Why Smart Women Still Feel Behind With Money (And How to Stop Comparing)

Leah Hadley explains why many smart, high-achieving women still feel behind financially, emphasizing that it’s a predictable response to curated “highlight reels,” not a character flaw. She outlines three non-numeric drivers: being taught that wanting money is selfish, measuring progress against benchmarks that aren’t aligned with one’s values, and mistaking confidence for financial knowledge despite personal finance not being formally taught. Leah describes how comparison can cost real money by triggering reactive decisions, avoidance, and reluctance to seek help. She offers tools to break the cycle: define what “enough” means and quantify it, build a clear personal financial baseline (net worth, cash flow, protection, retirement, estate planning), audit financial inputs that create shame, and find honest community such as her Empowered Sisterhood. She also shares her career shift into finance and mentions her upcoming book.

Episode Transcript

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[00:00:00] Welcome to Intentional Money Moves Live. I'm Leah Hadley, and this episode was recorded live and is brought to you in audio form so you can take it with you wherever you go. Each week, I tackle the money topics that matter most to women who are ready to build wealth with purpose and confidence from investing and retirement planning to navigating finances through some of life's biggest transitions.

No topic is off the table. Now. Let's get into it.

Speaker: Hi there. I have a question for you. Have you ever looked at someone else's finances and thought, how are they so far ahead of me now, if that's you, drop an emoji in the chat. I wanna welcome you all back to Intentional Money Moves Live. I'm Leah Hadley. I am a financial planner. I'm a certified Divorce financial analyst.

But I'm also a woman who has had way too many [00:01:00] conversations with brilliant, accomplished women who still quietly wonder why they feel so far behind with money. So if you're joining me for the first time, welcome. I am so glad that you find your way here. Please say hello in the chat. Let me know where you're watching from.

I always like to know who's in the room, and if you are a regular, you know how it goes. This is a conversation, so please drop your questions, your reactions, your thoughts. I'll be watching the chat and certainly responding as I go. Welcome, thanks for being here. So today's topic, I wanna talk about something that I just don't think gets talked about enough.

And that is, why is it that there are so many smart, capable, high achieving women who have done everything right, but still walk around feeling behind when it comes to money? You've got a great career. You've made real money, you've [00:02:00] paid your bills, you've saved, and yet there's still this nagging feeling.

Like you should be further along. Like somehow you missed a memo, like everyone else has something figured out that you just haven't figured it out. Does that sound familiar to anybody who's watching? Hi Christine. Hi Jennifer. Thanks for being here. I'm sure that it does because honestly, I hear it constantly in my practice.

Today we're gonna talk about why this happens, what is really driving it, and most importantly. What to do about it. So let's dive in. So let's talk about this comparison trap, right? Why on earth do our brains do this? And here's the thing that I really want you to understand, okay? Feeling behind is not a character flaw.

It is not. Evidence. It's a feeling. It's not a sign that you've made bad decisions. It's [00:03:00] actually, believe it or not, a completely. Predictable response to the environment that we live in. Think about it, right? We are surrounded by the financial highlight reels of people's lives, right? If you looked at LinkedIn, it's full of people announcing their promotions or investments on Instagram.

I know I've been there with the renovated kitchen, right? Or maybe you see people on vacation or a yacht or even your friends, right? When you get together. You are not usually talking about debt or fear or money stress. You're talking about the kids' activities or the new car or the vacation you're planning, right?

So if you are feeling this, I want you to just recognize the fact that your brain is constantly consuming this curated version of other people's financial lives. And then you're comparing your entire picture, including all of the messy, behind the scenes stuff, you're comparing that to their [00:04:00] highlight reel.

And that's not even a fair comparison because it's not even a real comparison. But our brains don't know that. Okay, so here's something that I want you to sit with. You cannot compare your chapter three to somebody else's chapter 10, right? You don't know the full story. You don't know what they inherited.

You don't know what their spouse earns, what debt they're carrying, what decisions they made that they regret, right? You only see what's on the surface, and honestly, what's on the surface is generally not the full story. Okay?

So let's talk about three reasons why smart women often feel behind that actually don't have anything to do with money. Okay. And let's get specific, because in my work with women, both in terms of financial planning and in helping women to navigate divorce, I've really noticed three core reasons that have become a pattern of what I'm seeing and why people feel [00:05:00] behind.

