Why Your Style Loses Its Way During a Life Transition

You're in the middle of something big, and the ground feels like it's been swept out from underneath you. Maybe you left corporate to launch a business. Maybe you're stepping onto bigger stages. Maybe your body is changing, and nothing in your closet makes sense anymore. These are good things, or they're supposed to be. But when you're new to something, the confidence you used to rely on isn't where you left it.

And that's when you start looking outside yourself for it. What are other women in my industry wearing? What would make me look credible? What does my audience expect me to look like? It feels like grasping for certainty, because that's exactly what it is. The problem is it takes you further from yourself, not closer.

In this episode of The Visibility Shift, I'm talking about what happens to your relationship with style during a transition and why the instinct to reach for external rules and validation is so common, and so costly. I share what I've seen with clients, and my own version of this panic, and why your style can actually be a tool for rebuilding self-trust when everything else feels uncertain.

1:00 – Why transitions (even positive ones) feel like they’re killing your confidence

5:43 – The external referencing trap you might fall into during times of transition

7:56 – Examples of style rules that feel safe (but actually hold you back)

10:40 – The impact of urgency and panic shopping on your clarity and confidence

13:28 – How you might start grasping at external validation when in transition

18:09 – Style as an outside-in game reinforcing lack of self-trust and practical ways to build self-trust

21:53 – How I helped Julie start cultivating self-trust while transitioning into bigger speaking gigs

25:29 – Characteristics of women who’ve built self-trust and the importance of embracing your transition period

Mentioned In Why Your Style Loses Its Way During a Life Transition

Why Outfit Polls on Instagram Are Sneakily Eroding Your Self-Trust

Speaker Style Rules That Make You Forgettable (and What to Do Instead)

What Authentic Personal Branding Actually Looks Like

What Julie Brown Found When She Broke the Unwritten Speaker Style Rules

The Style Mindset Reset

Standout Style Kick-Starter

Work With Ellie

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Transcript

Ellie Steinbrink: 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. One thing I've really noticed, both in my own life and with my clients, is that being in transition, in any area of your life, is incredibly hard. And beyond that, I've come to understand that these times of transition can completely kill your self-trust and confidence, if you're not careful. This is true even when the transition is a great one, even when it's exciting, even when it's something you chose, like leaving corporate to start your new business, like getting a promotion, like stepping onto the biggest stage you've ever been on, like becoming more visible and a leader in your role. On paper, these are all really good things. But the reality is, whether we all like it or not, good or bad, the transition brings uncertainty. It can feel like the ground has been swept out from underneath you. Am I right? And suddenly you're trying to find firm footing again. And when you've been someone who is used to feeling confident, who has trusted herself, who knows how to make decisions, this feeling can be really unsettling. Like, what happened to me? That old confident version of me, where did she go? 

What I want to talk about in today's episode is how style becomes a part of the story for so many women's transition moments. And what I've seen is that style can be a tool that helps you build self-trust in those most uncertain moments, or it can be the very thing that erodes it. When I look back at my almost six years now of working as a stylist and running my own business, I realize that most of the women who come to me, are in some kind of transition. Examples might be they're leaving corporate to start their own business, or they're getting a promotion and now they're in a different level of leadership in their company. They might even be coming off of weight loss. They might be going to a new level in their career or in their business, like their business is expanding. They might be getting more visible, or booking bigger gigs, or going to bigger conferences, or speaking at bigger conferences. They might be even experiencing personal changes, like a divorce or experiencing body changes post-pregnancy, perimenopause, all of this. 

And what I notice isn't that they suddenly don't know how to dress, although that's often what they'll say to me, when we get on a call and start talking about why they're looking to work with me. Underneath all of this is really not just, I don't know what to wear, or I don't know how to dress for this new life that's in front of me. Underneath all of this is that they're grasping for certainty. Because when everything else feels uncertain in their life, when you're new at something, when you're not nailing it the way you used to, when you're not able just to grab the clothes that you've always grabbed, when you're making more mistakes maybe and falling down more, which is something also very common, when you're transitioning to something new. Or when you're dressing an entirely new, sometimes it feels like a foreign body, or when you're faced with bigger challenges, building your skills, expanding your mindset, expanding your capacity to do more things, you want something solid to grab onto. Then when you think about your style, style feels like, oh, something, it's something I can still hang onto and control. And it's why so many women have the urge to clean out their closet and start fresh in these transition moments. I mean, has this ever happened to you? Or notice that, you know, in transition times, you're searching for tips and resources on how to dress, or you go and get your colors done, or you start paying attention to how others in your new space, or your new industry, or whatever zone you're in, you start paying attention to how they're dressing. 

