Episode 77: How to Feel Into More Money with Guest Jaime O'Connor

Emily coaches an entrepreneur, Jamie OConnor, to step into higher revenue months more effortlessly and with less friction.

Jaime OConnor is a leadership & purpose alchemist. She helps driven, successful and high-performing female entrepreneurs connect deeper to their true purpose and find alignment in their business and their life.

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Jamie: I know there's so much more for me and I find myself in this place of, it's not a do like hours for dollars piece but there's definitely a connection to more work.

Emily: Yeah.

Jamie: For more money. Like there's definitely a through line that is keeping me from making some moves that would increase my revenue and all honestly, using the excuse of, well, the baby is coming. I don't have to deal with having to figure that out and I wanna give myself all the time and there's the stories come up that are the layer above.

Emily: Got it. Okay.

Jamie: I don't know if that was really a question, but I think the context gives you the direction.

Emily: Yeah. And I think essentially the question, the way that you had sort of framed it the first time, I really wanna step into higher revenue months and I'm sort of feeling some crunchiness around having to work harder in order to do that, it's gonna have to be more clients and more work for more money. 

Hi, welcome to the show and thank you so much for being here. I wanted to share an incredible free resource with you. That's been a money game changer for more than a thousand. And a few men too. My money wounds quiz will quickly diagnose your top money wounds, and then you'll get access to a free masterclass on how to heal them.

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Hello and welcome back to the show. I'm feeling so fired up with just how cool my life is. I feel so grateful. And also this is gonna sound braggy and I guess it is, but like I just feel like such a badass and I love what I'm doing.

I love the ways that I'm able to help and. I love the ways that I'm making money, and I love that I get to share that, especially with my inner circle of clients. So one of the things that is happening in November is I'm running a live program called Legacy, and it's really about building wealth that outlives us.

And the cool thing that I'm doing that I do not see happening very often in the coaching. Is I'm actually bringing in my own wealth strategist to teach one of the days, and we're gonna share exactly the ways that Jeff and I invest our money and not so that you have to do exactly what I do. But I just find that so many other coaches, like either they don't talk about that piece or they talk about it in passing, like, Oh, I own some land and some this, and some that.

And it's like, Okay, but who are you working with? How do you do it? How is the deal structured? Is it something that I can get in? I know that I personally love having the details so that it feels like I can research it and I can find out if it's for me. And so that's something that I'm offering inside of my program called Legacy.

So if that lights you up, If you want to know all the behind-the-scenes on how Jeff and I are building legacy wealth, that will is guaranteed to outlive us. You can come join that and we'll make sure that the link is in the show notes at the time of this recording. It's on presale for 5 55, but the program ultimately will be 1,555 and there will be some payment plans available, but if I could have paid 1500.

To have known this stuff decades earlier, it would've been the best investment in my life. There are just incredible legal ways to multiply your dollars, and you can start sooner than you think. I think a lot of us feel like, Oh, but I don't have any disposable income. Oh, I'm just living paycheck to paycheck.

I can't do that. I have to have more money first. And I will tell you that you really do not. You really don't. There are ways to start right now and it does not require a bunch of penny-pinching or belt tightening in order to do it. So if that's something that peaks your interest, please join us inside of Legacy.

Now, the episode that I have today is so great. It's continuing on in some of these series of watching me in action and getting to hear me coach other incredible women, and I just feel so honored that this is what I get to. And that a lot of the women that I coach get to be in my inner circle and get to hear all the behind-the-scenes on what's happening in my world.

And I get to be behind the scenes on what's happening in their world. So if you're thinking about one-on-one mentorship or joining a mastermind, Either right now or just setting yourself up for 2023. You know my vibe. If you listen to this show and if you feel like I might be the person for you, I just invite you to slide into my DM so that we can explore that together.

It's one of the most special types of relationships, and I will say like I talk to my clients more than I talk to anyone else, more than I talk to my family, more than I talk to my mom, and it just is such a special relationship because I get to be in the front row, helping along the way and just cheerleading you, and you get to have a front row in my life too, and you get to ask me any questions and there's nothing that's off limits.

We talk about motherhood, we talk about money, we talk about sex, we talk about marriage, we talk about hobbies, like we talk about the moon, everything. It's energetics, it's strategy, and there aren't that many spaces like that. I will talk to you deeply about like breaking energetic, breaking generational chains and what's happening energetically and how to get align energy behind your goal, and I will also talk to you about, okay, what numbers are you projecting and what is your payroll and how do we break that down and what should your profit margins be in your business? I do like to roll up my sleeves and get tactical as well, and I just. I don't think there are that many mentors that really do both, and not everybody wants both.

