020: Pricing Psychology with Jacquette Timmons
8 Dec 2025 · 36 min
Transcript of a Freetime Cafe podcast episode (host Jenny Blake) featuring financial behaviorist Jacquette Timmons. The conversation explores the human side of money—balancing money mindset/manifestation with financial math—plus pricing strategy for small businesses (financial, emotional, personal dimensions), product cadence (quarterly Pricing Made Human workshops), and business pivots during COVID-19. The episode includes practical exercises, pricing philosophy (rejecting “charge what you’re worth”), and audience calls-to-action.
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Hello my friends. Welcome back. I am delighted to have my good friend Jacquette Timmons here with us today. I have known Jacquette for almost a decade and we spoke at the same conference shout out to Lexi Vernon. Jacquette's energy was just this bright, beaming, powerful, explosive. Not to mention her fashion sense is out of this world. She is just a radiant person inside and out and she focuses on the human side of money. Jaquette works as a financial behaviorist and is committed to getting you to see that you don't manage money, you manage your choices around money. In addition to being the author of Financial Intimacy, Jaquette is also the creator of programs like the Comfort Circle Dinner series, her quarterly Pricing Made Human workshop, and host of the podcast More Than Money. Jaquette, welcome to the show.
Thank you so much Jenny. I'm so delighted to be here. Yay.
I am thrilled to have you. I've been binging your podcast. As I mentioned before, we hit record and one thing that stuck out was this conversation around money manifestors and money manifestation coaches. And I was really struck by your explanation that you you actually come from a background in wealth management, you got a master's in finance, you can tell me the exact degree. So you're just really someone you've been self employed in this arena for 21 years if not more by now. Oh my God, you really have run the gamut on all of this and to have a business of your own that is thriving 20 plus years in I just think is incredible. So I'd love for you to just kick us off with how do you approach money and strike that balance between the energy manifestation side and what you call the math of Money.
Yeah, well, you know, you touched upon it in the intro when you highlighted the fact that I focus on the human side of money. And for me, the reason for doing that is because I do come from, you know, the very technical side of it. I have my MBA in finance, I worked in investment management, managing money for high net worth individuals. So I've got the, you know, the quote unquote hard part, the numbers part down. But I also know that if success with money were purely a mathematical equation to be solved, that everybody would have more than they wanted or needed. Because at the end of the day, two plus two is always going to equal four. And yet that's not the case. So why is that not the case? Why is it that people don't have the experiences that they want? Why is it that they don't get the results that they want? And so there's something else going on beyond the numbers adding up. And I know from experience that in order to get to that something else, you have to go beyond the numbers, which means you have to tap into getting a better understanding of your emotions and the motivations that drive all of that. And so that's how I blend it all. Like, definitely respect the numbers, but also endeavor to have an understanding of why do you do the things that you do. And for me, you know, I probably, if it weren't for the crash of 1987, who knows, I may have been that kind of person who was, you know, hard nose down and just focused on the numbers too. But what I saw up close and personal was how because of the crash of 87, there were some people that I saw who responded to that. And if they could have jumped out of a window without exaggeration, they would have because of the amount of money they lost for themselves and for their clients. And then there were other people that were really calm and that just those drastically different reactions fascinated me. And while, you know, I'm I at the time I was still green behind the ears, just 21. It planted this seed of wanting to have a better understanding of what behavioral economics and behavioral finance was all about. So that's how I blend it all. Because I know that there is something more to it than just the numbers. But on the flip side, going to the piece that you were referencing, I also think that it is not healthy to just think that you can mantra your way onto the other side of a financial challenge.
That's a brilliant tagline. You can't mantra your way to the other side. Yeah. And even when I was in at seminary for the semester and a half, there was a lot of talk about prosperity Gospel, how there's this long history of connecting ideas that really may or may not need to be connected in that way. Like prosperity gospel is, oh, financial abundance is this birthright and we're only just a prayer away. And I think in the new age money manifesting, that gets said a lot as well. And I know you take a different stance than this. Oh, well, if you just think it into existence, it will happen. Or, or if you just don't ever have a negative thought about yourself or about money, that's the only thing getting in the way of your abundance.
Yeah. That drives me crazy.
