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Understand That Money Is Not Something You Manage w/ Jacquette Timmons

entrepreneur interview

This month is all about SALES! 💸

How to make sales easier, 

Why sales don't feel good to you,

And how to overcome your negative feelings about it...

And when we talk about sales, we have to naturally talk about pricing, and I have the perfect somebody here today who focuses on the human side of money. ❤️

Meet Jacquette Timmons, a financial behaviorist and an EXPERT on pricing. 

Jacquette is an author, coach, keynote speaker and is a wealth of knowledge.

I'm so excited to share all the information and help all of us learn how to price ourselves, so it feels in alignment with what you want and DESERVE.

Jacquette is gifting us a free exercise to get connected with your own financial vision here ➡️

Watch The Full Interview! 

Full Transcript


Jen: Hello and welcome to today's interview. I'm super excited to share with you an expert on pricing. Jacquette M Timmons is here today, and I'm going to tell you about her in a minute. But before I do, I want to remind you what we're talking about this month is sales. How to make sales easier, why sales don't feel good to you, what to do about that. And when we talk about sales, we have to naturally talk about pricing. And I have somebody here today who she focuses on the human side of money. 

And what does that mean?

It means that she's a financial behaviorist, and she's committed to getting you to keep your money is not something that you manage. It's something that you make choices. And she's incredibly accomplished. I'm not going to go through all of the stuff that she has done, but she is an author. She is a speaker. She is a coach. She is a keynote speaker. There's so much information that I know she's going to share with you today.

So I just want to welcome Jacquette Timmons, Welcome. And I'm so excited to learn from you because this is the problem most people have. How do we price ours so that it feels good?

Jacquette:  Yes. Thank you so much, Jen. I'm really delighted to be here today.

Jen: So before we get too into it, what the heck is a financial behaviorist? And Let's talk about that.

Jacquette:  Yeah, I'm always prepared for that, because it is a term that is relatively new to a lot of people's ears. But as you mentioned in your intro, I focus on the human side of money as a financial behaviorist. What I'm doing is getting people to pay just as much attention as they do to their numbers, to their behavior, to their choices, and to the motivation and emotions that drive all of that.

If that still seems a little abstract for people, I like to use this as an example to help people wrap their arms around it. Let's just presume that I gave everybody listening a dollar, and I said, “Hey, come back to me in 30 days and tell me, what did you do with that dollar?” Some people would come back and say that they save some or all of it. Others would say that they invested some or all of it. Another group would look at me side-eyed and be like, “Girl, please, you gave me a dollar. What do you think I did with it?

And yet there would be another group that will still have that dollar, maybe in the same place in their wallet. And the thing is, any of those choices are valid choices because you would have made them based upon the context and the circumstances that you were weighing at the time that I gave it to you.

That is why we focus on the behavior because success with money is not just a mathematical problem. 

Jen: So it's not a one size fits all solution. There's not a one size fit problem.

Jacquette:  No, not at all. Not at all.

Jen: Let's talk about your expertise. How exactly does your expertise help people?

Jacquette:  It helps them to give themselves permission to evolve. Because one of the things that I say is that your relationship with money is one of the longest relationships that you will have in your life. 

You can be married to somebody for 70 years, right?

So let's presume you got married in your 20’s and you're with them for 70 years. You still would have made financial decisions and choices. And you will have developed financial habits and financial beliefs long before you got with that person. And those are going to stay with you forever, right? And so as you go through life and as I alluded to as your circumstances change, as the context of those circumstances changes, the question, “What should I do with my money?” is always going to be there. But your answer is going to change, or at least it should change because the variables that you weighing have changed.

Jen: What I love about your approach already is it is inclusive. There's no one. As I said, there's no one-size-fits-all, but it feels gentle. It doesn't feel like should-y. Right? Like you should. You should. You should.

Jacquette:  Yes.

Jen: That feels so good to me.

Jacquette:  Yeah. Thank you.

