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*Formerly known as Solopreneur: The One-Person Business Podcast*
Welcome to The Aspiring Solopreneur, the weekly podcast that dives deep into the world of solopreneurship. Join us as we bring you insightful interviews with industry experts and successful solopreneurs who have mastered the art of running their own businesses.
Are you a solopreneur looking for guidance on how to attract clients? Or maybe you're searching for ways to stay motivated and overcome the challenges of working alone. Perhaps you're even struggling with the intricacies of taxes and financial management. No matter what obstacles you face, The Aspiring Solopreneur Podcast is here to provide you with the knowledge, inspiration, and practical advice you need.
In each episode, our hosts, Joe Rando and Carly Ries, sit down with a diverse range of guests, including seasoned solopreneurs, marketing gurus, financial experts, and productivity specialists. Together, they unpack the secrets to solo success, sharing their personal stories, strategies, and actionable tips.
Learn from those who have paved the way before you, as they reveal their tried-and-true methods for growing their company of one.
Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's Intro gives you free education, community, and tools to build a thriving one-person business. So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, be sure to check out LifeStarr Intro!
Access LifeStarr Intro: https://www.lifestarr.com/lifestarr-intro-for-solopreneurs
In this eye opening episode, Joe and I sit down with ADHD business coach and former academic Skye Waterson. We unpack why traditional productivity advice fails so many solopreneurs and what actually works instead. You'll hear why overwhelm creeps in as business grows, how to prioritize without rigid systems, why your to do list might be sabotaging you, and how to build simple systems that support your brain instead of fighting it. Sky shares practical strategies for delegating without perfectionism, using AI to offload mental clutter, designing your environment for better focus, and even why you should reward yourself for starting, not necessarily finishing. So if you ever thought, why does this feel harder for me than everyone else?
Carly Ries:This conversation will feel like someone have finally turned the lights on. You're listening to the Aspiring Solopreneur, the podcast for anyone on the solo business journey, whether you're just toying with the idea, taking your first bold step, or have been running your own show for years and want to keep growing, refining, and thriving. I'm Carly Ries, and along with my cohost, Joe Rando, we're your guides through the crazy but awesome world of the being a company of one. As part of LifeStarr, a digital hub dedicated to all things solopreneurship, we help people design businesses that align with their life's ambitions so they can work to live, not live to work. If you're looking for a get rich quick scheme, this is not the place for you.
Carly Ries:But if you want real world insights from industry experts, lessons from the successes and stumbles of fellow solopreneurs, and practical strategies for building and sustaining a business you love, you're in the right spot. Because flying solo in business doesn't mean you're alone. No matter where you are in your journey, we've got your back. Oh my goodness, Skye. We are going to get into such amazing an amazing conversation today because I think what you cover is relevant to so many people, whether they have an official diagnosis or not, or just are spread across the board. I'm so excited to dive into our topic and relate that as a cliffhanger, even though our audience already heard about it a little bit in the intro. But let's start with our icebreaker question. What is the wildest things that's happened to you as a solopreneur?
Skye Waterson:The wildest thing that happened to me happened probably in the first two years of working. I got contacted by the New Zealand government. They found that their intelligence services were getting diagnosed with ADHD at an incredibly high rate. So intelligence services are people who worked in kinda like you know figuring things out, working on a hunch, that kind of thing. They were getting diagnosed with ADHD at such a high rate.
Skye Waterson:They needed somebody to come in and basically talk to their managers about how to manage ADHD. And so I ended up working for the New Zealand government teaching them how to work with their team in the intelligence services which was definitely a big big moment. You're like, oh, people are paying attention. That's interesting.
Joe Rando:I could have used your help about ten years ago when I started managing salespeople.
Carly Ries:Across the board.
Joe Rando:Actually, before we dig in, I'm curious. So, it's one thing to be a coach helping people with ADHD, but when the government gets involved and has you come in to talk to their intelligence services, it sounds like you've got some credentials beyond just, a website. What is your background that the government was willing to reach out to you and engage you?
Skye Waterson:So I am a former academic. before I was a coach working with ADHD, I did a masters. I actually got diagnosed with ADHD at the beginning of my PhD. I am a PhD dropout because I left to start this business once I found out I had ADHD and had started working with, you know, government and other individuals.
Skye Waterson:It's been a wild ride.