Totally.
I. I feel like, you know, yes, you, you do. You, you, you are better served if you have a, A positive mindset. Yes. But I don't think you can force it. I think you have to get how you get. There is a process. So one of the things that I always say is that mindset is the perspective that you have, but it has to be supported by action. And so since you mentioned seminary, you know, one of the, One of the adages that I really love comes from the Quakers. And I'm sure there, there are similar. The, the sentiment of the proverb is probably throughout all religions, but the Quaker, Quaker proverb is when you pray, move your feet, which means that you have. There's a duality there. You can't just ask for something and not do it.
I love that. There's also. What is. There's one. It's like trust others but tie your camel to the pole. Something like that.
Oh, I love that one too.
Yeah. Of course I'm butchering it. Yeah. It's always this middle path. And even Tosha Silver talks about parabda, karma, where it may or may not be in your path, your destiny in this lifetime to be incredibly financially rich. And no amount of manifestation energy is going to change the trajectory of what your soul needs to learn in this lifetime. I mean, that is a more spiritual take on it. But nonetheless, it was such a refreshing perspective on this because I think some of the money mindset and manifestation world is like, sky's the limit. Just as Tosha says, just create your grocery list for God and, you know, don't get served up. Yeah.
And, you know, here's the other thing. Right. And I love my industry, and so I feel like I can also be critical of it. And the other. The thing that kind of rubs me the wrong way about personal finance as an industry is it is marketed as Though everything is on your shoulders. And so even though, even when I say you don't manage money, you manage choices, some would probably view that and think that I'm only talking about individual choices, but I'm not. I'm also talking about systemic choices. What are the choices that, you know, financial institutions are making? What are the choices that our lawmakers are making when it comes to policies in place? Because there are so many examples, examples of people doing all of the right things and yet not moving forward. And they're not moving forward because of anything that they've done or not done. It's because of some of the systems in which they work and how those things kind of stunt their progress.
Absolutely. And I think this is such a hard line for, or let's call it a tricky tightrope, that people walk of wanting to take responsibility for their earning and saving and financial, the math of money, as it were, and their own inner game around it, while recognizing the larger systems that we're all part of.
Yeah. And I think, I think the problem is. I say problem, but it's a nuanced. It's a nuanced situation. Right. It's a nuanced conversation. It's a nuanced set of. You've got to. I think you've got to take a nuanced approach to dissecting all of that and figuring out, well, what is my role and what am I responsible for and what can't I control and perhaps how can I influence it? But unfortunately, so much of our culture is focused on microwave sound bites that kind of omits those nuances.
A big part of this is pricing. And I know you teach a quarterly pricing workshop that I want to ask you about your approach to, even, even from a behind the business perspective of launching that quarterly and how that's helped you plan those launches. But from the PR pricing side, this also seems like such an area where all of our, you know, you're a behavioralist, so you talk about the psychology, the emotions of money, and particularly our own confidence and self worth, I think really comes into play when we're pricing. And a lot of people I know price too low and then it leads to burnout or even at some point, resentment of clients, even though they don't want to, but they're just feeling strapped. And then on the flip side, we, we all know there are those coaches that tell everybody to raise their prices all the way up through the roof to the point where sometimes it seems kind of ridiculous to me what people are charging and I'm like, are you possibly delivering that value? And do you feel good about that? And I w. When I. I know for me, there's this Goldilock Locks number in the middle. I'm so curious how you teach it, but when I'm pricing too high, I don't feel good about that. Um, and I think we each have our own internal gauge for that. But I also know it's an area that can get really fuzzy. And maybe, who knows, maybe what we think is too high is just our own limiting beliefs around pricing. So how do you walk people through that sweet spot when it comes to pricing their services?