Jen: And it also feels kind of expansive because you're saying wherever you started and where we are now and wherever you're going, it doesn't have to be linear. It doesn't have to be exact.

Jacquette:  Well, yes, I'm glad you picked up on that. And it's so true. I mean, what about life is linear, even if you just look at nature, what about nature is linear? And then also referencing nature, regardless of what it is, it ebbs and flows. And so if you think about the rhythm, how do you pay attention to what your rhythm is when it comes to money? And how do you lean into it when the rhythm is in an ebb moment or a flow moment? And how do you step back and observe and take some lessons when it's in a moment? 

Jen: Without judging.

Jacquette:  Exactly. Yeah.

Jen: So good.

Okay. I love that there's a lot of permission happening here. There's a lot of making it personal happening here. So when people find you, and whether that is through your books or your podcast or services that you're offering, what have they been struggling with?

Jacquette:  Oh, my God. It could be anything.

So as you mentioned, I have three pillars to my business. I do one-on-one coaching, mostly with entrepreneurs and small business owners. I'm a for-hire speaker, mostly for Fortune 100 to 500 companies and law firms. And then I self-host events, a dinner series, and a pricing master class. So let's just focus because I know your audience is probably more in the category of entrepreneurs and small business owners.

So let's just focus on that.

They're probably struggling, I should say, with living a business owner’s version of paycheck to paycheck. They might be struggling with they're really, really good and they are an expert in their particular domain of discipline, but not as good as they'd like to be when it comes to running a business. And so that kind of chips away at their confidence. It could also be that they are struggling with, and this leads to the pricing they're struggling with, how do they either expand the market that they are in or get into a new one and do that in such a way that it's sustainable? So those would be like, I think the three key things that people are struggling with that pricing can help illuminate if you will.

Jen: Okay. So when people get to that point, you really laid that out clearly, but what causes us to get to that point where we're struggling with any of those things?

What have we not done, or done?

Jacquette:  Some kind of shift happens, whether it's a business shift, whether it's a personal shift, something changes in their life. And whatever that change is, it forces them to think about “I need to be doing something differently.

And they may not know precisely at the point of asking that question what it is that they should be doing differently, but something changed. So maybe they had a child, or maybe that child has gone off to college, or, like, a major transition. Or maybe they got married, maybe they got divorced, maybe their partner lost a job. Or maybe there's a relocation. Like, it could be any number of things.

But there is typically a life event that occurs that forces them to take a new look at their business. And then there are times when a business shift happens, maybe they lose a major client, or maybe they reach a point of burnout, and they're like, “Oh, God, I just can't do this anymore. I can't do it like this anymore.

Or maybe they are, you know, having a conversation, be it casual or formal with some of their business besties. And they're looking and they're seeing that everybody is, quote, unquote, “doing so well”, and they don't feel like they are measuring up. So something happens.

There's a triggering moment that causes someone to say, “I need to reevaluate what's happening here. And I might need a third set of eyes or a second set of eyes to help me with this.

Jen: Yeah. It's so true. We don't take any action until we're really, really uncomfortable.

Jacquette:  Yeah. Yeah.

Jen: So basically, when people come to you, they know something needs to change. They're not sure how. They don't know how. Pricing is involved, and that's your expertise. So that's really where I want to head next is let's talk first before we talk about the house of it all. But, like, why is this idea of both money and pricing so hard for us as small business owners?

Jacquette:  Because it's money, because it's money and because it's emotional. And contrary to probably how most of us have been trained, are typically especially when it comes to pricing, are probably instructed to look at it as if it is really a logical-mathematical problem. Right?

So you take A, you add it to B, and you get the result of C. 

Jen: What's so hard about this, right? Why is this hard? Right?

Jacquette:  Right. Except for the fact that it excludes the emotional element, it excludes the emotional element for you. It excludes the emotional element of your prospects, your clients, and your customers. And so whenever you're dealing with pricing, you are inevitably dealing with money, which means you are inevitably dealing with emotions. And you need to at least be aware of that influence so that you can make sure that it's working for you and not working against you.

