Seasons, Storms & Stepping Into Your Speaker Leader Era with Stephanie Ross

Written By Catherine Roten

In this episode, we talk about:

  • Why every business moves through seasons, not just success

  • The difference between planting, growth, storms, and harvest

  • How burnout can be a signal instead of a setback

  • Why community matters when entrepreneurship feels lonely

  • Learning to eliminate instead of doing more

  • What makes a speaker truly transformational, not just informative

  • How to build a talk that creates lasting impact

Stephanie Ross returned again on the podcast and when we recorded her first episode, she was thirty-five or thirty-six weeks pregnant. Now she is a mom, her son Val is a year and a half old, her book has been out for over a year, and here we were recording again… with me now the pregnant one. Life is funny like that.

Stephanie is the founder and community leader of Small Business Sister Circle, an in-person and virtual community for female small business owners that started in La Crosse, Wisconsin and is now expanding into chapters across the Midwest. She is also the author of Seasons of a Soulpreneur, a speaker, and a speaker trainer… though she would tell you that at her core, she is simply a creator and a teacher. And everything she touches reflects exactly that.

This conversation covered a lot of ground, from how she built one of the most genuinely engaged communities I have ever been part of, the seasons framework that has become a lens I come back to over and over again, and her speaker training that is now available as a digital course. Let's get into it!

How She Built a Community People Actually Show Up For

I have been to La Crosse four times in the last year, maybe five. And every single time I walk into a Sister Circle event, I am struck by the same thing: people are actually there. Not just physically present, but engaged, open, willing to share where they really are.

I asked Stephanie how she built that.

"I started Sister Circle in my rock bottom moment. And I've taken people along the journey. From that really hard place through all of it. From what I call my season of a storm to my harvest season, to planting, to a growth season again. I think just being really real and honest and vulnerable about my own experiences in entrepreneurship has drawn the right people into the room." - Stephanie

She also made a point that I think gets overlooked in a lot of community-building conversations. She was not trying to create something trendy or clever. She was building what she could not find.

"I looked around and couldn't find what I was looking for. And that's why I created it. I didn't fit in at a chamber meeting. I didn't fit in at BNI networking where it's all surface level, give me your business card, give me referrals, transactions without really building the relationship. I built what I built because I couldn't find it." - Stephanie

And the reason people feel safe showing up and sharing where they actually are? Stephanie is not on a pedestal.

"Yes, most people see me on a stage. But I'm often sharing from my hardest seasons. And I think that really makes all the difference for someone to feel comfortable to show up and share where they're at because none of us are really, quote unquote, there. We haven't made it. And there is no such thing as that." - Stephanie

The Seasons of a Soulpreneur

If you have not read Stephanie's book yet, this section alone should convince you to grab it. The seasons framework is something I keep coming back to, especially right now, in this season of my own business.

Here is how Stephanie breaks it down:

Planting is often the earliest stage. When you have the spark of an idea, you are building something new, or you are launching a whole new arm of an existing business. It does not just apply to brand new entrepreneurs. Stephanie herself was in a planting season last year after launching her book, even with over a decade of entrepreneurship behind her.

Growth is when things start to take off. Your calendar fills up, you have to start saying no to things, you begin building a team or systems, and you are in the heavy marketing and scaling phase. It sounds exciting, and it is, but it also comes with growing pains, overwhelm, and the pressure of expanding to new levels.

Storm is the season most of us try to avoid talking about. But Stephanie does not let us off the hook.

"Storms come because sometimes they are just growing pains in our business, and oftentimes they're unforeseen challenges we can't actually plan or prepare for because we've never experienced them before. The storms are heavy. They require a lot of deep inner work and reflection, and honestly, just pulling yourself out of your business more, which feels really counterintuitive." - Stephanie

She also said something that I needed to hear, and maybe you do too:

"Oftentimes it's not about more. It's actually about doing the right things and eliminating the things that are stealing your time and energy. But we cannot get to the harvest season without the rain." - Stephanie

Harvest is where you finally get to reap what you have worked so hard for. Maybe it is financial. Maybe it is time freedom. Maybe it is finally getting to work fully in your genius and lead and mentor rather than doing all the things. But Stephanie is honest about the challenge that comes with harvest too — boredom, or the pull to go back in and become the bottleneck of your own business all over again.

And then,  it starts over. You plant again.

"The point of the seasons is to understand where you're at, that you're not alone, how to support yourself, and to understand that there are seasons and cycles and we're never really ever done. We don't just hit harvest and stay there." - Stephanie

I will be honest… as she was talking through this, I was quietly mapping out exactly where I am right now. In a storm in my consulting business. About to head into a brand new planting season as a first-time mom. Both things are true at the same time. And somehow just naming that made it feel less heavy.

Stepping Into Your Speaker Leader Era

The third big thing we covered is something I have personally experienced and can fully vouch for, Stephanie's speaker training.

It started, like so many other things, out of necessity. She needed speakers to cover her paid membership meetings while she was on maternity leave. She had a standard of quality for who showed up on her stages, and she realized most people, even people with a lot of knowledge and expertise, did not know how to actually deliver it in a way that moves people.

"Most people are what I call subject matter experts. They have a lot of information. They don't know how to deliver it in a way that actually moves people into action. What I'm teaching is how to actually teach and speak in a way that is engaging, that is also transformational, not just speaking at people and dumping tons of information on them." - Stephanie

The training has evolved a lot since those early days. She has now trained over eighteen speakers in person across two live cohorts and the results speak for themselves.

"I can't tell you how many people at summit this year were so impressed by our speakers who we have trained through this program. You can tell who has gone through our speaker training and who has not, just by the level of experience they bring to the stage, the confidence, the framework, how they teach, how they lead." - Stephanie

And now? It is available as a digital course. Three levels:

  • The course- work through the framework at your own pace, designed to be completed in just two focused days, and you walk away with a full talk built out

  • Course + certification- includes a one-on-one workshopping session with Stephanie and you submit a video of yourself delivering your talk to earn your Sister Circle certified speaker status

  • Course + certification + retreat- everything above plus the in-person retreat in La Crosse this October

One thing I want to highlight because Stephanie said it and it genuinely reframes the whole thing: the training is built around a ten-minute talk. And that is intentional.

"A ten-minute talk is actually way harder than any other length. It's not about squeezing in information. It's about making the most impactful, important information clear and obvious through the transformation you're taking your audience on. If you can build out a ten-minute talk, you can take that and expand it in a million different ways." - Stephanie

She also confirmed lifetime access to the course, so every time you want to build a new talk, you go back through the same framework and build it fresh.

I went through this training in person and I will tell you: block two full days. Do not spread it out over two weeks. Give it the time and focus it deserves and you will walk away with something real and ready to use.

Connect with Stephanie

Stephanie and everything she is building is worth getting into, especially if you are somewhere in the seasons right now and need the reminder that you are not alone in it.

Cat Roten

Intuitive Leader & Mentor

Catherine Roten
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