And I wanna be clear. That none of these are actually about numbers at all. Okay, so reason number one, and I see this a lot, is that you are taught that wanting money is selfish. Anybody, does that resonate with anybody who's watching? And even if you're watching the replay, let me know you're watching the replay and go ahead and share in the chat that resonates with you.

You were taught that wanting money is selfish. How many of you grew up in a household where talking about money was uncomfortable? Where wanting something that felt nice, maybe felt greedy, right? Where being good with money actually was defined as spending as little as possible, right? A lot of women, especially women who identify as helpers, caregivers, really community oriented people were raised with a unconscious belief that wanting wealth is somehow in conflict with being a [00:06:00] good person.

It's actually very common. So what happens? You earn money. You feel vaguely guilty about wanting more. You don't track it closely because again, paying too much attention feels greedy. Maybe if you're in business for yourself, you're undercharging or you're not negotiating your salary, you because again, asking for more feels uncomfortable.

And then you look around and feel behind. Again, this is not because you were irresponsible, right? Not because you're irresponsible, but because you've been quietly sabotaging yourselves in these little ways based on a story that you may not have even realized that you were caring in some cases. Right?

Let me show you some of the comments that we're seeing here. So Jennifer says, yeah, she feels that way sometimes, especially when costs go up and they feel out of control.

Christine shared that they didn't talk much about money growing up. That's so common. That is so common Now. Reason number [00:07:00] two is that you are measuring against the wrong benchmarks. So here's a question that I really like to ask people ask, who told you what enough looks like? What does enough look like?

Most of us are measuring ourselves against these benchmarks. That were never actually ours to begin with. It might have been your college roommate's net worth or your neighbor's house, or some article that you read that said maybe that you're supposed to have three times your salary saved by the time you're 40 years old, right?

Those numbers were not designed with your life in mind. Those numbers were not designed with your life in mind, not with your values, your priorities, your definition. And freedom of freedom and of success, right? When you measure against a benchmark that doesn't belong to Yale, you're almost always gonna feel behind.[00:08:00]

You are, you're almost always going to feel behind because you're running somebody else's race on somebody else's track. And that really is the core of why I created the Intentional Money Method around values first, right? We talk about values before we get into the strategy, before we're talking about the action, before any of the tactical stuff.

Because if you don't know what you are building toward, you're gonna spend your whole life feeling. Like you're not enough, and that, quite frankly, that's exhausting, right? All right. Reason number three, you actually are equating confidence with knowledge and feeling like nobody taught you this stuff, right?

The third driver is something I see constantly, especially for women who are extremely accomplished in other areas of their life, right? You feel behind with money because you feel like you should know. More than you do, right? [00:09:00] Maybe have a graduate degree, you run a department, you raise children, you negotiated contracts, right?

You feel like a very capable individual. When you sit down with a financial statement and feel lost, the thought isn't, I haven't learned this yet. The thought is what's wrong with me? Nothing wrong with you, right? The thought is, why don't I understand this? But here's the truth. Personable finance is not intuitive.

It is a set of learned skills, and for most of us, especially for women, it was never formally taught, not in school, not at home. Most people were expected to figure it out on their own and feeling uncertain about investing or about tax strategy or state planning. That's not a sign of failure. It is a completely normal and rational response.

To never having been taught these things right. Now, here's the thing that I [00:10:00] really wanna be clear on, and I hope, like this is the message that I really I'm hoping that you'll walk away with today, right? And that is what comparison actually costs you. So I wanna spend a minute on something. I just don't think this get talk gets talked about enough and it really matters, right?

Comparison doesn't actually just feel uncomfortable or feel bad, okay? It actually costs you money. Like real tangible money in real ways, right? What am I talking about? When you feel behind, you are more likely to make reactive financial decisions. It's when you feel behind, you are more likely to make reactive financial decisions.

You see a friend talking about some new investment, and you jump in because you feel like you've been too conservative or you make a big purchase because you're trying to catch up to a lifestyle you think you should have. You avoid opening statements because looking at them makes the feeling worse, right?

When you feel behind. [00:11:00] You're actually less likely to ask for help because asking for help means admitting you don't know. And sometimes that feels like more evidence of what you are perceiving as a failure, right? And when you feel behind, you are almost never focused on what you actually have, right?

What you've built, the progress you've made, the decisions. That we're genuinely smart decisions, right? Comparison puts us in this chronic state of scarcity, right? Even when your actual numbers do not reflect that, okay? And from scarcity, you can't make those clear, intentional decisions. You really can only react.

