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A podcast where you join me (Colie) as I chat about what it takes to grow a sustainable + profitable business.
CRM Guru, Family Filmmaker, and Host of the Business-First Creatives podcast. I help creative service providers grow and streamline their businesses using Dubsado, Honeybook, and Airtable.
When Roxanne, a brand photographer and storyteller, hit a growth spurt in her business, the cracks were impossible to ignore. She was “using Dubsado,” but only in the loosest sense: contracts and invoices duct-taped to a pile of sticky notes and PDFs. Reminders slipped, proposals lived in Canva files, and every new client meant hours of piecing things together.
The problem? Roxanne wasn’t lacking creativity—her client experience was heartfelt and high-touch. What she lacked were systems strong enough to carry that experience. Without them, she found herself pulling over on the side of the road with her kids just to send reminders, duct-taping together PDFs and sticky notes, and feeling resentful of the stress her own growth was creating.
That’s when she turned to Systems in Session and built a luxury photography client experience in Dubsado—one that matched her brand, streamlined her bookings, and fueled record-breaking revenue.
Within 60 days, Roxanne went from chaos and overwhelm to proposals she could send in minutes, automated touchpoints that kept clients on track, and workflows she could build (and duplicate) herself. The transformation wasn’t just backend—it was financial and emotional. Her calendar filled, her proposals converted with add-ons, and clients began telling her, “You should raise your prices.”
This is Roxanne’s before → after. Here’s what changed and why it worked.
Colie: Hello, hello and welcome back to Business First Creatives podcast. So this is like another client interview type of situation today, but I’m expecting a lot from Roxanne.
Roxanne: Oh,
Colie: You hear her laughing already. So Roxanne is someone who I just barely met this summer and literally cannot imagine life without her.
She has recently graduated from Systems in session,
and I am just literally so sad that I am not gonna get to talk to her on a weekly basis. Unless I just harass her, which is already on my calendar. Roxanne, welcome to my podcast.
Roxanne: Oh my gosh. Colie. Thank you. I was gonna say, I thought you were gonna say I have to go to therapy. ’cause I finally got rid of Roxanne and I or I, I went to church and prayed at the altar and now she’s finally gone. But no, I am. I am good. And you would be so proud of me. ’cause even yesterday I did went back to one of your videos and I sent the form correctly instead of doing it, you know, the 9 1 1
Colie: Mm-hmm.
Roxanne: way so good.
Colie: I mean, actually let’s, let’s start our conversation out with that guys. I’m on my way to Chicago to the airport, and I get this 9 1 1 message from Roxanne. Oh my God, I think I broke my shit, which I was pretty sure she didn’t break it guys, honestly. But I’m chatting with her on the way to the airport and I’m explaining to her, no, you didn’t break it.
You have to use the system the way that it was intended every time, even if you think they’re a special snowflake, which they aren’t. And so once she realized that, she was like, oh, okay. I didn’t break anything. I’m like, no, but I mean, it’s also not uncommon, Roxanne, the first time that someone feels like something is broken.
Even if you’ve already graduated from, you know, systems in session or me doing your systems for you, I do get panicked. 9 1 1. Emails that are like, oh my God, I think I broke something. It didn’t work as expected. And usually it’s either a, I have to re-explain it to you, or it’s like a five second fix, which is fine.
Roxanne: Well, and I have to shout you out because, and this is what I, I am a part of Maddie Peschong’s, group coaching program as well, which is amazing. And I, that’s how I heard about Colie, that’s how I started, you know, stalking on, I love a good online stock. I’m like, no, I like Colie. She’s my people. But then I, I was like, after that happened and I, started working with you.
The best part, and this is why I like. I am like Colie’s the goat is because you can send her a problem and a lot of times within an hour, well sometimes within minutes you’ll have a response. And that is like key because all of us that are in business know like if I’m trying to send a proposal to book a client, I need that answer.
So I really appreciate it. Plus then we got to talk in the, in the car ride to the airport and I made sure that you were going to eat all the things in Chicago. ’cause Chicago is where your girl lived for fif almost 15 years. So I’m very concerned with people. What they eat when they go to Chicago because we have the best food.
Sorry.
Colie: I mean, and I did.
Roxanne: does not mean for me to be skinny, the Lord. It is not in his plan, so
Colie: And I did, I ate really, really well when I was in Chicago. Mostly because Anneme from this can’t be that hard, made all of our reservations and she like pre-planned the things. I mean,
this Was a different kind of working weekend. I have been joking around. I feel like it was more of a girl’s weekend than it was a working weekend.
’cause I really don’t feel like I accomplished shit. I mean, I did. I fixed a whole funnel. So I did, but in comparison to like when Sabrina and I stay in a hotel together and we don’t do anything but work for like 14 hours and only take meal breaks, I felt like this was like a different kind of situation.
But it’s all good. I mean, we, we had a blast. It was definitely what I needed it. Now I’m home like doing a lot of the things that I should have done when I was in Chicago.
Roxanne: Right, right. That part. No, but I really appreciate this and this is something that I had been, waiting to invest in and now like, you know, I’ve already like tried to send people your way. I’m like, if you are thinking about this and not doing it, you’re nuts because the, the impact on your business is.
So quick, like I feel like a lot of things we do to invest in our business, personal development, coaching mindset, it just takes a while to like get in there, right? And for it to really impact. But this was like, no, no, no, no, no. Like in three days I’m sending proposals, people are adding on things. I’m booking, I’m sending a proposal in 10 minutes.
Colie: Yes.
