Leading with Fun: A Smarter Way to Succeed

There comes a point in business where everything might look like it’s working. Your offers are converting, your calendar is full, and people see you as successful. But inside, you feel disconnected, tired, and out of sync with the work you’re doing.

That’s exactly where Hannah McKitrick found herself.

Hannah is the founder of Dolce Vita Experiences, a business built around retreats, aligned living, and helping women bring joy back into how they lead. In our conversation on The Amanda Kaufman Show, she shared her journey of shifting from pressure and performance into alignment and authenticity. Her story is a powerful reminder that joy isn’t a luxury. It’s a strategy.

When “Success” Stops Feeling Like Success

At one point in her career, Hannah was doing all the right things. Her brand was working. Her offers were selling. From the outside, everything looked great. But she wasn’t excited anymore.

Instead of forcing herself to keep going or chasing the next goal just to feel something, she stopped. She took a breath. And she asked herself the one question most entrepreneurs avoid:

Does this still feel like me?

That honest check-in became the start of something new.

How Dolce Vita Was Born

Hannah didn’t start over from scratch. She reconnected with what had always been part of her. The experiences, the freedom, the joy, the travel, the food, and most of all, the feeling of being fully alive.

That led to the birth of Dolce Vita Experiences. This wasn’t just a rebrand. It was a return to what felt good. A business model built around aligned strategy, intuitive choices, and creating transformational experiences that are rooted in fun and depth.

Fun Is Not a Distraction

One of the most powerful moments from our conversation was this:

“What’s fun for you is what will allow you to achieve more.”

That hit hard because so many of us are taught the opposite. We’re told to hustle, grind, and push. Then maybe enjoy things later. But what if the things that light you up are actually pointing you to your most aligned success?

Hannah is proof of that. Her retreats aren’t just about wellness. They’re about helping women access more of themselves. Not through pressure, but through play, joy, connection, and experiences that shift how they show up in life and business.

When It Feels Off, Pay Attention

Something Hannah shared that really stuck with me was how she used her own energy as feedback. She paid attention to what felt heavy and what felt exciting. She didn’t use that information to quit. She used it to make better decisions.

Instead of pushing through the parts of her business that drained her, she let them go. She made space for new ideas. She followed what felt good, even if it didn’t follow a traditional strategy.

That kind of trust creates momentum you can’t manufacture with just tactics.

The Most Transformational Work Comes from Lightness

Hannah talked about how her clients come to her retreats thinking they need more discipline or structure. What they often discover is that their breakthroughs don’t come from fixing something. They come from reconnecting with joy.

Fun doesn’t mean surface-level. It means lightness with depth. It means giving yourself space to explore, play, and expand.

That’s where lasting transformation lives. Not just in working harder, but in reconnecting with what feels true.

You Don’t Have to Choose

This is one of the biggest takeaways from our conversation. You don’t have to choose between being successful and feeling good.

You can do both. You can want growth and crave joy. You can be driven and still have fun. You don’t have to earn your alignment after you burn out. You can lead with it.

In fact, leading with joy might be the smartest business decision you make.

Give Yourself Permission to Evolve

When Hannah shifted from her original brand, My Intuitive Health, she knew it had served a purpose. It helped her clients. It helped her grow. But it no longer reflected who she was becoming.

That’s not failure. That’s growth.

Too many entrepreneurs hold onto something that no longer fits because they’re afraid to start over. But evolution is not a step back. It’s often the thing that unlocks your next level.

You’re allowed to change. You’re allowed to choose something that feels better. You’re allowed to outgrow what used to work.

Final Thoughts

This conversation with Hannah was refreshing, grounding, and a much-needed reminder that business does not have to feel like a battle.

You can build something real. Something joyful. Something that feels like home every time you show up for it.

If you’ve been questioning your direction, feeling stuck in a strategy that no longer excites you, or wondering if fun belongs in business, this is your permission to shift.

Go listen to Leading with Fun: A Smarter Way to Succeed on The Amanda Kaufman Show. The moment you stop forcing is the moment things begin to flow.

