Your First Client: What No One Tells You About Pricing, Boundaries & Confidence | EP 49

Landing your first client feels like crossing the finish line, until you realize it's actually the starting line.

You celebrate the "yes," hang up the phone, and then the questions hit: What do I do now? Am I charging enough? How much is too much? How do I keep this client happy without giving everything away?

In this conversation, we unpack what really happens after you land your first client. It's not a conversation about proposals or onboarding checklists, it's about the mindset shifts that come with getting paid for your work for the first time.

Drawing from our own experiences, we explore the habits that many new business owners fall into: overdelivering to prove their value, letting friendly relationships blur professional boundaries, and setting prices that become difficult to outgrow. These early decisions often shape the way you work long after that first project ends.

If you've ever struggled to balance great service with healthy boundaries or wondered why raising your rates feels so hard, this episode will help you understand where those patterns begin and how to break them.

What you'll hear in this episode:

• Why overdelivering is often driven by fear, not exceptional customer service.
• How friendly client relationships can quietly lead to blurred boundaries and scope creep.
• Why your first pricing decisions can have a lasting impact on your confidence and how to avoid getting stuck there.
• The mindset shift that matters most when you stop trying to earn permission and start building a sustainable business.

Ask yourself: 

What did your first client teach you that you're still unlearning today? And if you could go back, what advice would you give yourself?

Transcript

You're listening to Entrepreneur Encounter, the podcast where soft skills meet real talk for creative business owners who are building with purpose. I'm Dana, a Pinterest marketing strategist and agency owner helping wedding pros and creative entrepreneurs get seen without burning out. And I'm Sarah, a business and team strategist who helps small teams and podcasters communicate clearly, lead with empathy, and grow sustainably. Together we're unpacking the messy, meaningful side of entrepreneurship.

From boundaries to burnout, leadership to listening, so you can build a business that actually fits your life. You got your first client, you said yes on the call, and you did that little happy dance, right? Every time we get some some good news, like a new client, you're like, Yeah, this is awesome. And then 10 minutes later, a completely different feeling shows up. You ask yourself, wait, what do I do exactly?

So that mix the pure excitement right into a full like panic mode. And that's what we're starting today. Something happens that no one prepares you for. And that panic, you want to prove you're worth what they're paying. So you start saying yes to things you would never agree to. Now you over explain, you over deliver, you apologize for things that don't need apology. And it feels like you're just being a good business owner, going

Above and beyond building the relationship. But what's actually happening is quieter than that, and it's setting a precedent that will follow you for years. And this is something that I know I can say, and Sarah can attest that I have probably vented about this numerous times over the years. Is that setting that precedent that you are setting, like those confusing boundaries and everything? So today we're unpacking those hidden lessons that we have learned firsthand.

That your first client will teach you, and probably even your second, because you're still figuring it out. Not the ones about pricing spreadsheets or contracts, the ones about you, what you believe you're allowed to ask for, what you believe you're worth, and how fast those beliefs get locked in. If you're about to land your first client or you're still untangling the habits from the one you had years ago, stay tuned. We're covering three things.


The overcorrection trap, the way friendliness blurs the relationship, and the price tag that becomes almost impossible to move away from. But before we get into all of that, we want to take a quick pause to tell you about the spotlight swap. It's our audience exchange program connecting values-aligned entrepreneurs so you can grow in front of the right people, not just more people. If that sounds like something you want in on, the link's gonna be in the show notes for you.

Okay, so let's go back to that first client moment. You don't yet trust that you're allowed to hold a boundary. I've been there done that because you haven't proven anything yet in your own mind. So what do you do instead? You overcorrect. You respond to every email within the next hour, even at 9 p.m. You throw in extra revisions that nobody nobody's asked before. You apologize before you've even

done anything wrong. Sorry, quick question. Sorry to bother you again. But there's that shift, that reframe. That's not going above and beyond. That's fear that you may. So for example, when I was in the corporate world and going into the business world, I was afraid to have a day off. I was afraid to set the boundaries. I was afraid I felt like I had to respond to an email so quick because we don't know what that looks like for us yet.

