This week, we’re diving into a topic every self-employed creative needs to understand—but that most of us avoid: taxes. And trust me, this conversation is anything but dry.
I’m joined by Hannah Cole, tax expert, longtime working artist, founder of Sunlight Tax, and author of the brand-new book Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed. Hannah has helped tens of thousands of creatives build confidence around money through her clear, compassionate, jargon-free approach. She believes that financial clarity is a foundation for better, more meaningful creative work.
Whether you’re early in your business or leveling up, this conversation will leave you feeling empowered, informed, and equipped to make smarter financial decisions—so you can focus on your best creative work.
Grab Hannah’s book Taxes for Humans, and get ready to rethink what’s possible with your money and your creativity.
Show notes:
Learn more about Hannah:
Book recommendation:
- Long Walk to Freedom, by Nelson Mandela
Follow me on:
- Instagram @stacyennis
- Facebook @stacyenniscreative
- YouTube @stacyennisauthor
To submit a question, email hello@stacyennis.com or visit stacyennis.com/contact and fill out the form on the page.
Becoming uncomparable: Why your niche is your superpower | Episode 229
These transcripts were generated by robots, not writers.
Hannah: I would say that most of the work that I do is honestly like therapy. I’m not a licensed therapist, but you know, most of it is kind of around that. Like you’re valid, your work is valid. Your work is more than valid. It’s important and just upholding that and like undoing that mental load of feeling like, yes, exactly what you said. Like to be creative, to be making work that is truly good, truly authentic, truly speaks to people’s soul.
Hannah: Requires poverty and suffering. No, it actually really does not. In fact, you do better work when you are coming from a place of security. Truly, you’re. You’re just able to focus on other people in a way that you can’t when you don’t have your basic needs met. So there’s nothing corrupting about that.
Stacy: Welcome. Welcome. This week I am really excited to talk about a topic that hasn’t really been covered in much detail here on the podcast and it is the perfect topic to bring to your family Thanksgiving table. And that is taxes. You know, like easy thing to bring, no disagreement. Certainly can bring in the politics angle too. But all jokes aside, this week’s expert is such a perfect fit for this podcast because she focuses her tax expertise on helping creatives. So let me introduce you to this week’s guest.
Stacy: Hannah Cole is a tax expert who specializes in working with self employed people, especially creative and mission driven ones. A longtime working artist herself, she’s helped tens of thousands of self employed people skill up with accessible tax and money education through her Money Boot Camp program, tax workshops from Florida to Alaska, and the Sunlight Tax Podcast, her forthcoming book, which is published today. As you are listening to this episode, Taxes for Humans, Simplify your taxes and change the world when you’re self employed is the most funny and empowering tax guide you’ll ever read. Hannah is the founder of Sunlight Tax. Welcome Hannah. I’m so glad to have you here.
Hannah: Thank you so much, Stacy. I’m so thrilled to be here.
Stacy: I love your niche, focusing on working with creatives and for me, dealing with the financial side of the business took me a long time to kind of get comfortable with it. And I spent a long part of my career saying I wasn’t a numbers person. That was just kind of my cop out to, you know, understanding the numbers, paying attention to them. And eventually I learned through experts that have supported me to get to know my numbers, to appreciate them, to nurture them. But truly that took me like 10 years. It was a long journey. I would love to hear about your journey as a creative. You are a working artist and how that led you into specializing for taxes in taxes for people like me, for self employed, mission driven creative people. Yeah.
Hannah: So it’s completely organic. I am one. So when I, you know, I kind of grew up just feeling like a weirdo. And I always knew I wanted to be an artist. And even though the world gave me a lot of messages not to that, you know, it’s not a safe path, et cetera, but just being around other artists was always where I felt comfortable and it just, it felt like a place to be authentic, be yourself. I would say being an author is very similar to that. And, and so I definitely grew up in this sort of anti capitalist mode and just was like, okay, I’m going to go into weirdo zone, you know. And so I’ve been a professional artist for over 20 years. I’m still a professional artist. I never stopped.
Hannah: But what I found is that when I tried to, you know, as a professional artist, tried to approach a accountant, you know, tried to get my taxes done, you know, my, I went to my dad’s accountant, the only one I knew, and he, I sat down in his office and he was like, so when are you going to get a real job? And I’m like an artist professional. I have work in museums, I’m getting residencies, I am applying for grants. Like, I, I’m an actual professional. And this guy didn’t even know the difference between a hobbyist and a professional. He certainly was not respectful. And I was so flooded with shame sitting in that office that like any question I had about what are quarterly taxes or like, what’s an IRA and should I try to do that.
