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The Leadership Blind Spot That Was Hiding in Plain Sight
In the world of high achievers, financial acumen is often assumed. But what happens when your leadership blind spot shows up in the very area you’re expected to master?
That’s exactly what happened to Jacquette Timmons, an MBA in Finance, a Wall Street veteran, and now a highly sought-after financial behaviorist and speaker.
In a recent episode of The Enlightened Executive, Jacquette shared a deeply personal, and professionally pivotal, story that sheds light on a powerful truth: even the most seasoned leaders can be blind to the patterns that hold them back.
When a Single Question Reframes Everything
Back in 2003, Jacquette walked into her CPA’s office feeling proud. Her numbers were strong. Her business was thriving, or so she thought. But what happened next shook her.
Her longtime CPA paused, looked over his glasses, and asked a question that stopped her cold: “When are you going to stop mortgaging your life?”
It wasn’t about real estate. It was about her behavior.
Jacquette had been regularly transferring money from her personal savings to cover business expenses: dipping into reserves, selling securities, even increasing credit card debt. It was a pattern she hadn’t even recognized. But her CPA had. And he called it out…not as a reprimand, but as a wake-up call.
That moment launched Jacquette on a path of deeper inquiry, not only into her finances but also into the unconscious beliefs and emotional patterns that shaped her decisions.
Why This Matters for Leaders
As Jacquette put it, “I had access to the same information as my CPA. But I didn’t have the distance or objectivity to see what he saw.”
That’s the challenge with blind spots. They don’t come from ignorance. They sit right next to your strengths.
In leadership, they often show up as habits that once worked but now get in the way. They’re reinforced by success and easy to overlook.
You might be a sharp strategist who over-functions and stifles your team. Or someone generous and dependable who unknowingly undercharges, like Jacquette did.
Blind spots aren’t flaws. They’re patterns. And recognizing them is more than self-awareness, it’s a leadership essential.
The Science Behind the Shift
Neuroscience shows that the brain prioritizes patterns because they conserve energy. Once a behavior becomes automatic, your brain stops questioning it, even if it’s no longer helpful.
But under stress or transition (like Jacquette’s move from corporate finance to entrepreneurship), those patterns get louder. They show up in your financial decisions, your time management, your communication.
In leadership, the more senior your role, the less feedback you receive. Which means the more critical it becomes to intentionally seek out those patterns and interrogate them.
Action Steps You Can Take This Week
- Ask the Hard Questions
What’s a pattern you’ve rationalized as “just how I work”? Ask someone you trust: “What’s one behavior I repeat that might be holding me back?” - Use Proximity and Distance
Just as Jacquette’s CPA offered an external view, consider who has enough distance from your day-to-day to see what you might be missing. Bring them into your reflection process. - Audit Your Financial Behavior
Even if you’re financially savvy, revisit how you make money decisions. Are they based on logic, or driven by unconscious emotional patterns? - Normalize Pattern Spotting
Encourage your team to identify leadership patterns in themselves. Use tools like the Enneagram to surface blind spots and shift from reflexive to intentional leadership.
Jacquette’s story is a reminder that success doesn’t immunize us from blind spots. In fact, it often conceals them.
But when you build the muscle of pattern recognition, when you train yourself to pause, zoom out, and name what’s really happening, you unlock a new kind of leadership.
Not just smarter. More conscious. More effective. More human.
Because the most enlightened executives don’t just fix problems. They see patterns. And they choose a better move.
For deeper insights on uncovering your blind spots, explore our Enneagram Applied program.
Episode Transcript
Susan Drumm: What’s a five-letter word that invokes infinite perceptions, that shapes or influences practically every decision a person makes or an institution makes? And much of life revolves around the use of it. Are you stumped? The word is money.
I’m Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership evolution. Each week we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life.
