let's get into the episode.

1:05Bre Simpson:All right. Welcome, Bree, to the podcast. I am really excited to hear all the details about your story and learn how you are on pace, on track. We won't fudge the numbers because they're going to happen soon. It's the end of October. You have two months left to finish this year, but on track to out-earn your previous in-house salary in your finance business in less than two years. So I want to dig into all of that. I guess to start out, can you give us a high-level overview of the pacing of, I know a little bit of the backstory, but left your job, building up your finance business, took some time.

1:44Give us a high-level overview of the pacing of what it's taken to get to where you are in the last 18 months, and then we can dig into some of the nuances and details.

1:52Bre Simpson:Yeah, totally. So I was laid off in April of 2024. And at that time was a longtime listener. And then it took me about 10 months really to kind of like go from zero to having consistent income that felt safe and secure and predictable. And now we're a year and a half in and it's safe, predictable and booking into 2026. So it's, it's taken a year and a half. Those first 10 months were really a grind. It was really throwing a lot at the wall seeing what sticks seeing what worked um between april i signed up for fast in june of that year so that april may june i was still like very avidly listening to like to your podcast and a couple other ones and then i think it was one of your webinars where you were going through i think it was like just tools to really help and i was like okay i'll listen and i'll listen in and and it's something just switched and i was like if i'm going to invest in something, I might as well invest in myself.

2:57Bre Simpson:And so, yeah, June I enrolled and now here we are like a year and a half later. And you are like in an amazing place, not without a tremendous amount of hard work and challenge and pain. And I'm sure some failures along the way. Definitely. Yeah, absolutely. Okay. Yeah. So there's room to breathe now. Good. Good. That's an amazing place to be. Can we start talking about those first 10 months and that initial building stage like what did that look like what were you working on what were you building out like what was it that you did that led to some of those first clients along those 10 months to get to the point where you were like okay I feel a little bit comfortable like not maybe so much like panic frenzy mode or not to put words in your mouth but I imagine no it definitely felt like it absolutely felt like a frenzy those first couple weeks right afterwards did have a bit of a panic energy um and then that first 10 months yeah like I said just a lot of like small building blocks to get to where I was so um you know I I will give credit where credit's due I remember talking to my dad and he's from a corporate background his whole entire life and he was very emphatic about like get your LinkedIn together because that's the first landing place people are going to see you.

4:15Bre Simpson:Um, cause at the time I didn't have a website and my personal, like my professional Instagram wasn't really up and running. So those two avenues where people are going to see me first were pretty lackluster. So, um, he was like literally the first person I called after I like walked out of the building. Um, and he was so sweet. And a real big thing that I think was helpful was I kind of, I texted everybody, I texted everybody I could. And then within those following weeks, messaged a lot of people I could to get recommendations. Now you can do it through LinkedIn, which is great. You can just message someone and ask them for a recommendation, but stuff like that, folks who were going to vouch for me with whatever came next, because, you know, at that time, I didn't know if freelance was going to happen, but I did know that I needed to kind of like collect these references and resources.

5:07Bre Simpson:So that was a huge one. I spent a lot of time on LinkedIn looking at what other people were doing that I really admired in two ways, like who's the competition and what's working for them. And I did kind of spin my wheels on that. I think a little too hard. It's a very vulnerable place to be to look at someone who's five years down the line And now you're, you know, 10 days in that kind of thing. But yeah, the LinkedIn was pretty critical. After that, it was all those building blocks of like, yes, I just left my job. But what do I want to do? Who do I want to do it for? And what makes it unique?

5:54Bre Simpson:Like, how am I doing it that makes me special to other people? and it's those first couple modules in fast like when you go through it it seems so simple enough but to kind of sit down and really like fine-tune those levers to find what works for you what resonates with clients takes a minute and then on top of that just all the small things setting up calendly setting up proposal documents setting up contracts like getting comfortable talking to customers or clients um the client research too very uncomfortable doing that but it really helped so those first 10 months it was messy it was really messy um because I felt like I didn't have I shouldn't say that like I you get to know who you are through doing those things and every step brings more clarity but yeah those first months was really like fine-tuning this picture of who I am as a designer, how I serve people, and what do I really bring to the table in comparison to other designers?

