Financial Clarity as Leadership: Rewriting Your Relationship with Money with Joanna Tress

There's a quiet truth that doesn't get talked about enough. So many people aren't struggling because they're irresponsible with money. They're struggling because no one ever taught them how to feel safe with it. And when money feels unsafe, we avoid it, we delay it, we make decisions from fear instead of clarity. And what if financial stability wasn't about perfection? What if it was about building a relationship with money that actually supports your life? Today's conversation is about that shift, because leadership just isn't just how you show up in your business. It's how you steward your life, your choices, and your future. Welcome back to Catalyst Conversations, where we explore what it really means to lead with clarity, build with structure, and sustain with soul. And today I'm joined by someone who brings a deeply human, approachable lens to a topic that often feels intimidating. Welcome, Joanna. This is Joanna Tress. I'm so excited to have you joining us. Hello.

Thank you for having me, Desi. What a beautiful introduction to the topic, because you're right, we have a lot of fear, uh, confusion, scarcity, and just mixed emotions, ambivalent, uh, thoughts and feelings about money, which so many people believe makes the world go round.

Right, right. Joanna, I want to start here, not with what you do per se, but what shaped you? Because people don't step into financial education work by accident. What made you realize this is something people need help feeling safe around?

It's basically because at the time, um, that I started my career in financial services about 12 years ago, I was in a place where I needed guidance. I was approaching middle age, my first few gray hairs. My sons, or the 3 sons that I had as a divorced mom, they were teenagers. And with one income I had. So at that time, I saw what a difference I was making in people's lives by providing education. I was working with retirees. So these are people that worked for corporate America, large corporations, and were on employer plans. And then once they turned 65 and qualified for Medicare, okay, we're going to put you on the individual market because at that time it becomes a burden for the system. And they said, okay, we'll give you a couple thousand dollars for a healthcare reimbursement account, but go find. And I was there to help these people That season, there were over a quarter of a million retirees that my team helped to go from that group plan into the marketplace. And the conversations we had were so powerful with their newly limited income, on a fixed income now, the cost of their medications and certain treatments, and just understanding all those pieces. So that really was my foundation And I loved doing it. There was a need. I was helping people and educating myself too and really putting myself into the future. One day, this is going to be me in 20, 30 years. So what can I do so I'm not in a pitiful situation when I'm that age?

Right. Can we dive a little deeper into it? How has your own relationship with money evolved over time?

Oh my goodness, yes. I had a very unhealthy relationship with money. And that's because people hold on to certain ideals and notions that there's something moral and righteous about poverty, about being Mother Teresa, taking a vow of poverty, and helping the poor, and things of that nature. So I had a lot of conflicting things because of my background, you know, Judeo-Christian, biblical. Mm-hmm. background, a lot of people equate money and the love of money with negative things. Don't slave for 2 masters, God and riches, things like that. So the way that my neurodiversity works, I take a lot of things literally and maybe even to the extreme. So there was a popular rap group called Poor Righteous Teachers in the early '90s. I related. And then when I would acquire some, or like a mom with kids at tax return time, you know, and you can get a few thousand dollars, you know, it was gone. I would buy something nice or whatever, treat the kids or something. I was not building. And so, like so many people, I was living paycheck to paycheck without a sustainable plan. And divorce— Mm-hmm. Homelessness, joblessness, and health— physical and mental health problems— even slow the process down more.

Right.

So after a while, though, you get sick and tired of being sick and tired. And you're on this vicious cycle, like a merry-go-round. You keep going around, and you're reaching for that gold ring, and you never get it. Then you fall off the horse. You fall off the darn ride. And I got to that point, like, no, let me use a license, a professional license. It sort of levels the playing field because I did not get my college degree. And that always hung over me, you know, the sense of not being complete and, you know, being prepared, being worthy of a sustainable relationship of building wealth. Mm-hmm. I just— the buck stops here. And so, yeah, I started that journey still up and down, shaking with sea legs because there is an education component. But more than that, like you say, we cannot perform— outperform our own self-image. So, at the heart of my financial troubles was how I felt about myself. I had a very low self-esteem. On the outside, charming and engaging, and I looked confident and bold in ways. But on the inside, I was trash. And I didn't even have the motivation to give my kids more and to do better by them. Unfortunately, I was bringing them down with that mindset with me, doing the best that I can. Spinning my wheels. And a lot of times, it just wasn't good enough. And thank God that they love me and forgive me. We have a healthy relationship now. But that was really at the core. How do I feel about me? What do I think about me? Repairing that relationship with myself, that's what got me on the path where I am today, which caused us to cross paths.

