What Keeps New Personal Stylists From Feeling Ready to Launch

You've probably said some version of "I'm not ready yet" about your styling business and felt like that was the responsible answer. Maybe you're still researching platforms, tweaking your offers, or telling yourself you need a few more clients under your belt before you can really go for it. From the outside, it looks like you're doing everything right.

But most stylists I've talked to in this phase can't actually name what "ready" would look like. Not a number of clients, not a specific milestone. And without that, you end up stuck in a loop of researching, adjusting, and preparing that can stretch on for years. What I've found is that readiness isn't something you wait for. It's something you build. And most stylists are missing the one thing that would let them build it.

In this week's episode of The Six Figure Personal Stylist Podcast, I'm talking about what's really going on when you don't feel ready to start your styling business, what I learned from talking to hundreds of stylists who felt the same way, and the one thing that actually builds the kind of trust in yourself that lets you move.

00:49 – A book passage about a ceramics class that shows why the group trying to make the perfect pot ended up with the worst results

3:24 – Why "ready" is not a threshold you eventually cross and why you're actually waiting for a feeling that keeps moving

8:20 – The specific number of clients outside of your friends and family you need to work with before you can legitimately start charging professional rates

9:41 – The difference between raw experience and "evidence" and why only the latter leads to certainty

12:30 – How a lack of repeatable structure is often misdiagnosed as a lack of confidence or talent

16:57 – What this misdiagnosis looks like day-to-day as a stylist launching a business from scratch

19:36 – Why staying in the preparation phase feels neutral but is actually the most expensive decision you can make

21:37 – One question to ask yourself to find out if you're waiting to be ready or waiting for permission no one is coming to give you

Mentioned In What Keeps New Personal Stylists From Feeling Ready to Launch

Art & Fear: Observations on the Perils (and Rewards) of Artmaking by David Bayles and Ted Orland

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Transcript

Nicole Otchy: I am not ready yet is probably the most common thing that I hear from stylists at every phase and stage of business. Or, do you think I'm ready yet? And the tricky part is, you can actually stay in that place for a long time and still feel like you are being productive and doing everything, quote, right in your business. 

And so today we're going to talk about how to break this cycle for good. I'm Nicole, and this is The Six Figure Personal Stylist Podcast. And this show is for personal stylists who want to build world-class businesses and lead the industry. Every episode is built to help you grow a profitable styling business rooted in thought leadership and real transformations. Because the best stylists don't just edit closets, they shape culture. Let's get into it. 

A while ago I read this book that I was recently reminded of called “Art in Fear”. It was written by two photographers and it's been passed around in creative circles and communities since the 90s. I read it in a philosophy of art class and I remember really loving it. But recently I was scrolling on TikTok, before I had to take it off my phone, for like the millionth time, in the last three months, because I'm addicted, but that's another episode. And I couldn't stop thinking about it in relation to something I have been hearing stylists say with respect to this, am I ready yet, I'm not ready yet, on all of my discovery calls this spring. 

So there's this passage in it about a ceramics class. And on the first day of the class, the teacher divides the class into two groups. One is going to be graded on quantity. The more pots they make, the better their grade will be in the class. The other half is graded on quality. They only need to produce one pot, but it has to be exceptional. So you've got one group that just makes pots, churning them out, hundreds of them in the semester. They're trying things, they're noticing what works, they're fixing what doesn't. They're making so many pots. And you've got another group thinking very carefully about what the perfect pot would look like, before they start making anything. And at the end of the semester, all of the best pots ended up coming from the quantity group, the one who had just been making things over and over again and had naturally made them better. The quality group had spent so long thinking about perfecting their pots that they barely had anything to show for it. In fact, some of them didn't complete it at all. 

And that's what this conversation reminds me of, because I have been on so many discovery calls, because I've just gone through multiple launches. And I really do keep hearing either a version of this declaration, I'm not ready yet, or how do I know when I'm ready? I hear that in my coaching as well. And I really understand why it feels like the right question, specifically coming from my clients and my audience, because I attract a very thoughtful, smart, usually very good student, or like very conscientious student energy, in my clients and I love them for it. 

And when you're in the early stages of a business, or entering a new stage of your business, readiness feels like the thing standing between you and quote a real business or real income. Or as many of my clients tell me when they get comfortable, I don't feel like a real stylist. And the assumption here that we don't say is like there's some point you have to reach, some amount of experience or confidence you have to build up to, before you can legitimately move forward. But  readiness, in any area of your life, is not a threshold. If readiness was a threshold, you would be able to name it. If it was a real point in time, a real marker, you would be able to say, oh, I've hit that point and now I'm ready. 

