Human Design, Uncertainty, and Strategic Evolution with Katherine Danesi

What does it take to lead a business through seasons of change—and still feel like yourself inside of it?

In this episode of Here’s What I Learned, Katherine Danesi joins me for a candid conversation on navigating uncertainty, evolving your offers, and creating a business that honors your actual life. From her days as a Fortune 500 exec to startup COO to systems-driven coach, Katherine has learned the value of doing business her way—and now helps others do the same.

We explore how human design, agency, and pricing all play into the shift from freelancer to CEO. And why learning to trust yourself is often the hardest—and most necessary—part of entrepreneurship.

If you're ready to stop white-knuckling your business and start building with clarity, this episode is your permission slip.

Topics Covered:

• Relearning how to live and lead through uncertainty (5:02)
• Why surrendering control can actually give you more agency (7:42)
• How human design shapes Katherine’s coaching style and boundaries (9:07)
• Rebuilding your business after stepping away or burning out (18:20)
• Why creative founders struggle with business development—and how to simplify it (21:43)
• Pricing resistance, rebranding delays, and what actually trips people up (23:52)

About Katherine Danesi:

 Katherine is a coach and strategist for creative service providers who are ready to structure their businesses for long-term growth. With a background in corporate and startup leadership, she brings practical systems and powerful perspective to every client relationship.

You can find Katherine at:

Website: katherinedanesi.com

Instagram: @katherinedanesi

Newsletter: Business/Women with Katherine Danesi

What next?

• Follow Here's What I Learned on your favorite podcast player
• Leave a review so the podcast is seen by more people like you
• Share this episode with a friend

Say hi!

• Follow me on Instagram at @jackihayes_obm
• Tell me what you loved about the episode at jackihayes.co/contact

Credits:

Intro and Outro Music: Atomic by Alex-Productions |https://onsound.eu/

Music promoted byhttps://www.free-stock-music.com

Creative Commons / Attribution 3.0 Unported License (CC BY 3.0)

https://creativecommons.org/licenses/by/3.0/deed.en_US

Thinking about starting a podcast—but not sure where to begin?

At Podfox Media, I help business owners launch podcasts that reflect their voice, values, and goals. We’re offer a free 90-minute strategy session to help you clarify your concept, define your audience, and map out your next steps—with no pressure and plenty of space for your questions.

Visit launchmypodcast.com.

Transcript

SPEAKERS

Katherine Danesi, Jacki Hayes

Jacki Hayes  00:06

Hey there. Welcome to Here's What I Learned. I'm Jacki Hayes, a system strategist, unapologetic smutty romancy lover, Dungeons and Dragons geek, and your no-BS guide to building a business that works for you. This is the place where we swap stories, share lessons, and get real about the highs and lows of creating a life and business that actually feels good. No cookie cutter advice here, just honest conversations about what's working what's not, and how to rewrite the rules to fit your version of success. So grab your favorite beverage, get comfy, and let's dive in. 

Jacki Hayes  00:41

Welcome to yet another episode of Here's What I Learned today. I have Katherine Danesi. She is a former fortune 500 executive and startup veteran, and she's turned to coaching and strategy, helping ambitious creatives put the structure and strategy in place to have a thriving, consistently profitable business. Katherine, welcome. How are you doing today?

Katherine Danesi  01:09

First of all, I am so happy to be here. Thank you, Jacki, for having me, and I'm doing great today. We're finally getting somewhere in New York, which is where I am. 

Jacki Hayes  01:18

We are too here in Iowa, and I love it. Unfortunately, it's too short. It needs to be longer.

Katherine Danesi  01:24

Agreed, but thank you. How are you doing?

Jacki Hayes  01:26

I am great. I'm just happy to get a chance to talk with you. We've had coffee chats before, but this is going to be another opportunity for us to connect. And I'm going to ask you the question I ask all my guests, which is, what is something that you have been learning about lately?

Katherine Danesi  01:41

So I have been learning, and this is personal and business, or living, living life and business, and it's about dealing with uncertainty and living into uncertainty and the unknown. And I've been it's something I've struggled with, frankly, so and sort of surrendering and letting go of control and feeling over responsible for all of the things. And I think I only realized how much I've been thinking about this when I read my newsletter. I do a weekly newsletter, typically goes out on Wednesday this week, it was Thursday the and the title this week was how to navigate uncertainty. And when I was finishing it up yesterday, I realized, Oh, I actually wrote, like, in a similar way, I took a different lens on it, but about a month ago that there's no guaranteed outcome, so clearly it's something that's been on my mind, and I think on a lot of people's minds right now, with AI with so many things changing so quickly, and how do we learn to live in that in a way that doesn't feel, doesn't induce fear on a constant basis? And how can we work with it in a way that, if it doesn't empower us, at least we feel we have agency and our choices. So that's something that I've been working with a fair bit and learning about and leaning into, and then on a fun fact, I've been studying Italian off and on for 10 years, so I am recommitting to 15 minutes a day of working on my Italian. 

