Episode 161: Navigating ADHD Entrepreneurship with Clarity and Purpose [featuring Corey Wilks]
Show Notes
In this episode, I talked with Dr. Corey Wilks, a licensed clinical psychologist and executive coach, about aligning life achievements with personal values and some of the unique challenges neurodivergent entrepreneurs face, particularly those with ADHD.
3 Key Takeaways:
- Align with Your Core Values: Corey emphasizes the importance of ensuring your life's work and business are aligned with your core values. This approach reduces regret and fosters genuine fulfillment. Remember the Stoic concept of "Memento Mori" – using the awareness of life's finitude to inspire living fully.
- Turn Someday into Today: Instead of procrastinating and waiting for the "right time," start acting on your aspirations now. We discussed the necessity of transforming "someday" goals into actions, integrating values-aligned decisions into both life and work.
- Leverage Procrastination Positively: Don't let perfectionism or analysis paralysis stop you. Reframe procrastination as a strength to generate pressure and meet deadlines efficiently. Use strategies like preselling to validate ideas and create accountability, ensuring you're working on projects with real market interest.
More about Corey:
Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach who helps the top entrepreneurs in the world clarify what matters, overcome limiting beliefs, and build a values-aligned life and business. His work explores the psychology of success and what gets in our way. He also shares these insights in his weekly newsletter, which you can check out at coreywilkspsyd.com.
- YouTube: youtube.com/@coreywilkspsyd
- LinkedIn: linkedin.com/in/coreywilkspsyd
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Transcript
PATRICK CASALE: Hey, everyone. Welcome back to another episode of the All Things Private Practice podcast. I'm your host, Patrick Casale. I'm joined today by Dr. Corey Wilks. He is a licensed clinical psychologist and executive coach who helps the top entrepreneurs in the world clarify what matters, overcome limiting beliefs, and build a values-aligned life and business.
His work explores the psychology of success and what gets in our way. And he shares these insights in his weekly newsletter, which you can check out at coreywilkspsyd.com which we will have in the show notes.
Corey, welcome on. You were just on Divergent Conversations, talking about neurodivergent entrepreneurship and creativity. And today, we are going to talk about ADHD entrepreneurialship and trying to figure out a way to keep things in check, especially, financially. So, thanks, and welcome to the show.
COREY WILKS: I'm excited to be here, man. Thanks for having me,
PATRICK CASALE: So, when I asked you before we started recording what do you want to talk about, you know, it's the same old song and dance that we do with a lot of people. And they're like, "Hey, I don't know. I can talk about this, this, this, this." And you were like, "What about, like, running a business and not ruining your life financially as an ADHD entrepreneur." So, why does that feel important and why does that feel meaningful?
COREY WILKS: Well, I think it's more so if we're talking about neurodivergence, specifically, around like ADHD, and entrepreneurship, and things, it's really easy if you're kind of wired that way to be really good at being creative and coming up with ideas. But a big part of entrepreneurship is actually executing on ideas. So, it's like, how do you balance creativity and execution, you know, thinking and doing? Those sorts of things. So, I thought that could be an interesting topic that your audience might enjoy.
PATRICK CASALE: Yeah, I love it. I mean, I think about that all the time for myself and all the, like, checks, and balances, and systems that I've had to create to rein myself or reel myself back in because what I've had the propensity to do, which I'm sure a lot of you listening who are ADHD can relate to is like flurry of creativity, and ideas, and hyper focus, and all of a sudden you have seven different projects that you're working on simultaneously. And what ends up happening so often is, like, none of them get created because you're kind of doing a little bit of this, a little bit of that, a little bit of this, and all of a sudden it's just too overwhelming.
And you, kind of, can beat the shit out of yourself mentally and emotionally, when it's like that narrative of, "I can never get something started, I can never get something finished. I'm so good at, like, just creating and then letting it go." Do you relate to that at all?
COREY WILKS: Oh, for sure. Like, you know, I think a lot of us just have, like, a graveyard of ideas and projects that, you know, we started to maybe build, and then, they just kind of died. So, we look back and say, "Oh, there are so many things that I could have done, I wanted to do, and I was excited to do at the time, but I just couldn't necessarily carry it, like, through the finish line."
