The Compounding Effect of Daily Content Creation with Stephanie Halligan

My guest today has dedicated her life to making the world a better, brighter place … with the power of doodles.

She was a Financial Empowerment Consultant and the founder of The Empowered Dollar. During this time, she helped millennials and low-income families fix their finances and feel empowered to take control of their financial destiny.

Her latest and fastest growing venture is Art To Self — which she started early this year and has seen incredible growth from it. It is a website and newsletter of daily art and inspiration sent straight to your inbox — I have to say they help my mornings.

Now, Lets Hack …

Stephanie Halligan.

In this 33-minute episode Stephanie Halligan and I discuss:

  • Carving out time to do work that matters
  • Why consistency is the key to finding out how you work
  • How Stephanie managed to get her voice out there
  • Why it’s okay to not know everything before starting
  • Forcing ourselves to stay consistent in our work
  • The power and compound effect of daily content creation


The Show Notes



The Compounding Effect of Daily Content Creation with Stephanie Halligan

Jonny Nastor: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: Hey, hey, hey. Welcome to Hack the Entrepreneur. Thank you so much for joining me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest for today has dedicated her life to making the world a better, brighter place with the power of doodles. She’s a financial empowerment consultant and the founder of The Empowered Dollar. She helps millennials and low-income families fix their finances and feel empowered to take control of their financial destiny. Her latest and fastest-growing venture is Art to Self, which she started early this year and has seen incredible growth from it. It’s a website and newsletter of daily art and inspiration sent straight to your inbox. I have to say it really does help my mornings.

Now, let’s hack Stephanie Halligan.

I want to take this opportunity to thank our sponsor, FreshBooks. They’re designed for small business owners. FreshBooks is the number-one cloud accounting solution that helps millions of entrepreneurs and small business owners to save time billing and get paid faster. With FreshBooks’ award-winning mobile apps, you can do it all from anywhere on your Android or iOS devices. To start your 30-day free trial today, go to, and don’t forget to enter ‘Hack the Entrepreneur’ in the ‘How did you hear about us?’ section.

We are back on Hack the Entrepreneur, and we have another brilliant guest. Stephanie, thank you so much for joining me.

Stephanie Halligan: Thanks for having me, Jon.

Jonny Nastor: Oh, it’s my pleasure. Okay, Stephanie, we’re going to go straight into this.

Stephanie Halligan: Awesome. I’m ready.

Jonny Nastor: Awesome. Stephanie, as an entrepreneur, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Carving out Time to Do Work That Matters

Stephanie Halligan: Oh, that’s a good question. I think it’s a recent practice of mine, which is carving out time. It’s hard to do that, and there’s plenty of excuses I know I would make for not finding time and not putting myself first or working on my own stuff before client work, before calls, before actual work — putting my own stuff first. I read the book The War of Art, which is one of my favorite books, and it really inspired me to carve out time, especially first thing in the day, to do what I love and what I want to do and build my own thing.

Jonny Nastor: Nice. War of Art is a brilliant book as well. I read it just this past year, twice actually, and it’s really inspiring. The carving out time — you’ve shifted recently from one business to the next, right? From The Empowered Dollar, which was your personal finance blog, then into Art to Self, which is a daily email you send out and a daily post you do, right?

Stephanie Halligan: That’s right.

Jonny Nastor: Are you forcing yourself to carve out time, like, “I have to. They’re expecting it. I have to?”

Forcing Ourselves to Stay Consistent in Our Work

Stephanie Halligan: Right. It’s true, though, because as a daily art newsletter, it’s held my feet to the fire a little bit. If I have to produce something every single day, I personally want a routine where I put myself first in the morning, but now I have to. People are expecting something every single day in their inboxes. It was a nice way to hold me accountable to carving out my time and putting what I want to do first, which is drawing and writing. It definitely has become a practice of putting what I want to do first, and Art to Self was a really good way to make sure that I did that every day.

Jonny Nastor: I love forcing ourselves to do these things and stay consistent. I’ve only been on your list for about two weeks now, and I haven’t seen you miss a day. Have you missed one yet?

Stephanie Halligan: No.

Jonny Nastor: Nice.