But the truth is, most of us don't really know what ready looks like, how many clients, how much experience, what specifically needs to happen to arrive at that magical moment of “ready”. And in my experience, most people cannot name it. They cannot name what that threshold is. And so that means you're not really waiting for this point, this marker, this threshold. You're waiting for a feeling. And most of the places I see stylists getting stuck in their business, is waiting for a feeling. And the problem is that feelings keep moving. You get a little more experience and instead of feeling ready, you just find the next thing that doesn't feel solid yet to focus your attention on. So the goalpost moves constantly and you stay where you are. And I've seen talented stylists stay in this loop for years as established stylists, but I've also worked with many, many, many brand new stylists, before I started the styling consultancy. And this keeps more stylists, who want to launch businesses, stuck than just about anything else. 

And so I want to walk you through what's actually happening when you don't feel ready. Because it's not something a lot of people talk about, but it is the foundation to everything we're going to talk about for brand new stylists and even advanced ones. These are not concepts when we're talking about the mindset pieces of growing a business that you ever outgrow. Because we all have our own patterns and you tend to, no matter how far you get in business, go back to your patterns. And it's not about getting rid of them forever. It's about how fast you can break out of your own spirals, or your own thought loops that are keeping you stuck. 

So early in my career, I spent about a year and a half. It actually could have been longer, but I know for sure that it was a year and a half, so I'm going to say a year and a half, doing sales calls for a program that helped me launch my own business, back almost 20 years ago called “The Paid Stylist”. And it's one that I went on to mentor in, to write programs in, to become the communication manager in and then to do sales calls for. And so in that role, I talked to hundreds of stylists every month. And who I was talking to were mostly women, who were very talented, who had lots of real life experience, not always formal training, who had been styling people informally for years. And they kept saying some version of, I just need more experience. And so I told the woman who was my boss and created that program, I said, they keep telling me in these sales objections that they don't have enough experience. And we had different levels of programs. What I'll say about her, her name is Michelle, is she was one of the best salespeople I have ever met in my life, and I wish I had… I didn't know enough about sales to realize it, but she completely, first of all, shaped the industry,and second of all, completely showed me things about sales that I didn't even realize I was learning. And she told me to ask this and I didn't really get it, when she told me to say this. I didn't get that she was teaching me how to handle an objection. I just did what I was told at the time. What does enough experience actually look like to you? That's what she wanted me to ask people on the sales call. I didn't ask her why. I was very naive at this point. I was, I think, probably in my 20s. And so I did. And I think I probably executed this wrong, because I probably, like, didn't pause after I asked. I probably was like, five clients? Ten clients? How many clients? I probably pushed for, like, an answer. 

But what I do recall is that almost nobody could answer the question. And I think about it a lot now that I'm going to be starting to work with new stylists and even just having this business. What I came to believe, after having all of those conversations over and over again, for years and continuing to have them now, is that there are actually a number of people that make you ready. And I'm going to tell you what it is. Five real clients outside of your friends and family is enough to start charging, quote, real rates. Not perfect clients, not people that are going to be lifers with you. Not even services that were perfect, real people who you didn't already know and who didn't already trust you. So this can't be your mom, your mom's best friend, your sister. I'm talking it could be like your sister's best friend's brother, right? It could be your neighbor's colleague. It doesn't matter how they get to you. It matters that they don't have any relationship with you and you don't have any way of intuiting their preferences and way of being, so that you're guessing at whether they like things or not, when you work with them. 

That's enough people, five strangers, to have learned enough, especially if you can execute on your packages in a way that I'm going to talk about in an upcoming episode, I'm going to tell you what your first packages should have, to have learned enough to charge a real price. Most of the stylists I have talked to or reached out to me in DMs from listening to this podcast, have already done that. But the reality is and we're going to get into some like learning psychology and theory here, when your brain doesn't have a structure to measure things with, you will fail to recognize heaps and heaps of real legitimate experience as evidence of readiness, as evidence of legitimacy, as evidence of being ready to launch a business. 

