Often Ambitious: A Photography & Business Podcast
Often Ambitious is for photographers, creatives, and entrepreneurs who want to work less, make more, and build a business that actually supports their life, not one that runs it.
Hosted by business strategist Alora Rachelle, this show is grounded in lived experience. Alora built a six-figure wedding photography business while raising kids, then went on to help wedding photographers generate over $3 million in collective revenue through Wedding Atelier. She’s done the work, questioned the rules, and helped others stop overworking for underwhelming results.
Each episode cuts through the noise with conversations about profitable pricing, boundaries without apology, authority without hustle, and growth that leaves room for creativity, rest, and a life you don’t need a vacation from.
If you’re ambitious but done with burnout, performative busywork, and chasing success that costs you everything else, Often Ambitious is for you.
Often Ambitious: A Photography & Business Podcast
205. How Jenn booked $38k in weddings in just two months
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From Scientist to Full-Time Photographer: Jen's Inspiring Journey
In this episode, host Alora speaks with Jen, one of her recent alumni, about her rapid and impressive success in transforming her side hustle into a fully-fledged photography business. Jen shares her experience of booking weddings, raising her prices, and making the leap from a corporate pharmaceutical chemist to a full-time creative photographer.
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Welcome or welcome back to the podcast today. I'm so excited. I have one of my newest alumni with me on, and I literally dmd her and sent her emails. I'm like, I need you on the podcast, because her win was well, it was fast, and I just want people to know that this kind of result is possible, and it just shows that if you just put in the work or just back it up with a little delusional mindset, you can actually book your highest package or book. Your new prices. So Jen, welcome to the podcast. I'm so excited to have you here.
Jennifer KahlThank you so much. I'm so honored to be here.
AloraYay. It's so funny'cause you've been listening for the past month and you're already on here.
Jennifer Kahlit's a little crazy. I got the emails at first and I was like, that's not real. That's just automated. And then you slid in my dms. I was like, oh no. Like he actually wants to talk to me.
AloraI was like, Jen, I love you. I need you in the podcast. Thank you. Okay, so I kind of want to walk through before we get into like your, an insane win about what your journey looked like in photography before joining and I know that last year you made six figures, but it was kind of at the cost of booking so many weddings. Could you walk us through your photography story and journey?
Jennifer Kahl2024 was my first real in photography. Like I booked my very, very first wedding from somebody that didn't know me. The end of December of 2023 and then 2024 was just crazy of booking lot for both 2024 and 2025. I was in that lake. 2K to 3,500 range. And every couple of bookings, I was like, well, I guess I gotta raise it two to$300, It wasn't until January of this past year where I booked. I said, whatever, we're gonna put my highest package at 5,500. We'll see if anything bites. And then I booked it. And I booked it again. And I booked it again and I was like I need to do something about this. And right around that time I had found the podcast and I was listening and you made me laugh within like the first five minutes of listening. I was like, okay, we're here. I reached out and then you voice memoed me, asked my pricing, and I told you, and you were like, yep. make that your top package So I did that. yeah, and I think I completely bypass your question and just went right to the meat of it and I'm so
AloraYes, So like the journey of like what you're,'cause like last year you said You made six figures. But what made you want to like join the program? Is it'cause you were burned out on the way to burnout, or did you just want direction? Like what did that look like?
Jennifer KahlYeah, so I am trying to go full-time. I still have my full-time job.
AloraHmm.
Jennifer Kahland I wanted to not do 25 to 30 weddings. And then I'm also in like the Philly suburbs, so I was trying to get into the higher end market in the area.
AloraYeah. And I remember when we got on our call together you know your area is higher end.
Jennifer KahlYeah.
AloraI mean, most people struggle with the mindset part of raising their prices, but for you, you're just like, I. Whatever. How did you, how do you get in that mindset of like, let me just book it and they will come kind of deal? Or is it just come natural to you?
Jennifer KahlIt's definitely been a year long journey of just consuming education content of, a bunch of people telling you you can do it.
