Becoming Her: The Braver, Bolder You

Is it really too late to start something new? Not even close.

In this solo episode, I’m sharing what I’ve learned from starting over—at 40, at 59, and now—and why age brings not only wisdom but boldness. If you’ve been feeling a spark, a nudge, or a tug toward something new, this is your reminder: it’s not too late. It might just be right on time.

In this episode, you’ll hear:

• How I shifted from corporate to wine tastings… and again into podcasting
• Why our dreams aren’t random—they’re guidance
• The Be – Do – Have framework and how it helps you create the life you want
• Why messy, imperfect action beats waiting for clarity
• What it means to move forward with your future self leading the way

If you're ready to step into the next chapter—even if you're scared—this one’s for you.

Want some journal prompts to get started?
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Transcript

Becoming Her: The Bolder, Braver You

​  [00:00:00] 

Penny Fitzgerald: If you've ever thought, it's too late for me, this one's for you. Maybe you've been sitting on a dream for years or maybe there's a little nudge, just a little whisper that keeps tugging at you. What if I told you that spark isn't random, that it's a true message, that it's a message from your future wiser self who already knows you've got what it takes.

It's not too [00:01:00] late. In fact, it might just be right on time. First, let's bust that myth of too late. A lot of you know me from my wine tasting days when I did in-home wine tastings and led a team in doing the same. What you may not know is that I started that job at the age of 40. At the time, I thought, wow, I'm completely pivoting away from my corporate career.

I was choosing not to find another job in product fulfillment, sales support, or warehousing. I was stepping into a whole new industry at age 40. I built my wine tasting team and business to one of the top three in the country over the course of the next 18 years. Then when that business model of the, then, when the business model of the company switched to affiliate only, I was 59.

And I thought, what am I gonna do now? I certainly didn't intend to go back into a corporate role, and I wasn't at all excited about the prospect of building someone else's empire at the risk of my [00:02:00] own again. So I began to analyze what did I miss the most about that? What was I really good at? And how did I help other people?

I had started a podcast to tell women's stories and lift others up, and I had this very tiny glimmer that maybe this will lead to something more, another complete change. And this time at age 59, what I didn't realize in the thick of that moment was that I really wasn't starting over. I was building on all my past experiences and knowledge and becoming wise.

I finally can see that all of my life's experiences, the good, the bad, and also the ugly, have prepared me to fulfill my purpose and serve others, to lift women and encourage them to follow their dreams as I follow mine. All these experiences shape who we are, how we move through the world, and we have a choice on how we use that wisdom.

Many women and men [00:03:00] too started their greatest career or the thing that lights them up. And the world Later in life, many women and men too start started their greatest career or the thing that lights them up, and also the world later in life. Mary Kay was 45 when she started Mary Kay Cosmetics, and after catering out of her kitchen, Martha Stewart launched Martha Stewart living at the age of 49.

Louise Hay started Hay House in her sixties. What do women of a certain age have in common? Along with being a whole lot wiser? Frankly, we're less likely to give a about what others think, and I mean that in the most positive way. We are more brave than ever and we allow ourselves a space to be seen and heard.

When we set our mind to something, we are less likely to be deterred. As we grow older and want into our wiser selves, it's a perfect time to dream big. What would we do? What could we do and what do we want? What drives us absolutely bonkers? And what idea do we have to fix that? [00:04:00] What places do we wanna go, things?

Do we wanna see experiences? Do we wanna have? Who do we wanna help and who do we wanna hang out with? Who do we want to be? Those dreams, those thoughts, they aren't just random. They're guidance from our future. Guidance from our future wiser self. You've probably heard me say before, there are no questions without answers, and no problems without solutions.

Well, there are also no dreams without the wherewithal to achieve them. Deep down inside, we know that those dreams were placed there because there are memories of things we've already seen, things we have the ability to achieve and enjoy. They're the vision of what your soul is showing you as possible, what your future self is inviting you to walk toward and enjoy.

