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Today we have an inspiring guest, Carrie Friedberg, joining Dave Wolcott on the Wealth Strategy Secrets of the Ultra Wealthy Podcast. Carrie is a personal finance coach with a remarkable story—despite having advanced education and a rewarding career, she found managing her own finances confusing and overwhelming. Through her journey, Carrie discovered that while many of us are high achievers in our professional lives, we’re often not taught the critical basics of personal finance, leading to unnecessary stress and anxiety around money.
In this episode, Carrie opens up about her own struggles, from living paycheck to paycheck as a teacher to feeling paralyzed by budgeting. She reveals how working with a financial coach transformed her relationship with money, blending practical routines with emotional healing. Carrie now helps others achieve the same stability, offering clear, actionable advice for reducing financial stress and building routines that last.
Whether you’re a busy entrepreneur, a high earner, or simply looking to gain control over your finances, Carrie’s blend of human behavior insight and financial literacy is both relatable and empowering. She emphasizes that anyone can achieve financial peace with the right support, honest self-assessment, and simple, consistent habits.
In This Episode
- The root causes of financial stress—and how to overcome them
- How to manage and anticipate periodic expenses to avoid credit card debt
- The importance of mindful credit card use (and why paying off balances monthly matters)
- How to align your cash flow and financial routines with your personal values and goals
Anything is possible with, with good support and being really honest with yourself. I think the qualities for anyone to learn how to manage their wealth level are being honest, open-minded, and willing.
Welcome to the Wealth Strategy Secrets of the Ultra Wealthy Podcast, where we help entrepreneurs like you exponentially build wealth through passive income to live a life of freedom and prosperity. Are you tired of paying too much in taxes, gambling your future on the stock market, and want to learn about hidden strategies for making your money work for you? And now your host, Dave Wolcott, serial entrepreneur and author of the bestselling book The Holistic Wealth Strategy.
Welcome back to Wealth Strategy Secrets of the Ultra Wealthy. I’m your host, Dave Wolcott, and today we’re digging into one of the true root causes of financial stress and why so many high-achieving adults feel behind with money. We were never taught the basics. My guest is Carrie Friedberg, a personal finance coach who discovered firsthand that even with advanced education and a solid career, money can feel confusing, emotional, and overwhelming. In this episode, Carrie breaks down the blocking and tackling of financial stability, how to plan for those surprise expenses that derail people, how to get control of credit card use, and why building simple routines can dramatically reduce anxiety and increase confidence. If you want a more grounded, practical foundation for wealth, one that combines financial literacy with real human behavior, this conversation is for you. Carrie, welcome to the show.
Thank you so much, Dave. I’m thrilled to be here.
It’s a pleasure to have you on the show today, Carrie, and I think the audience is really going to get a lot of value out of this. As we really uncover some of the topics I think that are really the root cause of a lot of, you know, challenges in building wealth these days. And, you know, not only for us as individuals, maybe in our 40s, 50s, but also as, you know, it all starts as young adults. And we all know that, you know, one of the most important topics we should be taught in school is financial education, right? But it’s just not really— it’s not really offered. I remember doing an accounting class back in high school, but that was really the extent of it. So, you know, I’m excited today to have you on to really help our guests and our audience really understand some different tactics around financial education as it pertains to some of the basics, you know, really the blocking and tackling with finances that sometimes we can get, you know, overlooked and things like that. So, so with that being said, in background, tell us a little bit about your origin story. You’ve got quite a diverse background, but how did you actually get into personal financial coaching?
Well, I was a client myself. So that group of people you were just describing in their 20s— so I, I was college-educated, actually. I also had a master’s degree, yet I was gainfully employed as a classroom teacher. Yet I could not figure out personal finance for the life of me. People would say things like, “Just write a budget and stick to it.” And quite literally my hearing would go out, I would well up with tears. I just didn’t know how to do that or where to start. I had, even by that point, 5 nieces and nephews from my older siblings, and I wanted to save money for them and take them on special trips or things like that. That was impossible.
