How To Overcome 8 Obstacles To A Free-Spirited Entrepreneur’s Success

Written By Ashley  |  Live, Personal, Self 

You always have a choice.

I hear it all the time from small business owners. "Ashley, I'm going to buckle down and focus on my business. It needs to grow, or I need to give it up. Oh, and I had this great idea…." 

There are different versions, but I know as soon as I hear them say it. 

They're free-spirited entrepreneurs, like me. 

[9 Awesome Signs You're A Free-Spirited Entrepreneur]

And the odds are NOT in our favor. 

But I also know how hard it is pin down a free-spirited entrepreneur's success. It's not her fault the ideas rarely become real. Or that the time, energy, and love poured into the business never produces enough profit. It's not her fault that the more she seems to offer, the harder the sales seem to get. 

It's not her fault. Free spirits and business-building are inherently opposite belief systems. So while she believes her lack of true success is because she's not focused enough — the truth is her psyche struggles with success in a modern world.

Free-spirited entrepreneurs think differently than the rest of the world. They see a bigger picture and aren't afraid to live life on their terms. But if you're not turning the profit you'd hoped to see by now in your business, know you're not alone.

But before we do anything about it, you need to understand why a free-spirited entrepreneur's success can be so difficult to grab in both hands. Oh, and why you're jealous of that mom who runs a successful accounting business from home down the street. 😉 I've been there. 

A Free-Spirited Entrepreneur Usually Does These 8 Things

Do most of the reasons below sound like you? 

My guess is yes 🙂 I did these ALL the time, before I learned a system to work productively with on my business, not in the trenches of it all the time. 

Free-Spirited Entrepreneur's Success
NEVER Puts Profits First 

Sure, you want to make more money and see your business grow, but that isn't why you started it. Profits were a by-product of living your dream. And you'll never put profits first. It just won't happen. You're hardwired to value people and places more than profits and productivity. And thank the Goddess we have you! Occasionally, you might create a new priced-right offering, but have you launched it? It makes you think.


Huh? It means you shy away from fully valuing yourself and your business offerings. You say you're going to charge more, but do you? It's hard finding a balance between profits and people that makes your soul feel good. But a free-spirited entrepreneur's success requires believing in yourself! See Point 1^.

ASSUMES What Customers Want

Be honest: When was the last time you launched a business idea AFTER asking paying customers what they could use? After you went to your repeat clients and asked what they needed. With free-spirited entrepreneurs struggling to increase profits, the answer is usually "I haven't had time."

Are Hard To FIND

Yes, you have a website. Yes, it has your contact information. But type something a potential customer would into the search box. "[your service] near me" is always a good place to start. Do you show up at the top? Is your page designed FOR THAT SERVICE? Tech stuff sucks — but Google My Business and your homepage are non-negotiable these days. Help people find you, especially when they're looking!

Has an EGOSITE, not a website

What's your potential customer looking for when they visit your website? They want to explore more about you and your business, yes? No. Potential customers are concerned with one thing: themselves. It's Sales 101, and I know you know this because every customer has a story for you that has nothing to do with you and everything to do with them, right?!

AVOIDS Upsells

Asking for more business leaves a yucky taste in your mouth. I get it. But it also explains why you don't have a defined marketing plan and more consistent repeat business. So ask yourself: Am I more likely to get a current client/fan to try something that benefits them or launch a brand new offering to people I don't know? 


The core of your business is the one that warmly welcomes a visitor and turns them into a client and raving fan. But what happens after that initial sale? No, don't check out! I see you scrolling to avoid marketing and advertising talk. I'm not talking about spending money, but you have to have a system that encourages clients to remain clients! An occasional email saying, "Hey! I have stuff for sale!" does.not.work. if your goal is to be productive and profitable.

Gets HIGH Off Imagining The Future

You know that constant storm of ideas and plans swirling around in your head? It's giving you a hit of dopamine that your daily business life doesn't. It's a vicious cycle (one I'm prone to!) of ignoring the doing for the dreaming because, well, dreaming feels nicer. Schedule some time for brainstorming, write your ideas down, and save them for later! You got enough to work on right now!

So, Sound Familiar?

The good news is it's all in your head. What's blocking a free-spirited entrepreneur's success is all mental. Why? Because change is scary for your brain — no joke! But small changes are what you need to implement in your business to increase satisfaction and profits in your life. 

Stop underselling yourself while taking a hot second to ask your customers what they truly want. Making it easier for people to connect with you AND stay connected will boost customer satisfaction and your bottom line. Zeroing in on your best-selling offerings and then implementing a system to upsell from there will do the same. 

What Will You Do Next?

Every free spirit delights in imagining the future. I know I do. But for that future to happen, ground yourself at this moment, and work on your business, not in it.

Schedule some time to brainstorm and write it down for later. Then focus on finishing what you started. 

And pretty soon, doing will feel a whole lot more satisfying than dreaming. But I know you know that.  

I know you're more than ready for this. So take this step towards more profits. Sign up for our Wysify™ 15-Minute Fix Emails and start doing more and dreaming less. One email, once a week, one task that works on your business, done in 15-minutes or less. Getting productive work done feels good. Try one now. 

The Next Step

I know you're more than ready for this. So take this step towards more profits. Sign up for our Wysify™ 15-Minute Fix Emails and start doing more and dreaming less.

One email, once a week, one task that works on your business, done in 15-minutes or less. Getting productive work done feels good. Try one now. 

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