Hannah: Like, that all went out of my head immediately. And I was like, oh, I don’t feel safe right here. I’m gonna have to prove that I’m a legitimate human being in this space. So I just. The reason that. The reason that I got interested in money and taxes was basically anger. I was so mad at how I got treated. And I made enough mistakes, painful, terrible, humiliating mistakes, that I just was like, this is so hard. This is way harder than it needs to be. And I just think people like me, like, my community is the creative community, and people like us need to do our taxes too, and we don’t need to get insulted while we do it. So I just wanted to create. You know, I went all the way back to school and I studied accounting.
Hannah: I even, like, I had a real chip on my shoulder and something to prove. I was like, I’m going to have to get a 4.0 in this because, you know, there are people like my dad’s accountant who won’t believe me unless I can point to something like, my grades were perfect and so, you know, psychological. That’s true. And I did that. I’m a real box checker. But yeah, I just was like, you know, we need this stuff. Like, creative people like me need this stuff. And I. I’m not an artist because I think it’s invaluable, you know, a not valuable thing in the world. I. I’m the opposite. I feel like people who are writing very vulnerable book people who are putting their heart out there in the world. That’s the work that our world needs. You know, we.
Hannah: We need more empathy, we need more connection, we need more community building. And that is what people like us do. That is what creative people do. I think the humanities get really have had a bad name in the last two decades, and I am here on team humanity to say, like, we need this stuff. We are important and we need to have good financial information too.
Stacy: Oh, so much of that resonates with me. And I’m going to follow up. But before I do, for anybody who’s watching on YouTube, you have like an ethereal sunlight coming across your screen right now, which, like, looks like a special effect and it’s so beautifully perfect. Sunlight tax. Here we have it. You had me thinking about a couple of connections for me. So as a writer, I always had this narrative drilled into me that to be a true artist in writing, you had to be broke and you would have to suffer. And I even. I’ve told this story on the podcast but one of my. I did graduate school in professional writing and there was also a creative writing program. In truth, I wanted to do the creative writing program. That’s what I would have preferred.
Stacy: But I knew that I wanted to build a business. So I did the professional writing because that felt like a more practical path. And I’m very grateful that I did that. But I had one of the graduate students who like really belittled me one time over drinks at a bar just like in front of a bunch of people because I was making money for my work and he just thought I was a sellout and not a true creative person. And, and that, you know, that we often feel like we have to choose between having a financially successful life and having a creatively successful and fulfilling life. And there was some point, it was before that moment with that guy that I, I think I was in my bachelor’s degree that I was like, no, I don’t feel that’s true.
Stacy: And, and I also studied visual art. I don’t know if you know that Hannah, but I have a minor in visual art and I just kind of made this decision that I was going to be successful in my work and I was going to do something that made me fulfilled and it was also going to be creative. And so I love that is your posture for creative people. The other connection I want to make is I have this really specific memory of going to my parents accountant as well now. I actually really like have a tender spot in my heart for me since passed away.
Stacy: But when my first, when I was pregnant with my first child, I didn’t understand anything about like taxes and I didn’t understand how as a business owner if I like went in and I was like, can I you know, give myself maternity leave and have some sort of tax credit? I didn’t know, you know, I just was. And he laughed at me and he was like, oh, why would they allow you to do that? And you know, it was one of those moments where you’re ignorance. I was ignorant in the moment. But that also felt like reasonable for a self employed person to be able to take maternity leave. So all these messages that we’re getting and I’m curious to hear from you with your clients and the work that you’re doing.
Stacy: How much of your work is actually undoing these scripts, like tearing apart these narratives and helping rebuild more empowering narratives.
Hannah: Yeah, such great question. I feel so much for the Stacy who experienced both of those like painful comments in art school when we had like a Summer studio sale. I remember I sold a big painting and it was such a coup because it meant I would get to be in the studio working for the whole summer because it was enough money to support me and as opposed to having to get a job for the summer.
Stacy: Right.
Hannah: So it was like the difference between staying an artist and not being an artist. And this guy called me a capitalist pig dog for making a sale at. At a sales event. And I just. It was very similar to that. And I was like, wait, I thought that’s what were doing. Like, what? Anyway, yes. So many feelings. And also that same sense of, like, being in the wrong space with an accountant. Like, asking a question that feels like a legitimate question and being kind of shamed for it or being like, oh, you’re so dumb. Yeah, I just. I would say that most of the work that I do is honestly, like, therapy. I’m not a licensed therapist, but, you know, most of it is kind of around that, like, you’re. You’re valid. Your work is valid. Your work is more than valid.