Right. And living paycheck to paycheck, I mean, it's so— Worrisome and troublesome because if your income goes away, you don't have a paycheck to live on. Right? Right. And I think it's definitely contributing to the epidemic that's rampant in today's day and age. Right. The paycheck-to-paycheck mentality is— so I love this conversation. And what I'm hearing in this and what feels so important is that this isn't just about the numbers. Right. It's about the emotional experience. It's about the confidence. It's about whether people feel equipped Or overwhelmed on the reverse side of that, right? And I think a lot of listeners are going to recognize themselves in that. What I'd love to do is ground this in what you actually help people do, because I love how you describe your work as approachable and solution-oriented, and that matters so, so much in this space. Walk us through who are the people you serve primarily outside of retirees, because I did hear that, and what shifts them after working with you?

Yes. Well, right now, I'm focusing on people really where I am. It's in the middle. I'm middle-aged. So my parents are gone, but I have children and grandchildren now, babies. So you see these gray hairs? I'm not going to color them. This is real. You see, we're closer to retirement. OK? And so we're in the middle. Of our careers and our next business move. We're in the middle of our lifespan. We are in the middle health-wise. So I'm not running triathlons and prepping my raw foods diet for the week. But then I'm not so chronically ill that it overtakes my life. That mid-range income as well. So yes, I've been working. I have some income coming in. I'm married again. So my husband's income, of course, does the bulk of the work right now. And, but then again, we're not up here at the top in the highest tax bracket, etc. So in the middle, middle America, middle age, middle health, middle of your career, middle income, what can we do when we are within 2 years or less of retirement to make it count? It's not too late. So I have a practical approach to having life insurance and the different products that give you different results. Health insurance, there are certain— there are different types that are going to suit your needs. And then, of course, annuities, which are retirement plans. I've been working with teachers for the past couple of years, but there are such a variety. You take those main products And I help people with LegalShield, having access to an attorney. But we're leveraging these products and adjusting our lifestyle and our mindset to let us know, yes, I can afford it. Yes, I can squeeze out an extra $50 or $100 a month to augment my retirement plan. Yes, I can. And so I share practical tips on social media, the 5 major platforms under the hashtag #JoannasWealthAndHealth. To help people see, yes, I can do it. Practical ways, just fresh ways of thinking. And guess what? Not only can you, for a lot of people, you have to. You must. So that you really don't screw yourself in the future. You don't end up— I have a scenario. You're going to be homeless when you're 70 because you didn't have a plan starting in your 30s or things like that. Um, it's— this is reality. So, I'm here really to encourage and empower middle-aged people with how to maximize their returns and have a quality lifestyle, uh, when they're up in years and maybe not even able to work anymore. Sort of, you know, alternatives and multiple streams of income. That's what the wealthy people do. Leveraging life insurance is a great financial Equalizer. That's what wealthy people do. So it's like— So very true.

And I love that yes, I can mentality, right? It's such an important mindset shift, um, that I think a lot of people don't have access to, at least the tools to facilitate that mindset shift, right? Whether it be circumstance or how they were raised or what have you. Um, let me ask you this. What does financial stability actually look like in real life? Not just on paper, but in real life? What is financial stability?