Evidence is a very key word here, and we're going to spend a minute with it. Because experience is the raw material. Most of you who are listening already have that to a varying degree. You have experience styling friends and family. You have experience styling all kinds of folks. But evidence is what accumulates when you repeat the same process repeatedly and it produces results. And it is evidence that creates certainty. It is evidence that creates what most stylists are chasing, which is a feeling of readiness. And you can't think your way to that. You cannot research your way there. You can't take another course. You could not listen to every episode of this podcast. You could not listen to every episode of my old podcast, when I was a stylist, which many people have done, trying to feel ready. And you cannot spend another six months tweaking your Instagram bio and think that you're going to hit one that makes you feel ready. 

Because evidence only comes from doing the work inside of a structure that you repeat. Without that, every session you do, with a potential client, or a legitimate client, a real client, is just a one-off. And nothing compounds. So you keep waiting to feel ready. And for most established stylists, this often shows up in waiting to feel like, quote, a legitimate stylist, despite the fact that strangers are already and regularly paying you and finding you online and working with you. It is when we don't have a repeatable process and structure that we do with our clients that we're not bending. This is not a choose your own adventure situation, that we build our own expertise and we create the evidence to feel like we have mastered something. 

And so the stylist I see in this pattern of always waiting to feel ready, are missing structures. They have skills, but they have zero repeatable process. And so I am in many ways speaking to the stylist, who's getting ready to launch their business and feel ready to do that, feel prepared to do that. What I am saying is true, you have to get evidence inside a repeated structure that gives you data that tells you why something is successful, in order to feel like you are achieving mastery. Most of the time what I see is that stylists spend a lot of time and this includes new stylists, beating themselves up over not having enough talent, when what they are actually missing is a repeatable structure, in their business, in their styling containers and how they actually execute on them. How they actually commit to doing a closet edit, the questions they ask of the client, how many hours their shopping is, how many pieces they're typically giving, I mean, give or take a couple, to their clients, how many times they're actually editing a shopping board for a virtual client. 

All of these things need to have a structure or else you will just misdiagnose the problems in your business. And usually, and this is what I see the most, you will spend years not getting paid like the expert you are. So you're accumulating all of this evidence, but you're not in any way accumulating a sense that that experience is leading to mastery. And what makes this harder is that the advice that most stylists tend to get, at the beginning stages of business, really creates a bigger problem. When a stylist doesn't feel ready, a business coach, their partner, their mom, people that mean well, will tell them things like, they need to work on their confidence, they need to work on their mindset, they need to sell more, they just need to get out there more and get more followers. 

And sure, I'm not going to say those things don't matter, but at this stage, when you are starting a new business, or when you're going into an entirely new market, or trying a whole different thing as an established stylist, those things are not the problem. You are not lacking confidence, because you have a bad mindset. You're lacking confidence, because you don't have a structure that produces consistent results. And your brain and your integrity is rational enough and developed enough to notice that and think, I'm not really going to do this, because I don't want to seem like I'm faking it. Now, sometimes you have to fake it in life, I'm not going to lie to you. But when you are trying to charge a lot of money, or you want to make a styling business your full-time gig, most of you are very good at what you've done in your life. You come from corporate backgrounds. So many of the stylists I work with that are new to the game have big jobs or had big jobs and they need to make real money and they're like, I need a structure to do this. 

And I want you to think about what you do with your own clients, to sort of shift the lens on this. When a client says she doesn't feel confident in clothes or in shopping or in getting dressed, you probably do in a moment try to reassure them. But you know that if you just handed them a book on self-esteem and sent them home or told them, oh, you look fine and left it there, it wouldn't do much, right? So what do you do as a stylist? You show him or her what works. You guide a client through choices that actually change how they see themselves, by showing them how the clothes work, how they fit with their body type, how the colors make them look, you know, more alive. And you notice over the sessions that their confidence builds from the evidence you are showing them with the knowledge and the follow through, by putting the clothes on their body and seeing it in the mirror that they're getting. It's not just, oh, best of luck. Think about it a little differently. You're both talking to them and explaining it to them and you're showing them with the clothes. And just like your clients don't become confident, because there are great outfits just sitting in their closet, they become confident, when they actually wear them and they understand why they make them feel or look the way that they do. Your business works exactly the same way. You don't build confidence by thinking about things in your business. You build it by doing the actions inside a structure that actually produces results. 