Roxanne: like, what is I told her, I was like, you’re wizardry. I’m here for it. Whatever witchcraft wizardry you are doing, I want more of it.
Colie: I mean, and it’s interesting because it’s, it’s part of like my current shift because I feel like I used to talk about you need the whole system, you need everything to work together. You know, you need all four phases of your client experience to be done. And now I’ve really taken a step back because I do feel like there are a lot of people that need to experience the micro wins.
So that
they can be convinced of the systems overall. Because you initially contacted me and you were like, Hey girl, like I need a proposal. Like you were just like, Maddie, you and Maddie are twins in this way. You were like, I just need a proposal and I want it to be just like Maddie’s and how much will that cost?
And so on our first call, I was like, okay, you know, you could pay me $600 and I’ll do. Or you could join this new program that I have called Systems in Session for 2K and we’ll do all your systems together. And you, you know, you took a minute and you were like, okay, yeah, I’m in. Let’s do the whole system.
Roxanne: Well, and I think like I was like, a lot of people are, and I’m very like open and real, right? Like my brand is like, you know, I’m a lot and so I’m not for everybody, but I am not trying, like I always say this in business groups too. I refuse to be in spaces where I have to puff myself up to try to pretend like I’m someone I’m not, or to make myself smaller.
I’m not willing to do either of those things. And for me, I knew my work was there. I knew my, the way that I make my clients feel, the confidence I build in them. All of that was there. I needed my systems to match that so that I could increase the pricing and value. Because I was not about like, and this is what I told Maddie too, I’m not just like, I just wanna keep raising my prices.
No, I wanna raise the value so that it’s like you’re insane if you don’t book Roxanne. Like you are literally nuts. You have lost your ever loving mind. And, but that has to be all of it. And I think I was one of those people, like your brain, when we were on calls all the time, I was like, Colie, don’t, don’t hate me.
I have to go talk to my therapist after this. Like, because I had been telling myself, right, for the longest time, I have a DHD, I’m neuro divergent. And I found that out as a whole grown ass woman. And I’m like, oh my gosh, so much. Makes sense. So I had always had like the creative pieces and that, but I, the systems part, I had been telling myself in my mind that that’s just not my thing.
can do my business without having that. But what that was doing was actually justifying me, holding myself back. And the truth is, I did need help to do it, to be clear, like I knew once I talked to you, I am not the person that could just purchase like the steps and then it’d be, it’d be fine. I could not do that because I needed the ability to work with you for a couple of months, but to have a fire lit under me to be like, girl, take advantage of this.
I booked calls with Colie. She saw my, she listen. She was my bff, whether she wanted to be or not. She saw me every single week and I was working on things slowly, but that is the process I needed. I needed someone to do it alongside me. And you are. So good at explaining stuff to someone who is clueless without being judgmental or rude or like, and also just helping wherever our business is, help us not to become someone else, but to help.
Like what do you need? Like your first call, I knew I was gonna love working with you. ’cause it was just, I think it was like 45 minutes of you just asking me what’s wrong? Uh, what could we do better? What, where are like the, the, the pain points in your, um, usage right now of your CRM, and then you made a plan for us to do that.
And then we did it together. So I’m like, now I, I literally have told people I made back my investment with you with two proposals.
Colie: Yes.
Roxanne: So I, and I’m like, what, what are we 14 proposals now
Colie: Mm-hmm.
Roxanne: I started working with you. So I, it’s like, and that’s only been less than a month. It’s, it is crazy.
So I’m like, guys don’t, if you’re one of those people that’s like, I’m super creative, this is where I thrive, absolutely. But get the help you need to make sure that all of your business is that amazing of an experience. And now I feel really good. I actually co, I didn’t tell you this, but I had a client on, Tuesday, she said to me, you need to raise your prices. And I was like, I just did, but I will again. But she was like, this experience has been so great. I had another client tell me last week that she screenshot some of my emails ’cause she’s like, I’m starting a new business and I wanna do some of what you’re doing. And I’m like, it’s all in my CRM. I was like, I got a girl, I got a Chica.
I’ll send you two. So I’m really grateful.
Colie: I mean, I love hearing all this because I think one of the things that I was really worried about putting this done with you offer out there is are there actual people that want to like get in it with me and do it step by step? Because I’ve always had the course that really shows you step by step with videos, but it doesn’t include me.
And then there’s the part where I, you know, do it all for you. It’s funny, I just got re-certified through Dubsado and you have to fill out a questionnaire before you take the quiz to like prove your knowledge again. And one of the questions was, you know, what are you doing to offboard your clients after you work with them?
And when I entered my s. response. This time it was so different than like last time. This time I was like, oh, I don’t even have to do this anymore. I’m like, the whole process. We’re doing it together. So there is literally no offboarding process. There is a, Hey, can you fill out this questionnaire so that I can help other people and change my processes if I need to, but I don’t have that formal giving you a video explaining how everything works, scheduling a call so that I can walk you through it and answer your questions.
You don’t need that when you leave systems in session. Because we did the entire thing together. Like you’re the one, yeah.
Roxanne: yeah, and I have the videos of
Colie: Mm-hmm.
Roxanne: saved them and I literally put them in my email as how to send a proposal, stupid, like so I literally just searched. Proposal’s stupid and it comes up and then I can do it now. I’m not gonna need that after another week or so, but it’s there and I, I think this is key.
If you’re a person in business right now listening to this and you’re ’cause not every, this is what I always say to people, not everything is for everybody, but it is really important to know how you operate best and how you learn. I knew, well, one, the investment of Colie doing everything for me. I was like, your girl ain’t got that money right now.
