What Hiring a Stylist Taught Me About Building a Successful Business

Imagine hiring a stylist because you think she’s going to clean out your closet and just like tell you what to wear. Only to get handed a big lesson that I think we all need to be reminded of from time to time about our online businesses. So here’s the deal. 2025 is a really big year for me. You’ve heard me talk a lot about how my book is coming out, When I Start My Business, I’ll Be Happy. It comes out April 15th.

But also my book is not only just like that’s not the only thing, right? In addition to all my business stuff, but also my book is coming out and bringing along with it a lot of new opportunities that maybe wouldn’t have otherwise been available to me in the past, or at least were like super hard for me to get. Like the things that I’ve been knocking on the door of are only finally opening now that I have a book, even though I’m the same person doing the same thing, right?

And with all of these new opportunities, it’s feeling like an invitation for me to take the next step in visibility, in being comfortable, like owning my stuff, right? And stepping a little bit outside my boundaries of my self-imposed boundaries of talking about legal stuff for the last eight years, which is still what I do. I’m still lawyer and still sell legal templates, but I’ve also learned a lot in the process of doing so over the past eight years that a lot of you ask me for help with, right?

And so a while back I decided, I’m a big believer by the way, in like whatever thing is, you know, bothering you or whatever thing will give you more confidence, like whatever thing you should do that thing and really forget what everybody else has to say. Like, I don’t know, many years ago, like 10, no, like 13 years ago, I went and got a veneers from my teeth because I hated my teeth. I hated my smile. My teeth were almost, I didn’t like it, right? I beat myself up over it thinking like I was so vain, I should just get over it. It was the best thing I ever did.

And when it came to hiring a stylist, I felt the same way. was like, I should know how to dress, you know, myself. Like I just turned 37 in November. I’m like, I know how to get dressed. I don’t need to get, I don’t need someone to teach me how to get dressed or is like hiring a stylist admitting that I have bad style or I don’t know how to get dressed. I had all of these stories in my head, but finally I applied the same logic of like, you know what, it’s going to make me feel more confident given what I have coming up this year, which is a lot of big stuff.

And there’s a big difference in getting dressed to run for coffee or going to the beach, which I am very comfortable and confident doing versus going and giving the biggest stage talks of your life. Right. So I decided I wanted to hire a stylist, Connie, to help me put together some outfits for things that I have coming up this year, like talks, like I have one coming up later this year that I cannot wait to tell you what it is because it was literally the thing that I was like, if I ever got this speaking gig, I will like call it a day and retire. And I got it and I can’t believe it, but I’m not retiring.

But I need outfits for things like talks and you know, big podcast interviews that I’ve also landed, which I can’t believe. and media appearances that are inevitably going to come with my book, all the book talks and the book signings and the book parties and like, there’s just gonna be a lot of outward stuff this year that is a little slash a lot outside of my comfort zone. And part of me was also just very excited as a side note to clean out my closet because I wanted to be able to just walk in my closet and see simplicity. Like if I could see actually fewer things, I just, and have fewer decisions, I would feel so relieved.

And so I went to Connie and hired Connie and thought, you know, this is why this is what I’m coming to her for: just want you to tell me what to wear to these events. Tell me what to get rid of in my closet. Just like tell me, this is impassionable or this doesn’t look good and just get rid of it and just make my closet look like, you know, very streamlined, very simple. As I told her I wanted capsule plus because I wanted like capsule with some interest and capsule with some color.

So I hired her and I thought she would help me pair down my closet, like I said, but I also just thought she would tell me like straight up, wear this with that, like just put these two things together and that’s it, like no thinking about it. Instead, and I’ve only been working with her for like a month, but instead what I’ve actually gotten out of it has been so much more. And it’s actually the same lesson, just in this case about clothes and cleaning out your closet, that we all have to learn and integrate and re-remember about building our businesses. So I’ll get to that in a sec.

So when I started working with Connie, the very first thing we did, we had these like two style sessions that were broken into two, two hour chunks. And the first one was all about bottoms. So I tried on all these jeans that I own and that I love. And by the way, I consider myself a jeans girl. have had quite the jeans collection before, before this session. And I would have told you like, I’m fine. Like I have all these jeans, but there was always like something missing, right?

