Bold Women - Caitlin Judd

Bold Women - Caitlin Judd

Over the years Caitlin Judd has admitted to an impressive track record of business ideas, some thriving, some not so much. But what Caitlin has done, is grasp the power of conversation, and the importance of lifting and inspiring women around her. Starting out as a monthly-invite only supper club in Melbourne for like-minded women driven by ambitions – she moved those conversations into a more public forum. Cue, the launch of lady-brains podcast, a celebration of female founders, Caitlin digs deep with her guest speakers, asking hard-hitting business questions, that ultimately turn into gospel advice for her avid listeners.

When I asked Caitlin on her biggest belief, her response was simple.

Celebrating women in business, leadership and entrepreneurial settings has to come from the power of connection and conversation – it is here that we see the real magic happen.”

Recently, I sat down with Caitlin to talk about her BOLD story, a moment where we delve into the power of collaboration, expression, and the key lessons she has learnt along the way.

Firstly, thank you for your time. I want to jump straight into your world. So, if I said the sentence, “She lived a bold life”, what does that mean for you?

She’s living a life that’s unapologetically hers! She’s curious, intelligent, open, brave and doesn’t shy away from taking calculated risks. When she rises, others rise with her. She wants to show others that they too can live a life on their own terms. She’s not afraid to fail, because she knows that when she does, she’s learning and growing. She challenges convention and the status quo. She doesn’t worry too much about what society says about how she should live her life. Rather, she leans into what gives her purpose and joy. She’s cheeky, she’s magnetic and she’s graceful.

Do you see yourself as a bold person?

I’m growing into the bold human I want to be. I never used to identify as someone who lived boldly, but only now, do I see that I am becoming her. Every day I have an opportunity to live more boldly by taking more chances and hoping they pay off.

I think I used to conflate ‘boldness’ and ‘brashness’ into a single meaning, or the need to be brash to live the life I desire. But what I’ve come to realise is that you can be bold, simply by being brave, and to be brave, is to honour your truth.

Whether or not you see yourself as bold, we certainly do. What does it take to show up like that?

I believe that to show up boldly requires a great deal of courage, and to be courageous, you need to be vulnerable and compassionate. It can be scary being vulnerable. But wearing your heart on your sleeve and sharing your jagged edged gets easier over time. As the brilliant Brené Brown says, “Vulnerability is not weakness; it’s our greatest measure of courage.”

Speaking of being bold, what is the boldest move you have ever made?

Living my truth is probably the boldest move I’ve made. It’s led me to back myself for most of my life, even in those moments of worry, regret, and resignation. And there’s been plenty of those moments!

On that, what do you think stops people from living an unapologetic life, or making bold choices?

This is a great question and one I’ve been pondering lately. I think there’s a few reasons why people, particularly women, hold themselves back from living an unapologetic and truly authentic life.

Firstly, in living that way, you’re affirming that I am worthy of this life, I deserve everything I am working towards and want for me. That can be a scary admission. Especially if you’ve grown up believing that to be untrue, or if you’re a woman, encouraged to serve everyone else first. Living a life on your own terms often means sacrifice and disappointing others. But at what cost are you willing to give up the life you desire?

Secondly, you can’t live a bold and unapologetic life if you’re not expressing who you are. As I mentioned earlier, that takes vulnerability and courage. It doesn’t mean you have to share everything with everyone, in fact I’d argue the opposite. It simply means you need to get to the core of who you are, what you desire, and why you’re on this earth. Many people ignore the bold flashing signs, or they resist the opportunity to inquire and discover what it is that lights them up.

And thirdly, you must have agency. Once you believe you’re worthy of living the life you deserve, and you’re showing up as your true self, then you need to take action! Even if it’s just one small step each day to get you closer to living a more bold and brave life. It won’t happen overnight (there’s no such thing as an overnight success), but you can turn your life, career, or business goals into a reality by building out a pathway. Don’t forget to savour and celebrate along the way.

As a thought leader in your own right, how do create a story, one that takes people on a journey with you?

When sharing a story, there’s usually three components that make it sparkly. There’s the overall narrative, the stats and facts that support the narrative, and then there’s the meaning, or emotional response you have to the story and how it affected you and others. When you can deliver all three of those components succinctly, you’re onto a winner.

The feedback we often receive from our podcast listeners is that the story we shared inspired them, made them feel less alone or as if they weren’t the only one making mistakes in business, and that it was super practical in the way they could apply the lessons they were learning. When a founder can see themselves in the stories we share, that’s when it resonates the most.

With one of the most top-rated business podcasts in the market ‘lady-brains’, could you please tell me about the idea and how it came about?

We need to go back many moons ago, to 2017. We created a monthly invite-only supper-club dinner series for like-minded women who were starting their own brands or had ambitions to. We quickly realised the power of connection and conversation, and knew it had to be shared more broadly, and just like that, the podcast was born. We’ve told some extraordinary stories on the podcast, from the likes of MECCA’s Jo Horgan, artist CJ Hendry, Kim Teo from Mr Yum, Sarah Munro from Sarah & Sebastian and Margot and Maria from The OneTwo - On top of the podcast we mentor, coach, facilitate workshops and invest in women founders.

Interviewing over 100 female founders, what has been the key lessons these entrepreneurs have taught you?

There have been so many takeaways from our interviews over the years, but one that comes up time and time again, is surround yourself with great people. Not only at work, but also in your personal life. You experience so many ups and downs as a founder, and you need to have good mentors, coaches, family, and friends that you can rely on and offer you a shoulder to cry on.

Do you think to live boldly, you should share your mistakes, as much as your wins?

Absolutely. Again, you don’t have to share every single detail, but it’s humanising and humbling when you can admit you’ve stumbled or fallen. Making mistakes or failing is typically a sign of success. When you can make a mistake, learn from it, and take the next best action, that’s the ultimate mindset and approach. Would it be weird to say I hope to make more mistakes this year?! It will be a sign that I’ve pushed myself to the next level.

Lastly, what’s next for you, and what’s next for lady-brains?

I’m at a stage in my life where I am making more considered choices about what I want, where I want to be and who I want to spend my time with. It’s exciting and daunting, but I think it’s important to assess all areas of your life regularly and see what needs to stop, change, or remain the same. I love the community I have built in Sydney, and I am looking forward to travelling more, exploring other business ideas I have, and tapping into my creativity, be it drawing, painting, or writing.

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