Fun is not the opposite of success. It is the path to it.

Chapters List

00:00 Introduction to Dolce Vita and Purpose-Driven Entrepreneurship

03:31 Hannah's Journey: From Corporate to Culinary Adventures

07:09 Redefining Achievement and Success

10:59 Creating Transformational Retreat Experiences

14:27 Navigating Change and Embracing New Directions

Full Transcript:

Hannah McKitrick (00:00)

I am a firm believer that what's exciting you is your path and what you're what you're not looking forward to. What's what you're stressing out about what

feels dreadful, that's not a signal to push harder.

Amanda Kaufman (00:32)

Well, hello and welcome back to the Amanda Kaufman show. Today I'm joined by Hannah McKittrick. She is an absolute genius when it comes to Dolce Vita, a travel, wellness and personal growth company that helps purpose led women live, lead and nourish from deep alignment. She hosts luxury retreats across Europe.

She hosts coaching workshops. She does mind body cooking experiences, which sounds very, very cool. And she works with high achieving women to help them to recalibrate their nervous systems. leading, helps them to lead with joy and build a life that feels as good as it looks. Her work blends aligned business strategy, intuitive health and energetics of ease to help women to stop forcing.

start magnetizing and to come home to a version of success that is both soul led and sustainable. Hannah, welcome to the show.

Hannah McKitrick (01:31)

Thank you so much, Amanda. So excited to be here.

Amanda Kaufman (01:35)

I love it, I love it. And you you have such a really interesting blend and a very intentional kind of way that you've packaged a lot of your expertise, but I'd just love to ask entrepreneurs, what led you here? You know, why focus on supporting women in this particular way?

Hannah McKitrick (01:55)

Yeah, so I feel like as many entrepreneurs can relate, it was my life journey that brought me here. And there's so many different micro pieces that led to it. And I wish I could say it was one big thing, but really it was so many different things that led up to this. And I'll give you some of the highlight reels of that, because I don't want to just give a blanket answer.

One of the pieces is I had some struggles early on in my childhood and teenage years, both with health and anxiety that just made me feel so heavy energetically. And I really was at war with both my mind and my body and really just not in alignment, if you will. And when I was 19, I had to learn how to use, I chose to.

learn how to use food to actually heal my gut because the doctors were going to have to do surgery and all of this stuff. And meanwhile, after college, I started working in my first corporate job. And like many entrepreneurs, pre entrepreneurship, I was bored and I was, you know, commuting to the office and doing the thing that I was supposed to be doing. And it was fun for a little bit. And then I was like, what's next?

Like I just got bored. And so I decided to follow one of my passions that didn't necessarily equate to career success, but I just wanted to do it. And that was quitting my job and going to culinary school in Italy because why not? I was 23 and I love food. I love cooking, love Italy. So I did that and that experience definitely...

opened my eyes to Dolce Vita, the sweet life, and really set the bar for how good life could be. Like, I really experienced this euphoria that I didn't know was possible. And I even got tattooed on the back of my neck, Dolce Vita, because I never wanted to forget, because I knew how much corporate can kind of suck you into mainstream and all of that. And so when I came back home, I kept trying to

figure out how to bring that Dolce Vita essence into what I was doing and everything kind of fell flat. And so I just continued following my passions, which for me looked like I went to London to study nutrition, went to Malta, got my yoga teacher training. And then finally, when the pandemic happened is when I decided to bring it all together. And I did get a pretty direct download that was said healthy cooking, retreats, Italy, wellbeing.

and I was like a business and I was like, that sounds so fun. And then I just Googled, how do I host a profitable retreat? And then here we are.