Hannah: It’s important and just upholding that and, like, undoing that mental load of feeling like, yes, exactly what you said. Like, to be creative, to be. To be making work that is truly good, truly authentic, truly speaks to people’s soul, requires poverty and suffering. No, it actually really does not. In fact, you do better work when you are coming from a place of security. Truly, you’re. You’re just able to focus on other people in a way that you can’t when you don’t have your basic needs met. So there’s nothing corrupting about that. I mean, people think about. Think about how specific that is to creative fields and how we shame each other for money. Like, it doesn’t have to be that way. Great doctors are actually paid better. Right.
Hannah: Because in that field, they recognize that’s somebody who has, like, done a lot of training, has a huge level of expertise and is good at what they do. And in fact, when they get better at what they do, we pay them more.
Stacy: Absolutely. And there’s certain specialties that are valued for that expertise and knowledge, and there’s an expectation to be compensated. And I do think there’s also this element in the artistic community around if I focus on the money side of things and I’m not being true to my craft. Whereas to your point, actually creating an abundant, A financially abundant, stable, nourishing life gives you so much more mental space and creative range so that you’re not worrying about money. You can actually focus on the Thing that you’re creating.
Hannah: Absolutely, absolutely. Like, I have thought about. I think I crossed this. Like, I crossed a couple mental barriers myself in my art. Like, for example, I make paintings that are very tightly realistic. And one of the things that I have always felt, both in art and in writing, is that clarity is smart. And I think there is this, like, writers can. Can be this way. Like, you probably have feelings about this. But, like, there are some writers who to. To my mind, are insecure, right? Who want to throw a lot of big words and make things feel very complicated. I remember reading a lot of essays at Yale where I went to school that were by authors that were so such a difficult thing to untangle, what the actual idea was. And I was like, this doesn’t do me any favors, right?
Hannah: This is this inaccessibility. I think this author thinks this makes them seem smart, but I actually think it’s a sign of intelligence to make things clear. It’s actually harder work. It’s doing the hard work. I believe in doing the hard work. And I think realizing that little false equivalent kind of revealed, like, oh, there are some false beliefs hanging out around here. And another one here is this, like, you’ve got to suffer. You’ve got to be poor. I actually think, like, a lot of what I teach is about how to automate things and how to make them simpler, not how to, like, be in a spreadsheet all day. Because the point is not that you become an accountant and give up the creative work that you’re there for.
Hannah: The point is to get in and out as fast as you can, but have it working, like, functional so that you can get back to your work. It’s so that it takes the mental load of that fear off of you. Because when you have that fear about your money and not having enough and not knowing what the next tax payment is going to look like when that fear is gone, you can write better. Like, you just have mental energy. You’re not fighting a fear monster. At the same time, you do such.
Stacy: A good job in all of your content, of breaking things down into very simple chunks for people so that they can digest it. It’s also in everyday speak, you know, you’re really good at not using jargon of making things very accessible, of also making people feel seen and heard. And I know your new book, Taxes for Humans, which I love that title, it’s such a great title, is really about making this, what feels like a really inaccessible, confusing, overwhelming topic, fun and clear for readers. So can you tell us a little bit about your book, what inspired it and what you’re excited about as it launches. I mean, we’re recording this a little bit in advance, but it’s today. This is what you played on your book launch day. So tell me about your book and what people can expect from it.
Hannah: Yeah. Thank you. I’m so excited about it. This is the book that I wanted to have when I was 25. Stacy:
Me too. I feel like I would have. I needed this book a long time ago.
Hannah: And I really. So I know there are, you know, there are ways to write a book within an ecosystem of other paid products and all this like that is a thing that exists in the world. When I read a book that’s too much that way, it frustrates me and I feel like, well, why don’t I buy this book if it’s really just trying to sell me on a bigger problem program? I did not do that with this book. This book gives everything away. This book is everything that I do. It’s all the secrets. And I just want to make clear how much gatekeeping there is in accounting. It is a field that thrives on your confusion because if you’re confused, you get to pay me. Right? So it’s the opposite of that. It’s absolutely clear. It makes things clear.
