Confidence-Building Tips for Creative Business Owners

You know what makes the already difficult job of being a business owner even more difficult? Poor self confidence.

You know what makes the journey and adventure of running a business way more fun? Healthy self confidence.

So, how will we get you there?

I’ll be honest; I have pretty terrible self esteem and self confidence in all areas of my life… except for in my duties as a business owner. For whatever reason, I’m confident in myself, my work, and my interpersonal abilities.

But if I think about it, that confidence didn’t happen overnight. In fact, as a woman truly lacking in confidence, I had to take a moment to pause and wonder what on earth went awry to make me feel fairly confident in my abilities to sell, book, and work with the people I love. 

And then it dawned on me: I’m confident because I’ve obtained the skills I’ve needed to tackle everything that comes my way.

You see, unless you’re an inherently confident person, building your confidence as a business owner starts with skillding blocks (building blocks + skills = skillding blocks. My husband will enjoy that wordplay). Those skillding blocks – sorry, I’ll only use it like five more times – get formed and strengthened through repetitive practice and patience. 

So, I want to give you some tips to help form those skillding blocks that’ll serve as the foundation for your confidence as a business owner.  

Three tips to build your self confidence as a business owner

1. Take more discovery calls.

I realize that I, along with countless other freelancers in this creative world, have said my piece about the importance in vetting your potential clients and leads before speaking to them – preferably through a good intake form. 

While I’m not deviating from that belief, I am saying that when building self confidence, there’s nothing quite as powerful as speaking to potential clients and leads, on the phone, on a regular basis. 

In the corporate sales world, employees are put through the ringer with countless practice calls and scenarios – usually with the rest of the team watching, or participating. Those experiences were horribly humbling (losing my breath just thinking about it) but they were highly effective. Not because they were embarrassing, but because they forced me to learn how to roll with whatever weird thing the potential client might send my way, and think on my feet.

As a business owner and likely solopreneur, you don’t have that opportunity. So, you need to create that opportunity for yourself. 

That said, I never want you to waste your time for an indeterminate amount of time. So, set a specific amount of time, like a month, where you take whatever discovery calls might come your way. You’ll get two major benefits out of that trial period: 1) you’ll get the chance to practice, practice, practice and 2) you might even find that you end up loving a few of the people you get a chance to speak with.

At the very least, you’ll have some funny stories to share. 

2. Go out and hunt. (Not for animals)

I don’t know about you, but nothing makes me feel less confident than sitting and waiting for some good thing to come my way. Confidence rarely comes when leaving things to chance. 

I’m fairly certain that we can all think back to a time where we went to whoever it was that scared us, and asked for the thing that we wanted. Maybe we were 5 and wanted a lollipop, or 7 and *dying* for a brand new Polly Pocket. Maybe we were in college, and finally mustered up the strength to walk up to our professor and say, “excuse me sire, but have you lost your mind???

(Haven’t done that… just a semblance of that.)

Do you remember how it felt when you got the thing you asked for? Do you remember the relief and the feeling of, “I’m not dead. I’m not DEAD!”? Because it was the best feeling in the world, and that feeling and positive feedback is what builds confidence.

So, go out and hunt for the projects and clients you want to work with. Gussy yourself up, and waltz right in front of them to (digitally) say: “Hi, I’m so and so and I’d love to work with you. Here’s why.”

And you know what? Some of those people will give you positive feedback, others will ghost, and others will say no. But those that give you that yes will make it all so, so worth it.

Plus, more yeses = more money in your pocket. Win, win, win.

Now, if you’re wondering how on earth you might “gussy yourself up and waltz in front of them,” try cold emailing. It’s how I launched my business, went full time in just 45 days, and how hundreds of other creative business owners are booking their dream clients to this day. 

Because you and I don’t work in corporate America and don’t have corporate-required trainings to attend with corporate-required sales roleplays, you’ll need to be taught how to cold email by, oh, say, a trusted and reliable source. 

Me. I mean me.

So, here are just a few of my cold emailing resources for you to read and try out!

3. Choose one thing or approach that scares you, and stick to it. 

When I was little, my mom said something that will always stick with me – “Never make decisions based on fear.”

Operating from a place of fear as a business owner is detrimental to your mental and fiscal health. No one can work from a place of flight for *that* long. It’s just not possible. 

So, choose one thing – a new marketing method, project, approach, or idea – try it, and stick to it. Stick to it even when you don’t want to, and even when you think you’re failing. (Because you’re probably not, you’re probably just around the riverbend from achieving something fabulous.)

Do you have to stick to it forever? No, of course not. But stick to it for a good amount of time, like for a quarter of the year. Regardless of if you fail or succeed, your skills will grow, and your confidence will follow.

Try to have fun, okay?

Nothing says “confident business owner” like trying and sometimes failing while still laughing as you go. We’re pretty blessed to run the businesses that we do – don’t lose sight of that.

Download my cold email template for free!