Ep 118. Learning to Believe in Yourself with Hannah & Ryan Donaldson

I'm Ashley!

My mission at The Purpose Gathering is to help driven momtogs like you level up, so you can build a sustainable business AND a fulfilling family life. I do that through authentic brand photography for mompreneurs and my signature program for mom photographers: Side Hustler to CEO.

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Today, I have the absolute pleasure of interviewing one of my students from the Side Hustler to CEO program, Hannah Donaldson and her supportive husband Ryan Donaldson.

Hannah and Ryan have been happily married for 7 and a half years and are parents to two beautiful little girls and they all reside in Minnesota. Hannah is a photographer who specializes in photographing graduating seniors.

She shares her experience being in the coaching program and how it totally transformed her photography business.  

Ashley: So Hannah, let’s go back to the beginning. Take us back and talk to me about how you got started in your business and what it looked like then.

Hannah: Yeah, so I was doing a video production program in 2015 and fell in love with all the photography related courses that I had to take for that program and just kind of realized like maybe this is something I could do. I kind of initially expected it to be something I did on the side just like as a little side thing, while I was finishing up my schooling. But after initially thinking that, kind of fell in love with it more and decided to just go full on into it, with a little bit of encouragement from Ryan.

Because I had a lot of roadblocks, like mental blocks of, could I really do that?

It’s so saturated.

Everybody who has a camera does a business, maybe I shouldn’t.

And he really encouraged me to take that step and dive in. So that’s kind of how that started.

Ashley: I love that. Do you remember your first paying client?

Hannah: Yes, actually. It was that mom with the two little kids, or three little kids and I think I charged $25.

Ashley: Oh my gosh, I love that! I think my first session was like 50 bucks and like I still remember to this day like that feeling of actually starting a business. You exchanged money for a service that you started and it’s so weird, right? Like when you just get started and I love that story of how you got started with video production but then actually just fell in love with the photography. I think that’s so funny. I love that. Okay, so Ryan, from your perspective, I’d love to know like what you’ve noticed, what has stood out to you as Hannah has grown her business over all those years?

Ryan: Yeah, so as Hannah mentioned, I kind of pushed her in that direction and the reasoning behind that was really simple. I saw her practicing a little bit and I realized that she had a natural talent for it.

Then the most amazing thing for me over the years has been watching that talent meet more and more skill as she gets better and better every year. It’s been amazing to watch her grow.

Ashley: I love that. That’s so sweet. But prior to meeting me Hannah, because that’s how we met was through the podcast and later you invested in the Side Hustler to CEO program. Had you ever invested in any other business education, like leading up to that point?

Hannah: No. aside like what I said, the classes that I took, that was mainly like skill related though in photography, not business and so I really had no clue what I was doing. Before doing the program I just was kind of winging it, which I think is what a lot of people do when they start a business and just kind of learning as I go, which is a lot of trial and error. So yeah, I didn’t do anything prior to that.

Ashley: So, what do you think it was about working with me or meeting me that kind of pushed you into that idea of wanting to do the Side Hustler to CEO program? Like what stood out to you about it? What kind of made you pull the trigger so to speak?

Hannah: I think it was relating to you and knowing that you’re a mom too and I kind of binged your podcasts and was like wow! I really connect with this girl, I really resonated with a lot of what you said and trusted you and trusted that through your years of experience having a photography business and then also walking the shoes of like being a parent too. And I just knew that it would be a good fit and I felt confident in the things that you wanted to teach in there and excited about it too.

Ashley: That’s awesome. So, I remember that when we first connected, I think it was through Instagram DMs` or maybe it was at the Hangout that we did. It was one of those.

Hannah: Yeah, it was that. It was the Hangout.

Ashley: So, I had promoted that I was doing a hangout which was on Zoom and we are going to be talking about a certain topic. I can’t remember what it was, but then I think after we connected and you had found me through someone else’s podcast, listened to the podcast. So, I remember this friendship evolving out of like two weeks I think from when you heard about me to when you were like I’m considering this program. So, I think that’s really cool too because there was an instant connection for both of us I feel like.

And that is definitely I think important when you’re working with someone to know, like and trust them.

But I think it’s so cool how quickly you were able to do that. So, tell me like is there anything specific that you remember or was it just an overall feeling? Or can you remember like a specific episode that you were listening to? Because I feel like that’s pretty quick to go from just meeting someone to being like, Wow! I really resonate and trust her. Can you elaborate on that a little bit maybe?