Hannah: It actually disputes dispels a lot of myths that I think feel like a relief to the beta readers who’ve tested it. And I just feel so proud of it. This is a book that I feel like it is the book that I wanted to be in the world. Even if that sacrifice is maybe a little income for me.
Stacy: Right.
Hannah: Because I just think people need this book. My feeling is this book is so good that you’re going to want to tell your friends about it because it just tells you how to set up really simple systems. Like so simple you can’t believe it. Like I have a receipt system that is five minutes and then you’re done forever. Five minutes of your life and all your receipts are taken care of. So just things like that, plus like setting up, you know, some of the stuff that people want in their, you know, in theory, but don’t take time to do it teaches you about, like, well, why money is important. Reinforces that feeling of like, you’re going to do better work if you have some savings. And like, here’s some tax advantaged, you know, like ways to make your money your limited dollars.
Hannah: Go further with tax advantage accounts. So it teaches you that stuff you don’t get when you pay a Tax preparer to do your tax return. It’s like, here’s the systems, here’s why it’s this way.
Hannah: It’s a lot of the intelligence behind it, but just made really simple. So I’m excited.
Stacy: I’m excited too. I know that simplicity piece is so important because a lot of this can overwhelming and difficult, especially when you’re not a numbers person. Like I was and it. You actually gave me another little flashback early in my business, I would do what I think a lot of people do and I would just save all my receipts in like boxes all year. And so then like tax time would come and I would like scramble to find somebody to hire for a couple days. And I had this one year where I was in. I had rented an office in this like big office building where you could rent a conference room when you needed it. You know, it had like shared spaces and stuff.
Stacy: And I had hired some teenager to come help me like separate all the receipts and like enter it into a spreadsheet. And it took two days. And I was like, this is never going to happen again. You know, it’s those things. Thankfully, I’ve. I’ve now sent up, set up, expensify and I use that for all of my, receipt capture. But, you know, those are the things you don’t know in the beginning. You just don’t. You don’t think about it. So what are some of the things that your book offers, Hannah, that maybe you could give us some tips and tidbits from it that could help them start to make, I guess, like take steps toward feeling tax confident.
Hannah: Yeah, I love this also. I have been there. I also have been there with receipts on that. And just not just me printing out bank statements before I had a separate business bank account printing out my bank statements and going through with a highlighter. A whole year of bank statements being like, I think that trip to Home Depot was a business expense. I’m not positive. Might be illegal. Not sure.
Stacy: Same.
Hannah: So, yeah, I’m not coming from a place of superiority. I’m coming from a place of like, I have messed it all up. I have made every mistake and even worse mistakes than you have. And so come learn from me. Let my pain teach you.
Stacy: That is what the book is.
Hannah: There are a lot of vulnerable things about horrible mistakes I made. But actually I also want to mention that there is also a workbook. And the workbook is a companion to the book. The book is like the teaching, very gentle, very simple, not talking down to you, the workbook is sort of the mental, like the mindset exercises. You need to actually be able to use the book, like, to put it into practice. And the other thing that the workbook has that I think is super practical is it has a really beautiful tax organizer. It actually is about a third of the workbook itself. And so it literally asks you all the questions, like the whole, here are the things that are going to be on your tax return. Let’s get that info organized. So it. That the workbook has that.
Hannah: And I also want to say, like, one of the challenges of writing a tax book is that tax laws change every year. It is an evergreen book. It is written so that it’s got what you need every year. And it refers with QR codes to places for the updated info for each year. Wow. So, yeah, so that’s. I think that’s really useful. I. I mean, like, I mean it. I meant this to be the ultimate tax guide that just like teaches you and it’s. It, like, this is all you need. So it is definitely that. And so there are things like, you know, speaking of great Thanksgiving conversation, this massive tax law that was passed in July, the one big beautiful bill act it. There’s a ton of new tax law changes.
Hannah: And I have like, a little QR code in the book to get the update to the organizer for, like, all the little questions that shifted a little bit that you want to add on to the organizer, the new bill. Right. So you are not missing anything that’s new in the book itself. I think one of the most important this is basically from just 10 years of, you know, understanding how. Where people are getting confused. One of the things I think is most confusing to people is understanding the difference between your receipts, your tax documents, and your bookkeeping. If you realize that those are actually three separate things that have their own function and their own reasons for existing.