And so I try on all these jeans with her virtually and I’m showing her on, on zoom and stuff. And I thought she would be like, okay, keep those. Don’t keep those. Those are good. Those aren’t good. Those look good. You don’t look in that, you know, but instead Connie started asking me a lot of questions every time I tried something on. Like, how do you feel in those? How do they align with your style? How do they align with your style words?

Like we came up with all these style words and descriptors and we did all these really cool exercises before. We got on the call and my style words for example were, which probably doesn’t surprise anyone, was like cozy, chill, casual, coastal California, beachy, French inspired, right? Those were my words. And so when I was wearing something, I was like, yeah, I mean, it looks fine. She’d be like, well, how does that relate to like what you’re going for? Like, it’s not, it doesn’t feel okay, so like how often do you wear it? I don’t.

Like maybe because it doesn’t align with my style just because it fits or it looks good or whatever, right? So she would also ask me like, how much do you wear it? Like, where do you wear it? How do you wear it? All this kind of stuff. And when I would say how I wouldn’t wear it that much, we would then go deeper as to the why, right? So I would just be like, hmm, kind of having this realization. Like I said, I like these jeans, but I don’t ever wear them, but why? And so we started measuring things, which that really blew my mind. We measured the inseam. We found my go-to measurement.

Then found the, which I’m only five four, so it wasn’t very long. It was kind of sad to measure actually. And then we measured the rise to find this like commonality amongst all these pants that I don’t wear specifically at home. Like one of the problems I was trying to fit, I guess, was like, I have all these jeans, but they don’t also meet my lifestyle. Like even if they meet my style words, they don’t mean my lifestyle. I work at home pretty much 24 seven.

If I do go out, it’s to a coffee shop or sometimes I go to the library if I really need to write. And so I don’t like to sit and have pants digging into my ribs, you know? So I had all these pants that I just wasn’t wearing and they were too uncomfortable to wear with my current lifestyle. So a few days later, we get on the same call and we do the same exercise, but now with tops, right? So I tried on one after the next.

Pretty much striped, every variation of stripe that you can think of, I’ve got it. I’ve got like every weight of long sleeve shirt, every weight of sweater, every color combo stripe. I have like a stripe factory happening. But that does meet my style where it’s a French inspired and beachy. So I’ll take it. But I tried these all on to show her what I have and stopping to tell her along the way. Now that I’m like starting to pick up on this like, I have this piece, I never wear it. Like, why am I keeping it?

Or I would say to her, I have this, but I never wear it because X, Y, Z. Sometimes it would be like, I never wear this because I don’t love the feel because it’s synthetic fabric. That was something that came up a lot. It like, it’s synthetic fabric and it just doesn’t feel good. It makes me a little overheated. It makes my skin feel a little funny. I don’t like it. I think it looks a little cheap or something. I don’t like like the cut of this.

I kept telling her, I thought some of my shirts looked too boob forward and like my boobs were entering the room first and I don’t like that. So it was like, you know, there were different reasons why I liked certain things or didn’t wear them or like, I liked the way it looks and maybe I would love it on you, but it just didn’t work for me. Right. And when I would explain this to Connie, like, I don’t love this sweater because it’s tied on my arm. She would then stop and teach me this is why.

Do you see where the inseam runs? you see where the seam that do you see how there’s a seam running up your shoulder? Or we would start to notice these commonalities. Like, do you notice that every time you have a drop shoulder on like I’m wearing now, it’s much more comfortable? Do you notice how that kind of softens your shoulders because you have broad athletic shoulders, you’re very strong. So you feel a little bit more like cozy and chill, which aligns with your words, right?

And she also like, I have to give a shout out to Connie. She’s @artinthefind on Instagram. I’ll link her down in the show notes. But she also, I felt like very empowered the entire time because she was not saying like, this is the right way to wear that or that’s a bad top or you look bad in that. Like if I would really push her, like really, really push her, she would be like, if we were going shopping together, I wouldn’t encourage you to buy it. I think that would that was like the strongest thing she said. But instead, we really tuned into how I felt, what my goals were, you know, how I wanted to look and feel, whether things aligned.

And then once I started noticing this pattern, this is what was like so mind blowing to me. Once I started noticing this pattern of like, all shirts that have that stitching that go this way across my shoulder, for example, don’t they’re not very flattering and they’re not comfortable. That’s why I never wear it. Literally towards the end, I was just getting there to be like, nope, don’t even have to try this on. I never wear it. And now I can see why. Like it was just becoming so obvious.