AloraMm-hmm.
Jennifer Kahlmany people can't be wrong. that many people can't know more than I do or know less than I know, and that I, my threshold is just lower at that point. So I figured why not trust it, try it and over a year of why not try it and it continuing to show up is just really what's gotten me to that point.
AloraSo when we got on the call and I repositioned your prices, made them more appealing. Were you just like, let's do it? Or was there any setbacks? No.
Jennifer Kahlyou slid in my dms and I said, okay. If she says so yeah, like the worst case scenario is somebody doesn't book it
AloraMm-hmm.
Jennifer Kahlagain, and then I just readjust.
AloraMm. So you just naturally have a strong mindset. You're like, let's just try it and see what happens.
Jennifer KahlYeah.
Alorayeah. I love it.
Jennifer Kahlof f around and find out
AloraYeah.
Jennifer Kahlway than maybe Philly intends it.
AloraMaybe, are you guys like more gritty over there? Just kind of like,
Jennifer Kahllike, I'm not proper. So yeah.
AloraLet's go even further. So this last year was your first year full time. So how did you get into photography and what inspired you to kind of pick up your camera and decide to, I don't know, be a business owner?
Jennifer KahlYeah. So I was doing photography, like I took a photo of my brother and his girlfriend in like 1998 and they were just so freaking happy when they saw the picture. And 8-year-old me was like, They're happy. I'm happy. I like this. And then I got a camera again in like high school, whatever. And then I was going through college my degree's in molecular bio and my mom was like, you're gonna be a doctor. And I said, no, I'm not gonna be an artist. So I changed my degree to film photography, like a fine arts situation there. then the 2000. Nine, 10 recession. happened, and I was like, nobody's gonna pay for art. I need to finish my science degree and go to the sciences that's gonna like pay me. So that whole time I was still doing photography, but then my camera broke, off to the wayside. So I took a 10 year corporate break and in 20 23, 1 of my very best friends was eloping in California and was on a budget. And she said, will you mind taking my photos? I said, I haven't touched the camera in a decade. Are you sure? crazy. No guarantee of what you're getting here. I didn't even have a camera again at that point. Like my camera had broken. It was just off to the wayside. A friend of mine said, just rent one, like it's not a big deal. So I rented a camera, flew out to California and I was holding the camera and like they were saying their vows. And I just started crying and I was like, this is it. this is what it is about. I came home from that trip and I told my husband like, buckle up. I'm starting a business. so that was June of 2023 and then I just dove all in.
AloraOh my gosh. Oh, that was like two years ago. Oh my goodness. So are you in your bio career right now and trying to like figure out a way? Okay, gotcha.
Jennifer Kahltitle is currently Pharmaceutical Chemist.
AloraMm.
Jennifer Kahltrying to snake my way outta there.
AloraI love that. My uncle is one too. I don't know anything about it, but yeah, I was like, you guys work with chemicals? Cool.
Jennifer KahlWhat do For work their best?
AloraThat is really interesting to me how you have such of like, I don't know like a science-based background, but also like you knew you were gonna be a creative or at least you knew you wanted to be. That is so interesting. I feel like a lot of people usually pick one or the other or think, oh, if you're a creative, you have to look like this or dress like this or act like this. How did you know you were a creative? I'm just curious.
Jennifer KahlHonestly, my friends at this point laugh at me because I've spent the last 15 years of my life saying I'm not creative at all. I don't have any creativity whatsoever. and I just recently designed my sister's baby shower invites and my friend was like, oh,
AloraMm-hmm.
Jennifer Kahlthought you weren't creative? So it's been a realization probably within the last like three months that, oh, shoot. I, like, I am creative. I very much lived in the analytical side of my brain for the last 15 years.
AloraI love that so much. I mean, my husband is very analytical. He's an engineer, but he is a musician, so he's always singing, playing music or doing something of that nature. And he likes to design Instagram grids just for fun. I'm like, I think everybody can do something creative.
