Podcasts > Creating Confidence with Heather Monahan > Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

By Heather Monahan

In this episode of Creating Confidence, Italian-American attorney Davide De Pierro shares his journey from traditional legal practice to online content creation. At age 37, he began creating TikTok videos about relationships from his car, which unexpectedly went viral. While maintaining his family law practice as a safety net, he has expanded into storytelling through his audiobook "The Letters I Never Sent."

De Pierro discusses how creators can build confidence through action rather than waiting for perfect circumstances. He explores the importance of authenticity in content creation, explaining how staying true to oneself leads to stronger audience connections. The episode covers his approach to balancing his established legal career with his creative pursuits, and how he navigates the transition between these different professional spheres.

Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

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Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

1-Page Summary

Davide's Personal and Professional Background

Davide De Pierro's Italian-American heritage has profoundly influenced his life choices. Following in his family's footsteps, he became an attorney in the family law practice, working alongside his father and brother. Beyond his legal career, Davide nurtures a private passion for storytelling, inspired by his father's entrepreneurial journey and belief that "it's never too late to be who you might've been."

Davide's Transition To Becoming an Online Content Creator

Initially hesitant to create content, especially at age 37, Davide began making TikTok videos from his car at his girlfriend's encouragement. His authentic discussions about relationships quickly gained traction, leading to unexpected viral success. While his online persona represents a specific side of his personality—the one his friends in New Jersey know well—it remains genuine, earning support from both family and former partners.

Davide's Journey as an Aspiring Author

Davide expanded his creative pursuits by publishing an audiobook titled "The Letters I Never Sent," a collection of writings spanning a decade that explores themes of love and heartbreak. Despite his initial reservations, the audiobook has received enthusiastic response from thousands of listeners who find it healing and relatable. This success has helped Davide transition from being perceived as just a comedian to establishing himself as a serious storyteller.

Advice For Career/Creative Transition

Drawing from his experience, Davide emphasizes that self-doubt shouldn't prevent action, as confidence often grows through doing. He encourages creators to maintain authenticity rather than imitate others, noting that genuine content creates stronger audience connections. Currently, Davide is gradually transitioning from his legal career while keeping it as a safety net, demonstrating his practical approach to pursuing creative ambitions.

1-Page Summary

Additional Materials

Clarifications

  • Davide De Pierro is an Italian-American attorney who works in the family law practice alongside his father and brother. He also has a passion for storytelling inspired by his father's entrepreneurial journey. Davide's personal and professional background reflects a blend of legal expertise and creative pursuits.
  • Davide's transition to becoming an online content creator signifies a shift from his traditional legal career to a more creative and personal outlet. This change allowed him to explore a new platform, TikTok, to share his thoughts on relationships and connect with a broader audience. The unexpected viral success of his content helped him establish a unique online persona while staying true to his authentic self. This transition showcases Davide's willingness to embrace change and pursue creative endeavors outside his initial professional path.
  • Davide published an audiobook titled "The Letters I Never Sent," sharing writings on love and heartbreak. The audiobook resonated with thousands of listeners, who found it healing and relatable. This success helped Davide shift from being seen as a comedian to establishing himself as a serious storyteller. The positive reception of his audiobook encouraged Davide to continue pursuing his creative endeavors.
  • Davide's advice for career/creative transitions emphasizes the importance of taking action despite self-doubt, as confidence often grows through experience. He encourages creators to stay true to themselves and create authentic content to build stronger connections with their audience. Davide is gradually shifting from his legal career to focus more on his creative pursuits while keeping his legal work as a safety net. This practical approach allows him to pursue his creative ambitions while maintaining stability.
  • Davide is slowly shifting away from his legal profession to focus more on his creative endeavors, like content creation and writing. He is maintaining his legal work as a safety net while exploring and expanding his presence in the creative field. This transition involves balancing his legal responsibilities with his growing creative pursuits, allowing him to explore new opportunities while ensuring stability. Davide's approach reflects a strategic and cautious progression towards pursuing his creative passions.

Actionables

  • Explore your heritage to guide life decisions by researching your family history and identifying values and traditions that resonate with you, then consciously incorporate these into your daily choices, such as cooking a traditional dish weekly or adopting a value as a personal mantra.
  • Share your personal journey through social media by starting a blog or video series that captures your unique experiences, challenges, and triumphs, using storytelling to connect with others who might find inspiration or solace in your narrative.
  • Embrace a new hobby or interest later in life by setting aside time each week to learn and practice something you've always wanted to do, whether it's playing an instrument, painting, or writing, to demonstrate that personal growth and change can happen at any age.

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Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

Davide's Personal and Professional Background

Davide De Pierro offers insight into his life, highlighting how his Italian-American heritage has shaped his values and career choices, and his private pursuit of storytelling reflects a belief in continuous self-reinvention influenced by his father.

Italian-American Roots Shape Davide’s Values

Davide emphasizes the importance of family in his Italian culture, reflecting a tight-knit dynamic where family members frequently do things together. He exhibits pride in his lineage and how it informs his approach to both personal and professional life.