PATRICK CASALE: Right, yeah, absolutely. I've been in that boat so many times, and I've come up with a system for myself. You know, like as an autistic ADHDer, you sometimes get the best of both worlds, although, it can often feel like the worst of both worlds simultaneously. But my autistic parts really do a good job of checking my ADHD parts where it's like, let's take these chaotic, creative ideas, and let's structure them. Let's, like, outline them, pick them apart, strategize the next steps, like, create some accountability measures. I love a good list. So, like, if I can put them on the list and cross them off the list, then it works really well for my brain.
What kinds of things do you do to kind of balance your creativity and keep it in check?
COREY WILKS: So, a couple things. I think, one that I've been experimenting with more lately is collaborating with other people so that you have built-in accountability.
PATRICK CASALE: Yeah.
COREY WILKS: But I think, especially, with entrepreneurship, you know, you are your own boss for better or worse. And I personally don't like being micromanaged. It's one of the reasons I'm an awful employee because I would rather just, you know, tell me what needs done and then let me do it my way, sort of a thing.
PATRICK CASALE: For sure.
COREY WILKS: And what I've found is, when I've tried a lot of the typical productivity, you know, hacks, and strategies, and tips or whatever, I just feel like I'm micromanaging myself, so I just end up getting pissed off and resentful at myself for micromanaging myself, right?
So, a lot of those typical strategies don't really work for me personally. But I think that collaborating with the right people is a huge unlock because you get that accountability without feeling micromanaged. So, that's been something interesting I've been playing with lately.
And also, just collaborating is a really good way to kind of pull resources and strengths. So, then that way, you know, maybe I'm good at this thing, but I suck at this other critical piece of business, for example. Well, maybe you have complimentary skill sets. So, together, we can build something better than maybe we could have on our own, or we just end up actually building the thing rather than both of us separately just thinking about building the thing, right?
PATRICK CASALE: Right.
COREY WILKS: That's been a fun thing to experiment with lately.
Another thing that I historically do, and we could talk about, like, building a values-aligned life and business at some point, if you want because I do a lot around values work and I embody that in my own life and business as well. Of like, if you do the things that are intrinsically rewarding and motivating, it's really helpful because you're not losing motivation, because you're doing it purely out of the joy of doing the thing.
But another piece that has really helped me is this whole idea of kind of thinking in projects. I forget who it was, but they had this whole idea around, like, business and software of 12 projects in 12 months, or 12 startups in 12 months. And the idea behind it was, how can you basically work in 30-day sprints, so that at the end of that 30 days you have a self-sustaining thing, whether that is a book, an eBook, a course, a software, or something else.
So then, at the end of the year, you can look back and say, "Okay, well, of these 12 things, which is gaining the most traction that maybe I can consider doubling down on that thing." Right? That way, you know, the whole adage of, like, don't put all your eggs in one basket, that is one route that works for some people, right?
There's a big debate about should you diversify early like that as, sort of, like, a shots on goal, sort of approach of, well, let me just, you know, throw a bunch of things out there and see which gains traction, and then let me double down on that rather than risk putting all of my time, energy, and attention into something that maybe, you know, was never going to work out in the first place. But then, other people are like, no, no, you should solely focus on one thing so that you give it the maximum, you know, chance to succeed. I've personally seen both work for different people for different reasons, right?
But I think, especially, you know, if you're wired a little differently, it can be very helpful to try that. Daniel Vasallo calls it a small bets approach. Like, how can you just place multiple small bets? You know, let me build a thing for two weeks or 30 days, and then, move on to something else.
I think that approach can be really helpful if you are naturally curious, and creative, and you struggle to stick with things for the long term., initially. I think that allows you to basically work in sprints. This is the one thing I'm going to, you know, hyper focus on for a couple days, or weeks, or maybe a month. And then, I'm giving myself permission to move to the next thing. Then I can look back and see what gained traction. That has been one strategy I've used, personally, in my business.
PATRICK CASALE: I love that because, especially, if we're talking about, you know, ADHDers, right? Where we need the new, we need the stimulation, we need something that feels exciting.
