The Achievement Trap: Why Success Never Feels Like Enough

Have you ever reached a goal you worked incredibly hard for…only to immediately start thinking about the next one?

If that sounds familiar, you’re not alone.

So many ambitious women spend their lives chasing achievement, believing confidence will finally arrive after the next promotion, the next milestone, the next accomplishment. But what if confidence isn’t built at the finish line?

In this episode, we’re exploring why high-achieving women often struggle to celebrate themselves, how our worth becomes tied to external validation, and why learning to recognize your progress may be one of the most powerful mindset shifts you can make.

We share personal stories about the moments we almost missed because we were so focused on what still wasn’t going well—and why building quiet, internal confidence changes everything.

If you’ve ever felt like success still isn’t enough, this conversation is for you.

In this episode, we discuss:

• Why confidence built on external validation will always leave you wanting more.
• The “achievement trap” that keeps high achievers constantly moving the goalposts.
• Why celebrating small wins isn’t selfish—it’s essential.
• How resilience and confidence grow together.
• Recognizing the difference between performative confidence and quiet confidence.
• Why criticism hurts most when it touches an existing fear.
• Learning to receive compliments without minimizing yourself.
• How appreciating who you’ve already become makes the journey far more joyful.

Remember: becoming your next-level self doesn’t mean overlooking the woman who got you here.

If this episode resonated with you, we’d love for you to subscribe, leave a review, and share it with a woman who needs the reminder that she is already becoming someone incredible.

© The Lipstick Alchemists. This material may be protected by copyright and is used for reference and attribution purposes only.

If this message resonated with you, subscribe to The Lipstick Alchemists and share it with a friend who’s ready for more alignment, courage, and sparkle in her life.

Transcript

SPEAKER_00 0:00

Welcome to the Lipstick Alchemist, the podcast for ambitious women ready to stop playing it safe and start living in alignment. We'll explore the mindset shifts, the soul nudges, and awaken the version of you you were always meant to be.

SPEAKER_01 0:14

Alright, so we're back and ha on another episode. We're having so much fun filming these podcasts. And a lot of the questions that we get when we um kind of play back our journey or try to give snippets are kind of um where to start. And I think we've addressed this in other podcasts, but we find for a lot of women, and I know I fell into this category, I would say you two really struggle with just confidence. Some of the most talented women ever, I think, really struggle with the self, you know, congratulating themselves and building the confidence. And this is a muscle that I think a lot of women need to exercise in tiny little bits so that they can sort of build their confidence and their resilience. They go side by side. And the more confident and resilient you are, the more likely you are to uh take a risk that's big and feels important.

SPEAKER_00 1:05

Yeah, well, and I think as when we're younger, I feel like a lot of girls and women, we even as we're growing careers and different things, you're getting your confidence from external things. So it's shaped, your confidence is shaped by compliments you get or achieving different things. And um, and then I think we get to this point where we're at, whereas you're starting to evolve and wanting to step into the next level of yourself or the the next next level, um, you realize that it has to become so much more than that.

SPEAKER_01 1:38

I think that, and and I think the only way to build it in a way that feels authentic and not braggy or because I think a lot of people associate those two is you know, confident people are bitchy or egotistical. And a lot, I think a lot of us assign values to confidence, but uh, you always know the difference between I think an an internally confident person and one that is constantly seeking external validation. And I'm always working on building mine, but um, I think I'll I'll use myself as an example, and I think a lot of young women are this way. Um, you're a lot of my confidence was around appearance for a long time, wanting to be somebody who, you know, felt put together, looked polished, um, was fit. And if there was any feedback that I was off of where I knew I needed to be, it would send me into a tailspin. So imagine what a losing game that is at 47 when a lot of your value is based on your only your looks. And I think as women age, you do see um, you know, that flipping of the script and and the need to build tools that are internal and aren't performance-based or physical, which I think a lot of women do, you know, uh derive a lot of confidence from their physical ability or physical looks, who wouldn't? But when those things start to fall away or the affirmation starts to fall away, it can leave you a lot of times in a low self-esteem place. And it's really hard to step into your next chapter if you're playing a losing game.