Jennifer KahlYeah, no,
Alorafor fun. Okay, so back into the pricing. walk me through the journey again because we just, we went over like the data. I have like a post-it note. So did you apply for the program? Like how did we get in contact with each other? I don't even remember, even though it was like two months ago.
Jennifer KahlSo I was again, stalking the podcast. And I think one of the February episodes was like, wedding CEO O is open. And I was like, oh, lemme check this out. So I stalked the website, read every word that you have on there. I was like, I like this. This seems legit. I applied and then. You sent the course through email and I watched that and then you DMed me the next morning. I think it was literally like 6:00 AM and I was sitting there watching the course. Like, okay, this makes sense. Yeah, and the fact that you provided feedback right away after a couple of questions really just hooked me of yeah, like we're doing this.
AloraI love how just straight and to the point you are. I mean, we agree on this very no nonsense, no fluff. You're like, Nope, seems legit.
Jennifer KahlYeah.
AloraI'm trying to remember, I should have listened to the, my voice message verbatim, but I think I said like, Hey, what are you working on? Or what do you want? Like, what do you want to do? And you're like, I wanna raise my prices. And I think you told me your existing prices and I said you probably should do X, Y, and Z. And you're like, okay, cool, I'm joining.
Jennifer KahlOkay. more The Spark Notes version
Alorano, that's like I think that's actually the version. So. Then after that, right. Okay. I'm trying, I'm collecting, it's 10:00 AM here in Michigan and my brain doesn't wake up till noon. So after that we got on a call, right? A one-on-one, our one-on-one intensive, and then we completely restructured it based on how many weddings you wanted to book, what clientele. I think I gave you action step plan.
Jennifer Kahlyes.
AloraNext action steps. Did you raise your prices?'cause you said you had an inquiry sitting in your inbox,
Jennifer KahlYep.
Aloraokay?
Jennifer KahlYep. I raised my prices first and then I went back to the brand story
AloraMm-hmm.
Jennifer KahlI knew who I wanted to attract
AloraMm-hmm.
Jennifer Kahlmy ideal client was and like I was providing, but I didn't know how to communicate that. so I went through that quickly. And then just started to make some tweaks on my website. but yeah, no, I had the inquiry sitting my inbox and I raised my prices and I said, Hey, just as a heads up, like my prices did increase. Lemme know if you have any questions. And then went on the call anyway, so I was like, okay. And yeah, they were, were talking about, what they were looking for coverage wise. oh, it also looked at the sales script. They were looking for coverage wise she mentioned that one of the photos she wanted was like a photo from her parents' wedding. Like,'cause they have the album. I was like, oh, like I have a collection that offers albums as well. Like if that's something that you'd be interested in. I have a parent album in there as well. and she was like, absolutely yes. So I literally had a tab open with the sales script of like, okay,
AloraYeah.
Jennifer Kahlokay.
AloraThey're like, wait, it works.
Jennifer KahlYeah. so it was a combo of like a lot of different things that I think I can sell. Like I know that I have that skill,
AloraMm-hmm.
Jennifer Kahlbut really like fine tuning of, I have this offer, how do I connect that with what they're looking for anyway?
AloraMm-hmm.
Jennifer Kahlso just getting to know them and walking through that.
AloraAnd so what package did they end up booking?
Jennifer KahlMy all-inclusive collection, literally everything in the kitchen sink like you described. That was seven K,
AloraYes. And so when we were DMing, was 5K your highest package then? I'm trying to remember.
Jennifer KahlYeah.
AloraReally? So you raised it like$2,000 and they didn't even flinch.
Jennifer KahlYeah,
Aloraand then you put it in the Slack channel, right? A couple of days later you're like, Hey, so this thing works.
Jennifer Kahlyeah, yeah, it was, I got off the call with my husband and I was like, there's no way. And then maybe like 20 minutes later you get the little HoneyBook notification of like, blah, blah, blah, has signed contract. I was like, no way. That's not real. so yes, I live in a constant state of delusion during the call, and then the call ends. I'm like, that's not happening. There's no way. That's never gonna happen.
