How I Changed Life (party girl to six figure entrepreneur and back?)

We talk a lot about changing your life here at The Chillpreneur Company, and today I want to tell you the story of exactly how I changed mine. And I know there are a lot of “my business journey” stories on the internet, but I really hope that if you’re someone right now that is in a state of limiting beliefs around whether or not you can become successful because it’s taking too long or because it’s too late, I really hope that this is the video that finally changes your mind and gets you to just stick with the desires that you have in your heart.

If you did like this episode, be sure to screenshot and share on Instagram and, of course, tag me, @erinmayhenry


I know that there is just this unrealistic expectation around time and success. So many of us are stuck in a state of comparing ourselves to other people because of how fast they were able to achieve success. And so many people who have the potential to become extraordinarily successful are giving up because it doesn’t happen within like a matter of weeks or a matter of months. If we developed the skill of learning how to trust our own timelines more, not only would so many of us be far happier in our pursuit of success, but so many people would actually get there because they didn’t give up in the process. 

I am the perfect example of someone who has just stuck with it for a long, long period of time, even though I came from a place that is extremely unsuspecting. I was not someone who was supposed to be here in the position that I’m in today. 

I have built incredible success for myself. I have an online business, The Chillpreneur Company, that has made millions of dollars since I started it; we’ve helped over 3000 students, I have just launched my second business and apparel company, and built this huge community here on the internet as well. But again, this did not happen overnight. And I was not someone who was “supposed” to be here from where I started. 

I wanted to share this journey, you know, not just as another like you can go from broke to being successful. But as an opportunity for you to learn how to trust yourself more. 

Not every person becomes a successful Tik Tok star overnight. For most people, it takes patience, resilience, and a whole lot of trust in the timeline. And so I wanted to share my journey with you today as inspiration for you to just stick with it and to just keep moving forward. 


Before any of the marketing, the social media, and the business, all I wanted to do with my life was to party. From such a young age, all I wanted to do was party and indulge. That’s all I did for such a long period of time. I went out every single weekend for like two years. And I really didn’t have any ambitions for myself. I wasn’t someone who tried hard in school. That’s where I started. 

I wasn’t able to actually go to university after finishing high school because I didn’t have the necessary requirement to get in. So I did what I do best, I took time off. I worked in bars, and I partied. 

And then, at some point in 2010, so two years after I graduated high school, I was watching an episode of Sex in the City, and it was an episode with Samantha Jones being Samantha Jones, and I thought, “I could do that.” Partying, PR events, living this like Sex in the City lifestyle. 

Now, I didn’t know what public relations was but I went and googled it, and apparently, it was something that you could study. So I enrolled in a marketing and PR class.

You would think this was my wake-up call, but no, I still did the same things. I went and partied, I skipped class all the time. But somehow, even though I wasn’t focusing, I did pass a lot of my subjects. 

I did the absolute bare minimum until one day, I went into the library and watched a video from Eric Thomas called the Truth. 

This video shook me to my core. You know, he was talking about success and how if you want to be successful in life, you really need a try. It’s a little more on the hustle side of things than I appreciate these days. But at the time, it was the wake-up call that I needed

It just clicked something in my brain – if you put effort into something, you can achieve a result. 

And so I did,  I actually started trying hard.


What happened after that changed the course of my life forever. A few months later, it was required for one of my classes that we went to this PR event. This was in October 2014. 

At this event, I was tuned out, switched off from boredom. But there was one speaker who said one thing that just clicked for me. 

He said, “If you want to ride the wave of digital entrepreneurship, the first thing you should do is get online and build an audience.” I know that’s obvious now, but at the time, I didn’t even know what digital entrepreneurship was but I felt CALLED to do it. 

Two days later, I started my YouTube channel. I filmed it on my laptop, it was terrible. I didn’t fill in my eyebrows because it was 2014. 

I had no direction. I hadn’t really no clue what I was doing. I didn’t have any purpose. I didn’t have any intention. But I just kept posting. I “went online and I built an audience.”

And after graduating from university (top 15% of my class btw) and being made redundant from the wine company I had been working at, I started my first business – a Social Media Marketing Agency. 

I liked it at the start, but after a while, I just started to feel bored. 

My “I could do that moment” – 2017

One day I was watching Tony Robbins. He was up on stage. He was talking to people. He was inspiring them. And he was teaching them things. And I thought “I could do that.” So that’s what I did. 

I really just saw Tony teaching, coaching, and mentoring. And even though I was doing marketing for myself and I was doing it for other companies, I wanted to teach it. I wanted to teach business. I wanted to teach mindset. I wanted to teach marketing. 

