Women & Money: The Shit We Don't Talk About!

Smart Year-End Tax & Retirement Strategy with Carolyn Rowland

Barbara Provost & Maggie Nielsen Episode 115

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The end of the year is your moment to take control of your money, not scramble over taxes.

This week, we sat down with Carolyn Rowland, CFP®, EA, Partner and Financial Advisor at Resilient Wealth Planning. Carolyn combines tax smarts with long-term financial planning to help women feel calm, confident, and in charge of their money.

In this episode, Carolyn breaks down the simple year-end moves that can make a major difference for your future, without the stress or confusion. She shares how to make your taxes work for you, the key deadlines that matter before December 31, and why small, consistent steps are the true secret to wealth building.  If you’re ready to finish 2025 strong, tune in to hear Carolyn’s strategy that sets you up for 2026 success.

01:02 Meet Carolyn Rowland

04:45 Pre-Tax vs Roth: Which is right for you?
09:05 Year-End Fixes That Boost Your Retirement Accounts
10:20 Quick Tax Tips Before December 31
17:40 Aligning Your Tax & Retirement Plans
23:30 Carolyn’s Definition of Financial Freedom

Carolyn shows us how to lock in retirement moves before year-end. For practical next steps and actionable strategies to maximize your accounts, reduce taxes, and protect your assets, join us on Oct 24th for Money Talks: Concrete Strategies to Maximize Your Accounts and Protect Your Assets. Click here to register for FREE and bring your questions! 

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Barb: [00:00:00] Taxes, Maggie.

Maggie: Listeners, do not drop. I know you heard taxes. Don't drop off right now.

Barb: Yeah, because taxes, it does sound kind of boring and dry, but you know what? There's nothing so sure as death in taxes, as they say. So we gotta learn about step into those uncomfortable situations and learn about. Taxes doesn't have to be scary, especially if you talk to someone like Carolyn who makes it so easy to understand and fun to talk about.

So we are talking about that shit we, you know, don't talk about or sometimes don't like to talk about, but we had to have an episode on taxes.

Maggie: Well, it's becoming the year end and we wanna make sure all of our listeners are getting as rich as they can, so maximizing those retirement accounts, saving money on taxes, making long-term plans. I mean, if we're gonna be wealthy, we gotta do some of the check boxes and we wanna make sure everybody else is prepared too.

We don't wanna, just keep the information to ourselves.

Barb: That's right. So taxes are something we have to [00:01:00] pay, we have to understand about it. We have to put on our thinking caps. It's really not that difficult. And there's some great tips in this podcast that show us what we can do now before the end of the year too, really save ourself on taxes. So it's filled with, I think, great little things we can do here and there around, tax.

Maggie: Now, I do think taxes are difficult if you file them on your own as a business owner.

Barb: Well, I would never do that.

Maggie: no, no, no,

Barb: That's why we hire the experts.

Maggie: And having some tips. Yeah. Having some experts, having some tips. Now I know what I need to do, and then I can continue just passing it off to the lady who's gonna do my taxes.

Barb: That's right. But there are some things we as individuals can do on our own behalf to help ourselves. And then once we do that, then you take all the paperwork and hand it to the expert who can put all the numbers together and voila, like a tax ferry. Then she sends 'em back to you, and then you either pay or you get money back depending on what the calculations show and you're done.

Maggie: [00:02:00] Voila.

Barb: Let's do it.

Gloria Steinem once said, we will never solve the feminization of power until we solve the masculinity of wealth. Barbara Provost and Maggie Nielsen are the team at purse strings that will help you navigate the ins and outs of financial independence so that you can be financially fearless. This is women in money, the shit we don't talk about.

Maggie: Carolyn, we are thrilled to have you on the show today. And so before we dive in, can you introduce yourself to the listeners a little bit about who you are and what you do.

Carolyn: Yeah. Well, thank you so much for having me. So Carolyn Rowland, I am based out of brookfield, Wisconsin, which is right outside the Milwaukee area. I am a certified financial planner and an enrolled agent. So I basically marry financial planning, and tax planning, and tax preparation strategies. I [00:03:00] am now a partner in Resilient Wealth planning.

