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This is a show for burnt-out fashion designers (and TDs, PDs, patternmakers and beyond) who want more flexibility while still doing work they love. As a freelance fashion designer, you can build your fashion career on your own terms. Freelancing in fashion is the only way to get freedom in your day (instead of being tied to a desk). Whether you want to earn extra money on the side, fund your fashion brand, or replace your salary, the FDGP podcast will help you get there. Listen in for actionable tips and strategies to kickstart or grow your career as a freelance fashion designer, build your confidence, and create the life you want. Hosted by $100k+ fashion freelancer Sew Heidi, the show features interviews and strategy sessions with successful freelance fashion designers from around the world who've ditched toxic fashion jobs and taken control of their own destinies. This is the only place to get REAL insights from REAL freelancers who have built REAL careers on their own terms. (Formerly the Successful Fashion Freelancer podcast.)
Heidi [00:00:00]:
If you have ever had panic attacks from your fashion industry job, you are not alone. Courtney Osborne is a fashion designer whose career had gotten so volatile, she considered becoming a dental hygienist and leaving the fashion industry altogether. Because of the toxic work environment and these panic attacks she was getting from work, she was weighing her options between that or freelancing. She is here today to tell her story. So, yes, spoiler alert, she chose freelancing. And spoiler alert, she is very happy about her decision. But like everything in fashion or life, it hasn't been perfect or easy. Our conversation today is so real and so raw, and she is fully honest and transparent about where she's been and where she's at in her fashion career and life.
Heidi [00:00:43]:
Courtney is still in her 1st year of freelancing, which, like I say to everyone, in year 1, you optimize for your learning, and in year 2, you optimize for earning. She is soaking it all in, making sure she does celebrate her wins, even the small ones, and learning every step of the way. If you feel like the fashion industry has beat you up or you
Courtney Osborn [00:01:07]:
first, can
Heidi [00:01:11]:
first, can we set the stage with your thoughts about coming on the show to begin with? Can I put you on the spot and talk about that? Yeah. K.
Courtney Osborn [00:01:22]:
I was really nervous to come on, just because I know you know, but I do have impostor syndrome, like so many of us. And I was just like, you know, what do I have to offer? What if I sound stupid? You know, what do I even really have to share? And I know all those things are not real, and part of it was just me feeling better about where I was at in my freelance journey too, because I am really new to this. I haven't even hit my 1 year mark yet. Yeah. So, yeah.
Heidi [00:01:56]:
I think it's really important to recognize because, you know, your success is great, but it is arguably still modest in comparison to some other people's stories that I have shared in the podcast. Right? Yeah. And I think it's important to show a variety of stories and stages. Right? Like, not everybody is replacing their full time salary in 3 or 6 months. Like that is arguably very unrealistic. And so I think it's important to, like, talk about the stages. I mean, I know you said in April, you didn't make any money. Like that's fine, but I think that's important to talk about.
Heidi [00:02:41]:
And that that is the realities of early days early days of freelancing. And, you know, there's so many variables to throw into this. Right? But I I think that when you told me you were hesitant and you one thing you specifically said, you were like, I feel unworthy. And I was like, what? Oh, that really I mean, it kind of crushed me a little bit. I was like, no, you're more than worthy. And I, everybody has a story to share and I think it's important that we share all of them. And, thank you for coming on and despite, like, those emotions.
Courtney Osborn [00:03:21]:
I it's funny because last week when we talked, I was, like, feeling a very certain type of way, and that's how we ended up doing the alternative version of the the interview. Yeah. Plus just, you know, my big ideas. But this morning I woke up and I was just like, you know what? I'm just gonna be super honest, and like, I'm not gonna be afraid that, like, people are gonna hear this and think certain things about me, because my my area of genius to kind of steal your your phrase
Heidi [00:03:51]:
It's not my thing. It's, yeah.
Courtney Osborn [00:03:53]:
It's just when I'm being really, really honest. Like, that's when I feel my best. That's when I feel like I'm helping people. That's when I feel like I'm being my true self, and so and if you don't like how I share how you've interacted with me, like, maybe you should think how you in about how you interact with people.
Heidi [00:04:13]:
Yeah. And And I
Courtney Osborn [00:04:14]:
don't mean you. I mean, other people that I may or may not talk about at some point on this podcast.
Heidi [00:04:18]:
Yeah. Yeah. Yeah. Totally. Totally. Okay. Well, you know I'm all about real and raw. And for because I'm just relooking the podcast schedule.
Heidi [00:04:30]:
This. Whoops. Hold on. This is going to air before that airs. So people listening to this, Courtney threw an idea at me, and it will be coming out later on the podcast. And she said, Heidi, I would really love to interview you. And so we did that last week. So that's what she's referencing, but it won't be live yet when people are hearing this, but it will be coming soon.
Heidi [00:04:59]:
So
Courtney Osborn [00:05:00]:
It's gonna be really good and then everyone will enjoy it.
Heidi [00:05:03]:
Yeah. And and so I wanted to set that context for people, but I also wanted to, say talk about real and raw.
Courtney Osborn [00:05:12]:
Oh. It gets real.
Heidi [00:05:14]:
We got real, like, therapy level deep, which was really fun. And I love those kinds of conversations. So I'm excited to turn the mic on you now this week and do that from your side. So, give everybody yeah. Give me, like, what's your backstory? How did you end up here as a freelancer?
Courtney Osborn [00:05:36]:
Do you want the short version or the long version?