All of this feels safe and grounding. We just want something to feel safe, right? Because in a season when you might feel like you're failing more than usual, which is just part of being new to something, walking into a closet that also feels like a failure can just be a complete double whammy. Not only is life and work uncertain, now your closet doesn't feel like a place that you can rely on either, how frustrating. That's when everything starts to feel really overwhelming. So of course, we want to start reaching for certainty in our closet and that makes total sense. But here's the funny thing I've noticed and I've seen it enough times now to know that this is definitely a pattern of women who are in transition. When you are clinging to certainty, you often do it in ways that pull you farther away from yourself. You know, especially when it comes to what we're wearing and what we invest in with our clothes. Not because you're doing this intentionally, like you're not trying to, like you're not consciously doing this, but it's because ultimately you're looking for relief from this overwhelm and uncertainty. 

And one really common behavior I see happening, when we're grasping for this uncertainty in times of transition is external referencing, or something I often refer to as outside-in dressing. So what's happening with external referencing or this outside-in dressing is that we stop checking in with ourselves and start looking outside ourselves for this certainty and acceptance. So this sounds like, what are other women wearing at this event? Or what are other women in my industry wearing? What do other entrepreneurs wear, when they go and speak, or when they go to a conference, or when they go to networking events? What is my audience, if you're a speaker, what does my audience expect me to look like? Should I dress to their level? You know, it depends on who I'm speaking to. I hear women say, what looks professional, what's going to make me look credible and trustworthy, especially if you're starting your own business and now you feel all this pressure, where you want people to trust you and so you just want to get it right. I hear women say, I wear this because I get complimented on it. That's another way we external reference our style. Or what do my followers say I should wear or what looks best? Hello, raise your hand if you've ever done an Instagram poll and said, hey, I've got this big event coming up and tell me what to wear. Help me pick an outfit. 

In these ways, we're clinging for assurance that we're doing it right. Because our self-trust has taken a hit and we don't trust our own signal anymore. And this is also where I see a heavy reliance on style rules and not even style rules, but just rules about how we're supposed to show up in general. Because rules, again, feel certain, they feel comfortable, they feel grounding, when self-trust feels like it's been shaken. So some examples of rules I see women cling to is, like, black is the most professional. And this is especially true of the women I work with, who have come from a corporate environment and it's all they've ever known, because black and neutrals have been their world. And they're like, well, yes, when I start my business, I'm going to start dressing like this, because I'm certain this is how I will look the most professional. I hear women have rules like “don't stand out too much”. Even this comes from messaging from our childhood, where it's like as a woman or as a girl, it's not good to like to draw too much attention to yourself, maybe to be too loud and disruptive. So as a result, we choose clothes that make sure we don't stand out too much. 

Or as I mentioned before, if you're a speaker, you might put a heavy emphasis on dressing in a way that matches what your audience looks like. Or if you're, you know, you got a bunch of people. I had one client who works… who started speaking in the construction industry. And so she's like, I didn't want to be too dressed up, because they're there in their overalls and their work boots. I'll hear women talk about feeling like they need to put a blazer on, every time they record a video, or they stand on stage. And then I also hear a lot of like, I don't want to look too feminine, because I basically just want to look like a dude. And when I come from a space where there are a lot of men, I just kind of want to follow suit. 

If you've been here for a while, listening to me on this podcast, you know I talk a lot about rules. I could do an entire episode about rules and in fact, I have. So if you want me to talk more about rules, go check that out. But without even realizing it, rules about how we should or should not dress have been shoved down our throats for as long as we can remember, so much so that we aren't even conscious of all the ways in which we've had rules crammed down our throats. And slowly we stop listening to what feels good or true for us and we just assume that the rules will keep us on track and will keep us safe and will give us good outcomes and will make us successful and will make us look professional and credible. I mean it's no wonder we look at our closets and we don't like what we see because it's a mix of like borrowed strategies, appeasing others and rigid rules that are just not exciting and we don't connect with them. Rules are something we grasp, when we feel uncertain. 