I’m just gonna keep it 102. I also knew though that if I did that, I wouldn’t learn. this works. And I have huge plans with my business, right? To morph into new things, to do other offers. Like I wanna be able to build this myself as needed, and then just maybe schedule, you know, one-offs with Colie for that support to make sure everything’s working.
But like I knew that I’m the type of person that learns by doing, but I need accountability and I need somebody with me to explain the stuff so that I don’t throw my computer out a window, which, you know. I did do once in college, um, before that was like, your girl was only in therapy a couple years at that point.
You know what I mean? I did throw it off a, a balcony. It’s fine, everything’s fine. Everyone should mind their business, but I. I don’t wanna do stuff like that. I don’t wanna like feel that like, um, I can’t do this, like overwhelmed. And so for me, I’m like, I can do this, but I need help and support and there’s no shame in that and there’s no, because there’s a lot of things that I can offer help and support to other people in, like, my clients come to me because I’m an expert in.
What visuals will tell your story in a unique way. They don’t have to know that when they come to me. They just have to be willing to answer the questions, go through the process, be a part of everything, and then we create it together. So it’s just kind of like knowing where are your expertise in business and then where are the things that you need help with?
And I think I am allergic to this like. You know, I’m trying to play a successful person on Instagram. Like if you’re trying to pretend like you are good at everything, I’m sorry. Everyone knows that that’s not true. Nobody is good at everything, so like. out how to bring amazing people in your corner to help you get what you need to be amazing.
But not everybody’s good at everything. So it’s not a weakness of mine as an entrepreneur to say, Hey, my systems were the weak point, because my client experience was on point. My photos are amazing. I just was like, I need this to be better because also I have four kids, a busy life. I created all this.
resources for my clients. I don’t wanna ever miss sending them something, right? And so like I have a discovery call today. When we get off this, and I know I’m gonna actually look right now, I’m gonna go into the subtle, I know it’s gonna send an automated response to my client because we set that up and I don’t have to remember that, you know, before I was doing a lot of these things, but I was duct taping it together, piecemealing it together, and I was like, oh shoot, I forgot to do that.
So I’d pull over on the side of the road with my kids and quick send. Something like that is, I don’t, that’s stress I don’t need in my life. Life is hard enough, you know what I mean?
Colie: It is. And I will say, going back to something that you said about being able to do it yourself, you’ve actually already done that and you’ve only been out of like my hands for a few weeks now. So you and I created your main offer together, which is your signature brand sessions, but that’s not what you send to people who are doing like commercial jobs or organizational storytelling.
So after we set up like your personal brand client experience, you took that and duplicated everything and customized the email and customized the proposal all by yourself. I was so proud of you. And then you’re like, okay, Colie, I did all these things. Can you make sure that I didn’t fuck it up? That was
basically what you told me.
Roxanne: and make sure it’s not broken. And I will say this, you guys, when you work with Colie. was what was so cool. She helped me also with little things. Like, this is why I know this is, this is who my people are. am not a gatekeeper. As long as you value my time, I will give over and abundant to you.
Right. And Coley’s the same way I, in my opinion, because she didn’t have to take that call on the way to the airport. But, but then I, she was like, she told me, you’re dead to me when I’m in Disney. I’m like, no problem girl. I get it. You know? Um, so she has obviously has tons of boundaries. So do I. if someone values me, I will go above and beyond.
And a couple things you did that really were like Colie for me, is, um, you helped me like realize I was attaching like my investment guide by PDF, right? So I’ve been changing my prices, changes, changing my offerings, slightly changing, you know, now I have a videographer, she’s amazing that I’m working with.
So you were like, no, no, no, no, no. Let’s make that a public link so that every single time you update it, you don’t have to go into your system and reattach anything. And those little things are like, oh my gosh, she, she anticipates your growth and she’s for you. And that, and like you helped me make my discovery call link a public link from my website so it doesn’t look bootleg as a long Dubsado link.
Right. But like, just little things like that that. I don’t know what I don’t know. Right? And there’s no gatekeeping, there’s no like, oh, well if you wanna do that, you would have to do this, um, and pay me more. Whatever. It was like, there was just a, an abundance of help. And never once did I feel like I’m a mess of a human.
Even though I would joke with her all the time, I was like, Colie, you might need therapy after today. Because listen, I’m triggered by the fact that like, I don’t, I’m afraid once we automated my stuff, you guys, when I tell you the pit stains were real about, it’s gonna go out wrong. You know what I mean?
Cole laughs. She does, she don’t act. Right. But I’m like, I literally was. So if you’re one of those people that’s terrified of automations, ’cause you’re like, they might go out wrong. Work with Colie because she will test it all, show you what’s coming, make a video of it, and then any, ’cause we did have a couple little snafus, so we, before I went out to my class, we went back and fixed it all.
You know, and like very successful people, you have to, you have to risk going to the next level in order and, and, and making some mistakes in order to figure out what you need to tweak. So I just wanna say, don’t be afraid of that. ’cause I was afraid of that for so long, for no reason. Really. So yeah, I appreciate you because you are, you are in it to really see people win and I appreciate that.
’cause I would be like, every call I got on, I was like, Colie, they added video Colie, they did the proposal
Colie: I mean, you, you know what I need you to do? I need you, not now we’re gonna do it when we’re done, but I need you to go and like add up how much you’ve made in add-ons, just simply since I told No, you need to just put it on there and add a price and we’ll see if someone books. And then when you first showed me what your add-on B roll was, I was like, oh.
That’s too cheap. So I’m gonna let you put it on here for this for now. But when you book like three of ’em, I need you to immediately double that.