6:55Bre Simpson:Not that anything's better or worse, it's just who's going to fit this dynamic. Yeah, and so what were some of those things that you kind of like discovered about yourself or figured out about like your customer, your niche, and like that you kind of mapped out in those first 10 messy months? I, yeah, I'm very good at planning. I think coming from the biggest takeaway was I have come from this corporate background where I've worked inside these billion dollar companies. So what can I take? What can I extrapolate from that and help help startups, help new and emerging brands feel like they're getting not feel give them this kind of like roadmap ahead that doesn't feel so messy.

7:37Bre Simpson:So where I am maybe feeling a little bit messy in my business, I can look at somebody else's and say, like, OK, this is great. here's how we move forward and I think being able to speak to that plan ahead really started to resonate with people in a strong way and then the second side of that was just the visual representation of it because we can sit here and talk all day but that takes time that costs money so the the actual mechanics of those proposal documents the website the instagram like just getting all of that really crystal clear so people know who they're talking to before before the zoom screen even opens.

8:14Yeah. Super smart. Um, what was the source of those first few clients as you got started in those 10 months? And when did they, when did you, they start kind of trickling in? Yeah, it's, you know, I did come up against Upwork and a cup, you know, those were my first

8:34Bre Simpson:couple of clients. Like my first tech pack was 250 bucks for a men's boxer. Um, you know, it was fine um actually i did a lot of men's boxers at first um i think because man-made was coming out so strong in the market a lot of people thought they could follow suit so i did do about two or three menswear products to to jump in um linkedin now is probably the primary source of my clients um chat gpt actually has recommended me to some google search one or two not nothing Instagram and then, you know, Behance. I don't know if anyone uses that. Yeah. So a couple inquiries through there. But nothing that really stuck.

9:18Bre Simpson:Like usually it's, you know, they, once you approach them and say like, let's set up a time, it never really converted. But yeah, LinkedIn, ChatTNT are my top two. Okay. I love that. And so those clients started trickling in, you spend a lot of time kind of figuring out who you are, what you're doing, setting up a foundation of assets, making yourself present online, building out all those recommendations. It sounds like initially when you were reaching out to people in your network, you were primarily doing that to just get the recommendation that you could put on your LinkedIn. Is that correct?

9:52Yep, exactly.

9:54Bre Simpson:And I have like testimonials on my website and like, what can I, what clips can I like clip out, put on a cute graphic, throw on Instagram? You know what I Like, what can I do to just like keep the conversation going? Yeah. Okay, cool. And so you started out that very first project, and I love pointing this out, was$250 for a tech pack on Upwork. Yeah. Like, in the grand scheme of things, probably didn't really compare to what you were making at your day job. You know, I think, how did I price it out? I think what I did is I kind of estimated how many hours it would have taken me to do it at my desk job and then just divided my annual salary by an hourly rate and kind of went from there you know looking back absolutely like not not how I would do it now but it was great to kind of like you know especially with these smaller projects it's nice it's okay to be messy in that space yeah um I think that's really smart and one of the things I always talk about is like The pricing is like learning how to sew.

11:00Like at some point you just have to like start and those first things are messy. And maybe you have to like tear the fabric out and you just, you kind of don't know what thread or what stitches or what needle to use, et cetera. And it is like you learn by doing, even with all the strategy and support and templates and coaching and resources, you still really learn by doing. And so I love that you started with that and kind of got your feet wet. You have since graduated to maybe even larger than the number I have here, but projects upwards of$10 ,000. The biggest one I have on my list here is a$13 ,000 project.

11:32I don't know if you've had any ones larger than that since. But just to show the growth over that time, not in those 10 months necessarily, but in the 18 months since you've been freelancing, since you left your job.

11:43Bre Simpson:Oh, yeah, totally. So for comparison, yeah, that first tech pack,$250. bucks. Now, looking ahead now, you know, I think it was you who was talking about MLE, so your minimum level of engagement. So that starts at$2 ,500. And then I think the most long-ranging project I have right now is, it's in a couple phases, but yeah, it is in about the$20 ,000 range. And that's over like a 16 to 18-week period because we are covering quite a range of products. Sure. But yeah. Yeah. Like I said, it's predictable. It's stable. It's it's getting there. Yeah, that's amazing. Talk a little bit more about LinkedIn.

12:27Are you like what's your strategy there? Are you posting regularly and then brands are reaching out to you? Are you defining brands and then connecting in the DMs? I'd love for you to walk through like what's really working there for you.

