Alright – so today we’ve got the honor of introducing you to Stephanie Webb. We think you’ll enjoy our conversation, we’ve shared it below.
Hi Stephanie, thanks for joining us today. We’ve love to hear an interesting investment story – what was one of the best or worst investments you’ve made? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)
I have a plethora of worst investment stories as I have a tendency to act first and think later. I do give myself grace for those because I was doing the best I could with who I was at the time and I was always interested in trying new things and bettering myself. I think that’s important for people to recognize. Even while we are dealing with the consequences of those choices, we also must find space for grace.
I also have many best investment stories and the one I’d like to focus on is when I invested in my certification to become a coach and speaker. In 2016, I was working at a financial institution and I felt stuck. I had been studying philosophy at university but due to financial constraints and my work schedule, I wasn’t able to continue. I saw an advertisement to team up with leaders and teachers associated with John Maxwell, who is the #1 leadership expert. I had a few of his books and always admired what he taught. It took me time to think about it because it was a lot of money and I didn’t want to add more debt but I also saw it as an investment and an opportunity.
Working all day in the office at a computer, I had no energy when I came home. I had all these online courses available to me but lacked the capacity to focus on any of them. But that year there was a conference in Florida and I decided to attend. It was such a wonderful opportunity to meet other like-minded people, be in the midst of incredible positive energy and to learn from great teachers. It was a whirlwind of a week and I didn’t want it to end. But the most impactful thing that I gained was recognizing how I could move forward in my own personal growth. This is what I longed for so much but I needed some guidance.
It was also at this conference where I recognized that we all have something wonderful to offer. Growing up, I always felt lost in the crowd. I didn’t know I had much worth or that there was anything of substance I could add to this world.
I gained that awareness but it still took me about 8 more years for my body and heart to catch up with my brain. This was when I started to actually believe that I could add value to this world. Over the years I tried a variety of jobs and careers as I kept trying to figure out what I was meant for. Until finally in 2024, I knew I was ready to start being a mentor. I do not mentor or coach from any specific program or teacher because there is no one way to grow. Everyone learns and receives in their own way. I gently help people to find their own path and I find it helps to share my own experiences because it is relatable and it helps people know they aren’t alone. But signing up with the John Maxwell team was that first step in helping me see my own worth and know that I could move forward in growth.
Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
As an Encouragement & Empowerment Mentor, I am here to hold space through active listening, gently guiding to help see new perspectives and challenge limiting beliefs, providing both empathy for things that are hard and hope for new beginnings. I’m available for anyone to book just an hour if they really need someone to talk with and I can work with people longer if they’d like someone to walk alongside them in their healing. Two of my main focuses are on helping HSPs (Highly Sensitive People) navigate the world with their sensitivities as well as be there for people deconstructing and leaving fear-based, shame-based, and authoritarian faith.
I am a Podcast Host/Producer/Editor of the StephUp Podcast, which I have been doing since 2020. I have conversations with people who share their own experiences, expertise and wisdom for healing and growth. I started podcasting when I was studying to be a VoiceOver Actor and it has been so much fun and I love connecting with people. I tell people it feels like free life coaching all the time. Uplifting conversations are incredibly healing.
I am also a writer and in 2021, I self-published a children’s book named “What Should Dragon Do?”, that teaches kindness and emotional intelligence and resiliency to children. Adults also need this book because many times we need to learn it for the first time or we need constant reminders. I’m currently working on a book about a chipmunk who learns new things on an unexpected adventure. I’m also a contributing writer for the DWC Magazine, where I write about relationships, personal growth, communication and learning to love ourselves and love others.
How did you build your audience on social media?
I’m still building my audience on social media and I am starting to see my numbers climb. Being on many of the platforms (TikTok, Facebook, Instagram, YouTube), I’m still figuring out if I should focus on one or two or keep them all. It is fun to just post on different ones and play around with it.
My advice is to just have fun. Play. Show up. When inspiration hits, don’t overthink it. I have done reels or posts where I spent so much time creating and editing and writing and finding the right hashtags and file names and captions for the post. Many times, those don’t get the numbers I think they will. Of course, keep working on doing the best you can and taking that time. But I’ve noticed (and I’ve heard it from others as well), that it is when you really feel led to share something and it just flows, no matter if your hair is a mess or it isn’t perfect, that’s when people connect and you gain traction. People can sense your energy and authenticity. Keep growing and keep being you. The world doesn’t need more of anyone else. It needs you and your spirit and your energy.
Have you ever had to pivot?
I have been pivoting different changes and careers since my 20s. But in the past 5 years, it has been continuous pivoting and learning resiliency.
I lived with anxiety and depression for most of my life and I broke down a lot. Due to being highly sensitive, not knowing I had religious and emotional trauma, I struggled and was in survival mode for almost 40 years. And when I had to leave my job at the financial institution at age 40, I was scared.
I have tried and worked at so many different things: legal assistant, voiceover artist, administrative specialist, support worker with the elderly, affiliate marketer, etc., as I was figuring who I was, what I was good at and what was my fit. There’s a lot of voices out there and growing up authoritarian, I looked outside of myself for the answers. What did other people think I should do? It wasn’t until I was able to look within myself and know what I was capable of and ready for, it hit me that I was certified as a coach.
But I still wasn’t ready to come out as a coach and I was scared to talk with people. The problem was that I was comparing myself to other people, other coaches. What I really wanted to do was help people and be there for them. I wanted to meet people where they were at, hold space and be there to guide or mentor. I broke down many times, hiding away from the world and all the voices. I had days where I didn’t want to continue on and I didn’t know if I could be resilient. I didn’t know if I could keep up with life at all. But I stayed the course because I knew that feelings and emotions come and go. They are valid as we do feel them in the moment. But they are not reality. And they are not the bigger picture. So I kept taking small steps, and growing my confidence and courage and working out who I was so I could say I’m an Encouragement & Empowerment Mentor.
All the while, I was podcasting and writing and also doing live talks as a speaker. All of these experiences working together have helped me to be more resilient and find myself as I kept pivoting and taking those small steps forward.
Contact Info:
- Website: https://www.stephanieannwebb.com/
- Instagram: https://www.instagram.com/stephanie_ann_webb/
- Facebook: https://www.facebook.com/Stephannwebb/
- Linkedin: https://www.linkedin.com/in/stephanie-ann-webb/
- Youtube: https://www.youtube.com/@StephanieAnnWebb
- Other: https://www.youtube.com/@TheStephUpPodcast https://www.tiktok.com/@stephanieannwebb

Image Credits
Christian Del Rosario Photography

