Aug. 31, 2021

How Chasing Freedom as an Business Owner will Keep You Broke and Unhappy

How Chasing Freedom as an Business Owner will Keep You Broke and Unhappy

Most business owners seek the freedom entrepreneurship affords them. And in today's episode, Kathryn shares how chasing freedom will keep you broke and unhappy.

Most business owners seek the freedom entrepreneurship affords them.

And in today's episode, Kathryn shares how chasing freedom will keep you broke and unhappy.

So if you’re a business owner chasing freedom, tune into this episode, as Kathryn shares her perspective on why it’s important to cultivate freedom into your day-to-day life instead of chasing an arbitrary idea of it somewhere in the future. 


  • Why chasing freedom is a quick fix and will keep you chasing, broke, and unhappy.
  • Why looking outside yourself at other business owners for how great the freedom lifestyle is might not be totally accurate.
  • How the marketing industry loves selling the escape, and how you might be falling into that trap.


If this episode inspires you in some way, leave us a review on Apple Podcasts and let us know your biggest takeaway–whether how chasing freedom will keep you broke and unhappy or how the marketing industry loves selling the escape, and how you might be falling into that trap.

And while you’re here, make sure to follow us on Instagram @creativelyowned for more daily inspiration on how to effortlessly attract the most aligned clients without having to spend hours marketing your business or chasing clients. Also, make sure to tag me in your stories @creativelyowned. 

To get your hands on how to write content that connects, and attracts the most aligned clients, grab it here!!

Here’s the blog post that was published on Screw the Nine to Five: HOW ‘CHASING’ THE FREEDOM LIFESTYLE WILL KEEP YOU BROKE AND UNHAPPY


Two years ago nearly the day I published a blog post on Screw the Nine to Five about how chasing freedom as a business owner will keep you broke and unhappy. 

At the time I’d been the proud business owner of a local brick and mortar. But I was also deeply unhappy. I know it seems weird to say I’m proud and unhappy at the same time. But I was proud of what I built. I just knew it didn’t afford me the thing I desired most–freedom. 

Something the majority of business owners and entrepreneurs I talk to say is the biggest reason they started their own business. It's why I started chasing freedom in the first place. But if you’re like most business owners I talk to, running your business doesn’t afford you the freedom you expected. In fact, most business owners say they work way more and a lot harder than they ever did in their previous jobs. 

Perhaps it’s the neverending to-do list that never actually gets done but as a business owner, you feel the pressure to get it done sometimes at all costs. Maybe it’s the late-night sessions trying to get your books in order so that they aren’t a complete mess when tax season rolls around. Maybe it’s working the entire weekend because your staff called in sick and you need someone to open your store. Heck maybe you’re a solopreneur right now, and you’re wearing all the hats. All 500 of them.

From tech support to a customer service representative to inventory manager to bookkeeper to marketing manager and the list goes on. It makes chasing freedom appealing I'd say.

Personally, I know I took way less vacation than my 6-figure corporate career offered which was 5 weeks. 1 to 2 weeks was all we could manage at the time. That was my reality. 

But two years into my business, I felt duped. Duped that chasing freedom wasn't turning out the way I expected. Nothing about owning a brick and mortar felt like freedom to me. I often said I traded in a corporate career for two corporate careers and then some. Now brick and mortar retail is a different ballgame compared to the online coaching space so they can’t be equally compared. It’s why I started to explore the online space because I saw so many online business owners claiming to work WAY less and make WAY more money. Sounds amazing...but having already felt duped (and I’m the only one to blame for that) I started down the path of contemplation...

Was chasing freedom keeping me broke and unhappy?

Are business owners being sold on the escape for freedom but in reality most business owners aren’t experiencing that themselves?

What does freedom mean to me?

And here’s what I discovered!

Chasing freedom as business owners will keep you broke and unhappy. A pretty bold statement but it’s true. Because what’s at the end of the ‘chase’ will only fulfill you for a short period of time. It’s because you’re not currently satisfied with the freedom you already have each and every day so you’re looking outside of yourself for something to fix that. 

A new business venture, car, trip, or article of clothing.

Now I’m not saying you shouldn’t desire a different lifestyle or business. What I am saying is that chasing it isn’t going to make you happy or fill your pockets full of moolah. Happiness within has to happen first. It’s about finding inner peace with your current situation even if it sucks. It’s sitting with the uncomfortable feeling that you want more or something different even if it takes time to make that shift. It’s getting curious about the restlessness in your body, and what’s causing it. 

It’s from this place of BEING as a business owner where you’re not chasing freedom but instead creating it in your day-to-day. Right now, at this very moment. Because chasing energy is an attempt to escape your current reality. The problem is that good feeling hits when you start something new but it won’t last. 

