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Navigating Self-Acceptance With Jen Liddy


Meet Jen Liddy, a seasoned entrepreneur who discovered the ins and outs of business through her own trials. Now, as a business development coach, she guides women entrepreneurs away from the pitfalls, helping them thrive without a one-size-fits-all strategy.

In this episode, we reflect on Jen's past as she discusses waking up unhappy with her body, fixated on a specific size. Those "shoulds" consumed energy, from body image to post-meeting self-critique. Despite projecting confidence, she too grappled with self-doubt and second-guessing - a constant companion in our decisions.

Although those nagging doubts persist today, Jen has found them to be quieter. The journey isn't about eradicating "shoulds" entirely but learning to soften their noise as we navigate this path to self-acceptance.

Join me as we listen to Jen's journey, discussing entrepreneurship, self-assurance, and embracing our evolving selves. To connect with Jen, visit her website 


Watch Jen's Story



Jennifer: Welcome to the I Don’t Give a Should Show – a podcast exploring ALL the ways that women SHOULD all over themselves. How many times do you find yourself acting out of obligation or doing what everyone ELSE expects from you without stopping to consider why? Where do all those beliefs that are driving you come from? If you’re tired of feeling resentful, overwhelmed, stuck, exhausted or pissed off you’re in the right place.

Shoulding all over yourself is a real thing, but it doesn’t have to be in the driver’s seat.

I’m your host Jen Sherwood, and I spent waaaaay too many years trying to prove that I was good enough and worrying what other people thought while avoiding conflict at all costs. Today, I don’t give a should – well not as many anyway and neither should you. I’m talking to women like you who figured out how to stop shoulding and start LIVING.

Today, my guest is Jen Liddy – I'm so excited to have Jen here with us. After learning how to be an entrepreneur from the inside out, you know, by trial and error, Jen Liddy decided to help women entrepreneurs avoid the pitfalls and frustrations that keep them from making money in their business. 

Her expertise as a business development coach helps women save time and energy and make more money with systems and clarity that reduce chaos and increase client flow. Without a one size fits all strategy. 

I'm so happy she's here and I have to tell you, this is so fun. Jen is not only my friend, but she runs a group called the content creators mastermind, which I've been in since the beginning. I love it's had a huge impact on my business. Look, you guys were both named Jen, and we figured it out at some point. We're born in the same year and we're both married to men named John. 

It was inevitable that we would be friends so please help me welcome Jen – I'm so happy you're here.


Thanks for inviting me. 

I'm happy to be here - I love talking with you, Jen.


I love talking with you too. 

I hope your experience is going to be so valuable to the women who are listening so if you don't mind, let's just jump right in. Are you ready?


Absolutely, yes.


Can you just tell us about your experience when you were living under the shoulds?


Well, I think I'd like to say that I don't live under the shoulds anymore, but I still do because I'm human. I'm not going to pretend like I don't should all over myself. It's something that I struggle with. I'm just highly aware of it in a way that maybe I wasn't before.

I think about how many years I woke up hating my body because I should be a size, whatever, whatever the size was that I wasn't right. Just how much energy I spent shoulding all over myself about the size that I was or the weight that I was or going into a meeting when I had a job as a teacher and feeling like I should have said this, or I shouldn't have said that. 

Then walking away from a meeting, beating myself up thinking like, oh, I sounded like such an idiot. Or I wish I had said that thing because nobody else said it. I think what we're talking about, ultimately, is this thickness of second-guessing ourselves no matter what we do. I say that forever. I mean, I always say if when people meet me, they're very surprised to hear this because I come off as very confident and I am confident and I am strident and I am direct. 

I'm not everybody's cup of tea but I definitely still have those thoughts about should I do something? Or shouldn't I do something? It still weighs on me, but it just doesn't weigh on me as much as it used to. 

I don't want to pretend like I've eradicated the shoulding – t's just not as noisy as it was.


Oh, Jen, I love that. 

You just said this – I love this so much because I do think we have this expectation like well, okay, done and done fix that I'm out of here. That's just not true but it is how it impacts you now so the idea that the thought should I or shouldn't I would never occur to you again. 