Another thing that I see happen during times of transition, which is as if you've ever been in a time of transition, or sometimes I call it the messy middle. We all know it goes way slower than we want it to go, right? And urgency really feels the fire. There's always something on our calendar, right? Coming up that we need to be totally on point for. So whether that's, we've got a big conference we need to attend or we have booked a speaking engagement, or we have a brand photo shoot. Oh my gosh, talk about a panic moment. Or you have a trip that you need to pack for. I mean, I've had clients and I've been this person before too, who completely spirals before trips, because you're trying to figure out what am I supposed to wear? And I don't really know who I want to be and in my closet, it's a different version of me. And you know, it's just, it's so stressful. The reality is, when we feel urgency, we rush. Like I just need something that works right now, or I don't have time to figure this out, or I'll deal with this, like feeling aligned with myself later. I'll just default back to what has always worked. Urgency really gives you no space to think, to be thoughtful and intentional. And I don't know about you, but my clearest and best ideas have never come to me, when I was in a rush. So you just tend to default back to what has always worked, but it doesn't necessarily feel great. 

And then I think another interesting trend I've seen in times of transition, is using shopping to produce clarity. And I get it because it's like, oh, OK, I'm becoming a new version of myself and I'm getting on to bigger stages or whatever this transition is, or my body's literally changing. It makes… shopping makes us feel like we're being productive and it makes us feel like we're solving something. I've often said that when you are ready for a change, or when you're in the middle of a change and you know you're transitioning into a new version of yourself, avoid that temptation to shop. And here's why. The retail environment, whether you're in-store or online, is incredibly confusing, it's manipulative and it's designed to rush your decisions. It can throw you off track through sales, through fear of missing out, through people telling you what you should or shouldn't buy, or what's in or what's out. So while shopping can feel like a temporary win and most definitely it's a dopamine hit, isn't it? Sure has worked for me a time or two in the past. It can actually take you further away from trusting yourself. It can take you further away from clarity. And don't we all have closets to prove that more and more shopping doesn't bring you clarity? 

As I have gotten older and become more reflective, I've realized that much of my life relied on external sources to tell me I was okay or doing well. And if I'm being completely honest, it's not the most fun thing to admit out loud. But if you're a high achiever or a perfectionist type like me, I find this can easily be your story too. And when I think back to, especially during my working years, but also before that, when I was a teenager, what kept me afloat was achievements and wins and promotions and accolades, a steady paycheck even. So hello, those of you who are entrepreneurs, you understand what an affirmation it was to get a steady paycheck week after week. And when you're in transition, when everything can feel completely uncertain and unstable, a lot of those external validation pieces get stripped away, at least temporarily. 

So you start grasping for affirmation, which can come out in many ways. Like as an entrepreneur, it's come out for me by undervaluing my services to get a sale, by chasing after opportunities, or creating programs that sounded sexy, or marketing tactics that were sexy, but weren't aligned. But I want you to hear this, another area where we can grasp for affirmation is our clothes, because it can be a source of giving you a dopamine hit. They can help you look confident when you don't feel it inside and they can help you feel like you're doing it right, because you're looking around you and saying, well, that person who has already achieved, you know, has gone through the transition and is on the other side, boy, if I could just look like them, then I must be doing something right. It's also why sometimes we show up like extra flashy or extra bold or a little bit over-the-top, when we feel uncomfortable inside. It's this like grasp for I just want to prove that I'm doing this, right? I want to get a compliment, I want someone to notice that I'm just… I'm doing something right, even if it's not quite aligned right now, I just want that. And we don't do this manipulatively. 

I'm not saying that in fact I saw this in myself recently, in the past year, when I had an event to attend, where I knew there were going to be other female entrepreneurs that were at the next level, the level that I was looking to achieve. And because I wasn't yet at the level of those women I knew I'd be in the same room with, I hit the panic button, when I started to think about what am I going to wear? And so I started shopping for outfits that would help me feel more secure in these rooms, help me feel like I fit in. And somewhere in the middle of the mess and the chaos of packages at my house and last minute shopping and returns and my mind was spinning and nothing felt right. I caught myself and realized this isn't a very honest version of myself that I'm crafting at this moment. It's because I'm so worried about looking like this next version of myself that I've lost sight of who is actually the true Ellie here. 

I realized I was trying to create more certainty and assurance and fake confidence through my outfit instead of building self-trust. And thank God, in the middle of this chaos, before the event, I came to my senses and I ended up choosing something that actually reflected who I am. It wasn't a version that I knew would work in this group of women, it was me. It was bold, it was playful, it was colorful. And I'm so glad I did, because I felt so comfortable at that event. And it reminded me that I can trust myself in my decisions about what feels right for me, what's true for me. And if I'm being honest, any time in my journey as an entrepreneur where I leaned on my own intuition instead of following other, or what some expert said, the results were always better. 