SPEAKER_00 3:11

Yeah, I mean, I couldn't agree more. And I think as you and I have sort of had these realizations, especially me, as I brought them to you in the last couple weeks, I think what we've seen along with that is we've focused a ton on us stepping into our next level and trying to help women do the same. And so, with that, is figuring out who you want to become, figuring out who you are now. What are the the limiting beliefs? What's holding you back from there? But I think um what's interesting is and ties back to the confidence piece is at the same time, are we, and I would challenge, I would ask this to our women listeners, are you taking the time to appreciate and acknowledge who you've already become and how far you've come in the achievements that you have accomplished on your way to doing more and becoming more?

SPEAKER_01 4:01

I I think that's a big such an important thing that people miss is let's say you have a vision for your life that is, you know, far in the reaches, and you're so focused on becoming that person that you really fail to acknowledge every little baby step um along the way. And that does two things that I think are really sad. Number one, it it makes you feel like you can only have joy and happiness and confidence at the end of the journey. And I think for many people, they realize the journey was um the best part about it, and they get to that pinnacle and they're like, oh, well, yeah, this is a fucking nice view. Now I gotta climb another, you know, Appalachian Mountain. But I think, and I think that's why engineering small wins and really affirming yourself, celebrating tiny things, it seems sort of rudimentary, but without that, you really are missing all of the gajillion good choices that go into building life your dreams. And the fact is, if you've not, if you've not acknowledged and celebrated those things, it's hard to build confidence and reaffirm yourself. And then the jump from here to where I'm going feels a lot more steep because I haven't uh grown the confidence inside of my own belief in my abilities.

SPEAKER_00 5:16

Yes, it's like a true achievement trap where we're just like you check the box and you're on to the next. So I lost weight. Okay, but I have 10 more to lose. Or I got the promotion. Are you talking to is this about me?

SPEAKER_01 5:29

Is this about me and my FUPA? Because I hear your feedback and we're doing an episode on that next. So just save your comments till then, please.

SPEAKER_00 5:37

Fupa, I haven't heard that term in forever. Don't make me show you what it means. Don't make me show. Then we maybe aren't as good of friends as now I lost my train, well. Um, or like you uh achieve a promotion, but you're like, okay, great, you checked it off. Now we're on to the the next thing. And I think high achieving women really run this risk of completely burning yourself out because you you are setting goals and you're setting really big goals and you're dreaming really big. But I just think we cannot, we cannot forget to acknowledge who we're becoming. And I think you and I both, we've talked about even today of how imagine just our the self if we were looking at ourself and taught having a conversation with ourselves from five years ago. Like, can you even imagine being where you are today? Like if you were that person, like I know for me, it's like, oh, like mind-blowing the things that I've accomplished. But I think in the day-to-day life, I certainly don't give myself enough credit for those things.

SPEAKER_01 6:38

I agree. And I think when we were talking about that at the at the office today and reflecting on it, it does make you kind of uh, I mean, you're proud, but then I think you're also a little sad because you um when you when you don't celebrate those tiny achievements, you really are in a constant state of achieving the next, achieving the next, achieving the next. And it's it's a never-ending and no way to win the game when you're always moving those hurdles on yourself. And and that's about the you know, that's the journey of life is deciding which way you're going. But I think without really having people around you that can celebrate with you, having your I for example, I went to the gym twice so far this week.

SPEAKER_00 7:20

Hey, amazing.

SPEAKER_01 7:22

Nobody be blinded by my abs. And this is twice in about five years. So that and it sounds so silly and so little, but I want to get for you.

SPEAKER_00 7:36

I knew that was the big deal.

SPEAKER_01 7:38

Uh wait on the strange bikini to be my Friday attire of coming soon by third class. But it was, but I think because I uh don't, you know, that's a place where I need to build some um, well, some muscles, literally. But I think having those tiny accomplishments, as silly as they are, even if you have, if you celebrate them yourself, you feel a little bit proud every day. And isn't that better till waiting till you step on the scale and you have your dream weight? And then you're like, okay, well, now I need the next thing. It's really the it's fun to celebrate and it's affirming to celebrate. And when you tell yourself, like, I I have my two times done, I might be done till next year, but I had two this year. Um, you are setting yourself up to want to continue that behavior.