So I tackle pricing looking at it from three sides. The financial, the emotional, and the personal. And in order to do that, what that requires is that you look at your relationship with money, your relationship with yourself, your relationship with your business, and your relationship with your people. Your people being your prospects, your clients, and your customers. Because all of that comes together to have an impact on how you both react, right, to the number that is either quoted, that is on your website, that's in your proposal. Like, both of you are bringing all of those sides, if you will, to how you are responding to that number. And the thing that I'm really trying to get people to understand is, first, the universal question of what should I charge for? This is just that it's universal. The problem is people expect, because the question is universal, that the answer should also be. And it's not. It's very unique. And I love using this example of, you know, I live in Brooklyn. I go outside my home, I make a left. There's a coffee shop on the same side of the block as me. If I cross the street, there's another coffee shop. Shop. Like, I literally could walk out of one door and into the other door. If I cross the avenue and make a left, there's another coffee shop, and at that corner, make a right, there's yet another coffee shop. Well, guess what? In less than five minutes, I go to four coffee shops. Those proprietors all had to weigh in the question of, what should I charge for this? And they came up with different answers because they need money to serve a different role for each of them in their business. And I think that's part of the challenge when it comes to pricing. Like, we're benchmarking our pricing against perhaps a peer in our business, but we don't know what they are considering. I don't know if the person on the same side of the street as me, I don't know if they own that brownstone and they're just using the bottom part of it for their commercial purposes or if they're actually paying rent, like, I don't know, there's so much that I don't know. And so therefore there's so much that we don't know about what other people are doing. The second thing is, when it comes to pricing, I think the mistake that people make is on one level, pricing is very binary. You either get it right or you get it wrong. And you know, when you get it wrong, you may not feel it immediately, but in short time you do, because sales are not flowing, you're not cash flow positive, you're not profitable, and at some point you're going to realize, I've got to do something. On the flip side though, you can actually have a profitable cash flow positive business and yet you yourself are broke. And people sometimes like dismiss the fact that their business is not there just to be successful on its own, that it needs to also translate and show up and have a healthy impact on your personal finances too. So if your business is doing well, but you're not paying yourself, or you're not paying yourself consistently, or you're not paying yourself as much as you could giving how well the business is doing, and that's not an intentional choice, or you haven't begun to replenish the savings that you invested in the business to either start it, take it to another level, help get it through a rough patch, or if you haven't resumed that long term investing that you put on pause and you thought you were only going to do it for a short amount of time and now more time has passed. If any of those things are what you are experiencing, what then that really means is that you only got it partially right, you didn't get it fully right. And I make no bones about the fact that I think that one of the best business decisions an entrepreneur or small business owner can make is to lead with their personal finances when it comes to their business. Because then they will by default include in how they approach their pricing, in how they set up their business model, in their sales process, the needs of their personal finances as well, but not just what you need right now, also what you need in the future.
I love that. And it's funny because I think in some circles this will be labeled a lifestyle business, where you're thinking about your lifestyle needs and wants and then setting up your pricing and revenue and products offerings accordingly. And in my mind, what other kind of business is there? I mean, I Guess there's venture funded startups that purposefully don't turn a profit so that they can grow and gobble everything up and have these winner take all network effects. Okay, but if you're not doing that, I don't understand. But I guess a lot of us do it unintentionally. I've certainly been through phases of this where we almost become a martyr within the business, like, oh, it's all on my shoulders and if I hustle a little harder.
And, and, and the, the thing about the martyr piece is that you end up unwittingly giving your business everything, including your future. And talk about getting yourself set up for burnout and frustration.
That's so powerful. Right? And what, what do you say then? What, what would you say some of the biggest mistakes people make when pricing. Is it that they're not pricing high enough or they're not taking. Like how would somebody know if they were on the road to burnout in terms of their pricing?
Well, I think one of the ways that you can figure out whether or not you're on the road to burnout is to, you know, look at. So one of the things I have people do is look at your relationship with your business and there are several questions that I'll have people ask. So like draw a timeline. So we're in 2021 now. So the far right hand side of that line is 2021. Then you've got 2020-2019-2018-2017. What were your revenue in each of those years? And if you weren't in the business at that time, then put an X. So that's the first question. What was your revenue? The second question is how well did you feel supported by your business? On a scale of 0 to 5, do you feel really supported by your business? Not supported at all.
What were the challenges that you had in your business? Were they operational challenges? Were they challenges to your growth? What were you most proud of? And then look at what is the pattern or what's the parallel that you see between those years when you earned a lot and those years where you felt most supported, those years where you felt most proud. And when you look at the years that you've had some challenges, what were those years and what's the connection? And that will give you a some insight into burnout. And, and if you were feeling burned out, then that is definitely an indication of, well, what if you did in fact increase your prices so that you could actually do less and therefore experience no burnout.
