My Solopreneur Life

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 “yes” to more than our attention, energy, and focus can sustainably hold.

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.

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 becomes harder to earn. That’s why I double down on something I’ve always believed: your voice, your personality, and your presence are your edge. I walk you through how I think about AI versus software, and how I’m using tools like scheduling, recording, and summarization to eliminate friction in my workflow without losing the human experience my clients expect from me.

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 something meaningful.

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 not interested in how we work nearly as much as we think they are. What they really care about is whether we understand their problem and can help them solve it.

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 finding smarter ways to serve clients. When creativity gets pushed aside, businesses stall, energy drops, and burnout creeps in.I also talk about how analytical, logical solopreneurs are already using creativity every day without recognizing it. When you solve client problems, refine your positioning, improve systems, or spot new opportunities, you’re being creative. The real growth shift happens when you make intentional space for that thinking instead of living in constant execution mode. Creativity, when treated as a skill instead of a personality trait, becomes a powerful driver of clarity, confidence, and long-term business growth.

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 creative solopreneurs build real income.

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 mean being isolated. With a few intentional shifts, you can design a business and a life that feel connected, human, and deeply fulfilling.

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 unpack why that discomfort isn’t a flaw. It’s an invitation. An invitation to stop borrowing credibility from old job titles and start building a brand that is fully, unapologetically yours.

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.This episode is not about doing less or caring less. It’s about understanding why you might be doing too much, attracting poorly matched clients, or tolerating behavior that doesn’t align with your values. Through real stories and reflective guidance, I invite you to examine how belief systems, self-worth, and boundaries directly influence the quality of your client relationships, your energy, and ultimately, the sustainability of your business.

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.

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, I offers five practical prompts to help you maintain your "Minimum Viable A-Game" while giving yourself the grace to heal.The 5 key takeaways from the episode:Controlled Vulnerability: Using professional scripts to manage client expectations without oversharing personal drama.External Storage: Combating "brain fog" by documenting every detail and trusting your calendar over your memory.Work Sanctuary Rituals: Creating physical and mental triggers to step into your "Solopreneur Identity" for set blocks of time.Minimal Viable A-Game: Identifying non-negotiables to keep the business healthy while lowering the bar for "bonus" tasks.Compassionate Productivity: Giving yourself permission for a "maintenance quarter" to focus on resilience and healing.

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.

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 why this season matters right now, what I hope it gives you as a listener, and how simply putting language to these experiences can steady you and make the path feel more sustainable. This season is about real talk, orientation, and permission, reminding you that you’re not broken, not behind, and definitely not alone.

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 about progress: execution trumps everything.I also tease what’s next, where we’ll go deeper into the things solopreneurs rarely talk about, including fear, self-trust, and the difference between passion-led work and work driven by real skills, so you can move out of overthinking and into a solopreneur life that actually fits you.

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 can use today to do relationship-first sales better and faster.

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 real trust, and actually enjoy talking to potential clients. Because when you stop performing and start connecting, sales becomes a conversation you look forward to instead of dread.

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.

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.

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 story. Together we explore what happens when your focus shifts from yourself to the person you’re helping, and how curiosity, not persuasion, creates connection.For more takeaways and prompts, visit the show notes page.

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 brand to owning your expertise as a solopreneur. We explore what genuine confidence looks like in a client conversation, why most people overthink selling, and how to replace “sales scripts” with curiosity and authentic dialogue.For more takeaways and prompts, visit the show notes page.

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? Less confusion, less time wasted, and many more clients reaching out saying, “I’m ready—what’s next?”

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 generosity. Darleen and I break down exactly how to approach different personalities, adapt talking points, and always finish each conversation with an agreed-upon next step. You'll hear processes for tracking notes, sending written recaps, and providing helpful resources plus why focusing on long-term relationships matters most in any solopreneur business.

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.

In this episode of My Solopreneur Life, I'm walking you through three strategies that helped me go from dreading sales calls to confidently closing deals, and how you can do the same, even if you're naturally introverted.You'll discover how to reframe those uncomfortable cold calls into friendly conversations where you're genuinely helping people solve problems. I'll show you three specific scenarios every introvert faces in sales, plus the mindset shifts and practical scripts that make all the difference. Whether you're terrified of networking events, struggle with self-promotion online, or freeze up when it's time to ask for the sale, this episode gives you a roadmap to sell authentically without changing who you are.What you'll learn:How to use AI tools to practice and warm up before sales callsThe exact reframes that eliminate “commission breath” and sales anxietyWhy being introverted is actually your secret weapon in sales conversationsThree scenarios with actionable scripts you can adapt to your personalityHow to turn networking from draining to energizing (yes, really!)The mindset shift that makes self-promotion feel natural and helpfulIf you've been avoiding sales because it feels pushy or fake, this episode will show you how to lean into your introverted strengths and build the business you want, one genuine conversation at a time.

In this second part of my conversation with sales trainer Eric Shulman, we get tactical. Eric lays out clear steps for solopreneurs who want to stop circling in indecision and actually build momentum in their sales. From reframing networking and prospecting to tackling “head trash” and learning to make quick decisions, this episode is packed with real strategies you can use right away.

In this episode of My Solopreneur Life, I sit down with sales trainer Eric Shulman to break down why selling isn’t about pressure or pushing—it’s about connection. Eric shares how to replace fear with curiosity, why “radical empathy” changes everything, and how to build instant trust without coming off like every other salesperson.