Stephanie Halligan: It’s actually been a really fun process. I’m not going to miss a day. I can already tell. It’s something I love to do, but also even on the days where it might be 10:00 at night and I don’t have tomorrow’s post yet because I’m just not feeling it, usually those are the best Art to Self notes. Those are the ones where I’m like, “Why am I procrastinating this? What’s holding me back right now from actually doing work?” Usually, those are the best cartoons and the best messages that come out of moments where I kind of don’t want to do Art to Self.

Why Consistency Is the Key to Finding out How You Work

Stephanie Halligan: It’s been a really nice journey. Some days I’ll draw seven in a row and schedule them out, and some days it’s like, “Oh, I have to do this, and what’s the message I need to write and draw about today, and why am I pushing this off?” It’s been a really cool process to watch, and daily is definitely a huge shift in how I think about my business and put content out there every single day.

Jonny Nastor: Yeah. I love it. The consistency is, I think, key as well. You found out how you work. It’s good.

Stephanie Halligan: Right.

Jonny Nastor: Stephanie, I’ve found — talking to 80 different entrepreneurs now — that there’s a time in every entrepreneur’s life when they realize one of two things. Either they have this calling to make something bigger than themselves and some difference in the world, or they simply just cannot work for somebody else. Could you tell us which one of these two you are and when you discovered this about yourself?

How Stephanie Managed to Get Her Voice out There

Stephanie Halligan: That’s a great question. I think for me it started with contributing something bigger in the world and getting my voice out there. Even when I had a full-time job, I started a personal finance blog because I wanted to share my own story of how I was getting out of student debt, and I wanted to help other people and save other people from the financial disaster that I got into, which was tens of thousands of dollars of student loans.

That was my impetus to getting into the online entrepreneurial space. While I was still working, I was hungry to get out there and to help people and to really own my own voice and be a thought leader in whatever space I was in. That was, I think, pretty early on in my career, just realizing that I wanted to be me, myself, and I, and I wanted to help people no matter what job I was in. I was always kind of that side-project, side-hustle person while I had a full-time job.

Jonny Nastor: Nice. You wanted to own your own voice. I like that.

Stephanie Halligan: Right. Yeah, exactly.

Jonny Nastor: That’s cool. How long has Art to Self been? How long have you been doing this?

Stephanie Halligan: I’ve actually only been doing Art to Self for two months.

Jonny Nastor: Really?

Stephanie Halligan: January 1. Yeah, three months. Yeah, it feels like it’s been a journey to get here, which is starting a personal finance blog and then seeing how that got a little bit of notice. Then it was adding comics to the personal finance blog and that getting a lot of traction. Then it was realizing that I wanted to really focus just on cartoons and comics that I wanted to draw, not just about personal finance or money.

Then Art to Self was born from that idea, I think out of just chipping away at what I really wanted to do and what I was really good at. As soon as I launched Art to Self, the response was overwhelming. The subscribers just kept climbing. It’s donation-based as a business, and donations kept happening. Again, it’s so funny because it’s only been going a couple of months, but as something that’s daily, it feels like a lifetime for me personally. I’m just really grateful for the kind of growth that I’ve seen from it, so it feels a lot older than it actually is.

Jonny Nastor: Yeah, it’s interesting. We were talking before the interview, and you said that how it’s grown just so much quicker than you expected. Looking back over the last couple of months, do you know why or how? Do you think you’re responsible for it, or did it kind of get some exposure somewhere that you weren’t really expecting?

Stephanie Halligan: It’s funny because I think I’ve been trying to control where it goes, like in any sort of online marketing, but it’s really been word-of-mouth, literal word-of-mouth where I have friends who know me, so as fans of my cartoons or my work. Or they’re friends who have told their co-workers in their office, like five co-workers to sign up for this, so their co-workers all get the same email. I have other entrepreneur friends who are coaches, and they tell their clients to sign up for Art to Self.

It’s this word of mouth. I’ll get reader emails, and they’re like, “So-and-so, a friend of a friend of a friend showed the site to me.” I saw a random link on Reddit where someone had posted an Art to Self cartoon that said, “A friend of a friend introduced me.” The way it’s spreading, it’s really cool to watch, and it’s really organic. I think it’s really resonating with people. When it resonates with them, they’re willing to share it in a way that I don’t think I’ve ever had any of my stuff shared before.