Mm-hmm.
Roxanne: my videographer that has been partnering with me. She is amazing. Shout out to Honey Drip Media. She, we’ve already talked about this. I was like, but we wanted, again, this goes back to I, we wanted proof of concept. We wanted to make sure that the value was like so insane that people would be like, um, yes.
Because I it whenever you’re doing something new, I, I think a lot of, especially I hear women in business struggle with this all the time. Like, oh, I have imposter syndrome. I have reframed that into like, shouldn’t we all have a little bit of imposter syndrome when we’re doing something brand new?
Colie: Yes.
Roxanne: Like if you walk, if, if you walk in to give a TEDx speech and you ain’t never even talked at the PT.
should feel a little bit of imposter syndrome, right? Because if you don’t, you’re probably, you probably are a narcissist or something, right? Like there might be a problem. I am like, I am not feeling imposter syndrome is just part of my process of growing to where I’m like, let me make sure, but I’m gonna deal with it.
I’m gonna go to therapy, I’m gonna talk to my, self and I’m gonna make sure that the value’s there and then I’m gonna unapologetically charge the value. You.
Colie: Yes.
Roxanne: but I think that there is that piece of, like, we, we were figuring it out and I’m like working with a stylist now. I have a, a visionary VIP session, um, which is so cool because when I launched that it was from feedback from another client, like I would’ve, this was amazing.
Your process is amazing. I would’ve loved even more help with like styling like team. And I was like, oh my gosh, okay, people would pay for this. Let’s do it. Started talking to local stylists and I pay women what they asked to be paid, so I had to obviously raise to make sure that they were being paid. And then now that we’ve done it, my goal was to book one
Colie: Yeah.
Roxanne: the end of the year.
I think I’ve booked three or four.
Colie: Yes, you have.
Roxanne: And I’m already gonna, I’m already gonna up that because now I know the value, the, the video that, Akila is creating for my clients with the photography, the value is insane. It’s like a year’s worth of content for people in one day. So I’m like, this pricing has to shift again because of the value and because, and also I’m realizing how much time I’m,
Colie: Mm-hmm.
Roxanne: um, putting out, you know, working with all these people.
Yeah, it’s not about like, let’s add stuff to see if we can upcharge people and rip them off. Like, that’s what I appreciated about you and about working with Maddie. For me, alignment and like I’m, uh, you know, I’m not, my goal in life is not to, I wanna make X amount. My goal is to serve people really well with the gifts and talents that God has given me and to continue to grow and be excellent at what I do and to make sure that my family’s first.
So. My goals are just not up for discussion, you know? But I do want to unapologetically earn money for my time because I have a ton of skills and Colie helps you. Figure out how to do that with less stress and with less friction for your clients. And like you guys, when I tell you my proposal, like I, I told my husband when it first went live, I was like, come over here.
Look, it looks like a website. I was like, look how legit I look. Look how legit I look like it’s okay to get excited about that stuff. Like geek out about it because it like, you know, I started 10 years ago feeling guilty for charging people 50 bucks. Right. And look at where I am now, you know, because, and, but the values there, I have a client tell me to raise my prices.
So I just, I’m super excited for this. I’m mad. I am not even mad, but I’m like, I should have invested earlier. it all happened the way it was supposed to. ’cause I found you through Maddie and she’s amazing. so it just, if you are thinking, I, I don’t know how to invest in my systems because like, I just don’t even know what I need.
Colie knows what you need. Like literally you just tell her the issues you’re having and then she will walk you through with this process. So, and not everybody, this process is for them. Maybe some people can do just the course and bless them, bless their hearts. I’m new to the south, that’s what we say.
Bless, bless their hearts. but that’s not me. Your girl needs like some handholding, some help that’s me.
Colie: I mean, and it’s funny because two, two different coaches, I mean honestly, it might’ve been three, but at least two different coaches told me, no, do you need to give them calls and support tickets? I was like, yes. And they were like, okay, but like, do you need to give them that much availability for the calls?
I was like, yes. I was like, I don’t think you guys understand, like this is where I’m going with my business and I don’t mind talking to people. All day long if it gets them where they need to be. And ’cause like now, now I have days where I am on, I am on like seven or eight calls a day. But the difference is.
Now I’m on a call and I’m walking you through what you have to do. And then like you said, when I go to Disney, you’re dead to me. Literally when I get off the call with you, I send you the link and I tell you what your task is and you are pretty much dead to me until I talk to you again or you send me a support ticket.
So like the way that I am doing it now is just so much different. I am giving you more of my time in terms of like I am getting on a call with you. I am answering your support tickets, but. I am not doing it for you, and so this is really good for me because I can literally turn you off and not have to think about you until you come back to ask for feedback or ask what the next step is.
And so.
Roxanne: Yeah, and I feel the same way about my system now with my clients because I give them so much of myself, but like, until they submit the questionnaire, you’re dead to me. Like you got, you’re gonna get your reminders, you’re gonna do that. Like, but we, because, because listen, I told them in the discovery call what the process is.
I can’t create amazing personalized brand images without you. You’re the brand. So my client’s like full disclosure of what this process is, and then, but now my systems support that boundary so that I can just send them those reminder emails instead of me before I would get emails like, what am I supposed to be doing?
And then I would personally answer those emails. Now it’s like, no, they just get those reminders and like, Colie, you ain’t stupid because you know this because I like you giving us that attention though too. I, this is the same way I operate my business. This is the same way Maddie operates her business.