I love, I know you do Coaching, even your first book was for couples, if I'm not mistaken. I love thinking about our relationship to our business. And of course this is your professional training as a behaviorist and you talk about the psychology and the emotions of money, but you are the first person and it was in a text chain you probably remember a year ago and you were asking yourself all these interesting questions of if the business were personified by a person in your life, who would it be? Or how does your relate our relationship with our parents impact how our relationship with our business? And this is mind blowing just thinking about the business as a relationship in our life and the questions that you're asking, what are the patterns? What are the connections? Where am I getting triggered by my business or where am I? It's not correct to say blind spots anymore. So I don't have a good, I need to replace it and I haven't yet. But what are the areas that the unknown unknowns, certainly.
How's that?
What'd you say?
I said the areas you don't see so clearly. Not significant. Succinct, but.
Right. The unknown unknowns, the ones that are hiding that we don't even know to look at.
Right.
And because I also think people might. Oh, pricing. It's just pricing is such a doorway, isn't it, to so many things because it can be practical, but it can also be so psychological.
Oh my God. It's so one of the reasons why, you know, I, I've always done this, this scope of work in my one on one coaching. But I, one of the reasons why I pulled it out out was, you know, pulled it out meaning like made it, created a talk around, it created an offer around. It was because of the power of pricing. Right. It is that lever that can truly make the difference between having a business that's thriving and then that sets your life up to thrive as well, or being in a situation where you're constantly worried and stressed out about money. And in order to talk about pricing, right, you're talking about money and therefore.
There'S all kinds of stuff that's going to come out in that regard.
So speaking of deciding to pull out this piece on pricing, I want to go behind the business a little bit. You have been in business, as I mentioned, over 20 years. We've all struggled, I think at different points. What services should we offer? When should we offer them? Can we stand the launch model or to do yet another launch with this pricing workshop in particular, how has, how has your approach been in terms of getting it to the people that you most want to reach. And I love when I was listening to your podcast, more than Money, I just loved hearing it's offered quarterly, the last month of every quarter, the last Thursday and the last month. You know, like there was just this cadence to it that sounded really easeful. And I'm wondering if you can explain your thought process of launching something without or I don't know if this was in your thinking or not. Just taking some of the pressure off of the launch model, knowing that you're going to offer it on a recurring basis. And how did you price your pricing workshop?
A couple of things. It started off first as a talk that I would give for boutique conferences that focused on entrepreneurs and small business owners. And then last. So actually, let me rewind. It actually started off as a retreat. Let me go back to 2019. It started off as a retreat and then it became a talk and then I condensed it and it became a masterclass. And the reason it became a Masterclass was hello, 2020.
And being, you know, looking for creative ways to replace some of the income from the speaking engagements that I quote, unquote, loss from corporate engagements, et cetera.
So that was the transition, if you will, started off as a retreat, then became a talk, then became a masterclass. And what occurred to me is that I did the first one in June of 2020, and it went well. And it occurred to me that again, you don't just think about pricing once. It ought to be an ongoing question. And so how do I tie this into the natural points at which someone's going to be looking at their business and their numbers and evaluating their pricing? So that's how I landed on the last month of every quarter. I landed on the second Thursday just because of timing. It made sense to me. And so that's the cadence, and that's the reason for the cadence.
And how did you think about pricing this pricing workshop?
So I thought about it in a couple of ways. One of the things that I always tell people is that every offer that you have has two jobs, right? There is the job that it has for the people that you've created the offer for. What problem is it helping them solve? What question is it helping them to answer? What desire is it helping them to fulfill or frustration that, you know, you're helping it go away. But it is also, it also has the job of playing a role in your business model. So where does it sit? Is it, you know, a lead generation offer? Is it a paid lead generation offer? Is it your signature offer or somewhere in between. So when I look at my portfolio, this is again leaning into my background, formally managing money. I tend to look at our businesses through the lens of a portfolio. So when I looked at my portfolio, I looked at the fact that I have the dinner series and that's 150. That's an, you know, an endpoint, if you will, a lead generation. And then I thought about this and I was thought about the audience and how it's focused on a particular discipline. And so I was like, yeah, let me just add another 250 to that. I mean, another hundred to that. And that would be appropriate for the role of this offer in my business model, the revenue that I want to make from it and how it then can support introducing someone to working with me in a one on one capacity, either doing an intensive or a long term six month speaking engagement. So that's how I backed into it.
