My Solopreneur Life

Here’s the thing: nobody warns you how weird, and sometimes downright cringey, it feels when you try to sell your own services for the first time. If you’ve ever wondered why asking for business is so much harder when you’re the product, you’re not alone. In this episode, I open up about my own early sales stumbles, breakout moments, and the wild learning curve faced by solopreneurs who never planned on “selling themselves.”

We dig into the three real reasons selling yourself feels so awkward: the “ick factor” (not wanting to sound salesy), the looming fear of rejection (because a “no” can feel oddly personal), and the chaos of having no actual process (hello, winging it). I share stories, hard-won lessons, and tactical prompts so you can start untangling your own story about sales and maybe start to enjoy it. Trust me: you can learn to sell without feeling gross, and the result is more confidence…and more clients you love working with. What’s your story about selling yourself and is it actually true? Maybe we should talk about it.

In this Season 2 finale of My Solopreneur Life, I recap what “starting” really took for me and the breakthroughs I had along the way. I share why starting is not a one-time event but a choice I make at key moments, guided by intention, mindset, and the story I tell myself. I talk about how inquiry and qualitative research shaped my practice and how spotting client patterns led me to my Better Three model: better understanding, better communications, and better relationships. Guests like Pia Silva, Harry Travis, and Dale L. Roberts reminded me there is no single right way to begin. I also preview Season 3, “Confident Selling for Solopreneurs,” where I will turn fears into clients with mindset shifts and practical, relationship-first tactics. To get ready, I invite you to review recent sales calls, practice with friendly listeners, gather feedback, clarify your tools and process, and track win rates so you enter Season 3 prepared to sell with confidence.

In this episode of My Solopreneur Life, host Terry Pappy talks with Natalie Benamou, founder of Her C-Suite, about launching and growing a purpose-driven business in the second half of life. Natalie shares her journey from corporate trade show executive to community builder for high-achieving women, including how COVID-19 forced a pivot, the challenges and lessons of running a membership model, and how to scale without losing the personal touch. From choosing the right tech stack to aligning your offerings with client values, this conversation is packed with hard-won insights for solopreneurs ready to reinvent themselves and stay relevant.

In the second part of my interview with Pia Silva, author of “Badass Your Brand,” we explore how solopreneurs can build businesses that truly last—even when things plateau or feel like a rollercoaster. Pia gives practical advice for sustaining growth, tackling dry spells and peaks, and freeing yourself from the need for “perfect” monthly income. We talk honesty in client relationships, gaining confidence, and why it’s crucial to set boundaries that protect both your business and your personal life. Pia also shares generous gifts—including a free audiobook and pricing calculator—for all listeners.

In this first part of my two-part conversation with Pia Silva, author of “Badass Your Brand,” we dive into the practical foundations of building a sustainable solopreneur or small agency business. Pia shares how her simple, bold business model transformed my own career, and we discuss real-world strategies for pricing your services, building confidence, and creating a business that lasts. Pia explains why incremental price increases, controlling your schedule, and dedicating time to work on your business—not just in it—are essential to long-term success. Whether you’re just starting or feeling stuck, Pia’s advice is actionable and inspiring.

In this episode, I catch up with Stevie Johns, founder of Inkwell Management. Stevie shares her personal story of leaving a corporate career to start her own boutique speaker management agency, and how she grew her roster from three to eighteen speakers in her very first year. We talk about the importance of building authentic, heart-driven relationships and how that’s been the foundation of her business.

Stevie opens up about the fears and uncertainties of going solo, including the financial risks and emotional ups and downs. She explains why she invested in support early on and how flexibility and learning from each client shaped her systems. Most importantly, Stevie offers direct advice for anyone launching a solo business:

Start today—take even small steps to move forward.

Make self-care a priority so you can show up fully for your business.

Focus on genuine relationships, not just selling.

Stay true to your values and be willing to adapt as you go.

If you’re thinking about starting your own business or are in your early years as a solopreneur, this episode is packed with honest insights and actionable advice from someone who’s right in the thick of it.

In this episode, I sit down with Penney Fox, content marketing strategist and 26-year solopreneur veteran. Penney shares her journey from building websites after a long career in radio, to becoming an authority on content and marketing. We talk about the realities of starting your own business, dealing with self-doubt, and evolving your offerings over time.

In part two of my conversation with Dale L. Roberts, Dale shares real-world advice and actionable steps for solopreneurs at every stage. We dig into practical considerations when starting a solo business—like making sure you have a financial safety net, getting educated about your field before “burning the boats,” and the powerful impact of finding a mentor. For those who’ve already taken the leap (or are feeling stuck), Dale talks about the importance of showing up every day—even when motivation fades—and dedicating your time to actions that truly move the business forward.

Dale also highlights the need for building a support network and not isolating yourself, no matter how “solo” your business is. We both agree that regular breaks and self-care are crucial—Dale even schedules quarterly vacations to recharge. If you’re a new solopreneur or one looking for inspiration to push through a tough season, this episode is packed with honest, applicable wisdom you can use right away.

In this first part of my two-part conversation with Dale L. Roberts, I talk with Dale about how he got started as a solopreneur and self-published author. Dale shares how a challenge from his corporate wellness coach led him to write his first fitness book—something he’d always dreamed of but never pursued seriously until that moment. Dale talks honestly about those early days: the influence of his wife Kelly (also a solopreneur), the leap from a steady job, making that first $21 in royalties, and the tough reality of struggling in the first couple of years—draining his savings and doubting his path.

Dale reflects on the mindset shifts required, from initial optimism (and what he calls “delusional belief” that success would be instant) through the hard lessons of spinning his wheels until he sought help from a coach. He explains how coaching and humility helped him focus, stop “spraying the firehose everywhere,” and finally build real traction. Dale’s story is full of honest insights about what it really takes to leave a job and make your big idea happen.

If you’re contemplating your own solopreneur start or stuck in those difficult early years, Dale’s journey is a candid reminder that persistence, self-awareness, and asking for help are all part of the process.

In preparation for a talk to a group of folks considering starting their own business, I worked up a list of 7 items that matter A LOT. Here they are:

1. Finances - get on top of your finances before doing anything else

2. Passion - be clear on what you want to do

3. Mindset - secure a growth mindset

4. Relationships - your network is your gateway to success

5. Invest - get a coach to guide you along your journey

6. Learn - keep your skills sharp, study your industry

7. Action - Just do it and make each action move your business forward