Hannah: When you understand what those reasons are, it actually makes it way clearer what receipts are for and what you therefore then need to do with them. And so the book clarifies things like that. So, for example, receipts are. You actually never need to look at. You need them in case you’re audited because they’re proof that shows that the expenses you claim on your tax return are real. So if the IRS pulls your tax return, which they’re allowed to do going back three years or six for some special reasons, so you should always keep receipts for seven years. But if they pull one of your tax returns from the last six years, you need to be able to pull out a file that has the receipts from that year. Right. So that’s key. That’s important. You can’t throw out your receipts.
Hannah: You do need to keep them, but you don’t need to be spending two days in a conference room sorting them through. And I’m not trying to throw light on you, Stacy. I have also, for me, it was my living room, the cat walking all over them. But we don’t actually need to be doing that, really. You just need to like, make sure that all the receipts from one year are in a file folder and you know, then the virtual version in your inbox in a file folder. That’s it. You don’t actually have touch them. So, yeah.
Stacy: Some other faux pas that you see specifically, you know, these self employed, creative, mission driven people make when it comes to maybe their finances broadly, but maybe more specifically their taxes.
Hannah: Yeah. I think one of the hardest things to understand, especially because there’s such a noisy Internet environment that tells you, oh, you need this for your business. Oh, you need this. Like the peanut gallery about your business is so strong. And then as we talked about in the beginning of this talk today, we also get that like, judgment component of like, you know, the accountants being like, you don’t know anything, and then the artist being like, you’re losing your soul, you’re a sellout.
Stacy: Yes. Hannah:
I just, I think one of the most confusing things is like, when does your business actually start? That’s a tough one. Right. And something really important to note is that different entities may have different start dates. The most important thing for people listening here to know is that for tax purposes, the IRS is first. Because the irs, if you think about it, the IRS is like, no, you were a business long before you did anything official because we want you to be paying taxes like immediately, day one. And so if you just think like, well, the IRS’s job is tax collection. They’re not like hanging out, waiting until you decide you’re ready to form an llc. Right. An LLC is optional. You don’t have to do it. Taxes are not optional. And you do have to do them. So.
Hannah:So the IRS is not waiting for the official stuff. They’re like, no, you’re already a business. So one of the important things for everybody listening to know is the IRS definition of when your business starts, which is when you have a profit motive. Right. Note that comes long before you have a profit. Right. So you actually are probably going to start your business without having a profit. You’re going to have A loss for a couple years before you become profitable. And you still get to take all these deductions during those loss years. That’s actually like a huge tax benefit because you get to essentially report negative income which takes away taxes that you would otherwise owe if you were not yet taking those deductions. So that’s really important to know because it’s actually an awesome thing. It’s like very supportive of your business.
Hannah: But people, because of fear and a lack of knowledge of that, they don’t do it. They think like, oh, I haven’t done a pro, I haven’t had a profit yet. I haven’t done the official things like, you know, maybe an llc, maybe an S Corp. Those things can come later, but get your deductions now.
Stacy: Such smart advice. And I was also thinking, Hannah, and some of the things that I did later on. One thing that I, that changed a lot for me was becoming an S Corp. Tax as an S Corp. And it’s interesting because I, I believe in taxes. I think they’re important part of our society and supporting people and funding programs. And I look back on some of my earlier tax years where I was making a lot less money and paying more taxes actually than I am today. And I, you know, I, I feel like I missed out on a lot of opportunity, just not understanding my taxes. I also had very early in my business, I think it was probably like in the first two or three years had a huge tax bill come through. One year.
Stacy: I mean, it was like today it wouldn’t be such a big deal, but at the time it was like devastating. You know, I get this massive bill in the mail. I think my, I think at least one of my kids was a baby at the time. Must have been my oldest. And you know, staring at that number and just thinking, oh my gosh, so I have to pay this year and I have to pay last year that I didn’t realize was due. There’s all of these things that I think ignoring or not educating yourself about your taxes, one can put you in a dangerous financial position because you can have these bills come due that you didn’t realize were on their way.
Stacy: And then two, you end up missing out on your own financial future because you’re not taking the steps to create a more tax advantaged situation for yourself. And I know S Corp isn’t right for everybody, but it has made a huge difference for me in my business and also becoming an employee of my business and paying taxes as I pay myself. So when I process my own paycheck. That has made a huge difference for me. And it’s one of, I don’t know if that fits under your automation categories, but for me that has changed so much. Just having that just taken out of my own paycheck and all of that kind of done through. I use gusto for or gusto. I don’t know how to say it for my payroll, but some of those things have made a big difference for me.