So getting out of the comparison track, it's not just about feeling better. It's an actual financial strategy, if you can believe that or not. So how on earth do you stop comparing yourself to others? So let's talk about it because I'm not [00:12:00] here to just name the problem. I wanna give you some real tools, okay?

Strategy one is to define your, you are enough. What is enough for you? Now, some of you may have heard me talk about this before, but when I did this exercise for myself, I was actually shocked at what enough looked like for me. It was a much simpler, less I just didn't need to accumulate so much, right?

So before you can stop comparing yourself to somebody else's benchmark, you wanna get clear on what your is, and I want you to be very specific. Not I wanna be comfortable. I do want you to actually get to a real number that shows you what does a life that feels like enough for you? What does it actually cost?

Okay? So what does your ideal retirement actually look like? I was talking with a woman the other day who, she's lived a pretty stressful life. She's had a stressful career, Leah. In my retirement, all I want is peace. I want quiet. I want [00:13:00] ease. And so we looked at what does that mean in terms of where you live and how you live?

And how do we actually quantify what that looks like? Wanna think about how you wanna spend your time, right? What does an average month of expenses look like in that life? Then we can work backwards, right? Once we have the vision, the clarity, that North Star of what we really are working toward.

We can quantify that, right? So when you are tempted to compare yourself to somebody else, I want you to redirect and think, am I making progress toward my number, not theirs, mine, toward a life that feels fulfilling for me, right? You can't run toward somebody else's finish line. And also reach your own.

So get focused on what you want in celebrating what you have accomplished, right? Strategy number two is to build a personal financial baseline. One of the most powerful things you can do. Complete a [00:14:00] complete picture of exactly where you stand now, okay? Not where you think you stand. Real clarity on where you stand now.

What does your financial situation actually look like? What are your assets? What are your liabilities? It's gonna be your net worth statement. What does your cashflow look like? Money coming in, money going out. What kind of insurance protection do you have? How much are you saving for retirement?

What have you done in terms of your estate planning? A lot of women feel behind because they're comparing. Based on feelings and not facts. So when you see the actual numbers, one of two things can happen. Either you're gonna realize that you're further along than you thought you were, or you're gonna see exactly what needs to shift.

Both of these outcomes are a heck of a lot better than being in that sort of comparison thought fit so many of us find ourselves in, okay, clarity is always gonna be so much more valuable, right? [00:15:00] Strategy number three is to audit your financial inputs. And you've heard me talk about this a lot. It's a very practical strategy though, and even though it's so simple, it makes a big difference, right?

For one week, I want you to notice every single place that you are consuming somebody else's financial narrative. That might be Instagram. That might be LinkedIn. Maybe it's in conversations, maybe it's articles about what you should have saved. Okay? And I don't want you to cut it all out just to be clear.

I just want you to become aware of what you are taking in, right? And I want you to think about it. Does this inspire me or does it make me feel worse about where I am? What you're consuming, is it inspiring me? Is it motivating? Is it propelling you forward, or is it making you feel shame?

Information that consistently makes you feel worse? It is [00:16:00] just not serving you. No matter how helpful it is not serving you right. I know there are some big name gurus out there who like to shame people, and I personally cannot consume their content. Because I can't stand the way they talk to people.

If you are following some of these people and they're making you feel worse, right? Then you might wanna look at potentially making a change to your consumption, okay? It's not about bearing your head in the stand. It's about being intentional, which as you might know, my whole thing, right?

All right. Strategy number four is to find your people. Okay, now this one is underrated. One of the most powerful antidotes to comparison is community, but real community. Real community where people are honest about what they don't know. Where people are honest about where they're struggling, not just where they're winning, right?

[00:17:00] When you are surrounded by women who are working on the same things you are, who normalize the questions, who celebrate every single win, who don't make you feel stupid for asking questions, that comparison spiral will lose power. It'll lose power. You can't white knuckle your way out of comparison with willpower alone.

That's reality, right? You need a different kind of environment, one where honest conversation about money is the norm, right? It's actually a huge part of what we've built inside the Empowered Sisterhood. It's not just resources and workshops, although of course that stuff is incredibly valuable. But it's that community piece, right?

Women showing up and being real with each other about money in a way that most of us have never had permission to be. So it does change things. All right. Now I want to invite any of you who maybe [00:18:00] have been struggling with some comparison challenges. To put any questions in the chat, anything that might be on your mind, any reflections that you have, any of experiences that have felt like maybe obstacles to getting where you are or where you wanna be.

