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, I talk with Natalie Benamou, founder of HerCsuite®, 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

In this episode, I continue my conversation with Harry Travis as we explore how his passion project—the RxRoundtable—grew from a casual network into a thriving, revenue-generating business. Harry describes how organic growth and genuine community-building led to unexpected scaling challenges, and what it took to make the leap from hobby to legitimate solopreneur venture. We talk through the infrastructure decisions he faced, the importance of finding the right partners to help evolve his idea, and how supporting others in the industry turned out to be a win-win for both business and personal fulfillment. Harry's biggest takeaway: there’s huge value in building real fellowship, staying responsive, and remembering that every encouraging reply can make a difference.

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.

Kicking off season two in this episode which is dedicated to starting. I share more about my family members and how their entrepreneurial DNA got them to start their businesses and projects. Starting is a little appreciated segment of the creative process where we conjure something magical that will be the bridge to us making money, helping others, and doing work we love. But it all has to begin with an idea that will trigger the starting gun. I was lucky to be surrounded by a lot of entrepreneurial starters who did work their way after realizing they weren't happy unless they were working for themselves.

Episode 16 of Season 1 - A wrap of a great first season and what you can expect for Season 2, which is all about starting. We all need help in that department!