How Did She Get So Confident?

Catherine Cassidy (Business Heroine Magazine)

Recently, I was asked: “How did you get to be so confident?”

The question startled me as bit as I’d never thought about it that way. It just is. I am confident. But it was also thought-provoking.

Good question. How DID I become as confident in myself as I am now?

Because I certainly wasn’t always this confident. Also, it’s a different kind of confidence. It’s grounded in purpose and centered in me being happy with ME. Just as I am.

So, how did I get here?

Certainly, it’s been a journey.

It’s only in looking back that I can see how I’ve been working on cultivating my own confidence (or, as I like to call it, Style Power), since a very young age.

I’ve always come across as confident. Even from a young age I would receive compliments from adults specifically on my confidence. But they didn’t see my inner turmoil. I sometimes accepted these compliments and sometimes pushed them off.

They didn’t see my shyness. I moved through it on almost a daily basis. And still do sometimes.

This journey has been a  somewhat subconscious one. I didn’t realize how certain life events helped me gain a little bit more confidence in myself, even if they were hard or hurtful at the time. So, I’m so grateful that this inquiry made me look back at what has helped me move through my discomfort, shyness, body shame and perfectionism that had been taking little digs at my confidence on a daily basis.

So now I can share it with you, for wherever you are on your journey in confidence and complete self-acceptance of your awesomeness.


Create a Power Posse

Like many women, unfortunately, I ran into a few mean girls throughout my schooling (and even a little bit in the corporate world). The first time, I went through therapy. The second, was completely devastating, but I moved through on my own. The third pissed me off. The fourth motivated me to start my business.

I can’t ever really know the true reasoning for their actions, but I can know that it wasn’t really anything to do with MY actions. I was, and still am, puppy dog loyal to my friends. So, while heartbreaking, these situations made me really look at my decisions in my friends. Why did I want to be friends with them? Because they were cool or because they had my back?

My awareness that was created through these experiences made me SUPER picky in who I bring into my inner circle. I’m fortunate to have a lot of great friends and I can very literally say that don’t have any catty girlfriends because I have a pretty low tolerance of that kind of attitude. My friends know that I’ll call them out on their sh*% but I also appreciate when they call me out on mine.

I grow because of our friendship. They know they can call and I’ll be there for them. Yes, just like that James Taylor song that happens to be a favorite.

Neither my business nor I would be here now if not for the Power Posse of amazing women I’ve collected over the years (and continue to collect). They’ve spent time brainstorming marketing & business development opportunities, introduced me to amazing new friends and clients, and been there to talk me off the ledge of threatening to quit the business and get a job. They believe in me even when I haven’t believed in myself. Which is why I DO now believe in myself. And so I hold the same space for them.

If you’ve only got nice things to say and you’re driven to make an impact. . .come sit by me! I’ll do whatever I can to help you grow and evolve as well!


Play with Clothes + Dress Your Body

Again like many women, I’ve struggled with accepting my body.

I wonder if you can relate to looking at a picture of yourself and saying to yourself: “oh my gosh, I was so skinny! How did I think I was fat?” Oh, by the way, I was looking at a picture of 13-year-old me. Or, worrying about the fact that I gained enough weight at summer camp to cross over the 100 lb. mark at 10 years old. Or being happy that I lost 10 pounds from having a horrible bout of flu for 7 days as a college Freshman. . .I finally felt skinny.

Gross. It worries me that this is still quite common among young girls.

Loving my body as it is has been the hardest part of my confidence process. As such, it’s probably been the biggest part of my catalyst in confidence.

Being able to dress my body no matter whether I lose, gain or maintain my weight has been integral in this part of the process. Ignoring the trends and focusing on what feels good for ME has been key as well. Most trends (ahem, harem pants!) just don’t work for my curves. Classic & tailored is what I need. And it’s ME.

This is why I now always FEEL solid, strong, healthy and confident in myself and my presence, whatever my weight.

I don’t know if I can put enough emphasis on this element as it can be a HUGE piece of cultivating confidence for most women. 


Embrace Failure

There is a reason why the Friends scene with the couch is one of my FAVORITES of all time. And anytime someone says pivot, I hear ‘Pi-VOT’ in my head.

Because that’s life.

Constantly re-routing you to be on your best path. Even if the path is currently rocky and rough, it’s for a reason. As they say, it’s not failure, it’s feedback. Not that it makes it any easier in the moment. And it’s only in looking back that it all makes sense.