Davide Became an Attorney Like His Father and Brother in the Family Law Practice

Davide’s decision to pursue law was deeply influenced by his familial connections. He humorously compares joining the family law practice to taking over a family-run pizzeria, indicating the natural progression of following a family trade. He worked alongside his father, brother, and at one point, his best friend.

Davide's Private Passion For Storytelling and Writing

In addition to his legal career, Davide harbors a private passion for storytelling and writing. This interest reflects a broader perspective on life and career choices, shaped significantly by his father's life narrative.

Davide's Entrepreneurial Father Shaped His Mindset on Career Changes

His father, starting a business in Italy at age 18 with little more than a high school diploma and basic Italian language proficiency, embarked on a diverse career path, i ...

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Davide's Personal and Professional Background

Additional Materials

Counterarguments

  • While Davide's Italian-American heritage may shape his values and career choices, it's also possible that other factors such as personal interests, societal influences, or educational experiences have played a significant role.
  • The importance of family in influencing decisions can sometimes lead to a lack of exploration of personal desires or societal pressures to conform to family expectations.
  • Following in the footsteps of family members in a career path might limit exposure to diverse professional experiences and could potentially hinder personal growth if the choice is not fully aligned with one's own passions and interests.
  • A private passion for storytelling and writing, while enriching, might not always translate into professional success or fulfillment if not actively pursued or integrated into one's career.
  • Being influenced by a parent's entrepreneurial background is valuable, but it's also important to acknowledge that individual capabilities, resources, and economic conditions play a crucial role in one's ability to change careers or start a business.
  • The belief in continuous self-reinvention, while positive, may not always be practical for everyone, as it can sometimes ignore the realities o ...

Actionables

- Explore your family tree to understand how your heritage influences your values and career choices by creating a visual map that includes professions, hobbies, and values of your ancestors, then reflect on how these elements resonate with your current life decisions.

  • By visually mapping out your family history, you can identify patterns and influences that have shaped your own path. For example, if you discover a lineage of teachers, you might explore whether education and mentorship are important to you and how you can incorporate these values into your career.
  • Start a "Change Journal" to document your thoughts and feelings about personal and professional change, using it as a tool to embrace the idea that reinvention is possible at any stage in life.
  • Keeping a journal focused on change can help you become more aware of your own capacity for reinvention. For instance, if you're considering a career shift, use the journal to record the steps you're taking, the fears you're facing, and the inspirations you're drawing from, which can help you navigate the process with more clarity and confidence.
  • Dedicate time each week to a "hidden passion project" that aligns with your privat ...

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Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

Davide's Transition To Becoming an Online Content Creator

Davide's journey to becoming an online content creator started with hesitation but led to unexpected success and a newfound identity on TikTok.

Hesitant Davide, Shy About Creating Content, Was Encouraged by a Girlfriend to Try Tiktok Videos

Davide, originally "chronically offline" and shy about the idea of making TikTok videos, especially at the age of 37, was encouraged by a girl he was dating to explore the platform. He began creating content from the privacy of his car, too ashamed at first to let his girlfriend watch him film. Despite this initial embarrassment, he found that making videos in his car not only provided him with privacy but later became a recognized part of his brand.

Davide's Spontaneous Car Videos on Relationships Rapidly Gained a Positive Following

Davide's content, which consisted of him simply speaking his mind about topics similar to those he would discuss with his friends, quickly received rapid and positive attention. This type of growth was considered uncommon, signifying that his authentic voice resonated with a wide audience.

Davide's Online Persona Authentically Represents a Specific Side of Himself

Friends and Family Shocked by Davide's Success, now Supportive

While Davide De Pierro's online persona isn't a completely different character, it showcases the side of him that he reveals when he's with friends in New Jersey. Although he behaves differently as a lawyer in court, the person in the videos is indeed a facet of his true self. Over time, as he gained experience, his voice and composure evolved, which can be observed when comparing his newer content to videos from five months prior.

Davide speaks of receiving mainly positive feedback from his viewers and maintains ...

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Davide's Transition To Becoming an Online Content Creator

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Actionables

  • You can start creating content in a space where you feel comfortable to establish a unique setting that resonates with your audience. For instance, if you're an avid gardener, begin filming your gardening tips from your greenhouse or garden. This not only provides privacy but also sets a consistent backdrop that becomes recognizable to your viewers.
  • Experiment with sharing different facets of your personality online to find what truly connects with your audience. If you're known among your friends for your sense of humor, try incorporating that into your content. Record a series of short, humorous skits related to your niche, and monitor the audience's response to see if this authentic expression helps build a following.
  • Encourage feedback from your personal network to ...

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Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

Davide's Journey as an Aspiring Author

David De Pierro's transition from lighthearted content creator to profound storyteller comes to life as he publishes his long-held private writings in the form of an audiobook.

"The Letters I Never Sent" as Audiobook

The audiobook, titled "The Letters I Never Sent," showcases Davide's emotional side as he explores themes of love, relationships, and heartbreak—an expressive departure from his more humorous video content. With writings collected over a decade, Davide sought to provide an intimate experience for his followers, believing that an audio format would leverage his familiar voice to add depth to his heartfelt stories.