Hannah: I can’t remember a specific podcast episode necessarily. But I think I just really related to you. I think that you’re really vulnerable in your podcast and very like real and you don’t have like a lot of fluff. And I don’t know.

There’s a lot of podcasts that I feel like are just kind of time consuming, but with yours, I feel like I always took something away from every episode.

And I was like, if I’m getting value from like these, like there’s got to be a lot of good stuff in that program. I don’t know if that really answers that question, I can’t remember the exact episode that made me like, okay, I really want to do this. I think it was just a lot of good takeaways that I got.

Ashley: That’s awesome. Well good. Thank you. I’m so glad that you enjoy the podcast and that is something that I really try to do with every episode is have a reason why I’m doing it. I just don’t want to get in front of the mic and just talk. I really want to teach and make sure that you get something tangible and I’m all about taking action. Would you agree? Like there’s no sitting on the couch listening to the episode, there’s like lots of action. Because I really do believe if you want to make a change in your business, in your personal life, like in anything in general, you have to do something different than you’ve always done. And so, I’m really big about taking action. So, Ryan, from your perspective, I would love to know what did the conversation look like when she brought up the Side Hustler to CEO opportunity?

Ryan: Yeah, it was actually really interesting timing because Hannah had actually elected to support me in a similar training program, but for something completely different. And you know, like I had mentioned earlier, you know I recognized that she had the raw talent and as the years have gone by, she’s picked up more and more skill. But I also recognize that business is one of those things that you don’t just necessarily have a raw talent for.

And so, I recognized that that was something that would really benefit her in her business as she had this deep desire to take it to the next level.

So as soon as she approached me with it and mentioned all of the things that she had already gotten out of listening to your podcast, I was sold pretty much immediately.

Ashley: I love that. That is so cool. So, Ryan kind of convinced you that you were worth taking a chance on, is that right?

Hannah: Yeah, because I think while I definitely wanted to do it when I like saw the price tag, I knew it was 100% worth that amount. But wasn’t certain if my business was worth that investment, if that makes sense. I think it was just another mental block of like, am I really worth like spending that much money on my business? Who do I think I am to like think that I could be at that level to be in a program like that kind of thing. Which is really sad to think about now that I was thinking that way. But I think that was something that we talked about too when I brought it up was should I do it? What if I don’t succeed still or like things like that. Just a lot of my own mental roadblocks that I think a lot of people deal with when they’re newer or because I had such a long gap between when I started to when I like kind of got back into it and got more serious about it again.

I was just kind of stuck and needed a little push again from Ryan.

Ashley: Yes. So, what did that conversation look like Ryan, when she was telling you that what if I don’t succeed? Like what was your thought process of like what would happen if you tried this and it didn’t work out? Like did you guys have that conversation?

Ryan: I don’t really know if we did.

Hannah: So those were like private thoughts that she was having that maybe she didn’t like share because she was like, I think a lot of us do that.

Ryan: I’m sure that we talked about it. But it never really crossed my mind as a possibility or a concern, because like I said, I trust her and I knew that she had what it takes. I knew that all it was going to really take for her to get to where she wanted to be was to put in the effort and to have some support.

Ashley: I love that. Don’t we all wish we had a Ryan just like in our back pocket being like, you can do this! It is so important to have a support system and people who really rally for you and get what you’re going through. But to speak to all those mamas that might be out there and not have that support, that was me. My husband is very supportive but he’s also very skeptical. He’s the kind of guy that’s like, tell me how this is going to pan out, what’s the return on investment here? And so, it was a lot of me at the beginning when I was investing in my own business, telling him I’m worth it. I can do this, like trust me.

And so, if you’re listening and you don’t have a spouse like Ryan who is supportive and rallying for you, know that you don’t need that necessarily.

That your belief in yourself is enough and your family and your spouse, they will get on board eventually. And my husband did. He saw that when I was very passionate about what I wanted. That I would go after it and that even if I invested in something that didn’t maybe turn out the exact way that I wanted, I always found something in that for me to take away and say maybe that investment wasn’t the right investment at that time, but here’s what I learned during that time period. There have been a lot of times in my own business that I’ve done things that I think I did too soon, maybe should have done that a little bit later. But now that I did that I have so much more insight to make better decisions next time. So, I think that’s really important to know as well when you’re making an investment is that there is always something to be learned and you’re always growing in whatever area you’re investing in.

Hannah: Absolutely.

Ashley: So, Hannah, what would you say are the biggest differences that you noticed in your business while going through the Side Hustler to CEO and then maybe after?