Stacy: I’d love to hear your thoughts on that and also any other maybe tips or strategies you have for our audience that maybe have a little bit more established business or they’re kind of in that place where they at least have like maybe somewhat settled in after those initial bumpy years and are ready to kind of explore next steps with their business.
Hannah:Yeah, I agree. And it’s funny how it kind of flips in the early days when you’re starting a business. A lot of people miss out on deductions that they could and should be getting because they don’t realize that they’re allowed to take them when they don’t have income. That just the profit motive is what makes them a business, not actual profit. So that understanding in the early days is helpful. Then later, what’s important as you start to make money is ways to save money. Like for example, an s Corp, which P.S. You should not do until you have consistent profit over roughly $65,000. Or also for those of you living in the United States, you need to check your state rules in the book. I have a list of them. But some states tax away all the benefit of an S Corp.
Hannah: So if you live in one of those states, you are wasting your money if you form an S Corp. New York, I am looking at you. So that’s really, you know, those details really matter. And also just knowing that taxes are, you know, they say death and taxes, right? Taxes are always going to be there. And so if you make more money, your tax bill is going to be higher, your tax rate will actually go up. And just under just a basic understanding of like, oh, I made more money, that means my tax bill is going to be higher like you. And, and that paying quarterly taxes is going to help keep me ahead of a scary tax bill. Like quarterly taxes feel scary when you don’t know how they work.
Hannah: But once you do, you realize, oh, this is so I don’t get slammed in on April 15 with a bill that is terrifying and going to actually derail my next year. I’ve done it too. I think it’s as soon as somebody has a really good year in business, this is often one of the terrible whammies that comes with your first great year of making money. It’s really, it’s a kick in the pants when you want to be celebrating. So.
Stacy: Yeah, and it’s not a very. Yeah. That’s one of the least fun pieces of mail to receive.
Hannah: Oh my goodness. Stacy:
Hannah, we’ve talked a little bit about your book and because we have so many published and aspiring authors that listen to this podcast, I would be remiss if I did not ask you about your writing process. I would love to hear from you about your journey of writing your book, any hurdles or challenges you faced during that process and how you overcame them to, you know, get this book out into readers hands.
Hannah: Yeah, I mean, I do have to shout out your community, Stacy, because it has been so helpful. I’m now in the, you know, book launch mode. Just talking to other authors who are sort of in a similar mindset has been really helpful. Just like, hey, what are you doing? What are you doing? In terms of the writing itself, a really strong outline, like really digging in. I felt the book proposal, of course, a book proposal is its own huge journey. But that work of really outlining the book super well was so important to me because then it made the writing much easier. I just was like, filling in the outline sounds a little too easy. It wasn’t that easy, but it was much easier. And I would just like, you know, this is like a sort of wellness tip.
Hannah: But I would just like, I have a seasonal business, you know, nobody wants to talk to me about taxes poolside in July. So my summers are pretty quiet. So I was just like in the. I would just like get some exercise and then like come sit at my desk. The first two hours of the day was just writing. When that’s my brain is it’s most powerful and refreshed and like I just do the best work. And I would find two hours in the morning after a little exercise was just like my peak brain power. And so I just tried to maximize. I would never schedule a meeting in that time. It was like I made it sacred. Like that’s the time my writing is best. I’m gonna keep it sacred.
Hannah: So that was my strategy for kind of like doing that powerful, difficult work of writing just using my best time of day.
Stacy: That’s so smart because you also have that like the exercise pumping through your body and you get to sit down and be really focused. And also that consistency of showing up daily and putting in that block, I mean, that is really everything. You’re also training your brain to be creative. Creative and get into creative flow. Did you hit any spots during the writing process where you had to, you know, like, kind of dust yourself off and. And get back into it, or do you feel like it was really smooth all the way through?
Hannah: Yes, I did. Definitely. The book. The book I thought so long and hard about, and I outlined so thoroughly, and I, like, pushed it through the book proposal process. I actually felt more on top of the book. But the publisher asked me to write a workbook, and the workbook kicked my butt.
Stacy: Why was that, really?
Hannah: Because I hadn’t been the one to propose it, so I really had not thought it all through. I had committed to it, but I had not dreamed of it every day for five years before it came out. So I found it really challenged me to think through. You know, a workbook is different. You’re not just giving information. You’re really thinking through how the reader is going to receive that information and work with it. And, like, what is a prompt that’s going to be helpful and surface the right things? And there was a moment that I almost died. This tax organizer. Like, I have a tax organizer. You know, for many years I’ve done taxes for creative people. I don’t anymore. So you can. You can save yourself sending me that email. But.