12:40Bre Simpson:yeah absolutely I've been pretty quiet on LinkedIn at the moment um because I am kind of fully booked and I hate not being able to give like give people a spot in the calendar what I found that worked really well was was continuous posting the big thing I found once client work kept coming through the door is I didn't want to make work so at the beginning I was really spinning my wheels of like creating these carousels because that was big like last year it was big um what was it what was one of them like 10 ways to make your brand eco-friendly and then another one was like the five stages of product development and I was spending a lot of time just actually creating the posts um and then once that time you know was being replaced with paid work now the thing became like okay what can what's a snapshot of what I'm doing right now a big thing and I think it was you who said it is your clients really want to see themselves reflected in what you're currently doing.

13:36Bre Simpson:So I was, I have now a big part of what I asked my clients at the beginning is, are you comfortable with me sharing snapshots of things on Instagram and on LinkedIn? Because then it works twofold. I can kind of shout them out. And then people can kind of see like, oh, here's some mood boards. Here's some sketches. Here's a tech pack. And really engaging LinkedIn in what I'm currently working on. And I think that's been a big thing. And then of course, I used to do this thing of like uh every now like you know sharing your wins right wins on Wednesday so um I have my own graphics so I'll slot in like a good text message a good email that's just like really celebrating the work that's happening and then posting it on like Dan so yeah and and again like anytime there is a win to share like a product launch or I recently did a photo shoot just for myself like just these things it's like like I said like keeping that conversation going keeping that engine running I I found that like my big long posts weren't really performing and that's fine um you know the things that performed the best at the very beginning were hand sketches and they would get like a couple hundred likes and then I'd put so much work into doing some other sketches and then nothing so but you know um just because and since I pulled away from posting consistently.

14:57Bre Simpson:I'm still out there like commenting, reposting. I'm a big like celebrate thing on LinkedIn. So I feel like I've got like big cheerleader energy personally. So I really try to just project that outwards, like commenting, re-like or reposting, liking all that kind of stuff. So just like staying relevant, staying in, well, to be fair, staying in the algorithm. Yeah, yeah, yeah, totally. And whose stuff are you engaging with? Like, are your brands present on LinkedIn or is it other freelancers or what? Yeah, a lot of people from the FAST community, if I'm being honest, a lot of people within the Vancouver community.

15:35Bre Simpson:Vancouver has a really robust fashion scene. There's a couple of fashion schools here. So really engaging in that space. and then not so much brands, but the folks behind the brands. So when I'm looking for new folks to follow on LinkedIn, I mostly follow founders, entrepreneurs, and then obviously like folks within the industry. But I'm trying really hard not to make it a feedback chamber because I want to reach more people than my professional community. Obviously, I want to reach my professional community, but I do want to reach outwards. so it's more if someone's sharing something that their brand did i'll comment on them not necessarily the brand that makes sense so not the brand as a business but the person that's running the brand as a person yeah the person who's sharing it in you know that kind of thing if it's yeah uh there's a color developer for i think yeti and anytime she posts something like i love it i come i spend some time in color so i'm always celebrating that some print developers for for like anthropology like i'll always celebrate their work that kind of stuff yeah now are your clients if correct me if i'm wrong it sounded like at the beginning that your clients tend to be more small independent startups and you just mentioned anthropology and yeti so i'm just trying to understand um yeah yeah you know my question yeah no problem um so i work primarily with new and emerging brands.

17:07Bre Simpson:So almost exclusively startups. And I think the real attraction there is, like we were talking about before, I've come from that corporate background where I've been inside of billion dollar businesses. So I can really kind of take that framework and apply it to someone who may be feeling a little bit lost in a new industry. um and yeah I really I really like it I work in performance performance and activewear so I got a lot of really cool function first uh clients where we do have a specific niche we're going after we know the end use um and I love it yeah there's some really cool projects that have come my way but yeah um I have my two in a new year I'll be working with my two first established bands already and I'm very excited.

17:56Bre Simpson:And again, in that space, they are both function forward brands. So it's kind of nice to kind of step back from developing a business with somebody and jumping into a business that's already developed and being able to focus on design and production specifically. Yeah, just really focus on the product itself. And so to some extent, these folks, the person behind the brand, the founders of the brand are hanging out and engaging on LinkedIn you're finding and or enough that they're finding you on LinkedIn at some point. Yep, totally. Yeah. And so it sounds like everything's kind of inbound, like you're creating all this content, you're having all these conversations, you're engaging, playing with the algorithm.

18:34And then what happens? People land in your DMs or they reach out via another path?