But for those that do, I'm your person and I would love to explore with you if it feels right. So my guest today is the incredible Jamie O'Connor. And Jamie is a leadership alchemist. She helps driven, successful and high performing female entrepreneurs connect deeper to their true purpose and find alignment in their business and their life.

And as she and I talk today, you'll see how she's done that in her own life as well. She's built four successful businesses. She's navigated millions in revenue. She's done it from the hustle and grind before finding real flow. I can absolutely relate to that. But everything changed for her when she became a mom at age 35, and she just totally reevaluated what success looked like.

And her self-discovery took her on a journey that really unlocked a lot of deep intuitive gifts for her. And now she's using those experiences to help other women to really step into what their greatest power and their greatest definition of success looks like. I know that you're gonna love this episode, Jamie.

She's just has infectious energy. You can tell that she's so lit up about her life, and as I've always said on these, it's incredibly vulnerable to be willing to be coached knowing that the coaching session's gonna go on a podcast, and I just. Honor the hell out of Jamie, and I hope that you guys connect with her as well.

So without further ado, let's jump into the show welcome to the show.

I am here with Jamie O'Connor. Jamie, thank you so much for joining.

Jamie: I am so excited to be here. I love your work and I feel honored to get a chance to experience it.

Emily: I, No, I'm so happy because we had a little online connection. I don't know, has it? We were just thinking maybe it's been a year. Although time is such a wild and

Jamie: yeah, what was, it was definitely Melanie's November course. November class. I hadn't signed up for afe and you had said something about your experience, your journey of agency owning, and I was like, Oh my God, that's my story. But I'm like a year behind.

Emily: Yeah. So we connected and hopped on a Zoom and then since then you joined Melanie's Alpha Fem experience. You've run a retreat and I just saw you announce that you are officially gonna be winding down your agency. So like, tell me all the things.

Jamie: It's pretty amazing, honestly. I'm like such a good place in so many ways. And your post was also like, definitely like pinged I need to work on. So I'm excited for what we're gonna work on today. When I talked to you, I hadn't, I didn't even have a first client yet in the coaching space. My agency was thriving and doing really, really well, and I was like, What do I know?

I'm being called to do this other work and I really don't know how or what to do. I had just hired a mentor and I was considering signing up for and definitely was experiencing some imposter syndrome. Didn't wanna burn down my entire agency, even though I was like really wanting to do something else.

So I admired that, like your post and the fact that your agency was doing so well and that you had been building this coaching business. So I think in a month of that, I actually got coaching client which amazing. And then I got another one. And so I had two that I was way undercharging for.

It's all good. It was good though because it really got me into the groove. And so that was about a year ago. And now I decided to launch my retreat in, I put the deposit down for that. In April, I had canceled two retreats. Prior to that, I had lost two deposits that I did not end up running. And this one, just everything aligned. The place showed up. Just everything kind of fell into play and I announced it on Instagram and I got four people to buy, and I was like, All right, well that's enough.

Emily: We're doing it. We're really doing it.

Jamie: I'm doing it. It doesn't matter. I'm actually doing this. It. I have enough people and I had gotten into the mindset of I want 10 and if to sign up, I'm doing it beause I'm just in.

Emily: Yeah.

Jamie: Like I'm done.

Emily: Yeah.

Jamie: And that was a huge energy shift that made it happen. And I ended up having seven women and a co-facilitator who also kind of participated.

Emily: Yeah.

Jamie: And. I remember waking up on the final day of the retreat and being like, My life has changed. Like I just know this is it. What was really interesting, it was three days before, so this was September the end of October now, three days before I just got this hit, like it's time to close the agency and I had said to my team, I brought them the opportunity, my two main girls that run everything, taking over 80% equity.

Emily: Mm-hmm.

Jamie: running it the. And it was the way I structured it was the opportunity. I had always wished that somebody had given to me, like I'd always desired somebody to like mentor me into business running, but I kind of like did it the cut my teeth way and for their own reasons, which I fully respect. It wasn't for them.

And I had gone into that conversation with the very grounded ability to say whatever happens. I already know I'm going this other direction. For me, it really, like I don't have a partner in the agency and I didn't have someone to take over the leader vision position.

Emily: Yeah.

Jamie: Without somebody deciding to do it. And I really came to the conclusion and I let go of all of the shame of like, I've built this, I need to hold onto it.

Emily: Right.