Jacki Hayes  03:20

That's right, excellent. I have a collaborator that I work with who is literally in the process of packing up and moving to Italy right now.

Katherine Danesi  03:28

Well, wow, oh, wow. Good activity with her. We will do an introduction. 

Jacki Hayes  03:32

So, there's a lot of people in my sphere right now learning Italian, so I should maybe give it a try myself. I'm one of those people with Duolingo. I think I have three different four, four different languages that I've started. And I'm just like, I have my brother who lives in Denmark, so I'm learning that in Danish. And then I went and took French in high school. So I'm like, Oh, maybe I should brush up on that. And I want to go to Italy for a long, extended vacation. So yeah, it's like, pick one. Jacki, pick one. 

Katherine Danesi  04:03

It helps to pick one for sure. But I love your reasons for learning the languages.

Jacki Hayes  04:08

there's reasons not just random, even if it feels like it. Sometimes. I love what you said about the moments when we're in uncertainty and still being able to find where we have agency. Because I think for me, a lot of times it's that not feeling like I have any control of the situation at all, whether that's the political sphere, whether that's just certain things in my family or in home, but finding those little things where you do have agency can make a huge difference,

Katherine Danesi  04:39

right? And I think that leads me to what's in your control, truly, right? So things like how you respond, you're like, is within your control. If it's in business, delivering, working on marketing your business, working to bring in new clients, to. Bring excellent work. The response to all of that is outside of your control, right? So I think that's a really great point, and it's something to come back to, I think often and sort of ground into when things are feeling like they're a little going a little wonky or sideways.

Jacki Hayes  05:21

The other question I ask all my guests is, what does it mean to you when I say doing business your way?

Katherine Danesi  05:27

Yeah, I know what I love about this question because I think it's such an important thing to do. So I think there's sort of three ways for me that comes into play. And the first is, and it's a phrase I've heard a lot, I think via podcast I listen to, which I'd love to give proper attribution, but, oh yeah, I think it's Lindsay Mac and it's anyway she does Terrell so little woo, woo. But the idea of keeping your eyes on your own paper, right? So I can know what's going on in the world and what, what's the latest tool? What's the latest way somebody's packaging their offerings, I can try new things that I choose to do. I can track what's working and what's not working in my business, and then have the courage to either stick with it because it is working, or if it's not working, or even if it's working, for other people to say no and I tried it. I gave it a good shot and shifted gears. Does that resonate for you? 

Jacki Hayes

Yeah, yeah. That definitely does, yeah. 

Katherine Danesi

And then the second is leaning into me specifically and I encourage this for all of my clients, right? So lean into your my own experience and expertise to provide strategy and coaching services for my clients right in a way that leverages all of that and aligns with how I work best, and I approach coaching and really strategy is where I lead. I'm super action oriented with my clients. I'm all up in their business. We create a plan together, we come up with concrete solutions, and then we implement those solutions. And then I coach my clients in order to help them, if need be, to get out of their own way, and then actually execute on the plan, because as we move through it, there's going to be resistance points right that come up so leaning into what I know from all of the personal work I've been doing for myself to better show up in my business and in my life, and then bringing that to coach my clients to deliver on this strategy. And that's not how every coach works. And everybody has their own way. And then the third way that I think is sort of doing business. My way is, and I learned about this a few years ago, and I can't remember if we discussed it or not, so you'll have to tell me. But honoring my human design, so I'm a six, three emotional generator. And there's in my design, like with everybody's, there's certain gifts and whatnot. Being a generator, which is part of this, back to tying it back to uncertainty, is learning to wait, to respond to things not necessarily always initiating, and that's taken a lot of time, but when I lean into it, I've learned over the last few years that things are smoother, I'm less stressed, and my business is better. So that's what it means to me to do business my way.

Jacki Hayes  08:24

You gave me the first one, and I was thinking about something I was reading earlier today, and then you went on to the third one, and I was like, That's ironic, because I was I'm doing a deep dive into human design, because I do apply it with my clients, but I'm trying to create more resources for them when it comes to that. And I'm a manifesting generator, and one of the things that we are supposed to do is, if we get that initial Uh huh, put our toes in and try it and then wait to see how we feel after we've tried it, because we're very good at being like, yep, Nope, that didn't work, and walk away. But we need to have that try it first before we make the decision. Unlike a generator, if you go ahead and you put your toe in, you may just be inclined to be like, Well, I'm here now. I'm just gonna keep going.