And I did just in preparation for this, this show in particular. 'cause I wasn't sure if people would feel comfortable putting their questions in the chat. So I talked to a few clients before I started this segment to get some questions from them that they would like to hear me answer. So I have those prepared for you.

And I'll go ahead to those in just a second, but I wanna give anybody who is watching live. An opportunity to ask any questions or reflections they may have. Now, I will also, for any of you watching the replay, I will always come back and look at the chat and respond to any questions or comments you may have at that time.

First question is, how do I stop feeling guilty about wanting to build real wealth? And this is such an important question, and honestly, I [00:19:00] talk about it with people all the time because there are a lot of people out there who really do struggle with this feeling, I have found that the best way to move through this or to work through this is to really get in connection, get in relationship with the impact that wealth can have.

Okay. Because a lot of times we're connecting it with ego, right? But when you get really clear. About what you wanna do with your wealth, what financial security means for yourself, for your family. The people you support, right? The causes that you care about, it really does stop being about greed. I have a whole section, a whole chapter in the book that's coming.

It should be coming out pretty soon, guys. I got it back to the publisher. I wanna say it was Saturday. I got it back to the publisher and that was the final round of edits. So it should be very soon. I'm very excited. But anyway, I lost my train of thought [00:20:00] 'cause I started talking about the book.

Oh. I was talking about how there's a whole chapter in the book about what it means to give with intention to think about. How do we give generously? But from a place that's in alignment with our values, so that way we really feel in alignment from a financial standpoint. It's a really powerful chapter.

So if you get a chance to take a look at the book, definitely it's not a book that you have to read like from cover to cover. It's one that you can kind skip around the chapters and still get a tremendous value value out of that. And I would definitely take a look at that particular chapter. If you are somebody who's really struggling with that guilt around wanting to build wealth, I think that'll be really valuable.

Christine says, thank you for what you said, because I felt shamed personally for being oh. What did I just do for being good at my career, but not good at my own personal finances? You are not alone. I hear it all the time. It's so common and where we have all the success, and I even share my story a lot of times I do podcast interviews and things, and people talk about you know how I got started in the [00:21:00] industry and that kind of thing. And before I got into financial services, I was a teacher. I have, my master's degree is in education and I was burnt out in the classroom and I started at this investment bank. And the first day that I walked into the investment bank, like I said, I had a master's degree.

I'd been teaching at the community college. I've been teaching the public schools. I felt like an educated individual. And I walk into this investment bank and I literally. Did not know what people were talking about. It felt like everybody around me was speaking a foreign language. It was all new to me.

I'd never taken a finance class. I'd never taken an accounting class, and I remember that so well. And here I was feeling like I had accomplished quite a bit in my career at that point. And then I just felt like a total fish outta water. Like I had no idea what I was doing, but I share that story often because I think, we seem to have this idea.

That money's intuitive, that we're supposed to just know how to manage it and build wealth, and it should be really simple. The reality is the actions that you take in order to build and create wealth. Are actually not very complicated, [00:22:00] but it's all of the other that goes into it, right?

It's getting clear about what we want and making sure we're progressing to the goals that are meaningful to us, right? Being in alignment with our values. So we really feel at our core that what we're doing is important, right? Being aware of that mindset that might be holding us back. It's so common.

It's very normal. All right. I'm in my fifties and I feel like I've started too late. Is it too late for me? All right, now you guys know if you've seen any of my videos, you've probably seen the one. 'cause I I was working with this gentleman, the wonderful videographer, but he had like a few funny a.

Hooks for me when I was reporting my video. So anyway, one of 'em is all about this specific topic that a friend of mine, Julie cii, wrote a book called 50 Not Finished, and really talking about how we're just getting started, right? Like we can do so much because we've had all of these experiences and now our minds are just different.

We're thinking different about opportunity. Our focus is different. There's just so [00:23:00] much that can be accomplished. So I'm gonna tell you, regardless of your starting point, regardless of your age. You are absolutely not too late, and you would be amazed at just getting clear, right? Getting clear on what matters to you, any of these messages, these stories, these mindsets that might be holding you back, and then just implementing and taking action on a strategy.

Having the right support in place. You would be amazed at how much wealth you can create and how quickly. All right. The last question. Are there any other questions in the chat here?