Jamie: I came to the place of it's okay to have been so proud of what I've done. It's okay to be so proud that this last year I was able to have the ability to pay for two of my employees to have paid maternity leave and if like, honestly, if nothing else, if I have that alone

Emily: Yeah.

Jamie: That I was able to do for people I love so much. Oh my God. It was worth it.

Emily: Yeah.

Jamie: It was worth everything I put into it, including all the businesses I helped, including all the business experience I I've grown to have, including all the strategic genius I've learned, like

Emily: Yeah,

Jamie: all of that. It was worth it. It was worth everything and I knew, I was like, it's time. And then I leave for my retreat and I was in my. Like so there, and these women connected so deeply with their truest selves. They connected with their lines of dma. They knew where they wanted to go. They were so in their power, and every one of 'em were six weeks out from it.

I've continued connecting with a lot of them. Some of them became private clients. The change stuff and that feels so good. It's like, oh my God, I'm doing what I'm supposed to do. I'm doing what was like the wisdom that was put into my soul before I arrived on this earth. And that's amazing. So,

Emily: well, congrats. This is all incredible. And I think before we move fully into the questions around money and the coaching business and everything, how much was your agency bringing in on an annual basis?

Jamie: So we were at about a half million.

Emily: Okay.

Jamie: Consistently for three years. Yeah. I plateaued there. That was like where I was.

Emily: Which is so amazing. Like so many people would, if we're built a business that does a half a million dollars a year, it would be incredible.

Jamie: Yeah.

Emily: And we're shutting down a business this year also that has generated more than 3 million in lifetime and what have you. But like here's the reframe. Which is like, that's like the price that you put on your freedom and that's the price that you put.

Jamie: Totally. I love that. I love that. And it was so interest,

Emily: but people don't it. They're like, I don't, It must have been failing, right? Cuz you don't ever shut anything down unless it's failing and it's like, no, actually this is how much I value. Stepping into my purpose. Mm-hmm. .

Jamie: Oh my God, I love that. That's so beautiful and so amazing.

And there's interesting caveat too, right, That I had put down the year prior, I was like, I wanted to do the million-dollar year thing, right? Like that's, I couldn't attach to it, right? So what I attached to, and I really put out there and I manifested, was an $80,000 month. That's the breakdown. And I had an $80,000 December in 2021 and I had an $80,000 January in 2022, and I landed like big Fortune 500 like clients, right?

And then that was like the impetus of the, this is not really what I wanna be doing. And it just started like downward spiraling from there. It was so interesting. Like it was so interesting to watch as. Put my energy into what was like lighting me up.

Emily: Yeah.

Jamie: To see like what was happening where I had built my entire agency. Now I know because of the codes I'm getting and the things I'm understanding about how I built my work before was from my energy. And from my focus and from where I was lit up. And so I never got clients from funnels. I never got clients from ads. I never got clients from any of the things that I actually did for other people.

Emily: Yeah,

Jamie: I got clients because of the energy I was putting out into the world, and they just showed up and that started disappearing. And now, I just made the announcement that I was making this transition two days ago, and I'm having people show up for the coaching. I'm having people show up and it's like,

Emily: yay.

Jamie: So interesting. But I love that reframe.

That's so beautiful.

Emily: Okay, so you had a question that you wanted to bring forward, so I'll let you share it in your own words.

Jamie: Yeah, and it probably has evolved a little bit since I even initially talked to you, so it really is a little bit of context in. I am six months pregnant right now with my second, I'm in this freaking beautiful spot where I have fully replaced the income that I had from the agency. It's good. I've never had a schedule like this before. I have one day a week that's booked and I think one hour. Otherwise, it's so beautiful and I desire more financial resources mainly. I know there's so much more for me. and I find myself in this place of. It's not a du like an hours for dollars piece, but there's definitely a connection to more work.

Emily: Yeah.

Jamie: For more money. Like there's definitely a through line that is keeping me from making some moves that would increase my  revenue and all honesty. Using the excuse of, well, the baby is coming. I don't have to deal with having to figure that out and I wanna give myself all the time and there's the stories come up that are the layer above.

Emily: Got it. Okay.

Jamie: I don't know if that was really a question, but I think the context gives you the direction.

Emily: Yeah. And I think essentially the question, the way that you had sort of framed it the first time was like, I really wanna step into higher revenue months. and I'm sort of feeling some crunchiness around having to work harder in order to do that. Like it's gonna have to be more clients and more work for more money. Right.

Jamie: Yeah.

Emily: So are all of your clients one on one right now?

Jamie: Yes. I would say yes. And cause what I did after the retreat was I created a small package that had lesser one to one.