We were really meeting me where I’m at in my life right now. I’m not a corporate lawyer anymore, thank God. I don’t need suits, I don’t need overly formal clothes. I don’t live a very fancy lifestyle, at least the way that I would qualify that in the way of getting dressed up and going out a lot. I don’t do that. I work at home, I’m home a lot, my friends are all really chill, thank God. When I go out to dinner, I wear my nicer jeans and a sweater.

So that’s me. And I’m just like, trying to get more and more comfortable with being like, that’s just me. It’s okay. I don’t have to keep buying, as Connie would say, like buying aspirational clothes for this like other person that I think I’m supposed to be, but that’s not me and it’s not my life. And it doesn’t align with stuff. And like, no wonder you buy stuff that then sits in your closet. RIP to the suede jacket that I had to get rid of that is like literally not me ever. I don’t know why I bought it. So here’s the deal. Here’s how this relates to your business.

I can see this scenario playing out in so many other arenas in our lives. Like when you want to improve the way that you feel through your diet or if you’re a coach and somebody comes to you this way, right? And they want to improve their diet. And that person just wants to be handed a meal plan instead of learning how to build a healthy meal or build a healthy plate. Or, you know, somebody wants to improve their strength and they want a magic bullet. They want to know if they can start taking, you know, colostrum and I don’t know, some other thing, right?

And they want to get some quick fix instead of hearing that it actually takes a lot of repetitive long-term effort to build muscle, for example. And I see this all the time in business, in online business, when people bounce from course to course or to freebie or to podcasts or to their new creator obsession du jour on Instagram because now they think that this person they just found out about on Instagram has the answer.

Like in reality, as business owners, we have to learn why what we’re doing is working or not working or why certain things work a certain way, right? For example, I’ll just pull this one off the top of my head. For example, like when you’re designing a freebie, like opt-in, for example, to get people onto your email list and then you’re going to write some sort of nurture sequence. That’s a series of emails people get after they opt into your freebie. You’re not just throwing spaghetti at the wall or mimicking the one that I have or listening to a single tip that someone gives about something that should be in your nurture sequence on Instagram.

Instead, you have to understand the psychology of like someone coming into your world. First of all, you had to understand a lot about their psychology in order to get them to opt in because you needed to understand their problems, their desires, the solution to their problem and solution awareness, for example, but you also then in the nurture sequence need to understand what elements need to be met in order for someone to hang around in order for them to convert or do the next thing that you’re asking them to do in order to properly nurture them, right? That’s why it’s called a nurture sequence. There is a science to it. It’s not just about somebody setting this up for you and then going, here you go.

Good luck, run off with this nurture sequence because what’s going to happen the next time that you need to write a nurture sequence? Because I have bad news for you. When you have your own online business, you need to be consistently creating new freebies and you need different nurture sequences that pretty much go with all of them or at least have emails that connect to a main nurture sequence. And you need to understand the elements of why a nurture sequence, this one works versus that one doesn’t, or why mine’s good versus somebody else’s not converting, right?

We need to learn why we’re doing what we’re doing. And just like my clothes, we also need to know what your goals are, not mine, not hers, not theirs, right? What your goals are and how you want to feel. And that also is based on how you want your business to feel and look. Like if we were using the clothes analogy, right? Like you have to be clear on what that style vibe is for your business.

And when you go to do anything in your business, you need to ask yourself, does that match up with the vibe I’m saying I’m giving? Because that doesn’t really sound right. I mean, I even think about that with myself with like, I’m very, you know, I would consider myself to be a very chill, cozy business person, but some of my actions don’t match up with that in terms of where I spend my time or put my efforts and energy, right?

And so that’s something that forces me to like have to check myself sometimes to be like, you say you want chill and cozy, but then you’re like pouring a lot of effort into social media and it’s not feeling so chill and cozy right now. You know, it does feel chill and cozy. My podcast and I put it aside for a few months to finish my book, right? Last year. So that’s where it’s like our opportunity as business owners to make sure that we are aligning our time and our efforts with where we say, you know, or how we say we want our businesses to feel.

We need to match up your actions to your clear vision and that vision, the steps to getting there, understanding why things work. It’s not coming from someone else. There is no Connie coming to teach us how to run our businesses, right? She didn’t tell me how to do that with clothes either, but it’s, they’re not coming to tell you pair this email with that social post and that will equal success. Do you know why? Because no one can do that for you. Nobody, nobody but you.