I had desires to move to a nicer neighborhood, turn in my car, you know, for something that I wasn’t embarrassed to drive, all of these kind of 20-something goals. And I was paralyzed. I had an earning ceiling as a classroom teacher. So by necessity, I had to take on second, third, and fourth side hustles, coaching and babysitting and tutoring, leading outdoor education trips, but still the math didn’t work, and I was caught in this cycle of anxiety. I just always felt like the ground was going to fall out from beneath me, and I’m kind of walking in quicksand on a daily basis. So it was, it was a horrible way to live, and it didn’t make sense given that I had all of this education and I was, you know, a functional adult.
Financial change isn’t just math, it’s emotional, behavioral, and deeply personal.
And basically by then, every other area of my life, I was practicing a lot of yoga at the time. So I was working on myself and attending kind of transformational retreats. And I was living in San Francisco, so these things were available morning, noon, and night and on every weekend. And I was very interested in psychology and increasing self-awareness. And so I just thought, I have got to improve this situation. Like there has to be a better way. And so I set out on a path to educate myself. I read books and series of books and watched webinars. I hired a tutor off of Craigslist to teach me Quicken.
All of these things worked for short periods of time. I thought, I’m into it now, I’m getting it, I’m doing something. But then life would throw me a curveball, or I would make a mistake and not be able to recover from that, or I would stop doing it, you know, that I was but still basically by myself trying to work it out at my kitchen table. And it wasn’t until I hired my own financial coach that things started to change. I had never heard of a money coach, but a friend suggested it. I literally was like, what is that? This was a while back before there were coaches for everything imaginable under the sun.
And this was a person who helped me with financial literacy, literally the ABCs and 1-2-3s of the best practices, the core routines, what you should do and shouldn’t do, custom guidance for me and my situation, helping me fill out tax forms. It was very, very practical. At the same time, she offered amazing, nurturing emotional support and kind of sacred listening around past mistakes and regrets and support around making amends and cleaning things up. And I worked with this person for 2 years.
And it doesn’t have to take that long for people these days because, as we all know, technology has changed so much. But for me, the rote work of writing down every single transaction in a checkbook register for 2 years was what I needed to do to heal my relationship with money. And it really, really worked. It turned out it was an inside job. And that kind of holistic approach of addressing the emotional and spiritual side of money as well as the very, very practical changed my life.
And the changes were so profound in all of my relationships. I showed up differently, including my family of origin and at work. I negotiated for a higher salary and, and, and I was able to make the move and turn in the car for a different, nicer used car. And I decided to do the same counselor training program that my own coach had done. So, for me, it was the same skill set. I was still teaching but different content, different audience. Now, I was working with adults on the topic of personal finance instead of kindergartners.
Yeah. No, that’s an interesting background. And I reflect back to— we actually had Sharon Lechter on the show, CEO of Rich Dad. And we were talking about the Cashflow Game that Robert and her had created. And what’s interesting to me is when I was going through that, and we’ve had our kids, we’ve played that many times inside of our family. But you can really see the power of education, how someone who can be maybe the lower-paying job, right, maybe a waitress or something like that, actually get out of the rat race faster than, you know, a dual-income, two attorneys, you know, in a household, or doctors and things like that, which really underscores how important some of the really basic building blocks are, you know, like the book The Man from Babylon. If folks haven’t read that one, it’s just this simple concept of just, you know, keeping more than you spend, right? Those really simple things that somehow, you know, kids have a hard time really figuring out, you know, or they come across certain events like the car breaks down or unexpected things. And then, as you say, right, it’s hard to actually recover from that.
So then how can you start actually building assets along the way? So education is so foundational to this. And I also think, totally agree with you, I mean, mindset is 80% of the game and how we can actually cultivate really an abundance-type mindset and really let money work for us, let money flow to us, which is quite counterintuitive, I think, to most.
Mindset is 80% of the game when it comes to building wealth.
Yes, well, as we know, there are 100 opportunities a day to spend money, whether it’s at a stop sign, on an app, or all the automation we have in our daily lives, and then being out and about at work. Should I bring my lunch, or should I spend $20 for a salad? It’s relentless, right? And so it really, really takes some discipline, and possibly something has to give in your life. Look, I’m not in the business of cutting and slashing anyone’s lifestyle. Believe me, if that had been the way I learned what I learned, I would have ran for the hills and just kept my head in the sand. But it’s, it’s just about slowing down and remaining connected. And from there, anything is possible.