With us today is financial behaviorist, speaker, and CEO of Sterling Investment Management, Jacquette Timmons. For three decades, Jacquette has been exploring the intersection of money, business, and life through a cultural lens. Her aim is to help people decrease their financial stress and increase their financial health and wealth by focusing on both sides of the money equation: the numbers, and the psychology and emotions that drive them.
She does this by helping people transform their relationship with money, often the unspoken force that shapes every swipe, deposit, and financial choice. She’s the author of Financial Intimacy: How to Create a Healthy Relationship with Your Money and Your Mate, and is the host of the podcast More Than Money. Welcome, Jacquette. I am so excited to have you on the show.
Jacquette Timmons: I am so delighted to be here. Thank you so much for having me, Susan.
Susan Drumm: Yes. Well, let’s start a little bit with, how did you get into doing the work that you do today? Tell us about the journey.
Jacquette Timmons: Oh my goodness. I want to tell you about the journey, but I’m not going to tell it to you sequentially. I want to hone in on a particular question that had a huge impact on me, and it will give you a little bit of context as well.
So, one of the things that I always say to people is that you use money every day. But just because you use money every day — be it in the form of cash, credit card, digital currency — just because you’re making financial transactions, it doesn’t mean that you know what you are doing with what you have, or why you’re doing it.
And I bring that up because it’s 2003. I am going into a meeting with my CPA at the time, may he rest in peace. And I arrive at that meeting filled with enthusiasm and pride because I’m like, my numbers look good this year. So we’re going through the meeting, and he and his assistant are asking questions, and as we get to the end, he does three things that he’s never done before, and it really takes me off guard. And I don’t know about you, but whenever an elder takes their glasses and brings it down to the brim of their nose, whenever they point their finger at you, whatever comes after that is not going to be something you wanted to hear.
So he does that, and he goes, “Jacquette, when are you going to stop mortgaging your life?” And I am like, “What in the world are you talking about? I just came down the stairs all excited. I thought you would be happy with me.” And to even put this in further context, I had been working with him for 15 years at that point, eight of which had been with my business. So I am like, you know, a deer in headlights. I don’t know what he’s asking. I don’t know why he’s asking. And, probably even worse, I don’t have an answer to his question.
So I get back on the Long Island Railroad and I’m coming back to Brooklyn, and I’m like, maybe it’s time for me to get a new CPA, because I don’t know what he’s talking about. Fast forward two or four business days and I’ve got a business bill to pay. I don’t have enough in my business account to pay it. So, it’s 2003, we don’t yet have online banking. So I do what I had always done in situations like that: I go down to the branch and I get a withdrawal slip from my personal savings account, a deposit slip for my business checking account, and when I go to give both to the teller, that’s when the light bulb moment goes off. Because what I saw him tapping me on the shoulder about is this is your pattern: every single time your business needs money, you do one of three things — dip into your savings, sell some securities, or increase your credit card debt, which was not anything that I had before I started my business.
So when you talk about my journey, I share that story because — I have my MBA in finance. At that time, I had only ever worked on Wall Street, and I started in ’86. But I was in a very regulated part of the industry. What wasn’t regulated was the speaking and the coaching arm, and that is where I just woefully undercharged, and that put me in that situation where he’s looking at me like, what are you doing? And also, there’s a huge difference between working inside a huge house, where you get paid the same amount every month regardless of the market performance of your portfolio, and when you have your own business and you get paid based on the market value of the portfolios that you’re managing, and, oh by the way, a month later. So it was acclimating to a lot of different moving and changing pieces. And so that is a part of my journey.
Susan Drumm: Excellent, excellent. And so, how did that unfold from that piece — once you recognized something, what happened from there?
Jacquette Timmons: Well, I think what my story kind of taps into, or what I hope people will take away from it, is that we all have blind spots. Because I had the same access — I had access, I should say — to the same information as Mr. Beth did, right? I had my statements, I was using financial accounting software for my business and personal numbers. So it wasn’t like I didn’t have access to the information, but what I did lack is the proximity and the distance and the objectivity and the ability to see a pattern that he could so clearly see.