No one's taught us. So because that behavior looks identical to good client service from the outside, it feels like fast replies, which in the corporate world is amazing. Extra effort, flexibility, these are all demands in any office setting. But the motivation underneath is completely different. Good client service comes from I want this to go well. Overcorrection comes from I need to prove I deserve to be here. Or

More personally, I need to prove I deserve your revenue again and again. And the client really can't tell the difference, only you can, and maybe not even fully that part either. Which is exactly why it's so easy to miss in the moment that you just think you're being thorough, but really there's an underlying fear there.


And that problem is what's teaching you that once you've responded at 9 p.m. one time because you feel like it's an emergency, that's now the standard that your client is going to expect every time moving forward. You didn't set an expectation on purpose. It just kind of happened because maybe you happened to be on your phone and the alert popped up. And you're like, let me just answer that real quick. But

It could be that you were also trying to prove something because this is your first client and your first time really stepping out on your own. So the first thing worth asking yourself with any new client, whether it's your first client or your tenth client, is is this coming from care or is this coming from needing to earn your seat at the table? that's right there. The heads home. Cause you know, when I st I remember starting with my first client, I thought I had to be on all the time.

Definitely not the case. That's why you started your own business so that you didn't have to feel like you were having to do all of that. So you can set your own boundaries and set your own rules. Here's something that makes a first client a little tricky. And a lot of the time that first client likes you, right? Like you get your client, and of course, they like you. That's why they wanted to bring you on. Not just for your work, but they for you. They're often someone in your circle or

A friend of a friend or someone you followed online before you even had your business. And they believed in you before you had to prove to them, which is great. But it also can blur a line that matters, the line between friend and client. And when that one's hard. Yeah, no, it definitely is. I remember I had one of my clients that I had, she would invite me to go out and like go out to dinner and like and I I didn't feel comfortable with that. In my head, I'm like, we're not really on.

I didn't believe that we were on that level. But I didn't want to blur that line and go hang out with her and then have to maybe because I was never in that situation before, but it was hard for me to determine if I wanted to or not. So that's where the lines get, you know, blurred. The expectations get fuzzy. Feedback gets harder to give and harder to receive. Then scope creep starts to sneak in because you're saying no to a friend.

Feels different than saying no to a client. So pulling from experience, I have a couple of clients because I don't give my number out to anyone. I don't care who you are, but I have had friends become clients who already have my number. Right. And so that's kind of where unexpectedly the scope creep will come in because they want to continue that. And while yes, I want to be friends with you, but I do have a hard time blurring that line. Like

I don't want to text you, hey, your stuff is ready. I wanna email it to you and then I need you to respond to my email just so it doesn't get lost. Does it always work? No. But we do our best because I we had to have more recently I have a client right now who was needing support and that's kind of where we were at with it of she wanted a quick text because she is constantly here and there and I had to tell her like I will not text you

I can't blur that line. I'll text you something fun about my kids or, you know, something about that. But like there has to be a distinction between how I communicate with you as a friend and how I communicate with you as my client and the content that I'm creating for you. Like I have lanes and they do not need to intersect. sure. It is easy. That's how you and I are. I'm thinking about this and like I notice I notice that too. Like we send our stuff about work and

you know, podcast and Slack or email. And then when we text, it's about us everything else. Yeah. You know what I mean? Like so and I th and I think that's a great boundary because again, like I rather it that way. I don't want to like it almost those like multiple personalities. Yeah, exactly. We will have two long running conversations at the same time from ti every so often, but it's about two completely different things.