That's just genius and I love that you said you are confident but you still think about these things. It sounds like to me if I'm if I'm hearing you correctly, sure it comes up but you don't ruminate on it and you don't look at it afterwards every 10 minutes while you're trying to fall asleep about what I should have could have would have now it's just what's the decision and most probably most of the time move on from that I'm sure it's normal it's human to second guess yourself just not staying stuck in that second guessing.


The ruminating, the poor separating, the beating yourself up, the invisible whipping – that's mostly gone. It's very freeing to have it mostly begun, but I'll tell you some of the things that happen.

I was with my best friends there with another couple, and we were talking about finances. I was talking about the dreams for my business, and these are people I have known for 13 years. We were just having a really open conversation about income and I was specifically speaking about, like, my dreams, and I am really proud of what I accomplished in my business last year, and we were talking about that, and don't I come home and the shame and the shoulds start to wash over me like, you shouldn't be talking like that. 

They're gonna think you're such a jerk – they're gonna think you're so arrogant, you made it all about yourself. You're just, you know, the shoulding and the shaming. It washed over me. 

These are not strangers to me, right, so what happened? I didn't stay in that space very long because I had strategies that helped me move out of it. One of them is to remember, like, these are my best friends and we talk about this stuff all the time. They're not judging me, they're probably happy for me if anything so like, yeah, kind of putting things into perspective in reality. 

The second thing is, when I feel shitty, or shaming, I will, actually, instead of like telling myself and in a noisy story, in my head, I'm much more likely to reach out to that person and say something like, I've really been thinking about what we talked about. I'm worried that it came off like this, I just wanted to let you know that xy and z. This is what I'm thinking about so rather than having it going on in my head, I just kind of bring it back to the source and say, hey, did I perceive this wrong so I will be much more likely.


Alright, please, when we were emphasizing that point? You were going back to that person I know we are live recording?


How many times do we have this story that we tell about something like some interaction, or we never clarify so I'm much more likely to go clarify it. I think doing those two things, like reminding myself that, you know, what I'm talking to myself about is ridiculous. 

Then if it really can't stop it, then I circle back around to the source and sometimes I do need to do a third thing, which is talk about it with somebody else who can kind of mirror for me and give me a different perspective of like, you know, is that really true is that and if it is true, so what I have a very good friend who she and I do this for each other. The tool is called and then what you know, and then she'll say so you know, you've had this conversation about money and the money that you made last year, what you want to make in the next year, and they judge you for it.

Then what happened, right, and so then it helps me just unpack it so when the shoulds. When the shoulds start to open up on me, which they do, I just tend to use one of those tools.


This is so interesting, because it just occurred to me, I love your tools. 

By the way, I don't want to gloss over that but what you just said that money piece is just another should. There's all this shame in our society, oh, you shouldn't talk about money, you just shouldn't. Yet you're working your tail off to grow this business that you love that you're proud of that is making a difference right here. 

It's making a difference for women who want to make a difference in their lives. It's this domino effect of goodness out in the world. Yet there is this idea in our society, you don't talk about it so when you're honestly celebrating what's good in your life with really trusted friends, it can still come up. 

I think it's great that you're sharing it because other people just might feel like, well, I just suck –  that's why it comes up to me. I can see how people would do that – it's just crazy, but I love how you work through this and these tools you're talking about. 

I'm curious, Jen, how many times have you gone back to the person to clarify, and they've said, oh, yeah, you sucked. That was awful for me like maybe there was but I'm guessing actually, I won't say my guess I'll let you tell me. How often do they really think what you were thinking now?


I really can't even think of an example where the person was like, yeah, you really were a jerk. You know, I really can't think of a time when that person did that and there are definitely times where I haven't been a jerk. 

It's never that's never been the thing for me – it's always like, you miss read that or you're being too hard on yourself or you're you're just like, what you hear what I hear a lot from people is oh, I never even gave it a second thought.


That's exactly what I was thinking. 

How many times does somebody say I don't even know what you're talking about?


It's because we think about ourselves so much more than anybody thinks about us. 

It's very humbling, not thinking about us and the other better. The other thing I have found is, and this is kind of, I had to figure this out for myself. I used to be an incredibly judgy person. Judging people always was a first start with judging themselves. 