That means that you have always money going into a savings account that's high yield and instantly liquid, or any asset that you can turn into cash quickly, but that's growing that interest. You have a retirement plan set up to supplement any pension or Social Insecurity, as they call it. You have, you have the funds available to take care of your healthcare needs, whether it's cash or a good health insurance plan, that you have the money for out-of-pocket costs. If you do, you're either going to pay more in services or you're going to pay a higher monthly premium to pay less out of pocket. You have that in place and it's manageable. You are able to pay all of your bills every month. And keep your, your debt-to-income ratio low. At the same time, you are working on your credit because you have a higher credit score. That means lower interest rates, and you're able to borrow money to build and create things and invest in things— businesses, real estate, of course. And so, um, those are the main options. And one— I'm not sure if I left anything out, but Life insurance, health insurance, retirement plan, um, you know, having access to an attorney for all the situations you face in life and business. Um, and again, multiple streams of income so that you can have your— let's say you have your day job and a couple of other things happening, because that's what it takes in the world today. One paycheck for the household, even one paycheck for each person When it comes to the statistics about what most people in America make, that's just not going to cut it.

Yeah. What stands out to me in this conversation is the way you bring clarity into something that oftentimes feels heavy. And then you create the structure, right, through budgeting, planning tools. But what really lands is the soul of it. It's helping people feel at ease and not judged. And that combination is rare. I'd love to go deeper into the idea of financial education as empowerment, because a lot of people avoid learning about money, not because they don't care, but because it feels overwhelming. From your perspective, what actually changes when someone becomes financially educated?

Then when they have these tools, their confidence in themselves rises, and they become really a different person. There's a type of swagger, pep to your step. There's that knowing and confident look that when you hear the experts on the radio suggesting things, you're like, oh, I've got that. Oh, I'm covered. Yes, I have a financial safety net that's actually helping me meet my goals instead of being full of holes. And that really is going to permeate every other aspect of your life because now, okay, I've got my finances under control, my credit. I have options, freedom. I can go beyond surviving and just having what I need to thriving and enjoying some of what I want. Most people dream of traveling And exploring things when they're older. But if they're doing backbreaking work and they don't have a solid plan that's growing and creating income for them, they end up hardly having the health to do it. They're still working and don't have the time to do it. And basically, they still don't have the money to enjoy decades of hard work. And that's such a shame. So when you actually put these tools into place for yourself in your life, and it's sustainable, you cover your bills, you have something to save, you have something to share, to contribute, to help others, and to pay yourself first when it comes to in the future, you know, your rainy day fund, et cetera. When you have these things in place, there is an ease about you. And you're just really— people, you're exuding positive, confident, vivacious vibrations. These— you're going to light up the room when you walk in it because you don't have this burden of worry upon you. So it really does change your life.

Right.

I'm thankful to have experienced that, me and my husband.

Yeah. What I'm hearing is it's not just knowledge. It's regulation. It's the ability to make decisions from clarity instead of panic, right? Fight or flight.

Oh,

yeah. Fight or flight. You also speak about resisting the traps of consumerism. And I think there is such an important leadership conversation here because we're constantly being told to upgrade, spend, and keep up with everyone else in the business environment, right? What do people need to understand about that cycle?

Yes, that it's not healthy. People create businesses and sell products, bring them to the market for fun, not necessarily because there is a need for it and that they're actually serving consumers with something that is going to improve their life. Do we really need all these brands? And there's this competition, and then you're being sold to all the time. You can't even be safe. I got off of social media because I couldn't stand getting sold to all the time. So this society, it's unhealthy. A lot of it is— it's based on greed. If, if, if the powers that be And the entrepreneurs could find creative ways to benefit the people who live on the planet instead of just finding more things to sell to them, which causes them to go into debt to afford them, which gets them into a trap of I owe, I owe, so off to work I go. This, this, the competition, the showy display of your means of life, you know, this glamorous lifestyle, you know, people Renting houses and cars just to take pictures and make it seem like they earned it somehow with their brilliant ideas. There are just so many dreams being sold and false stories, false narratives. The entertainment industry just pushing it— money, money, money. And it's really sick. It's a sign of the times that we're living in. And it's not healthy. We have all of the holidays that put people under pressure. I have to buy this and this and this. And if I don't buy my friend this fabulous birthday gift, they're going to think I don't love them. There's just pressure to keep up appearances. And people attach so much meaning to things. And the, you know, commerce and this capitalist free trade world and all of the options that we have, it's not going down. There are still more products flooding the market every day. And people want to get them and they feel they have to get them. I come from a background of performing arts, creativity, and being a producer of something that brings joy and happiness instead of a consumer. Of it. So yeah, we can get deep on that.