I love thinking about your portfolio and something you shared on your podcast that I totally adhere to as well is just thinking about the assets that we're creating in our business and that each program is an asset and that we want to have a diversified portfolio. But also I love what you're saying is what's the path? And that you're inviting people along. I don't even call it a funnel anymore. It just sounds so strange and passive for the person who's participating or a future community member. But this path of, hey, come to a dinner, and right now they're virtual, come to a dinner, let's talk about these kind of intimidating topics. Great next step is this great next step is an intensive and at no point are you having to put the hard sell because you've created a very logical path that really invites people each step further.
Exactly, exactly. And that, that is precisely what I wanted to do.
You mentioned when you quote, unquote, lost all your speaking engagements, which of course I had the similar experience. March 2020 hit and for two years, like the books were just the slate was wiped clean of what was on the calendar for the next two years, all in one, I would say a span of two weeks maximum a month. And you've clearly pivoted beautifully during this time. What were you thinking in that moment and what would you say now in hindsight, this time of not having all of those client speaking gigs has allowed you to do. How have you grown or evolved in a way that you might not have otherwise?
So I think like a lot of people, I vividly remember where I was on March 12 and, and not only do I remember where I was on March 12, I remember the fact that on March 15, I was supposed to be leaving for speaking engagement. So I was like, holy crap, what is about to happen? And one of my business besties, Tara Newman, reached out to me, I don't know, maybe a week and a half into everything, and said, hey, I know your business must have taken a really huge hit. I was supposed to be taking my mastermind out of the country, and I know that pricing is something that they really struggle with. What do you think about coming in and presenting your pricing workshop? And I was like, that's fantastic. And I will forever be. I will be forever grateful is what I'm trying to say to her for a couple of reasons. One, the fact that she asked. Two, the fact that she paid me my full speaking rate, which was phenomenal. And because of that, it opened the door for me to go inside other People's masterminds throughout 2020 and teach what I teach around pricing. I. Even though I know a lot of people that offer masterminds, even though I've been in a few of my own, it never occurred to me to be that outside person to either supplement their current conversation around pricing or add to it. And so that opened a door that I had never anticipated before. And going back to what I mentioned previously about everything, having a role or a job in your business, it also helped to reorient the job that I gave speaking engagements in my business. So I hope that answers your question.
Yes. And how interesting that it did open this new door and a new audience that you wouldn't necessarily have thought of, but the serendipity popcorn, you know, pop.
Exactly.
And then you know when you're onto something because one leads to the next, which leads to the next. We'll be right back just after this.
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There's a phrase around pricing that you can't stand. Tell us what it is.
Oh, my God. It is the whole thing of charge what you are worth. Whenever I hear that, for me, it is nails on a chalkboard. And here's why. And I will completely own this on A personal level. I'm black. My heritage is Jamaican American. My ancestry is tied to people's humanity being connected to a dollar amount. So when people say, charge what you're worth, I don't know if they fully understand the visceral reaction that that creates for some of us. So there's that piece. I just hate it because of that. The other thing is, though, in addition to.
The worth that you're charging for is the value that you are bringing to the table. How are you helping someone answer a question, solve a problem, get a desire fulfilled, and how are you doing it in a particular container? And what are you bringing to that table for that? Your education, both formal and informal, your perspective, your. Your. Your. Your gifts, your skills, your years of experience. You're bringing all of that into this container that you have promised someone to help them get whatever it is you've promised to give them. That is what you are charging for. You are not charging what you quote unquote as a person are worth. And even if people don't mean to intend that when they say the word, word, that is how some of us, myself included, experience it in our bodies.