So once you’re aware of your own goals and core values, and then you’re analyzing by yourself if you’re able to do it. I am not like a do-it-yourself type. I’m absolutely a let’s-do-it-together, hands-on kind of learner. So then you can kind of massage your cash flow and your earning and spending and saving goals for today or this year and help them be more and more aligned with your goals, your values, as well as your reality. So it’s an art form, I’ve discovered.
Yeah, for sure. So tell us, give us a couple of the top areas where people kind of go off track, or where are they missing?
Well, you named the number one game-changing lesson and distinction that changed my life and that can change people’s lives, and that’s around those pesky periodic expenses. So, a periodic is an anticipated, in an ideal world, an anticipated non-monthly expense, like a holiday, or a vacation, or a tax payment, or a car repair, or something with your animals, or children, or home. And these are the things that typically end up on a credit card if people haven’t literally put cash aside in a separate, contained savings account or allocated the funds in some other way ahead of time. So that’s what causes people stress. It kind of knocks them off their budget or their spending plan.
But what I learned is that most of those things can be anticipated. In other words, the simple skill is to map them out over— on a chart. It can be done by hand, it can be done on a spreadsheet where you have each month of the year, and you have— and I’m happy to share this with any of your listeners— a list of typical periodic expenses. We’ve already mentioned several. And then you write down, well, I know my annual insurance payment is every February. You record that amount. So there are several things that you can look up and map out.
And then, you know, any car owner should have at least, I think, $1,000 for a cracked windshield or a new tire, or— and some people might even say that amount is low per car. And so if you don’t know the exact payment date or when these things are going to happen, but you want to build that buffer, you can just kind of tuck that number into December, say. The point of this exercise is to get the grand total of these extra expenses for an entire year, divide that number by 12, and that’s how much money you, quote, should be putting aside into that savings account every month. So it actually is within your control, but it takes a little work, a little learning curve there to get organized around it.
And that changes people’s lives. And I work with a lot of high earners and tech executives and their families here in Silicon Valley, and most people don’t do that. So this is about education, being an outlier, and trying something that your friends and neighbors are not doing.
Yeah. So it’s very akin to being a business owner and doing accrual-based finance versus cash-type accounting, right?
Yes.
You’ve got that one payment that comes, yeah, on an annual basis. But if you can split it out over the month, you can really forecast and really try to normalize these things, you know, so it’s not so lumpy all the time.
Right, exactly. And that removes the emotion out of it and the kind of pain point or the sting, and it’s easier to recover and just say, okay, then X, Y, and Z all came up this month, but I handled it. You know, I anticipated that, and so it’s less surprising and easier to manage and easier to make those payments.
Yeah. Okay, any other, big mistakes that people are making?
Yes, so heavy credit card use is the other major pitfall. So by the time people hire a money coach, it is safe to assume things are not going well, right? Now, they’re at the point where they’re even willing to spend money to get help with their money. So it’s a special kind of moment in an adult’s life. That said, I do have clients who just want to vet and verify that what they’re doing is practicing excellence in this area and that they’re hitting all of the essential routines and that they know all of the basics. So that can happen as well. But mostly things are a little bit falling apart.
What that looks like is an inability to pay down a credit card to zero every month. So I’m saying to zero, which is my advice is not paying only the statement balance, because then you’re paying for things that you may have charged 6 weeks ago. And my whole approach is about being as current and present as possible, much like a meditation. And so I suggest at the end of every month you pay all credit cards down to zero so that you can contain this month’s spending this month for your spending plan and budget. And then you start the next month with zero on every single card.
If you can’t do that, then that’s a sign that there’s an imbalance. That’s a sign that there may be overspending, and it’s all too easy to do on a credit card because instant gratification, tap to pay, wave your palm, all this type of thing. And like we were already talking about, the culture of constant consumption means that there are so many different ways to spend money all the time, and it really takes some muscle development and patience to wait.
And so I think when someone comes to me and they’re unable to pay off their credit cards to zero and they’re incurring those very expensive finance charges, which can be up to as much as 30% each month these days, I immediately suggest that they stop all credit card use. And I have literally heard gasps when I’ve made this suggestion, like people feel like it’s impossible. It’s just a bridge too long. That’s interesting— tell me more about that. You know, what comes up for you? And usually it’s around, “I’ll be deprived,” “I can’t do this,” “I can’t help my mom,” whatever the life circumstances are.