And here's what this usually looks like in the day-to-day for a stylist who's building a styling business from scratch. You are waiting to feel ready. You are waiting to leave that full-time job. You're collecting a lot of evidence on Instagram. You're following a lot of stylists and thinking there's no way I will ever be where he or she is. You're consuming content like this podcast. You're taking notes. You're tweaking your offers. Maybe you have a website or maybe you're waiting for, you know, the perfect offer or pricing system to come down from above, before you make that decision. You keep researching what platform would be best. You keep tinkering with the idea of turning your private Instagram account public. I'll stop you right there. Just go start a new one, I promise it will be worth it. You do a few sessions with acquaintances, but if something doesn't go perfectly within those sessions, you drive home, you beat yourself up and you start second-guessing yourself. 

Then you go back to researching and adjusting, and you think, OK, I'm going to stay on this job for another six months, eight months, 10 months. But you don't actually have a marker of when you will be ready. And this loop can go on for years. And the issue is not the waiting. It is that nothing is structured enough, in your approach, to prevent that spiral that then leads you to another six months of preparing for this thing. And so your experience isn't compounding towards expertise. You're just sitting here waiting to feel a feeling called ready. 

What I want to tell you if you are listening and considering being a stylist or you're in the very beginning phases of a styling business, meaning you're mostly just working with friends and family, you're not getting traction with strangers, which is an important and legitimate phase that you have to go through that, in order to like get to the next level. What actually turns that into a legitimate business is not becoming more talented or more skilled as a stylist. Those things will help, but they won't make you feel ready. It is about mastering your process, your consultations, your decision-making, your boundaries with your clients and your offers. And you can only build those skills through repetition. And they build faster, when those reps happen inside a predictable routine and structure. Because then each experience teaches you something. It creates evidence. And that evidence is what your brain uses to trust you. And it's also what the majority of you, who have a very good sense of integrity, are looking for before you launch. 

And I want to talk to you about what staying in this phase costs anyone who wants to be a stylist. Because we tend to think of this phase as neutral. And that is very dangerous. We think it is less problematic than trying and failing to stay in the research phase, to stay in the getting ready phase. It feels like you're preparing, but you're not building the evidence that would actually prepare you to work with more people that will pay you and make this a legitimate business. And so a lot of people in the styling world stay here for years, without anything forcing it to change, because they don't have anything on the line. But nothing then changes either. And so every month you stay in this place of researching and getting ready is a month where you're not charging at all, or you're undercharging, or you're not getting the experience you need for this to become a reliable and serious business. And at the moment, it feels safer than going for it. But over time, you realize that waiting is the thing that is the most expensive decision, because you're never gonna feel ready, but you can't get those years back. 

And if you're in this phase, where you keep thinking that you need more time, more clarity, more experience, this is exactly what my Foundations of Professional Styling program was designed to address. Foundations gives you the structure to build your styling business properly. so you're not trying to figure it out on your own and waste years to get to your income goals. The waitlist opens for this new program on April 20th and the link is in the show notes to join the waitlist to get a very special one-time price and some additional support that will not be offered in continued rounds. 

I'm going to leave you with this. I want you to remember that quality group in the ceramics class that I opened the show talking about. They were not less talented. They were not less motivated. They just spent the whole semester waiting to make something worth making, instead of making anything at all. And at the end of it, they had a lot of theories about what would make the perfect pot, but not much else. 

And so if you're waiting to feel ready, ask yourself something. What would ready actually look like? What's the number of sessions? What are the specific things and the markers I want to have that would make me ready? What would make me say one day when I woke up and I met those conditions, okay, now I'm ready. And if you can't answer that, you're not actually waiting to be more ready. You're waiting for permission and nobody is coming to give it to you to start your styling business. 

The only way is to build something in a structured, repeated way to get in the reps, to get the type of experience that is actually going to lead you to feel legitimate and let that evidence accumulate. That is the only thing that is going to move you forward, towards your goal, of having a professional and full-time personal styling business. Not more time, not more research, a structure that you can actually learn and repeat and get more expertise. I will see you next episode. 

Thank you so much for hanging out with me. It turns out that social proof is actually pretty important. So if you could help me out, I'd so appreciate it. If you just had a quick free moment and could leave me a rating or review on the podcast app, that would be killer. And even better, if you wanted to share this episode on Instagram and tag me, that would totally make my day. And it would bring so much more awareness to the podcast and would help other stylists, just like you, who are looking to build a lucrative styling business. Because the better each of us does, the better all of us do. 

Thanks for hanging out with me and I'll chat with you next time.