Carly Ries:yeah. it's one of those things where it's like, just buckle up. Let's see where this entrepreneur journey takes me. Like you were saying, you were diagnosed with ADHD while you were going for your PhD. What were the first business struggles that made you realize traditional productivity advice just wasn't working for you?
Skye Waterson:It was really just the constant sense of overwhelm. It was the way that and this is something that I'd learned doing my PhD and researching and then it really came into running a business as well. The way that everything starts out feeling, you know, in control and exciting and then inevitably it starts to get bigger and it starts to get more there's just more coming at you and if you have ADHD, you don't have the skills to handle it and keep going especially when you're working by yourself because you are responsible for a lot of the different moving pieces and different moving pieces is kind of the anathema of ADHD people.
Joe Rando:That's so interesting. My wife is a child therapist and she does a lot with ADHD. And she said to me one time, we were talking about a vacation, I said, well, that's right when school starts. And she goes, that's fine. No problem.
Joe Rando:She goes, October, that's when everything starts to fall apart. So it's the same thing with the kids. It's like, starts out, everything's fine, but then all of a sudden, it starts to fall apart later.
Joe Rando:Interesting. So, yeah, it doesn't matter the age.
Skye Waterson:No.
Carly Ries:So when people are diagnosed with ADHD, how does that diagnosis change the way they see themselves as business owners specifically? And how can they kind of rebuild that trust with themselves and work with their brain instead of fighting it?
Skye Waterson:Yeah. So the biggest thing that it changes is it means that you're perceiving the world differently. And obviously, you were always perceiving the world differently, but now you know and you know what it is. And so what you learn is hey, I am engaging and I'm interacting in a way that is different from other people and therefore really importantly, different from how other people are recommending that I do things. I talk about this sometimes with contracts and things like that.
Skye Waterson:They're built to create more paperwork and that is particularly complicated and difficult when you have ADHD. So a lot of what we're looking to do is we're looking to simplify and we're looking to support the main areas of struggle which are, you know, in executive functioning it's like working memory, time blindness, struggles with transitions. And then also obviously you've got that shiny object syndrome, dopamine, ADHD side as well that we need to manage.
Carly Ries:So what are some practical like prioritization methods that work specifically for people with ADHD or even just overwhelmed solopreneurs who don't like rigid systems and by the book advice.
Skye Waterson:Yeah. And I will say as well, when you look at ADHD symptoms amongst people who run their own businesses, the number of people who have ADHD symptoms goes up to like thirty percent. So you might think, this is a small group of people, but not when you're looking at entrepreneurs, which is often worth mentioning. But yeah, if we're looking at how to then prioritize with that in mind, I have a system that I have taught for, oh gosh, nearly five years now of how to do this.
Skye Waterson:And basically, it takes you through a version of the Eisenhower matrix that is very specifically built for our brains. And I'm happy to share that today if you guys would like.
Carly Ries:Please. We'd love that. We're very well versed with the the Eisenhower matrix.
Joe Rando:Well, we are, but I don't know if all the listeners are. So the Eisenhower matrix is basically two dimensions. There's important, not important, urgent, not urgent. So you've got four squares, four quadrants, and you spend most of your time hopefully in the important and urgent quadrant, but you want to spend some time in the important but not urgent quadrant to kind of we call it working on the business. So that's the baseline.
Joe Rando:Now you're gonna take us to something Specific
Skye Waterson:So one of the things that is often a struggle is when you're doing something like the Eisenhower matrix with ADHD, you're supposed to be able to hold everything in your head and kind of imagine where it goes. Sort it as you go. And that's particularly difficult for a variety of reasons. We tend to be very optimistic about what we can do and we also tend to struggle to hold a bunch of things in our brains. So in terms of working memory, long term memory is great.
Skye Waterson:So what we wanna do instead is we wanna take a minute. We wanna note down everything that is in our head. So grab a document or something like that. Note down everything that's in your head and that's every single task. So it could be a work task, a home task, write them all down.
Skye Waterson:Then we're gonna filter them. So this is a prioritization filter. And actually I have an AI that takes you through this and I'll tell you in a second how you guys can grab that if you want. It's free. But basically you're going through the list.