And so at the very minimum, I would recommend that people consolidate all new credit card charges to one active card. So another place where kind of magical thinking can seep in is when people are using multiple cards and they’re due at different times throughout the month, and they charge this there and that there, and there’s this kind of gambling feeling, almost like playing Russian roulette, and it’s just stressful.
It’s a really different experience to use a debit card, which is today’s cash. I remember I didn’t mention this before, but I also saw a traditional financial therapist for 6 months, and she immediately put me on a 30-day cash-only diet, which I was shocked and angry about. But it forced me to face all of my automatic charges, to interact with the world, get out of the car at the gas station, go inside, pay, return for the change. It was an exercise in slowing down and really turning the lights on.
So that’s the invitation with my suggestion to go debit-only for at least 30 days. And if you really want to make change in your life, try 90 days. So yes, credit cards can be a very slippery slope for many people.
Yeah. No, good recommendation. I like that because I think there are so many timing type issues in terms of charges and things like that. So paying it down to zero every month— that’s great advice.
But how would you reconcile, you know, some of those expenses? Because what I think is interesting is you’re bringing in this human behavior component— the emotions, values, and things like that. So let’s say you have an opportunity to book an amazing, unforgettable experience for your family that’s totally aligned with your values. You’re overspending for it, but you’ll figure it out on the other end. You might have assets, you don’t want to sell them, but it really aligns with your values. And we don’t want to completely restrict our lifestyle because every day is a gift. So how would you reconcile something like that?
So number one, if you can afford it, even if it takes, I don’t know, 6 months or some reasonable amount of time to pay it off, if you can afford it and you know that you’ll be able to pay it off by a certain date, then go for it. Absolutely.
And it sounds like this person might already be a healthy credit card user based on even considering a trip like that, and also having assets that they don’t want to touch but could be a rainy-day fund if needed. Those are all signposts that this person is a healthy credit card user. And my definition of that is paying down credit cards to zero every single month.
So if you know that about yourself, and that you are generally in control of your cash flow, then you get to have that flexibility. You can use the credit card for a specific, meaningful experience like a family trip. You’ve earned that privilege. That was the original design of credit cards— it is a loan, but if you can pay it back in full in a timely manner without stress or conflict, then it’s fine.
But that’s not the case for everybody. You have to know deep inside that you are in a stable or even affluent stage of wealth, and that you can truly afford that risk.
Yeah, for sure. So we’ve talked about on the income statement, we’ve really talked about, you know, periodic expenses and things like that, how maybe how to manage those. How about on the revenue side, right? I know many in our audience, they might get bonuses year-end, they might be running businesses and not really sure, you know, quarter to quarter. So actually income can be lumpy, which can be the most difficult thing to manage really from kind of creating a budgeting, you know, type of, type of plan?
Yes. So I work with a lot of people in that situation that whether seasonal workers or get quarterly or annual bonuses, and, and sometimes it’s not even as neat and tidy and, and, the timing of those, but similar to the periodic expenses spreadsheet for potential and fluctuating income, I would also suggest writing it down and mapping that out to the best of your ability.
And people that get, say, quarterly bonuses or even quarterly paychecks, they’re in a unique position to kind of organize their cash flow to pay themselves, say, a, a set amount. Let— I’ll just pick a number— $10,000 a month. And so when you get a lumpy payment I would immediately move it out of your checking account, right?
Just even though we can all transfer money back to ourselves with one tap on our cell phones, you want to have a barrier there, and you want to have a cash flow plan, a spending plan, so that you understand what your monthly number is. You understand when these larger credit card payments or periodic expenses are happening., and then you can decide to make an additional transfer.
You just want to be thinking forward rather than practicing rearview mirror accounting. So that’s my whole approach is about controlling the things we can and being as proactive as possible.
I know we actually don’t know when we’re going to get the bonus or when we’re going to get paid, but if you are connected to your money, say on a weekly basis where you’re looking at things, reviewing things, things, and importantly analyzing the difference between what you thought would happen and what did happen.