I am technically the founding partner of Resilient Wealth Planning, but my business partner Kim, and her husband, who's also a partner, they live out in California and we merged earlier this year. So we are a wealth management firm, right? So we're offering financial planning, investment management, and tax preparation services.

But my sweet spot has always been retirement planning and tax planning. I got my start in the industry 2013, 2014. I actually started working in my dad's firm, helping him with taxes. So he was a financial advisor, tax repair needed the help. So he trained me on taxes. And I joke that I like grew up in this industry, but I love taxes.

I love tax law. I love how taxes relate to financial planning and your financial strategy and they are so connected. So that's really where I am today. And I primarily serve women. Women in corporate roles, [00:04:00] female business owners. Yeah. 'cause there's tax strategy on both sides.

There's financial planning on both sides. So that's me. Oh, I'm married. I have two young girls I like to think that I'm raising two fiercely independent women for our future, right. And yeah, I think so. My 3-year-old is definitely showing it. 

Barb: Already.

Carolyn: Yeah. So that's me.

Maggie: I've never heard anyone say that they love taxes. And I'm sure all our listeners, like, I'm trying to channel our listeners and be like, listen to this podcast, because yes, it's about taxes, but it's still gonna be exciting. We're still gonna have fun. And yeah, there's all this strategy that goes with it, which I always feel like

always as just like a normal person, not like a business owner. You just file your taxes and you're like, this is the bad tax day, but Carolyn loves taxes. We're gonna make this fun, apparently, their strategy, and we're gonna get into that.

Carolyn: There is. And that's why I love it. That is why I love it. 'cause there is strategy to it and it doesn't have to be a [00:05:00] daunting thing. But we'll get into it.

Barb: Well, I love that you love it.

Maggie: Yeah, and we're gonna start with your story of what kind of drew you to helping women take control of their finances. I know you kind of worked with your dad and got a good taste of the financial life, but what drew you to then working with women?

Carolyn: Yeah. I'm kinda like taking a step back, I really liked this field because I saw the relationship aspect of what my dad was doing. And I was like, Ooh, I love that. And then kind of as I started to gain more experience, figure out who my kind of ideal client was. Like I really love the emotional and behavioral aspect of women and I think we kind of like

naturally attract our own self, I guess, in the type of clients that we wanna serve. So like, I'm a small business owner, so I naturally wanted to work with small business owners, but there's just something about that relationship, like helping women. I really love empowering women to take control of their finances.

So really just like marrying that empowerment with the emotional and behavioral aspect of money. It just kind [00:06:00] of become like a natural progression.

Barb: Wow. That's wonderful. So for the most part, women in business, do you also do couples, single women.

Carolyn: A lot of single women. Yeah. I mean, I'm not gonna sit here and be like, no, if you're married don't come, don't go work with me. Like I have, I work with a handful of like single like, divorced, widowed women. Just 'cause I find that women love like they know when to outsource and like when to ask for help.

And I think we love having like partners in all aspects of our life. And so, yeah, handful of single, divorced, widowed women. A lot of like my accumulation clients. I've got a handful of single working women. Yeah, it's a broad range.

Barb: Yeah. Good. And do you do taxes individually, or do you only do taxes for those people that you do financial planning for?

Carolyn: Oh, that's a really great question and a question I get a lot too, because people are always looking to like refer out tax prep, but I try and focus primarily on tax preparation services for our financial planning or investment management clients. I [00:07:00] will take on the occasional, like 'tax only' I call it.

Like if they don't utilize our only services, if I feel like they're a good long-term fit because especially with like business tax returns or business clients, like there is a lot of. Ongoing planning that we do throughout the year and like that's what I really wanna help people do is like, again, have that relationship and with planning and all that, like we're not a transactional firm when it comes to taxes.

So that's why we really like to primarily offer it for our existing like advisory clients.

Barb: Got it. Cool. And

So let's dig into it. What's the difference between pretax or Roth retirement and how do you know which is the right move for you?

Carolyn: That is the golden question. How do you know if it's right for you, right? It really depends, but really great question because it's a common one and it's, it can be complex. Taxes are complex. I think retirement planning is complex, but pre-tax means you're making a [00:08:00] contribution into a type of account and get a reduction in your income today, So you're getting that deduction from income. Now, but down the line, when you take that money out of your retirement account, you're gonna pay income tax on it. So all that money is gonna grow, grow, grow, but every dollar you pull out is gonna be subject to income tax. Now, on the flip side, a Roth contribution is you're essentially paying the tax liability upfront.