18:41Bre Simpson:Yeah, mostly DMs. I get a lot through my website as well. Actually, I'd say primarily through my website now. A couple things will come in through LinkedIn now and I usually redirect them so they can like take a look set it up it goes when they submit all the context stuff it it auto it's automatically in the background like they can with county right like they book their own their own meetings it auto prompts them to fill out this intake form which gives me a bit of a profile on what they want to do anyways yeah um yes there was one other thing I was gonna share I have okay so cold calls um I have done some cold emailing and you know those first couple months, it didn't work at all, at all, at all.

19:24Bre Simpson:And then once I had an established presence, I did have a couple cold emails work almost immediately. In one case, I sent a guy a message and I was just like, hey, you popped up another Canadian brand. And I just wanted, I just wanted to say like, I love what you're doing in the Canadian activewear space. If you're ever looking for some support, like I'd love to chat. And he called me like 10 minutes later. Like literally picked up the phone and called you? Yes. Yeah. Like on the phone. So intimate. What century are we in? Yeah. And you know, we talked back and forth. We really went through what he was looking for, what I could do to help.

20:02Yeah.

20:02Bre Simpson:And they are very, they're in a transition in their business. So it's kind of been left on the shelf, but that conversation is still open. And then in another case, it was another brand that was looking. It was just kind of like a one-off where I saw on LinkedIn that they were looking for something and it kind of lined up with what I had done in the past. So I shot them an email and just said like, Hey, I know you're looking for X, Y, Z. This really lines up with blah, blah, blah, blah, blah. I'd love to chat if you have a minute. And within the week we were chatting, I'd sent them a proposal and I think my proposal was maybe too high for what they were looking for but you know what like in those in those circumstances it's not so much cold emailing where it is like you're ready to provide something of value totally we'll get back to the episode in 20 seconds but real quick a question if you have ever caught yourself thinking is this too much to charge or what do other freelancers quote for this you are not alone I created a freelance priceless just for fashion freelancers like you and it's absolutely free it outlines real world ranges for design tech packs pattern making and even 3d it is based on my 15 years of industry experience and over a thousand fast grads many of whom are now out earning their old full-time salaries download it now at soheadie.com slash price the link is in the show notes now back to the episode you mentioned that those first like once you had your presence more established you started getting replies more quickly to those emails was that so you were you reaching out over email or linkedin uh yes yeah reaching out through my person so I would find their email and reach out through my email it has like my email signature with okay you know my website like like you know what I mean like yeah yeah that like social proof of like yes this is who she says she is and she does xyz okay gotcha that's interesting that you noticed sounds like once you had that signature where they could then click through and see the validation of your online presence both on LinkedIn and your website sounds like that almost became a tipping point the website was a huge tipping point at first I like stuff was coming in enough without the website and I think as much as I don't think it's critical to have it just personally my experience has been that really was when momentum started to build are people like if I know chat deep tees recommend to you which is amazing um are do you know that people that come in from the website are they finding you on LinkedIn and then going to the website are they finding you on Google and then going to the website is finding you on chat.gp or maybe a little bit of the above all the above that's a good question yeah uh probably all the above like I I will say this I I really wanted to hit as many platforms as possible not so much to have a ton of stuff out there but just so that my name is across multiple platforms um i will say like my best friend is a copywriter whose background is in sas um and seo optimization so she's been this like secret agent in my back pocket and that was a big recommendation of is like as much as you can as many platforms as you can access sometimes that helps with backlinking um and your visibility on things like chat gpt and google so yeah the instagram pinterest linkedin my own personal website behance um i don't know if upwork does backlinking like if that works but i think there's an option you can make your profile publicly searchable like in the internet as a whole versus just searchable within upwork when someone's logged in or something like that yeah but i kind of think of it as this like you know you're if you're casting a net you're building this spider web to like bring people to you.

23:50Yeah. Um, and so did you really spend like those first 10 months, did you spend building a lot of that foundation out and slowly started getting some work? And then at that 10 month point, you're like, okay, now it's, I'm getting some consistency and some stability or has all of this. I mean, cause I think the reason I'm asking is because I think someone who was listening, who wants to get started, um, or maybe like has a couple of clients wants to grow all of those things is a lot of work right and I think it can feel like really overwhelming to be tasked with like okay well now go create presents on all these places um and so was that something slowly you've kind of done and added over the last or the first year ish maybe yeah those first couple months so trying to think it was a bit of a slower