She is very available, but she has a lot of boundaries. You are very available, but you have boundaries. me, that is what makes people sing the gospel of Colie, right? Because I’m like, she got me this, this transformation. I’ve already told all these people, I ain’t get paid nothing. I don’t even have no affiliate link.
Listen,
Colie: She’s mad. She doesn’t have an affiliate link, y’all.
Roxanne: I’m like, where’s my affiliate link? Colie? Um, but, but it’s because I truly believe in the, the benefit of it. Whereas you could, and, and, and every business model is different for every person, right? You could have it where you don’t offer that as much. And I go through it and then like in two months I’m like, man, I don’t, I kind of regret spending that money ’cause I don’t really know how to use my system now.
I’m not gonna ever tell anyone else about you.
Colie: Hmm.
Roxanne: That’s just me, right? Like, because I didn’t feel like the value was amazing, right? Because I got a bare bone system, but I didn’t get the support to implement it in real time with problems that come up. And that’s the same thing, like I want my clients to feel like if they call me the day before and they’re like, all of a sudden I hate this outfit, I’ll be like, okay, let’s, let’s help you figure it out.
Because I could have a boundary there and sometimes I need to, but for me it’s more about how can I make sure that our goal of this person showing up as their most confident, self aligned, authentic imagery happens not only for them, but I’m smart. I want that so that they then tell other people about me.
And that’s, you do the same thing because it’s like if you overdeliver for somebody. And the value is there for them. They will then tell other people in their circle. And that’s how our businesses grow organically. Like, I haven’t done ads or anything like that yet, and I’m fully booked out. I just moved to this area.
Um, and part of that is my, my proposals that I can send in three minutes
Colie: You can,
I’m.
Roxanne: I used to, I used to make a custom proposal for every single person in Canva, guys, and then attach it and send it, and, oh, blessed Bee, blessed Bee. And now I can literally send a proposal while I’m on a discovery call and they can book within 10 minutes.
Colie: Yes. And I love that for you.
Um, it was funny when I was making my, um, offboarding form, um, my business coach added a question and she’s like, how long was it taking you? To like respond to people initially and how long is it taking you now? And I was like, no, we can’t ask that question. I was like, ’cause my clients don’t have a choice.
I was like, they respond to clients instantly because they have an automated email that goes out the amount of time that it’s taking them to send a booking proposal. I don’t want anybody just saying less than an hour, it should be less than 10 minutes. But how about we make it 20 just to give them a buffer.
I was like, I don’t expect any of my clients to spend more than 10. Maybe 15, 20 minutes getting the proposal ready and I mean, it would have to be some heavy duty changes for it to take you 20 minutes to change
something.
Roxanne: And I do have that occasionally. Like I had this back and forth and I had to take stuff and make a custom one.
Colie: Mm-hmm.
Roxanne: like, and when, when we, we say proposal too, like I think before I was in systems and session, I had no idea even what that looked like. This is what I want you guys to understand, like what I’m talking about when I send a custom proposal now.
has their logo on it. It says, Hey, Colie has her logo. It says, because Colie is gonna book me at some time in the future for a brand session. Listen, I’m gonna send her her own damn proposal. She go check all the boxes. but it says, it has like my little checkbox that says like, you know, I understand for time and travel, dah, dah, dah.
All of it. It has my images on it, it has my client reviews, it has my process, it has a picture of me with, Hey, this is who I am. Thank you so much. It has a click link to go back to my website if you’re doubting, because like I really do. people when they get that proposal for it to be a confirmation of the conversation we just had on the discovery call and for them to be like, oh, this is an easy yes, this is the
Colie: Yes.
Roxanne: spend the next, in the next year, right?
Because I feel that way about kley. The best money I’ve spent in my business this year was Maddie Ashong rebrand, retreat, and Colie James a hundred percent. So that, that is like what I want. And so that is what a proposal is. It is not just like a. sending some dry invoice. It is customized to them to where, because that’s my experience too.
I’m gonna customize their guides and I’m gonna customize their experience, so I want them to feel like. You know, this is all there for them, but I also want them to make a decision, get on my calendar so that I can totally elevate their experience, treat them well, but I want them to pay me money right away
Colie: Yes.
Roxanne: this process.
And if you make the friction less, we all have been on those websites where you just trying to buy a cute pair of shoes and this thing is so dang frustrating that forget. Those people are dead to me. I was gonna buy those, those little wedge heels, but you’re dead to me because your login process, it sucks, or whatever, whatever.
So Coley’s like, don’t ask them for their name twice. Don’t ask them for their email twice. Like everything she does is based in like how user experience, how to make it easy for them. So I really appreciate that.
Colie: Absolutely, first of all, she mentioned rebrand. When this is live. Maddie is currently open for enrollment. So if you do not have information on
Maddie’s services,
Roxanne: Y’all better reach out to me and use my link.
Colie: uh, give me your link. I’ll put it in the
show notes. but I mean, part of it is, and I feel like this needs to be one of my next, podcast episodes is anxiety and avoidance, because I feel like those are the two words. Not only when, when it comes to making your systems, but also like brand photography, right?
We’re all worried about how we’re gonna look and if we need to lose those 10 pounds, and how is she gonna know my business well enough in order to tell my story and photographs. But that’s why you hire a professional. And I mean, I’m not just talking about Roxanne and I, I’m talking about in general.
It’s why you hire somebody to help you with your website and all of the things. And so. Just keep this in mind, just like Roxanne said about her brand photography. She’s telling you, you don’t have to come to me with the answers, I craft the answers for you. All you have to do is be willing to show up and answer the questions that I ask, and tell me about your business, and I’m gonna lay out all the things that I think that you should do.