Amanda Kaufman (04:38)

That's amazing. Yeah, that's incredible. you know, it takes a lot of courage to choose your own path. You know, there were a couple of points in your story where I'm like, goodness, it sounds like there was actually a lot of pressure at those different junctures where you then decided to respond to that pressure by going like, I need to seek, I need to find. And then here you are, like you've discovered so many cool passions and developed quite an interesting resume.

as a result of that. Did you have a lot of people around you who traveled or went to these places? Like, can you talk to me a little bit about the, what led you to go, you know what I'm gonna do? I'm gonna go to Italy. You know what I'm gonna do? I'm gonna go to London. You know what I'm gonna do? I'm gonna go to Malta. Like, that is not a typical way to problem solve and to think about things.

And I'm just curious, did you have inspiration around you of people who had done similar things or was this really coming from somewhere else?

Hannah McKitrick (05:42)

Yeah, so this was definitely coming from somewhere else. And actually it took it took a lot to go against the grain because it was I felt like I was almost being gaslit by society because I was like, you know, people are doing this thing day in and day out working. and I love achieving like I love, you know, doing the thing. And so I was doing the thing, but I was like, really? And so for me, I was craving on a deep soul level more.

vitality, more excitement, more fun. you know, traveling has not always been easy for me. And it's still not always easy because in traveling, yes, you're gaining all this excitement and fun, but you're also leaving behind comfort and security and stability. And so it was one part like I want to push myself and I want to grow because I know that leaving this behind will allow me to stretch to another level.

But the other part was just, it was yearning for something more is the best way that I could describe it and something unique. Like I was, I don't know if anyone listening is familiar with Enneagram, but I'm an Enneagram seven, which is kind of like the fun lover. so it makes a lot of sense. Yeah. And so it makes a lot of sense that I was wanting these experiences. And for me, I always thought after

I never wanted to go back to school per se, but rather I wanted to learn in the field. I wanted to learn by doing. And so I really felt like these experiences were what shifted me and allowed me to grow as a person and also learn while playing.

Amanda Kaufman (07:15)

This is so juicy, know, because more of an Enneagram three, very, I tend to be like pretty structured, very, you know, driven as well. And I think it's so cool how you called out your achievement orientation because I think a lot of people can really relate to that. You know, we want to get good grades. We want to hit high scores. But what you did that I think is remarkable and definitely something that our listeners can learn from is you didn't deny

that you are an achiever. Instead, you redefined what achievement actually meant to you. And you know, like it, I've had the corporate lifestyle as well. And I just remember it was so gray, you know, the fluorescent lighting to save money and just drab and carpet on the walls to dampen the sound. And it was just like, this doesn't, this feels so, so institutional, but not inspirational.

you know, and, and you have these people sitting in these environments all day long, traveling for goodness knows how long to get there in order to get the paycheck. And it's like, all of that would be fine if your achievement was in very high alignment to that environment, you'd tolerate that environment. But if your achievement is not aligned, and then you find yourself in these environments, you know, I think a lot of people could choose

Hannah McKitrick (08:07)

Yeah.

Amanda Kaufman (08:35)

Well, achievement is no longer important to me. But the thing is, is that it's going against your nature. But if you define your achievement, if you redefine like, well, what is my purpose? What is my success path? You know, that is extremely courageous. And I also want to call out like, it's often so difficult because no one around you is doing it. How did you solve that? How did you solve for?

Hannah McKitrick (08:40)

Totally.

Mm-hmm. Yeah.

Amanda Kaufman (09:00)

the social aspect of your joy and your happiness.

Hannah McKitrick (09:04)

Well, I'll tell you in one sec, but first I want to say something that was actually landing hard as you were talking, because I mistyped for many years as an Enneagram 3 and actually had a switch recently. as you were talking, what drew me to this is I didn't want to choose. I didn't want to choose between the achievement and the fun.

I and this have the same thing happened with health. I didn't want to choose between being healthy and having freedom and flexibility. that largely stemmed so much of my work with the cooking experiences. And now with these like retreat, Dolce Vita experiences, it's it's allowing people to not choose between fun and achievement and taking it one step further. What is fun for you is what will allow you

to achieve more. It's what will be guiding you towards the path of deepest alignment, of that magnetism, of the path of least resistance. And I think at the time I was subconsciously trying to kind of merge those two roads together.