If you're a judgy person, first of all, it's a hard sucky thing to admit. If you're a judgy person, you're always looking at people and judging them and thinking about them. You're the very first thing you think is that other people must be doing it about you and they're mostly not like, they're really not thinking about you that much.


Because we're so busy thinking about ourselves – what other people think of us and the other side of that coin is I love to say, you know, you might as well just do what you want to do, because people are going to judge you. 

We're human, we judge everything that's happening every single day so do you want to hide and be small and worry about what people are going to judge you for. Or just do it and let them judge you anyway?

Jen, what would you say helped you get to this place where you were able to bring in these three tools before that? I imagine things were very different for you – what has to get here?


A couple of things. 

One is, I happen to be surrounded by people who should all over themselves who are more extreme than I than I did. I think like, I have some people in my life who have definitely gotten lost in really caring what other people think like, it's, it's, it's been so heavy for them. It's weighted them down, I guess. Yeah. And so a very important piece for me was looking at them and saying, I don't want that. I don't want that for myself. So I suppose seeing it and other people and saying and saying I don't want to choose that. So what do I have to do differently? Nice, was one thing. But that doesn't mean it's easy. Sure. Um, in fact, my best friend and I have very, very open conversations about this. She's a person who will admit and she and I have done interviews about it, she is more of a people pleaser than I am. So I'm one of a silent people pleaser. She's more of an overt people pleaser.


Oh, interesting. I never thought about the difference between those two.



When, you know, when she's in her pleasing mode, she says yes to everybody and everything. I'm much more likely, in a reaction to being the opposite of that. I'm much more likely to say no, so I really have much stronger boundaries.


Now I want to back up a little bit so and obviously, you don't have to say who these influences were. Are we talking that from a fairly young age, you weren't able to see what you didn't want? You've never been sort of an overt people pleaser – this has sort of been the route that you took your whole life.


My people pleasing shows it is my people pleasing shows up much more in the I have to be perfect being rather than letting let me do for you and do for you and do for you.

Like it shows more like I have to strive to be perfect for myself and then it really is less about meeting other people's expectations, and much more about meeting my insane expectations of myself.


For you, it's this inner striving, so that I'm thinking about the days when you were a teacher, you probably never let a parent down, you probably went out of your way to make sure the principals and the higher ups in the district were always stellar.

It was striving for them but that was solely internally driven and so you were making these, whereas your best friend or I'm an overt people to actually I'm both but you know that overt in case somebody doesn't know what we're talking about, is that like, I will say yes to everything, whatever you need me to do, because I really want you to like me and see me as perfect and valuable. Those are the two ways and then you saw what you didn't want and you're, I think it sounds simple, what you're saying, but if you've been sort of planted in this for a long time, then deciding to go a different route. 

I wonder if you tried a few routes that didn't work out so well.


Notably, I, one of the biggest things I remember is years after this, you know, being in a partnership business partnership with that best friend and she's the external people pleaser and I'm the internal people pleaser. 

We're both on both sides, and we're both beating the hell on ourselves. I would have such strong boundaries in a reaction to not being an external people pleaser. I would often be the one who said no, or like put up a boundary or some sort later on many years later, we were talking about it. 

She said, I always thought, how could you be so selfish? I can understand from her perspective that that's what it looked like and from, from my perspective, it was like, literally, self preservation.


That is such an interesting insight into how each person operates. 

That piece of it, yeah, if you're saying no, you're being selfish, your internal people pleaser must have driven her overt people pleaser, courageous leaders, because she probably wanted to do everything extra to make everybody happy and here you're like, nope, doesn't work.


Then vice versa, right? 

Like, her external people pleaser drove me crazy, because I'm like, if you would just make different decisions, you're like, wouldn't be so hard.


I wouldn't walk all over you, I can totally hear the conversations in both of your minds. 

What a gift that you have such a good friendship that she could say that to you that you guys don't have that sort of hidden in the background of your friendship?


No, that's one of the benefits of having somebody who, you know, you can say anything to. And it goes both ways.



I'm curious, Jen, knowing that I was instantly attracted to your work. I mean, when we met, I liked you, I liked your work. I would imagine you have other clients who are extreme people pleaser living under the shoulds. 