Heidi [00:05:38]:
Let's do the short, and then I'll, like, ask you to maybe expand on certain parts of it.
Courtney Osborn [00:05:43]:
Okay. So I went to school for fashion design. I am born and raised in Cincinnati, Ohio, that's where I went to school. I worked in the corporate realm for about 12 years and that was in a lot of different areas, a lot of different, brands and categories and age ranges, mainly at 2 large companies, and then, I had a string of toxic situations and bad relationships and bad managers, and, put me in a really bad mental place. And so, I was at the point where I had moved across country for a new job, hoping for greener grass, and it started off really good, and immediately after like about a year went downhill, and I was just like, about to give up on fashion. I felt like, okay, this has now happened to me twice, is this the reality of this business? I can't keep going on like this because I am in a bad mental place, and, like, I am not enjoying life anymore. And I'm not saying that I was not suicidal, although my doctor asked me that regularly. Mhmm.
Courtney Osborn [00:06:59]:
And I, you know, I had to go on antidepressants, and be in therapy, and, like, all that stuff. And and my, boyfriend at the time turned fiance, soon to be husband, was just like, yeah. We can't. You can't keep living like this. This is not okay. And so I was, like, I literally took a mental health leave, and I was just trying to become a human again. And I started thinking about, like, okay, do I completely exit fashion? Do I go back to school and get a different a whole different career? I know I'm capable of that, but do I really want that? What does that look like? What is the school cost? You know, all those things. I mean I was literally like, okay, should I just become like a dental hygienist, like, you know, there's it's very black and white in that situation, and then I found you.
Courtney Osborn [00:07:55]:
And, honestly, I I think I've this to you probably, like, tired of hearing it, but it just felt like fate. I was back at that toxic job after my mental health leave, kind of trying to figure things out to see if I could stay, and, because I had been looking into freelancing and fashion as an option, and just kind of feeling like, okay, can I do that? How hard is that going to be? How much struggle is it going to be? Is it possible? All the things. And you were having a webinar, and I signed up for it. I was still working, so it was during the day, and I was gonna try and, like, multitask and listen to it while I was still working, and I got fired. Oh, I can't believe I said that.
Heidi [00:08:50]:
Like, that day?
Courtney Osborn [00:08:52]:
Yeah. Oh,
Heidi [00:08:53]:
no. I didn't realize it was that actual day.
Courtney Osborn [00:08:56]:
That actual day. Yeah. Holy cow. Okay. Yeah. So and it was not because I was listening to your your thing, obviously. Okay. No.
Courtney Osborn [00:09:06]:
I mean, like, you know, people listen to podcast or, you know, audio books or whatever music while they're working. I was just listening to a webinar. But yeah. They had no idea. That that ball was already in motion. I, of course, have shame about being fired, I, you know, it's scary to share that, it feels very bad. Yeah. And I am not a person who I'm just, I'm like, this sounds really stupid, I guess, in my head, but, like, I'm not the kind of person that gets fired.
Courtney Osborn [00:09:42]:
You know? Like, I try my damndest. Yeah. No. I know
Heidi [00:09:46]:
your own ethic. Yeah.
Courtney Osborn [00:09:49]:
You know, I do my best to understand on situations and people, and get along with everyone, and, like, you know, all the things. So, the reality was is I had gone to my VP and told her that I felt like my manager was mistreating me, and at at the the initial conversation was, sorry. Do you wanna hear this whole story?
Heidi [00:10:10]:
Yeah. Yeah. I do. Keep talking. I'm, like, on the edge of my seat. And being out of listeners would be like, Heidi, you can't don't shut this down.
Courtney Osborn [00:10:21]:
Okay. So I had been telling my VP that I was having a really hard time communicating with my manager, you know, that I was trying, but I I just constantly felt bad whenever we were having interactions, and I was, like, you know, I don't know how to make this better anymore. Like, I feel like I'm doing everything in my power to try and make this better, and I there's nothing I can do at this point anymore to make it better. And she was still just, like, well, you're not trying hard enough.
Heidi [00:10:46]:
Mhmm.
Courtney Osborn [00:10:47]:
You know, and, you know, also, me being in a bad mental space, I'm sure there were things that I were not I was not doing right. I I can attest to that, like, you know, nobody does their best work when they're miserable and depressed, and like literally fighting anxiety every minute of every day. Having panic attacks in their car and crying during the workday. So anyways, I was having a conversation with my manager that I did not have a good relationship with that point anymore, which by the way, when I first started working there, we had a great relationship. Like, we had lunch together every single day. We like, we would share food, like, she would bring half, I'd bring half, we'd make salads together. Like, we were very, very friendly. So the switch was very hard for me to understand.
Courtney Osborn [00:11:41]:
So we were having a conversation, this was after my mental health leave, and she was, like, kind of berating me for doing a bad job on something, and she literally said to me, like, you threatened to steal my job, like, why can't you even do this? And I was just like, what? Like, I didn't threaten to steal your job. Like, what? What? And I was like, I never said that. And I'm thinking to myself, like, who in their right mind tells their manager that they're going to steal their job? Like nobody, especially not me. And she was just like, I don't want to talk about it. I was just like, okay. So this is obviously going nowhere. So back to my VP, I wrote her a very carefully worded email that just basically said, like, you know, I've been telling you that she's not been treating me well, and we're having a really hard time. And, she's now said to my face that I was trying to steal her job.