The thing I'd love to zone in on in today's conversation isn't just about how awful transitions can feel. Trust me, that is an episode in itself. But I want to talk about what is happening to you, in the process of transition and how you have a choice that either this transition can erode your self-trust, or it can embolden it. And style is absolutely a part of this conversation. What I know to be true, from my own personal experience and working now with hundreds of women, is that style, for as long as I've known it, is largely an outside-in game. Meaning we have traditionally been taught to use external sources to define our success. We use style as a tool to manage perceptions of others. There's a whole psychology around what to wear to get the right perceptions from others. We use it to communicate something specific. We outsource our authority to others, thinking they know better. We borrow confidence when we copy someone else's look, instead of building it for ourselves. We use compliments to decide what is in or what is out in our closet. 

And underneath all of this outside-in approach to style, we reinforce a lack of trust in ourselves, because dressing in a way that someone else defines, is more trustworthy, at least that's what we say and it can guarantee our success, right? That's what we tell ourselves. But what if we thought of style as a way not just to get dressed, or to impress others, or to get a certain perception from others, but what if we used style as a way to cultivate self-trust, especially during these times of transition? You might be thinking, well, how would I do that? Well, a few ways you can build self-trust through your style is when you ask yourself first, what you like and give an honest answer that isn't tied up in what you think you should do. You can build self-trust when you get curious about why you're following certain rules and for whose benefit. And if this is something you want to dive into a little bit more, I have a guide, called “The Style Mindset Reset”, it’ll be linked in the notes. This is actually a little  snippet of what I do with my clients, but it helps you identify all the different rules you are following, when it comes to deciding how to dress, what you think is okay to wear or not wear, what is okay, how it is okay to be as a woman. And I'm just going to warn you that when you do this exercise, it's alarming how many rules conscious or unconscious that we follow, when it comes to how we get dressed and the decisions we make around what stays and grows in our closet. So go check that out, that'll be linked in the show notes. It's called “The Style Mindset Reset”. 

Another way you can build self-trust through style is when you stop letting compliments drive every decision, or asking, if you're an entrepreneur and you're on socials and you start asking your audience to decide which outfit should I wear? Self-trust is reinforced, when your clothes reflect who you truly are. So if you listen to my personal branding series, that was what that was all about, authenticity. Instead of letting your clothes become a costume, or some kind of a performative act… And this is why in my signature standout style Kickstarter program, I bake in exercises that help you tune back into yourself, because we live in a world and every woman that I know has been taught that we dress from the outside in. So it's designed, this program is designed, to remove any of that outside messaging or rules, or at least help us become aware of it, that clutter up your decision making and help you get closer to who you truly are. And giving you the courage to actually start dressing in a way that's more aligned with who you are. 

I saw a cultivation of self-trust, one of the… I see it with all of my clients, but I want to talk about my client, Julie, who was actually just here on the podcast recently. We talked in our interview about how when she first started speaking and as a side note, she had left a corporate career in the construction industry and left to become a keynote speaker and where she started speaking was, you know, in the construction industry. And now she's a fully booked keynote speaker and she speaks to all sorts of audiences, but she had said in her interview that when she first started she was like, okay, you know like, what do you got to do to be a keynote speaker and what are you supposed to wear? And so she started looking around and getting a sense of however, what everyone's style was. She noticed that a lot of other speakers were picking a signature piece that was part of their quote unquote uniform. And she picked up on all sorts of other rules that are very specific to the speaking industry, like ridiculous ones, where you're not supposed to wear open toed shoes. But also practical ones, like whatever you wear has to have, you know, a mic, a place where your mic can clip into it and you can't wear too big jewelry, because that might mess with the audio. 

So she was already quickly gathering all these different expectations and rules that was then defining what her style was going to be and she also said that she felt this incredible pressure to downplay her femininity, as she started out… long ago, when she started out, she had said most of the speakers out there, at least the really successful ones, were men. And so this was a way she wanted to establish her credibility as like, hey, if I just show up like a dude, you know, then that'll improve my chances. But when we started doing this work together in the standout style Kickstarter program, she was in another transition, because at this point she was already an established speaker. And now she was starting to book much bigger stages with bigger audiences. And in our initial conversations, instead of letting her default to what she saw others in her space doing, or default to rules that existed in the speaking realm, we got curious about what she liked.

