Terry Pappy

My Solopreneur Life

Business EN ↓ 67 episodes

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 a...

Author

Terry Pappy

Category

Business

Podcast website

tpappy.com

Latest episode

May 25, 2026

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Episodes

MSL 415 - The wrap of “My Solopreneur Life” and why I'm starting a new show…oh, it’s gonna be so awesome! 25.05.2026

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 at the core of who I am: writing from the heart, finding your voice, and bringing real human experienc...

MSL 414 - How simplicity and structure can eliminate overwhelm with Andrew Hartman (part two) 11.05.2026

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 problem. The real issue is that we keep saying...

MSL 413 - How solving your own burnout can lead to a business with Andrew Hartman (part one) 27.04.2026

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.

MSL 412 - AI isn’t replacing you, it’s exposing you: the real way solopreneurs should use AI 13.04.2026

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 as this technology gets better, trust bec...

MSL 411 - The unconscious way solopreneurs kill their best ideas (and how to save them!) 30.03.2026

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, and can even stop them from becoming somet...

MSL 410 - The sales pitch mistake solopreneurs make and what to do instead to win the work 16.03.2026

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. The problem is that prospects are...

MSL 409 - The overlooked skill that will grow your solopreneur business faster than any other 02.03.2026

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, identifying gaps, rethinking assumptions, and findi...

MSL 408 - Mindset, pricing, and having the courage to ask for the sale with Miriam Schulman 23.02.2026

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 that help artists and creati...

MSL 407 - From isolated to energized! Building connection as a one-person business 16.02.2026

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. Because being a solopreneur doesn’t m...

MSL 406 - The identity shift every solopreneur must make to thrive long-term 09.02.2026

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 casually call imposter syndrome. In this episode of My Solopreneur Life , I unp...

MSL 405 - Why solopreneurs overdeliver and how it quietly destroys confidence and business 02.02.2026

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 how we show up for clients....

MSL 404 - You can’t fool your audience! Authenticity, AI, and the solopreneur trust gap 26.01.2026

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.

MSL 403 - When your business infrastructure shakes: navigating personal crisis as a solopreneur 19.01.2026

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 husband and corporate job within the same season...

MSL 402 - Three fears most solos never talk about when starting a service-based business 12.01.2026

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.

MSL 401 - Intro to season 4: Diving deep into the unspoken side of solopreneur life 05.01.2026

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 things appear to be going well. I share...

MSL 316 - Beyond sales: what solopreneurs don’t talk about (but should) Season 3 wrap + what’s next 29.12.2025

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 revisiting, and land on the simplest truth I know...

MSL 315 - Five AI conversations that turn reluctant solopreneurs into confident closers (no tech skills needed) 22.12.2025

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 skills required, just prompts you...

MSL 314 - 6 ways to stop sounding like a sales bot and authentically connect with prospects 15.12.2025

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. They're permission slips to be human, build...

MSL 313 - Follow up like you mean it: Turn prospects into clients and make your solopreneur brand stand out 08.12.2025

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.

MSL 312 - Five easy ways to turn your business website into a 24/7 sales rep 01.12.2025

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.

MSL 311 - How curiosity can quiet your sales fears with Naveed Bhatti (part two) 24.11.2025

In this episode, I continue my conversation with Naveed Bhatti about the inner game of selling as a solopreneur. We go deeper into the mindset, fears, and self-talk that can make sales feel uncomfortable and how to reframe those thoughts so you can sell with confidence and authenticity. Naveed shares how his early cultural beliefs about sales shaped his fears, and what it took to rewrite that stor...

MSL 310 - Discover what’s missing in your sales conversations with Naveed Bhatti (part one) 17.11.2025

In this episode, I have a very thoughtful conversation with my longtime friend and client Naveed Bhatti , who brings deep experience in sales and leadership coaching. We talk about what really happens when you leave corporate life, where the company’s name and sales team did the heavy lifting, and suddenly have to sell yourself. Naveed shares how to shift from borrowing credibility from a company...

MSL 309 - Get to yes faster: 3 ways to remove friction from your solopreneur sales conversations 10.11.2025

In this episode, I share the practical ways I’ve learned to smooth out that friction—both on my website and in the way I show up for a sales call. I walk you through exactly how I tweaked my booking process, rewrote my website copy, and made sure every sales conversation had a simple, supportive plan behind it, so prospects feel informed and ready to work with me before we ever meet. The result? L...

MSL 308 - Sales conversation tips that build trust and clarity with Darleen Priday (part two) 03.11.2025

In part two of my conversation with Darleen Priday, we discuss practical steps and mindsets to make client sales calls feel supportive, genuine, and productive. From leading with vision statements to organizing follow-ups with intention, you'll hear approaches that help you sell authentically without ever feeling pushy. Whether clarifying your offer or booking the next step, prioritize clarity and...

MSL 307 - Transform your sales mindset and process: real strategies for solopreneurs with Darleen Priday (part one) 27.10.2025

In part one of my two-part conversation with Darleen Priday, we talk about how you can shift your sales mindset and build genuine trust with potential clients even if you’ve always struggled to see selling as natural. You’ll also catch a few actionable strategies and structures that transform sales from anxiety-inducing to authentically rewarding.

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