AloraOh my gosh,
Jennifer Kahla combo of like just sliding in and out of each mindset.
Aloragirl, that is crazy you already made your investment back
Jennifer KahlYeah.
Aloraover 2K over your investment.
Jennifer Kahlwas the first one and I've booked two more since. So
AloraShut up. What? Okay.
Jennifer Kahlnot at the seven K, but like what I was previously charging for the two weekend or for like the full weekend.
AloraYep,
Jennifer Kahlother people booked at that price for 10 hours. Two photographers. Yeah.
AloraOkay. With these projections, like I, I need to calm down. Okay. My green juice is sitting right here. I mean, do you think if things keep going at this, speed and this level, and we're gonna have to keep working on your prices eventually if you keep booking your highest, but do you think you'll be able to probably leave your full-time job at the end of this year or maybe next year?
Jennifer KahlOh yeah, no, I'm leaving in July.
Alorawhat?
Jennifer KahlYeah. Between what I have previously booked for 2025 and then, like told myself that if I booked 10 weddings before April 1st that I would quit. And I still told myself that in the beginning of February I had six at that point. and I missed my goal by one day. My 10th contract signed April 2nd. Yeah, I told my husband, I was like, I'm a little annoyed, honestly, that it was April 2nd, but that's just the
AloraYou're so crazy.
Jennifer KahlI know.
AloraI'm still successful.
Jennifer KahlSo April or July I'm heading out.
AloraWow. Jen, I didn't know this before we got on. See, this is why I had to DM you because I didn't know this.
Jennifer KahlYeah, I am
AloraI'm wigging out honestly. Excuse me. So how many weddings then have you booked since February? Since joining?
Jennifer KahlI think five.
AloraWow,
Jennifer KahlYeah.
AloraApril. Yeah. Okay. That's normal. Yeah. No, everybody does this. I just love how Bulletproof like Jen is just like. Success is what we do here. Okay. Well, I know you're still, you've only been here for two months and you're going through everything, but what would you say are your favorite tools have been since joining the program. Do you feel like your mindset about money has changed? I mean, I know you were already kind of like, let's do it, but I'm just curious.
Jennifer KahlYeah, so the pricing calculator really helped me out because
AloraMm.
Jennifer Kahlgenuinely, just I started, I said, I don't know,$2,000 seems legit, right? Fine. Somebody will pay it. And then I was just darts to a board hoping that something stuck.
AloraHmm.
Jennifer KahlSo when the conversation of like going full-time really started to take root as a possibility the pricing calculator was just top-notch with being able to input all of my expenses and then having to be like, this is what you should be charging minimum. And I was like, oh, right, I need to be saving money. 4 0 1 Ks are on fire right now, but like, I need to be saving
AloraYeah.
Jennifer KahlSo the fact that that was all included as something to consider was just. Top notch for me, and I'm a numbers person, so that really helped. My spreadsheets have spreadsheets. And then with the mindset, the, the chat, GPT
AloraYeah.
Jennifer KahlI just sat there for like 15 minutes. I was like, I dunno how to make money. Because I know that's not true, but I was just like, I feel like that's what I'm feeling right now. So those were the two that were the most immediate, like, okay, here is something that's like tangible that like is going to immediately help. And then the brand story was very helpful as well.
AloraYeah, I'm glad that you liked Chatty B, but he's about to change actually'cause we're making a girly and she's gonna be your mindset and marketing girl. But that is so funny. I love that you used that. I thought it was cool. I was like, you can just, it's like your free pricing therapy, buddy. You just be like, this sucks right now, and be like, no, you got this. You're okay.
Jennifer KahlI have a post-it our kitchen, like our command center of like what I wanted to. Do for 20, like full-time, 20, 25,
AloraMm.
Jennifer Kahltheir mindset questions of like, am I good enough? Do I know how to run a business? What if I fail? and then like the other side of the Post-It note is, this is the dream, this is joy in your work. So I just kind of flip flopping between those two and then having chat GPT confirm what I'm
AloraYes,
Jennifer KahlYeah.