And if overspending occurred, understand the reason for overspending. So, those are the exercises of someone who has a conscious relationship with money, and it’s about kneading the dough.
It’s a living document. Your plan, your system, and it needs tending like a garden. Sometimes you gotta weed, but you definitely need to water on a daily basis. And so, I don’t mean to sound too woo-woo, but it is, it is an art form and, and it takes consistency. And that is the hardest part of all of this.
Yeah. No, I love that analogy. And, and really, like, I, I went through this experience really for 20 years. It was one of my biggest challenges is trying to figure out how can I identify more capital to free up to start investing into cash-flowing assets.
And, you know, I’d be planning for a certain month or quarter, and then my wife would like have some surprise, you know, expense that would come along, or the kids, right? I mean, yes, you know, raising families, trust me, I know how hard that is for those listeners out there. You got kids in college, or, you know, whatever, they have all kinds of sports expenses, things like that.
But I’m really excited in our software program Pantheon Wealth OS, we’re actually able to track a complete personal financial statement. So you could take your income and expenses and actually look at your net margin.
So how much, you know, investable do I actually have at the end of the month? How much am I keeping for myself? So let’s say you’re able to keep an extra $10,000 a month.
And now I can run a forecast out for the year and say, hey, I’ve got $120,000 that I could actually deploy into investable asset this year, right? And then try to get that passive income number going, right? So that you have less reliance on your actual active income that’s coming.
But getting visibility into those numbers has always been so challenging. I’ve had so many different spreadsheets, so many different ways to look at it. But now we can actually forecast that we have visibility to it. All of the data is automatically populated. And then that knowledge becomes power.
Oh, I’m thrilled. That sounds awesome. And that’s amazing and really, really important to have accurate data for any kind of investment or asset, you know, conversation.
So, I’ve met a lot of financial planners over the years who have loose numbers for that piece, the monthly or annual spend. And that causes their clients stress. So good for you. I, I think it’s really important to be standing on a solid foundation with accurate numbers so clients actually know how much is available and they can trust the process, trust their money, trust you.
And then of course what we want for them in the end is to achieve their goals and feel happy and confident in their financial lives.
So Well, yeah, and again, I love your analogy of the garden, right? Because in my view, right, people who are just using QuickBooks, right, or not, not QuickBooks, let’s say Quicken, right? All they’re doing, or other Mint, whatever platform you want to talk about, all they’re really doing is creating a budget, right?
Which is so one-dimensional. Yes, it’s going to solve one problem, like you said, now, now I can kind of plan for my income and expenses and everything that’s called for one problem.
But I, you know, especially the listeners and this audience, right, I mean, that are very successful entrepreneurial, right, we’re really trying to get like CFO level or CIO level input and advice to start saying, hey, let me run a cash flow forecast, right, for the next 12 to 24 months, right? What does cash look like, right?
Because I may have cash, but do I want to deploy it? Or I want to deploy it at the right time when that right opportunity comes available. So we’re always creating velocity with our cash right, that we actually have.
Because, and then in some cases, right, actually having too much cash is a bad thing, right? Because, you know, now we’re losing from, you know, it’s eroding value in terms of debasement of the dollar, inflation, things like that. We want to be putting our capital to work, but trying to balance those things, right?
Yes, yes. And it all comes back to financial literacy and feeling empowered that you know how to take care of of your actual cash on a monthly and annual basis and beyond, how to save for the future, how to take steps towards manifesting your dreams, even, you know, taking the emotional risk to say, where do I really want to live? Who do I really want to be surrounded with? How do I want to be spending my life energy on a daily basis?
I remember I got a call one time from a potential client client, and she was very emotional. Single woman in her 40s, and her second parent had just passed, and the inheritance had just hit her account.
And she called and was crying in this first phone call to me, a local financial coach, and said, I have $500,000 in my checking account and I have no idea what to And it was really an interesting rite of passage moment for her.
And the important thing was that she was asking for help. So, I really want to emphasize how important it is to build out your financial support team. And there may be more or less active members on it at different phases and times in our lives, but I think people absolutely need to surround themselves with other people who have solid, successful relationships with money and have what you want. Learn from them.