Emily: Okay.

Jamie: A small mini mind.

Emily: Mm-hmm. ,

Jamie: and then an upgrade that would be a monthly payment plan for the next recruits. So I've stepped into a slight amount of hybrid.

Emily: Okay.

Jamie: Yeah.

Emily: Well, so I mean, based on your current offer suite, it does make sense logically that your mind is going there a little bit. . Well, it actually is more time for more money, right? Because that is one-on-one work. Now, I will say there are different ways to structure one-on-one. Like I don't know if you're doing weekly calls or if you're doing Voxer, any sort of like chat or voice support in between, but maybe you can give the context for.

Jamie: Yeah, so currently the highest package I have is weekly one-to-one and full Voxer support.

Emily: Okay.

Jamie: And then I have a couple clients that are doing two times a month, one-to-one, and Voxer support. And then all of those clients have access to the mini mine that only has boxer support Monday through Wednesday. But, so there is this mini mind.

Emily: Yeah,

Jamie: that I'll, The context that I have for it is that the idea is actually an attenuation of retreat or an upsell prior to retreat. So at the moment, that offering doesn't exist unless you also sign up for a retreat.

Emily: Got it. Okay. And so where are you at now in terms of monthly income?

Jamie: I'm gonna have to actually because I just had someone. So 7,500.

Emily: Okay. 7,500. And when you think about stepping into bigger revenue months, what number feels juicy?

Jamie: A hundred thousand.

Emily: How much friction is there for a hundred thousand? Let's forget about a hundred thousand for now.

Jamie: I know

Emily: cause there's gonna be lots of numbers on the path to a hundred thousand, but we wanna pick a number that feels abundance but has less friction associated with it.

Jamie: So 20,000.

Emily: 20,000. Okay. Cool.

Jamie: So we're talking, That would be more than I've ever made personally, ever, because of how little overhead there is in this business.

Emily: Totally. Okay. So we're talking about a $12,500 gap that gets you there.

Jamie: Mm-hmm. .

Emily: So if you sort of had a magic wand and you could either have like one private client come in at 12,500 a month or you. Maybe 12 women in a mastermind that each paying a thousand a month, or six women that are paying for the Mastermind plus the retreat. Like if you got to have it any which way, what way feels the most effortless receiving.

Jamie: I would say what probably feels most effortless is mini mine plus retreat at a payment plan of 2000 a month. And that would be six people doing, I think that feels like the least amount of work that I'm gonna have to put in.

Emily: Yeah, cause you're doing the retreat anyway. Mini mind. Anyway.

Jamie: It's, it's all like done, set going, right? Yeah.

Emily: So how often are you talking about and making that offer.

Jamie: Not. I think I've done that like twice, and I think there's resistance in it right now because it is quite a bit more than the people that are in it now have been paying. In all honesty. Now that is partly because. In all honesty, the people that are in it right now were the humans that had such full belief in me and I know are going to, They will the next round. They'll pay that they, it won't even be a problem for them. And honoring, I think, for me, in both ways of like,

Emily: yeah ,

Jamie: you jumped in with me when I was like, he's gonna have this mistake.

Emily: Yeah, totally. No, that makes sense. And we often do this, right? We often incentivize the people who are willing to say yes first, right? Yeah. There's early bird pricing, there's pre-sale pricing, which is like, it's good for both of us. Cause if you know that you wanna say yes, then it gives me faith and belief that it's gonna happen. It helps everybody.

Jamie: Yeah.

Emily: So is there resistance because there are women in the container paying or is there resistance because you don't think that six new women will pay more?

Jamie: It's definitely around. I go to like six women. The total number, like six women paying 24,000 for that. Why would they do that? Yep. Definitely where it is.

Emily: So because the next retreat is when.

Jamie: The next retreat is May, and this would be like, I guess what I would be selling, and I don't necessarily have to, I guess is like a year container that would many nine plus the retreat that happens in may.

Emily: Well, what if you just let them enroll now and they're just paying two K a month between now and the.

Jamie: Yeah.

Emily: Do those financials make sense for you?

Jamie: Yeah, totally. Yeah.

Emily: Play you around with that, but I think to me, that feels more effortless.

Jamie: Yeah.

Emily: And you can even tweak the amount. Okay. So let's say that somebody wants to come in in February, but they wanna go to the retreat in May, they might pay more than 2000 a month.

Jamie: Right? Because it's a,

Emily: Because it's a shorter runway and they're still getting a retreat. But

Jamie: yeah,

Emily: let the retreat be like the exclamation point at the end of the sentence, and then at that retreat. Make an offer.