SPEAKER_00 8:26

Well, and otherwise you're never, you're never gonna feel like you're enough. And so it goes back to again, if we as little girls tied our value and our worth to achievement and to what others thought of us, then it's a rude awakening when we're finding ourselves doing that same thing in midlife, you know, and it's like then you're trying to prove yourself. And so I think I have to ask myself, like, am I not celebrating because I'm trying to just achieve more because that's where I find my value and my worth in what others are others seeing me do that. And I don't think that's the case, but I think it's just interesting that we we do run that risk.

SPEAKER_01 9:05

Why do you think women struggle to really stop and celebrate? Like, why do you think that's hard for us in general and and you know, for you, speak for yourself.

SPEAKER_00 9:16

You know, I think I think for a few reasons. I think it's kind of what I was just saying around where we maybe hold our value. I think sometimes you're scared to talk about it with other people. So you have these goals, maybe you don't have the right community or friends around you that are um gonna cheer you on. And so you're not out there like talking to people like, hey, this is a big goal I'm going for. But if you just had that group to like celebrate with you, that could be a big win. Uh, and I think for if I think about myself, I think I've had times where people have judged me. And I had can think of, you know, um, a former close friend of mine who knew me my whole life and said, um, in a kind of argument we had, a comment was made on something along the lines of how I you just hold yourself in such a high regard. And it was not a compliment. And so to be sound like 40 fucking four years old and be faced now with like my questioning my worth again because someone that I've known forever and who I thought loved me and celebrated me is now more instead looking at me and saying that I'm almost like too cocky. And so then I think that in these situations where I do want to celebrate, I find myself maybe holding myself back a little bit because those little memories pop in every now and again. And I think I'm a lot better at um moving forward. And you and I talked about how in the past it was like if someone gave me feedback or someone gave me something that would throw myself, throw us, throw me, throw me off, it could take forever to for me to recover. And now, now it doesn't. But I think we're we're crazy if we don't think that those little comments that hurt your feelings don't pop back every now and again.

SPEAKER_01 11:02

I think that for sure, and I think the more painful they are, or the more um like strong your reaction is, that is a signal to say, oh, this is something that I actually think could be true. Yeah. Because I think when someone says something to you where you're like, that's not fucking true. Like I nice compliment on or insult on my FUPA. I know that I have one, so fuck off. It's really like when someone says something that you fear deep down is something that you are afraid of. And when you have those triggers, that is again a sign to say, this is something you need to work on, and you have to take them out of your little backpack of shit that I need to fix. I carried mine right here, and really examine like, you know, is this true? What do I need to work on in myself so that when I get an insult or a back-handed comment comp comment or you know, uh something that hurts my feelings, those are so much more about our deepest fears than it is about um, you know, someone giving you a real burn on the playground.

SPEAKER_00 12:04

Yeah. What do you what do you think? Why do you think women or why have how have you found yourself not maybe taking the time to celebrate things? Because I feel like you are you are the epitome of a high achiever and you've been accomplishing incredible things in your journey lately. Um, I'm just curious what's been your experience?

SPEAKER_01 12:21

You know what? I think I was thinking about that a lot today, and I think it's um one the community of people you have around you. So do you have people that you're you know really hold you up and know your journey and have seen the ups and downs and are celebrating you, or or if and if you're afraid to to celebrate with them, that's a no. Um but I think for me, yeah, the hardest thing about celebrating was you because my life always goes in like it's really a teeter-totter. So, and this is I think we're where I always, you know, maybe it's an achievement side, but typically if my professional life is on fire, my personal life is shit. If my personal life and professional life are good, I'm not as healthy as I need to be. If I'm as doing those three, which in I'd also ride my unicorn to work because I don't think I've ever, but because I think you're always balancing each part of your life, yeah, it's oftentimes like you're high-fiving yourself on an amazing accomplishment at work, and you're like, but that really has taken from time with my kids this month. So it's not even that you like every accomplishment in your mind or in my mind, and I think this goes back to you know, wanting to be good at at everything when I'm a solid C across the board, but it really is, you know, thinking of your life as if I have this, then I don't have that. If I have that, then I don't have this. And it's it always for me highlights a big success, always highlights not um downplaying that success, but the things that are not at that level. And it immediately creates shame for me to be like, oh, so I, you know, had a a great month, but I, you know, can't, I'm using it to eat McDonald's and feed my Big Mac habit. Um, and then I go on to that goal of trying to, and then of course my business um goes up or down. So it's really deciding what is important to you and celebrating tiny wins in whatever categories those are.