Katherine Danesi  09:10

What exactly and with, I think, with how I'm supposed to respond to things, I for myself. I've gotta ride an emotional wave so I might hear something. I've seen myself do this, and I'm like, oh my god yes, Sign me up. I am all in, like, right now we're in a conversation, and then, like, tomorrow, I don't feel so great about it, so I have to ride the wave. So I have to, not necessarily, to commit to things immediately, to say, hey, this sounds really interesting. I need a couple of days to think it over, right? So that idea, and I love that you're creating tools for your clients. I have not gone that far, but where my clients have their design already or are inclined to get their design, it's helpful to me, because then I understand what's going on. And at a very No, I wouldn't say surface. I mean, I. Do read a lot on it, but I can understand what's happening, right? Because I have a client who's a manifesting generator, and her partner is a projector, so it's seeing the dynamic play out. And when my client and I didn't understand this, it was fascinating, the manifesting generator, she's like, Yeah, and I want to do this in the business, and this in the business and I was like, oh, but this isn't all going to be in one business. But then I understand her desire to master the side. Now making sourdough bread, okay? Like, totally get it, and learn to crochet, and do all of these things, right? So I don't know. I think the better that we can have an understanding of who our clients are, we're able to help them from that coaching perspective in a much better way. 

Jacki Hayes  10:47

What I like to try and help my clients do is understand their design, and then, because I focus on creating strategies for the operations of their business, specifically like how they work with their clients, I if they happen to know their clients. Human Design, it's about setting up a system that works for you because you're the service provider, but also, like, how can you adjust certain things in your business to meet the needs of your clients? So if you have a client who's a projector, you may tweak this thing a little bit versus a Manifestor. You don't have to completely change it, but what little tiny thing might you do? For instance, if you or if you're talking to somebody with emotional authority, you may know during the sales call that they're not going to answer, give you their best answer, right? Then you may say, I'm going to check with you in like 24 to 48 hours, where, if it's a manifester, they're going, they're going to give you the answer, and they're going to go with it, right? 

Katherine Danesi 11:44

Yeah, and initiate No. I think that's brilliant. I love that. That's fantastic. 

Jacki Hayes  11:51

Tell me more about how you ended up in business for yourself.

11:56

So I've been in business with myself for about 12 and a half years now. So it's been a minute. I had worked at a fortune 500 company in the technology space for a number for, like, over a decade, and I left them and then, which then initiated a series of startups that I worked at. So the first one was out in San Francisco, and a bunch of friends were going to it, and I'm like, Hey, I'm in a little detour after that got sold to London. I lived in London for a year and went and did a master's degree, and then I moved to New York and ended up in the startup world here in New York, rather than San Francisco. And when the last startup that I worked at I was the COO. So we have that, we share that operational event, Jacki, and when we couldn't raise funding, we had tried. The ideas were actually great. They exist today, just done by other people. But when we couldn't raise the money, our angel investor said, Okay, well, I'm out. So I was sweeping the floors and selling everything off and closing the the office up and the boutique PR firm we had used in New York to help us with events in particular, for one before we pivot one aspect of the business, she wanted to redo her business, literally, like take it down to the studs, everything about it, who she was servicing, look and feel, pricing, how she was working. What's her? What is her team all of it. So she hired me to do that. She was my very first client, and my business just slowly built from there and via word of mouth and referral and really working with either solopreneurs or really small businesses to help them grow and expand and look holistically at their businesses, and so yes, I've been doing it since then. I did a bit of a pivot with COVID, as a lot of people did in that I had typically worked almost as part of my clients teams, sometimes actually taking on roles within the company and delivering the services or whatnot, one degree or another, and I realized that way working wasn't really fulfilling anymore. So I made a shift, and wrestling coach sort of moved to be a coach versus I used to call myself a consultant, and moved more into this space. So it took me to be honest with you, like, a good 18 months to two years to fully get landed in the way I'm operating now. 

Jacki Hayes  14:23

So when folks come to you, business owners come to you, what are some of the your favorite scenarios that you love helping people with? 