So now, but then all those contributions and the growth are tax free down the line, assuming you're making like checking all the boxes and making the right kind of distribution, right? Like no early distribution, things like that. So it's just a difference in when you pay taxes now versus later.

And you said like, okay, how do you know if it's the right move for you? And it really depends. It depends on what your current income is, your current tax situation, like what are your future goals, right? So I think when a lot of people think about taxes, they think about. Oh, I need to save money on taxes now.

But we really wanna make sure that's aligning with your long-term financial goals. Because there might be someone [00:09:00] who loath paying taxes in retirement. And I've seen it enough too, where my clients will hit that required minimum distribution age and they have to pay, a lot in taxes and they don't necessarily need the money.

Like everybody's situation's different. But if you can control that narrative now, that's where like a Roth IRA is great. Specific examples are like, okay, it makes sense to contribute to a Roth if you're maybe just starting out in your earning years, you're in a lower tax bracket 'cause you're gonna pay, you know, the income tax on your income at like say 10 or 12%. And then maybe down the line when you need to take those funds out, you're in the 22% tax bracket, right? So from a number standpoint like that is where it makes sense. But at the end of the day, I really do like a blend of both.

I think there's something to be said about having diversification among like the type of accounts you have. So that's not just pre-tax. You think a lot of people will just kind of automatically do through their employer's 401k, but again, having that Roth bucket, maybe even a taxable bucket. So long-winded answer for you.

Maggie: Learning about [00:10:00] like taxes and thinking about how you have to think about it over like many years was one of the wildest things I've learned, like doing all of purse strings is 'cause I never thought about like, well 'what about my taxes in 30 years? Like I don't think most people think about that', and so it's always just like, how do I pay the least amount today?

Which I get that we're all trying to do that, but I've never realized that you really have to zoom out and look at it as like, you know, a 30 to 50 year picture of like when you're in retirement or all these other moving pieces that you have going on, which I don't know, I was still just like, wait, you have to really zoom out.

This is not just like a year to year, like pay a percentage. It was, yeah, it was a real learning curve for me.

Carolyn: Oh yeah. And then when you're in your twenties or your thirties, you don't wanna think about like your 60-year-old self, right? Like nobody's thinking 30 years ahead. However, it's like the decision you make today, it's going to impact future you. So yeah, your future self will thank you. I promise.

That's what I tell myself.

Maggie: so [00:11:00] are there like a common mistakes you see women make with retirement accounts that we could fix before year end?

Carolyn: Yeah. And they don't have to be big. Like it can be simple things like if you are employed, your employer offers an employer sponsored plan, like making sure that if there's a match, you're contributing enough to qualify for that, right? 'cause that is free money. We don't like leaving free money on the table.

And then it's also contributing consistently. I think where I've seen a lot of success is those that are contributing consistently, like per paycheck, you know, monthly. That automatic investing, it doesn't have to be a lot, but it really compounds over time and that's something that you can easily fix now before year end.

And then another thing too, like, you know, speaking to my business owners is making sure that if you are self-employed you wanna make sure that you are also eligible to have a retirement plan in place. So some types of retirement plans need to be put in place before year end. So just kind of having that awareness and maybe it's a set IRA or a solo 401k, like those [00:12:00] have to be established before December 31st.

But you have until your tax deadline to fund them. So again, it's kind of like being mindful, being planful. And then my last little one too is like, okay. In the last quarter of the year, a lot of people tend to get bonuses, so making sure that with that bonus, maybe throw a little bit more into retirement, or maybe you need to set aside a little bit for taxes.

Barb: Okay. So year end tax planning sounds scary. Everyone hates it.

I know. You're like drooling. You can't wait. Right? So what quick wins can women tackle before the end of the year?

Carolyn: This is great because. And when we're talking about tax planning, things that can really positively impact you, especially with this year, whether you love it or hate it, the one big beautiful bill act is gonna impact our taxes for 2025. So like everybody can benefit from making charitable [00:13:00] contributions, you wanna make sure that.