Thank you so much for sharing that and illuminating that for both. Both reasons. Just the history of a phrase like that, and it is so toxic when you slow it down and say it the way you did. Charge what you are worth. It's just, ugh. And as you said, with the historical component of that and, and, and the structural inequalities that have persisted in our society where how many people were not able to charge what they quote are worth? And still to this day, like, even the whole. As we're recording this Amazon fight at the union, and how much are people being paid and managed by algorithms? And it's like, yeah, it's just something really nasty about it. And thank you for shining the light on that and. And also reminding us it's not your worth as a person, it's the products or services and the value you're delivering to the person on the other side. It also reminds me, like, for now, a phrase that's really getting on my nerves is time is money. And it's like, there's no more capitalist phrase than this. And I feel that it's so ubiquitous in our society, as if it's just a given. Time is money. And I get where people are going, which is that they want to say, hey, your time is valuable. This podcast is called Free time because I want it to be a verb. Free your time. Right. However, your time is Your life, it is so much more precious than money. It is so much bigger than money. Your time, again, is your time is your life. It's your breath. It's your existence. It's. It's priceless. Yes. It is not money.
Yep.
We can both get on our rant. Get on our I love a good jacket rant when they come through your podcast. So.
Yeah, but here's the thing, right? And I think this ties into the. The theme of the title of the podcast and. And the theme of your intention behind it, as I understand it, is that your pricing, if you do it in a strategic way and you factor in things other than just what's the number that I need to hit? Like, how much of my expenses do I need to cover? It can actually put you in a position so that you can have more free time.
Yes. And in my context, that's free time to do your best work and free time and choice and autonomy. Jaquette, this has been so fun to wrap up. If you could give people one permission around how they approach pricing, what would it be?
Ooh, that's a good one. One permission. Ooh, I know what it would be. When you think of value and you think of, well, I want to be accessible to everybody. Give yourself permission, put yourself first. And if, quote unquote, being accessible to everybody means that you are financially sabotaging the health of your business and the health of your personal finances, that means you've got to think of something else. You've got to think of another way to be of service to the people that you want to be most of most service to. But don't sabotage your health, quote, unquote, in service to being available to people that may not be able to afford.
You so good permission to put yourself first when pricing, so many people don't even put themselves in the picture at all.
Even if they think they do. I always say multiply your rates by 3 because you have to pay taxes. You have to pay a team, usually. And then there's your time. So even what people think they're putting themselves first, actually multiply even that times three.
Exactly.
That's my rule of thumb. Jacquette, is this. This is just so delightful. As always, I wish people could see you because you are so radiant, but they'll go research you online, hopefully attend a dinner. Where would you like to send people to keep in touch?
Oh, my goodness. Thank you so much. I am active on social media. I know my dear friend Jenny does.
Not like Frankie Curmudgeon.
But I do love me some Instagram so find me on Instagram. And then also if you want to do do a free exercise to get either reconnected or connected for the first time to your financial vision, then you can go to Jaquette Timmons.com forward/wheel and that will help you to do that. And then it will help you to figure out and ask yourself the question, if I change nothing else about my business, can I fulfill what I've written on my financial wheel? And if the answer to that is no, you know what your marching orders are.
I love it. I will link to that in the show notes and be sure to check out Chakhette's podcast More Than Money and you I set this up but I never said it publicly. You actually have listeners. If you want to buy her a coffee, go to buymeacoffee.com Jacquette I'm just going to put it out there for you because I was going to buy you a coffee this morning and then I didn't want it to be awkward. So coffee with your name on it coming soon.
Thank you.
Thank you so much. Happy Omni almost 10 year friendiversary yes. Thank you everybody for being here. Listening. Happy pricing. If you've listened this far, you get a gold star. Thank you. Word of mouth is the most joyful way we can grow this show, and it helps us land interviews with the luminaries and insightful guests that you would most love to hear from. Please send this episode to a friend who might find it helpful, and for show notes and related links from this episode, visit itsfreetime.com while you're there, make sure you're subscribed to the Time well Spent newsletter. You'll get instant access to my Tech Toolkit, a continually updated list of all the software I use, along with the total monthly spend to run my business where no one works full time even me. Visit itsfreetime.com join remember, you are running the show. It's time for radical reimagining and everything is up for grabs. Let it be easy, let it be fun and build with love.
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