I truly believe that if you have a dream on your heart, it's because your higher [00:05:00] self has already lived it. You are just catching up. If you've worked with me, you've most likely heard me talk about the be do, have framework, and you may have heard it from other coaches and teachers as well. Essentially, you need to be the version of yourself that already is living the dream first, how does that person, how does she move through the world?

What does she tolerate? What's her routine? This moves you into doing the things that she would do? What's her day like? What tasks does she complete? What does she delegate? If she has the freedom to travel with family and friends, I. Is she encumbered by the task of creating the itinerary and checking prices for every flight for everyone on three different departure dates?

You know, just in case there's a better option, is she delegating some tasks and instead using her gifts and passions to create a better [00:06:00] life for the people she serves? Would she hesitate about hitting share on the post because she's unsure of how she'll look? Or will she use her voice to lift others not worrying about those who don't share her vision, and especially not worrying about those who aren't doing the thing as she focuses on the task, uh, as she focuses on the tasks that use her gifts and serve her people the most, she moves toward the future where she has her dreams in her hands.

The next time you hesitate, ask yourself, what would the wiser version of me do? The one who already launched the podcast, the one who already filled the retreat, the one who already showed up, even scared. Then do the thing. Is this always gonna feel good? Nope. Will you doubt yourself at times? Absolutely.

Will there be, will there be haters and trolls? Um, yes. And guess what? Sometimes you'll hit share and [00:07:00] realize you messed up the language or accidentally shared it to the wrong group or intended something completely different. And sometimes, sometimes those will be happy accidents that lead to a greater good in spite of your fears and messiness.

It's okay not to be perfect. It's okay to be messy. You've heard it a million times. Babies don't just come out of the womb and run. You know the first time you've done anything, it didn't turn out perfectly. This is no exception. In fact, as you begin, you will suck. You may suck for a very good long while, but with practice and getting brave, the better you'll get.

And you'll grow. As long as you let your future self guide you and keep the people you serve in mind, you'll make progress perfectly am perfect progress. And as you take that first step, the next step will become clear. And the step after that, [00:08:00] it's a process. You can't plan it. I'm sorry. To my organizational and planning Queens respect we're sisters.

It's uncomfortable for those of us who like to get our ducks in a row before we take action. Remember, that's just our brains trying to keep us safe and in our comfort zones. The magic and the growth lies outside of that. Yeah, trust that when you take that first step, the next will become clear and remember that you can and need to pivot as you grow.

The thing you thought would be well received, it may bomb. Have you ever posted on social media and thought, oh, this is gold. People are gonna love this. I love this. Only to have very little traction or crickets and then some stupid little thing that's outta nowhere. It gets all the engagement. Yeah, same.

Remember, we don't control it all, and I'm sorry. Again, my control freak sisters, I feel you. Say it [00:09:00] with me. I can plan, I can prepare and pour my heart into it and still release the outcome. That's none of our business. Come back to that line. Whenever you start gripping too tightly, let it be your refrain.

Keep serving your people, using your gifts and following your passion. Imperfect action is still action and way better than wondering if or what will work. Try it. Just take that first step and then the next, so what have you been dreaming? Have you been dreaming? If not, go to your happy place and start.

What have you been putting off? Is there something that you look back on and think, wow, that would've been fun? Is there something your girlfriends know you're amazing for but you've forgotten? DM me the word, go on Instagram and my handle is @penny4yourshots. That's with the number four Penny for your Shots, and I'll send you some journal prompts to get you thinking.[00:10:00] 

I'm here to talk if you wanna noodle some things together. And if you'd like to explore ways to work together and discover or rediscover what lights you up, visit my website, pennyforyourshots.com/about. Or if you just wanna get inspired every week, get the occasional cocktail recipe, or here's some positive vibes, become a Penny for your Shots.

Insider, uh, that again is at my website as well, pennyforyourshots.com/insider. Remember that your dreams didn't expire with your thirties or your forties, or even your fifties or your last job. You are allowed to start over, pivot or chase something new right now or whenever, and your future self.

She's already clapping. Talk soon, sister. Cheers.[00:11:00]