ADHDifference

S2E9: Advice for ADHD Entrepreneurs & Creative Freelancers + guest Shelby Dennis

• Julie Legg • Season 2 • Episode 9

Share episode

Julie Legg sits down with Shelby Dennis, a freelance copywriter turned ADHD-friendly business coach. Shelby shares her journey from corporate frustration to entrepreneurial freedom, following a late ADHD diagnosis that helped reframe years of feeling “too much” in traditional work environments.

Now coaching other neurodivergent freelancers, Shelby brings lived wisdom to what it means to build a business that works with your ADHD brain. From questioning conventional business advice to designing creative systems, this conversation is packed with real talk for ADHDers trying to carve their own path.

Key Points from the Episode:

  • Shelby’s diagnosis journey and how recurring feedback at work helped her realise she wasn’t “broken”, just wired differently.
  • Why traditional business advice often fails ADHDers.
  • How to harness ADHD strengths in business, especially intuition, creativity, and rapid adaptability.
  • The power of mindset: reframing “failures”. 
  • The whiteboard system Shelby learned from her dad, breaking tasks into small steps and time-tagging them to combat time blindness and overwhelm.
  • Managing scattered ideas so you can build momentum without losing sight of bigger dreams.
  • Creating emotionally intelligent business communities for ADHD freelancers and shame-free support.
  • A powerful reframe for neurodivergent entrepreneurs: What if there’s nothing wrong with you and everything wrong with the systems you’ve been trying to fit into?

Links: 

LINKED IN: https://www.linkedin.com/in/shelbydenniscopywriter/

SHELBY DENNIS WEBSITE: https://www.freelancermindset.com/

FREELANCE WITHOUT FILTERS: https://www.skool.com/freelance-without-filters-4974/about?ref=30e789474b3e4f13b956b3c7a355866c

Send us a text

Thanks for listening.

JULIE: Welcome to Season 2 of ADHDifference. I'm your host, Julie Legg, ADHD advocate, author of The Missing Piece: A Woman's Guide to Understanding, Diagnosing, and Living with ADHD, and an unapologetic doer of many things. This season, we're turning up the volume with a global lineup of brilliant guests bringing their lived experiences, insights, research, strategies, and resources. And of course, along with a healthy dose of humour and humility. Whether you're neurodivergent yourself or just curious, there's something here for every curious brain. Let's dive in. Meet Shelby Dennis, a freelance copywriter turned ADHD friendly business coach who helps neurodivergent entrepreneurs build sustainable and profitable businesses that work with their brains, not against them. After 5 years of building her own successful copywriting career while navigating late diagnosed ADHD, she lives and works at the intersection of ADHD, entrepreneurship and storytelling. Well, good morning and welcome to the show, Shelby. Hello. [Thank you so much for having me. Wonderful to be here.] I'm so glad you are. Look, straight into the questions. You've gone from freelance copywriting to ADHD friendly business coaching, but before all of that, there was your own late diagnosis. Can you take us back to that moment and what prompted your ADHD assessment and what was your journey? 

SHELBY: Yes, absolutely. So, it was back in 2019 and I was working at a corporate job that was a little bit newer to me. I'd been in it for about 6 months or so and I really enjoyed it, but I was starting to see the same kind of problems and feedback cropping up that I had seen at honestly every job I had ever had before that. And I had worked a lot of different jobs, you know, hairdresser, running salons, different corporate things, office managers, just all up and down the ladder really. And so when I started to hear again, "Hey, you know, you're great at your job and your role, but you're not really staying in your lane. You have all these ideas for other people's departments and for other systems and it's just not what we hired you to do and so if you could just try to focus a little more on what we hired you for. Know that we have the rest under control. We'll take it from there," and that just... it really didn't sit right with me because my perspective has always been a rising tide lifts all boats. And so I started to think you know, I keep hearing this feedback maybe there is something I can learn about myself from this if nothing else. So started going into therapy just to kind of unpack whatever there even was to unpack. And within a few sessions, she told me, you know, I can't diagnose you myself, but I have a pretty strong suspicion that you have undiagnosed ADHD. And I have a psychiatrist I've love to send you to, to go through that process. And so I said, you know, let's find out what's going on here. Different neurodivergent things do run in my family, so who knows? And so we went through that, went through the assessments and all of the various paperwork. And the more that I read about it, the more I checked these boxes, I was like, "Oh my gosh, that's me. That's me. I've never felt so seen or acknowledged before. This is just a piece of paper, a form." And so we get to the end of it and he does all his stuff and of course it comes back that yes, very, very much checked all the boxes for ADHD. And learning how it manifests, especially in kind of men versus women. I started to find out it's really common for women especially to have this experience of being 'too much' at work and then finding out, oh, this is why because I'm neurodivergent. And so it really made everything make sense for me in a lot of ways. It really changed my self-narrative from I'm lazy or I'm undisciplined into, oh, my brain works differently and needs systems that the standard corporate workplace was never really setting out to create. 