Courtney Osborn [00:12:46]:
So she obviously has this, this, you know, thought process around me. I don't see this getting better. I know that there's a business need. I know that there's work that needs to be done, I have no problem with that, I can continue doing this work, but I don't feel like I can any longer do that with her as my direct manager, because it's hurting my mental health, it's hurting my financial, and, you know, prospects because because she gave me a bad performance review, raise, I didn't get my bonus that year. Oh. And she's threatening my my continued employment here, because she's telling, constantly telling, you know, me, you, and everyone else that I'm not doing my job. And I was fired 2 days later.
Heidi [00:13:28]:
Oh my gosh. Yeah. That feels so hard that, like, you were trying to be productive,
Courtney Osborn [00:13:42]:
Mhmm. Mhmm.
Heidi [00:13:47]:
Like, you want to be able to speak up, but Oh, it's like, oh, now my job's at risk.
Courtney Osborn [00:13:53]:
So crazy. And that's essentially, it's very similar to what happened at the previous job, is that, I'd worked there for 8 years, and I had a great track record of high performance, and doing all kinds of extracurriculars, and, like, really doing my best to be, you know, a good advocate for the company.
Heidi [00:14:14]:
Mhmm.
Courtney Osborn [00:14:15]:
And then I had got put under a new manager, and within 6 weeks, I was having that was the first time I had my first panic attack. Oh, no. Because she was so emotionally abusive. And because I'm a high performer, and I'm a perfectionist, and I take things very seriously, having someone constantly tell you that you're not good enough, or that, like, essentially making you feel stupid and gaslighting you, Like, it it altered your whole world view. You're like Yeah. What am I even doing here? So I, sorry. I had gone to HR after that situation, that's a longer story. We can maybe get into that if you want to, but, I went to HR after that situation and I was just like, she's being emotionally manipulative and, like, essentially terrorizing me, bullying me, and they did nothing.
Courtney Osborn [00:15:13]:
Like, nothing. It's horrible.
Heidi [00:15:16]:
You've been there for 8 years too. I mean Yeah. Okay. So very toxic, very abusive environment. I know people listening are, like, oh, yeah. That is my story too. So I thank you for sharing that. And I know you and I talked before about you, you had a visceral reaction when you were like, I was fired.
Heidi [00:15:38]:
You're like, I can't believe I said it. I know you've had reservations about sort of saying that out loud. Yeah. So so thank you for sharing that because I I it was a very honest, vulnerable moment for you. And I know a lot of people are gonna be able to resonate with this story. So thank you for that. So it's the day you're watching my my webinar, my live training, and you got fired. And so what were what was your thought then about freelancing and, like, your life, and fashion?
Courtney Osborn [00:16:14]:
Honestly, so that day, I was celebrating. I was so relieved for that situation to be over, I literally went out and bottle a champagne bought a bottle of champagne and, like, popped it that night and celebrated. Wow. Yeah. I was like, okay. Like, this is now the end of that chapter. I can move on from this. I don't I it was kind of nice that I didn't have to make that decision anymore, because I was constantly talking to Tyler, who is my fiance.
Courtney Osborn [00:16:46]:
Sorry. I, like, I always struggle with what to call him. He's been boyfriend for 9 years, and now he's fiance and future husband. Anyways, so constantly talking to him about, like, okay, like, what's the next move? When am I gonna quit? Like, am I gonna quit? Am I gonna try and stick this out? What am I gonna do? How am I gonna make money? And so that was no longer in my hands, it was just like it was it was decided for me, and that was just such a relief. And it was just like, okay, now now I figure out what's next. Okay. And then taking your your webinar, which is great for anyone listening who hasn't taken it yet, highly recommend. I was just like, okay, this is a road map, I can do this.
Courtney Osborn [00:17:28]:
This is a how to, I'm good at this. Follow the steps, do the things, get it done.
Heidi [00:17:33]:
Yeah. Yeah.
Courtney Osborn [00:17:35]:
Do you actually have I think I I don't know if it comes as part of the webinar or what, but the get shit done package?
Heidi [00:17:43]:
Oh, yeah. People can it's an add on. They can add to their order if they want. Yeah.
Courtney Osborn [00:17:47]:
So I, yeah, I added that on. We can do that. Yeah. And then I kind of fell in love with you just as a human being, because I was like, this is my vibe, get shit done. Like I literally had, so I, you know how the 8 year career, I was at Kohl's, I'll just say it, I was at Kohl's, I did a lot of volunteering there, and doing, like, big corporate events. And so I was helping with one of these big corporate events, and I was in the bathroom, and it, like, super high up VP, walked into the bathroom and looked at me. She's like, you're the kind of get shit done person, aren't you? And I was like, yes, I am. Thank you.
Courtney Osborn [00:18:31]:
Anyways, that was a little side note.
Heidi [00:18:33]:
Yeah. Okay. So you were like, alright, I can do this. I'm gonna jump into freelancing. What did those first few months look like? You had lost your job. You felt relief
Courtney Osborn [00:18:48]:
Yeah.
Heidi [00:18:48]:
That they made the choice for you, which is a really interesting perspective. Mhmm. And, like, what what's the cold hard reality of those first few months?
Courtney Osborn [00:19:00]:
New Jersey has really, really great unemployment, so that was, that put me in a really good spot, and I know that doesn't it's not how it is for everyone.
Heidi [00:19:10]:
Mhmm.
Courtney Osborn [00:19:11]:
So I felt really blessed that I was I had moved to New Jersey, and I was able to get that level of unemployment help, because without that, I would not be in the position that I am in today. So there's a lot of my life that I just feel like I know that I've been lucky and blessed, you know. There's definitely a section of hard work that is involved. I, you know, I don't sit back and wait for things to happen to me, but I acknowledge when I've been lucky. And in that in that situation, I was lucky.