Let me just pause here and say, “It's not about getting anything perfect, but it is about amplifying your self-awareness, because the more where you are, the more than you can be.  in the front leading as opposed to being in the front being pushed by”, because I always say you're in the front. The position is that you are always in the front, but the posture, are you standing in the posture of leading, or are you standing in the posture of being pushed by?

Jen: Can you expand on the posture being pushed by a little bit deeper?

Jacquette:  Yeah. So, you know, pushed by is really reactionary. So you've got a situation where maybe you are not selling as much because I know sales is a theme for this month. So maybe you're not selling as much. And so your reactionary solution is well, “Let me drop my prices and let me make that up in volume.” That's reactionary, right? So that would be an example of being pushed by. 

You're not being strategic. You're not taking a long-term perspective. You're not looking at what impact this particular decision is having on your future. 

Jen: So I'm guessing that behind the pushed-by model, fear is driving that.

Jacquette:  Totally it's fear. And, you know, I just want to pause here and say that I don't think fear is a bad thing. I think it's how we relate to fear that can get in our way. So to me, when it comes to fear, I know this is going to sound crazy as all get out, but I think it's helpful if we actually think of fear as our friend and ask the question of, “What are you trying to protect me from?

Whatever your answer is, you can either say, “Okay, I got that covered. I can move on,” or “Okay, I didn’t think about that.” 

And I'll tell you if it's okay to take a moment to please share a story of how I came to that perspective around fear.

This is going back many years ago, but it has stayed with me forever. I had gone down to Tortola to do my check-out date dives to get my scuba certification. And for anyone that's unfamiliar, you've got to do. I think it's either seven or nine dives. I can't recall at the moment, but each dive gets more complex in terms of the skills that you are demonstrating and you go deeper. So I was going for my certification for 90 feet.

The first dive, everything went well. Second dive, not so much. The second dive, I did a side of a backward, I should say, a backward flip off the side of the boat, and my goggles came off, my regulator came out, I was just completely discombobulated. Calmed down, finally got underneath the water, finally did what I needed to do.

But when I got back on the boat, the master, who was a woman, which today wouldn't be such a surprise, but back then, which was in the 90’s it was a pretty big deal. The divemaster said to me that's the best thing that could have happened to you. She said the day you get on this boat and you are not a little bit afraid is the day you should not go diving. And her point to me was because the first dive went so well, I got a little cocky. And so I didn't do all of the things that I should have done in terms of doubling and triple-checking to make sure everything was working.

So from that standpoint, I think that fear can, not sometimes, is our friend, but it's on us to take the lead and ask, “Are you pausing me from doing something because I'm afraid? Or are you pausing me from doing something because I've missed a step? And this is the tap on my shoulder to make sure I do that step?

Jen: I love that. I say to my husband sometimes before I teach a lot. I do a lot of these interviews, but every time I'm always a little nervous beforehand, and his take is very much like yours. Like the day that you're not afraid, that's the moment you should be like “Check-in with yourself, Jen. You got a little too cocky.

Jacquette:  Yeah, totally, totally, totally, totally.

Jen: So on this main of talking about money and pricing, what could we be doing better? I actually wrote this question when I first wrote it, too. I was like, What are we doing wrong with our pricing? But I think to tweak it, getting your vibe is, what could we be doing better with our pricing, our goods, and services?

Jacquette:  So there are a couple of things. One, you know, one thing that makes pricing hard is that we should always ask the question, ”What should I charge for this?” The problem is because it is a ubiquitous question we often think that it should be the same when it comes to an answer.

And as we've already talked about, there is no one-size-fits-all.  Right?

So I love to use this example of I live in Brooklyn, and if I walk outside of my home on the same side of the street as me is a coffee shop directly across from that is another coffee shop. If I cross the Avenue and make a left, there's a coffee shop. And at the corner I make a right, there's another coffee shop less than five minutes outside my door.