Jonny Nastor: That’s got to be a very, very cool feeling.

Stephanie Halligan: Yeah, it really is.

Jonny Nastor: That’s cool. Okay, Stephanie, we’re going to move to work, because you’ve now gotten to carving out time and doing this work that you have to do every day — getting the email out, getting the post up — and then doing everything else that you have to do within this business and in your life.

Today’s a workday. Could you walk us through, say, the first 30 minutes of your day that you did — your routine, whatever it happens to be, to set yourself up to get everything done that you needed to get done today?

Stephanie Halligan: My routine before actually sitting down to work at a laptop?

Jonny Nastor: Yeah. What do you do those first 30 minutes when you get up?

Stephanie Halligan: Oh, it’s really structured. I’m a sucker for routine. I live in D.C., and right now I’m in Boulder, Colorado, because I can take my business anywhere. For the month of March, I’m testing out a new city, so for me it’s really cool to have that kind of freedom, but it makes my routine all the more important. I think there’s a couple of things that I must have in the morning to get things off to a good start.

One is a really good, slow breakfast. I do eggs and vegetables and sweet potatoes and really take my time and usually listen to a podcast or music. The second is meditation. It provides me with this clear-headed foundation for my day. It’s really easy for me to get caught up in my to-do list, so that’s been a pretty recent practice of mine. I’ve been doing it every day, and it’s really changing the mental space. Talk about carving out time — just carving out that 10 minutes or 20 minutes has been life-changing. Then I think the third would be coffee, making it and drinking it. That has to happen.

Then when I sit down to work after that personal routine happens, I try to focus on creating something, either writing or drawing or brainstorming, but really doing something more on the creative side first thing when I sit down to work so that it gives me some positive energy, even if it’s just a half an hour of that for the rest of the day.

Jonny Nastor: Nice. You’re in Boulder. Is this the first time you’ve gotten to be remote or work out of somewhere else?

Stephanie Halligan: Yeah. I’ve been running my own business for about a year and a half now, so I would take trips here and there. I have family in Seattle, so I would go there for a week or two and visit friends in a different city. This is the first time I’ve actually picked up my life. I’m here for a whole month with my boyfriend, and it’s living time. Today is a workday, and I had a morning routine. We’re exploring the city and the mountains and everything, but it’s living in a new city, and I think that’s the first time I’m trying this out, which is taking it slow and really trying to live in a new place.

Jonny Nastor: That’s awesome. I love it. I like that you’re so regimented in your morning and you take the time, but in a slow, sort of deliberate way. I like that. We talked about what you are good at, and we just went over it again, carving out the time for yourself and to get what it is you need done. Could you tell us, Stephanie, something in your business that you are not good at?

Stephanie Halligan: Oh, yeah. I don’t know if I’m not good at it, I just dislike it, which is the marketing piece. Getting myself out there, it’s that feeling that it feels spammy, even though I’m not a spammy person. But asking to have my story shared, or pushing social media, every time I pin something to Pinterest or send a Tweet, I just cringe. It might not be a bad thing, because you shouldn’t live your whole life on social media and expect traction without a strategy behind it.

I have dreams of very soon hiring somebody to help me with strategic marketing on social media, on other things. It’s definitely the part of my business that I’m just not comfortable with, versus creating stuff, which I could do all day.

Jonny Nastor: Yeah, which is understandable. I think a lot of people struggle with that. It’s cool because what you create, it is marketing. It’s content that’s so easily sharable by everyone. That’s amazing.

Stephanie Halligan: Right.

Jonny Nastor: That is marketing through content. That’s brilliant. That probably is perfect. It is perfect for you because you’re not just here sharing a sales page to something. It’s literally cool, sharable content that is instantly digestible by someone that can benefit from it. That’s awesome.

Stephanie Halligan: That’s my focus and my hope, which isn’t bad. I’ve been trying to give myself permission lately to not really focus on a growth strategy and just see where it goes naturally. Then, as things pop up, to take advantage of them and if I see a spark somewhere, to add a little fuel to that fire.