Skye Waterson:You've written everything down. Now the next thing you wanna do is you wanna identify what is truly urgent as in it has to be done tomorrow or there will be a significant negative external consequence. And the way that I help people think about this is if you ended up in a waiting room for some reason and that was your day, what is the thing that you would still try and do on your phone or you would have to contact someone and say, hey, this isn't happening tomorrow because I'm not gonna be prepped because of what happened today. That is urgent. Everything else doesn't go in the urgent bucket and that's where people go from you know, swearing they've got 50 things they have to do today to having two or three.
Skye Waterson:I very rarely have anyone get more than five. So that's the first step.
Carly Ries:Yeah. Wow. I mean, putting it in that way I'm like, I'm done with work after this because everything off my list is music to Joe's ears, I'm sure.
Skye Waterson:Well So that's the thing. So people go, oh, cool. This is initial feeling of relief like, okay, I don't have to do this all today.
Skye Waterson:But then it quickly follows up with, yeah, but Skye, what about everything else? what are we not supposed to do things? So then the next thing we do is we do the same thing for seven days out. So the exact same system. If you're in a waiting room for seven days, etcetera etcetera.
Skye Waterson:And that gives you a sense of what you have to do this week. And then from there, you go, okay, this is what's urgent. Now you have maximum time and space to do the thing that is most important. When you work with me, one of the things we do is we figure out what's important, what's the most broken part of your business, what's the thing you need to do. Often it's not the squeakiest wheel, it's actually the quiet like you really need to go ahead and build a system for this thing because it would take you five hours less a week and you keep doing it on the fly, all of those kinds of things.
Skye Waterson:So we build blocks of time into your week to do the top one to maximum three most important things. And then everything else, you know, one of the things I say to people is your job in life is not to do your task list. It's to do the things you have to do and then the things that will help you build the engine that will help you do your task list over time. And those are the the most important things. But like I said, if you want that, you can just message me, Carly and Joe on Instagram at unconventional organisation and then I'll know it came from here.
Skye Waterson:And I'll give you guys the whole system for free because this is something I don't think anyone should be struggling with. It's overwhelm and a lot of people do.
Carly Ries:Yeah. Well, that's awesome. Thank you so much. We'll put all of that in the show notes as well. But I'm so glad you said working on things that will help you get your to do list on your task list instead of you actually doing it.
Carly Ries:And a lot of times, whether it's automation or whatnot, delegation can be a part of that. But people are often hesitant to train other people because they're like, it'll take me longer to train somebody than to just do it myself. How do you coach people through that mental block and actually get them to get things off their plate?
Skye Waterson:Well, it's an interesting one now because the answer that I gave in 2024 is different from the answer I gave in 2026 for probably very obvious reasons. Number one, is you don't have to give it to somebody. You could create a custom gpt. They're very fast to make and I do show people how to make them.
Skye Waterson:And that can save you a lot of time and effort. So there are ways to do it without working with people. So for people who struggle with working with people or don't wanna hire, that is kind of a step one. And then in terms of actually delegating it, the key is when you're looking at I mean, hiring and delegating are two very different things. So hiring is a task.
Skye Waterson:It does take a little bit of time and you know, even if you've got someone on for five hours or maybe especially you've got someone on to help you out that can can make it really difficult. But if you're delegating, it's really important that you focus on giving them the task of writing down what they do. So kind of explaining it to somebody and then getting them to try it, come back with questions, and then you are saying, okay cool. You know, like writing the task down. So one of the things that stops a lot of people is they think they have to have a perfect document that outlines every step of a task before they can hand it over.
Skye Waterson:And if we think like that, no one would ever get any tasks handed off. I know I wouldn't.
Joe Rando:What's this? What about using Loom to record yourself doing it?
Skye Waterson:You can definitely do that. I have a personal preference towards talking it through with an AI. So hitting record and just saying I wanna do this, I wanna do that, I wanna do this, make an SOP for me that is in order. And that is often faster. And the reason for that is because while Loom was, and again this is such a fast space to be in because the answer two years ago would have been Loom.
Skye Waterson:Sometimes we get distracted when we're working on something. We're like working on something and then we're doing something else and then we're playing music in the background. I'm just talking about myself here. I've always found that, I pity the poor person who has to watch my loom because I'll be focusing on something and then maybe I'll switch to something else or chances are, if I'm delegating a task, it's because that task is super boring to me and I never ever ever wanna do it again. So to have to do it again while being recorded is often a little bit out of my ADHD realm.
Skye Waterson:So I prefer to do the AI version.