AloraI love it. Oh, that's great. And then I think even though you have the mindset and then the pricing and the data to back it up, You knew that the sales script, you could just follow something and not go blank. What did you feel like you did before when you got couples on a call? Because of course they booked, right?'cause you were overbooked last year. But what do you feel like has changed in like your sales confidence?
Jennifer Kahlthe authority. Very much. I was asking a lot of questions and then it was a lot of like. Tell me about your day. Do you have this? Do you have this? and then here's what I do.
AloraMm-hmm.
Jennifer Kahllike mesh. but with the sales script, figuring out and being able to address that.
AloraMm-hmm.
Jennifer KahlI had a couple that she was like, I am so petrified of the day becoming a photo shoot. She's like, I was in a wedding as a bridesmaid and all we did was take photos and I just do not want that to be my day. So it really like opened the door that, that's not my style anyway. But to really address that concern for her. And that was another, like sent the contract. They signed same day.
AloraWow.
Jennifer KahlYeah.
AloraYeah. I mean that's so much deeper than being like, Hey, what do you want? Oh, that's funny. That's what I do. What's your budget? Oh, that's what I charge. Being, actually no, I'm the professional. Like I know exactly like this is, this is what you're gonna get is what you're not gonna get. Like I love that. Yeah. Being able to have that authority is so good. Okay, so I don't even know, two months, five weddings, I'm still. I mean, did you figure out like how much that was for the past two months, like the revenue? Did you calculate that yet?
Jennifer KahlIt's a little over 30 k.
AloraLike,
Jennifer KahlI feel like this is gonna be one of those episodes where the internet hates me. But I swear you can do it too.
Aloralisten,
Jennifer Kahlup. You'll
Alorayou. You can though, because your highest package was 5K and you're like, I wanna get to seven K. Well, you already did that, so now we gotta have another goal. Right. In just one call in just seven days, you know, you could make 30 K in two months. Yeah, totally. Okay. Is there advice for somebody in a similar position like you, because I know you were on the road to burnout, but then you're like, I wanna make this full-time. I don't wanna feel like this. Like what would you have to say to somebody that's really on the fence about like, joining a program like this?'cause I know there's a lot of programs that don't deliver and there's, you know, a lot of fluff out there.
Jennifer KahlTrust your gut with like, if you think something is a good idea versus not. And I know that sounds silly when people are really conflicted, but like I'm a firm believer that if you sit there a minute and just really think about it, you know which way you wanna go,
AloraMm-hmm.
Jennifer KahlAnd do it scared, and to your point, delusion it really just, it takes you so far you believe in yourself and it sounds so woo woo, but if it isn't the truth, it's like nuts. That really is what it is. I have a vision board literally right next to me and says, be brave enough to be bad at something new and. is just like my mantra in it. So yeah, do it scared, try it believe that you are capable of putting in the work and getting your re your, like your reward for that.
AloraJen, that is so good. Your mindset's already good. You sharing my mindset episode yesterday, I'm like, Jen doesn't even need it. Like, what do you mean?
Jennifer KahlNo, but it was so good. I forget what you said. Shoot. That I was like, oh my God. Yeah. That is it.'cause again, like I told you, there are some moments where I'm just like, yeah, know what I'm doing.
AloraMm-hmm.
Jennifer Kahlgot it. And then other moments where I'm sitting on the couch crying, holding my dog, like, I'm never gonna be able to feed you again if I quit. So yeah, just
AloraYeah.
Jennifer Kahlsentence to replay because it's so true. Like you got it.
AloraYou got it. I think that's why we need mindset pep talks every once in a while to kind of like get you out of that hamster wheel of like, everything's great, everything's horrible. What are we going to do? I haven't had an inquiry in 60 minutes and just be like, oh, it, it's been 60 minutes. You know what I mean? Like that reality check. In terms of mindset, do you feel like having those like vision boards and Post-Its and stuff like keeps you on track? Like how do you self-Correct. At least how have you done it up to this point? I'm curious.