Katherine Danesi 14:31

Sure that's great. So I think there's really two right now that I see common themes running through where I know I can help them, and I really enjoy the work. So it's it's two ways, and one is, I working with owners of creative businesses. So pure firm branding, digital marketing, I've got a video, short form video production partnership. I'm working with all of them, and they're actually really good at what they do, and they have had success. And now they have been doing everything themselves, and they want to grow, and they just but nothing's been formalized. They don't know often, there's no business dev process and there's no how are we? Our branding might need to be redone, and we, they just don't know what to do. So I partner with them. We look at the business holistically, and we come up with a plan that we're going to execute. Usually it's over at least six months. Typically it goes on longer, but six months is sort of a minimum engagement with me, and we start executing across this plan, doing the right things in the right order, so that we're not repeating and going back and doing something that we didn't need to do at the start. So that's one scenario, and then the other. And the goal there is to create the business and design the business so that it also matches the life they want to be living. Generating the revenue, growing the revenue, is obviously a goal, right? Doing so in a way that's profitable and then gives them the income and the time to be living their life. And this doesn't happen overnight. It's a process, but it works. And then the other scenario where clients have been coming to me is they've had their businesses for years, and they've been service based strictly. I don't typically work with product based clients, and they have, for one reason or another, stepped away or pulled out of being engaged in their business. A client bought a home, another client took a full time job for a bit, right? And then they're like, Okay, well, I'm ready to recommit to doing this, but I need to get the engine going again, and I need help getting that engine going again. So they're coming to me in that scenario, which I have been loving, working with these clients. And I mean, the process is very similar to the first group that I mentioned, but it's just a bit of a different setup. And often, I typically work with women. I do have one man in the mix, because he's partnered with somebody, and I love working with him, too. And but the women come to me like they've been doing the business for a bit. They've, for sure, had corporate careers even prior to that, and they're just, they come with a real enthusiasm and eagerness to get things moving again. So it's really a pleasure to work with them.

Jacki Hayes  17:21

When it comes to folks in either of those scenarios, what are some of the things that tend to trip them up, or common areas of resistance that you have seen in your clients?

Katherine Danesi 17:34

Yeah, fair enough doing business development outreach. I mean, so I and I separate and differentiate marketing from business development, but both, so I have a system and sort of a plan I work with my clients on and getting them to just trust me, this works, and then they start doing it, and it's Like, okay, it's not so bad. Or starting to post on LinkedIn, let's say, and Instagram, where they haven't been, where they've been silent, and helping them come up with a system that doesn't make it onerous to be doing this and also allows them, especially if they're writing blog posts or emails, to repurpose content. So creating those systems around that, and then not necessarily resistance, but I find it's taken time. Especially where rebranding has been needed, that's been a process, and often it's gone on a bit longer, and helping people sort of get through the hump of those, what I would say are the main areas.

Jacki Hayes  18:44

I loved how you shared your journey into where you're at right now, and you it sounds like help others that have that evolution. In some way, I feel often that we put a lot of pressure on ourselves to stay the course, like I've been telling people, this is what I do, and now they're used to this, this is what I do. I can't just switch it up, because then everybody's going to get confused. And yet, every single business owner that I've spoken to, you see an evolution of where they have come from. Some of them are pretty like, wow. And then some of them are like consultants as coach. So it doesn't necessarily, from the outside, seem like as big of a jump to say a fashion designer to something like a copywriter. How do you support your clients in that evolutionary process?

Katherine Danesi 19:37

So it's interesting, and I'm going to add one other thing, and then I think that'll tie it together nicely. The other area where I see resistance is around pricing. Can't believe I forgot to mention that in the first place, most of my clients come to me under charging for what the value for their delivery that they're delivering, and some of. Then, the structure of how they structure their pricing and offerings needs to be addressed. So I think whether it's pricing or marketing, it's for me, it's explaining what I think, what I know, works, and sharing it. I'm happy, because it's really important to me. Somebody will say, Well, should I be doing this platform? Should be posting three times. I'm like, only if you're going to do it. Do what works for you, right? So always tailoring the plan to what works for them, because that will get their buy in, which helps start that evolutionary process, right? Cuz then they're willing to try it. It's a small bet. It's not crazy. Let's see a win, right? And then let's double down. And so when we start accumulating wins in whatever area it is, then we can start building on that and moving through that process. And what I see is that there's confidence gained in that, right? And a lot of the people that I'm working with have been working as because they've considered themselves for so long as freelancers, even though they've had businesses for a few years, right? So getting them out of that Freelancer mindset, which I'm sure you can appreciate, right, as as working from the operations perspective, into thinking like a business owner and like CEO of their business, and eventually managing a team that, for me, is probably one of the more interesting challenge, evolutionary challenges. I don't know if you find the same thing. I'd be curious.

Jacki Hayes  21:36

Yeah, I have seen that. I find people start their business because there's something they love to do, and they do that thing, but there's a whole business around it, and they tend to forget that they're the CEO of all of that, not just a website designer or a brand strategist, it's all the things. And even if they're a solopreneur, and they intend to stay a solopreneur, they're also a CEO and founder of a business, and it does take a little bit of a mindset shift in order to step into that.