We could totally get deep on that. And I love that conversation. I mean, you speak about presence, and honestly, looking back at, at my childhood and, and how I've grown up, we always valued the most the gifts that were created by hand. And I think that holds true even more so now when we're, when we're in this world of consumerism. Making a gift is not just coming from the heart. It's— you're also putting time and energy and true effort into it instead of just, what can I buy them?

Yes.

Right? And that's so powerful because it's not about restriction. It's about intentionality. It's choosing alignment over impulse. And I want to talk about fear directly because money anxiety is real. And often unspoken. What's one thing you wish people understood about their fear around finances?

That it's artificial. It's an acculturated construct based on negative experiences, usually during childhood, involving lack of some kind, involving feeling a sense of shame. And seeing, okay, I guess the world is black and white with haves and have-nots. So, there are things tied into that. But really, the thing is money is a tool. It's an energy. It's simply an exchange of value. Once upon a time, the farmer over here who has this crop traded with the farmer over here with that crop. Right. Everyone had a craft and a trade of something that they were creating with their hands and could just trade with one another so they can all have what their family needed to thrive.

Right.

And so now we've replaced it with, you know, with economies and currencies. And then people said, well, you know, I don't want to just be happy with this self-sufficient village. I want to take over the world. And then, okay, and then they're— and so I just have a vision of life on this planet to go back to that original purpose for the human race, where we all have, have plenty of time and energy to create what we would like to create and help one another without the artificial construct that creates the fear, the scarcity, and even just afraid of the whole book. I was afraid to read Napoleon Hill's book, Think and Grow Rich, because something about it sounded unholy. Ooh. Like, ooh, greedy, love— you know, just— There are certain things you are afraid that acquiring money is bad. And of course, we love the blockbuster movie, right? Where a Wall Street magnet said, greed is good, right? So we just have confused messages. And that affects our perception and our feeling. And it's also sour grapes. You know, just, you know, the fox couldn't get the grapes. And so he said, ah, they're probably sour anyway. So people who have not been successful in achieving an income and a lifestyle that would make them comfortable, then they try to put a bad label on, on having the money. The only people that— most of the time, the people that say negative things about enterprise, business, multiple streams of income, wealth, and the safety net They're people who never had money. And so they give the whole thing a bad rap. But when you see professional athletes and people who win the lottery who go from millions to nothing within 3 years, that's real. Because I personally met someone who played for the Kansas City Chiefs and left with a little package when he got injured. And then I was helping him try to find a job in a manufacturing plant, slaughtering chickens or something. That was real. And he would go in his big, fabulous truck in the low-income neighborhood. And the women were, ooh, wow. Oh, he has something. Oh, he was a professional football player. No, he's trying to get a job right next to your brother Bubba to make ends meet. So that was sad. I personally have met people— who had a fortune at a time and lost it because of the education piece, not having good advice and guidance on what to do when they did have something, but then also self-sabotaging behaviors because of how we feel in here and in here.

Mm-hmm. Yeah, absolutely. I love everything about this, right? You work with people— and we've established it— that want to build something, whether that's homes, businesses, futures. And their financial structures around them. Where do people tend to misstep early on?

