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How Confident Are You? How to Build Self-Confidence


Low self-confidence. Do you ever suffer from this?

Unfortunately, I have. I’m not proud of it, but it’s the truth.

While filling out an application for a mentorship program, I realized that low-confidence has been a constant theme in my life – from my preteen years to adulthood.

As life does, my confidence levels have moved in waves – moments of strength followed by moments of intense insecurity.

It’s important to manage this – to understand how high or low our level of self-confidence is because without it, we can’t make progress. We can’t make an impact, we can’t be a voice, we can’t be much of anything. Without it there’s a crack in our foundation.

That’s why this week I was so excited to interview Catherine Cassidy, Founder of Ustyled.

Her work speaks to me personally because her mission – to empower women to stand out as individuals through style – drives not only her company’s success but also the change we need to see in female leadership.

I’m extremely grateful to Catherine for her work, so without further ado…meet Catherine Cassidy, and learn how you can build your self-confidence to be a better leader.


Give us some background. Where are you from, and where did you grow up?

I was born in Los Angeles, CA but was raised between the suburbs of Detroit and Chicago.

I went back to L.A. for undergrad at USC. I have some of the liberal, open-mindedness of L.A. as well as the down to earth, grounded values of the Midwest. I chose USC to immerse myself in more diversity than I experienced growing up in the suburbs.

I love being exposed to people with different backgrounds and opinions because that helps me to expand personally and professionally.

You founded Ustyled at 25. Tell us about your mission, the work you want to do?

I believe that style is a catalyst for confidence. And I want to see you own your presence and power completely – in your life, love and career.

I also want to see more women rise up as leaders, and confidence is a key aspect to having the courage to speak up, stand out and be seen … even with as far as we’ve come in the last 20+ years for women in the workforce and in politics, we’re still coming up against a double standard.

The more we stand out individually, the easier it becomes for the next woman to have the courage and before you know it, we have the change we need to see in the world.

Did you struggle to identify the work you’re doing now?

It’s been an evolution for Ustyled, just as every woman’s career is an evolution. 

Right out of college, I certainly didn’t have a mission. I was excited to learn and grow and contribute while finally having spending money and a budget!

But while I loved my job as a merchandiser, I started questioning the meaning behind what I was doing – it wasn’t fulfilling. I felt as if we were simply making clothes that weren’t adding value to our customer’s closets (most sold at markdown), and they weren’t actually helping anyone.

It took me a good year and a half of soul searching and long hikes through the hills of L.A. to come to the conclusion that I needed to start a business. I wanted to guide women on what to wear and where to find to dress confidently and authentically as professional women, and doing so without having a giant closet or experiencing the frustrations that come with shopping and building a wardrobe.

What led you there? Can you recall any experiences you had that pushed you to your mission?

When I started Ustyled at 25, it was about making it easier for women to stay in the workforce. Over the years, I realized it was deeper than that. It became about empowering women to rise up as leaders. Part of that is making it easier for them to stand out, helping them to know how to show up as 100 percent themselves while being taken seriously for their skills and intellect. The other part of that is simply making it easier – taking something off their plate. 

You just have to start with where you’re at now because it’s inevitable that it will evolve and when you look back … it’ll all make complete sense even if you’re completely confused in the present moment.

What has been the result of doing mission-driven work?

I love what I do.

There are nights I go to bed questioning what I’m doing, and why I’m still working so hard, and there are mornings when I wake up with complete anxiety because ‘oh my gosh, how am I going to do x, y, and z by this date?’

But, ultimately I have a session with a client or speak to a group of young women or experience a breakthrough ‘a-ha’ moment and it’s like ‘oh this, this is why I keep putting one foot it front of the other.’

I can see the immediate results of the work we do. I’m still pretty front-line, so I get to hear the feedback in the confidence that our clients feel, the clarity they create and the SUCCESSES they start having – personally, professionally and romantically. It is FUN.

So, I work hard, and I work a lot, but it also doesn’t always feel like work. (Especially as I’ve been able to build a support team!)

What’s the biggest challenge you face, especially when it comes to doing mission-driven work.  How do you overcome it?

Sometimes the financial success and security doesn’t come right away. The hardest part of this is realizing that if you’re struggling financially, that doesn’t make you a failure. Ultimately, it makes you resilient.

The SBA doesn’t publish how long it takes businesses to get into the black on purpose. They don’t want to hinder entrepreneurship. However, it does take 3-5 years for most businesses to show a profit, even service based businesses. It takes time to build visibility, a following, a message, etc. And it takes testing and tweaking to understand what your customers want and need – even if you’re incredibly talented and bright. It’s not about talent, it’s not about a business brain, it’s about creating a value proposition and marketing it to reach the people you can serve.

So, don’t stress about the money. Use this challenge as a tool and feedback. If it’s not selling, you’re missing something. It’s not about the service, it’s about the message and delivery.

Also, get a part-time job!

MANY businesses (mine included) were started part-time and it’s 100 percent how I would suggest starting a business for exactly the reasons I stated – you have a great idea, it meets a need, but you have to understand how to communicate the value of it to your target market and that can take time (patience) and money.

What advice do you have for 20 to 30-somethings who want to step into leadership roles but need to build self confidence? 

I actually wrote a blog post on this early in 2016 when someone I was just starting to date asked me: “How did you get to be so confident?”
For some reason, it caught me off guard, yet it’s a question I’ve gotten most of my life and it’s always kind of baffled me as to why they would ask me that. Can’t they see how insecure and doubtful I am on the inside? I guess not!
Clarity of WHO you are, how you want to show up, what you want to create in this world, who you want to spend your time with and your individual talents. Conviction in yourself — not caring what other people think and committed to taking every step forward in integrity to your values, your purpose and your WHY.

How do you do that – find clarity and have conviction?

I would survey your loved ones and close friends. Ask them what they appreciate about you. Often, we’re not even aware of our own special sauce because it comes so innately to us. Yet, as you recognize it and start noticing the effects of how YOU do things specifically, you’ll build your confidence up over time.

It’s also recognizing that it’s not a quick fix. Cultivating confidence is a constant journey. Beating self-doubt as you take yourself past your comfort zone takes a lot of resilience (and a support team!). Then, as you find success with these moves outside your comfort zone, your confidence muscle gets stronger. And so it continues.

Confidence comes in doing the work — showing up to dig into your fears, your pains and your dreams. Too many of us want the immediate results. Even in our work with clients, we can get an immediate external result since we’re working with clothes and a visual element, but I promise you that we have to keep digging in with our clients as we move them through their evolution of style and confidence.
Have you struggled with low self-confidence? What do you do to push through it? Share your thoughts and questions in the comments below. 
Belma McCaffrey

Author Belma McCaffrey

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Join the discussion 2 Comments

  • Abby says:

    Belma, what really got my attention was her response to the question “How do you do that – find clarity and have conviction?” Because this is one of the exercises we’re going through and it was one that was a little scary for me. I’m use to getting feedback from bosses at work, not loved ones and close friends. And I have to admit that it’s insightful! There’s things I know about myself but I didn’t think they’re the first thing that come to someone’s mind when they think about my strengths, so it’s kinda nice.

    • Belma McCaffrey says:

      Thanks so much Abby! Yes agree it’s so helpful to hear other’s perspectives. This may resonate with you too… It’s important to be open to others’ feedback while also filtering it/keeping in mind it’s feedback. Maybe that takes the pressure off/eases the fear when doing this type of exercise.

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