If I look at a to do list of like 10 projects, the odds of me being able to figure out which one really excites me the most in the moment is pretty slim. Maybe I'll work on the low-hanging fruit. Maybe I'll work on the easiest path and least resistance. Maybe I'll work on something that's already been created and improve it. But like, if I have my book, my coaching program, this course, this thing, I like the idea of doing that because it allows you to interest hop.
And Megan and I were talking about interest-based nervous systems a couple of weeks ago. It allows you to pursue that and really soothe your nervous system, which is driven by interest, to be able to help you feel more focused, feel more content, feel more excited. And then, you don't have that pressure of like, "But I've got to do this thing by this date because this is on my to-do list." It's like, "Let me follow the passion, let me follow the creativity." And then, being able to circle back and double down if it's still bringing you joy, if it's still lighting you up, if it is becoming something that's worth pursuing even more. I like that instead of feeling like you have to do something.
I know for myself, if I'm like, "I've got to do these things." The walls start to feel like they're closing in. And I don't really operate well like that. That's why I also feel like I'm not employable either. So, that really resonated with me.
COREY WILKS: Well, it's also like the idea of, well, there are multiple things I want to do, so I have to choose. And that choosing can be almost paralyzed, right? Like, analysis paralysis. Like, well, you know, maybe they're all viable, but I just don't know which one that I can pick because I've made the false assumption that by choosing one, I have chosen to not choose the others, right?
This approach is much more approachable for people because you're not choosing which to do, you're choosing which to do first. Because you're giving yourself permission of like, oh, I can do all of these things. I just can't do them all at once. So, of the five things I want to do next, let me just pick the one I want to do first, then I'll do the next one, then the next one. That I think is much more helpful and freeing for people who struggle with this specific issue.
PATRICK CASALE: Oh, for sure because if you're looking at those five or six projects, and your mentality is, "Well, if I choose one the other five won't get done." The reality is, like, probably none of them will get done. But if you are picking it apart this way, like, okay, I'm going to give myself a month to work through this thing, check it off the list, move on to the next one, much more likely that you're going to be able to sustain focus, creativity, flow state, etc. And it also doesn't mean that you can't add more things to the list, right? Like, as you're in that flow state, as you're in that creative process, you may come up with other ideas that then go into that list for like month three, month six, month 10. So, I really like that a lot.
I'm just thinking about other ADHD nuances in terms of small business ownership, and for me, I'm a big procrastinator. Like, I struggle with inertia, I struggle to get started with something. But if it's the last minute and there's a lot of pressure, it's going to get done, and it's usually going to get done well.
I used to really beat myself up for that, and like, "You can never get started, you're always waiting to the last minute, you're procrastinating." But now I almost look at it as like a strength, and I try to reframe it and flip it around to say, like, this is really what works for you, and that urgency, the need for something to get done, the pressure. I mean, that's where I really shine. Do you have any thoughts around any of that?
COREY WILKS: Yeah, well, and I think that's another reason why this approach can work for people because you're setting deadlines and shortening your timeline, right? So, then you're like, "Oh shit. Like, this month, this is what I'm doing, and I've got 14 days left. I've got seven days left." Right?
That is a decent way to artificially create deadlines for yourself, which, again, as an entrepreneur, it was really easy to just fuck off and not do anything for, you know, a way too long a period of time because you don't have to answer anybody. But if you're like, "Hey, by the end of the month, you know, I'm going to have this thing out, and I've told people about it." Right?
PATRICK CASALE: Yeah.
COREY WILKS: One nuance with this, I will add, that I really, really enjoy is pre-selling, right? And this is more so with courses, or, you know, digital courses, or, you know, live courses, things like this. It's really, really helpful because, one, pre-selling really helps de-risk your next project because you don't have to sink a lot of time or money into something that maybe people don't want, right?
So, I did this a couple months ago. I pre-sold something. And, you know, so basic version of pre-selling that I use is I will throw up an MVP offer. I will say, "Hey, if you want this at the founder's rate click here."
And in my head, I have a validation number. That may be 10, that may be 100, it depends on the project and the price, right? And that validation number is my way of saying, if I get this many people minimum who sign up, then I will build the thing, right? Like, this isn't field of dreams, if you build it, they will come. No, no, no. If they come, I will build it, right?