SPEAKER_00 14:17

Yeah, well, and that exact thing happened to me in the last couple weeks. It was like a goal I in my business I was working really hard towards, and I finally achieved it, but and but also in my business, not even on in my personal life, there were other things that I didn't feel like I was crushing it at, and the results showed. And I really struggled with celebrating something that I had literally had as a goal for years. I see. And it was such a shame. Like, so now that I look back, I'm like, what a moment that I missed. And thank God for you. And this goes back to the community because you didn't let you didn't stop that or you stopped that from happening. You were like, no, and you know, got me flowers and wrote the sweetest little note and um and like brought helped bring me back, but I still had those moments of like, oh, but and that all I did was want to focus on what wasn't working instead of what was.

SPEAKER_01 15:09

I remember that because it was very recent, and I remember that being the, you know, a big goal for a long time. And I I did feel um, you know, we I think we've had celebrations where we're like, yes, we're jumping up and down and we're and then this one was so big um in both of our minds, it was really counterintuitive to see. I know you were happy and proud of yourself. I was busting with pride, but I did feel for such a high achievement that the joy around it, and I think, and that was really the inspiration for this podcast, is to say, you know, this would have been again five years ago, it would have been mind-blowing. And it took so much work and so much care for the people you work with every day. So it it felt it hurt me when I saw that it wasn't landing on, and sometimes maybe you don't even realize, but when you see somebody that you're so proud of and they're really struggling to sit in that joy for more than a minute, it's and I've been that person too, it sh reflects back on you that you have to get to a place where you know you really almost force yourself to feel joy and like it's so joyful when I force myself to do things. I feel such joy when I really dig in and force myself.

SPEAKER_00 16:28

No, I'm gonna manhandle you and just having joy. I can because I can think of when I had our um book signing and I remember it kind of felt at the time, you know, like a big event that you've you've been planning and you're a part of, like a wedding, for example, where you're just going about the whole time and it goes so fast and you're talking to everybody and it's so fun, but like it's really hard to be in the moment and be present. And so I do remember I didn't go home and force myself to have joy, but I intentionally was like, I got home and I'm like, I need to go in a quiet room and just process everything that just happened because this was like such a big moment and I almost missed it. And I literally just started like bawling like a freaking baby because I was so had so much gratitude for everything that had just happened. Um, but I again almost missed it and just like ran on to okay, well, what's the next thing? Yay! I said like did a book and I just had a signing, like, and so it's just funny. But um, so I have two two examples within almost the same week where I did it and I didn't. And that's obviously the evolution of us growing into the next version of ourselves. But I just think um, I just know people so many people out there are doing that exact thing.

SPEAKER_01 17:37

I I think a million percent. And I think we always think of celebration, you know, for a celebration, it needs to be something giant. But I, as you were doing your your book, I remember like looking over what you had written, passing it, and like really getting joy from sharing your story, like sharing your story, hearing how it was impacting. So I think you those were smaller goals before the book signing, where you and a good example of where you're appreciating the journey of saying, like, wow, writing this really brings me joy. Seeing my good girlfriend read it and be like, those were like tiny, tiny little nibbles along what was a pretty long process of connecting with your joy. And I think it was, if I think back to Fat Me, it's almost like the food, you know, not the food, not the current, the less, the more fat, but like, you know, when you're over, when you're let's say a hundred and pounds large, and you, you know, you look at how far you have to go and you're trying to get to that. I think it's really feeling joy for those tiny accomplishments that you have along the way, even when the journey seems long. And uh, you know, that's where people get discouraged, or because they because they see the end goal and it feels like it's insurmountable when really if they were just taking a minute to be like, uh, two pounds hot damn. I'm gonna celebrate with a snack. I know, you know, I my ass would already be in booty shorts and a and something inappropriate with two pound. But I think it though that's a I think a relatable example, and maybe I think even if we continue on with the weight example, which is so relatable, it is, you know, those tiny celebrations are I think a big key to staying on track and enjoying the journey versus being like I've got to lose another fucking 20. And all you think is fucking 20. And then you lose it and you're like, that's it. Now, yeah. And it was such a gritty process because you made it into something that you could only celebrate when you got there. And then you're for me, I'm like, oh, I'm still size 12 anyway.

