Navigating Guilt & The Self-Sacrificing Narrative That Holds Us Back in Business : What Would a Middle-Aged White Man Running a Business Do???

In today's episode, host Regan Figg discusses overcoming societal conditioning and cultural beliefs that often make women, particularly mothers, feel guilty about prioritising themselves and their businesses. 

Regan explores the difference between genuine guilt and discomfort, explains how the strategy of thinking like a middle-aged white man can help break free from limiting beliefs, and emphasises the importance of aligning business growth with personal pleasure. 

She also invites listeners to join her in-person immersion event, 'Make it a Masterpiece,' designed to reset energy, reconnect with true desires, and step into a higher level of business and personal fulfilment.

(00:00) Welcome to the Show
(00:49) Overcoming Resistance to Investing in Yourself
(02:18) The Middle-Aged White Man Strategy
(05:10) Societal Beliefs and Conditioning
(12:39) Differentiating Guilt from Discomfort
(19:22) The Importance of Prioritising Yourself
(22:52) Join the In-Person Immersion

Resources / Links Mentioned:

• Make It a Masterpiece – In-Person Immersion Join me for a 1- or 2-day in-person experience (Sept 5–6, South Coast NSW) to reset your energy, reconnect to your vision, and reignite your creative fire. Reserve your seat here.

Subscribe & Review: Enjoyed today’s episode? Make sure to follow, subscribe, and leave a review! It helps more Pleasurepreneurs find their way here.

Transcript

[00:00:00] Hello and welcome to the Pleasurepreneur podcast. This podcast will help you create what you desire in your business with pleasure. Whether that be calling in your ideal clients, making more money, or creating a balanced business life blend, I'm your host. Regan Fig pleasure and business coach, published author of a Mother's Pleasure wife and mama to three little Wildlings.

However, you're choosing to listen to this podcast. Ask yourself, how can I make this more pleasurable and do just that? I acknowledge the custodians of the land on which this podcast is recorded and produced, the Wadi Wadi people of Doland. Now let's proceed with pleasure.

Speaker: Hello, hello and welcome back to the podcast. I don't know why I decided to give you a sing song, but I, I hope you enjoyed it. I have been speaking with some incredible [00:01:00] women who have. Considered or who have already signed up for make it a masterpiece. The in-person immersion happening very soon on September the fifth and sixth.

For those who are VIPs and these, there has been a common theme with the resistance around joining. And it's not about like, oh, I don't think I'm gonna get my money's worth 'cause it's super valuable. Or, oh, I don't think I'll learn anything. Or like, oh, actually I'm feeling really inspired and excited by my business.

I don't need any more clarity or inspiration, et cetera. It is more around the idea of like, oh, am I allowed to have this? And I just, I don't feel like I've earned this yet, or I don't feel worthy enough of this yet, or, oh my gosh, that means I have to hand over some of my responsibilities to somebody else.

You know, it means I am going to have to have time. I am not putting everyone else before myself, and chances are it might be the same for you too. Maybe that is [00:02:00] something that you have not done in a long time. You know, prioritizing yourself and having your, your pleasure be centered in you and really prioritizing and investing in yourself and your business.

So I wanted to speak to this. In this episode, I feel so strongly about this, and I wanna share with you a really cheeky kind of strategy that helps me when I am in this kind of an experience, when I am feeling like, oh, have I earned it yet? Am I allowed? Like, oh, but like I'm meant to carry everything for everyone all the time.

You know, it, it feels like almost like a cheat. It's super simple. And if you could read the title of this podcast, you already know. The strategy is simply looking at it from a different perspective, in particular from the perspective of a middle-aged white man running a business. I ask myself the question, Hmm, what would a middle-aged white man running a business do [00:03:00] in this scenario when I have those feelings right?

Now I don't ask this question because I want to be a white, a middle-aged white man running a business. Or because I think that should be celebrated the way that they typically run their business. In fact, I know that women need a completely different approach because they don't have that infinite masculine energy that go, go, go energy that men typically have, right?