Heidi [00:19:41]:
Mhmm.
Courtney Osborn [00:19:43]:
So having that as a safety net, I started doing research, both into freelancing and also into other drops, just to see, you know, what else was possible in my new location. The other thing about me, that is different, I guess, than most people is that I have a sleeping disorder that's called, oh my god, I just blanked. I hate when I do this. You ever know when you're introducing people, and you're like, this is this person, and then like when you when you just have that fear, and then it suddenly zaps the information from your mind?
Heidi [00:20:19]:
Yeah.
Courtney Osborn [00:20:20]:
Hypersomnia. Okay. So hypersomnia is like a mild form of narcolepsy, and my brain tells my body that it's time to go to sleep in inappropriate situations. And so I do take medicine for it, but I choose to not have long commutes, because I could fall asleep while driving.
Heidi [00:20:42]:
Mhmm.
Courtney Osborn [00:20:43]:
So me commuting to somewhere 45 minutes, 2 hours away, not realistic for me, because I know that I would put myself in a bad situation. And that was the other reason why I felt like freelancing was going to be my reality, was because that I can work from home, I can work for a lot of different people, I don't have to worry about commuting, and I can still do what I love. And so that was the other thing is that I just kept thinking like, this is what I want, so I'm going to make it happen. And that's just kind of been like every time I I I have a moment of weakness or being afraid or like freak out, I just keep saying to myself, like, no. This is what, this is the life that you want, so make it happen.
Heidi [00:21:37]:
And that's really interesting to me. I mean, I think those moments that freak out are super normal. Like, when do you tend to have them? Like, I wake up in the middle of the night, and I'm like, what am I doing?
Courtney Osborn [00:21:54]:
Sometimes before bed. I feel like they're they're actually the worst in the morning, which really sucks because that's how you start your day. Yeah. And I have been battling that for a little while, and I do still have, like, the leftover anxiety from past situations. And so I battle that too. I am in therapy. So I also have her in the back of my head talking to me, you know, similar to how I have you now. So, like, I've got these 2 little, like, I got my support system in the back of my brain just going, it's gonna be okay.
Courtney Osborn [00:22:29]:
Yeah.
Heidi [00:22:31]:
And like, what are the sorts of things that you're freaking out about?
Courtney Osborn [00:22:37]:
It's funny. I was actually thinking about this before. I don't have as much fear talking to people as I do when I'm presenting work. So my my biggest fear or, like, issues, I think pop up when I have to deliver. So when I get a project, like, everything in the getting of the project to me is easy. Wow. Yeah. And and and doing the work itself can be easy for me.
Courtney Osborn [00:23:13]:
But the fear of rejection or some like, how somebody might perceive me or, you know, just feeling good enough, or thinking that they're gonna think that the quality of my work is good enough. Yeah. And I think a lot of that has to do with my more recent situations of having people tell me that I wasn't good enough.
Heidi [00:23:34]:
Right. Totally.
Courtney Osborn [00:23:37]:
Because yeah. And and a lot of those situations, I was, like, you know, doing the work, and and I had been doing the work. So I knew that I was capable of doing the work, and then I was told that I had
Heidi [00:23:48]:
failed. Yeah.
Courtney Osborn [00:23:49]:
Which I feel like saying this out loud is very therapeutic for me right now. So yeah. Every time I get a new client, or start a new project, once once there needs to be a deliverable, that is when the freak out starts. Okay.
Heidi [00:24:13]:
And so I know you said you one of your coping mechanisms is, I chose this life, this is what I want. Is that's, like, sort of your mantra going into those presentations? Or, like, how
Courtney Osborn [00:24:29]:
that's actually I use that the most when it's, like, motivating myself to get to get shit
Heidi [00:24:34]:
done. Okay. Okay.
Courtney Osborn [00:24:38]:
So when I'm in those scenarios, when I'm I'm experiencing the freak out of like, the work, Sometimes I talk myself through it. I've done this a 1000000 times before, I know what I'm doing, all I can do is do my best, and if something goes wrong, I will fix it. I will learn from it.
Heidi [00:25:03]:
Mhmm.
Courtney Osborn [00:25:04]:
If this is a subjective situation, and they're unhappy, they need to tell me, and then I'll fix it. So it's kind of like, you know, if you're worried about the what if in a negative way, you have to flip it to say, like, okay, if that happens, what am I gonna do about it?
Heidi [00:25:25]:
Mhmm.
Courtney Osborn [00:25:27]:
And then you also kind of realize, like, through that thought process, there's maybe some what ifs that are just not realistic. Like no one's gonna flip the table and tell you you're stupid. And if they do, that is what client you want.
Heidi [00:25:39]:
Yeah. These, like, extreme worst case scenarios
Courtney Osborn [00:25:43]:
Yeah.
Heidi [00:25:43]:
That yeah. I know people that have that thought process. Like, everything in life is, like, extreme worst case, and you're kinda like, but that's, like, it doesn't really ever happen. But these other ones, like, what if they're not happy, and what if they don't like my designs or something like that? Like, that can happen for
Courtney Osborn [00:26:00]:
sure. Yeah. And you know what the funny thing is, is like, it's not happened to me yet.
Heidi [00:26:04]:
I was just gonna ask. It's been good. Your clients have been happy.