And
Roxanne: an expert in asking the right
Colie: questions. Yes.
Roxanne: know what questions I should be asking. Do you know what I mean? And
Colie: Mm-hmm.
Roxanne: you just hit on is a good point because some, a lot of people get to. Glass or like ceilings in their business. And especially I see this more in women, men just tend to like be more confident in their skills, even if, even if they don’t have them, I don’t know.
But like we get to these ceilings where we’re like, oh, I’m DIYing everything. I see this all the time with people with like their brand photos. And I’m like, DIY business sends the, sends a message though. It sends a message, and if you want to go to the next level, it might take you getting over some of that imposter syndrome, anxiety, avoidance of things, you know, because everybody leans into what they’re good in.
if you are at a ceiling, you’re, you’re not booking as much as you would like. You, you know, you need to show up and change something and do something different then you’ve always done. I think people are like, well, I’m just being consistent, but babe, if you’re being consistent and it’s not working, then we gotta
Colie: We gotta shift.
Roxanne: Right. So it’s like, I think that that’s right. Like I literally joked with you all the time, like, I need therapy after this. But part of it was because, like makes me like choke up a little bit, like believing that my business was worth investing. investments I’ve made over the course of the last couple years was huge for me because I’m a mom of four.
I started this as a side hustle, charging 50 bucks and to be where I am at, I never, I could never imagine the business I have today, three years ago. Never. that’s because I finally decided to take myself seriously. If you’re not taking yourself seriously, why would you expect your clients to take you seriously?
So I think that this is huge, like dealing with the parts that are emotional, that are tied to your feelings about your worthiness being in all these things. But like if you are DI ying everything, we need to talk because there are things that other people do better than you pay them their time, invest in them.
And get every squeeze, every ounce out of it. I squeezed ev, I squeezed the lifeblood out of Colie. Listen, listen. I fed her tickets like it was my job, but it was like it. That is, that is the part of this that is brilliant because you can get what you, what you need. So, sorry, I, I love what you just said.
You do need to do that
Colie: Yes.
Roxanne: that that’s huge for a lot of people are at that stage where I know I need to invest, but
Colie: Mm-hmm.
Roxanne: Well, if you keep saying, but you’re not gonna have the business that you could have.
Colie: Yeah. And I mean, the other thing that I wanna say to that is, this kind of goes back to the shift that I’ve had in the last year over trying to get people to do it all at once versus doing what you are comfortable with in the moment. If Roxanne had just hired me for the proposal and we hadn’t done any of the rest of her systems, she still would’ve made her money back the first time that she sent a proposal.
While I’m saying, you know, working with me, she would’ve gotten it back. I don’t just mean hiring me to do the proposal for you. I mean, you taking the time to make sure that you have the, the, the proposal that will let your clients book you fast so that you can stop wasting time going back and forth. And then what do you do at that time?
You either reinvest that time. Into creating more systems for your business or marketing your business so that you can book more clients or spending more time with the clients that you already have. Or take your four kids to a trip to Disneyland. ’cause just like Roxanne said, that, you know, she’s eventually gonna, uh, do my brand photos.
I mean, if she takes her kids to Disneyland, I expect to get an
invite. ’cause I will show up with a camera. I don’t
even.
Roxanne: at dawn. We ride at dawn for Disney.
Colie: And so I just, even though Roxanne is here to tell you about systems in session and basically the entire glow up that her business has had behind the scenes with her systems, I want to encourage everybody who’s listening there are baby steps and there there are baby steps that you can take and not even pay me like.
I want everyone to have systems that help them show up in their business as the confident business owner that they want to be, and that they know that they can be. Because what you deliver is often separate from how your client feels while they’re experiencing your entire process.
And you know,
Roxanne: that part.
Colie: yes. And when it comes to Roxanne, you know, she actually has a lot of touch points.
And so for Roxanne, it wasn’t as much as. Like identifying the touch points as much as taking her out of them,
because she was definitely the bottleneck. I mean, she had an amazing process already. She was already sending the emails, creating the forms, making the Pinterest style guide, like planning all of these things.
But she was keeping track of all of it in her head or like with a random ass piece of paper. I don’t know. But she was
spending way.
Roxanne: Is she a hater? She a hater. I’m out here with my, I have so many random piece of paper. You a hater?
Colie: But I mean, she was spending so much time trying to keep it all together and figure out where her clients were. And so what the systems allowed her to do was kind of take a step back and let the systems do all of that, like management for her, and now she really can spend more time with her clients on shoot day or having those conversations with clients when they need, you know, a little bit more of encouragement because they hate that outfit that they love two weeks ago and they spent $300 on.
So.
Roxanne: and if you’re feeling that any of that resentment in your business, I, my therapist a long time ago said to me. Resentment is a you problem, right? So if you are resenting the time you’re spending doing these things, something needs to change. needs to change. Now, I, I kind of resent, like making dinner for these people in my house every single day.
Like, you know, some days it’s just like some of life you’re just gonna have those issues. But for me, in my business, what I realized is when I took a look at my goals, I was like, I wanna be booking one to two of my kind of signature brand sessions a week to reach my financial goals. But if I do that, I actually have anxiety about how I would keep it all together.
Colie: Yeah.
Roxanne: of all the touch points I want and all of the personalized attention. And so now, but I did not wanna lose any of the like Roxanne magic because I do, and I have done a lot of work on myself. I know that you can get brand photos by a lot from a lot of people and there’s a lot of brilliant photographers.