Hannah: But I. I have a tax organizer that every year I would revise and I would. I’m very careful with it. Like, I do a nice job making sure that it really coaches you through. Like, here’s why I’m gathering this. Here’s what it’s for. Here’s, you know, what. What makes a difference and what is just, like, just do this. It doesn’t matter. I had originally written the whole workbook and not included the tax organizer. And, like, through some discussion and beta readers and my agent realized it needed to have the organizer, but had a very tight word limit. And the tax organizer was about a third of the word limit. And so I finally realized I had to include it. And I.
Hannah: It also meant I had to go back through the workbook and take out a third to a half of the workbook that I’d written already. So I basically had to rewrite the workbook in order to do this. And I just had that feeling, you know, like, I’m gonna go through all of this with the publishing and the launching and all this. Like, it’s. I just. I’m gonna feel better if this is the best thing that it can be and if it really has the thing that it needs to have. Oh, but it was, like, devastating to my heart.
Stacy: I can imagine. Yeah. Going back through and. And I remember. And hopefully this is okay to share on this podcast. If not, we can always edit it out. Hannah. But when we. We chatted at the beginning of your journey and I didn’t coach you through the process, but we’ve known each other for a while, so had chatted about this. This workbook and how this would, you know, be positioned with your book. And I remember in those conversations that you really. It was really important to you that it wasn’t just fluffy, like, repetition of the main book and that it wasn’t just like, basically, here’s the book, and then here’s a book you can write in with the same content, which. That then necessitates a much different approach to creating a workbook. If you are really designing.
Stacy: It’s a complimentary entity, but it’s not, like, directly pulled from the main book and just like a journal you can write in. And then especially given the fact that, as you mentioned, your publisher is the one that requested it of you, then it’s not, like, birthed by you in that sense. So you have to adopt it and really claim it as your own and then envision what this will be. What was your process for deciding to create the workbook the way you did, instead of what would have been much easier in just making it a companion, like, companion information with space to write?
Hannah: Yeah, I just. I can’t. I’m no good at sales, and I just. The only sales I’m ever going to be able to do are because I actually think something is the best. And I just had. I just knew that this workbook had to actually be good. That was the only acceptable answer to me. And it was, you know, when. When my agent was like, you need. We need the organizer in this. And I realized she was right. And I was like, damn, I’m gonna have to rewrite this whole thing. I just. It wasn’t really a question. It was just like, it has to be. It has to be the best thing that it can be. It has to be helpful. The person who buys this cannot have the experience of like, oh, this isn’t as good as I thought, or, this is fluff.
Hannah: Like, I just was not willing to put that out there with my name on it. So I do think I. Time will tell. We’re recording before publication day, and we’ll see how well I do with my book launch. But I feel much better in the launch and in this end of the author journey now knowing, like, really believing in the work. But, yeah, I feel like I may have lost track of your question, Stacy.
Stacy: No, it’s because I think, I mean, this is also the challenge of being a creative of any kind, because it’s like you. You know, the potential of the work. And then there’s also a point where you have to stop and you have to say, okay, this is what the work is. This is the best that I. I can. I can give. And also get it out in the world. Because you could have tinkered with this forever, you know, and totally. But. But to be able to go into your launch feeling like I did my best work within the timeframe that I had to do this thing, and I feel great about it. I know it’s gonna help people, I think is an amazing way to step into a book launch.
Stacy: You’re not going to have any regrets about what you’ve put out into the world.
Hannah: Yeah, for sure. I mean, I still fear the bad reviews. They’re probably mostly gonna be political like that people feel like, oh, I don’t think about taxes the way she does. I think we should all not pay taxes. And that’s not my belief. I know those reviews will happen.
Stacy: Yeah, it’s part of it, right? There’s always the one stars every so often, but actually they make the five stars more authentic because you know that the people that are leaving reviews truly love and appreciate the work that you do. Hannah, this has been such an amazing conversation. We got into areas I wasn’t even expecting. Today, your true care for the community that you serve really shines. I’ve attended a webinar. You did? In the past. I’ve listened to your podcast. I know you personally and you are just truly authentic, smart, caring, and I know that your. Your book reflects all of that. Before we leave, I’d love to ask you the question that I ask all of our guests, which is if you could recommend one book to listeners. So this is outside of your own book, one that has profoundly impacted your life.
Stacy: What would it be?