So, if I hit validation, cool, I build. If I don't hit validation, then I refund whoever, you know, did, you know, show interest and purchased? And then, usually, either I'll come up with something, or I'll talk to them, you know, get some more research. So, that way there's no risk, right? Because, like, I think a lot of us have gotten into the trap, you know, especially, early on in our entrepreneurial journey of putting all this time, money, attention into building some shit that just nobody wants either because it didn't address a real pain point, we didn't position it right, it didn't actually address the thing we thought it addressed. There are 101 reasons why something doesn't work. And you never typically learned why it didn't work.
PATRICK CASALE: Right.
COREY WILKS: Because people aren't just like, "Hey, let me reach out to you, you know, manually, and tell you why I didn't buy your thing." That just rarely happens, right? But pre-selling really helps you de-risk your business and your projects, right?
But the other thing that it does is, if you hit validation, then you're like, "Okay, fuck." Like, I had two weeks to deliver this because I told them that, you know, it's a two-week pre-sale, and then, it'll launch two weeks after that. So, I basically give myself a month from start to finish.
Well, now real people have given you real money to build the thing. So, that is a really great deadline to really motivate you. Like, okay, shit. Like, this is my only focus for the next two weeks, is delivering this thing that people had given me their hard-earned money to give them.
PATRICK CASALE: Yeah, I love that. Actually, I'm going to start implementing that because you're so right. Because it takes away a lot of the pressure, a lot of the risk, and then, it creates a lot of the accountability, and the urgency that we really so desperately need.
And I do a lot of pre-selling too, or like, a little, like, market research. Like, when I launched my first retreat back in 2022 I just remember posting on my Facebook like, "If I hosted a retreat in Ireland who would come?" And all of a sudden 75 people were like, "Yeah, I'm in. Just tell me when."
There's a big difference, though, between I'm in, tell me when, and purchasing, right? So, there's, like, a big in-between. And that's where all the pressure comes in. But I knew as soon as I put it out to the world and people were interested, that I was going to pursue it. Had I not done that, I would have just sat on it, and I would have convinced myself I don't know how to do this. You've never done it before. No one's going to buy it. All the narratives that happen.
So, by getting that response and testing the waters a little bit, seeing that there was interest strong enough to, like, warrant pursuing the risk, I just dove in, very ADHD style of like, I'm just going to book a venue, find dates, like, figure out all the steps, and build the plane as I fly it, instead of having, like, the polished product ready to go and offer immediately.
COREY WILKS: For sure. That and like, it helps you avoid scope creep. Because, again, this is largely around, you know, coaching-related things, right? Like, either doing like a digital course or like a cohort-based course, like a live course, live event where there's programming and any kind of curriculum, right? It's so easy, although, the same is true for software, right? Like, scope creep or content creep is a huge issue, right?
When you are just ideating, or, like, theory crafting, when you're just thinking about doing the thing, it's really easy to try to make it an all-encompassing, ultimate thing to whatever, right? And you, eventually, get to the point where you're just, like, this extra thing that I could add no longer is in any way related to the central reason somebody would buy this. But I'm trying to make it everything to everyone. But if you pre-sale, you're like, "Fuck, what can I put in this shit in the next two weeks?" Right?
Like, and that's, again, we can go into, you know, my specific way of how I do pre-selling and things. But the biggest piece that I've learned is, you know, you can just, basically, ask people what they want. Like, give a soft outline of what you're planning to put in it. But really, just ask people what they want, and then, just build that, right?
Like, when I pre-sell, when you buy I send an onboarding survey. I don't send it to people who haven't bought, right? Like, because I don't give a shit what you want if you haven't given me money. Like, right? Like, when this is a business thing, I'm not just going to, like, randomly ask my LinkedIn following or Twitter like, "Hey, what do you want?" Like, I'm going to build this thing, fill out the survey, please. It's like, these are people who have voted with their wallets. They're just voting with their maths.
And plenty of people will tell you, "Oh, that's a great idea." But won't pay for it. If people won't pay for it, it's not a great idea, right? So, I only ask this question to people who've actually purchased or, you know, pre-bought the thing because their votes are the ones that actually matter because they're paying customers, right? But then I'm like, what do you want? And within reason, whatever the fuck they said they wanted I just put that in the course.