And so that is when I started the business that I had today. 

But the first thing that I did to start my business was feel totally overwhelmed. I wanted to teach people marketin, business, mind, but I had no idea how to do that. So I went down the path of getting mentorship early on, I hired a business coach, and it was one of the scariest decisions that I ever made. 

And that is when I launched my business mentoring business. 


In the first two years of my business, even though I was successful, I really didn’t know how to trust myself. You know, I found myself trying to replicate all of the people within my industry at the time – Marie Forleo, Amy Porterfield, Jenna Kutcher, the big Boss Babes in my industry. And I thought I needed to be them in order to be successful. 

I completely let go of the sides of me that were adventurous, kind of a tomboy, not serious at all. Because I thought I needed to be more mature, more serious. 

And because I was so trusting of everybody else, I didn’t learn how to truly lis
ten to my own voice. I didn’t learn how to trust my own timeline. Not only was I regularly comparing myself to other people, I felt uncomfortable in my own skin. I was just trying to be what I thought I needed to be to be successful. 

It got really hard. I started to feel quite anxious and 2018 became a really difficult year for me. 

I actually had a mentoring session at the start of that year, and I actually pitched them the idea for a program that would eventually become my most successful program. But in 2018 that highly sought-after mentor told me nobody wants to learn to be an influencer, they just want to learn how to make sales, and so I didn’t make it. 

I didn’t know how to listen to my own creativity. I didn’t know how to listen to my own voice. All I knew how to do was try to be like other people who I already saw as successful. 

We’re told that success leaves clues that we should just find something that works and essentially recreate it for ourselves. And I thought what that meant was that I needed to be serious, I needed to be older, I needed to be more mature, I needed to be just taken more seriously. 

Simultaneous, I started going through a lot of struggles in my relationship. So not only was I not being truly authentically myself in my business, I also wasn’t being authentic in my relationship. You know, I started feeling like a shell of myself.


2020 itself wasn’t actually transformative for me, I just survived, like everybody else did. But it did give me a lot more time to think, it gave me a lot more time to reflect. 

And so, at the end of 2020, I actually made the big decision to finally leave my long-term relationship.

So at the start of 2021, I went into the year, by myself, in my house. I’d never lived alone before either. But I was finally really truly by myself. And I know a lot of people struggle through these lockdowns, but what I will say is it was the most transformative experience that I’ve ever been in. And this is why I’m such an advocate for telling you to spend more time alone. 

If you want to become the coolest person, you know, the first place you need to start with is your relationship to yourself. You can love yourself inherently. But getting to know yourself. Learning to like yourself is a whole nother thing. 

For the first time in my life, I really connected to who I was. And the funny thing was that the person that I had put into a box – the fun, the tomboy, the party-loving person – I thought I needed to let go of to be taken seriously in life and in business came back to the surface. 

I truly got to know who I was. And my business actually ended up skyrocketing. 

I finally launched that course that that mentor told me not to do, and I had so many people commenting saying “Erin, you’re such a vibe.” “your energy is just so on point.” My business income doubled. I launched my most successful program – and it all came back to just trusting who I truly wanted to be.

And what that did is it started to really allow me to develop my values, which is a big part of how I run my business today. One of my values is fun. One of my values is freedom. Really becoming the coolest person, connecting with yourself. And that guides so much of how I’m able to stay stable in my business. 

If you can develop the skill of really listening to yourself for how you want your life to look to what’s important to you, you are going to just navigate life with so much less stress and so much less pressure. 

I allowed myself to show up for my business in a way that was so confining for such a long time. and as soon as I let the gates of my authenticity open, everything started to boom. You’ve got to find your own pathway. 

So many people give up because Susie over here did it in three months and did it in this way. And you try it, and it doesn’t feel good, and it doesn’t work for you, so you quit. Find your own pathway to success, be who you truly want to be in life. And in business. 

There is no one perfect pathway toward anything. There is just so much opportunity out there for you to create a life and a career in a way that is totally authentic to you. But every time you go down a pathway that was mapped out by somebody else, I guarantee you you are going to run into so many roadblocks to the point where you just cannot continue. When you really pave your own way, when you really pave your own path, trust your own timeline, things will happen as they are supposed to happen. You will be successful. You will grow your audience. You will make the money when you’re supposed to make it. If you continue to show up and strategize and innovate and iterate. But you will distract yourself from the comparison, from the pressure, if you just do it in a way that is fun and authentic to you. 

Be resilient get to know yourself. Get creative, be innovative, but just stick with it.



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