So this isn't to say like, you need to start like shaping your whole business around what a stereotypical male would and you, which is like, I mean, the typical business model anyway, right? No, this is the pleasure preneur approach, which is more focused around feminine energy and operating your business in a way that is not just profitable and enjoyable, but also sustainable.

So you'll come to learn actually how when we do these things for our business that perhaps feel [00:04:00] frivolous or we haven't earned them yet, or we maybe feel unworthy of things like pleasure and rest and time to daydream and ins. Feel inspired and be creative, you'll start to see that that is not, as I said, frivolous.

It's actually really sensible, really responsible, and a really great strategy for your business. So I'm not saying that the question itself is an entire strategy, but the reframe that it creates is really powerful, you know, I suppose because strategy at its core is simply how you make decisions, right? And this little question snaps me, and hopefully now you out of guilt and doubt and self-sacrifice and into a place where I can back myself, where I make the moves, where I take the step.

So today we're gonna unpack the patterns that stop women in business from saying yes to investing in themselves and their businesses. And why [00:05:00] prioritizing you and your business, especially in a very feminine way. Isn't indulgent, but the smartest business strategy you've got. So let's be honest. I mean, women in business, especially US mothers in business, we have been trained to put ourselves last, to keep everyone happy, to not rock the boat, to not be selfish.

So when it comes to investing in what we see as ourselves with time, with money, with support, we overthink the heck out of it, right? Would a middle-aged white man running a business pause to feel guilty about missing one school pickup? No. He would just like reorganize that shit. And obviously I'm talking about like a stereotypical middle-aged white man, right?

Would he tell himself he hadn't earned it yet because his business wasn't at six figures? No. Would he wait until like every duck was perfectly in a row before saying yes? Absolutely not. Yeah. Like these are the exact kind of traps that so many are, but [00:06:00] of us keep tripping over. I remember I, for the International Women's Day event where I was a guest speaker we were talking about like women and business and women and money, and I thought, Hmm, I'm curious.

I might look up what does chat GBT have to say about like the top societal beliefs around. Women and business and women and money. Now, I can't remember if I have actually shared this on the pod before, so I'm just gonna share with you like what I got when I punched into chat gbt. And you can take a look at this too, like what are the top societal beliefs around women in business and money?

Let's go. Just a little warning. These are not my beliefs. This is what, this is kind of like the societal soup that we're in, that we've been exposed to and what we have been conditioned to believe as truth, and part of the reason why we have these feelings when it comes to investing in ourselves and our businesses in order to help our businesses grow.

Right? All right. Let's go top 10. [00:07:00] I'm just gonna say the first line, women should put others first. Success has to be earned through struggle. It's selfish to invest in yourself. Good mothers slash wives don't prioritize. Business. Money is a man's domain. We're halfway there. Don't be too ambitious. Your worth is tied to how much you do for others.

You have to prove yourself before you deserve support. Nice girls don't talk about money. And lastly, there's a right way to do business and it's the masculine way, like does anyone else feel a bit sick listening to that? Again, like I said, these are not my beliefs. This is what, you know, chat GPT has shared with us reflecting back to us that societal soup that I talked about.

So it's no wonder then when you have the opportunity to go for a one or two day in-person immersion or something of a similar kind of flavor for you. That you really wanna go. You see the value, you know how it's gonna improve your business and yourself, and how it's gonna help you be so much more ex inspired, excited, and like [00:08:00] sustainable within your business.

And yet there is this kind of like weight on you to not make that move, to hesitate to question yourself, to talk yourself out of it.

 It's not like women in business secretly don't want to succeed. You know, you are not lazy, you are not uncommitted. You are carrying around generations of conditioning. We have been taught since we were little girls that our value lies in taking care of everyone else first. Be helpful, be accommodating.

Don't be too much. And when we finally do something for ourselves, like cue the guilt, right? And that is also an extension of when we do something for our business, when we're looking after ourself, we're looking after our business. I take a week off of business every quarter. So every 12 weeks I take a week off like it's written in my client agreements.