I've got four options. And guess what? At each of those places, black coffee is a different price. When I want to treat myself to a dirty chai latte with some oat milk, that too is a different price. And I use that as an example to illustrate for people that everybody charges differently for a variety of reasons, and you don't know what those other reasons are.

So the thing that makes one of the things that makes pricing hard is the question is ubiquitous. The answer is very personal, but we are often looking externally for benchmarks around what we should be doing with our pricing so that's something that we can get better at.

The other thing that I think we could get better at is on one level, pricing is really binary. You either get it right or you get it wrong, right? When you get it wrong, though, it comes to your attention very quickly because either you don't have sales flowing, you're not cash flow positive. You are not profitable, and you might be able to flow like that for a month or two or three or maybe even a little bit longer. But at some point, you got to do something about it, right? Something tapped you on your shoulder and said, “Hey, you need to look at this.

When you get it right, it's a little harder to see because you can be cash-flow positive. You can be profitable. Sales can be flowing. And you're like, “Yeah, I got this.” But if I want to ask you the question, “Are you paying yourself? Are you paying yourself consistently? Are you paying yourself as much as you could be given how well the business is doing? And if you aren't, is that an intentional, strategic choice?

If you used any of your personal savings to either start your business or to get it through a rough patch or to help take it to the next level, have you replenished, or have you started to replenish those savings? If you put any long-term investing on pause, have you begun to do that again? If you've answered no or paused to think about “Am I doing that?” That means that you don't have it fully, right.

And one of the things that I am really on a mission about if you will, is to get business owners and entrepreneurs to see that actually one of the best business decisions that you can make is to start with the health of your personal finances. If you integrate that into how you approach your business model, your sales process, and your pricing, then you will always make sure or be in a position I should say, more times than others had a thriving business and a thriving life rather than a thriving business and a life that has you struggling. Or struggling business and struggling life, and that's financially, that's energetically, that's creatively. It's all of those different realms.

Jen: So it's kind of like clean up what's happening in your home first or in the personal finances first, and then it's much easier to make decisions about pricing for your products and services.

Jacquette:  Yeah. And I don't know if I would say clean up what's in your home first. I would say be aware of what's in your home because I walk people through an exercise, and when we're done, what they have done is they've created their financial vision. And so I then asked the question, “If you change nothing about your business, could your business help you fulfill that financial vision?

Nine times out of 10 people say no and on the rare instances where I think one person said, “Yes.” I'm like, okay, “Are you comfortable with how long it would take?

So if you know what you want money to do for you and your personal life, it is so much easier to then make sure that you are setting your business up in order to make that happen. 

Jen: I just want to repeat what you said, and I want to make sure I get it right. Do you know what you want the money in your business to do for your life? That is a question that I don't really think I've ever heard anybody overtly ask because we jump into business ownership or entrepreneurship.

We do this service that we're really good at. We hope we make some money, especially at the beginning. And we never ask, “How is it in service to what we're trying to build?”  It's just sometimes it's really wrapped up in ego. Like, am I just making money? Like, I'm not even thinking about where it's going to plug into my life?

Jacquette:  Yeah, exactly. And I want to change that. 

Jen:I love that. This is such important work. So at the beginning of our conversation, I mentioned to you. A lot of people, my clients, people I know in entrepreneurs, they avoid things that will bring them sales, whether that's consistent content, following up with people putting offers out there, having calls to action, whatever it is, because they really hate doing sales.

So in your expertise, what have you found is the relationship between doing sales and pricing. And what do you notice about how that affects people?

Jacquette:  Oh, my goodness. So here's what I want to offer up as an exercise for people to think through on that regard. As I mentioned, or I think I mentioned, when I am looking at pricing, I'm looking at it from three sides. The financial, the emotional, and the personal. And in order to do that, we've got to look at what's your relationship with money, with yourself, with your business, and with your people.