JULIE: You said a few wonderful things. One was you weren't staying in your lane. I think that's a beautiful... a beautiful way to describe it. I completely relate to that. Why stay in the lane when there are so many options and you've got so much to contribute? Hairdressing and copywriting, they're very much an ADHD happy place, very creative spaces, yet I can see how you'd be drawn to the industry yet still wanting more in a way. Oh, wonderful. Wonderful. Talking about businesses, I'd love to know what traditional business advice often fails us ADHDers or entrepreneurs and the challenges that we wrestle and the strengths that we can also bring to the table. So, what I'd like to start off with is traditional business advice that doesn't work for us. 

SHELBY: Yes. Oh my gosh, I have a lot to say on this. We could do a whole thing just on this because, you know, after that diagnosis and everything, I was still just trying to kind of hang in there. The pandemic hit and everything was shut down and I realized, you know, there are a lot of signs telling me to go into business for myself. I've wanted this for a long time. Let's just jump in with both feet. And coming into that with a very new ADHD diagnosis and then all of the traditional business advice that gets heaped on to us as newbies, it was a lot to sort through. And so the things that I over time have really looked back on and thought, "Wow, that might work for some people, but absolutely not for an ADHD brain." The first thing is the idea that you just need to put in the time every day. I read so many articles, books, went to so many like coaching sessions and things where they said, you know, as long as you are just sitting there, you can really put in the time. Whether that's 8 to 5, 9 to 6, just like get started as early in the day as you can and just go for it, you're going to get some stuff done. You're going to really make progress a lot faster than you think. The problem with that is that assumes that you have a consistent executive function skill that we with ADHD don't really have. It's not really in our wheelhouse to sit down and say, "Okay, 8 a.m. I have this list of 10 things. I'm going to do them one by one." And that's just how it is. We are so driven by creativity and novelty and that dopamine rush that it's just, it just doesn't it... I found it more counterproductive. I found it so stifling to try to sit down at that same time. And when I instead leaned into I have an idea that is fueling me and I want to see what I can do with this. This evening tonight even was really, really freeing. So being able to put in the time when you feel that drive versus oh it's 9:00 a.m. I have to sit down I think is huge. So thank you. Thank you. And kind of related to that, very similar but different, is the idea that you have to wait to launch until you have every single detail figured out. You know, of course, you want to have some of the major pieces figured out, but generally speaking, we are so great with intuition and recognizing patterns before our conscious front of mind even notices it that if you've got an idea and you really feel in your bones that it's something to go for, I don't think you need to have every single thing figured out, especially when you consider how easy it is for us to get trapped in analysis paralysis. Like telling someone with ADHD, wait till you have everything figured out is like, that's the rest of my life. I could research whatever the topic is, right? And then the last one that really got me early on was the idea that you need to focus on one single niche or one single vertical when you're starting out. Again, really great advice for somebody who is neurotypical, brand new, doesn't really know where to start. But for us, we have the ability to see just like ripples and echoes of things across so many avenues. So, for example, when I started what I was doing, I took my salon experience, that was the chunkiest experience I had, and started writing for beauty and hair care brands that needed copy. But pretty much immediately, I was able to elevate that into writing for software companies that make like software and booking tools for salons, even though I'm not a techie. I have no idea how to code anything, but I was able to immediately get in kind of the mindset of that person and have this related but different set of niches that fulfilled me in different ways. And I think that's also huge for people with ADHD. 