I make sure everybody is aware of it because I'm looking after myself. And in turn, that means I am the best. I can be for [00:09:00] my clients for the rest of the year when I'm working with them. You know, me valuing and prioritizing myself enhances my business. It enhances my service, it enhances my care. So will tend to feel that sense of guilt and then layer on like cultural beliefs around work and worth the whole, like, work hard first, then maybe, maybe you'll earn your reward thing, right? Like the reward comes after you've earned it. Women absorb that message double time. Which means taking a day for yourself or putting money into your business, it feels really indulgent instead of strategic.

Meanwhile, men are taught to assume backing themselves is a given. I cannot imagine, like, let's just go back to the original question. I cannot imagine a middle-aged white man running a business, ever turn down a game of golf with a potential client. Or with another man, or perhaps woman [00:10:00] who they could potentially collaborate with, for example.

Right. And for the moms listening, I hate, like that's me too. The pressure, as I said, it goes up like 10 notches for us. Mothers like motherhood comes with this unspoken rule, which is to be endlessly available to be there for our kids 24 7. And how many of us are like the first person that the school calls or the preschool calls when our kids are sick?

Right. It is why so many women talk themselves out of opportunities with like, what if the kids need me? What if my partner needs me? What if someone else needs me? You know, if I'm not there for them 24 7 and I'm doing something for myself and my business, doesn't that make me selfish? But here's the kicker.

You are nervous system buys into all of this when you are living in that. Low grade stress response where you are doing all the things and you are trying to literally like fit in business tasks [00:11:00] around everybody else. I'm now like thinking about myself in school holidays, like I am the default parent in school holidays because my work is flexible.

And so that's great. Like that's what I started my business for, but also it means I have to really kind of find these little windows here and there and I'm like, I then have to be really flexible, you know? And it's like. I wonder if it's the same for you. So when we are in that sort of low grade stress response, living life, doing everything for everyone, squeezing business in with everything else that we're doing and managing and prioritizing self sacrifice actually fills safer.

This is why saying yes to yourself feels risky. Even if it is the very thing that you know is gonna grow your business or the very thing that you know you need. So yeah, it's not your fault. It is societal conditioning. It is cultural beliefs. It is like caregiver identity, fear of judgment, nervous system wiring, like all kind of working together.

Once you [00:12:00] see that, like you can choose differently, you can actually interrupt that pattern. And this little question of like, what would a middle-aged white man running a business do? It is a shortcut out of that conditioning and into decisions that actually serve you and your growth. Okay, so we can be aware that we can often self-sacrifice.

We can often feel really guilty. We can often feel really uncomfortable about prioritizing ourselves and our business and investing in ourselves and our business. Over other things in our life. I've, we've started to like explore why that is and a lot of that has to do with societal beliefs and cultural conditioning.

But what I really wanna speak to in this episode that's gonna help you so much is actually differentiating between what is actually truthfully guilt. And what is just simply the discomfort that we feel when we go against the grain of patriarchal culture and we go against societal beliefs and cultural [00:13:00] conditioning, and we prioritize ourselves and our business.

First of all, let's be really clear about guilt. To me, the way I define guilt is when we do things that goes against our top values or we prioritize things that are. Not in alignment with what we value most. For example, if I had a dinner date with some girlfriends or a business like coaching experience to go to out of the house and I've got my little baby at home.

I don't have a little baby anymore, but I'm thinking back to when I did and they have gotten sick and they've got a fever and they really just want me and boob. If I went, no stuff it, I am prioritizing me and I'm doing this thing, I'm gonna feel so much guilt simply because it's keeping me in check with what I actually really value.

So guilt is there for a reason, just like the [00:14:00] feeling of being an imposter is there for a reason. It And if you haven't listened to the imposter syndrome episode, I highly recommend it. I've gotten so much feedback that a lot of you loved it, so if you haven't listened to it already, jump back in.