To answer your question, I think the exercise that's really illuminating is your relationship with yourself. And the exercise that I have people do, it's called five and five. So the first five represents who are the five people that you spend the most time with? And I know we're still, at least here in New York, we're still in pandemic mode. So you're not spending a whole bunch of time with a lot of people that are outside your pod. But even if you think about it in terms of who are you spending the most time with virtually? Who are those people? What's the nature of the relationship that energizes you, who depletes you of energy? That's the first five.

The second five gets a little more interesting because these are the five people that are just running around in your head, right? So they can be people that you don't even know. Personally, it can be people that you do know, but for whatever reason, you're not on speaking terms. Sadly, it can be a loved one that has passed on, but they are running around in your head influencing what you think, how you think, what you say, what you do, et cetera.

So make note of who those people are. What's the nature of that relationship? How do they energize you? How do they deplete you of energy? And then if you were to say, “If my business were a person, which of these relationships would it most reflect? If how I engage in the sales process, which of these relationships would it most reflect? If I were to think about my approach to pricing, not the numbers, but just the approach to pricing, which of these relationships would it most reflect?” 

If people are like, “What?!” Let me say this. And especially since we're talking about pricing. When I did this exercise for myself, what became really evident was that how I was relating to my pricing was really related or correlated to my relationship, or lack thereof, with my father.

And so when I felt like, “Oh, my God.” And my father has been deceased for many years, but when I felt like, “Oh, my God, my father wasn't embracing of me, et cetera.” And then I think about the sales process and how I would get all upset when someone either didn't make a decision or would take a really long time to make a decision. Or just the follow-up process felt really awkward because I felt like I was asking them to accept me. Like I was asking, like, you people don't see those connections, but they are clearly there.

And again, it's not about perfection, but it's about being aware so that you can then create boundaries for yourself and ways of managing and coping. And so because of that awareness for myself, I have a process in place so that I don't get to the point when we're in the sales process and we're following up or in the follow up process that I then began to take personally, something that has absolutely nothing to do with the person on the other end of that potential business commitment.

Jen: This is the kind of stuff where you have to press, pause, get out a piece of paper, chart some things out, and also look at some garbage that's going on in your brain about this junk. For me, it wouldn't necessarily be my parents, although there's a lot of junk there that I've worked through, it's that I used to be a high school teacher, and as a high school teacher I had to have a master's degree.

I have a Masters degree, plus enough credits to get another master's degree. And I felt lucky to be making $32,000 a year. 

Jacquette:  Right.

Jen: So when you go to charge... “What's my program going to be, what's the pricing for my program?” And you're like, “Am I really worth that?” That was the work I had to do.

But this is I'm so glad you shared it and really laid it out for us. And give us an example, because I don't think enough people are actually taking the time to make these correlations.

Jacquette:  Yeah, I agree with you.

And I want to piggyback on the translation of a number when you were working as a teacher, and now when you are on your own and you get to declare what that price is. Number one, I also want to disavow of the phrase “Charge what you're worth.”

I really, really dislike that term.

Jen: If you don't have good self-worth, how do you do that?

Jacquette:  Well, if you don't have good self-worth, true. But then also, I take it to another level. I'm obviously black. People will see that my heritage is Jamaican American. I have an ancestry where people's humanity was indeed tied to a number. So when you say charge what you're worth, I wonder if people really recognize the visceral reaction that that creates for some of us.

So that's one reason why I don't like it. The other reason is you are focused on the wrong thing. The word is in the value that you are bringing. The value is in what's the promise that you're making? What's the container of that promise? And what are you bringing to that container in terms of your education, both formal and informal? Your expertise, your experience, your skills, your perspective. That is what someone is paying you for, your ability to help them answer a question, solve a problem, address a frustration, address a desire, and you have packaged it. And whatever container that is, that's what they're paying you for.

That is what you're charging for. That's the value.

And that's the thing that you are “worth-er-ing” if you will. I don't even know if that's a word.

