8 Conversations. 8 Women. 8 Inspiring Stories.
Over eight Substack Live conversations, Sarah Stone interviews women who are beginning, building and scaling - exploring the courage, choices and lessons behind creating success on their own terms.
The Courage to Leave What’s Comfortable
Editors Note By Sarah Stone
Starting From Zero Live Series - Day One with Jennifer Villasante
There’s something I’ve been wanting to do since Starting From Zero began to take shape, I wanted to create space for the conversations we don’t hear enough of.
Not the polished stories about what someone has built once they’ve made it, but the conversations that happen while they’re building it. The decisions, self doubt and the uncomfortable moments that challenge your belief system.
Because so many of us are starting from zero somewhere in our lives right now. Whether that’s a new business, publication or relationship with ourselves.
And very often, starting from zero doesn’t necessarily mean starting with nothing because we already have so much experience, wisdom and evidence of everything we’ve already survived, created and figured out along the way.
That’s what inspired me to create the Starting From Zero Live Series.
The Interview Day One: Jennifer Villasante
Jennifer Villasante has spent more than six years building a community of nearly 20,000 followers on Instagram after originally opening her account to hold herself accountable to a goal of losing 50 pounds.
What began as a personal challenge became something much bigger - a community built around lifestyle, health, encouragement and the lessons Jennifer learned through transforming not only her body, but the way she thought about herself.
Now, as she approaches 54, she’s making another enormous change. After a lifetime working in hospitality - a world she shared that she could now walk into and operate “with my eyes closed” - Jennifer has made the decision to step away from the career she knows and pursue the work she feels increasingly called to do.
At the same time, she’s arrived here on Substack and is starting from zero. This is something I wanted to talk about - leaving the comfort and safe of everything you know, to lean into the purpose-led vision that is being birthed into the world.
We unpacked what changes when, in midlife, you finally have enough evidence behind you to think “I’ve figured things out before. I’ll figure this out too.”
And then Jennifer said something that, for me, captured the entire conversation:
“Every time I’m scared and I finally do something that I’m scared to do, it turns out to be way better than I ever expected.”
And I thought...
Well, there’s our Day One lesson.
Sometimes the thing waiting on the other side of comfortable is far better than the thing we’re frightened to leave behind.
Enjoy the interview,
The Courage to Leave What’s Comfortable
Sometimes one decision changes far more than we expect.
Jennifer’s story on Instagram started around six and a half years ago with a very personal goal - she wanted to lose 50 pounds.
She had struggled with her weight throughout her life and, at one point, reached 342 pounds. She described the cycle so many women will recognize: wanting to change, believing she couldn’t, trying again, and finding herself back in the same conversation with herself.
Eventually she decided to try something different so she opened an Instagram account - her thinking was simple - if she put the goal out there publicly, it would hold her accountable.
What she couldn’t have known was what that one decision would eventually become. The account grew and people began following her journey and slowly, what had started as personal accountability became a community of inspiration and motivation for herself and others.
She realized that losing 50 pounds wasn’t going to magically make everything wonderful because the bigger work was learning how to create a life she could actually sustain.
We often focus on the visible transformation but changing the way we think about ourself. Jennifer wasn’t simply changing her body - she was also building the confidence that she could trust herself.
And years later, that evidence is helping her make a completely different kind of change.
The voices don’t disappear… we just stop letting them make the decisions.
One thing I particularly appreciated about Jennifer was that she shared that even before coming to a recent lunch we’d arranged, she almost cancelled.
Those familiar thoughts crept back in.
The doubts. The reasons to cancel. The voices telling you to fear the unknown.
The difference now is that she recognizes it. As Jennifer put it, she doesn’t allow those thoughts to “speak loud in my head anymore.”
Instead, she tells herself:
“It’s okay. I’ve got this. I am going to do it.”
I loved that. Because perhaps we’ve misunderstood confidence. What if confidence isn’t reaching a point where we’re no longer frightened - maybe it’s where fear is no longer automatically given the deciding vote.
We spend weeks, months - and sometimes years - imagining everything that could go wrong on the other side of a decision. Very rarely do we give the same energy to imagining:
What if it’s better?
If you’re starting something new too, you’re in the right place.
Starting From Zero is where I’m sharing the honest conversations, experiments and lessons behind building something meaningful from the very beginning.
Starting from zero isn’t the same as starting from nothing…
This was probably one of my favourite parts of our conversation because Jennifer has started again several times and when you’ve lived for five decades, you have evidence.
Evidence that you’ve figured things out before.
Evidence that the route doesn’t always go to plan.
Evidence that sometimes there’s a detour.
Evidence that things can take longer than we expected.
Evidence that we’ve survived days we once couldn’t imagine getting through.
Jennifer’s own story contains so much of that.
Want to keep reading?
Paid members can continue the conversation below, where Jennifer and I talk about becoming a beginner again, what she’s building next, the three promises she’s making to herself—and the advice she’d give another woman standing at the edge of her own comfort zone.
From influence to impact.
Jennifer worked three jobs when that’s what life required. She has navigated enormous personal experiences and now she’s reached a point where she’s prepared to leave the career she’s known and put her energy into something that feels much more connected to what she wants to contribute next.
Now she’s sharing that influence is more than numbers - it’s about the impact you have on another person because you shared something…. someone who doesn’t believe in herself borrows a little of Jennifer’s belief.