I talked in that episode about how there is value to that sense of like imposter syndrome. It has us check in with our integrity, just like there is value with this experience or this dis discomfort of guilt. It has us check, am I in alignment with my top values? Yeah. But I want you to ensure that you can actually differentiate between genuine guilt versus the discomfort.

Of going against the grain of patriarchal culture and our societal conditionings and cultural beliefs around who we are supposed to be and what we're supposed to prioritize as women in business, as women in the world, as mothers, et cetera. This can get really murky. I've had many clients, both when I worked with mothers who wanted to experience more pleasure and now women who wanna experience more pleasure in their [00:15:00] business.

This can get really murky territory where it's like, oh, I feel so guilty investing this money in my business. I feel so guilty having some time to prioritize my work, et cetera, et cetera. Oftentimes it isn't actually guilt. It's not actually guilt, it is simply just the discomfort. Of going against what we've been conditioned to believe.

So let's dive into how you can actually tell the difference between guilt and discomfort. Remember, guilt, like the real kind comes when you have genuinely gone against your values. Like my example of, you know, if my baby was home sick and I ditched them to go do something that didn't even matter to me.

Of course I would feel guilty about that because that's my body saying like, this isn't aligned for you and no judgment if that's something that you would do, but that's my personal values and you're gonna have your own too, versus simple discomfort, which is the conditioning kind, which you know, shows up [00:16:00] when you are in integrity.

You are doing something that perhaps is new that your old programming says is selfish or wrong. For example, leaving the kids with your partner so you can attend an immersion. You know, it's not betrayal to your top values. That is, you know, you stretching past the limit society has set for you. So here's the difference.

Guilt feels heavy. It feels sticky, it feels regretful. It's like you have broken trust with yourself. Discomfort feels like edgy. I think in a past episode I've talked about like getting bum sweat, bum crack sweat or getting sweaty palms, right? Discomfort feels edgy. It feels kind of like tingly, you know, like the difference between like nervous and excited maybe even like butterflies.

It's uncomfortable, but also expansive because deep down, you know that you're actually choosing growth. But yes, it can feel uncomfortable. Like, oh, you might have thoughts of, [00:17:00] oh, am I allowed to do this? Or, I shouldn't be doing that, or I need to be with my kids 24 7. Or, I, you know, I'm, I've done enough for myself already this month, or I've invested enough in my business this year, et cetera.

When we really dial in. Discomfort can feel like awkward. It can feel like judgment. It can feel like resistance, but ultimately there is a part of us that's like, oh, I have that want, and that want is like a desire, it's like a little spark. That's where like the edginess comes from. That's where like the tingly kind of, butterflies in your tummy can feel from.

So when that sense of. Let's just call it discomfort, whether it is guilt or discomfort. When that shows up, perhaps check in where it is in your, in your body, it's probably in your stomach. I want you to ask yourself, if no body was judging me, what would I choose right now? The next question that can be helpful, does this honor me as well as my top values?

And the last one, am I out of integrity here or am I just [00:18:00] stretching into. Something that could be new or could be going against my conditioning or society's beliefs. And the reason why, the question, what would a middle-aged white man running a business do is so effective is because the typical middle-aged white man running a business doesn't, they're not soaking in that societal soup.

Well, actually they are, but they don't have that conditioning. They don't have those societal beliefs and cultural conditioning, that they must be prioritizing their family first. That they must be givers, that they must, be carers and not be paid for what they do et cetera. Like they're expected to prioritize themselves and invest in their businesses.

That would be smart, right? But we have a whole different playbook as women. So when you are feeling the funk of like wanting to invest in yourself and your business. And number one, I would invite you to consider, well, is it guilt or is it discomfort? And number two, kind of like [00:19:00] test that out. And when you ask yourself like, what would a middle-aged white man running a business do if it's like, oh, he would totally do that.