Because being an online business owner takes a lot of practice. I feel like that’s the news or the truth that just nobody wants to hear, but it takes a lot of practice, a lot of time, a lot of iterations, a lot of marination, a lot of things, right? A lot of hard work and effort.

And I think what a lot of people don’t understand is that it’s not just like, for example, it’s not just like if you went up to bat for a baseball game and you just like, okay, you just throw me like a thousand pitches and by the end of the thousand pitches, I’ll be hitting like Barry Bonds, right? That’s not how it works because even Barry Bonds, for example, in the beginning, let’s put like natural talent aside, but in the beginning when Barry Bonds wasn’t making contact with the ball or was only hitting singles and not home runs, he had to understand why. What was it about his stance, about his reading of the ball, about the curve of the pitch, right?

Like you start to get very tuned in to why are these things working? Why are they not working? Why is this thing sticking or landing? Why does it not feel good for me, let alone why does it not work for other people, right? And that takes a lot of freaking time and practice. The same goes for legal stuff for your online business, by the way. You don’t need to become a lawyer, like you don’t need to become any of the things I’m saying. Like I don’t need to be a professional stylist. That’s not the goal.

The goal is for me to start to understand a little bit, have a basic working knowledge of like, why does this thing work? Why does that not thing work? Why are these colors? Why are these colors better for me versus those colors? Not, you know, either muting my tone, whatever. That’s helpful for me to know. I don’t need to be Connie though. There’s always going to be a Connie in the world and there’s always going to be a me and that’s what makes the world go around. Right? Luckily I’m a lawyer. You don’t need to be a lawyer. Everyone who owns their own business doesn’t need to become a lawyer, just like I don’t need to become what you are, right?

But you do need, as an online business owner, you do need to feel confident that you have the right pieces in place to confidently go out there and promote and market your business and take on clients and like proudly own and share what you’re doing. And that requires you to know what those pieces are that you need to have in place, right? You need to know what legal piece is in place, needs to be in place in order for you to be confident.

So just like I now feel more confident that the pieces in my closet actually fit me and I understand why they fit me and why certain seams are working and rises are working and et cetera and why they feel good. And I feel better about the fact that they match my vision. And I’m asking myself that as I’m seeing things out and about like, Ooh, that’s cute, but it doesn’t match like my vibe, which is why it’s going to sit in my closet and be cute. There are lots of cute things in the world.

But they’re not gonna ever get worn because I don’t live that life or that’s just like not, it’s just ultimately not me even if I think it’s cute. It makes my life a lot easier to build that outfit confidently knowing at least the information I do know now. And so as much as I could sit here and say, I’ll just do this and this and this legal thing for you and now you’ll be legally all set in your business which is what I used to do as a lawyer, right? That’s what lawyers do. They’re just service, right? They just, you come in, you take care of it and that’s it. But as an online business owner, things are a little different, right?

You are, it’s the proverbial like standing in your closet trying to get dressed every morning. every day in your business, you’re gonna stand there and say, wait, what do I do if this client doesn’t pay me? Or what do I do about this client who’s ignoring her invoice? Or what do I do about that person on Instagram who I see keeps taking my content and changing like just a couple words to make it their own. Do you feel confident enough to actually stand up for yourself? Do you feel like you have the pieces in place? I don’t know. You’d have to tell me, right? I just believe in life in business.

You’ve got to do what you’ve got to do to learn just enough or to take on what you’ve got to take on, get the support that you need just to be confident enough to start putting yourself out there or to start doing some of these things yourself, right? So that is why I highly recommend that you come to my free live legal workshop that I’m hosting next Monday, February 10th. It’s my only one of two live workshops I hold for the entire year. The next one won’t be until the end of 2025.

So if 2025 is a year where you wanna get your business up to legal stuff and you wanna get all of these things in order, definitely click the link in my show notes, sign up for my free live legal workshop, five steps to legally protect and grow your online business. I hope to see you there. Seats fill really, really quickly. So make sure you go and sign up and then send me a DM on Instagram. Let me know that you listened to this episode. Let me know how it resonated with you, this made, if it was helpful, if it made any sense to you, but also let me know if you went ahead and signed up for that legal workshop so I can thank you.

So send me a DM on Instagram @samvanderwielen, or reply to my email if you get those every week. With that, thank you so much for listening and I’ll see you soon.