Because I know that you had some pretty big aha moments like right away. Like starting the program, I remember like week two to four you were already seeing some significant changes. So go ahead and just tell us kind of like what you felt as you were in the program and then maybe after as well.

Hannah: I think the biggest thing I noticed right off the bat was it was my first sense of community in the photography space.

It was so nice to just talk photography and talk business and all these things and to feel like okay, I’m not alone in this.

Like we’re all working on our goals together side by side.

It was really cool to see that. And then the other big thing that I noticed right off the bat was like confidence that it gave me and knowing that I can do this and it’s possible. The taxes and all the like little nitty gritty business things that can be kind of daunting and confusing at first are not that hard and I can learn it and it is possible. And I think it was possible because of how like bite sized the information that you gave out to us was. It was definitely not overwhelming in any way and super helpful to just boost my confidence. It wasn’t like I started the program and was overwhelmed like can I really do this?

Ashley: Absolutely. And I think that’s what’s really unique about this program is that I’ve designed it to be specifically for moms who are busy. You already are juggling so much and so trying to cram a ton of information is not going to do you any good. I’ve spaced it out strategically so that you have built in implementation time, so that you could ask questions, you could do the work, you could space it out so that you weren’t feeling behind. Because I’ve been in programs and courses before where the information is so stacked that you feel so behind and when you’re in a guided program like this you don’t want to feel behind because then you just have way more work to do to catch up. So, I’m glad that that was bite sized enough for you and that is awesome to hear. I’m trying to remember back to, I think it was like one month into the program.

I think I remember it was like week four we were on a coaching call and you told me that you basically booked enough business in those four weeks to pay for the program. Can you tell us a little bit about that?

Hannah: Yes. So, it’s just so funny that like probably the biggest roadblock that I needed to like get the okay from Ryan to do was the financial aspect. And then it like ended up being the program that helped me be able to even make that amount of money in my business, which I had never before that in that short amount of time. And so that was just crazy and amazing! I remember messaging you about that and being like, well it was definitely worth the investment because it already paid off so.

Ashley: And that’s so cool that you saw those results so quickly. And I feel like I can take a little credit, but honestly if you come into any education program and you are not willing to do the work, you won’t see the results. And I think that happens with so many people is that they get really excited about things but then they don’t take the action. It really does take the right person to be in the program for it to work. And I saw you show up at every call, you rearranged schedules, you had a baby on your hip. I mean you were there and you prioritized the time to get the most out of this program, which is incredible! And that’s why you have seen such incredible results Hannah, because you did the work. I just gave you a little bit of guidance like Ryan said at the beginning, but it really takes you being the one to step into that role to that CEO role and own it and do the work. So, kudos to you Hannah. I’m so proud of that.

So, tell us a little bit too about like what did it look like to finish through the program? Are there any other big things that you can remember while you were in the program, aside from the confidence and then paying for the program within just one month. What were some of those other things that you noticed?

Hannah: I think your attention to detail with talking one on one with me, like if we had a little extra time at the end of a meeting, you were so accommodating to me. I remember coming to you about pricing and feeling like, would you mind looking at my website and seeing like, do you really think I should raise my prices? Like are people really going to buy that?

And I just remember you saying something that completely blew my mind and it was just because it’s something that you wouldn’t purchase, doesn’t mean that someone else won’t kind of thing.

And I just thought that that was amazing because it’s true and I just didn’t know who my ideal client was at the time. I didn’t even know that that was a thing before your program, like the idea of knowing who your ideal client is. Knowing how much it costs to do your business, how like all these little details that I totally would’ve been lost on before the program. Like I just think those are the little things, just talking with you one on one. Like it’s all the little details and the little things, the little extra 20, 30 minutes you took with me to go over things like that, that really have made a difference in my business and have really boosted my confidence. Having a seasoned photographer who’s been in the industry for like 10 plus years give me the confidence and saying like, you can do this and here’s what I think you should do and learning how to receive constructive criticism from you has been so helpful.

Ashley: I love that so much. And I think you touched on something really important too, and that is having a mentor point something out to you that maybe you just didn’t have the confidence to believe in yourself. I do remember having that conversation with you about how we tend to put our own person in our ideal person. We’re like, here’s me as the photographer and I’m my ideal person and if I wouldn’t pay that much then nobody’s going to pay that much.

We don’t really see outside of that possibility that there might be other people out there who are willing to pay more, who do value photography in that way and will spend that kind of money.