Davide was hesitant to share his writing, expecting that it might not receive much attention. To his surprise and delight, his audiobook has been welcomed with enthusiasm by thousands of listeners who have found it to be beautiful, healing, therapeutic, and relatable. People have resonated so strongly that they are asking for a printed version and are eagerly inquiring about future works or sequels.

Overcoming Reluctance and Embracing Storytelling

Davide, who didn't want to be pigeonholed as just a comedian, has made a conscious effort to redefine himself. Known for his one-minute videos, Davide wanted to transcend that medium and share profoundly resonating stories that demonstrate his passion for storytelling.

Despite his initial reluctance to share his writings, Davide now receives nothing but love and positive feedback for his work. His audience has expressed a connection to the book, appreciating its worth and asking for more content, which has been both exciting and validating for Davide.

He acknowledges that while the book is primarily a work of fiction, it is based on his own experiences and observations, which has sparked speculation that it may be his memoir. Davide finds amusement in this interpretation but hopes that regardless of how it is perceived, readers will find enjoyment and univers ...

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Davide's Journey as an Aspiring Author

Additional Materials

Actionables

  • Explore your multifaceted self by starting a personal journal where you write from different perspectives, such as the comedian, the philosopher, or the romantic in you. This exercise can help you discover and embrace the various aspects of your personality, much like Davide embraced his storytelling side. For example, on Mondays, you could write a humorous anecdote, while on Thursdays, you might pen a heartfelt letter to someone you care about, even if you never send it.
  • Create an audio diary to capture your emotions and experiences in your own voice. Record entries that express your feelings about daily events, relationships, or personal growth. Listening back to these recordings can provide a deeper understanding of your emotional journey and may even inspire you to share your stories with others in the future.
  • Draft a fictional short story based on a rea ...

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Start Before You’re Ready and Let Confidence Catch Up with Davide “Davi” De Pierro

Advice For Career/Creative Transition

Davide De Pierro shares his personal journey and insights, providing advice to those considering a shift in their professional or creative life. He addresses the common fears and reservations that one may experience when undertaking such changes.

Davide Urges Trying New Things, as Doubts Fade Once You Start

Davide emphasizes that the stories we tell ourselves about what is impossible are just that—stories. These narratives, rooted in doubt and fear of embarrassment, are not a reflection of reality. He shares from his own experience of creating content for platforms like TikTok that one must not wait for doubts to disappear before beginning. Instead, Davide suggests that starting even when unsure is beneficial, and that taking action can actually grow confidence and diminish doubts over time.

He also encourages people to pursue diverse paths and take risks, given that the worst-case scenario is one ends up where they started, implying that there is much more to gain than to lose by trying new endeavors. Davide believes we shouldn't hesitate to chase different opportunities because life is long and full of possibilities.

Worst-Case: Ending Up Where You Are, So Risk Pursuing Your Passions

In his advice, Davide highlights that time will pass regardless of our actions, so it’s better to use it to try new things. He reasons that one will either discover something new or end up back where they started, making a compelling case for taking leaps toward one's dreams. He assures that rarely do people regret pursuing their passions and suggests that, by taking risks, one has the opportunity for growth and fulfillment.

Davide Urges Creators to Be Authentic, Not Imitators, to Genuinely Connect With Their Audience

Stressing the importance of authenticity, Davide encourages creators to be genuine in their content, as this fosters a real connection with their audience. He cautions against the temptation to copy others and underscores that an original voice is more effective than an imitation. This urges creators to remain true to themselves as a means of distinguishing their work and resonating wit ...

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Advice For Career/Creative Transition

Additional Materials

Counterarguments

  • While starting new endeavors can help overcome doubts, it may not always be the case for everyone; some individuals may find that their doubts intensify with new challenges.
  • Taking risks can lead to growth, but it can also lead to setbacks or failures that can be difficult to recover from, both emotionally and financially.
  • Time is a limited resource, and using it to try new things without a clear strategy or goal can sometimes result in wasted time and missed opportunities elsewhere.
  • Some people do regret pursuing their passions, especially if it leads to significant personal or financial loss, or if the pursuit negatively impacts their relationships or health.
  • Authenticity is important, but there are instances where adapting to market trends or audience preferences can also be a strategic move for content creators.
  • An original voice is valuable, but sometimes learning from and incorporating elements from successful creators can be a practical approach for those starting out.
  • A gradual transition from a stable career to a ...

Actionables

  • Start a "30-Day Challenge" where you commit to trying one new small activity each day to build the habit of embracing uncertainty. This could be as simple as cooking a new recipe, taking a different route to work, or striking up a conversation with a stranger. The key is to make it manageable and to reflect on how each new experience affects your confidence and outlook.
  • Create a "Passion Project Hour" in your weekly schedule where you dedicate time to work on something you're passionate about, separate from your main job or responsibilities. This could be writing, painting, coding, or any other creative endeavor. Use this time to explore and express your authentic voice without the pressure of it being your primary source of income.
  • Develop a "Skill Swap" with friends or commun ...

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