Courtney Osborn [00:26:09]:
I mean, it's not like I've had this whole, like, laundry list of clients, I've only really been doing this for like, truly, let's say 8 months. Okay. So, but still, you know, it's not happened yet.
Heidi [00:26:24]:
Okay. That's exciting. Is that relieving some of the truth?
Courtney Osborn [00:26:28]:
That's not true. I did tell you. I had one client that just sent me a really nasty email after I did a project. And it was already a situation where, like, I was getting weird vibes from them, like, the whole time. It took, like, almost 4 months for us to go from initial conversation to actual project.
Heidi [00:26:55]:
K.
Courtney Osborn [00:26:57]:
And there was a lot of talk about cost and stuff. And so I felt going into the project, they were very concerned about how much time I was gonna spend on it, and that this was, like, just truly a test to see like how much work I could get done in a certain amount of time. Because that was the vibe I was getting. Granted, in retrospect, my bad for making assumptions about what they wanted. Mhmm. But again, that's part of, like, the vibe, you know? Like, when you're when you're talking to someone new and you're getting to know each other, that was the vibe I got from them. And so I finished the project. I was like, okay, it took me 5 hours, like, here's some screen caps of, like, where I was at 1 hour in, because she kind of wanted to know that.
Courtney Osborn [00:27:48]:
You know, I have some questions, here they are. Let me know where you guys want to go from here. And she was, like, I can't believe you spent 5 hours on this, like, you didn't check-in with me, like, what were you thinking? Like, this is not how people work, and I was just, like, I I don't I can't even remember exactly how I felt. Obviously terrible. And I sat on it for a minute, and then I just like, I was also extremely embarrassed, because like again, I hold a lot of shame when I feel like I'm not doing the right thing or being good or whatever, meeting my levels of perfectionism. And so I just emailed her back, and I just basically was, like, you know, it's fine. It's clear that, like, we're just not a good fit, you know, not everyone always is, and so that's fine. You can pay me for the the 1 hour test rate because that was what she was offering me after her nasty gram, and we'll go separate ways, And I haven't spoken to them since.
Heidi [00:29:01]:
I mean, I gotta be honest. Her wanting to see, like, screen caps of your time and where you're at after 1 hour, like, that type of excessive tracking is a huge red flag in the first place to me.
Courtney Osborn [00:29:15]:
Yeah. And I think it's
Heidi [00:29:16]:
And that was a learning opportunity for you.
Courtney Osborn [00:29:18]:
Oh, yeah.
Heidi [00:29:19]:
Yeah. And
Courtney Osborn [00:29:21]:
and so I felt bad about it for, like, a week. You know, I really internalized that, like, negativity.
Heidi [00:29:26]:
Yeah.
Courtney Osborn [00:29:26]:
But, you know, I talked to you a little bit about it, I talked to my freelance friends a little bit about it, I shared, like, the whole situation with one of my good friends, and she was just, like, just move on. Like, this is just a bad, like, one bad situation or example, and like like you said, this is obviously not a client that you would want, so just move on from it. And I it took me a little while, but I did.
Heidi [00:29:55]:
Yeah. And you've had other clients that have been great, and have been very happy with your work.
Courtney Osborn [00:30:02]:
Mhmm. Yeah. So happy that my my very first major client, that was not somebody that I'd known from a previous relationship, referred me to, like, 5 different people.
Heidi [00:30:13]:
What? Yeah. You didn't tell me this.
Courtney Osborn [00:30:15]:
Well, none of it's turned into, like, actual paid work, but, like, the fact that she was willing to say, like, you know, here's this person.
Heidi [00:30:24]:
Yeah. That's amazing. That's a huge compliment. Mhmm. Where did you get that first client? Or not that first client, but that one that major client that was not from someone you had already known?
Courtney Osborn [00:30:35]:
From the Fast community.
Heidi [00:30:37]:
Oh, yeah. Okay. Mhmm. Yeah. Awesome. Awesome. I know that I I know from firsthand experience that, like, one of those negative interactions can still just overshadow those 5, 10, 20, 50, a 100 good ones. Right? Like, one negative thing from someone can throw away all the good stuff.
Heidi [00:31:07]:
Mhmm. Like, have you been able to let it let it go after you said it sat with you for, like, a week? Yeah.
Courtney Osborn [00:31:17]:
I I think because it was a, the project was for art, which is not my niche, not my strong suit. It's something that I can do, but it's definitely not my expertise, and it's not the thing that I like offer very often. So, also this client, by the way, when I first started talking to them, they wanted me to do artwork placements, Like that was what they were initially hiring me for, and then it shifted into doing artwork. So very different things, But anyways, so I think because I don't do artwork very often for clients, it it doesn't come up in my brain, like I don't think about it. And I also choose to just move on from it. Yeah. You know? It's it's not a good use of my energy to be negative, and to to harp on those things, and that is the kind of space I'm trying to stay in, in this whole this whole situation. Like since I started freelancing, I have tried to make it a priority to just constantly stay positive.
Courtney Osborn [00:32:33]:
Like, I don't know if it's toxic positivity, but it's just like, I don't think it is, because toxic positivity is like saying everything is okay when it's not. I am not letting myself let the negative thoughts in. So like, instead of, like, catastrophizing, I cannot say this word lately. Catastrophizing, that's not it.
Heidi [00:32:55]:
Catastrophizing, I think.
Courtney Osborn [00:32:57]:
Yeah. This is I feel wrong. Catastrophizing.
Heidi [00:33:00]:
Yeah. I'm not sure that's a word I use much, but I think that's it. Catastrophizing.