I am brilliant at making people feel seen. I am really good at helping women step forward, especially into competence. and, and I’m ethically, I’m certified in ethical storytelling, right. I have a lot of gifts. As a photographer, I know that now what I needed to stop doing was if, if, if like your goals actually would create more anxiety in your business.
You need better systems because me doing like booking the way I am booked right now for, um, September, October, and November. months ago, that would’ve created so much anxiety because I would’ve been like panic, checking my emails to make sure I had sent them. I would probably have copied and pasted it and sent an email with the wrong name.
Right. I just little things like that because that’s my a DH adhd. I don’t pay attention to
Colie: To the details.
Roxanne: the details are rough sometimes. Um, except in, except in a screen of my, of my camera. But, um, so this was like a way for me to see. Scale, right. Or grow, I guess grow is the better word. Grow without adding so much more anxiety.
It’s, it’s very cool. It’s like an amazing thing to me. My husband and I just went and celebrated, um, I had the biggest month I’ve ever had in 10 years of photography.
Colie: you did.
Roxanne: And we went and celebrated at dinner and I said, but I’m less stressed than I
Colie: Yes.
Roxanne: half as. Half as much. So that is key.
That for me was key. And I still get to have the personalized attention in those emails are written and they sound like me. Um, I still, there’s a bunch of partial parts of my workflow. That send me a notification to go and in there and, um, edit it and approve it so that it’s always custom, right? So systems does not mean depersonalization systems does not mean that then you are just like sending no value to your clients.
That’s not what it means. It means that you value their experience so much that you’re not willing to leave it to chance. Because listen, the wheels fall off at my house a lot. I have a chronic illness for children. If you don’t think that this place is a nuthouse after three o’clock. Uh, come over and hang out.
So I’m like, I can’t leave it up to me. As good as I am at certain things, I’m not gonna always pay attention to that. So it was like taking the bottle exactly like you described. Making sure that I was not the problem in my own growth.
Colie: Yes.
Roxanne: I didn’t wanna be the problem in me growing to where I wanna be.
So, girl, you know, I love you. I’m so, I wish I’d kiss you on the face if I was with you. I’m so, I’m so grateful. It was the best investment. I’m gonna keep singing the praises. I want an affiliate link at some point. I’m just saying.
Colie: Guys, everybody needs a hype woman like Roxanne. I mean, literally I feel like, I feel like when I am feeling a little down about my business, uh, Roxanne is who I’m gonna get on the phone
and just be like, Girl.
can you just have a little chat with me? But Roxanne, first I wanna say thank you so much for trusting me with your systems
inside of systems and session.
Also, thank you for joining me. You know, for this podcast
episode, guys.
Roxanne: fun. I’ve listened before, so now I’m finally on it. So fun.
Colie: Uh, her business is Hawa Images and she is out of Raleigh, North Carolina. And so if you are near there or any of the places that she flies, I would highly recommend that if you are in need of brand photos. And I think this is the first time I’ve ever given a photographer a shout out like this on my podcast,
but you should definitely check her out.
If you have any questions about systems in session, please, you know, feel free to send me a dm. Uh, I would also venture that if you drop into Roxanne’s
dms on Instagram, see? Yeah, that’s what I
thought.
Roxanne: been sending voice memos back and forth with somebody that I told her, if you don’t, hi, hire Colie. You’re stupid. No offense, but like I’m just telling you like it is.
Colie: So I just wanna say. Systems in session is definitely where I’m going going forward and having clients like Roxanne who have had the success that they’ve had and the confidence that it has built in themselves for the systems and really for their business overall because she’s the third person that raised their prices while they were inside the container after having a lot of anxiety about doing so.
And then the very first person that got the new proposal with the new prices booked no problem. Like. This is what I want for everyone. Regardless if you hire me or not.
Roxanne: Yeah,
Colie: Just point blank.
Roxanne: Yes. And the value that you offer in so much, like even just for free, right? Like that, that’s to me too, how I knew, like I’m like, I was listening to the podcast and you know, again, I’m a, I’m an online stalker, so I was like, oh, she’s a real deal. She knows what she’s talking about. And I knew that you weren’t afraid to, like, you weren’t, you weren’t playing a successful person on Instagram.
You were a real person and you
Colie: Considering that I hate being on Instagram, that’s totally true.
Roxanne: I love Instagram. Listen, I, I’m struggling on LinkedIn. I’m like, what? Y’all are not funny over here. I don’t, I don’t understand what’s happening and people are not, they don’t like my jokes over on there. Um, yeah, I just, if you’re thinking about it, ask the questions, make sure it’s for you. Um, ’cause Cole, you still offer those free
Colie: I do.
Roxanne: if it’s, yeah.
So that’s what I did. I jumped on the call and I said, listen, I know I need this. And it wasn’t like, uh, same thing with my discovery calls. It’s not this gross pressure upselling situation. It’s literally Colie saying to you, what are the things in your business you need fixed? We could do this, or we could do this, or we could do this.
And then she gives you. lays it out, she has her expertise to, to bring to your, your problems and what solutions she could help you with. And then you decide, pick what’s aligned for you. But I literally, I mean, I can’t guarantee nothing, but I promise if you do the whole thing, you will make it back so quickly.
Like, I’m just like, why didn’t I do this six months ago? So yeah, it, it is, it is definitely something. And if I need help in three, four months or if I just miss her, I’m just gonna book a call.
Colie: Yes.
Roxanne: She’s gonna be, she’s not, she’s not gonna get rid of me now, so.