We talked about what style would enhance this powerful, bold, energetic brand that she had already created and established for herself. And as a result, in a transition work, she could have just easily pressed even harder into what was the right or expected thing to do. She got brave, she paved her own path. She trusted that what she loved, she could wear and learned that wearing those things didn't create negative attention, like I think we convince ourselves they will, but plenty of positive attention. She really did take some big risks in her clothes, but it was also taking a risk on herself. And that is what paid off. Honestly, when she decided to ask for style help, she probably figured she would just get help buying some clothes, right? But honestly, she didn't realize that this was more than just clothes, she was building self-trust. And this was coming from a woman who already had plenty of confidence. What I'm saying with Julie's example is that the clothes aren't necessarily the point. Who you become in the process is the point.

You can always tell when a woman has done this work, can't you? This work of cultivating self-trust during transitions, where they come out stronger. I know you've seen them. You've seen them at networking events, you've seen them on stage, you've seen them in workplaces. They're the ones where they are so trusting in themselves and confident, it literally oozes out of them. It's a completely different energy, we feel it and it isn't always loud, but it's noticeable. It's that grounded energy of like, I'm done playing the game. I'm done trying to be somebody else. This is who I am. I'm trusting that's enough. What I'm learning as I experience transition myself and as I work with clients that are going through a transition, you don't get there, quote unquote there, meaning to this unshakable confident place that we're all hoping to get to. Without the transition, it's not possible to just like skip over the transition. You don't get there without the messy middle. And I think we can all agree that the messy middle totally sucks and we just wish it could be rushed along. We wish we could just like go without and then get to the new shiny version. 

I can say this because I am in the middle of a giant messy middle right now, where I can completely empathize with how vulnerable it feels to show up, when you don't feel like the transition is complete. Where maybe you're not as shiny or polished as you hope or envision the final outcome will be. And what I've experienced is that there is a great temptation to want to hide, in these moments, to want to just wait it out, to fake it and not let anyone see the transition is happening. But I know that's the very thing that would hold me back. And if this is you I'm talking to now, through a transition, through a messy middle, hiding or faking or not pretending that you're going through it will hold you back too. I've come to believe and have had to retrain my brain that it's not about waiting until the shiny new version is ready and then all of a sudden you will be confident, you will trust yourself, you'll… that version of yourself you knew once will come back. 

Self-trust is actually built in small consistent moments. When you choose to show up honestly instead of perfectly. And let me tell you as a perfectionist this is incredibly hard to do. So if you're in transition and second-guessing yourself right now, I want you to know you're exactly where you need to be. All you have to do is accept it. I think it's all too easy to want to hate it, because it's messy, it's unclear, but every day I'm learning it's a phase to embrace. Because this transition isn't really here to take you down, unless you allow it. This transition is here to rebuild you from the inside out. It's here to strengthen you and let your style be a part of this story, where instead of defaulting to what would be easier, or what would garner instant attention or praise. 

What if style was a way in which you could come back to yourself and trust that you know what's best? When you can flex this muscle of self-trust, even in your wardrobe, you won't believe how powerful it can make you feel. No amount of pretending can ever give you this feeling. And you'll wonder why you ever wanted to dress in any other way. 

While I'm aware this episode wasn't heavy on how-tos or giving you tips on what to do next, it was really meant to help you see yourself and reframe what this transition can look like for you. And if you're in a transition, moving to the next level, going on bigger stages, whatever that transition looks like for you and you want some support, I want to let you know that my Standout Style Kickstarter program is now open for booking for summer and fall. 

This is a place where you will absolutely develop your own unique and distinctive style, which is so important as a personal brand, by the way. And all of that starts with having self-trust. And so this program is filled with coaching, mindset, training and learning that help you switch that mindset from outside-in dressing to inside-out dressing. This was a program I built very intentionally to help you make changes in your closet that will actually last. 

So if you're interested, check out the link in the show notes to learn more. You can always book a call with me to discuss more about the program and how to get started. And with that, I want to say, if you're in transition, if you're realizing that you are experiencing a lot of self-doubt, know that's completely normal. In fact, I'm in this with you. A lot of women are in this with you. Be encouraged that while it feels slow, painfully slow, maybe that's because great things never come easy. So I'm sending all my love and I will 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. 

Let's make it visible.