So I would say that’s one thing: he helped me to uncover my blind spots. We all have them. Questions, I think, are the way to tap into them. I would say that the other thing it really helped me to do is — even though I have been talking about the importance of people understanding their relationship with money for years and years and years — it was really that experience, and that question, and really then beginning to unpack, well, how do I answer it, that helped me to reexamine my own and rethink my own relationship with money, pricing, and business. And it helped me to also just bring a more empathetic tone to my conversations.
Susan Drumm: Yeah, well, I love some of the things that you’re highlighting here, because — as we talk about a lot on this podcast, and I like to bring into the work that we do — it’s about the patterns that are guiding our behavior. And if you want to make any shift in leadership or your results, it’s about shifting the pattern.
So here we’re specifically going to be talking about patterns related to our relationship with money, because we all have them. And what happens if you can, one, identify what that pattern is — because it’s blind to you typically, because you just think that’s the way it is. And so much of that usually comes from our upbringing; our beliefs, that our parents had around money, get passed down to us. We think that this is how everyone relates to money. So I’m really excited to unpack this with you, because I’d love to hear some examples of the different types of patterns that people have with their relationship with money. What have you seen in the type of work that you do?
Jacquette Timmons: Well, you hit on one, which is there is absolutely a familial pattern when it comes to money. And for me, one of the things that made — you know, Mr. with dude’s question and navigating it so challenging — was that I actually had all of the makings of, I should not be in this situation, right? My mother worked for Social Security, and so she wasn’t like rich or wealthy by any means, but we did okay, and she always taught me the importance of saving and not carrying any debt. So that was the familial message that I got.
But we also have to be mindful of the fact that there are cultural, and societal, and systemic messages that we get as well. So one of the things I always like to share with people is, I started my career at Bankers Trust in ’86, and when I started, I had a defined benefit plan. By the time I left, it was a defined contribution plan. And it was during that time when a lot of corporations were shifting the responsibility of retirement planning from them to the individual employees. So there’s a pattern right there that is shifting.
Another thing that was shifting is not only the shifting of responsibility, but also how we work. My mother was at Social Security for 38 years; I was at Bankers Trust for 10. The average length of employment now for most people is 4.2 years. So you put that into a container alongside the personal finance industry growing — because now people are responsible for their own retirement — and you’ve got all these retail mutual funds coming on the market, alongside the growth of personal development, like, you can do it, and this is what you need to do to do it. And you’ve got this convergence of things, and patterns of thinking that say: if you do these things — if you pay yourself first, if you invest, if you save, if you carry little to no debt — then you’re going to be financially successful. But what happens when those dynamics change? And sometimes you don’t have any control over those dynamics.
So the patterns come in a lot of different ways. It comes from a familial standpoint. It comes from what’s shifting in the economy, in the market. It comes from systemic issues — just in terms of how this country, or any country, communicates who has access to what, who can do what, and when, and where, and why. So all of those things are the patterns that we need to pay attention to.
Susan Drumm: Yes, absolutely. And so these are sort of more the global patterns. What do you see in terms of patterns of mindset — the beliefs, right — how people engage with money? “I can’t borrow anything because I can’t possibly go into debt,” that might be one, right, as an example. What do you see?
Jacquette Timmons: I see a number of different things — and working in the private bank really helped me with this. There’s this notion, for some people, that very wealthy people don’t have problems, they don’t have any money problems. And I can tell you that that is not true. So there is a pattern of thinking that people who have great means don’t have problems — again, not true. But there is also a pattern of thinking that says people who don’t have great means don’t know what to do with their money. That isn’t true either. They may not have access to as many avenues or outlets to do certain things, but it’s not that they don’t know what to do.