Amanda Kaufman (10:04)

I love that. I love that. You know, I'm thinking about how constraints can really lead us to this creativity and, you know, rather than giving up and reconciling and just sort of saying, well, you know, I guess my health is what it is or well, I guess this is the career path that I chose. Let's buckle up for the next 50 years, you know. You decided to lean into the constraint and activate your creativity so that you could literally, you know, have it all.

Hannah McKitrick (10:22)

Yeah, right.

Amanda Kaufman (10:31)

That's so super cool. So where are you headed now? What do you focus on the most in your business? I understand you're going through a pretty exciting season right now in your business.

Hannah McKitrick (10:42)

Yeah, yeah. So I am obsessed with creating experiences for people that blow their mind and shift them at the core through a pathway that is, spoiler, fun, because I'm a fun junkie. so, yeah, exactly. And so my business started out as My Intuitive Health, and that served me for many, many years. And how

Amanda Kaufman (10:57)

I'm surprised.

Hannah McKitrick (11:07)

on all levels, right? Soul health, physical health, mental health. And I did those cooking experiences so that people could not have to choose between being healthy and enjoying their lives and bringing the flavor into the food and the community. But now my work has really dialed in on these retreat experiences. So I'm obsessed with leading retreats. They are so magical, so transformational.

And I'm also, the way that I host a retreat is equal parts depth, like soul depth, and then also just like lightness, lightheartedness and playfulness and fun so that people can really, yes, bring intentionality into themselves and get a deeper understanding of themselves, but also integrate joy.

because there's no point in self-growth if you're just trying to fix yourself the entire time and look at what's wrong in all of this stuff. I think a big part of self-growth is actually going out onto the field and having fun and doing the thing of why you're trying to grow in the first place. And so my rebrand is into Dolce Vita experiences and Dolce Vita, means sweet life. And so bringing that sweet life essence into

business into yourself, into your food, knowing that that essence is who you really are. Like we are designed for joy and like that is a signal from the universe that you're on your path. And so it's bringing that into, into everything you do. And so I do this through retreats and Italy, Greece, dinner club parties that I host here in Boston and the essence of

all of them is just to bring you back to who you are, which at the end of the day is just being incomplete non-resistance to yourself and that alignment within yourself.

Amanda Kaufman (12:49)

you

That's so powerful. a lot of our listeners are aspiring entrepreneurs or even established entrepreneurs. But something that's happening right now, at the time that we're recording this, is I'm calling it this great pivot. It's this huge opportunity for people to really step in to another level. And that pivot is being activated by a lot of different factors.

AI for sure, big, big, big time, a lot of social changes, a lot of economic changes and pressure. I think a lot of entrepreneurs are getting a little stuck. And what I notice is you are pivoting. You're making the choice to pivot. And I'm just so curious, how did you know that it was time to make that change?

Hannah McKitrick (13:40)

Yeah. So for a while I was grateful for the business name that I chose, intuitive health, because I was like, this is awesome. It's so broad. It's so all encompassing. Like this will grow with me for a while. And then, you know, I am a firm believer that what's exciting you is your path and what's what you're what you're not looking forward to. What's what you're stressing out about what

feels dreadful, that's not a signal to push harder.

That's a signal to shift or shed something. So to shift what you're doing, shift the pathway there, or just to release it. And so I was taking inventory recently and I realized that I've not really lit up about health anymore and talking about it. Like, I don't know. And I was thinking like, for my clients even,

The transformation that they were going through, yeah, at the beginning it definitely was like they had huge shifts in the kitchen, but really the big shifts that happened on the retreat, it had nothing to do with food. It was all about themselves and that bringing more joy into their lives. So I was like, okay, well that's a little deceiving, the brand name. And people would think my retreats were about health. And I was like, they're not. And so that was one piece. And then the other piece was I realized that what was falling flat,

were some of the, like I said, like the health stuff and the cooking stuff. And what was feeling exciting was more of the experiential stuff. And so I had that awareness and then I quickly tried to shove it down, right? Cause like, I feel like once you realize that something's flat that you've been doing for so long, you're like, well, no, like that can't be true. So I tried to shove it down, but then the name dropped in.