I’ve seen it happen where sometimes I’ll take quotes from people who inspire me, and I’ll send them the cartoon. I sent Seth Godin a cartoon of a quote that inspired me. I sent it to Elizabeth Gilbert. She’s the author of Eat, Pray, Love and she has a lot of cool TED talks about inspiration and creativity. I sent both cartoons their way, and I got a reply back from Seth, which was amazing, just thanking me and telling me that he enjoyed what I did. Elizabeth Gilbert ended up sharing it on her Facebook page, which was really exciting.

I think for me, it really reaffirmed that creating the content itself is a natural marketer. I have to push it a little bit and share it and get it out into the world, but if you focus on creating something really good, it can’t help but be shared.

Jonny Nastor: Exactly. You also took the initiative, and I can imagine that you were probably a bit apprehensive of emailing those two people.

Stephanie Halligan: Right. Yes.

Jonny Nastor: It totally worked. That’s amazing.

Stephanie Halligan: Right.

Jonny Nastor: It’s true. Again, you weren’t just sending them to a sales page like, “Oh, can you send all your readers to my sale page?” That would be dumb, right?

Stephanie Halligan: Right.

Jonny Nastor: You did it to something super valuable to them and their audience. That’s cool.

Stephanie Halligan: Yeah.

Jonny Nastor: In the last year and a half, you’ve gone from the one blog on personal finance, morphed that from a straight blog into a blog with cartoons, and now just to cartoons, which is a lot of pivots and changes, which is really cool. Would you consider yourself a serial idea-starting person where you come up with these ideas and you just go with them?

Stephanie Halligan: Oh, yeah. That’s a great question. I would say that I’m pretty calculated with my ideas to the point where I think it used to stop me before. I was sitting on the idea of writing a personal finance blog for two years before I actually did it, and blogs are so easy to start. There was no barrier to entry, really. I just felt like I didn’t know everything a hundred percent all the way. There was a lot holding me back. Then I sat four or five months with the idea of doing cartoons, I think almost trying to talk myself out of it and being like, “Okay, is this really going to work?” I cautiously tiptoed into that and watched it really take off.

The Power and Compound Effect Of Daily Content Creation

Stephanie Halligan: When I had the idea for Art to Self, it was in November, and I was like, “I just need to get this up.” I set a January 1st launch date, because it’s going to be a daily thing, so I might as well start on the new year. I’m going to put up a landing page and start collecting email addresses and just tell people about it and say, “It’s launching January 1st.” I don’t have the choice. I don’t have the choice to delay or back out of it.

My work has usually been iterations and refinements of what I’m already doing, so I wouldn’t consider them serial entrepreneur ideas. My struggle has always been the opposite, which is slowly, cautiously putting ideas into action and trying to talk myself out of it or being scared to press the ‘publish’ button, but I’m getting a lot better at doing that, for sure.

Jonny Nastor: That’s nice. You didn’t set up a buffer or anything like, “I’m going to do thirty drawings first before I launch so that I have this buffer?” You just said, “Nope, I’m going to make them daily?”

Stephanie Halligan: Right.

Jonny Nastor: That’s awesome.

Stephanie Halligan: I tried to do that. Yeah. I was like, “Okay, here’s the plan.” Then I realized it didn’t have to be. Originally, too, they were going to be full-color cartoons and not have any text with them.

As launch date approached and there was pressure to launch, I was like, “There is no way this would be sustainable or fun for me to do full-color, really detailed cartoons every day. I think I need to add some text to these for SEO purposes, but also there’s a lot of story behind the cartoons that I’m drawing, and I want to share that, too.” They became black and white, very simple, and that has actually made the business easier to run, but also more sharable, and they stand out a lot more. It was interesting what the pressure of going and launching and forcing myself to get going did to actually shift what I was offering, too.

Why It’s Okay to Not Know Everything before Starting

Jonny Nastor: Yeah. I like that. You obviously had more confidence going into this because you had already launched a blog for a significant amount of time. It was interesting when you said you put off launching the first blog for two years because you didn’t know 100 percent of everything. None of us know anything that we’re doing until we do it. I had no idea how to podcast until I launched a podcast. It’s just kind of how we have to do it.