Colie: Well, you know, I’m actually waiting for some of you guys to re-enroll for another 30 days in Q1 of 2026. One person already told me that they were gonna do that because now I’m letting you guys come back for 30 days at a time if you need, you know, like a refresh or whatever. But you know,
this is this.
Roxanne: offers,
Colie: Yes.
Roxanne: yeah. That’s a great idea. Yeah. Yeah. Yeah.
Colie: Yeah.
All right everybody. I hope that hearing from one of my actual clients on the podcast has helped you get like a little bit more clarity in what systems and session is and whether or not that is a viable option for you to design and implement a brand new client experience inside of your business. But that’s it for this episode.
See you next time.
I’d been telling myself forever that I was just ‘not a systems person.’ I’m neurodivergent, creative, and always felt like I could get by with duct-taping things together. But the truth was, I was holding myself back.
I had four kids, a busy life, and a growing business. The client experience I delivered in person didn’t match what was happening behind the scenes. I wanted my systems to reflect the value of my work—so that when I raised my prices, clients would feel it was a no-brainer to book me.
That’s why I knew I needed help. Not just someone to build it all for me—I wouldn’t learn that way. I needed someone to do it with me, to hold me accountable, explain things without judgment, and make sure I walked away able to manage it myself.
Together we designed and created a seamless, luxury photography client experience in Dubsado that finally reflected the value of her work.
I was like Maddie—I just wanted a proposal. That’s literally how I came to Colie. I told her, ‘I need a proposal like Maddie’s. How much will that cost?’
On our first call, she said, ‘Okay, you can pay me $600 and I’ll build the proposal. Or you can join Systems in Session for $2K and we’ll do your entire system together.’ I thought about it for a minute and said, ‘Okay, yeah, I’m in. Let’s do the whole system.’
For me, it wasn’t about just raising my prices for the sake of it. I wanted my systems to match the value I was already delivering in person—the way I make my clients feel, the confidence I build in them. I wanted people to look at the full experience and think, ‘You’re insane if you don’t book Roxanne.’
And it worked. I made my investment back with two proposals. Since then, I think I’m at fourteen proposals and counting. That decision changed everything.
Oh my gosh, yes. The pit stains were real. I was terrified that something was going to go out wrong or that I’d break the whole system.
That’s why working with Colie was so helpful—she tested everything, showed me exactly what was going to happen, and even made Loom videos I could save. I literally have one in my email titled ‘How to send a proposal, stupid’ because that’s what I typed in the search bar when I needed to rewatch it.
Even after I graduated from Systems in Session, I was still sending her messages like, ‘Can you make sure I didn’t mess this up?’ But the truth is, I was doing it. I duplicated my main workflow, customized the emails, even built a brand-new proposal for commercial work all by myself.
I realized I wasn’t breaking anything—I was learning. And that’s when it shifted from panic to confidence.
Faster bookings: “I used to make a custom proposal for every single person in Canva and then attach it and send it—blessed bee, blessed bee. Now I can literally send a proposal while I’m still on a discovery call and they can book within 10 minutes.”
More revenue: By adding strategic upsells (like behind-the-scenes video), she’s booked multiple clients at higher rates.
Client praise: One client told her, “This experience has been so smooth—you should raise your prices.” Another screenshotted her emails as inspiration for their own business.
What I loved most is that it wasn’t about making me fit into someone else’s system.
I knew right away I wasn’t the person who could just buy a course and watch the steps on my own. I needed somebody to do it alongside me, to hold me accountable, and to light a fire under me to actually finish.
On our first call, Colie just asked me questions for like 45 minutes—‘What’s wrong? What do you need? Where are the pain points?’—and then she made a plan for us to do it together. That’s when I knew I was going to love working with her.
She’s so good at explaining things without being judgmental or rude, even when I felt totally clueless. And I loved that the system we built wasn’t some cookie-cutter thing—it fit my business and how my brain works.
I literally told people I made my investment back with two proposals. Since then, I’ve sent more than a dozen. Everything after that has just been growth.
The best part—and why I tell everybody Colie is the GOAT—is the support. You can send her a problem and a lot of times within an hour, sometimes within minutes, you’ll have a response. And that is key because all of us in business know if I’m trying to send a proposal to book a client, I need that answer.
She also made Loom videos I could save and rewatch. I literally put one in my email as ‘How to send a proposal, stupid’—so when I forget, I just search that phrase and pull it up.
I needed the ability to work with her for a couple of months, but also to have a fire lit under me. I booked calls every week—she was my bff whether she wanted to be or not. That’s the process I needed: someone to do it alongside me.
And she never made me feel dumb. She’s so good at explaining stuff to someone who is clueless without being judgmental or rude. Plus, she anticipates your growth. Like I was attaching my pricing guide as a PDF, and she showed me how to make it a public link so I’d never have to update it in ten different places.
There was no gatekeeping. It was just an abundance of help, and I always felt like she was for me.
Absolutely. If you’re a creative telling yourself ‘I’m not a systems person,’ stop holding yourself back.
It’s not about losing your personal touch—it’s about making sure your clients actually experience the magic you’re already delivering. For me, Systems in Session was the best investment I made this year. It gave me time, ease, and the confidence to grow without panic.
I’ll keep singing Colie’s praises forever (and yes, I’m still waiting for my affiliate link!).
If you’re ready to stop duct-taping your systems together and start building your own luxury photography client experience in Dubsado, Systems in Session was made for you.
Mentioned in this Episode
Connect with Roxanne
Website: hawaimages.com
Instagram: instagram.com/hawaimages
LinkedIn: linkedin.com/in/roxanne-engstrom
Youtube: youtube.com/@roxanneengstrom-hawaimages