I am so glad that that resonated with you and that you took action and changed your pricing because again, I can’t change your pricing. I can only guide you and give you the recommendation. I’m never going to tell you what to do, but you are joining the program for guidance and so you took my recommendation and you raised your prices. Do you remember what the increase of your price was?

Hannah: Math. Hold on.

Ryan: Yeah, that would be like double.

Hannah: Yeah, I like doubled my prices.

Ashley: You doubled your prices?

I love that. Okay. Cause I remember like walking through this with you and I’m like, okay, so how much time do you spend? And like how many images that you do deliver and how long does it take you to edit all those images? And I’m like, how much are you making? Like I just remember all of these questions and we came down to like the take home pay. Do you remember around what that was?

Hannah: I want to say it was like $6.50 an hour, which is crazy.

Ashley: Yes, I remember that.  I remember going through the portion with you and specifically getting detailed on what exactly you were charging. We factored in all the things like your editing time, your client communication time, how long it took you to acquire that client, obviously not in that order. Then most recently you were telling me, and maybe this happened during the program too.

But you mentioned to me that since that conversation you have quadrupled your take home pay and now your take home pay is around $25 an hour. Is that correct?

Hannah: Yes, that is.

Ashley: And when did that shift happen? Do you remember?

Hannah: So, I changed my pricing like right towards the end of my season last year and it’s just insane because I was so nervous to do it. I thought no one was going to book with me for this last season that I’m in right now of this year. And I doubled my bookings from last year. So last year I had five senior clients and this year, I booked 10.

Ashley: Oh my gosh! And your prices were double what they were?

Hannah: Right.

Ashley: Oh my gosh! Okay, so not only did you quadruple your take home pay, which is so important, but you doubled your revenue,

Hannah: Right.

Ashley: That’s awesome. So not even, yeah, you more than doubled it though because you doubled your revenue and then you doubled your bookings.

Hannah: Right, right.

Ashley: So, you quadrupled your take home pay and you quadrupled your revenue.

Hannah: Yeah, right.

Ashley: That is so awesome! Oh, my goodness! Okay, so Hannah, I want to know what encouragement would you give to other photographers right now, who are in the shoes that you were in when before you joined the Side Hustler to CEO program and they are doubting if they are worth investing in themselves?

Hannah: I would say first of all, you are 100% worth it. There definitely are a lot of photographers in many areas, but none of those other photographers are you and that’s really what makes the difference. You might just need a program like this to give you that confidence boost to know that the things that make you, you and the things that make you different are what set you apart and it could really just be what you need. That sense of community, that one on one guidance and recommendations that you can get from Ashley to just take your business to the next level.

Ashley: I love that you pointed out that they are uniquely them and there’s no other carbon copy of them. And it is so important to believe that you’re worth it because if you don’t, that lack of belief really does trickle down into your business and it really does change the vibe from your ideal clients and they can kind of sense that. They can sense that you’re not feeling confident and they can sense that you might change your pricing based on if they ask for a discount or not.

I can’t tell you how many photographers come to me saying everyone always asks for a discount and that could be the vibe that you’re sending is that you don’t feel as though you’re worth it.

I just think that’s so impactful that you are worth it and that you are the only person in your maybe industry that can offer the unique things that you bring to the table.

So, Ryan, do you have anything else that you want to add about this belief and maybe like give some encouragement to these mamas who maybe again, don’t have a spouse that is rooting for them like you are for Hannah?

Ryan: Yeah, absolutely. I guess the first thing that I would say is confidence is definitely not something that comes easy, but it can be faked. And I think that it’s a good thing to fake it until you make it. You know believe in yourself until other people start to believe in you.

Ashley: I love that so much because we all need a little encouragement, right. And if you can’t get it from someone else, be your own cheerleader. Encourage yourself, do what you need to do to feel that confidence boost. Maybe it’s just getting your friends together and taking some photos of them and sharing those and just a little step here and there in the right direction is going to help with that confidence. But if you don’t believe in yourself, it’s going to be really hard for those clients to believe in you. Thank you guys so much for being on the show today. This has been so incredible. I can’t wait to hear how the rest of your year goes and I can’t wait to see what happens for you in 2023.

Hannah: Thank you so much for having us.


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My mission is to help fellow momtogs (mama photographers!) experience success in business and in motherhood. As an Arizona brand photographer for mompreneurs, I’m passionate about capturing authentic images that show off my clients’ unique personalities so they can connect with their ideal clients. And as an online business coach for momtogs, I LIVE for helping mamas experience incredible transformations that help them build a business they love, without sacrificing their precious time with their littles.

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