Joe Rando:Question? based on what you just said. Do you use music to help you with focus?
Skye Waterson:Yes. I do. I actually use the Spotify DJ. Shout out to them for figuring out how to make that.
Carly Ries:Yeah. I mean, Joe, you know this. I use an app called Coughativity. So it sounds like a coffee shop, you have that background noise, like you're working with some or even in your in your kitchen.
Joe Rando:I listen to Ludovico Inaudi. What?
Carly Ries:Bless you.
Joe Rando:He's a kind of a modern classical composer that plays the Nice. And it's just chill and Yeah. Focus music.
Skye Waterson:I'm aging myself here, but that was my first thing was I used to have CDs of, like classical music and I would play it.
Joe Rando:For those of you not watching on YouTube, I don't know what she's talking about aging herself because I'm here.
Carly Ries:I'm pretty sure I can remember them both also. So that's hilarious. Okay. So we're talking about delegating, but you were also talking about systems and getting those in place. But even thinking about putting systems in place is overwhelming for a lot of people.
Carly Ries:What's one system that you'd recommend somebody implement today to at least just kick things off and maybe build that momentum to create more systems?
Skye Waterson:Yeah. The number one system, and I recommend it, I actually ask my people when I'm working them to do this, we often do it together, is I want you to build a map of your business. So many people haven't done this and they just feel a sense of anxiety. Not only building a map of your business but also of of you can build a systems and SOPs even if they're for you into that map. So a lot of times when people are thinking about their business, they're looking at an organizational chart.
Skye Waterson:That is not a map of your business. That's a map of the people in your business. When I talk about a map of your business, what I'm talking about is how do you acquire customers? And I'm not talking about referrals although referrals are great. Like how are you actually acquiring, people who don't know you.
Skye Waterson:Then how are they coming through your lead flow process and then how are you selling to them and then how are you delivering to them and then you know, ideally how are you getting them to stay or you know, growing what they they pay you over time. That is the initial map. I call it the SOP pipeline because once you've drawn that map, you will immediately see, oh, we have this thing that we're doing that isn't connected at all and it's just over here free floating. Surprisingly often that's the case or we don't have any acquisition. We've just been running on referrals and now that's starting to run dry.
Skye Waterson:That feels really anxious. And if you can create a really simple reasonably high level version like don't go to you know, and then Susie does this and I do this and you know, keep it high level. You can then move those pieces around and decide who does what in the pieces of your business. And that provides the basis for you feeling a sense of control over what you're doing.
Joe Rando:I like that a lot.
Carly Ries:Yeah. Same. Well, so okay. so you help people combat overwhelm. You help them, like, harness I would say harness their ADHD superpower for good, for their business.
Carly Ries:For scaling that business, so we were talking about AI, maybe this is gonna come into play here as well. How can a one person business scale without feeling that overwhelm or feeling like they're adding those must get done things in the waiting room to their list? What is your advice there?
Skye Waterson:It's a good question. And I think the first thing to do, and this is what I ask everyone to do, figure out which piece of your business is the most broken. Because they're all breaking as we grow and scale, and focus on that piece first. And I will tell you this is somebody who is currently doing it, and it's really really really hard especially when you have ADHD and you wanna do a million things and you wanna run-in a million platforms. But to give you an idea, most people that I work with are struggling in two areas.
Skye Waterson:They're struggling or feeling overwhelmed in delivery aka they have a bunch of people coming in but then they are struggling to deliver on that. Especially if you're a solopreneur. You know, it's feast or famine sometimes and you have a ton of people and now you're on a wait list and things like that. So if that's the case, that's the bit we wanna streamline first. How do we productize what you do?
Skye Waterson:And this is the part where everybody I can hear you guys through the audio going, but it's custom. It's custom. If it's custom, you should be charging at least double what your normal rate is most of the time. Like, what you're doing should have some level of systematized, productized no matter what it is because even if you're working for yourself and you can be that person and those of us who are solopreneurs are like the worst at this, it's going to drive you insane to constantly change everything. You're not gonna be able to build any systems and you're not necessarily even providing the transformation or the outcome that people are looking for.
Skye Waterson:So you're not even getting a customer happy enough. Like the person who asks for all those changes might not be you know, running away and saying, oh this person's amazing. Like they really did want that really awesome, exactly what they wanted, every time service and if you are changing it, you have to, increase your price. Sorry. I think I went off on a tangent.