Hannah: I am such a big reader, and choosing is the hard part. Okay. I think my. It’s a two part book, but it is the autobiography of Nelson Mandela, which I read 25 years ago because my brother did a study abroad in South Africa. That book changed my life because it really embodies the kind of empathy that I think the humanities and creative Work magnifies in the world. The thing about Nelson Mandela, I mean, that book, despite it being two, 500 page part one and part two, it reads like a thriller. I mean, it’s so incredible. But the thing that I found so profound in that book is his radical empathy. Like, we’re in a day where I hear young people say things like, I don’t owe you an explanation or I don’t. It’s not my job to teach you.
Hannah: And Nelson Mandela was the opposite. Like, he had so much empathy and care towards PW Botha. If you’re, if you don’t know the history, you know, South Africa was under apartheid, though it was majority black, it was ruled by white settlers. And Nelson Mandela did the really hard work. Went from being a freedom fighter, kind of like young punk, to being an incredibly thoughtful leader of a nation. And this incredible change. And he brought about this incredible change by having empathy with his oppressor. And I just, I cannot tell you how profound that concept is to me and how profoundly I think that message is needed today in this world we’re living in with cancel culture and a total and just a lack of empathy.
Hannah: Like his ability to see the humanity in this person who had wronged his people and to understand that embarrassing him was going to be counter to his own objective, that moving forward, making progress, getting political justice was going to actually require him understanding this person that he had every right to hate. Right. So that kind of empathy is what I think the power of creative work is capable of putting out in the world. And so that’s what I live for, that empathy. That is why I do the work that I do. That is the message I want to leave everybody here with. That is the value of the work of you, the listener who’s working on your book. Your one amazing, passionate book. That’s the thing I want to leave people with.
Stacy: That’s beautiful, Hannah. Thank you for sharing. I look forward to reading that book. I haven’t read it yet. Hannah: Don’t be intimidated by the length. It’s really good.
Stacy: I’ve never read a thousand page book. If it’s 2, 500 pages, that may be. Yeah, I’m pretty sure I haven’t.
Hannah: I didn’t have kids when I read it.
Stacy: Yes, fair enough. Well, Hannah, where can our listeners buy your book and where can they follow you and learn more about the work that you do?
Hannah: Lovely. Well, all of everything I do is on my website, sunlighttax.com you can find a visual guide to writers, tax deductions. If you want. That’s a juicy, free thing on that website. And my book is sunlighttax.com book, but it’s up in the menu, so you can just go to sunlighttax.com and find it there. Yeah. I’m so excited for this book to be in the hands of your listeners because it’s the book I’ve always wanted to exist in the world. It’s the really empathetic tax guy. That’s funny. So I’m really excited about it. I hope you enjoy.
Stacy: Congratulations. That’s a huge accomplishment. And thank you for celebrating with me on the podcast. I really appreciate you coming on and sharing your knowledge and stories. And again, congratulations on your book.
Hannah: Thank you so much. And Stacy, if I can say just a word to you, when we had that conversation about my workbook, and I just, I realized that you have a strategic brain that is really special. Like, you have written so much, you have worked with so many people. You have that, like, overview. You know, a lot of writers like myself, we can’t see. See the forest for the trees. And I really felt your, like, deep care and expertise when I This week, we’re diving into a topic every self-employed creative needs to understand—but that most of us avoid: taxes. And trust me, this conversation is anything but dry.
talked to you. And I just, like, now I’m in your community and the other authors there are so special. So I just wanted to shout out the incredible work that you do.
Stacy: Oh, thanks, Hannah. That made my day. I appreciate that. Thank you so much for joining me. Hannah:
Awesome. Thanks for having me.
Stacy: And thank you to you, our listener, for joining us today. I hope that this conversation is hitting you at exactly the right time. Whether you’re young and you get to avoid all the mistakes that Hannah and I made, or you’re farther along, further along in your journey and learn some things today that can help you be more organized and confident. Do grab a copy of Hannah’s book, Taxes for Humans. Thank you as always to Rita Domingues for her production of this podcast. She is truly the reason you’re listening right now. If it were just me, it would still be in the folder. She is. She is the. The force behind everything, and I am grateful. And since you’re still listening or watching, please take a moment to follow me on whatever platform you’re on. Stacy:
That’ll ensure that you get more of these great conversations in your feed. And if you have a second to rate and review the podcast, that also makes a huge difference in helping me reach more people with the message of the living a life that’s not just better, but beyond better. And I will be back with you before you know it.
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