I work a lot with lawyers and law firms, and one of the patterns that I see there is: they are trained to be risk-averse — right, that is their job, mitigate risk for their clients — and that flows over into their process of how they make decisions when it comes to money, where they’re really laser-focused on what they can possibly lose but never consider the opportunity cost. And that’s a risk too — you have to weigh both sides.
I also see the pattern of making judgments — or being not only judgmental about other people, but also turning those fingers inside and being judgmental about what you do or haven’t done. And the reality is, at least from my perspective, that we all make the best choices that we can in any given moment. And sometimes we can look back and we may not like those choices, but you more than likely did the best that you could. And I always say that the choices are driven by the context and the circumstances that you were weighing at that time. So, given the same choice, what you do today you may have done differently five years ago, and you may do differently five years into the future — predominantly because the circumstances and the context of those circumstances are slightly different.
Susan Drumm: So those would be the patterns on a more local, individual level. Interesting, interesting. And so when people start to work with you, in what ways do you help shift that?
Jacquette Timmons: Well, one is getting people who don’t recognize that they have a relationship with money to see it — that is an important piece of the puzzle. But also, another piece of the puzzle is, I operate with the understanding that everybody wants to be successful, profitable, and not broke. But here’s what I mean by that: when I say successful, that you have what you want on your own terms without doing harm to anybody else. When I say profitable, that you have more than enough — more than enough money, more than enough time, more than enough space. And when I say not broke — yes, not broke financially, but also not broke creatively and energetically.
And for me, one of the things that I’m really on a mission to do is to disrupt, I would say, two key myths. One is that financial success is all about the numbers, when it isn’t. And the other is to disrupt this myth, for those of us that are entrepreneurs, that we give our businesses everything, including our financial futures. I want to stop glamorizing that.
Susan Drumm: That — totally, totally, I completely understand. And I think that it’s so hard to recognize that you don’t have to do that.
Jacquette Timmons: It is, because all the messaging around you says that that’s what you should be doing, because that’s a mark of success.
Susan Drumm: Yes. And I also imagine — to your second point, around having more than enough — that’s where I would see that there were lots of differences of what is enough. How do you work with that?
Jacquette Timmons: Everyone always says, “Well, but I don’t know.” And part of the reason is they’re using other people as their benchmark to help them back into it. So an exercise that I always walk people through is called the financial flywheel. And what it invites people to do is to think about, very broadly, the four things that you can do with your money: earn it, save it, invest it, and spend it. And when we’re thinking about investing it, we typically are very narrowly focused on the financial part of building wealth, right — owning a business, investing in the stock market, and having income-producing real estate.
Most people, though, don’t ask themselves the question of, well, what number will make me feel wealthy? What’s the valuation of my business that will make me feel wealthy? What’s the amount, when I open up my investment statements or go online, what’s the amount that will make me say I am wealthy? So people will often say, “I just want to be wealthy,” but they don’t have a number that we are aiming toward. So part of my work is getting people to feel comfortable stating a number, even though we don’t have any certainty that they will get it. And one of the things that I always say to people is, clarity is more important than certainty. And you’re resisting saying a number because you want it to be accurate — and it’s not about that. It’s about having a vision so that we can reverse-engineer: well, how do we get from point A to point B with this number that you have in mind now?
Susan Drumm: And what about the goalpost always changing? Because I’ve seen that too, right, where people — if only I had X number, but oh, now it needs to be Y. I got that, but I still don’t feel secure, right? And it’s also about the feeling — I don’t feel free — and it’s about the feeling that money gives you. What do you say to that?
Jacquette Timmons: And that’s one of the reasons why I say money is never just about the numbers, right — it’s the psychology and the emotional aspect of it. And I will never tell someone to question why they feel the way that they feel, but I will ask them to examine why they feel the way that they feel. And so if the goalpost changes — well, why did it change? Did it change because there were some dynamics in your life, in your business, in your profession that required a change? Or did it change because your neighbor’s thing changed and you’re trying to keep up with them, but you don’t want to admit that? So for me, it’s about examining the why behind it all. It can change, it might change, it might behoove you to change.