So, anytime I'm like, "Oh, I would kind of like to put this in the course." It's like, "Well, dude, did anybody ask for that in the onboarding survey?" No, then don't, not yet, not for the first version, the MVP version of this thing that you're launching, don't put it in. If you want to [INDISCERNIBLE 00:21:05] it up and like, you know, redo it for V2, cool, maybe then you can add it in. If throughout the course people will give you feedback, "Hey, we really wish this would have been included." Oh, I'll put that in V2. But V1 is just like, I got two weeks to build this shit. Let me do it based on what I thought it needed, but more specifically, what other people have told me they wanted, that really helps you minimize any kind of scope creep.
PATRICK CASALE: Yeah, yeah. It's a good way to beta test, too, and then, to, like, take that feedback, pivot, evolve, adapt, implement, and do away with some of the stuff that you thought was a great idea at the time that nobody ended up really appreciating or taking advantage of.
And we can spend so much of our energy and time focusing on the stuff that we think other people are going to want, when in reality, like you said, if you haven't done that polling or collected that feedback, we're kind of just flying solo. And it doesn't really always work out in terms of like group offers, coaching programs, things like that, if you're really just catering to like what do I think that we need without taking that outside alternative perspective.
COREY WILKS: For sure.
PATRICK CASALE: So, last week, when you were on Divergent Conversations we talked about like values-aligned business. I think that's important here because for ADHDers, for all entrepreneurs, but especially, neurodivergent entrepreneurs, I think the why is really powerful. Like, the why matters.
And entrepreneurship can be challenging, and it can be rocky, and it can be a roller coaster. And there can be days where you're like, "I'm going to go back to bartending." Like I said many times back in the day. However, my value has always been autonomy and freedom. I want the autonomy to make my own choices, to make my own schedule. I want the freedom to work from wherever, whenever. Those two things are non-negotiable for me. So, I know if I went back to a 9:00 to 5:00, I do not have the propensity or the capacity to have those values intertwined into my career and my life anymore. So, tell me about yours and why it's so important to work from that, like, values-based system.
COREY WILKS: Yeah, so I focus on both of my own life and when I coach entrepreneurs and things, typically, start with trying to clarify your core value. If you can only get to, like, your top two or three values, that's fine. Sometimes people do struggle to get to like a single value. But for me, I really focus on a core value. Because, sometimes, if you have multiple values they can conflict in different situations and that can cause confusion versus if you say this is my singular, like, core value of what a life well lived must be aligned with, whatever that is for me, right? Mine is also freedom. I would argue that freedom and autonomy are largely, pretty much synonymous, right? For the purposes of, you know, viability, right?
And for me, I always ask myself anytime, you know, I get an opportunity that comes my way, or I think about a new idea, or a new project, or I'm at a fork in the road, I ask myself, does this get me one step closer to or one step further away from a life aligned with my core value, which for me is freedom?
That is singularly one of the most simple and effective clarifying exercises you can do because so often, especially, you know, with what we were talking about today, is like it's so easy to just be drowning in opportunities, or ideas, or possible things you could do. But it's like, okay, most things won't actually move you closer to a life aligned with your core value. It's a distraction.
And that's one of the reasons why you'll see a lot of people who maybe they achieve success on paper, or, you know, financial success, but they're absolutely fucking miserable because the things that they're doing, that they've dedicated their lives to doing didn't resonate with them, weren't aligned with their values. So then, despite this on-paper success, they kind of hate their life and their reality because they didn't have necessarily this question as a filter, right?
So, that's been super, super helpful for me because, like, dude, you know, I'm a big memento mori fan, right? Memento mori comes from stoicism, and it basically means remember death or remember you will die. It isn't meant to be like depressing so much as a motivator to use your mortality as a motivator to live fully, right?
So, like, my whole, like, right tattoo sleeve is dedicated to memento mori, you know, for people watching. Like, I've got the skull, the ravens over here. I'm a huge fan of this because, like, it's real. Like, you're going to fucking die one day, right? Like, that is a non-negotiable. Like, it's just going to happen.
PATRICK CASALE: Yep.
COREY WILKS: Rather than living your life in denial of that, and coasting through life, and living for someday, right? That's the biggest thing I hear from people is like, "Well, someday I'll do this. Someday I'll travel. Someday I'll build a business. Someday I'll be true to myself."