Someone who doesn’t feel confident sees that Jennifer didn’t always feel confident either. and someone struggling to stay motivated sees a woman who got up and did the workout anyway.
That’s the impact Jennifer is making and I think that’s where platforms like Substack become really interesting - there is room for the whole person here.
Not just the highlight reel.
So, what is Jennifer building now?
This is where I think Jennifer’s story becomes particularly exciting. She doesn’t want to keep everything she’s learned over the last six and a half years to herself anymore.
She’s building Hey Now Jen as a place to share it and she’s not gate-keeping anything there! It’s not just about meal plans and recipes - it’s about the moments that happen before the decision.
That conversation you have with yourself when you’re tired and you’re about to stop at McDonald’s because you can’t think of anything else to do.
The habits. The shortcuts. The thoughts. The mindset.
The practical things that make taking care of yourself easier when you’re living an actual life rather than a perfectly curated one.
The Takeaway: Make The Promises To Yourself.
Jennifer shared something wonderfully simple that she’s practising right now. She’s doing a 30-day challenge built around keeping three promises to herself every day.
They don’t have to be enormous…. drink the water, get your protein, take the walk - whatever your three things are. Choose them.
And then keep your word to yourself. Jennifer said:
“Make those three promises and keep them to yourself because you are worth it.”
I think that’s such a lovely place to begin because we often make stepping outside our comfort zone sound enormous.
Quit the job!
Launch the business!
Write the book!
Move across the country!
Start the Substack!
Sometimes courage does look like that.
But most of the time, I think courage is built much softer - one promise kept, then another, then another… until one day you have enough evidence to realize:
I can trust myself with the bigger decision too.
What Jennifer wants you to know…
If I had to distil our conversation into one piece of advice, I think it would be this:
Don’t assume fear means no.
Jennifer has been scared before every significant new beginning and the fear didn’t ever disappear but she moved anyway. And repeatedly, the thing on the other side turned out to be better than she’d imagined.
Perhaps the question isn’t:
“How do I become fearless enough to do this?”
Perhaps it’s:
“Am I willing to do this while I’m still scared?”
That’s a very different question.
Discover Heynowjen
If Jennifer’s story resonated with you, I’d love you to support her as she builds this next chapter.
She’s starting from zero here on Substack, bringing with her more than six years of lived experience, practical ideas and the kind of encouragement that comes from somebody who knows what it’s like to have to begin again herself.
JOIN THE STARTING FROM ZERO COMMUNITY
🎁 Today’s Birthday Celebration Perk For Annual Member’s
And because this conversation is part of my eight-day Birthday Celebration, I’m also revealing another reason to join me as an Annual Member.
Today’s perk is my:
Substack Branding Kit - 22 Canva Templates
A ready-to-customize collection created to help you give your Substack a polished, cohesive look without having to design everything from scratch.
If you’re building your own publication—or thinking about starting one—I want to make that beginning feel a little easier.
Everyone who joins the Annual Plan during my Birthday Celebration receives the Branding Kit, my Business Resources collection and all the additional Birthday Celebration Perks I’ll be revealing throughout the series.
Love Jennifer’s Substack Style?
There’s another part of Jennifer’s story that you may not know. We’ve been working with her behind the scenes to help take everything she already had - the ideas, the experience, the personality, the audience and turn it into a Substack publication she felt confident taking live.
That’s the work I love.
Because sometimes starting from zero doesn’t mean you need another course showing you 47 things you now have to figure out yourself. Sometimes you want someone beside you.
To help you clarify the idea.
Shape the publication.
Create the brand.
Build the platform.
And support you until you’re ready to press publish.
If you love Jennifer’s Substack style and you’ve been thinking about creating your own, I offer packages designed to help you go live with your Substack with clarity, confidence and support.
Starting From Zero has honest conversations about what it really takes to build a business, community and life that actually supports you in every season.
Talk Topics Include:
Make big moves toward the success you actually want - without doing it alone.
Show up consistently as the woman you’re becoming, even when life gets messy.
Build a community so the right people find you, trust you and stay with you.
Take action towards everything you’re worthy of.
Free For Everyone
Start here if you would like to receive public posts, selected guidance and access to the Intentional Conversations.
✔ The Journal - Honest essays, twice a month.
✔ A Daily Intention in Notes - Small prompts that keep you moving.
✔ Intentional Conversations - Live conversations about Starting From Zero and Redefining Success.
Become A Monthly Paid Subscriber
If you want premium content and closer access to my best work.
✔ The Editor’s Letter - One deep-dive article every month that highlights the live interviews, insights and the honest take-aways of nurturing a sustainable business and lifestyle.
✔ A Daily Intention in Notes - Small prompts that keep you moving.
✔ Intentional Conversations - Live conversations about Starting From Zero and Redefining Success.
✔ The Annual Vision Board Workshop - A guided session to map the year ahead with intention. Takes place every January.
Annual Membership Special
Pay Annually & Unlock Bonus Content:
✔ Quarterly Workshops - 4 x Members-only live workshops from dedicated Wellness Experts & Special Guests.
✔ Private Networking Sessions - Quarterly Substack Social, Annual-members-only Zoom to learn, connect, collaborate and meet other women doing great things.
✔ 10% off working with me 1:1 - When you’re ready for hands-on, strategic support, your subscriber discount applies to a Power Session.
→ See full details on the Become a Member page.
From my heart to yours,
Outside of Substack, you’ll find me creating Intentional Living Magazine and helping private clients build their platforms through House of Brand.