Jen: I love that you just made up a whole new word. I have never heard it put that way before, and it's incredibly helpful.

Jacquette:  Yeah.

Jen: Thank you for that.

Jacquette:  Yeah. You're Welcome.

And I think alongside that is the idea of positioning.

Where do you want to be on a spectrum? Because there's a spectrum, right? Do you want to be at the budget end of the spectrum? The standard, the mid-range, or the premium? And there's no right or wrong answer, but you need to know where you want to be so that you are pricing your services in accordance with that. Do you want to be at the steak house or do you want to be at McDonald's?

Both are making lots of money.

Jen: Exactly. In different ways with different audiences. 

Jacquette:  Different audiences, everything.

Jen: This is such a great conversation because it also requires us to look in the mirror and look at who we've been judging. So if our whole lives, we've been judging the luxury people and we think they're jerks are assholes, and we think that they're not in touch with everybody, you're going to have a really hard time aligning yourself with those people.

So there's so much to unpack here that, like, pricing is not just about what is everybody else doing. We already cleaned that up. It's like an inside job.

Jacquette:  It is. Yes. Thank you for pulling that out. It totally is, totally is.

Jen: You have been so wonderful. I wonder, is there a myth around this topic that you would just love to bust, like something that you hear all the time in your industry that we could end with?

Jacquette:  Oh, my goodness.

I think one you kind of alluded to. And that was the idea of when you share the example of transitioning from teacher to now having your own business. I think the way that that also shows up is when people want to make their services accessible And so that means that they're not charging a high enough price or they want to have a special price. Give yourself permission to take care of yourself first. 

So if doing that means that you've got to put yourself in a financially vulnerable situation, don't do that. Because then you're not even going to be able to be around to help those people that you want to help at a “discounted” quote, unquote rate.

That wasn't very succinct. I’m sorry. 

Jen: No, it makes sense,. Especially for people who I get a lot of people who are helpers healers, highly sensitive entrepreneurs. Their whole thing is about...

Let me give it to you. Let me overdo it. Let me overgive. And it's very hard for them to, and we've talked about this before this podcast, is received. I'm not taking care of myself and receiving I'm not going to be around to help any of you for very long. 

Jacquette:  Exactly. Permission to take care of you and your business first.

Jen: Thank you so much.

Then you tell us people I know are going to want more of you. What are the most accessible way to follow you read your books, listen to your brilliance. 

Jacquette:  I appreciate that if you are active on social, I love me some Instagram, so put my name in the search box. You'll find me on Instagram.

If you want to do a free exercise to get connected to your own financial vision, you can go to And if you are in a relationship, in a I'd highly recommend doing it separately, but then coming back and comparing your answers, because that can be a really good money date. But really, the point is to do that and ask yourself the question, “Is my business set up to help me do this?”

So that could be a way for us to stay in touch.

And I offer the pricing master classes on a quarterly basis. ( So you can head on to site and see if the next one if it fits with your schedule. And if not, you'll know that there's another one coming in another quarter.

Jen: I'm actually going to sure that your website is linked in all the places that this interview will be, so people could easily get to because I it is a thing to say, but it can be hard to spell, so I'm just going to it. J-A-C-Q-U-E-T-T-E and Timmons T-I-M-M-O-N-S. So if you're only listening to this on the podcast, go find Jacquette because I'm promising you need to do this work.

I don’t know anyone that doesn’t need to do this work. 

Jacquette:  Yeah. And it's ongoing. So that would be a thing to remember that your relationship with money is one of the longest, that you will have the work on it and with it never stops. And so let it be okay.

I mean, it's just like any other relationship in your life that is of significance and of importance. You don't ever stop working on it, that is with your money.

Jen: Oh, my goodness. Thank you so much for your time and your wisdom today. This is such a gift to us. I really appreciate you being here. Thank you. 

Jacquette:  And I appreciate being here. Thank you.

Jen: Thank you. Bye, everybody.

Jacquette:  Bye.

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