In this episode, I dive deep into one of the toughest challenges every solopreneur faces: overcoming the fear of rejection when approaching sales conversations. I unpack the six mindset shifts and tactical steps that have truly helped me transform every "no" into valuable feedback and greater confidence. From normalizing anxiety and learning to detach personal meaning from rejection, to reframing each conversation as an opportunity for growth, I'm sharing both my wins and stumbles so you can build your own resilience in client outreach.

In this episode, I get real about why my financial mindset used to sabotage my sales and how I changed it. I share personal stories of fear and financial stress, how those anxieties bled into client conversations, and the turning point that let me sell with calm clarity. You'll hear actionable strategies for separating your financial reality from your selling energy, helping you show up confidently and attract the right business, not just chase it out of desperation.Key Takeaways:Recognize how financial stress quietly erodes sales confidenceGet practical about tracking and managing business and personal expensesLearn ways to shift from a scarcity mindset to an abundance mindsetUse a journaling exercise to re-center before sales callsFind support such as a CPA, advisor, or trusted friend to gain perspective and lighten the burden

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 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 else2. Passion - be clear on what you want to do3. Mindset - secure a growth mindset4. Relationships - your network is your gateway to success5. Invest - get a coach to guide you along your journey6. Learn - keep your skills sharp, study your industry7. Action - Just do it and make each action move your business forward

Meet Harry Travis, solopreneur and ex-specialty pharmacy executive turned community building and network genius. Harry is a client of mine who I met in late 2024. He has a wonderful two part story (part one is episode 209, part two is episode 210) of his journey into solopreneurism and shares detailed challenges and realizations he faced when he launched his new consultancy and membership business.

In this episode, I sit down with my client—and now friend—Harry Travis, who shares his inspiring journey from a long corporate career in pharmacy and healthcare to building his own solopreneur business. Harry talks about making the leap after leaving CVS Caremark, reinvesting in himself through executive education, and how classic networking led to the creation of the RX Roundtable—an ever-growing network for independent pharmacy and healthcare professionals. We discuss the importance of identifying your true value, leveraging relationships, and the courage it takes to put yourself and your business out there when starting over on your own.Harry wraps up our first conversation with three actionable prompts for anyone ready to begin their solopreneur adventure: get clear on the value you offer, don’t go it alone—lean on your network for support and encouragement, and have the courage to get visible, even when it feels scary. Stay tuned for part two, where we dig even deeper!

Before anything else, when starting a business or leveling up a business, solopreneurs must have a strong network. Building relationships as an ongoing effort will lead to more opportunities for people to help you, you to be of service to others, and for people to know about you and the problems you solve.Most importantly, they should know the kind of person you are. That you have integrity in your actions and deliver results on your promises. Your relationships represent how you and your personal brand are perceived in the marketplace, so put in the time not just by creating content, but buy being a person who cares about others and makes the effort to show it by interacting, engaging and growing relationships.

Your story will make or break your solopreneur business success, depending on how you use it. If you are intentional about creating a new story about your business, how you sell, how you serve clients, how you deliver value, how you market and promote your business, you'll find each area rewards you with positive results. If your story is defeatist, negative, or self-demeaning, like you're not good enough, and you keep telling that story, you'll see the results in struggle, challenges, and difficulty growing your business. The great news is you can choose the path you want and it's as easy as writing/telling a new story.

Here’s an easy three-step process to blast through any resistance keeping you from starting a new business, project, or any endeavor you want to accomplish.

Starting a new business is exciting and intimidating, especially if you've left the corporate world or a longstanding job and are at a loss on where or how to start. But before you figure out the practical stuff, you need to get your mindset up to speed with where you want to go. In this episode, I talk about the fears and diminishing beliefs that can thwart your progress from the get-go and how to understand their purpose and how to move past them to get your business on the right track.

Learn how to incorporate AI to help you visualize positive outcomes for your business. Your success begins with your imagination, and when you focus on what you want, lean into positive outcomes, before you know it, magical things happen. And, you can use AI to help craft some very creative scenarios that you can deliberately think about and visualize to stay positive and open to inspired action that moves you toward what you want for yourself and your business.

Let’s talk about how to use the right AI prompting to get specific marketing content. A process I use is to reverse engineer an end result—closing a new client—so you can develop the right kind of content for your inbound marketing campaigns.

This episode is about starting a consulting or service-based business—especially if you’re riffed from a long-term corporate role—and how to not miss the most important part of designing your business versus just doing the same old same old but on your own.

What a wonderful first season of My Solopreneur Life! I’ve had a blast but I’m just getting warmed up. In this episode I share my thanks and tease what will be the theme for season two: starting! We all need help there, for sure. You’re gonna love season two!

How I am now using AI and leverage it in my solopreneur practice. It’s time we all get used to the idea that AI is here to stay, and lean into how it can help us work more efficiently as well as how we can pass along the savings to our clients.

Being your natural self will become your secret weapon in the Age of AI. It will also allow you to further distinguish yourself in an ever-changing competitive marketplace, whether among other solopreneurs or small businesses attempting to capture your audience and clients. Today I’ll share how I’ve evolved my natural self, and how I (frankly) don’t give a d&!$m, Scarlet, what others think as I’m out to do good and inspire others to have real, authentic fun in their business being themselves.

Sales can be the biggest business challenge for solopreneurs. Although I've claimed I'm a reluctant marketer, I love sales. Never used to feel that way, but over the years, I've come to realize that sales is about relationships. If you care about helping others, sales should come easily for you. In this episode, I give you a quick and easy little tip that will make your sales process flow.