Courtney Osborn [00:33:04]:
Yeah. Yeah. So that. Instead of doing that, I am just, like, if I believe in myself in doing this, and follow the steps and do the work, it's gonna be okay.
Heidi [00:33:20]:
Mhmm.
Courtney Osborn [00:33:20]:
Like, there might be bad months like April when I didn't have any paid work. Mhmm. But but then May, I made over $2,500. So, like, you know, there's gonna be highs and lows, but just keep doing the work, and it's going to be okay. Because being negative it's just, it's a waste of energy.
Heidi [00:33:47]:
I love you. I mean, I know you are big on personal development, and you are working with a therapist. And you took that mental health leave from work, which I think is amazing, and I think more people should I don't know if a company has to, like, offer those benefits or if you, like, made a special arrangement or what have you. But I think it's really important and it's really, really clear, like all the mental work you've done for yourself and like how it comes across in your attitude and the way you treat yourself and talk to yourself. And nobody's perfect, right? But, it's really clear how you are so supportive of yourself and, like, giving yourself grace. I love that.
Courtney Osborn [00:34:30]:
Yeah. Giving myself grace, that has been something that I've had to learn a lot over the past year. Like, but even before, like, when I started working with my therapist that I have now, who is great, highly recommend finding a good therapist. That was, like, I think, one of the first things that I had to start learning because of my perfectionism and my fear of of being perceived as bad. I never let myself have that grace, and I was constantly exhausted, because I was constantly in burnout, because I was, like, if I'm not doing all the things, if I'm not working my hardest, then I'm not good enough. And so I was never truly resting. Even when I was like, curled up in a ball on the couch because I physically could not keep going, I was sitting there berating myself for being on the couch. That was hard.
Heidi [00:35:35]:
Yeah. I know your work ethic, and I know your drive, and I know you're, like, a type a go getter overachiever, which is very similar to my personality. And I've I've had that same emotion where I'm, like, resting, and I'm, like, the amount of overwhelm I feel in my body of, like, I should be up. I should be doing this. I should be doing that. And, like, gosh, I can't be resting. And maybe not always the best attitude to have for ourselves. We do need to rest.
Courtney Osborn [00:36:06]:
Yeah. Yeah. Because, like, that that mental marathon that you're running, you're not resting then. Your body's still in a state of, like, high anxiety, like, those whatever those chemicals are in your body are still, like, rushing. And so, like, you might be lying down, but you're not resting.
Heidi [00:36:24]:
Yeah. I'd love for you to talk about, like okay. So you were you were working. It was very toxic in 2 jobs in a row. And you were like thinking, okay, I can either leave the industry, go be a dental hygienist, or I can stay in the industry as a freelancer. You chose the latter to freelance. I know it's not been quite a year, but I'd love for you to talk about the good goods and the bad bads of like this choice, that you've made and this life that you've chosen for yourself, what does that look like over the last 8 months? What has been awesome and what has been like still really hard? Or maybe a new really hard thing?
Courtney Osborn [00:37:16]:
I think the the easiest answer for, like, the super, super high highs is just being, like, having the freedom to do what I need when I need to do it. Mhmm. And that goes from giving myself that grace to sit on the couch and to actually rest and to become a human being again.
Heidi [00:37:33]:
Mhmm.
Courtney Osborn [00:37:34]:
And being able to go home to Cincinnati and spend time with my family. And, like, my mom had major surgery in December. Had I still been in one of those corporate jobs, I never would have been able to go home and spend that time with her. I stayed home for, like, 15 days, and I was able to be there for her and stay the night in the hospital and take care of her. And, like, my whole family is very, very close. So it's not like I was the only one, and I wasn't the only one able to, but being able to participate in that and be there and not have the fear and the worry that I would have had had I been having to work that 9 to 5 and not being able to go home. And the freedom of not having to worry about what people thought about me taking that time off, or, the anxiety that would have come with returning to work after that time off, and also being able to work during that time. Granted, I was still learning a lot, about how to go about freelancing, and I was just spending a lot of time, I think, just like doing the courses and networking and talking to people.
Courtney Osborn [00:38:50]:
And so there wasn't a lot of paid work during that time frame, but it was still I was still working on the business, you know, maybe not in the business, but on the business.
Heidi [00:39:02]:
Mhmm.
Courtney Osborn [00:39:04]:
So that that's definitely a huge high, and I think that's something that I feel grateful for every single day. Is that I get to choose what I'm doing and when I'm doing it. And getting to plan to go home, and visit my family, and and being able to stay there for as long as I want, and and having the flexibility to do that on any given day. Like, it doesn't have to be flying out on a Thursday night, and, you know, taking a long weekend. It doesn't have to be, you know, just this the craziness of of living by someone else's rules.
Heidi [00:39:41]:
Mhmm. Yeah. Because I know in May you went home for like 2 weeks for some of your wedding stuff.
Courtney Osborn [00:39:48]:
Yeah. I did. So, that I was just thinking about too, actually. So it it it typically when I go back to Cincinnati, if I'm driving, I try to stay for a longer period of time, and it typically ends out to be about 2 weeks, I can get, you know, 2 good weekends in. But, yeah, we I went back, and I was doing a lot of wedding planning and, like, just wedding stuff, getting my dress fitted, doing some shopping for decorations, meeting with the venue, doing a food tasting, meeting with the, one of my really good friends is, wedding planner, and so she's doing my wedding for free. Oh. So, you know, meeting with her. My bachelorette party, we went away for the weekend, and then the following weekend, we did my bridal shower.