Take their advice. Hire them if you can and need and want to. Even that custom expert advice around taxes. I used to try, I used to like wrestle with TurboTax myself, and I am not someone who was born with any kind of money gene.
Like I said, when someone said, just build, create a budget and stick with it, it was like hearing a foreign language. I would like actually go catatonic and just, you know, completely check out.
But when I finally stopped wrestling, and you may be laughing because I know TurboTax in essence is like very, very easy for many, many people, but not for me. And when I finally like knocked on the door of, at first it was H&R Block before I hired a personal referral, an amazing accountant.
Accountant who I now have a 2-decade relationship with, and he knows the ins and outs of my life, and that has definitely worked to my advantage. But when I first knocked on H&R Block and said, help, I don’t know what to do, I don’t know how to do this, I keep making mistakes on my tax forms year in and year out, I always owe money, I can’t afford that, like, that changed my life.
Anyway, I just want to say for the everyday person that you are not expected to already know this or figure it out by yourself.
Yeah, Carrie, let’s get back to the behavioral element of wealth. And have you ever noticed that there’s a typical set point for people with their wealth, with their net worth, with their income?
So some people might be, you know, maybe they receive something like $500,000, but then all of a sudden they spend it and then they get back to right where they were. We often see this with, you know, pro athletes, things like that. They make a ton of money, but then they end up actually ended up worse than where they are, or lottery winners or things like that.
So what would be your viewpoint on, on how those people could, could really avoid that?
So again, you need to build out your team. It’s really important that you trust and respect your financial advisors. In my book, I have a list of the basic questions you need to ask a financial advisor, and I’m happy to share those with anyone. You are not expected to know the 40,000 tax laws, and you probably don’t have all the licenses like Series 7 and others.
Whether you’re a pro athlete, an elementary school teacher, or whatever your lifestyle is, you need to get expert advice from people you trust. That’s a process—it can cost money, and it takes time and energy to interview people and connect with different advisors. Sometimes you can find a firm that has all these services in-house, which is also amazing.
I think anything is possible with good support and being really honest with yourself. The qualities for anyone to learn how to manage their wealth are being honest, open-minded, and willing. It’s not like you’re going to hand everything over to a professional and never deal with money again. In fact, the more wealthy people become over time, or as life events happen, the greater the responsibility to stay educated, connected, and continue learning about what’s possible in finance.
If you could give just one piece of advice to the audience about how they could accelerate their wealth trajectory, what would it be?
I would emphasize managing credit card use as well as possible. Adults, including myself, go through phases. There are times when I am fully able to pay off our credit card—my husband and I have one joint family credit card—and we pay it on time and in full. In fact, I might even make weekly payments just to keep things current.
When we fall behind because of spending, life events, or a dip in income, it’s about having the self-awareness to recognize that things are a little off or imbalanced. Then having the support team and the financial literacy to know that you need to slow down and get back into your routine.
That might mean returning to a weekly categorizing routine. Even if you have a bookkeeper or software, most financial tracking tools are not 100% accurate. They usually operate around 85% accuracy, which means you still need to review things yourself. Since you’re the one making financial decisions day to day, you need to make sure everything is properly allocated and categorized.
Through different life stages—being single, getting married, having children, moving across the country—there are times when something has to give, and you need to pay extra attention to your money.
In the end, what I’m trying to say is that you need to stay involved at all times. This applies to both people in a relationship. I see many cases where one partner handles everything, but both individuals need to be empowered. You should have access to all accounts, understand what’s going on, attend meetings, and know what you’re signing.
Yeah, great. Really appreciate all the insights and wisdom today, Carrie. If people would like to learn more about you, what is the best place they can reach out?
The best place to reach me is on my website, SFMoneyCoach.com. My book is available now on Amazon, Goodreads, and Strand Books in New York City and many other places. It’s called At Peace with Money. It came out two months ago, and I’m very proud of it. It’s the culmination of everything we’ve been talking about and much more, including my personal journey and stories from clients over the past 15 years. Those are the best ways to reach me.
Awesome. Thank you. Really appreciate your time.
Take care.
Thanks for listening to this episode of Wealth Strategy Secrets. If you’d like to get a free copy of the book, go to holisticwealthstrategy.com. That’s holisticwealthstrategy.com.
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