I have to put this on because it just, it made me laugh. So she this is Christie. She said, wait, are you saying that you went into investment banking as a second career, not knowing anything about it, and now you're teaching us about finance? My mind is blown. So this is 20 years later just walk in the door.

I was not an investment bank. I was actually in equity research. So equity research. Is the department within an investment bank that researches individual stocks for like [00:24:00] institutional investors. So making stock recommendations for like hedge fund managers, mutual fund managers, those kinds of folks.

And yeah, when I walked into that investment bank that very first day, it was just a temp job as an administrative assistant. It was in 2006, it was literally 20 years ago. And I just had some wonderful mentors. I was very fortunate, wonderful mentors who were really willing to support me, help me learn.

And ultimately in that, in that firm, I became a research associate, so I was actually supporting a senior analyst publishing research on stock opinions. And then I went to another firm, we were acquired and then I went to another firm and I became a senior equity research analyst publishing my own stock opinions and traveling around to meet with portfolio managers and whatnot.

And yes. And now I'm teaching you, but I've been working with individuals and families since 2012. So I've been doing this side of the business for quite some time now, and it's absolutely my passion and I think a lot of it is [00:25:00] because of where I started, that this was all completely and totally foreign to me.

So the last question I got was, what's the first real step to stop comparing. Start building. I really, truly cannot emphasize enough to you how valuable that exercise is of getting really clear about what you want your life to look like, what's important to you, and what does that really cost. I just, that was such a big deal to me when I went through that experience.

Now, mind you. I grew up in the Midwest, in a Ohio suburb of Cleveland. And when I think about what matters to me, what's important to me I didn't grow up in a flashy area. I didn't grow up with those kinds of inputs. And so that's really never been on my radar. So that, for me was a fortunate thing.

But I did go to college on the East Coast and did have some of the experiences and seeing, how other folks lived and very different from my own. When I was in equity research, I remember [00:26:00] when the bonuses were paid out. Everybody was getting like these new big fancy cars. That was always a big thing in that world, right?

But that wasn't important to me, right? When I got clear on what matters to me, I don't need a huge, fancy house. I definitely don't need a big. Costly fancy car. I love to travel. I love to spend time with my family and my friends. I love to do this work, right? And so creating a life that allows me to do this has been really meaningful for me.

And so that's what drives me. So when I think about what's my baseline. I'm looking at something that I've created for myself, right? My target is my own personal target. And if I leave you with nothing else today, that would be what I would encourage you is to come up with your own target and to really look at what would be meaningful to you?

What does that look like? Enough for you? Feeling behind with money, that feeling like, I should be further along is. Almost never an actual reflection of your financial situation, right? It's driven by the things that we talked about today, stories you were [00:27:00] taught about money and about worthiness, benchmarks that were never designed for your life, and that very normal discomfort of navigating a system that you just were never formally taught.

Okay? And the way out is not to just try harder. The way out is not to just try harder, it is to get intentional, right? Define your own enough. Build your own baseline, right? Pay attention to what you're consuming. Audit. Audit what you're consuming, and find community where honest conversation about money is the norm.

Okay? You're not behind. You're on your own path, and the goal is to make it as intentional as possible. And if today's topic resonated with you and you do wanna be part of a community who are doing this work together, who are getting real about money, building that clarity supporting each other through [00:28:00] those major life transitions, I do wanna invite you to take a look at the Empowered Sisterhood.

It is a membership community that is created specifically for women who are accomplished, who are capable, and still wondering why they don't feel even more confident. About their money, right? It's part education, it's part community, it's part accountability, and it's the environment where the comparison spiral just starts to lose its grip.

So I'll drop a link in the comments. If it's something you wanna explore further, please feel free to take a look at that. And then for those of you who keep asking about the book, I will just reiterate my new book, intentional Money in the Modern Women's Guide to Building Wealth, purpose and Peace.

We'll be coming in just a couple of weeks, so I will have more details very soon. But if you do wanna make sure that you're one of the first to note, make sure that you are on our email list so you don't miss the announcement. Again, I wanna thank you for [00:29:00] spending time with me this Tuesday, and I will see you next week.

Thanks for listening to Intentional Money Moves Live. If you enjoyed this episode, make sure to hit follow so you never miss one. Wanna join the conversation live? Tune in every Tuesday at noon Eastern time on YouTube. And if you're ready to take the next step in your financial journey, head over to watch her thrive.co.

To learn more about how my team and I can help you build wealth with purpose and peace of mind. I'll see you next week.