Some people are afraid of success. They are afraid that something bad is going to happen if they change the way that they think and see the world and see money. They might lose their friends or family. They don't want to rock the boat. They call it crabs in a barrel syndrome. You know, if you— so if you go to, right, the Maryland area, or, you know, Chesapeake Bay area and get those crabs, you put them in a bucket, right? When you go in with those tongs and try to get one out, have your gloves, what do the other crabs do? They're holding on. Hey, come back! Where are you going? You know, they don't know you're coming to get you. Take me with you. Right, right. That whole thing is like, no, no, you can't do that. So really, oh, oh, oh, you're bad and bougie now? Oh, you're not down with us in the hood? You know what? Oh, you don't like the down-home ways that we do things, the good old-fashioned? Oh, if this was good enough for your father or your grandfather, you know, who do you think you are with your edumacation and your big ideas? So there's a part of that. People are afraid of losing that comfort zone that they had. They're afraid that they'll change as a person and become a bad person or evil or greedy or heartless or lose touch. They're afraid of the unknown because it's a new and different world and a new way of thinking and interacting, you know, success. I mean, I know people that are bitter about failure in the past. And when they say the word success, there's such derision about it. What's wrong with it? So that's part of the piece of that puzzle.

And this is where leadership really becomes real, right? Structure isn't restrictive. It's honestly what allows your life to expand safely. And there's a topic that you brought up in one of our earlier conversations that I think is incredibly important and not talked about nearly enough— financial fitness in relationships. How does someone's financial reality impact their options in love and partnership?

Well, first of all, they might be looking for their partner to, um, to replace where they are, where they're weak. where they're lacking, instead of them being accountable and responsible and able to stand on their own 2 feet, whole and sound, and feel good about their own financial plan, they're hoping that their partner is going to do that. And of course, it's easy for women with our traditional roles. And I have to say, when I married my husband in February of 2020, I was tired of being a single mom. And he had a really good job. And he told me, you won't have to work. You can spend time healing and doing the things you've always wanted to do but didn't have time because you worked so hard. Well, guess what? He lost that nice cushy job with the pandemic when his company shut down where he'd been. So, aha! We started over again. Wow. So the point is that it's— you know, I say, God bless the child that's got his own. Like the Billie Holiday song. When you have your own, you are a complete person. You know what it takes to make it in this world. You know what it takes to have what you need and what you want, and the work ethic, the discipline, the mindset. And if you never learn those skills on your own, Then you're always going to need somebody else.

Yeah.

And that's just— and even as a single mom, I felt bad asking for any support from my sons. So yeah, I'm teaching them responsibility. But I knew that I needed it for myself. When I got married, and then my husband and I, we both lost our jobs. And 3 months later, OK, we were both back working again. But then I'm— oh, I started pursuing my dreams. I have a musical theater production. I'm singing and dancing and doing this stuff. And I'm spending money paying the band and the recording studio. I'm not making money with these dreams and ideas and things. And I put a burden on my husband. And then I said, you know what? I'm not trying to be a kept woman. I'm grown. I'm 53 years old. I'm a grandmother. I want to earn my keep. I want to prove to myself, I always knew that I could be financially successful. I always believed that I could be a 6-figure earner. I always knew that I could have multiple streams of income and put things together for myself. I'm smart. I'm talented. What's wrong? Mm-hmm. And what I was missing was the structure. So when you and I met in a structured environment, Where I'm accountable, I'm productive. I've got to count those, share those numbers, and watch my time and my energy, make those choices, my focus. Guess what? Number one, make money. Number two, you're going to help people because the way you make money helps people. You know, get that pitch together so I can present value to others. The things that I have learned with the structure has just put me in a different trajectory. And I find myself in the company with amazing people, brilliant, successful entrepreneurs who like to share their wisdom. And they keep coming back. It's the power of proximity. When you associate with people, you're taking things in. It's not just what they It's how they present themselves as leaders. And therefore, I know that I'm going to become as they are. And to a small degree, I have a little leadership, and I'm just building on that now. So that's what happens when you make sure that you're doing the same thing that successful people are doing. Instead of what you've always done before then.

Absolutely. And that's such a grounded perspective. It's, it's so heartwarming to hear, right? Because it's not the normal. It's— most people don't have that, that grounded of a perspective. But in reality, it's not about judgment. It's about choice. And when you're financially stable, you're not choosing from survival. You're choosing from alignment. And alignment is my favorite word.