I'm curious how you moving past the shoulds has influenced who you work with and how you work?


People who are drawn to work with me are usually highly creative. 

They kind of live in the ethers, it's a lot of ideas that drive them. They're very passionate, but they have a really hard time having the rubber meets the road, because it's very scary.

When the rubber meets the road, you have to say no to certain things and for those people, it's really hard to put boundaries in place. In my work, I would say probably at the beginning of my business, I was much more I won't say rigid, but I was probably much more like, you need boundaries, you need boundaries, you need boundaries. 

Now, I'm probably more gentle in how I help them understand that it's not easy for my people to do what I do. Often they'll find like, if they ask something of me, and I'll say yes, they'll say really? Are you sure? Are you sure? I think I have to model for them. If I didn't want to say yes, I wouldn't say yes, and they learned that I have strong boundaries.


You are good at that, you are really good at modeling that for your people. I have seen it in action, I have appreciated it and what Jen describes is exactly who I am. 

We have a good connection, we're good yin and yang, the way you and your friend are right. Presumably, we don't just have entrepreneurial women watching this right now so do you have a piece of advice for someone who is struggling with this right now you gave your three strategies, which is great. 

It could be you know, just use those but anything else you might want to throw out there for women who really struggle with. Actually let me be clear about what it is they struggle with – it's not doing what they think they should be doing but really thinking about what they want, or what they need and considering themselves instead of just responding to what's expected.


I think that's the hardest question because sometimes when I'm working with a new client, I'll say, you know, well, what do you want? They often have no idea because they just haven't factored themselves into the equation here. The first thing I would say is, if you, if this is all resonating with you, and you feel depleted all the time, and if somebody asks you like, what do you want for dinner?

You can't even ever come up with an answer, or the answer is always I don't care. What do you want then the very first thing is to please be gentle with yourself. Just like that awareness piece, I always say awareness is the first piece because you can't make any changes until you see all the ways in which you give yourself over so easily, which you've bending over backwards to maybe where the point you're like breaking right.

That would be the very first thing is to be gentle with yourself during the awareness process and the awareness process can take a really long time. Then once you become aware, somehow we have this expectation like, oh, now I know what this is about. Now I'm never going to do it again but that's just not the way it works. 

You're gonna fall in to the trap over and over and over again so if you can kind of lovingly say, isn't that interesting there –  I am doing that again. Those are the two things that require a gentleness that we often can't do for ourselves.


I would totally agree.

I find myself saying this pretty much anytime I teach or work with a client, but like, what we're working on. That awareness piece, that's not fodder for you to beat yourself up because there's just no point in becoming aware of how you operate. 

If you're, if what you're going to do with that is then turn it around and beat yourself up with it. You might as well just live with it in the background, you know, because you're gonna beat yourself up but yeah, that gentleness. I like how you phrase that expression of oh, how fascinating my look at this. I love encouraging women to look with curiosity, and that's exactly what you're talking about. 

Let's see what's going on because what's going on right now isn't working. Why not approach this with curiosity and find out what's happening? I love that – thank you, Jen.

Is there anything else that I forgot to ask or that you'd like to share before we wrap up?


I mean, it's not pretty, the journey is not pretty or easy and you know, when you have your best friend tell you, I thought you were selfish. Those things are hard to hear or even when you see it yourself. 

You're like, whoa, gross – I hate this part of myself. It requires strength but I know that every single woman has that strength because you are already doing hard, crappy, difficult, challenging things every day. If you're already doing hard things, you might as well do something hard that actually moves you toward what you want.


You're already doing hard, crappy things. Why not do the hard crappy thing that's gonna get you towards what you want and it's not crappy the whole time. I love that and you're saying this, like, it's not roses, you're not going to work on yourself because it's going to be you know, skipping along. 

It takes effort and it takes awareness but why not do the hard lifting the hard work to get you where you want to go? Thank you so much, this has just been fascinating and you're giving me different ways of thinking about this too, which is what I love about doing these interviews, so I appreciate it.

Alright, gang - until next time, thanks for joining us.

3 simple steps laid out in 3 bite-sized videos to go from overwhelm to ease (even if you think it's not possible!)



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