Jamie: Yeah.

Emily: That can then you have offer either be the same kind of container or a different kinda container

Jamie: and then they'll have the option too for the next retreat is like five months later. And so if they wanna add that on and yeah, it definitely such a good point because it's all things I'm already doing. I'm already planning on selling and it really is getting around. The fact that these are so valuable, I totally undervalued the last retreat and I know that like the transformation that was experienced was so huge and I upping my ability and my commitment to pay stretch amounts that I haven't paid before, and I think that's also helping a little bit.

Emily: Definitely. If we haven't paid for a retreat or we haven't paid for a Mastermind, it's a little hard to be like, I want you to pay five grand for this, but I don't pay that. It's like, not that we have to, but it definitely helps build the belief. So I love that you're stretching there. And then yeah, just play around with like talking about it and selling it, cuz I think that might be another point that's just a little bit stretchy for you. You never had to sell in your agency and

Jamie: Yeah, and just kind of showed up,

Emily: right? Yeah. And then a lot of these humans that have already known you in your network have just shown up for this coaching work, and that's so amazing. And we want that to continue. And there's like a baby muscle that's gonna have to get flexed and get a little bit stronger, which is like,

Jamie: Yeah.

Emily: Can I figure out how to actually talk about something that's not easily quantifiable? We're talking about like an energetic transformation. And can I put words to it and can I put feeling to it? And can I vulnerably start making this offer even if it feels like there's crickets on the other end? Can I still show up for me and show up for these women and do it

Jamie: and just keep showing up? Because people will show up with the like fully self validated belief system that this is amazing and the right women just need to. I love that.

Emily: I know, right? Like now it's like, Oh, okay. Actually it's so easy to get to $20,000 a month. To me, it feels inevitable.

Jamie: Yeah, and I think that that's been the interesting thing is that for the first time in my life, it all feels inevitable. Like it all actually feels incredible and I feel less uncomfortable with the gaps than I did five years ago when I was starting my agency and the things I was going through there. I almost feel too comfortable, almost feel like I could just nestle into like, I'm gonna enjoy what I have until the baby comes. And then I'm like, No, that's not.

Emily: And if you notice that happening, like then it's just getting behind your mission again, like writing that down, like having something to remind yourself that like it's not just about the money and like me having a cozy schedule, This is about my darma.

Jamie: Yeah.

Emily: In your words. And it's like if there are six other women that wanna say yes to this that I'm supposed to be helping. Then I need to show up for them and I need to put out that energetic lighthouse, that beacon, so that they can make their way to me.

Jamie: Thank you for the reminder.

Emily: You are so welcome. I'm so excited. You're gonna have to keep me posted. Slide into my dms and let me know how all, Gosh,

Jamie: no, totally. No, I love this. It's such a good reminder and such a good experience and so beautiful.

Emily: Amazing.

Jamie: Thank you.

Emily: Well, thank you so much for coming on. This was so fun.



What did I tell you guys? Jamie is so amazing, and if you had any aha moments, if there was any light bulbs that went off for you during this show, head on Instagram, like screenshot this episode, share it in your stories. Tag Jamie. She's @Jamie O'Connor and tag me at Em Makes Money. I would love to know what your top takeaways were and I will share with you.


1. When we decide to leave a business opportunity behind, we can look at that as how much we value our freedom and our mission. Number two,

2. So much can change in a year when you follow your intuitive guidance system.

3. The coaching industry is so rad. You can often replace your full-time income with very part-time work.

4. When we're dreaming into more money, it's important that we pick a number that feels abundant, but doesn't hold a ton of resistance for us. And number five, ask yourself, what way can money come that feels like the most effortless receiving.

With that, thank you so much as always for tuning into the show. It is such a gift to be doing this work. You guys are a big part of the reason that my life feels so rad. Like I just love that I get to do this and that I get to put this podcast out for free for anyone who wants to tune in and get inspired.

So, If you've been loving the show, please leave us a review. Please share it with a friend. Please share it on social media. I will tell you those things make a world of difference and they're absolutely free, and I just thank you from the bottom of my heart and I can't wait to talk to you soon on the next episode. Bye.

Listeners like you make this show what it is. So thank you for tuning in. Please subscribe, leave a review and share this show with someone you love. I always appreciate listener feedback, so feel free to slide into my dms on Instagram at m Makes money as well. And if you wanna explore hiring me as your money healer and business mentor, head to emilywilcox.com to explore.

Until next time, I'm sending you all the magic money vibes.


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