Why You Still Haven’t Figured Out Your Style (and Why That’s Okay)

You’ve built a successful business. You’ve landed the clients and scored the speaking gigs. You’re a confident, capable, and resourceful woman. But staring into the closet in a panic before a big event or questioning if an outfit aligns with your brand is a common occurrence for many high-achieving women. So why does personal style still feel like something you should have figured out by now but haven’t?

In this episode of The Visibility Shift, you’ll discover why you have the belief that you should have figured out your style by now. I’ll share the deep-rooted beliefs that cause women to over-effort in their style, how shame and the “bootstrapper mentality” keep us stuck, and why more shopping doesn’t equal more alignment.

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2:31 – How the bootstrapper mentality holds you back from gaining clarity

3:31 – Why style shame is real and widespread

4:45 – Why over-efforting may feel productive but doesn’t equal alignment

9:03 – How going it alone in your style journey is costing you

10:07 – Example of how over-efforting taxes you and why bringing in the right support is critical

13:57 – Next steps and your permission slip to step into authentic alignment with your style

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Full Transcript

Welcome to The Visibility Shift, the podcast where style becomes your most powerful strategy for being seen, standing out, and leading boldly. I'm Ellie Steinbrink, stylist and personal brand coach, and if you've ever thought, "My style just isn't working anymore," take this as your sign. You're ready for your next level. And instead of launching into a panicked shopping spree, what you really need is a strategy. A style strategy that reflects where you're headed, not who you used to be or who you think you need to be to fit in.

Because when your style aligns with your brand and your vision, everything shifts. You lead with more presence, you attract the right opportunities and clients, and you fully step into the woman you're becoming. Because showing up as yourself, that's the most strategic thing you can do. Now let's get visible.

Welcome back to another episode of The Visibility Shift podcast. I'm thrilled to be sitting here with you and back in the swing of recording. Today, I have a powerful reflection for you, especially if you find yourself smack dab in the middle of conference and speaking season. If there's one thing I know about you, it's this. You know how to figure things out and get the job done.

Listen, you've built a business. You've figured out your message. You've figured out how to differentiate yourself. You've chased after and landed those speaking gigs you wanted so bad. You've gone after the clients and got the dream clients in the dream meetings. Listen, I know you're confident, you're smart, you're resourceful. You are a bootstrapper. So why does style feel like the one thing you should have figured out by now?

That quiet voice, or maybe not so quiet voice, that says, "I should be able to figure this out," is something that I honestly hear from so many women, whether they're my clients or just women that I speak with when I'm out at networking events and speaking events. If this is you, I gotta let you know that you're not alone. Today, this is what I want to talk about.

I want to unpack why we have this belief about we should have been able to figure this out by now, how that belief is keeping you stuck, what over-efforting in your style really looks like on a daily basis, and how you can finally find that clarity and alignment that you're craving. So where is this idea that we should figure it out by ourselves? Where does it really come from? There are three big things I think of.

One is this idea around being a bootstrapper. If you've been running your business, if you've been building a brand, you are a high-achieving woman who figures things out. Whether you're an entrepreneur, a speaker, a leader, this is what we do. This is how we've built the businesses that we have today. Honestly, we pride ourselves on that, on being resourceful, on figuring it out. Listen, I'm sitting here right alongside you.

I get it. I'm a farmer's daughter from the Midwest. This, "I can handle it. I don't need help. I can figure this out mentality," it runs deep. So if this is you and you're wearing the badge of "I'm a bootstrapper, I can figure this out," this is one of the key reasons why we keep saying, "Oh, I should be figuring out my style. This is just another thing to add to the list that I should be figuring out."

Reason number two, I don't quite understand it, but I also do. But there's a lot of shame around not being good at style. This comes out in many different forms, whether it's when I'm in sessions with my clients or just when I'm talking to women. But it's this idea that I don't know why I didn't get the style gene. Or my mom was really great at style, but somehow I don't know how to dress myself.

Or I'm okay with dressing myself, but I don't really feel like I've got the skill set like other women do. I don't know why we think that style needs to be this innate baked-in skill set that every woman has. Almost like you need to be good at cooking, you need to be good at cleaning. Just stop and think about this. We don't say this about taxes or bookkeeping. But when it comes to style, we feel like it's something that we should all have.

This "If I don't get it, if I don't know how to do this, I'm feeling a little bit embarrassed and shameful about it. So I'm definitely going to keep working hard to figure this out because dang it, I can do this." But it really is leading all to this feeling of shame of like, "What's wrong with me?"

The third thing I'm thinking of that I hear reflected back a lot in my conversations is, "I should have mastered this by now." In fact, I had a client tell me verbatim, "I'm a grown ass woman. Why don't I know how to dress myself?" I really feel this so deeply. Most of the women I'm working with are in midlife.