Can you remember how you convinced yourself that you don’t need to know a hundred percent of it, or “I’m just doing it anyways,” or how that works?

Stephanie Halligan: Yeah. For me, again, I think the pattern that really I’m seeing in my own entrepreneurial life is, how do I bring in outside forces or outside pressure to help me take action? When I was just starting a blog, my barrier was the technical stuff. I don’t know how WordPress works. I don’t know what the back end would look like. I don’t know how to design stuff. I was like, “If that’s my barrier, I’m just going to hire somebody, and then I won’t have a choice. I won’t have a choice to make an excuse that I can’t get started.”

For me, it was really drilling down into what was the excuse that was holding me back, and how do I just make that not an excuse anymore? So I ended up hiring someone really affordable to help me build the bones and teach me WordPress, and I had this blog built. It’s ready to go. I had no more excuses anymore, and I had to start writing.

I think it’s about finding ways to overcome whatever it is that you might be telling yourself is your excuse for not getting started. Putting up some public accountability always helps, too.

Jonny Nastor: Yeah, definitely. I think that that technical barrier is really a common one. It was for me, too, even though it is really easy once it’s set up and you just go in there and do it. Once you’ve done it once, you’re like, “Oh, I get this.” I think it’s just something we use obviously as an excuse to not get going. There’s so many ways. There’s so many free tutorials. WordPress itself is free. You can get brilliant themes for free. It doesn’t have to be completely unique. It doesn’t have to be awesome. You just have to start, and you can change it at any point.

I find it interesting that that always seems to be so much, like, “I don’t know how to work these websites. I don’t know what the back end will look like.” Really, it’s not that big of a deal.

Stephanie Halligan: Right. I think, too, even when I was leaving my job, there’s always that you want to control what’s going to happen next. You want to know that you have all your ducks in a row, and you have everything figured out. I also just remember leaving my nine-to-five and having a freak-out moment before I put in my notice where I was like, “I can’t quit. I can’t quit office life because I don’t own a printer or a scanner.” I just caught myself and was like, “No. That’s not a reason not to quit.”

Jonny Nastor: Oh, no.

Stephanie Halligan: Right. For me, I didn’t get my bookkeeping together until a year after already starting my own stuff. I was nervous of even leaving before having everything set up.

I think that there’s a natural desire to want to know how to do everything or what everything is going to look like before you take the leap. You just really can’t until you actually start doing it, and then you actually see how it works, and then you can tweak and experiment and understand what needs to happen. I’ve tried to over-prepare before I take these kind of jumps, but it’s kind of the reverse, which is needing to jump first and then learning as you go.

Jonny Nastor: Yeah. Very well said. Okay. We are going to end off on the future of Stephanie and Art to Self. You are only a couple of months into it. You seem quite impressed with the success and the reach you’ve had so far very early on. Can you tell us what it is you are hoping to accomplish with Art to Self in, say, the next year?

Stephanie Halligan: Yeah. Art to Self has been such an interesting project because it’s daily. It’s been a slow game and a slow burn, and even for myself as an artist, I get to draw and put it out, draw and put it out. I’m watching myself evolve as an artist and a writer, which is really cool.

I think the structure will stay the same, but my hope is that the readership grows, that I can keep doing this daily, that I am supported by donations from my readers, and that my subscriber list keeps growing naturally. Ideally, I would love to turn this into a book, so taking the inspirational quotes and cartoons, putting them into A Hundred and One Quotes or Art to Self for Entrepreneurs or some sort of book or even a desk calendar.

I’m hitting the point where I now have a hundred posts and cartoons online, and it’s just going to keep growing from there. So what do I do with all of those assets and the more popular ones? I even got a Facebook message yesterday from one of my readers who took her 20 favorite Art to Self cartoons and printed them out and put them all in kind of a collage in her office and sent me a picture of it. She made her own Art to Self poster.

I feel like I’m going to let it lead me, if that makes sense. I think it might take me some really cool places, and I think it will grow in some ways I might not even know yet. I’d love to turn it into something that’s tangible like a book sometime this year.