JULIE: Definitely. And part of our strengths too is we're quite nimble. We're able to shift quite quickly in direction if we needed to. We're not necessarily stuck in our ways. And that can really work for us, can't we when we need to think quickly or act quickly or grab an opportunity while it's available. You're right, with this analysis paralysis, it can be such an anchor in a bad way to slow everything down. Yeah. Oh, that's some really great advice. Thank you very much. We've talked about some bad advice. What's some good advice leaning into ADHD strengths? 

SHELBY: Yeah. So, some of my favourite advice for leaning into ADHD strengths really comes down to mindset work more than anything. Like, at the end of the day, you have to really come at whatever advice you take on from a place of understanding that the systems created in most schools, most workplaces, most companies just were never designed with neurodivergent people in mind. And so if you try to think to yourself, oh, how can I take this system from a previous job I had and try to apply that to running my own business and you find yourself miserable, like that's not a failure, that's data. So I think that's probably the way I would phrase that is anytime you try something for yourself and you think, "Oh gosh, that didn't work out." Never think of that as there's something wrong with me. I did this wrong. I'm lazy. That's just data that you can use to create a system that does work for you because we're out here kind of pioneering stuff for ourselves and that's a beautiful thing as long as you can keep your mind there instead of in the zone of oh I need to fit in this mold. 

JULIE: Wonderful. Great advice. That's so true. So that's really piecing together our lived experiences and melding them together to become a super strength really of knowledge. Yeah. Very interesting. Right. Okay. Back to the question which was going to be about what are you really excited to be working on right now? 

SHELBY: Yes. What I'm really excited about right now is that in just the next like week or two, I'm going to be launching a school community for ADHD copywriters and ADHD freelancers. And I'm really excited about it because I frankly have not seen anything quite like this anywhere else. You know, the thing that I find with everybody that I coach is that it's never just about business. It's never just about getting more clients or growing your revenue or anything like that. We do what we do because we are who we are. We're passionate. We're quirky. We really love to niche down on things. And so I feel like when you own a business with ADHD, it cuts across everything. It cuts across like, oh, do I have time to do laundry and dinner? Like you succeed somewhere. It makes you feel more successful elsewhere. And so this community is going to be not just entirely business resources, but we want to have like live body doubling sessions where you pop onto Zoom and if you want to do laundry, great. You want to work on a proposal, that's fine, too, because it's all part of the same bigger picture for us. And I'm really excited about that. [Wonderful.] And then I was just going to say that for freelancers specifically, I'm just so passionate about helping them because I think so many of us with ADHD have had this experience of I just got to find that job that gets me. I just got to find that boss that's really going to respond to the way that I work. and that is out there, but for a lot of us, it makes a lot more sense and it's a lot more freeing to build our own thing and go forge that. 

JULIE: That's amazing. And so, you said your school will be sort of starting up in the next week or so. Can you tell us more about that if listeners are keen to tap in? 

SHELBY: Yeah, absolutely. So, I'm going to be launching it with a couple of like starter courses. I want to really be able to help the beginners, newbies, and then we'll kind of build out from there because that's of course when you need the most help. So, everything from how you decide what kind of services you're going to offer to what niches you want to start with to how to even put together a little portfolio, how to start reaching out to clients, just all of the questions that yes, you can go find, you know, any kit of templates for, but there's nothing out there that acknowledges all of the emotion that goes into that when you have ADHD. And so mine's very emotionally intelligent and geared towards keeping you out of the shame spirals, out of the second guessing, all of those really powerful things you get sucked into. 