I always say to folks, I think it’s important to always ask the question: what should I do with my money? Or, if you are an entrepreneur, what should I charge for this? The red flag should go up if you’re not getting a different answer, and there’s been a great deal of time in between the questioning — because that means you’re not taking into account things that may have changed in your life, or your responsibilities.
And one of the things I also say is that, as you hit different benchmarks — I’m thinking of one person in particular, when we were working together, he came to me with an incredible milestone having been reached, which is that his business hit $10 million. So, woohoo! But he was feeling very heavy. And one of the reasons he was feeling very heavy is he had not adjusted to the new roles and the responsibilities and the expectations — not only that other people have of him, but that he has of himself — to match this new number. And so he met the goal but had not thought about, well, how do I need to change so that when I reach this goal, I’m really prepared for it?
Susan Drumm: Yeah. So two things are coming up for me on that. One is — I love this phrase that one of my own brilliant coaches said, Jocelyn Herman: people aren’t related to reality when it comes to money, meaning related to the reality of what they actually have, or shifting their state of being or mental model to match what reality is for them today. They’re still stuck in whatever mental model that they created five years ago, ten years ago. So one of the first things that’s so important with money is to get related to the reality of the present — of what it is today, and what that looks like. There’s almost a resistance, like, “I don’t want to look at that,” or, “Gosh, if I change, if I let go of what these expectations were, what will happen?” So that’s one big thing that I’m hearing what you’re saying.
Jacquette Timmons: And then another thing to piggyback on that is, sometimes people feel guilty, right? They have this goal, they reach the goal, and then they feel guilty about reaching the goal. I’m thinking of folks who have a lot of debt — they get out of debt and they feel guilty because they’re like, “Oh, what do I do now with all of this money? I don’t know what to do with it.” And it’s like, well, maybe if you had given that money a purpose, a plan. And I think it piggybacks on your comment about what your coach said with regard to reality — reality changes, and I think sometimes people think of reality as something that’s static, and it’s never static.
Susan Drumm: Yeah. And the other piece is: who you are while you’re making your money is pretty much going to be who you are when you have your money. So there is a question around, how are you feeling as you’re making it? Because I’ve certainly seen — similarly — I’ve worked with incredible leaders who have a major event, they IPO, they’re now a gajillionaire, and the same kind of problems that haunted them before — they may be different problems, but it’s sort of the same belief set that’s there, it hasn’t adjusted. So, yeah, I always think about that: who you are while you’re making your money is who you’re going to be when you have it.
Jacquette Timmons: Yeah, something that I often say to folks who will make a comment about, you know, so-and-so would be different if they had more — I’m like, if they’re stingy now, they’re going to be stingy with more. And if they’re gracious and generous now, they’ll be gracious and generous with just a little bit more. Money doesn’t change the essence of who you are; it changes what your options are. It changes, perhaps, some of the things that you were able to do — I guess that’s options — but it doesn’t change the essence of who you are.
Susan Drumm: Yeah, yeah. So what advice would you have for listeners right now? What are the things that they should start doing, thinking about changing?
Jacquette Timmons: I’m going to answer that on two different levels. One is — and I say this reflecting back on my own experience — experience, expertise, and education doesn’t shield you from blindness. And so one of the things that I think is really important is that you have — whether it’s someone that you are paying, a coach, a therapist, somebody who can tap you on your shoulder to help you see your blind spots — so whether it’s somebody that you’re paying, a professional, or just a really close inner circle of people that you can go to and be really vulnerable with, so that you can get out of your own way.
Because I know your podcast is all about being an enlightened executive, whether you’re working in-house or you’re running your own business. But when I think about how that relates to money — stress is invisible and silent, but its impact on your life and work are not. And so if you really want to be an effective leader, you have got to be aware of that stress and aware of the impact that stress is having, and have some systems and tools in place that will help you to manage it. I don’t believe that you can eradicate all stress, and sometimes stress is good, right — that’s good stress — but it’s the chronic stress about the exact same thing that can do a lot of harm. So I think being mindful of the fact that there are some areas of blindness — what do you have in place, in terms of people or systems or tools, to help you get out of your own way when you are in your own way. So those would be two things.