Jonny Nastor: Awesome. I’m sure you will, because as you say, it makes perfect sense that it should really be in a book sitting on everybody’s coffee table or in offices on tables. It’s great medium for that, I think.

Stephanie Halligan: Yeah.

Jonny Nastor: I think we’ve enticed all the listeners now about getting this daily art inspiration to their email inbox. Could you, Stephanie, please tell them explicitly where to go and get onto this list.

Stephanie Halligan: Sure, That’s the landing page where you can sign up to get these daily art notes and inspirations in your inbox. They come out every single day, and like I said, I haven’t missed a day yet. If you’re looking to start your day off on a good note, a little positivity to get your day going, head over to and sign up there.

Jonny Nastor: Yes. I strongly recommend it, because I’ve been on it, as I said, for almost two weeks now. Even though we know we shouldn’t be checking our emails first thing in the morning, sometimes when we’re lying in bed still, on our phones, to get that one is actually really good, and it usually puts a smile on my face and kind of sets up the day nicely. I strongly recommend it, and I will link to Art to Self in the show notes so it’s easy for everyone to find.

Stephanie, thank you so much. I wish you the best of luck. Please keep doing what you’re doing, because it’s awesome to watch, and it’s very inspirational. Thank you.

Stephanie Halligan: Thank you. Thanks, Jon.

Jonny Nastor: Stephanie, thank you so much for joining me, and thank you so much for the work that you do every day now that comes to my inbox and thousands of other people’s, because it’s definitely making a difference. It really is awesome. I hope that everyone will go to Check it out. Subscribe to her newsletter. It’s completely free — get her inspirations sent to you once a day. I definitely recommend it to everyone. Please check that out.

Stephanie said a lot of smart things. She did. She said a lot of smart, interesting things, but she said one thing, didn’t she? She did. She said that one thing. Did you get it? Did you hear it? Let’s do it. Let’s find the hack.

Stephanie Halligan: … and how do I just make that not an excuse anymore? So I ended up hiring someone really affordable to help me just build the bones and teach me WordPress, and I had this blog built. It’s ready to go. I had no more excuses anymore, and I had to start writing. I think it’s just about finding ways to overcome whatever it is that you might be telling yourself is your excuse for not getting started.

Jonny Nastor: That’s the hack. Yes, Stephanie, exactly, exactly, exactly. Thank you for sharing that. You had no more excuses. You had the blog built. It was technical reasons or whatever it was you were telling yourself, and you just overcame it. You found somebody who could do it for a price you could afford, and you did it.

Remove those barriers. Those barriers are there, and you are the only one who can figure out what those barriers are, and they’re not big. They’re not as big as you make them out to be. Break them down into small things. Stephanie figured out that it was just figuring out WordPress, so get a site built. It’s not expensive. It’s not hard to do. Then she had no excuse. She just had to start writing. That’s awesome, and it’s true. You just have to figure out what those barriers are. Nobody can do it for you. Just get rid of those excuses.

Stephanie, thank you for that, because that’s kind of epic. It seems so simple. The key to all of this is to overcome these barriers all along, no matter if you’re just getting started or you’re just creating your first product or you’re just creating your first podcast or you are trying to find your first mastermind group. These are all things that we get, these little barriers, and we can’t do it.

Figure out what those barriers are, get them overcome either by somebody else or by you. But get through them and move on, because all the time you get stuck is just time that you could be doing such cool, awesome things. They’re just excuses, so please work yourselves through them.

Stephanie, thank you again so much for all that you do. Thank you for joining me for the top hour. It’s been a lot of fun, and I really enjoyed it. — check it out, please. Get on the email list. I would love to be able to write you. Every Sunday afternoon, my emails go out, and it would be great to have you there. You can hit reply to any of those emails or hit me at That’s my email. Have any questions, comments, concerns, I don’t know, just tell me your favorite movie. Say ‘hi.’ It’s cool. Hit me on the email, and it would be great to hear from you. Check out the website. Get on the email list, and I will be writing you my best stuff every Sunday.

Stephanie, thank you again, and thank you for listening and taking the time to join us here at Hack the Entrepreneur. I truly do appreciate it. Please, until next time, keep hacking the entrepreneur.