One is always about the podcast and entrepreneurship. The only time for us to deviate out of that is if it's an emergency, like we need a response today, will we cross those lines? But typically we keep them in their own separate thing. And that's why, like, it's really easy to blur those lines and agree to extras like a quick call that turns into an hour or a favor outside of that original agreement. We've done it.

Well, not about the podcast, but for our own individual clients. We've done it. Yeah. Because at first, you know, it feels almost rude to hold a line with someone who took a chance on you. But that first yes becomes a template that is very difficult for you to change. And that's not for the client, it's for how you operate in your business. You're setting everything up for what's negotiable before you even know what you want your standard to be.

So it is very important for you to figure out what your standard is. What is your why? And usually that comes up to the why. Why are you in business for yourself? And this helps you from being cold with people who supported you early. It's about recognizing that the warmth of the relationship doesn't have to come at the cost of your clarity. Get clear on what it is. We have made jokes on this podcast numerous times. So go back and check on probably all the episodes. My laptop is an extension of my arm.

But I dream and covet and have gotten very clear that I don't wanna work all day. I don't want my laptop or my phone to constantly pull me away from the why, which for me is f time freedom and essentially freedom to spend time with my family or to go help a friend who's having a hard time and she needs help deep cleaning her closet because that's gonna help her get clear. Well, I wanna be able to go do that.

And not have the stress and overwhelm of all these looming deadlines. So clear is actually a kind thing that you can do not only for yourself, but your business, your clients. Fuzzy is where that resentment, those small yeses into something that you really don't want to do, or no, you don't have the capacity to do causes a lot of resentment later. Yeah. I've ended some professional relationships because

lines got fuzzy, lines got blurry and I wanted to be a part of something and I thought I was doing my part and it became more than what it should and I was asked to do certain things and I was like, no, I don't wanna do this. And then said person get got mad. You know, I'm not gonna go in like the full detail, but it's just like you try to build those relationships and then you go past your boundaries and then

Then you get stressed out and then it becomes this like never-ending cycle. And now you're trying to figure out how to get back from that. So, like Dana said, when you're building your business, set your expectations from the get-go so that it can help you in the long run. So let's talk about the numbers. Cause most people undercharge their first client. I know I did, definitely did. People talk about just go get the experience, just

Go get a testimonial, you know, just to go get your foot in the door. And in that moment, that feels smart, you know, low risk, maybe a reasonable trade, but that number becomes an anchor, not just for the client, but for you. It becomes the number in your head of what you're worth. It's incredibly hard to move away from that once it's there. I'm telling you right now, when I started my business, I was charging super low rates and it took me a long time.

To charge more because I thought that's where I should stay. Do you want to know what I charged for the first wedding that I ever did month of management for or day of coordination? It's what we called it way back when. What? How much? $250. Do you know what comes in a day of coordination or now a month of management? Yeah. That's tiny. That's

Just taking into the day of showing up, not any of the prep work leading up to it with building the timeline, coordinating with vendors, or any of that, you're looking at an eight to ten hour day. So I was making like twenty dollars an hour to do all of that. I reached the end of that day and it was a DIY wedding, so there was a lot of movement and there was not a big team.

I can promise you my next wedding was nowhere near $250. Like that wasn't even worth getting the experience. I love that wedding. I still remember that wedding. That couple was amazing. I loved the whole aesthetic and vibe. But $250 was not worth it on the experience side. It was not worth it to get a testimonial. I did get a five-star review from her, obviously. What else could I it was just not worth it. Never again will I do that.

Don't care if I'm new to the scene or not. No, exactly. And I think a lot of that stems from before we started a business. Okay. I used to work for a nonprofit and I was making $14 an hour. It's a nonprofit. I know that sounds like a low amount of money to be making hourly, but I'm I was, you know, in a nonprofit. And then after that, starting my own business, it took me a long time to figure out like how much did I charge? Do I charge $14 an hour?