Joe Rando:No. But it makes total sense. I mean, if you're doing something different for everybody, you really don't have a solo business. There's no good way to have that.
Joe Rando:I mean and there could be exception. I Mean, if you're doing art, if you're doing sculpture, everyone's gonna be different. But for most businesses, if you're just doing something different and not just solo businesses. I mean, my last startup was a software company with employees, and we had one system. And when people wanted customizations, they paid us to do it, and it became part of the standard product. Because there was no way to have it be profitable to just give something different to everybody.
Skye Waterson:And when you're working with ADHD, that is what you need to do. You need to build something that is simple so that it can scale. And you know, you can offer more customization but you have to do it at a price where your cash flow is really being supported by that. And then the question becomes, okay, now how do I get dopamine from something that's not my business because my business is not chaos, it's actually working. And surprisingly a lot of people want that but then when they get it, they feel a sense of loss of that energy of everything's on fire.
Skye Waterson:And so one of the things we talk about at that point is how to get dopamine stimulation from other parts of your life
Joe Rando:Isn't that base jumping?
Skye Waterson:Yeah. Kind of. I mean, I know an entrepreneur who has to get on a plane to actually ride anything and likes to jump out of planes. But you know, for the rest of us, think about your senses. I mean, Carly, you talked about it a little bit, with the sound.
Skye Waterson:It's like, touch, taste, sound, sight, smell like what can you do to elevate your environment to a level that feels stimulating for you? And then what can you do to add in pieces of activity? I mean I've had clients who bought really expensive cars because they never actually took that walk that they were supposed to during the middle of the day. You would be surprised when you have ADHD brains, your desire for additional stimulation, it's not a want, it's a need. And you will get it one way or another.
Carly Ries:Such good advice. Okay. Well, so we're gonna end this with a big advice question. For someone listening to this, it totally resonates with them.
Carly Ries:Maybe they don't always feel like people on the podcast they listen to are speaking directly to somebody with ADHD and they're like, ugh. She gets it. I wanna hit the ground running. If they finish this and implement one change within the next forty eight hours, just one, what would you want that to be?
Skye Waterson:Oh, yes. So I would want you to start your work sessions with a reward for starting, not a reward for finishing. I can go into the neuroscience of it but just the way our brains work, it doesn't seem to connect as well the reward at the end. So if you can give yourself a reward for sitting down and starting. I know you've got the coffee all sorted probably so let's go sit down with a coffee but what else can we do?
Skye Waterson:Can we sit down somewhere that we like? Can we listen to some music? Can we, bring something cozy with us? Like what can we do to make this environment a bit more stimulating and have a bit of a reward for starting that's going to help you want to sit down and actually do it? You'd be surprised how effective that is as a base strategy for getting focused.
Carly Ries:yep. That's great words of wisdom. Okay Skye, we ask all of our guests this question. I'm very intrigued to know what you're gonna say. What is your favorite quote about success?
Skye Waterson:My favorite quote about success we've had in the business since early on. It's a rising tide lifts all boats. my goal is to help everybody who feels like they have an ADHD brain to be successful. The research indicates that we are not compared to other people who are running businesses. I just don't think it has to be like that.
Skye Waterson:So, you know, building these systems, teaching them to people, hopefully it helps other people.
Carly Ries:That's awesome. I think what you're doing is so great. Thank you so so much. If people want to find out more about you and think you could really help them, where can they find you?
Skye Waterson:So you can find me at unconventional organisation on Instagram. That's organisation with an s. You can DM me, Carly and Joe, if you want the focus formula to reduce overwhelm, get unstuck. My podcast is the ADHD Skills Lab. We talk about research.
Skye Waterson:We talk about business. It's a great time there. And if you wanna find me on the internet, you can find me at unconventional organisation in most places.
Carly Ries:Awesome. Well, Skye, thank you so so much for coming on the show. This is an episode, we actually haven't covered this topic yet and I'm so glad we did today, so thank you.
Skye Waterson:No worries. Thanks for having me.
Carly Ries:And listeners, thank you so much for tuning in. As always, please leave that five star review. It really helps us spread the word to other solopreneurs in your shoes. Subscribe in your favorite podcast platform, including YouTube, and share this episode with a friend who think who you think would find it helpful. And we'll see you next time on The Aspiring Solopreneur.
Carly Ries:You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.