Courtney Osborn [00:40:36]:
So it was just, like, all that stuff, and I still worked full time. With 3 different clients.
Heidi [00:40:47]:
Wow. Without having to be like, okay, how much PTO do I have? Or Yeah. Like you said, just, oh, I can go for a long weekend or something. Yeah. It's huge.
Courtney Osborn [00:40:57]:
Yeah. So that's definitely the highest, for sure. Okay.
Heidi [00:41:01]:
I love that.
Courtney Osborn [00:41:01]:
And also, every time I get a paid invoice, it's just like a little bit of a celebration. It's just like every it's like, validation that I'm doing the damn thing. It's like how I think about it in my head. I'm like, I'm doing the damn thing.
Heidi [00:41:16]:
Good for you. Good for you. Okay. So that feels like super warm and fuzzy.
Courtney Osborn [00:41:22]:
Yeah. So the bags.
Heidi [00:41:24]:
Hard stuff. Yeah. Let's be real. It's not all rainbows and roses. No. Nothing in life is.
Courtney Osborn [00:41:31]:
So obviously, like, prior conversation, that one client, The April, where I didn't have any paid work, and that was a really great learning lesson for me actually, which, I don't remember if I heard this from you. I definitely heard it from someone that like the 1st year of this whole situation is like learning, and then like year 2 is for earning.
Heidi [00:41:59]:
Yeah. I said, I say that a lot. I got it from Mabik Sati full transparency, but year 1 is for learning with an l and year 2 is for earning, and that's for like freelancing, for business, for like any types of things.
Courtney Osborn [00:42:11]:
And so I have kind of kept that in my head too, like every time something goes bad, I'm just like, you're learning. It's you're just learning. You learned from the situation, like, move on. And that April situation was because from January till March, I had enough paid work to get me through. And I wasn't marketing, I wasn't reaching out, I wasn't pitching enough, and so I didn't have any incoming clients. And so when that job ended, and the other things that I was doing weren't working, I went a month without any paid work. And I was like, okay. Don't do that again.
Courtney Osborn [00:42:54]:
Figure out how to work it in. I started talking to a lot of people about time management, and, I talked to Kate Knight about she always has really great recommendations, and she put me on to Austin Church. Is it church? Yeah. I don't know. But he has I I follow him on LinkedIn, and he has a podcast, and so that was great. He talks about like the, morning marketing habit, and the other thing that he said was, do the things that take the most willpower first thing in the morning, or, like, early in the day. Mhmm. Because if you put it off, and put it off, and put it off, it's gonna be the end of the day, and you're not gonna do it.
Courtney Osborn [00:43:40]:
And so I've been trying to work those habits and to get more stuff done, and to be more productive, and, make sure that I've I'm gonna constantly have some type of incoming work. I turned that into positive.
Heidi [00:43:58]:
You did? Was that intentional?
Courtney Osborn [00:44:02]:
Not really. This is
Heidi [00:44:04]:
just how your brain works. Yeah. Your brain has been trained to work this way. Yes. Yeah. It's been through effort that you've gotten there.
Courtney Osborn [00:44:13]:
For sure.
Heidi [00:44:14]:
Yeah. In In a really good way. Okay. So it's been about 8 months. How do you feel about the decision to go down this path versus, like, go become a dental hygienist or, I don't know, some other job,
Courtney Osborn [00:44:33]:
like, where you're at. Grateful, so thankful, so happy. I know I still have a long way to go, but I I see the future and it's great.
Heidi [00:44:46]:
Good. So, sorry. Keep talking.
Courtney Osborn [00:44:49]:
No. I was just gonna, kind of, rip off that. Just, like, you know, I I made it official. I opened, like, an actual LLC because, you know, I do have I own my own house and like things because I have worked very hard for the things that I have, And I don't want the chance of having any of that taken away from me, so I opened my LLC, so I like it separate my business for my personal life.
Heidi [00:45:12]:
Mhmm.
Courtney Osborn [00:45:14]:
Which I do want to just throw that out there. I know that you tell people this, like you don't have to have an LLC. People ask me that all the time, like, oh my God. You did that. Like how do I do that? Do I have to do that? No. You don't have to do that. I chose to do that because I have other things that I need to protect. But anyways, but yeah, I opened my LSC, and that was like, that was really affirming, to be like, I am a business owner, like I have a business.
Courtney Osborn [00:45:39]:
Yeah. When did you do that? January. I think it
Heidi [00:45:43]:
was at the end of January. 6 months ago. 5 and a half months ago. Okay. Mhmm.
Courtney Osborn [00:45:48]:
Yep. And I've also told you I think a few times, but, I hate feeling like I repeat myself to people, because I don't want to reward people, but I know that we're doing this for people other than you. I've heard it. I I try to follow my gut, and my heart, and like when things feel right and feel good, I just follow that. And this is like something that I've started probably in the past 6 to 8 months, and my business name just came to me, and it felt right, and so I went with it. And so it's Courtney, I was born connections, which my initials are c o, and go growing up my nickname was Coco, so, like, I built that into my logo, so it's like c o c o, which just feels cute and kitschy, and just right, and very me. And so everything about that just feels really happy and positive.
Heidi [00:46:53]:
Yeah. Didn't you, like I remember you ran the idea of past me, and I was like, oh, I love it. I really love it. And then didn't, like, shortly after that, you wound up having, like, a fun little conversation with a prospective client about it, who, like, there was this, like, weird little connection or some something?