24:44Bre Simpson:build because I did have I did have that time like um you know thankfully I had a severance Canada has a really robust social service network um and it was also summertime and it was the first summer my husband and I were married um so we did take some time off like the whole month of August I took off to go camping um so it wasn't a full grind the biggest thing I found was my communication with clients so how am I presenting myself um I sent you know I had this big proposal deck and I showed it to a couple of friends and they were like it's just a wall of text it's so much text like you have to break it down you have to break it up um so that was some great feedback like it doesn't matter how many pages it is like just buffer it make it pretty make it digestible and that was a huge a huge piece of advice like because in my mind I'm coming from this corporate place where I'm like okay let's get it set up here's how it's going to work here's how much it's going to cost here's a calendar and people are like invite them in like invite them break it down each page should be its own thing and so that was that was great and you know I didn't have money for photo shoots so I my my girlfriend works at an art studio so she let me come to her art studio and another friend was a model and we took all the photos with my camera my phone my old old iphone um using like a broken iphone tripod so the photos that are currently on my website were all taken in that like that first couple months I've since now recently done a shoot where I can kind of update some of that yeah um but yeah like it was it's it was scrappy very scrappy I built my website myself so yeah you know some things are a little rustic the edges are a little bit sharp yeah um but yeah I mean I've got it and I did take a lot of it looks good oh go ahead sorry yeah no go ahead you did take a lot of what I I took a lot of time like it's probably like the fifth or sixth website that I built because I kept building it and not liking it and building it and not liking it.

26:55Bre Simpson:I wouldn't publish it. I wouldn't publish it. And then one of the manufacturers that I partner with, they wanted to promote me on their LinkedIn, on their site. So that was a real ticking time clock, right? Like, okay, I've got six days to have a presence because once that goes up, I want, again, I want something that's going to feed back to what I do. So that was to be honest, that was like a major tipping point in terms of like, okay, you have to do this now. Yeah. There's nothing like a good deadline imposed by someone else. Honestly, it's like, I wish it would have happened sooner. I was just talking to someone the other day, this is on a little off topic, but kind of on topic about pitching.

27:38And she was like, but wait, I have to like finish my portfolio first. Cause what if they ask to see something? I'm like, then you scramble and you get it done. Uh, because otherwise you're going to spend a million and a a half years on it and it's a very comfort zone activity and you're going to over tweak it versus like get yourself out there and then you scramble and you make it happen um let someone else make the deadline for you um this is amazing and so phenomenal and I know that it has not come without a tremendous amount of hard work which I can already clearly tell you've put in but also like challenge and failure and personal struggle and before we hit record you shared some stuff with me and I, um, I'd like you to open up to some extent about some of the personal stuff you're going through in that initial journey of starting your finance business, um, first.

28:25And then I have some other questions after that. We'll start there though. Yeah, totally.

28:29Bre Simpson:Yeah. So, you know, I'll start this off by saying everyone's okay. But yeah, that first couple of months, my husband and I were married to like 23 into 24 was pretty rough. Like my mother was diagnosed with terminal cancer. She's fine now. My mother-in-law also went through breast cancer. The business, my husband had equity in. The investors decided to sell the business. And then unfortunately, my husband was hit by a car when he was riding his motorcycle. He's good. And then three weeks later, I was laid off. And then three days later, my husband was laid off. So within nine months, it really, like our whole life just kind of imploded.

29:07Bre Simpson:And it was tough. It was real tough. But, But, you know, now that we had this time to heal and rebuild, you know, it's we are probably on a course that more aligns with the life we want to live than maybe we were before. But it did take a while to kind of like breathe that loss. Like I loved being a corporate designer. I loved I loved it. I was I was so proud. So and I still am. That doesn't take that away. I was really proud to be at places like Lulu and Aritzia and Kit Nase and see those things. So, yeah, having to, and I did pursue, like, I didn't come out of that. Actually, I did. So I did tell my husband, I bless his heart.

29:53Bre Simpson:I did say, like, I'm going to make this work freelance because we're never going to be in this position again. Like, I never want us to worry like this again. um but I did pursue a couple other corporate jobs in that in that time frame um and a couple that you know I absolutely would have said yes to um but yeah it's it was a lot of hard work it and again with freelancing it did offer a lot of opportunity to be there with my husband go home to my family um take take a month off and just kind of like heal and reconnect after after such a hard year so yeah it's it's been a really rough journey but I'm I'm so happy for where we've ended up now yeah had you considered freelancing at certain points along the way constantly okay and what I mean it was a big reason like yeah what stopped you is a big reason why yeah is I mean the whole reason I started listening to this podcast was because of that and I've done it kind of on and off through the year for small projects, really depending on how litigious who I was working for was at the time.