That's completed before December 31st, right? We wanna make sure we're doing that in this tax year. I really wanna make sure that if anybody has an FSA, that like you're using those tax dollars because if you don't use it, you lose it. But then on the flip side too, like you still have time to max out these contributions, whether it's to your HSA, your traditional IRA Roth IRA.

And we kind of have a little bit of leeway. You know, we say year end, but really it's kinda like, okay, tax year we tend to have some buffer where it's like, okay, we have until April 15th, but I really like to make sure that we're being mindful of planning and like doing it now versus like April 15th, right?

Because the time to plan and be proactive is now. So a couple other things I like to make sure people are doing also is reviewing their withholdings. So if you've traditionally owed, like, let's look at your pay stub, let's do kind of a projection and do you need to make any changes or did you get married this year because that's gonna impact your taxes heading into 2026.

So now is a really great [00:14:00] time to review all of that and kind of make some tweaks before your end and then heading into the new year. And then one of my kind of like personal favorite things to do from like marrying the financial planning and the taxes is 'tax loss harvesting'. So if you have non-retirement investment accounts, you may have the opportunity to harvest some losses in your portfolio, which will kind of offset your income up to about $3,000.

But then also kind of helps you with if okay, if you have some capital gains, it'll offset that income as well. So some little more like nitty gritty, granular strategies there, but I think those are good. Like, okay. At least a few of those should resonate with your listeners.

Maggie: So let's dive into a couple of those 'cause I think some of that is like foreign language. So like tax loss harvesting. Like does a layman person do that? Do you need like a professional help you with that? How all the details.

Carolyn: Okay, so professional can do it, should be doing it like that. To me, that's one of those things where. If you're hiring a professional [00:15:00] to manage your investments, to do your financial planning, like that's kind of just a yearend tax planning strategy that we would normally do, right? So that's something that for my clients, I'm looking for, right?

Like, you don't have to ask me that question. Like, everything I do is through the lens of like tax planning, tax efficiency. So that's something that's like on my year end checklist for working with clients. If you're managing your own investments, that's something that somebody can do on their own.

No problem. It's okay. Go into your brokerage account, and by brokerage I mean like non-retirement investment account. Are there any losses? So what that means is your basis is higher than the value of your stock. So there's technically a loss in the portfolio. You can sell that.

Reinvest it. You gotta be careful, like wash sale rules. I'm trying not to give financial advice here, tread lightly. But you can kind of use those losses to benefit you from a tax standpoint, right? Like offset your income, offset gains if you wanna kind of diversify out of a highly concentrated position.

Maggie: Okay.

Is there a certain [00:16:00] amount people should be like, is there like, oh, up to $600 You get like a benefit or I know there's usually like a price point or is, 'cause I know then when you do like itemized, does this go with the itemized at all or, 'cause some of us just do like the whole big write off, like whatever they give you the base.

I don't know any of the lingo. I don't know.

Carolyn: You're doing a really great job.

Maggie: I send it to my girl and I'm like, 'yo, can you', and she just sends me back what I owe or get money back.

Carolyn: So traditionally to take a deduction, and I'm talking about the federal level, right? Like states, they're all different. Traditionally, to be able to take a deduction from your charitable contributions, you have to qualify to itemize. Now, the standard deduction is so high that a lot of people don't itemize anymore.

But with this one big, beautiful bill, if you take the standard deduction, there's what's called a ' above the line deduction', so you don't have to itemize in order to get this charitable contribution deduction. So let's say it's like $600 is the number that's at the top of my mind right now.

We actually saw this during COVID, like they [00:17:00] allowed that above the line deduction, I think of $600. Yeah, so couple hundred. But I know what you're talking about, Maggie. You're like, it's usually $500. Kind of like a freebie that like, okay, you don't necessarily have to substantiate it, but don't go above that or you do have to substantiate it to the IRS.

Maggie: And then the FSA, which is the flexible spending account. So that's for like your doctors and your medical bills, correct? 

Carolyn: Yeah. Copays. 

Maggie: Let's say like you're not going to the doctor, I think you can go on like Amazon and buy things from that account, right. So it's like, buy some shampoo, buy some of your Tylenol. 