JULIE: Wonderful. And I'll provide those links in the show notes for the episode. So we can go and check it all out. Shelby, writing and creativity, it seems to go hand in hand with a lot of ADHDers. Can you tell me more about your perspective on that creative process? 

SHELBY: Yeah, absolutely. And I agree. It's funny. The more writers I get to know, the more I find just how many of us also all have ADHD. So, it's like, oh, there's something to this for sure. What I love about it is that the thing with ADHD is that it allows us to see the forest and the trees at the same time. And I feel like, you know, that's honestly why I and so many other people with ADHD have struggled with traditional jobs because you see the trees, which is your job role, but you also see the forest, which is the overall success of the company. And again, they just they don't, they don't pay you for that. They don't want that info from you a lot of the time. But when you're writing for clients, you know, no matter what they come to you with in terms of writing, whether it's a single blog or an email sequence, it's really easy when you have ADHD to see that and kind of just zoom into the shoes of the target audience and think, okay, well, what else? What else would go with this? It really triggers your creativity. Like, okay, if we're doing an email sequence, what else might we need? What is missing here from the stage of the buyer's journey that we're in? And that's great because it adds a lot of fun for you as the writer and a lot of room to not stay in your lane and really just throw it all out there. And for the person you're working with, it gives them so much more value because now they don't have to go hire a different writer for every single one of these things. They can work with one person who really gets their brand, gets what they want to do, and can carry that across all these multiple different projects. And so even if you work with just a couple clients, you can do all these different things every day, it's never the same from one day to another. And that just makes my brain so happy. I love helping other people discover it, too, because there's no ceiling to it. Sky's the limit. Another nice thing with it, too, is that like rejection sensitivity, right, is really huge for a lot of us. And it can be so just defeating when you don't not even getting a no but not hearing back from someone. It's like, "Oh my gosh, what did I do wrong? What does that mean?" And the flip side of that though is that when you have a client who is really tuned in to what you're saying and really responsive, it's almost like really rejuvenating or restorative for me. You know, it's like now after so many years of doing this, whenever I don't hear back, whenever I do get a no, it doesn't really trigger that rejection sensitivity the same way because I've got these years of people saying, "We love the ideas. We love the overarching approach you bring to things." And, you know, I am all for work life balance, separating personal from work, but if you can find work that really fulfils you in that way, I think that's a great thing. 

JULIE: Absolutely. I think we all strive for that. Wonderful. Yeah. Thinking of strategies for ADHDers, particularly when running your own business, it takes both creativity and structure together. Is there a strategy or a tool that you use personally that helps you stay grounded as both a coach and entrepreneur, or one that you recommend to your clients? 

SHELBY: Yes, I do have a very specific strategy tool that I love that actually came from my dad. And my dad is also an ADHD business owner himself. So, it should be no surprise this works so well for me. But my dad has been a general contractor for his whole life for commercial construction. So, skyscrapers, gas stations, everything in between. And our den in our house growing up was the base of operations. And so, an entire wall was a whiteboard where we would map out every single job that was coming up. So it was the name, how much time it would take, anything special you needed for it. So you could come in and just look at any day or week and kind of know what you needed. Made it easy to shuffle things around too. And over the years as I got to work for him as an admin and things in his office, he taught me how he did this board because I without knowing I had ADHD then look at this and just say, "How do you know that you actually have enough time? How do you? How do you trust any of this is accurate?" and he taught me this system and it's exactly what I use today where you take a project for any client that comes in and you break it down into as many little steps as you can. So all the teeny tiny little pieces and then you tag each of those with how much time you think it's going to take. Even if it's 5 minutes, tag it all. Once you have it written out, add 10% to every single one of those items. Add it back together and then add another 10% to that grand total. And that's how you map something out. So, honestly, anytime I get a new project or I'm going to be putting a course together, any literally anything for my business, I'll make this list of every itty bitty step, add the time, and then I can start fitting it into my workday. So, I'll say, "Oh, I know that I'm not really a morning person myself, so this is going to slot into early afternoon, let's say." And then you can build everything else around that. I love this system especially because it accounts perfectly for time blindness. Like I'm still in my personal life not as good with this. I'm definitely the person that says, "Oh, I'll be there in 30." And then I don't think about all the other little details and you know an hour later I get there. This accounts for anything like that, including if you get kind of lacking momentum because you get bored with it and you have to find like a way to restart yourself or you just want to go do something midday. It gives you this freedom so you're not chained to your desk. You're not emotionally spiralling into, oh gosh, do I have enough time? And anytime another new request comes in or you have a new idea you want to work on, you can fit it right into your calendar. There's never a question. 