Courtney Osborn [00:47:10]:
Yeah. So it was actually my my main client that I was working with earlier this year. Her name was Courtney. And so it was sometimes confusing because it's like she and her business partner, are like the 2 main people in the business I was talking to. Yeah. And having it be, like, Courtney and Courtney, and then the other person I was like, if you want, you can just call me Coco, like, that is my nickname, less confusing, and they started calling me Coco.
Heidi [00:47:39]:
I love that. Did you feel let me rephrase that. How did you feel after setting yourself up as an official business?
Courtney Osborn [00:48:01]:
Just I make this dumb joke a lot, and most people don't really get it, but I think it's funny, and I just go, I'm a real boy now.
Heidi [00:48:13]:
I'm a real boy now? Okay.
Courtney Osborn [00:48:18]:
Like Pinocchio?
Heidi [00:48:20]:
Oh, I didn't get it. Yeah. I I'm the person that didn't get it.
Courtney Osborn [00:48:26]:
Most people don't. It's like the stupid way my brain works. Okay. So it's just like, it's real. I did it. I'm a real boy now. Like, I'm a real person, human being who's doing the damn thing, and like, I'm succeeding because I say I'm succeeding, and here I am.
Heidi [00:48:44]:
Okay.
Courtney Osborn [00:48:46]:
Yeah. I've got no strings on me.
Heidi [00:48:50]:
The reason I asked, and I did I was really mindful with how I ordered the question because I didn't wanna lead you into anything, but I've heard and I know from firsthand experience that, like, setting up a business can make it feel more legit, which in turn makes you take it more seriously, which in turn, like, makes you maybe, like, do things that feel a little harder because you're like, well, it's real. Like, I have to do that. Like, you just take it. There's a different level of, of pressure in a way.
Courtney Osborn [00:49:21]:
I would know that was a little bit about that. A little bit. I think because I was already in the head space of, I'm going to make this work no matter what. And so that part wasn't, I think, a big change, but I think the the big change was actually making me feel more professional, like more legit, so I felt better about standing up for myself, and that I was presenting myself to clients in a way that, you know, I'm a real business. I am legit. Mhmm. And I think you could still do that with just branding and a good email, but it just felt a little different me different for me in that way.
Heidi [00:50:08]:
Okay.
Courtney Osborn [00:50:10]:
Because when I did do the LLC, I did create like an actual email, and I made my logo, and like all that stuff, and so it just felt more real. And I also celebrated then too. Like, that's the other thing is I try to celebrate everything, the small things all the time, because why not? Yeah. Life can be good.
Heidi [00:50:37]:
Yeah. You have to acknowledge those moments, or else they they're fleeting. Mhmm. Yeah. That's so cool. Courtney, I appreciate your candor so much and coming on and, like, spilling all the beans because I know it's not always easy. But I hope that after doing this, you are like, yeah, you know what? I rocked that podcast episode, and I was worthy of coming on because you very much are. And I'm really grateful that you, you took me up on the invitation to come and share your, your journey and experience.
Courtney Osborn [00:51:09]:
Yeah. I'm a little bit nervous about it coming out of all my history, but I'm also like, I don't feel bad about any of us.
Heidi [00:51:17]:
Okay. Good. Good. I'll end with the question I ask at the very end, which you know what it is, because you asked me. The What is one thing people never ask you about being a fashion freelancer that you wish they would?
Courtney Osborn [00:51:32]:
So I cheated, and I thought about this for a while. Okay. So I wrote notes because I wanted to be able to make sure I said this correctly. K. And the question that I wish people would ask or talk more about, maybe not necessarily ask me, but just, like, really understand, is do you feel undervalued or underestimated? Because I feel like a lot of people see this industry, this job, as being like, kind of frivolous, and you know, like the lattes and the hair flips in New York City, and like whatever, but it's so much more than that, and a lot of people don't understand it and don't, I think, take the time to want to understand it. They're happy with that surface level vision, and we are so much more, like, most of us have, like, deep deep knowledge in the building blocks that are the literal fabric of our lives, and some of us are extremely well rounded, and understand more than just design. We are business oriented and marketers and project managers and sales people and brand builders, graphic designers, seamstresses, tailors, some cases borderline scientists, and creatives. And I don't think we get enough credit.
Heidi [00:53:04]:
I love this answer so much. And I love it because not only are you acknowledging that for your own self, which is phenomenal because I think most people tend to do the opposite. You're helping everyone listening can now acknowledge that for themselves. Yeah. We're we're good at undervaluing ourselves too. Like, I would almost argue more than other people maybe undervalue us. Sometimes not. But, you know.
Heidi [00:53:38]:
Yeah. Again, a testament to all the personal development and work you've done on yourself, which is amazing and goes really far.
Courtney Osborn [00:53:48]:
Thank you. It's really validating for someone else to say
Heidi [00:53:52]:
that. Yeah. And I admire you on that level, because I know that personal work is hard.
Courtney Osborn [00:53:58]:
Yeah.
Heidi [00:53:58]:
It's real hard. It's not often fun. Where can everybody connect with you and find you online?
Courtney Osborn [00:54:06]:
I'm on LinkedIn. You can email me at courtney at it the email is courtney@courtneyosborn.com. And then my website, my portfolio is courtneyosbourne.com. It is not currently up, but hopefully it is by the time this podcast comes out because I took it down again.
Heidi [00:54:27]:
No pressure. No pressure. Thank you so much for coming on the show. It's really been lovely to hear your story and get to learn more about you. Thank you for sharing everything. My absolute pleasure.