Katherine Danesi  22:09

Yeah, for sure, and I, I have found that that isn't I like your word evolution, because it comes up in a coaching call by coaching call basis, right? Like opportunity or challenge will present itself, and the default is to address it the way that they had been, with that other hat on. And it's to suggest that there's a different way to look at it, put the other hat on, and then just sort of work through it that way, and it, yeah, it just takes up. And I think it's that way for everybody, right? Like, I don't, I mean, some people come out being like, Okay, I'm an entrepreneur and I'm running a business. But to your point, the clients that we work with typically had really gained a lot of expertise and talent and all of these things, doing something for other people that they decided, hey, one day, I'm going to do this for myself. Now, right? So it's not natural to think like a business owner. And I think whether it's operations or just higher level strategy, getting them to think like a business owner is definitely one of the things. If I can leave somebody with that, I've done a good job. 

Jacki Hayes  23:19

If somebody was listening to this and they're wondering, hmm, I wonder if I'm stuck in the service provider role or the CEO role, is there a question, a prompt, something that they could use in their head to evaluate whether or not they're thinking of it as a CEO or kind of the employee of the business, one or the other?

Katherine Danesi 23:39

My goodness. Well, I guess probably the first thing is, are they looking to somebody else to give them the answer? And then that's such a real that's a really great question, which I know is buying me time here to answer, but only because I want to be thoughtful about my answer. I'm going to say no. I think for me, it comes up on a case by case specific basis, and I and I just, I need, I would have to respond to a specific scenario, to be perfectly honest, that is fine. 

Jacki Hayes  24:09

I'm always about the personal, personalizing things. So yes, it is a case by case situation. I know for myself. It often comes down to busy work. Am I doing busy work, or am I actually moving my business forward by what I'm doing right now?

Katherine Danesi 24:27

Oh, for sure, but, and, but and I'm going to say, I think that happens, no for everybody, across every stage of your business, I still do it, right? I try to catch myself doing it, but I think that's a fair point, right? And I'm procrastinating doing the thing I need to be doing to work on my business by doing all of these small things in my business, or even small things that somebody else could be doing for me to work on my business, right? So yeah, no, I think that's spot on. I love that. 

Jacki Hayes  25:00

Yeah. Yeah, very much. When I'm procrastinating, I'm on Canva a lot, which is so much common, and I have to stop myself and be like, I'm not a graphic designer. I do not offer graphic design services. I don't need to spend this much time on Canva. It's okay.

Katherine Danesi  25:15

I love that. I love that. That's a great example.

Jacki Hayes  25:19

Katherine, what is something that you would tell your younger self about doing business, or advice that you would give your younger self?

Katherine Danesi 25:32

So I think when I was starting out, I just knew I wanted to work for myself, and I had been trying other things. Just never really got some things to gel, and then this gelled. And I think it's important to know you're never going to have the idea fully baked, right? It's going to change. You don't know. You know how people are going to respond to what you're putting out there and what they're going to want of you. So just do it number one. And I think the other thing that maybe two things like, I should have learned to trust myself more and versus looking to other people, but then at the same time, when I needed help, not I should have asked sooner, and that's something I still need to remind myself of today. I'm kind of a lone wolf. Let's go do it. And I mean, I have an assistant now who loves her, but it takes it. Just yeah, asking for help, getting in community, being with people, sharing ideas. I think that would have served me and my business had I started doing that sooner.

Jacki Hayes  26:40

Katherine, where can the listeners find you?

Katherine Danesi 26:44

Katherine DanesiThank you for asking me that question. So I'm in all the places at Katherine denisi. So my website, Katherine denisi.com and you'll find how to spell that in the show notes on LinkedIn and Instagram. Those are my two platforms at Katherine denisi. And when you're on my website, I put out a weekly newsletter, which is a great way to just see get, hopefully get good advice and suggestions and ways of thinking about your business, and that goes out each Wednesday, and that's available to sign up on my website.

Jacki Hayes  27:13

So thank you so much for being here today. 

Katherine Danesi  27:15

Thank you for having me. Jacki, it was great to see you. 

Jacki Hayes  27:21

Thanks for hanging out with me on Here's What I Learned. If today's episode gave you an aha moment, a laugh or something to think about, make sure you're subscribed to my email list. That's where I share even more tips, stories and behind the scenes insights to help you simplify and thrive and remember you get to do business and life your way until next time, keep experimenting, keep simplifying and keep learning.