And then I think the other thing is — we talked about reality not being static — I think it’s also remembering that leadership is a skill that we’re constantly developing, and that also is not static. You don’t go to the gym one time and then be like, “okay, I’m done,” or, “I’m going to do work with a coach at the gym for three months and then I’m done, I don’t have to go back.” It’s a constant source of how you’re evaluating.
Susan Drumm: And so how often do you think people should be meeting with, let’s say, an advisor or a coach around money?
Jacquette Timmons: Well, if it’s an advisor, and it’s really about your plan, quarterly, twice a year — unless there’s a significant event that has happened. But if you are looking to change any aspect of your personal behavior, and especially your behavior when it comes to the decisions that you’re making about your business that impacts your personal life, I would say that you probably need that help on a monthly basis, if not a little bit more frequently than that.
When I’m working with clients, one of the things that I always like to make sure people understand is, I have the belief that your business should center the health of your personal finances. So we have to first have a really clear understanding of what it is that you want money to do for you personally, so that we are designing your business — your business model, sales process, pricing, operations, all of that — to support it. And that takes a little bit of time.
Susan Drumm: Oh, yeah.
Jacquette Timmons: Because, you know, looking at, okay, how are my prices conveying the positioning that I want people to view my business in? How is that satisfying the fact that I need to have a profitable business, but I also need that profitability to extend to me personally as well? That’s not just a singular conversation. So I think if it’s purely asset management and financial planning stuff, quarterly, or at least twice a year, or whenever there’s a significant event. And then if it’s anything else, it’s probably monthly, if not twice a month.
Susan Drumm: Yeah, for sure, for sure. So what’s one thing, like tomorrow, that you suggest people do regarding their relationship with money?
Jacquette Timmons: I want people to visualize a caterpillar. And the reason why I want people to visualize a caterpillar is the caterpillar doesn’t have to think about becoming a butterfly — it just happens. And the reason why I’m using that as a visual metaphor is the fact that we are always in transition. And the key is, how can we be more intentional about that transition?
And so when I think about, for example, what are some of the core elements — one is to stay connected with the reality that you have a relationship with money, and that relationship, just like any relationship in your life that is of importance, is going to evolve and change. And so, looking at your relationship with money, your relationship with yourself, with the people in your life — if you have a business, with your clients and your customers and your prospects — and recognizing that as you have experiences, as you have challenges, as you have new insights, all of that’s going to shift. And so be as intentional as you can about how you navigate those shifts.
Susan Drumm: Great, great advice. Well, where can people learn more about you and your work?
Jacquette Timmons: Jacquettetimmons.com is my website, and then I am pretty active on LinkedIn and Instagram.
Susan Drumm: All right, fantastic. So one last parting message for our listeners, and then we’ll let you go.
Jacquette Timmons: Okie doke. I think one of the things that I am really purporting is that people look at money through a human lens. And so if someone goes to my site, they’ll see that I talk about money from a human-centered standpoint. That’s very much the same with leadership — the most effective leaders are those that, in my opinion, have a very, very high EQ. And I think that translates well when it comes to money also. So when you bridge those two — and that doesn’t mean being perfect, but it does mean being connected — so that would be my last parting word: to recognize the humanness of both money and leadership.
Susan Drumm: Well, if you liked this episode, you’re not going to want to miss my interview with Petra Kolber, who’s also a mutual friend of ours, who is a two-time cancer survivor and shares why resilience and reinvention matter more than perfection for modern leaders. Let’s lead the way.
Hope you enjoyed today’s episode, and I’d like to point you to the next important step: hit the subscribe button and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.