Such as the heartbreak of not getting into Stanford when it has been your lifelong dream. Instead, you do get into a great college and business program which, unbeknownst to you, has one of the TOP entrepreneurship programs in the country. This decision to go to USC, a school that clearly really wanted me, ended up being one of the best decisions of my life and truly a catalyst for my success and confidence.

It took me a LONG time to build Ustyled up to a sustainable business. The first couple of years were tough. . .like could have been on food stamps tough. Determined to figure it out and give myself the space, I found a few side jobs until I settled on a part time job that played to my strengths and really complimented and supported what I was creating in Ustyled. Three years ago, with the launch of Boutique Box, I had a sustainable business.

Boutique Box was a pivot that made Ustyled finally a successful business. came from the fact that women weren’t understanding the value in outsourcing their personal shopping to save time and ultimately make more money. So, I created a way that made it as cost effective as time efficient to invest in support.

Of course, even my failed relationships – whether romantic or friendship – have given me so much feedback that created clarity to invite the right people into my life. Hence, no catty girlfriends, just a supportive power posse. I am so grateful for these ‘failures.’


Get Comfortable Being Uncomfortable

Growing up, I was incredibly shy. I’d so much rather curl up with a book or hang with the adults than be put in a room with a lot of highly active kids. The experiences with mean girls didn’t feel like they helped with this at the time, but they ultimately forced me to get comfortable being uncomfortable if I was going to make friends.

That’s why I was ultimately able to go to USC without knowing a soul as a freshman and make lifelong friends right off the bat. And why I was able to move to Washington, D.C. and quickly create a power posse of amazing people.

Naturally, I wasn’t comfortable with public speaking, either. It is something I’ve pushed myself to do because I knew that’s how the my message would only get out there in a bigger way through speaking to large groups.

At one point early in my corporate career, I took a business plan course with my best friend to look into developing an idea we had together. The first class, we had to go up and introduce ourselves to a room full of strangers. My voice audibly shook when it was my turn. My BBF looked at me shocked as she could hear the trembling in my voice. Up to that point, she had only seen me as completely confident and clear.

Now, I love speaking to groups! I’m still nervous before each engagement, but that’s because I care that much about connecting with the audience so it actually helps me to ensure that we DO connect.

Having a business is the ultimate lesson in getting comfortable being uncomfortable, which is why I’ll be ever grateful for every trial and triumph. Growth is definitely outside of your comfort zone. The first few years I was uncomfortable with selling and constantly uncomfortable as I wasn’t bringing in that much money. The next few years I was stepping out in a bigger way and uncomfortable being visible. This last year and 2016, I’ve been uncomfortable as I invest in expansion and take big leaps of faith (guided by logic mixed with intuition).

And that’s why my business keeps growing. With my investments in the business, myself, my home and my team, I freak out a little bit on the inside every single time. But the beautiful thing is that the business grows to cover it all EVERY TIME. (To reiterate: I’m taking very calculated risks, not throwing money at problems on a hope and a prayer.) NONE of it is easy, but it’s definitely FUN!

(Disclaimer: While it’s been the most amazing learning experience for me, having a business is NOT for the faint of heart. It takes resilience, hustle, unwavering commitment, passion and SALES.)


Be Okay With Being Alone

I truly believe that what doesn’t kill you makes you stronger, which is why Kelly Clarkson’s “Stronger” was my anthem as I moved through my last big breakup. (As was Taylor Swift’s “Never Ever Getting Back Together”, but that’s a different part of the story. ;))

The reality of my last breakup is that much of it I moved through on my own. I saw my friends and they were incredibly supportive, but they were also going through their own things. Sundays were the loneliest. So, I’d hike, read, write, and DIG IN to what I was feeling and WHY I felt that way. (I also binge watched Friday Night Lights and White Collar. I would highly recommend that RX.)

While it was hard at the time, now I’m so grateful, because it made me really okay with being alone. In fact, it made me really relish being alone, especially as my schedule is as packed as ever!

That’s my story. These are the keys to how I’ve cultivated MY confidence. I’d love to hear YOUR tips and experiences. We’re all here to support each other. Collaboration is key for women advancing as leaders and I’m absolutely here to support you in that way!


Catherine Cassidy (Business Heroine Magazine)

Business Heroine Magazine

We’d love to hear from YOU…

What are your tricks for feeling confident? Were you always a confident person, or did you have to consciously cultivate your confidence? Leave your answer in the comments below! 



, , , , , , , ,

No comments yet.

Leave a Reply

Leave your opinion here. Please be nice. Your Email address will be kept private.
We like you! Do you like us?