JULIE: Particularly when we're working for ourselves, we need to be realistic with our goals. And I love these chunks, these little steps, and allocating time is perfect. And then we can look upon our day or our calendar and go that's... I'm going to achieve something today and feel good about achieving things. Not the whole project. No, it's not finished. But all those elements to tick off. Great strategy. Definitely. Often with ADHD, we have so many ideas, so many options with the creativity overspilling and they're almost could be considered scattered ideas. How do we try and rein some of those in when there are almost too many options, too many possible copywriting lines? You know, how do we tame our scattered ideas and thoughts there? 

SHELBY: Yeah. The way that I do this for me is like I kind of do a little bit of mental visualization first to bring myself back to it because if you think about this scattered energy, you can think almost about like all these marbles scattered on the floor, right? Right? And it's like, well, I can take one step this direction or five steps that direction and where do I go? And so I try to think of it as putting it more all in a line or almost like a staircase. So if I've got a ton of ideas, I'll say, okay, what is the next small step I can take and then what's the next small step? And I don't mean that as in like breaking any idea down into bite-sized things, but if I've got, say, two niches that I'm really interested in and one is much closer to my realm of expertise and the other is a little bit farther out, I'm going to take the one that's the lower hanging fruit, that's the smaller step. Because the other nice thing about that is I just don't really subscribe to like hustle culture or rise and grind or any of that. Like the whole point is to build something that feels good that we can sustain. And so if you, for example, start with the closer, easier thing, get a little bit of income doing that, then you've got more breathing room and more runway for the next big thing. And so that's how I try to categorize when I've got millions of ideas. What's most accessible? What's the lowest hanging fruit? And then I'll climb up from there. I like that, too, because it means you never have to say goodbye or no to an idea. You're just moving it a little further out in the horizon, and that works a little bit better for my brain. 

JULIE: That's great. for someone who's newly navigating ADHD while trying to build a business or has tried and failed and anxious to start again, what would you like them to hear? 

SHELBY: Yeah, definitely. The biggest thing I want to center this around is that the most freeing thing anybody can do is to give yourself permission to stop trying to be neurotypical. The business advice that we're following, the systems that we've learned in, whether it's school or past workplaces weren't designed for our brains. And so, of course, it hasn't worked for us. It It's a pretty simple if then if you really think about it. A story that a therapist told me once when I was like having a podcast with her that I love is kind of sheds a light on all of this, which is that, you know, today, yes, having ADHD, having autism, being neurodivergent in any way is often seen by neurotypical people as a drawback or something that's less than ideal. But at the same time, these labels that we give all of these conditions are just the labels we give them right now. If you were to take any person on this planet with ADHD and pop them back into, you know, a time frame when people were hunting buffalo or bison and tribes, that person would be one of the most valuable people because they're so great with recognizing patterns, with addressing fight or flight, with really making in the- moment decisions that have to be correct. They can't be wrong. And so, it's easy to feel like maybe you don't belong or you're undisciplined, but it's just the framework that we live in. And the last way to kind of like phrase this is something that I like to ask people is what if there's really nothing wrong with you and everything is actually wrong with the systems you've been trying to force yourselves into. 

JULIE: Wonderful. Thank you so much, Shelby. That's great. [Yes, of course.] I appreciate you joining me today on the show. Thank you so much. [Oh, my pleasure. Thank you.]

Head Shot

Julie Legg

Host
Head Shot

Jel Legg

Co-host
Head Shot

Shelby Dennis

Guest