Yes.

And I want to anchor into your core message a little bit, that it's never too late to become financially sound, because there are people listening who do feel behind, right? What would you say directly to them?

I would say educate yourself. I read a book called Killing the Sacred Cow. And, you know, it's based on a parable. You know, people say you need $1 million to retire. And then if you don't have $1 million when you retire, you're panicked. You're ashamed. You're embarrassed. You're scared. What am I going to do? But there are alternatives. There are gigs. There are things that you can sell. I mean, in the world of technology, we have markets and enterprise and opportunities that didn't even exist 20 years ago.

Mm-hmm.

So it's called open your mind. Be curious. Be open to doing something maybe that you've never done before. Explore. Find people that you can trust. I hope that my social media content creates in people a feeling like, you know, I think I can talk to Joanna. I think she's been where I am now. Let me have a conversation. That's the point. Find someone that you can trust. Get some information. Try it on for size. Try it. Do something. What a lot— there are things that you don't even have to invest money in first.

Mm-hmm.

If you're going to sell something on eBay, if you're going to drive Uber, just for, you know, a few hours a week, just a few items that you're selling a week, that, you know, $25 at a time, $50, $100 at a time, those little things add up, you know, and you start getting creative. What do I— What can I do? Can I be a personal care assistant? Can I help somebody clean up their house or take them to the doctor's appointment or something? You're saying, what's in my closet that I can monetize? So where, you know, what, can I be a consultant? You start thinking and opening up and coming up with those creative ideas. And you're not able to create and think of solutions when you have that constricted scarcity mindset of fear. So having a positive, abundant attitude that, yes, I can get out of it. Yes, there are resources. Yes, there's advice. There are ideas. And I'm willing to try it. I'm going to do what it takes. I'm going to grow as a person. Yes, I'm going to take some risks. It's not time to relax and chill yet. All right?

Right.

Relax and chill After you have the structure in place and have a plan for the future.

Right. And there's so much freedom in that because clarity, clarity doesn't require a perfect past. And perfect, in all honesty, come on, it's unattainable, right? Perfect is what you make it. Structure doesn't require a perfect start. And sustainability doesn't require that urgency. It requires consistency.

Yes.

What I love to do with you, Joanna, is shift into a quick lightning round. I love lightning rounds. You know, these are first instinct grounded answers. Okay. Ready?

Here we go.

What's one financial habit everyone should build immediately?

Save 10% of what you earn.

What's one belief about money that needs to be unlearned?

That it's bad.

Love that answer. What does financial peace look like to you?

It's peace of mind, heart, body, and soul, freedom, and options to do what you choose.

What's one small step someone can take in the next 24 hours?

An inventory of what they own. Just add up and then commit to filling the gap. Just commit to yourself you're going to fill in the gap.

I love it. What does living in alignment with your future look like?

That means that you have a sense of confidence and peace and joy because you know that you're on the right path.

I love it. What stands out to me so much in this conversation is that financial leadership isn't about having everything figured out. It's about being willing to look at your reality clearly To create the structures that will support and not restrict your life and to build a relationship with money that feels sustainable. That's where real freedom comes from. Not avoidance, not urgency. Here's my favorite word again, alignment. Right?

Yes.

Joanna, thank you for being such a grounded human approach to this conversation. Before we close, where can people connect with you and continue learning from your work?

OK, well, Joanna Tress is my name. And you'll find me on Facebook, LinkedIn, YouTube, TikTok, and Instagram. My website, joannatress.com. I'm sure it's going to be up and running by the time your dear listeners hear this. So look me up, J-O-A-N-N-A T-R-E-S-S.

I love the way you said that. And for the listeners, if this conversation resonated with you. Here's your takeaway. Okay, you don't need to have it all figured out to begin. Clarity starts with awareness. Structure starts with one decision. And sustainability starts with choosing your future on purpose. And we'll see you next time on Catalyst Conversations.