But then I it like I had to learn like, you know, what's your overhead, your expenses, what do you want to pay for, your marketing? All of these things come into play as well. And yes, it's a back and forth thing. So I feel like one, then you end up justifying every price increase because you did start so low and going against that first number. So all in all, I think the identity or the common thread is

charging what you're worth requires believing you are worth it. So I didn't know what I didn't know, but I really quickly learned that the amount of time, attention, and detail and care that I put into my plans as a wedding planner, I was well worth more than that. Yeah, for sure. And if you don't believe that yet, no pricing strategy is going to fix that confidence level. You'll find a way to undercut yourself no matter what that spreadsheet says.

No matter what the industry standard says, you have to take a look in the mirror and say, I am worth this because I have done all of these things. So the question isn't really what should I charge my first client? It's what am I willing to believe about my own value before I have external proof of it? Because you're never gonna feel fully ready. Things are always gonna change.

It may be small changes, it could be big changes. You could do a whole rebrand or a whole service pivot. The proof comes after you charge like you mean it, not before. People need the things that you offer or provide. Charge your worth. Cause at the end of the day, unless you are a nonprofit, we're for profit. We have to be able to feed ourselves. We have to be able to support ourselves. And we have to be able to keep the business running. Every business has a baseline.

level of expenses from software to website hosting to marketing to whatever it is, you have to make enough money just to break even on that. But then you have to make money for a team or you have to make money to pay yourself. So here's the commonality running through all three of these. You know, the overcorrection, the blurred friendliness, the underpricing. Each one comes from the same place. It's the moment someone pays you you for your work, something shifts. You go from

you know, being a hobbyist or a helper and your own head to your professional because you are a professional. You have a business. You have things to get done. And that shift brings its own anxiety anxiety that nobody warns you about. I know when I started my business, I had nothing I I knew nothing. Nothing. I I didn't go to school for it. I learned on my own. I don't come from a line of entrepreneurs in my family to like talk to. And it was overwhelming.

When I started. And in in that anxiety, you start losing your voice. You start overexplaining your process. You know, you abandon the very approach that made your work good in the first place. All to prove you're legitimate. That's tough. And I know from my experience, I knew I was legitimate, but I felt like I had to prove people, like I know what I'm doing. But then learning and growing, I built that confidence over time and

I don't have to prove anything. Nobody, you shouldn't have to prove anything to nobody. To, you know, like, you know, as long as you're doing what you're supposed to do and, you know, setting those boundaries and doing your work, you know, and delivering what you're supposed to, like, I believe everything will follow suit. I do feel like it's important to point out that we do talk about boundaries a lot in the soft skilled niche. But boundaries do need to come first. It is in the boundaries and maintaining that clarity.

with your clients and your subcontractors and everyone else, yourself. Confidence follows when you stick to those boundaries. So you really need to you just have to be willing to be clear on those boundaries and stick with them before you feel ready to charge $2,000 a month or whatever it is. So if this one hit home, we hope that you will take a few minutes to grab our 20-minute clarity map.

In case you want to work through that to you and figure out what your boundaries are, the link to that is in the show notes. It's gonna help you get honest about where you're over-explaining or over-correcting before it becomes a habit you have to unlearn. And we know that's not the easiest process, and we're all busy, so we really don't have time to unlearn things. We need to just go ahead and start getting clear, maintaining boundaries from step one.

And we'd love to know what did your first client teach you that you eventually had to unlearn? Because it is the natural part of the process. Send us a DM and let us know. Until next time, you can now follow us on LinkedIn at Entrepreneur Encounter.

Thanks for spending time with us today. If something in this episode gave you a fresh perspective, share it with a friend or send us a DM. We love hearing how these conversations land with you. And if you're curious about how soft skills can support your next season of growth, we each have more resources to share. You can find Dana on Instagram at Dana's.desk.nc for pinch a strategy and intentional marketing. And Sarah.

at You Are Rembert for team development, business leadership, and podcast support. Until next time, keep leading with purpose and growing with intention.