It kind of like the reason why that answer can come so simply is because there's not those layers of conditioning and beliefs. There is not those reasons ingrained in them to feel guilty or discomfort for making those choices. now middle aged white men aside here is why prioritizing yourself and investing in yourself and your business is strategy.

Great strategy, great feminine strategy, right? Here is the reframe. Taking one or two days to reset, to refocus and reenergize yourself, it's not indulgent. It is literally how you make better business decisions. Your creativity doesn't flow when you are fried, right? Your nervous system is not going to feel safe enough for you to be creative and inspired when it thinks that you are being chased by a [00:20:00] saber tooth tiger.

Your clarity. It doesn't land when you are exhausted running on fumes. You know, just going through the day to day and feeling like you're on autopilot and your momentum, I wanna say it dies. This is very dramatic, but I wanna say like it dies a slow, painful death when you are stuck in guilt and martyrdom.

Yeah. Like when you give yourself permission to step away, to be inspired, to feel alive again, that is when the big ideas land. You know, that's when the left of field opportunities arrived. That's when you see the the next moves to make. That's when business feels like a masterpiece instead of some kind of grind or instead of some kind of like puzzle that you need to like find the missing puzzle pieces for.

Right. So back to the original question, what would a middle aged white man running a business do? He'd say Yes, without the drama, without the guilt, without the 10 [00:21:00] layers of justification and the second guessing, the backwards and forwards.

Right? So honestly, it's time. You did too. Your business. It doesn't grow when you keep putting yourself last. It doesn't grow when you treat everybody else's needs as more important than your own vision. It doesn't grow when every time you feel discomfort, you call it guilt and like back away, and it certainly doesn't grow when you assume that prioritizing yourself or your business is selfish, so that you sacrifice your energy, your ideas, your desires, It does grow when you choose yourself without apology. You know like when you actually honor what your true desires are and you take the steps towards them without needing to apologize. It grows when you prioritize your desires alongside your top values.

It grows when you know the difference between true guilt and discomfort of growth. And you move through the discomfort and like strengthen that [00:22:00] muscle. It grows when you see investing in yourself and your business, not as selfish, but as strategy, and it grows when you stop self-sacrificing and you start leading from a place of pleasure, from alignment, from your next level self.

If you've been listening to this thinking like, oh shit, this is exactly what I have been doing, self-sacrificing, putting myself in my business, desires last, pulling away from everything that feels uncomfortable or like guilt. If you've been listening to this thinking, I so need this right now to invest in and honor myself and my business to collect the evidence that when I do invest in myself and my business, when I do let myself say yes, just like a middle-aged white man running a business, would it actually enhances and improves my performance and the performance of my business.

If you are listening to this and thinking, yes, I need all of this, then I invite you to start with my in-person immersion happening this [00:23:00] week. Day one is Friday, VIP upgrade is Friday and Saturday. It is not too late to buy your ticket. It is never too late to start learning to prioritize yourself and your business and seeing that on the other side of that the world hasn't ended, and actually seeing such benefits come from it.

Yeah. So the in-person immersion, make it a masterpiece. It is one or two days if you're there for the VIP option. It is designed to reset your energy, reconnect you with your desires, your true desires, and help you step into the identity of the woman who actually create them. You are going to walk in perhaps questioning yourself, perhaps feeling a little flat, perhaps feeling a little, um.

you're on a hamster wheel and you kind of wanna get off it and you're gonna walk out feeling clear and confident, and I wanna say like relaxed and cup filled from the spa, the sauna, the long lunch with a bunch of incredible women. And you are going to be so much more embodied in your next level [00:24:00] self.

This is not a luxury, I mean, but it'll feel like it's, it is strategy, it is, as I said earlier, feminine business strategy is the pleasure preneur. Business strategy. So click the link in the show notes. Day one is just under 200 bucks. The VIP two day ticket is just over a thousand. Your return on investment is going to be 10 times what you invest.

Grab your spot and come and join me. And a whole long lunch table full of incredible, full of incredible women just like you who are gonna be on there on the day. I can't wait to host you. I love you so much. [00:25:00]