So, on top of I've had 40 or so years to figure this out, the reality is that our bodies are also changing in the process because of perimenopause or menopause or whatever phase you're in. Everything just becomes harder than it used to be. Not to mention we've got a million other things on our plate. We seem to forget about that. But suddenly it feels like we don't know what we're doing. But still, we're blaming ourselves for why haven't we figured this out?

Maybe you're saying, "Well, I do, okay. I've gotten by for these 40 years," but you're still in the back of your mind, you're thinking, "It could be better. Why can't I figure this out?" When I think about what this looks like in real life, when we have this mentality of I can figure it out, I should be able to figure it out, this is what actually happens in real life.

We start spinning on this spinning and controlling and trying to figure out and over-efforting, and that looks like panic shopping before every big event that lands on your calendar because you look in your closet and you're thinking, "Oh shoot, this isn't it, and I better go figure it out. So I'm going to go buy everything, scoop it up, put it in the cart, bring it home." We usually end up in the same spot we started with, still nothing to wear.

Or often women will tell me that they have style bloggers or influencers that they follow whose style they really admire, or maybe they want to emulate their style, or they have a similar body type. So whatever they're wearing, because it feels like it's aligned, they'll order and they feel like, "Oh, maybe that's a way to solve my problem is if I just do what they're doing and buy what they buy, maybe it'll work on my body," but somehow it never does.

You get it in, you're like, "Why is this not working for me?" Or for the women out there who say, "I really don't like shopping. I walk into a store, and I feel really overwhelmed," services like subscription boxes or even going to a retailer like Nordstrom who has stylists, they can offer help in terms of shopping. So then that feels like we're doing something, but why does it feel like, "Oh, maybe I got a few pieces, but still I don't feel like we're nailing it."

Or how about this one? Maybe you've gotten your colors done. This is a really common one. In fact, I went to a conference last week and every other woman I talked to was like, "Oh, I got my colors done." Yay, I love colors. This is something I do with my own clients, but there are shortcomings to it. It isn't a style solution. It only gets you so far. It's only one piece of the puzzle. So, of course, you're still frustrated.

Or how about this thing? Have you ever done this? Googling what should I wear when I'm on stage? Only to end up with the same sparkly sneakers or sneakers that have a Nike swoosh in your brand color, or maybe a signature necklace because you've been taught you need to have a signature item. "Okay, I'm here to tell you that's not a brand." But it feels like you're moving in the right direction, right?

All of this feels like you're moving in the right direction. Maybe as a result of all this efforting and time and money spent, you come out with maybe two, three solid outfits that you're like, "Okay, these work. I'm getting compliments on them. I'm getting people coming up to me afterwards. They're telling me that I look great, or they're commenting on my sparkly shoes or whatever the case may be," but then you're out of ideas.

And you're about to enter into another busy conference season or another big speaking season, and you're like, "I got to go through all of that again to find another set of outfits? Are you crazy?" So while you're toiling away, have you ever stopped to think what this is costing you? It's not just your time or your money or your closet space.

What I hear beneath the surface when I'm talking to my clients who have been through this crazy cycle, or women who are currently in this crazy cycle, and they're trying to figure it out, what I'm hearing beneath the surface is when you're over-focusing on figuring out your style, you're distracted. You're second-guessing yourself instead of preparing for that keynote.

You're worrying if your bold look that you're like, "Oh, I'm going to go, this is it. I'm going to go take a bold chance, and I'm going to go take a risk." You're wondering, "Oh, is this credible enough or will I look crazy?" Your confidence is actually getting knocked down a notch or two, which is weird because you've always thought of yourself as a confident person.

This is energy you could be putting into your business, but it's actually getting burned up in your closet. This actually reminds me of a personal story where I was over-efforting. Okay, because I can speak to this, you guys, I can speak to this so clearly because I am you. I am that bootstrapper that believes she can figure everything out. A few years ago, I was really struggling with a close relationship in my life. Being the person who doesn't just sit back and allow things to happen, I was committed to figuring this out on my own.

Before I found the right therapist, I wasted years listening to podcasts, reading books, asking friends, literally signing up for these short little programs that were going to solve all my problems online. I knew if I could just keep searching and finding and reading more and listening more and talking more that I would eventually piece it all together and I could solve my problems. I even hired a couple of therapists who I thought would move me in the right direction, but didn't actually move the needle at all.

For years, I was stuck in this pattern, and I was suffering big time. In the meantime, I was getting more bitter and resentful every single minute that was passing by. It was costing me not only my peace, but my sanity, not to mention this close relationship was still suffering. Then I landed upon, I did a little bit more research, and I found a therapist who I thought, "Okay, I think this is actually going to help me get to the root of the problem," and guess what, in four sessions things started clicking.