And it's like, okay, one day you're going to be out of some days, right? How can you make someday today? Like, that's the central thing that I work with a lot of my coaching clients on, is, how can you turn someday into today by building a values-aligned life and business, so that you don't get to your deathbed and look back on your life full of fucking regret, right? Like, how can you be fulfilled today? How can you reach your potential today? How can you self-actualize today? That's all of like, both my coaching and my entire business with the courses I offer, with my writing, my newsletter, my videos, and shit, all of that is centered around that concept.
PATRICK CASALE: Yeah, yeah. I love that because that's so true, right? Like, life is so short. And I hear that too from so many people. When I retire, I'm going to go travel. When I retire, I'm going to work on this. When I am able to step away, I'm going to do this thing. I just think we let so much life pass us by, and then, ultimately, we don't know what ends up happening or how long we end up making it for. So, I'd rather have a life that I don't regret at the end of the day and feel like I, at least, swung for the fences, so to speak, and went for it, and took the risk, took the leap.
I've kind of adopted the motto, doubt yourself, do it anyway, and try to incorporate that into everything I do. Because self-doubt, impostor syndrome, perfectionism are so rampant in our industry and in general. And they're so preventative from us pursuing our goals, or our dreams, or even trying to see if we can create something worthwhile. And I'd rather just fall on my face, and flop, and try again opposed to just, like, sitting on the idea or assuming it's better suited for somebody else.
COREY WILKS: Great.
PATRICK CASALE: So, we're getting ready to wrap up. But really awesome conversation, good tips, good strategies, some that I'm probably going to start implementing myself, like the 12 ideas in 12 months idea. I really like that because I have about 12 that I'm sitting on at the moment.
Any other last-second or last-minute advice for people listening, or things that you feel are really valuable to offer to them right now?
COREY WILKS: I mean, my big thing is like, you know, we talk about resources and, you know, assets and things like your time, your money, your attention, your whatever. But the reality is, the most precious resource you have is your life, right? Like, your life units, right? It isn't that it took three months for you to do something, it's three months of your life. It isn't time, it is life, right?
And I remember when I was in grad school, I had a professor, and she talked about the true cost of things. And I've since turned this into an article called The True Cost of Things. But, if you really want a pair of, like, Air Jordans, right? Like, I'm dating myself, I don't even know if they're still popular or not, but if you want, let's just say a pair of Air Jordans is $200. If you have a job where you make $10 an hour, those shoes don't cost $200. They cost 20 hours of your life. When you think of things like that, it really reframes the value of things and what you are willing to spend to pay for them, right? And it isn't just like material things like shoes or some shit. It's also like, okay, of all the things I could build, what are the things that are worth the life units I'm going to have to invest into actually fucking building?
PATRICK CASALE: Yeah.
COREY WILKS: And that for me, again, and it's a memento mori kind of a thing. But it's really clarifying. It really helps you prioritize because you can't do everything you want to do necessarily, right? You have a finite amount of, you know, life, basically. So, really learning to see what are the things that are most worthwhile to do, to build. That is sort of my parting words for that.
PATRICK CASALE: That's wonderful, that's deep and is powerful. So, that's the perfect ending on this episode.
Corey, I just want to thank you for coming on, thank you for coming on Divergent Conversations last week. And tell the audience where they can find you.
COREY WILKS: Yeah, coreywilkspsyd.com. I am Corey Wilks everywhere, Twitter, LinkedIn, YouTube. If you want coaching, feel free to reach out. Otherwise, I have a newsletter. You can check that on my website as well.
PATRICK CASALE: Cool, and we will have all that in the show notes, including the links, so that you have easy access to all of Corey's information. Thanks again, Corey, for making the time.
COREY WILKS: Thanks, [INDISCERNIBLE 00:30:58] man. Down to come back anytime.
PATRICK CASALE: Awesome. And to everyone listening to All Things Private Practice, I almost said Divergent Conversations, new episodes are out every single Saturday on all major podcast platforms and YouTube. Check out our 2025 retreats and summits in Spain, Scotland, Greece. Coming up in 2025 lots of summits, lots of events, lots of CEU opportunities, and training, and connection opportunities as well. Doubt yourself, do it anyway. And we'll see you next week.
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