My Solopreneur Life

My Solopreneur Life

It’s for sure that running a one-person business takes courage, execution, and a whole lot of learning—but you don’t have to figure it all out by yourself. My Solopreneur Life is your go-to resource for confidence-building inspiration, actionable business insights, and real talk about what it takes to be a successful solopreneur, hosted by 20-year solopreneur, Terry Pappy. In addition to tips on solopreneur marketing, sales, branding, and customer experience, you’ll also hear from fellow solopreneurs who generously share their wisdom, wins, and lessons learned along the way. In a world where any dream can be made real, your passion-led work deserves to thrive—and My Solopreneur Life is here to help you make it happen.

Episodes

After four seasons and a year and a half of My Solopreneur Life, this episode marks the end of one chapter and the beginning of an exciting new adventure.

I’m sharing the story behind my decision to launch a new show, The Signal, and why I’m feeling pulled back to something that has always been ...

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In this second part of my conversation with Andrew Hartman, founder of Time Boss, we move from origin story into the practical reality of how his system actually works. Andrew breaks down what was happening beneath his own burnout and what he discovered through years of experimentation: most overwhelm isn’t a time problem, it’s a capacity and decision probl...

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Andrew Hartman didn’t set out to start a business. He set out to fix his own burnout. In this episode, we talk about how solving that one problem led to Time Boss, and what solopreneurs can learn about building something that truly works.

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In this episode, I get real about what I’m actually seeing with AI as a solopreneur, not the hype, not the fear, but what’s happening in the day-to-day trenches of running a business. I share a moment that genuinely stopped me in my tracks when I saw how realistic AI-generated avatars have become, and why that matters more than most people realize. Because ...

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I’ve noticed something about myself over the years as a solopreneur, and I see it in others all the time, too. We come up with a great idea, get excited about it, and then we start talking about it before it’s fully formed. In this episode, I break down the unconscious habit of sharing ideas too early and how it quietly drains their energy, creates doubt, a...

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In this episode of My Solopreneur Life, I share one of the most common mistakes I see solopreneurs make when they finally get in front of a potential client. After all the effort it takes to generate a lead and secure a meeting, many of us fall into the same trap. We start talking about our process, our technology, our methods, and all the things we’re proud of. ...

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Most solopreneurs focus on execution, productivity, and output because that feels like the safest way to grow a business. In this episode, I share why that mindset eventually limits you — and why creativity is one of the most overlooked skills in solopreneur success. Creativity isn’t about being artistic or expressive. It’s about seeing patterns, iden...

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In this episode of My Solopreneur Life, I chat with Miriam Schulman, author of Artpreneur: The Step-by-Step Guide to Making a Sustainable Living From Your Creativity and creator of the Artist Incubator program. Miriam shares her pivot from a Wall Street career after 9/11 into building a long-term art business, then turning her hard-won lessons into coaching frameworks ...

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In this episode of My Solopreneur Life, I share my own experience navigating years of working alone and what I’ve learned about creating connection on purpose. From building local networks and micro-interactions to using movement, community, and even AI as a thinking partner, I walk through practical ways to stay energized, visible, and emotionally supported. Bec...

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When you leave corporate or step out on your own, something subtle but heavy shows up fast: you lose the identity that once defined you. You’re no longer “the director at X company” or “the marketing lead at Y.” You’re just… you. And for many solopreneurs, that blank space creates fear, second-guessing, and what people casuall...

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In this episode of My Solopreneur Life, I explore a pattern many solopreneurs fall into without realizing it: overdelivering as a form of self-protection. Drawing from early experiences after a corporate layoff and the emotional weight that shaped those years, this conversation looks at how low confidence, unclear boundaries, and fear of losing work can quietly distort...

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I explore why authenticity matters more than ever in an AI-driven business landscape. As solopreneurs adopt AI tools to save time and streamline marketing, it’s easy to create polished content that looks impressive but overpromises the real client experience. That growing gap between presentation and reality quietly erodes trust.

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As a solopreneur, you aren’t just the CEO—you are the infrastructure of your business. But what happens when life hits hard and your personal reality feels like it’s taking your knees out? In this vulnerable episode, I talk about the "hidden reality" of running a business through grief, loss, and trauma. Drawing on my pivotal experience of losing my h...

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In this episode of My Solopreneur Life, I talk openly about the quiet fears and internal stories that surface when you’re thinking about going out on your own, whether you’re still employed or navigating a recent layoff.

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In the first episode of the season, I introduce the theme of the hidden realities of managing a solopreneur life by naming the unspoken internal experiences many solopreneurs carry alone. This episode isn’t about tactics, hustle, or highlight reels, but about the mental and emotional load, the self-doubt, and the quiet questioning that can surface even when thing...

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Season 3 is a wrap, and the biggest takeaway is this: most sales struggles aren’t about tactics, they’re about belief systems. The stories we carry about selling (not wanting to feel pitchy, desperate, or inauthentic) often block the success we want. In this finale, I share what I learned from the season, point you to key guest conversations worth revisitin...

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Wrapping up the "turning fears into clients" season with five tactical AI conversations every solopreneur should be having but probably isn't. Learn how to use AI as your thinking partner (not a robot) to clear mindset blocks, identify ideal prospects, research without stalking, process calls faster, and refine follow-ups that sound authentically you. No technical skil...

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Sales conversations feel gross when you're trying to follow a script or sound “professional.” But here's the thing: your prospects can smell inauthenticity from a mile away. In this episode, I'm sharing six practical ways to show up as yourself during sales calls, from sharing honest struggles to ditching corporate jargon. These aren't tricks or tactics. Th...

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This episode breaks down the tactical follow-up strategies that actually work, from post-call emails to creative relationship-building touches that show you're listening.

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In this tactical episode, I shift from mindset to action and walk you through five concrete ways to transform your website into a high-performing sales tool that works while you sleep.

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