4 Powerful Questions for HeartBased Solopreneurs (beyond fear)

Immerse yourself in a transformative exploration of impactful questions tailored for heart-based solopreneurs. Uncover profound insights and reflections in this thought-provoking deep dive into the realm of heart-centered entrepreneurship.

Quote: “The value projected through your offerings reflects your internal commitment to growth. The realization of your endeavor’s worth is a reflection of your acknowledged worthiness.”


Imagine This:

Sally Sue, a dedicated heart-based solopreneur, sits in her favorite armchair, basking in the glow of the sunrise spilling onto the pages of her journal. Her business, born out of a love for holistic wellness, has been her heart’s work, yet she finds herself at a standstill, unable to break through as expected. As the morning light warms her face, she feels the contrast in her heart—cool with doubt and uncertainty.

But today is different. Today, Sally is not here to plan or strategize; she’s here to confront the questions she has skillfully avoided—the kind that unlocks hidden doors to uncharted territories within her spirit. She begins with a deceptively simple query: “What would I do if I knew I couldn’t fail?” This question acts as a key, turning in a lock she didn’t realize was there.

Shadow of Self-Doubt

Unburdened by the whispers of fear or the heavy cloak of “practicality,” Sally allows herself to imagine. Visions of leading workshops, speaking confidently about her craft, and authentically connecting with clients without the shadow of self-doubt start to color her thoughts.

In this dance of deep self-reflection, Sally encounters a version of her life that crackles with potential, a departure from the narratives of limitation she has carried. It’s a life where past failures don’t define her worth or dictate her future.

Kahlil Gibran: “Your pain is the breaking of the shell that encloses your understanding.”


This moment of profound introspection is where many heart-based solopreneurs stand at the crossroads of transformation. The power of questioning our assumptions and fears lies not only in asking the questions, but also in creating a brave space for the answers to emerge.

As we embrace this journey together, consider that, like Sally, you too possess the courage to uncover a path that exists beyond your fears—a path waiting for your audacious first step.

Now, hold on to that vision as we dive into four powerful questions that can reshape your solopreneurial journey and redefine the narrative of your life.

The 4 Questions:

In the stillness of contemplation, a collection of questions can stir the oceans within us—unveiling answers that whisper guidance to our entrepreneurial spirits. With focused attention, these inquiries can transform our approach and catalyze an evolution in our professional tapestries. Let us gather our inner courage and contemplate the following:

1. What Would I Do If I Knew I Couldn’t Fail?

This is not a pathway to unrealistic dreams, but a summons to possibility, stripping away the fears that often cloud our most profound potential. In the answer, you unearth the actions impervious to fear, aligned with your deepest truths, and driven by passion, not merely results.

2. How Would I Spend My Time If I Had A Billion Dollars?

Amidst the strengths of financial freedom lies the liberty to choose. Here, your genuine interests come alive, uninhibited by necessity, echoing the core passions that should govern your solopreneurial journey regardless of your account balance.

3. Where And How Am I Sabotaging My Success?

By examining our own barriers, we expose the underlying beliefs dictating our decisions. In acknowledging these invisible scripts, heart-based solopreneurs invoke awareness—our first step towards elevated paths of authenticity and abundance.

4. What Assumptions Am I Making About The Limitations I’m Experiencing?

Limitations often wear the mask of objective truth, yet they are birthed from our subjective perceptions. Challenging these assumptions empowers us to redefine the edges of our capacities and ventures.

Bhagavad Gita: “You have the right to work, but never to the fruit of work.”

Your Best Year to Come?

In January 2024, we begin the launch of the Deep Divers groups (DDG) — a journey for those inspired by the appeal of heart-based existence and empowered by community. Within DDG, we nurture the wisdom to question freely, courageously explore vulnerability, and harness the profound influence that such wisdom weaves into our solopreneur visions and personal conscious evolution.

DDG merges spirituality with strategy, blending the essence of who you are with the expression of what you create. It is a space of purposeful engagement, reflecting the change you seek to manifest in your work-life balance. This is an invitation for solopreneurs who aim to navigate their endeavors not only with intellect but also with intuition as an equally valued companion in the process of open conversation and courageous progress.

The Upanishads: “As is the human body, so is the cosmic body. As is the human mind, so is the cosmic mind.”

Your Willingness to Explore

The value projected through your offerings reflects your internal commitment to growth. The realization of your endeavor’s worth is a reflection of your acknowledged worthiness. And the impact of your solopreneurial journey is a testament to your willingness to explore the vast field of the unknown.

If even a hint of this resonates with your heart, I warmly invite you to learn more about DDG and apply to join our collective unfolding. Consider this a moment to greet the upcoming year as a threshold of transformation — an adventure that calls your name.

I look forward to connecting with you, witnessing your radiance, and supporting your unwavering steps towards what calls you forward. May your courage know no bounds, your potential flourish abundantly, and your journey be as fulfilling as the peace within you.

Dalai Lama: “Happiness is not something ready-made. It comes from your own actions.”

In service of your unfolding,

— Tiger Singleton


P.S. Illuminate your path and redefine success in a way that aligns with your heart. Click here to learn more about DDG and embark on an authentic journey of success as a heart-based solopreneur. Love and courage to you all.



SGT Solopreneur Group Training

Rise up… honor your value, and share your heart with the world.

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