Carolyn: Buy tampons. That's like, I'm like buying women's healthcare, target and Amazon. I'm noticing like you go and make a purchase and it shows you like, oh, this is FSA HSA eligible. I'm like, absolutely. Yeah, go stock up on Band-Aids, like you said, Tylenol. Go to Costco.

Maggie: Everyone's getting personal care items in their stocking 'cause that's where all the money is

in my account.

Barb: Bandaids for everybody.

Carolyn: I love it.

Maggie: Yo, everyone needs to refill their ca, you know, [00:18:00] living on my own. I always go to like my medicine cabinet and I'm always like, oh yeah, I got that. And I open it and like it's not there. And oh yeah, I have that. I open it. I'm like, there's no Benadryl. I was like, oh yeah, I gotta restock.

Barb: Because your mom's not filling it up anymore.

Maggie: Yeah, exactly. So, maybe that's my time to fill it up. 

Carolyn: I do love the idea of that being a stalking stuffer. 

Maggie: It's what a girl needs

Carolyn: You're clever.

Maggie: Okay, so we have the charitable planning, we have the flexible savings account, we've got the tax loss harvesting. And I know you mentioned one more, I didn't write it down.

Carolyn: Reviewing withholdings.

Maggie: Reviewing withholdings. And that's important too. And so Carolyn, you had a baby this year.

Carolyn: I did.

Maggie: And so do you add like another person on your like withholdings?

Carolyn: Yeah. So I'm self-employed so like my situation's just like wildly different. But it's something that you can definitely take in consideration. So I would say like the majority of people whether if you're employed, you get a W2, like that is something that you can account for on your withholdings.

So claiming an additional dependent, 'cause you [00:19:00] should be able to bill for the child tax credit I say should like lightly, right? There's income thresholds. I mean, personally for me, like that is something that I took into account. Like my tax liability should be at least $2,000 less this year because I had a baby.

And then my medical bills should hopefully be deductible, right. So you bet i've been thinking about that.

Barb: I bet.

Maggie: We're getting this baby out and saving some money.

Carolyn: My new tax deduction. 

Maggie: And so, how can you align your tax strategy with your retirement goals to make a real difference for women's long-term confidence?

Carolyn: Yeah, I've been somewhat alluding to it already, right. Where we can see that tax planning, tax strategy really ties into retirement planning. But I think the biggest thing is making sure that taxes don't necessarily erode your retirement savings.

Like we're talking about making pre-tax contributions to help save on taxes, but you know, down the line when you have to pay the income tax on those distributions, like we don't wanna lose gains and your [00:20:00] income towards taxes. So it's kind of like, okay, that's where that 30 year planning or looking ahead, comes into play where it's like, how can I be as tax efficient as possible?

You know, that's not just like where you're putting your money, but also like the types of investments that you have. So it's really that, it's making sure that the tax strategy and the financial planning align so that we can maximize your wealth. And like to me, I think maximizing wealth is probably one of the most empowering things.

That's what drives me. And I think it's just really cool to see that number grow and to get that much closer to financial freedom.

Barb: For sure. Yeah. And on that, if listeners could do just like one or two things before year end to boost their retirement, what would you tell them to prioritize?

Carolyn: Okay. It's gotta be the ongoing contributions because that is the biggest impact that over the long run, like if financial independence is what you wanna achieve. Like just start somewhere. So I would say like, go to your retirement [00:21:00] savings after this podcast, whether it's your 401k, increase it by 1%, or if you're contributing to a traditional IRA or a Roth IRA, set up that monthly contribution, even if it's just $25, $50,

you know, if you wanna get to the maximum each year, it's I think somewhere like 500 a month you'd have to stash aside. So whatever that is, right. Just kind of set it up, automate it, let it ride. And then we talked about it before too, like are you contributing enough to get that match?

And then being mindful, like retirement contribution deadlines. So there's a lot we could do, but I think just setting yourself up for success. So those ongoing contributions and then deadlines.

Maggie: So it's your Roth that you could put, I know it's changing every year, but like 7,500 in a year, right.

Carolyn: Yeah, and it's your Roth and your traditional, so it's kinda like either or you pick one. So that's the IRA contribution limit across the board. And then you could put 7,500 in it as an [00:22:00] individual to either or, right. Traditional or Roth. And then there's the catch-up contribution of a thousand for ages, like 50 up.