Jennifer KahlYeah. Quite like a formal journal, but like a visual of some sort of literally anything we had the mindset challenge, 11 days, and one of the prompts was write a letter to yourself years from now. So I just brain dumped into that and then I scheduled Gmail to send it to me next year.
AloraOh, I love that.
Jennifer Kahlone of those that like pausing. Think about where you were last year, if you would've told 20. 20 me that this was even where I would be, I would've laughed at you said, dream big. Okay, you're a
AloraYeah.
Jennifer KahlYou're not creative, you don't take photos. not anymore.
AloraWow.
Jennifer KahlThat was a 19-year-old dream. But yeah, just really reflecting on how far I've come, keeps me grounded.
AloraYeah. I think even looking back to that whole journey of like, you are a scientist, you're not a creative, like how does it feel to know that you've created something out of nothing and now you're turning it into a business where you can fund your creative life?
Jennifer KahlYou're gonna make me cry. I'm so proud. I don't verbalize it a lot because I start to do this. But I am really, really, really, really proud, creating something from nothing. And the grinds that the last year and a half has been.
AloraYeah.
Jennifer Kahlit's legit.
AloraI just feel like for that mindset challenge we should have did one, like write a letter to your 5-year-old or 8-year-old self because like.
Jennifer KahlI would just cry through the whole thing.
AloraI can't even see the paper, but it's, it's just like so fulfilling to know that you can get paid to capture wedding days. You can get paid to be creative and it's so fulfilling'cause you're passionate about it. Something you love to do, you feel like it's your life's work. I just, I think that's so inspiring, Jen I'm flabbergasted that you did this in two months and I am so proud that you can leave your job in July. Do you have any lingering advice for people who wanna do the same thing or who also think they're not creative or that they couldn't build a business like you have done?
Jennifer KahlYeah. No, like it stays true. Just do it, like do it scared.
AloraHmm.
Jennifer Kahlbe scared out of your mind, but you gotta do it. You gotta try. You have to at least try.
AloraYou have to at least try. I like that. And you just, you don't know what's gonna happen. Maybe just stop trying to predict what's gonna happen all the time.
Jennifer KahlOh God. Yeah. Recovery, let's say recovering, still very much a perfectionist.
AloraMm-hmm.
Jennifer Kahlthere's a lot of things that I hadn't started, like getting my face on Instagram was petrifying and I just would not do it. and then I Snapchat my group of friends literally every day, like a morning update. And I was like, wait a minute, this is the same thing. And all of a sudden you see my face on Instagram. So yeah.
AloraYeah, just those little baby steps. Just try. You never know what's gonna happen. I think that gives us the drama is like having to always be like, oh, what's gonna happen? And like looking into the future instead of just taking that first step and realizing, oh, it might not end up what we've,
Jennifer Kahlyes. And you said it. Um, Watching that closely.
Aloranobody cares.
Jennifer Kahlnobody cares. And I actually bought a sticker from my laptop that says I am cringe, but I am free. And it's a
AloraYes.
Jennifer KahlIt's a little dog running through a field. And that's really like, yeah. So what if I'm
AloraYes.
Jennifer KahlOkay. It's me and my
AloraAs another millennial, I approve. We get made fun of so much. We're having emojis for living our life LOLs after our text messages.
Jennifer KahlMy gosh. Yeah.
AloraI feel like you're just stepping into this like new version of yourself and I think when you leave your job. you're gonna be even more bold and confident, and I just think you're gonna be so unabashed and I cannot wait to see it. I'm gonna have you back on. I already know you're coming back, but thank you so much, Jen, for coming on the podcast and sharing your story, and I just think it's inspiring because, well, it's only been two months, but also there's so much you can do in so little time if you just do it scared.
Jennifer KahlYeah,
Aloralove it.
Jennifer Kahlfor sure.
AloraThanks for coming on and everybody else. I will see you in next week's episode. Bye.