Reflections on 50 Interviews with Entrepreneurs Who Work From Home

Simple Lessons you can apply to your own journey starting today

What really happens behind the scenes of an entrepreneur’s day?

Not the highlight reel… Not the perfectly curated posts…

But the real, everyday rhythm of building something from home—while managing life, distractions, uncertainty, and growth.

This week, I published my 50th interview in the Entrepreneurs Who Work From Home series.

· Fifty interviews.

· Fifty conversations.

· Fifty windows into what this journey actually looks like.

And what I’ve discovered is this: we’re far more alike than we think.

One of my biggest goals with this series has always been simple: to help entrepreneurs like you navigate this journey—and not give up when it gets hard. Because it does get hard.

There are days filled with doubt, distraction, and uncertainty. But what I’ve seen through these conversations is that every entrepreneur faces those moments… and finds a way to move through them.

My hope is that when you listen to these interviews, you don’t just learn something new—you feel encouraged to keep going, to find your rhythm, and to trust that you can build something meaningful, one step at a time.

The First “Yes”

The very first interview I recorded was with my coach, Lindsay. In fact, she’s the one who encouraged me to begin this series.

I still go back and watch that conversation—because she shared something many of us don’t talk about enough: what it really looks like behind the scenes of running a business.

That first “yes” really mattered to me. Because in the beginning, I wasn’t sure anyone would want to be interviewed.

But one by one, entrepreneurs said yes.

And those yeses turned into conversations around the world— from different states across the U.S., to Europe, Australia, Singapore, and Dubai.

Different backgrounds. Different businesses.

And yet… such similar experiences.

What These Conversations Revealed

Some of the entrepreneurs I’ve interviewed are coaches. Others are service providers, authors, affiliate marketers, or product creators.

Some are building businesses solo.

Others are building together as couples—like the pair living in Portugal or the duo launching a nonprofit in Romania.

Different paths—but shared challenges.

Because building a business from home requires more than strategy.

It requires resilience, discipline, and intention.

The 10 Questions I ask that Matter

Before each interview, I send the entrepreneur a list of 10 questions. Not to script the conversation—but to create a space where real insight can surface.

One recent guest told me those questions helped her feel grounded and prepared before we even started. And that’s exactly why I chose them.

Because they reflect the real, daily challenges we face:

• Managing time

• Handling distractions

• Navigating isolation

• Staying current with technology

• Continuing to grow—personally and professionally

When entrepreneurs answer these questions, what they share is gold. Not theory—but lived experience.

What We Talk About

Each interview opens with what you’ll learn from this entrepreneur, and closes with my 3 Gems of Wisdom that they share—but it’s the conversation in between that brings everything to life.

We explore:

Daily Routines No two entrepreneurs start their day the same way. From structured mornings to flexible rhythms, each routine reveals what supports consistency and growth. Watch Repeatable systems with Mona Weathers.

Home Office Design. The spaces we work in matter more than we think. Each setup reflects how entrepreneurs support their focus and energy.

Challenges. Every entrepreneur faces obstacles—but how they respond is what moves them forward. Watch LeeAnn Webster talk about “no regrets, no limits.”

Technology & Tools. This is one of my favorite parts—learning about tools and systems from each entrepreneur that make business more efficient and sustainable.

Time Management: Hearing how others structure their days has been incredibly insightful and practical.

Collaborations & Connections: If there’s one theme that continues to stand out, it’s this: That’s one of the reasons I’m building the Entrepreneurs Collab Circle—a space for connection, support, and shared growth.

Goal Setting: Every entrepreneur approaches goals differently, but the intention behind them is the same: forward movement with clarity.

The Ultimate Question: At the end of each interview, I ask:
“If there was one piece of advice you’d give to fellow entrepreneurs working from home, what would it be?” Watch Michelle from Portugal

And the answers are always worth listening to twice.

Self-Care” This is no longer optional—it’s essential. The entrepreneurs who sustain their businesses long-term are the ones who make space to take care of themselves along the way.

What I’ve Learned (So Far)

If I had to sum up these 50 conversations into one takeaway, it would be this:

There is no one right way to build a business—but there is a right way for you.

These interviews have helped me grow—not just as an interviewer, but as an entrepreneur.

I’ve learned new ideas.
I’ve gained practical tools.
And maybe most importantly… I’ve made meaningful connections with people around the world.

Closing Reflection

As I look ahead to the next 50 interviews, I’m not thinking about numbers. I’m thinking about conversations. Because every time someone shares their story, their process, or even their struggle—it creates a ripple.

· A reminder that you’re not alone in this.

· A new idea you hadn’t considered.

· One small shift that can change everything.

So if you’ve been watching, listening, or quietly following along—thank you.

And if you’re just getting started, you’re welcome here too.

There’s a whole world of entrepreneurs out there…
and we’re building this journey—together.

If these conversations are speaking to you, I’d love to invite you to go a little deeper.

You can watch the full Entrepreneurs Who Work From Home interview series on YouTube HERE! Each episode filled with real routines, practical insights, and honest conversations from entrepreneurs around the world.

And if you’re craving more connection and collaboration in your own journey, I’m opening the doors soon to the Entrepreneurs Collab Circle—a space designed for entrepreneurs who want to grow their business in a calm, intentional, and supported way.

Until then, keep showing up, keep learning, and keep building—one step at a time.

PS: If one of these interviews has impacted you, I’d love to hear which one. Just hit reply and let me know—I read every message.