Leading Lady Podcast | Coaching and Accountability for Ambitious Women Entrepreneurs

What does it really take to create a cohesive, memorable brand experience at a live event? In this episode, I sit down with my dear friend and fellow Leading Lady Ambassador, Jennifer Osterhouse, to pull back the curtain on everything that went into creating the stunning marketing materials for our recent We Lead conference. Jennifer is a graphic designer with over 25 years of experience, and she's the creative genius ...

One of the most enriching experiences of life is creating strong relationships with the people that are important to us. That is why relationships are such a large focus of my work with many of my coaching clients. 

One fascinating tool that we often use for strengthening relationships is in regards to a person's response style.   

Tune in to learn what response style is, the types that people...

What truly makes a community thrive and last? In this episode, I'm diving into the heart of what it takes to build something that goes beyond connection and turns into legacy. I'll share how vision, collaboration, and belonging have shaped every step of my journey—from launching Leading Lady Coaching and The Annapolis Collective to creating spaces where women feel seen, supported, and empowered. Whether you're leading ...

Have you ever thought about how something as simple as buying flowers or adding color to your day could actually improve your leadership and wellbeing? In this episode, I'm diving into The Science of Whimsy — the intentional art of adding surprise, beauty, and delight into your daily life. I share a personal story about how a spontaneous bouquet of fall flowers shifted my entire mindset, and explore the real neuroscien...

Have you ever wondered what lessons you'd go back and teach your younger self in business? In this episode, I'm sharing ten truths I wish I had known earlier in my entrepreneurial journey and insights learned through both wins and hard lessons over the past 20+ years. From navigating criticism and burnout to building systems, setting boundaries, and separating your identity from your business, these are the real strate...

Have you ever noticed how the more you grow, the more criticism you seem to attract? In this episode of the Leading Lady Podcast, I dive into the connection between growth and criticism—why it happens, how it impacts us as leaders, and what we can do to navigate it with resilience and confidence. I open up about my own experiences as a business owner, from handling personal attacks and misconceptions to reframing criti...

I have been in business for a long time now. One thing that I learned early on in my business journey is the importance of having a professional help you with your accounting and taxes. 

There are so many things that we have to handle and worry about as entrepreneurs. If there is one thing that is important enough to outsource and get help, this is it. 

In this episode, I am chatting with ...

Have you been dreaming of writing a book and becoming a published author? Every year, this is consistently one of the most popular goals that people set.

So what does it take to move forward on your dream and make it happen? In today's episode, I had the pleasure of interviewing a leading lady who knows just how to do that.

Jennifer Klepper is the author of Unbroken Threads, a debut novel that...

When we feel frustrated or angry, it is human nature to want to "vent" and share our challenges with others. It helps us feel less alone in our trials and relieve some stress, but is it always helpful? 

In this episode, I share my perspective about "venting" conversations and when they are helpful and when they become simply gossip. 

After listening in, I hope that you will pause and think abo...

A  few weeks in Europe have left me with a lot to say! From travel hiccups to business surprises back home, to the emotional revelations I felt while vacationing with my son.

I'm excited to be home and to reflect on what this time has meant to me. We can learn a lot when we're taken out of our regular day-to-day lives for a while.

In this episode, I'm sharing a few of the lessons I learned...

How do you show up in the world? 

I have worked in the education realm for over 20 years and something that we teachers absolutely love is acronyms! We have one for everything.

In this episode of Leading Lady, I am going to be sharing with you one of my favorite acronyms ever because it has helped me so much and I really think it will help you too. I have used it daily for the last several...

What does it take to be a leader? 

If you have been following me for a while, you know that I always say "take the lead, and the rest will follow." If you have air in your lungs, you are a leader. But how do you take the lead in your life? 

In this episode of Leading Lady, I am breaking down the word LEADER, and how I use that word in many areas of my coaching. 

In my busine...

Today we're hearing from the next generation of leaders, our Leading Lady interns!

I'm joined by the amazing interns who have been working with us this summer at Leading Lady, Makaylah, Grace, and Scarlett. I am passionate about mentorship, growth, and leadership, and am excited for you to hear about their experiences.

In this episode, the interns share what they've been up to and what the...

Have you ever found yourself judging a business without considering the human behind it? In this deeply honest solo episode, I open up about a moment that rattled me—a toxic online post about another female founder—and how it unexpectedly struck a nerve. I reflect on the reality of leading a community, the courage it takes to put yourself out there, and the vulnerability that comes with being the face of your brand. Wh...

How do you walk away from diet culture when it's all around you?

It's not an easy task, but it's so worthwhile for your long-term health and happiness. I sat down with Elizabeth Harris to talk about how to break the toxic cycle of comparison, negative self-talk, and perfectionism that shows up in food, body image, and leadership. It's a heavy topic, but there's so much joy to be found on the other side o...

Let's take a moment to celebrate you. 

In this powerful replay episode, I encourage you to take a moment to look back and see how far you've come so far. I'm going to invite you to take inventory of all the amazing things you've achieved and celebrate all your hard work. 

I recently experienced a moment, which you'll hear about in this episode, that caused me to pause and notice what an in...

When you are building a new business and marketing yourself, you will be networking with other business owners quite frequently. In these encounters, it is so important to present yourself as professional and prepared. 

In this episode of the Leading Lady Podcast, I discuss a business call that I had and how it left me feeling sour and disappointed. I share this conversation not to rant, but to share an ...

Are you constantly asking yourself things like: am I doing enough? Am I showing up? Am I delivering on what I said I wanted to deliver? Are people happy with my work?

Like many other high-achieving women, you're facing the anxiety that comes from striving for perfection. It can be easy to get stuck in that place, but there are things you can do to recenter yourself and squash those feelings that are hold...

In this Fan Favorite Replay episode, I'm revisiting a time I started a Monday morning by reading a very mean-spirited and hurtful email. It left me feeling upset and slighted, and I had to work really hard to find the positive in that experience. 

I chat about this experience, what I did to turn it into an opportunity for growth, and my suggestions for how YOU can do the same. 

Looking bac...