Retail therapy is a prime example where you buy something at the moment and it makes you feel good. That’s a dopamine hit...It’s a distraction from a much deeper lesson, knowing, and learning that comes with stopping the chase as a quick fix and escape. 

And ‘selling the escape’ is something the marketing industry is really good at.

Think about it...most ads or sales messaging paints the picture of what you are currently unhappy with within your life or business and they sell you on a solution or your greatest desires (aka an escape). This might be a short-term fix like taking a trip. “Escape the winter with a trip to the Caribbean,” is a great example of that and plays right into the hearts of people chasing freedom. Freedom from their job for even a week. And it’s an ad messaging I see every winter. 

Since selling my brick-and-mortar business over a year ago, I noticed in the online space how heightened this message was, especially in the online coaching industry.

Coaches sharing how little they work, or how they can nap during the day when they feel like it. Here’s the thing...the majority of online business owners that I’ve talked to aren’t experiencing the freedom they desire, which always has me question the truth about things. And makes me wonder if that's why chasing freedom is something so many of us do.

Are business owners painting the real picture or a curated one? 

I care because integrity and truth are two core values of mine. And when the majority of online business owners share with me that they are unhappy in their business because it’s not affording them the freedom they thought would come with being their own boss, I get uber curious. And I've discovered like me lots fell into the trap of chasing freedom.

And I take full responsibility for that. But the travel photos and workless movement really played on my psyche. The problem with selling that is freedom for one person will look totally different for another. I also noticed that a lot of the business owners who preach this work-less, freedom lifestyle are ALWAYS working. And for some maybe that is what freedom is for them. But when I see business owners sharing how little they work but they are launching live courses every 6 to 8 weeks, back-to-back all year long that is working consecutively without a break, and a break from having to take coaching calls or show up to coach essentially weekly. Yes, you can sit by a palm tree but still be working. And for me, that is not freedom, or at least what I thought I was getting into when I was chasing freedom.

Because you’ve just changed the scenery of where you work, not how much you work. And I think most online business owners can agree that ‘freedom’ doesn’t mean working week in and week out even if you’re sitting poolside.

But maybe I’m wrong... which leads me to the final thing that I learned after contemplating why chasing freedom was keeping me broke and unhappy. It's because...freedom looks different for everyone. 

That's the beauty of business owners. We get to choose what freedom looks like for us in our business and if we aren’t experiencing it, how can we create it right now in small steps to eventually get us to a point where we want to be so that we ditch chasing freedom and we create it instead. 

I also think you’ll keep chasing freedom until you take the time to define what freedom is and even more importantly what it isn’t for you, something other people can’t do even if their life seems pretty awesome.

Here’s what freedom is to me and what it isn’t, something I only learned after I stopped chasing it. Because chasing freedom also has you chasing an arbitrary idea of what you think looks good on other business owners.

For me, freedom isn’t launching every 6 or 8 weeks. It’s not having back-to-back course offerings where each week has coaching calls or appointments in my calendar. Freedom isn’t having to ‘show up’ despite being sick or burnt out. This is the main reason I believe chasing freedom keeps me unhappy. Freedom isn’t selling others on the idea of it, it’s helping them define it for themselves. Freedom is less about money, career, or job and way more about the environment and experience. What I mean by that is, I live for experiences. And it doesn’t have to be traveling (although I really love to travel). It can be taking an evening stroll, hanging with friends and playing board games, cooking (or experimenting as I like to call it) in the kitchen, and enjoying a lovely meal afterward, it’s attending a live performance, getting lost in a good book, or sitting in the backyard listening to the bird's chirp. For me, life is about experiences and soaking them up. So as a business owner if my business doesn’t afford me that, I don’t have the freedom I want. So it's less about chasing freedom to fix this situation and more about creating it within myself first.

Freedom for me is also learning to let go, take a step back or quit when it’s no longer serving my well-being. That can look like getting sick, being burnt out, or just not being lit up by what I’m doing anymore. My hope is for online business owners and entrepreneurs to create freedom in their everyday life. And for the marketing space to stop selling the escape, or what people are missing. 

Our next guest Jenne Sharpe calls it dangling the carrot. And I’m so stoked to have her on the next episode because Jenne is sharing how to strengthen your intuition and tap into your feminine energy so that you can find a balance between the masculine and feminine energy in your business. 

I hope this has inspired you to contemplate as a business owner where you might be chasing freedom and why that might be causing you to be unhappy in your business. But more importantly, give you clarity around what freedom means to you and what it doesn't. This is also your permission to create that in your everyday life. 

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