SPEAKER_00 19:42

Well, and then yeah, and then you're already on to the again, the next thing, and like, but it does that, like that's just crappy to think that you if we keep doing that now, we're gonna do it forever. And then, like you said, you find yourself at the crossroads of the next life, and you're like, man, is this really what how I approached it all?

SPEAKER_01 20:01

What do you notice? Because I know we talk about, and I I see you see things like so well in reverse, and I wish I had a time machine to fix a lot of the stupid shit I've done. But I think now I really can recognize someone who is internally competent in and the and someone who pretends to be competent. And I think it's that I I'm trying to figure out a way to express it, but I know for me, a lot of times when I was pretending to be confident, I was the loudest person in the room. I'm the one um, you know, I could be in a room full of, you know, top professional players or people that I should be listening to. And it's so important to me to feed myself for it that I'm talking more than listening.

SPEAKER_00 20:45

How stupid is that?

SPEAKER_01 20:47

And I think the more I I evolved, I noticed that the people who are really like achieving on high levels are they have a quiet confidence. They're um, they don't need always the center spotlight. They're not pretending to be something they're not, and they just exist there. And I think for all of us, we need to find women um who uh are in that place and we need to leverage them and have them help us celebrate those tiny wins and build, you know, help us build confidence and get feedback from them and and really use our network.

SPEAKER_00 21:24

I I you brought up a great example, and I also thought about another another easy test is on whether or not you can take compliments because I think super confident people um they they accept it. They because they they believe it and they say like I accept that and they like thank you, and not oh thank you, but I still have 20 more pounds to lose or oh this'll and I think I think we can find it funny sometimes to be self-deprecating to bring humor to it. Um, but sometimes you have to make sure that underneath it all isn't again a worthiness, a lack of confidence thing that you're just trying to brush, brush off. But I think if you can really take a compliment, it's a good step. I'm still working on that one.

SPEAKER_01 22:07

I same. I noticed we both have those same behaviors, and it is, I mean, I think we'll just wrap up the episode. I think in in talking about that, which is if you can find even one or two, um, I always pick girlfriends, but it could be your husband, it could be your wife, could be your sister, your kid, people who really care about you and can help you, you know, people that you're not afraid to say your tiny goals to out loud and that can help you celebrate. I think it's it's something that seems so small, but it could be a difference maker between how much you're willing to grow. And uh, you know, it's so much about a community and not hiding even your tiniest baby two days a week gym achievement from people who you know will cheer you on as tiny and pathetic as the goal is.

SPEAKER_00 22:54

And if you don't have it, we want to be your girls because we every woman deserves that. And I think we all grow together, we grow better together when we've got women in our corner. We've got enough shit around us to like to deal with, like, we need to be cheering each other on. So make sure to let us know if we can we can help you and share, even share this episode. If you find a woman, if you know someone, um, is that person for you, like send them this episode and said, Here's what they talked about. Like, I'd love for you to listen and know that, like, I'm grateful that I have you. Um, or maybe to ask somebody, like, hey, would you? I don't have this person, and but I really admire you and I honor you, and I'd love for you to be that person. And so we'd love for you to spread the word, help us spread the word on our podcast too. So I love that.

SPEAKER_01 23:42

Thank you guys all for listening, and we'll see you next time.

SPEAKER_00 23:45

Yay!