Dolce Vita and I was like, that's what this is about. And I have the sign, people might not be able to see, but it says Dolce Vita above me. I've had this way before the brand. I've had the tattoo way before the brand. And all of a sudden it just felt like I could stop resisting or trying to connect, force my brand together.

Now it just all makes so much sense of what I'm doing and why I'm doing it versus before I used to have to kind of like piece things together of like, it's this and it's this and it's this. And now it just, this overarching umbrella just, it's like a sigh of relief. Like, yes, I'm home.

Amanda Kaufman (16:04)

Yeah, I think that's so,

so beautiful. There's a lot of, there's a lot of debate and discussion in the entrepreneurial and online world about hustle culture, ease and flow. Like you've got to grind, you've got to do it. and it's, so interesting because you can sort of see like people building two different camps around it. I think what's really interesting is in your reflection is it wasn't just, I like

La Dolce Vita, like it was also seeing because you were doing, but seeing what your best clients were really responding to and what they were doing. So you were taking in, yes, like everything around you, but you were also seeing the flow in the business itself because you got into action. And I think a lot of people are really hesitant to get into action because like, what if I pick the wrong vehicle?

What if I pick the wrong thing? What if I pick the wrong idea? And I mean, like that feels like something you probably help a lot of people with is just sort of like drop in and like pay attention to what yes lights you up, but also is lighting up other people around you and give yourself that permission to pursue.

Hannah McKitrick (17:06)

Thank you guys.

Exactly. And permission for it to not, um, to not see all of the pieces right away. Like I think it takes multiple years for people to really understand their brand. And like, it makes sense that after five years, I'd have a pivot. Like I was a baby, you know, and, now.

Amanda Kaufman (17:35)

I'm just

thinking back to starting out. That one thing you just said, was the most resistant to that. like, nope, I'm going to be the exception. Million dollars in a year.

Hannah McKitrick (17:44)

Totally, totally. And now I'm like, oh, I can finally talk about who I serve without like crying and like, you know, or like, can actually say what I do without like panicking. And I think it takes a while just to kind of see, see what people respond to, see what you respond to. It's a, it's a combination of what's exciting you and what, and also the feedback from both clients and the universe and what's coming to you easily, what's flowing, what's not, and just.

Amanda Kaufman (17:58)

So good.

Hannah McKitrick (18:13)

doing that dance between your intuition and what's happening.

Amanda Kaufman (18:18)

Thousand percent. love it. I love it. Hannah if people really wanted to keep up with you, what's the best way to do that?

Hannah McKitrick (18:24)

Yeah, I'm pretty active on Instagram. So my Instagram is just hannah.mckittrick, M-C-K-I-T-R-I-C-K, and send me a message, say you heard me on Amanda's show, and I'm sure we'll have tons of business intuitive stuff to nerd out on.

Amanda Kaufman (18:41)

I love it, I love it. Well, congratulations on the rebrand and the discovery. I'm super excited for you and your upcoming retreats and events. And thank you so much for being on the show.

Hannah McKitrick (18:51)

Yay, thanks for having me.

Amanda Kaufman (18:54)

My pleasure. And dear listener, before you go, make sure you smash that subscribe button so that you don't miss another episode. And if you love this, if you've got a friend who is needing to hear that they can pivot, they can choose the fun and aligned way, be sure to grab the link to this episode and share it with your friend. You can just text it to them. You can send it on Messenger. You can send it in DM. Just share the love. And finally, if you really are loving the show and we're having a positive impact on your day,

One of the best ways you can let other people know that this is worth their time is actually doing a review. So if you just take 30 seconds and leave a review on whatever platform you are listening, we always really appreciate it because it helps others to choose the show when they have a lot to choose from. So thank you so, so much. We'll be back with another episode very soon, but until then, make sure that you just do what matters.