Maggie: 7,500 for me and then what my company matches is just an addition or is it both of us together? 

Carolyn: So the traditional IRA in Roth IRA contribution is separate from like your 401k contribution limits. So 401k contribution limits are, oh, your. I don't know off the top of my head.

Maggie: Aren't they like much higher though?

Carolyn: They're a lot higher, like at least double like 20,000, 20,500, and then their catch-up contribution's a lot higher.

So this is where like, especially for my small business owners who. know, Maybe make a significant amount, but a traditional IRA, the limit's just too low. Like that's where we wanna start exploring a sep IRA or a solo 401k, just so we can get those higher contribution limits. 'Cause it is significant when you can get into solo 401k. Yeah, that's a good question, Maggie.

Maggie: Yeah, there's just a lot of moving parts. I mean, there's so many like [00:23:00] different accounts and like different limits and they change every year and so it's always like you've really gotta get it straight. You're doing pre-tax, post-tax. I mean, I could use a little table, a little chart. 

Barb: There's a lot of charts out there.

Maggie: I'm sure I could just Google it. 

Barb: I always like to be organized and make sure I have all my tax documents ready to go, for my tax person. I guess for the most part to be organized, you just have to know what accounts you have so you know what to expect. That's coming to you in the mail or email in terms of the different documents that you need to use to prepare for your taxes or send in with your taxes or something like that, right?

There's really nothing else you can do beforehand except know what to expect and make sure you have a list of the accounts that you have and know what should be forthcoming, right.

Carolyn: Absolutely. And I love that you start that early, I appreciate that. So using previous year's tax return is always helpful. Like look and see like, what did you have last year? That's kind of a [00:24:00] good starting point. We personally provide like tax organizers for our clients.

So it's probing questions like, okay, what were your sources of income? If you have a W2, go find it. If you have bank interest, you know, look for a 1099-INT go, go grab that investments. Like, look for that. So yeah, the sooner you can start, the better it is. I mean you, it's funny 'cause like it technically starts like e-filing starts at end of January typically, and we go until April 15th.

And, everyone's different whether you're like, 'Hey, let's just get it done right away and be done with it'. Or it's like, let's wait until that deadline

Barb: I'm like waiting at the door for my tax documents from the mail so I can get it in.

Maggie: And is it still kind of like the rule of thumb to hold on to all that information for like seven years?

Carolyn: Yeah, so technically the IRS can come after you like without a statute of limitations if you have a fraudulent tax return. But chances, like if you're doing things right, I like to say like seven years is good. Rule of thumb. Yeah. You don't need to hold onto a tax return for [00:25:00] 25 years. I give you permission to throw it away.

 

Maggie: I know some of our listeners need to hear that, where I'm just like, I don't even know if I could find mine from four years ago, so God bless.

Carolyn: Yeah, I think I have a digital copy somewhere.

Maggie: We'd cross that bridge when we get there.

Barb: I know exactly where mine are.

Maggie: Of course you do.

Carolyn: Oh, I love it. Of course. You do.

Maggie: No, but this has been good. I think it's a lot of good tips to kind of end up the year to max out those retirement savings and to help 'em be financially fearless.

And so, Carolyn, since you're on the podcast, you get the question everybody gets, what is your definition of financial freedom?

Carolyn: Financial freedom to me and financial fearlessness is that freedom to have choices and to make decisions with confidence, with control, with empowerment, right. And. Like that to me is financial freedom. And also aligning that with like your core values so you can live the life that is the most [00:26:00] meaningful to you.

Like, it's not about a specific number of wealth. It's more about the meaning of like, not the meaning of life, but the life that is the most meaningful to you, right. And that's different for everybody.

Maggie: I love it.

Carolyn: Yeah.

Maggie: Well, thank you for coming on and sharing your expertise. For those who don't know, Carolyn's also one of our purse strings approved professionals. So we're so excited to have her in our network and I encourage you to reach out to her if you need any help. Financial planning or tax planning or both 'cause clearly she knows what she's doing.

Carolyn: I'm honored. Thank you. I appreciate you having me.

Maggie: Of course. And so until then, get tax planning and be financially fearless. 

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