Four sessions, you guys. This was the course of one to two months. I could see the problems in front of me so much more clearly. I realized what was under the surface that I wasn't addressing. I realized how I was getting in my own way and what I needed to do and own for things to shift, how I needed to change my behaviors, my thinking, my mindset, my actions.

I even realized how I was actually the problem in some of these cases, but it took an expert guide in front of me to reflect all of that back to me, who knew what she was doing for it to all click into place. And was this process of working with this particular therapist more difficult and confronting work? Heck yes, it was. But at least I wasn't wasting my time or energy, or money anymore.

Suddenly, this $130 per session felt like nothing compared to what I had done in the past, all these years of struggle. This is just like your style. You honestly can DIY your style for years and eventually, maybe you will land on something golden, but maybe you won't. The alternative is that you can get clarity and make quicker progress with the right support, which will allow you to move forward with greater peace of mind and confidence knowing that you're on the right track.

I know there are times when I want to dig my heels in harder and say, "I can do this," but then there are times when I've realized what that has cost me, and it's much easier for me to make that decision then. Here's what I want you guys to hear. More effort doesn't equal more alignment. Similarly, maybe you've heard me say more shopping doesn't lead to more clarity. Maybe, just maybe, less efforting on your part would actually give you better results.

So now what? Maybe you're nodding your head and you're thinking, "Oh gosh, I feel like I'm so seen right now and what do I do?" Well, the first step really is recognizing how much efforting is costing you. Ask yourself honestly, for all the time, money, and effort that I've poured into my style and figuring out my outfits for on stage and otherwise, do I actually feel aligned and powerful when I show up? Does what I've put together amplify my brand? Basically, what I'm saying is the juice worth the squeeze?

I want you to sit back and think where maybe is your look amplifying your brand and where is it maybe detracting from your brand. Second, I want to ask you to give yourself some grace. Because you have built this amazing business, this amazing brand, and a presence that is powerful and that is work and that is attracting the right things. Your business is working. But of course, it's hard to see how all of that translates into your style because you're too close to it.

Just like you'd never publish a book without an editor. Or in my case, I ended up launching this podcast with the help of a strategist because I had so many ideas in my head, but I needed someone right in front of me to reflect back and give me clarity and give me the right direction to make it a powerful experience for all of you. So why would you expect yourself to nail your style with no guidance? You don't have to figure this out all alone.

Let go of the shame and let go of the embarrassment of I should have figured this out by now. Asking for help doesn't make you less resourceful or less of a success or an achiever, it actually just makes you smart. So here's your permission slip. You don't have to bootstrap this like you have done everything else. You don't have to keep over-efforting and panic shopping and spinning in circles and feeling defeated when it's not quite right.

You can ask for help and this can be a lot easier. So if you take away nothing from this episode, I just want you to be okay with raising your hand to say, "It's okay that I can't be excellent at every aspect of my life." Because sometimes I know that's how I feel. I'm hard on myself when I feel like I should know better. I should be able to do this.

I want to offer something to you if you feel like you're ready to take a step forward on this and to ask for help and for someone to reflect back to you how your brand could be realized in the form of style. My Standout Style Kick-Starter program is the place to start. It's a one-to-one service that I've designed just for women like you who are visible entrepreneurs and speakers and leaders.

So you've got a heavy speaking season, you've got a heavy conference season. Women who need their visual brand to match the strong voice and brand that you've built. In this experience, you not only walk away with clarity about how your brand could be visualized into style, but you have a heck of a lot more confidence, and you stop the self-doubting, and you have a look that is powerful and aligned and that only you can own.

It's not going to send you out into the world with a carbon copy of the speaker that comes on stage after you or the woman across from you in the meeting. It certainly isn't going to involve more sparkly sneakers because Google told you to wear that. Maybe that's you, but maybe it's not. It's going to be a reflection of your authentic self. It's going to be something that no one else can own.

At the end of the day, that's what a personal brand is. A brand that cuts like a knife and it differentiates, and it's only something you can own in the market. So if that is something that sounds interesting to you, a link is in the show notes if you want to learn more about that. You can set up a discovery call with me to talk about it and see if it's the right fit, and we'll take it from there.

But until next time, I hope you'll remember that you don't have to over-effort everything and that you can ask for help. I'll see you in the next episode.

Thanks for joining me on The Visibility Shift. If something in today's episode made you pause, rethink, or gave you permission to stop playing small, it would mean so much to me if you'd leave a review at ratethispodcast.com/visibilityshift.

If you're ready to stop second-guessing and start showing up as the leader you are from the inside out, The Visibility Edit is where that shift begins. Head to elliesteinbrink.com to learn more and join the next round. Because the next version of you, she's not waiting for permission. She's waiting for you. Let's make it visible.