Embracing Reinvention: Craig Siegel's Journey from Wall Street to Personal Development
Nick Dougherty • July 17, 2024
A man with a beard is standing with his arms crossed and smiling.

In this blog, Craig Siegel shares his inspiring story of leaving Wall Street to pursue personal development, finding true fulfillment through spirituality and coaching. Craig details his transition from a successful Wall Street career to a more meaningful life centered on personal growth. Join us as he reflects on the challenges, revelations, and triumphs that shaped his journey to self-discovery and purpose.


Starting Out: Life on Wall Street

Hello everyone, Craig Siegel here. Let me take you back to where it all began – my journey on Wall Street. For 13 years, I immersed myself in the fast-paced environment of Wall Street. The thrill of success and the allure of financial rewards initially drew me in, but deep down, I felt a sense of unfulfillment creeping in.


The relentless stress and pressure of the financial world began to take a toll on me. Despite the initial excitement, I realized that something was missing. I yearned for a deeper, more meaningful purpose beyond the numbers and transactions.


It was during a particularly tough period in my life that I had a moment of clarity. Going through a toxic relationship and facing my dad's cancer diagnosis shook me to the core. I realized that I was merely existing, not truly living. In the midst of this turmoil, I turned to running as a form of solace and self-discovery.


Running became more than just a physical activity; it became a metaphor for pushing through challenges and embracing life with renewed vigor. Each marathon I completed symbolized my resilience and determination to break free from the shackles of monotony.


When the pandemic swept across the globe, it served as a catalyst for introspection and reassessment. I delved into spirituality and personal development, seeking a deeper connection with something greater than myself. This pivotal moment led me to the realization that personal development wasn't just a passion – it was my true calling.


Out of this realization, CLS (Cultivate Lasting Symphony) was born. Starting from scratch, with no followers or connections, I embarked on a journey to share my insights and experiences with the world. Through consistent effort and authenticity, CLS blossomed into a platform that resonated with individuals seeking growth and fulfillment.


Spirituality played a profound role in shaping my path. It instilled in me the belief that our souls are on a continuous journey of growth and learning. Embracing fear as a catalyst for personal evolution, I learned to view challenges as stepping stones towards self-discovery and enlightenment.


Discovering my purpose was a transformative moment in my life. It infused each day with direction and motivation, turning obstacles into opportunities for growth. With a clear sense of purpose, every endeavor became a meaningful step towards a more fulfilling existence.


Looking back, the decision to transition from Wall Street to personal development stands as a pivotal moment in my life. While the journey was fraught with uncertainties and challenges, it ultimately led me to a place of profound fulfillment and purpose. By confronting my fears, staying true to my calling, and embracing spiritual practices, I found a path that resonated with my soul.


A Tough Time

During a challenging period in my life, I faced various obstacles, including toxic relationships and family health issues. These struggles weighed heavily on me, leaving me feeling lost and unfulfilled. However, amidst the darkness, I found solace in running and embarked on a journey of self-discovery.


Running became more than just a physical activity; it became a form of therapy for me. It allowed me to clear my mind, push my limits, and connect with my inner self. With each stride, I felt a sense of liberation and empowerment, turning my pain into fuel for personal growth.


Despite the hardships I faced, I refused to let them define me. Instead, I saw them as opportunities to learn, evolve, and transform. Every challenge became a stepping stone towards a better version of myself, guiding me towards a path of resilience and strength.


The Pandemic: A Chance to Reassess

During the pandemic, I had a unique opportunity to pause, reflect, and reevaluate my life priorities. The fast-paced nature of everyday life came to a sudden halt, giving me the space to delve deep into what truly mattered to me. It was a time of introspection and self-discovery, a chance to realign my values and goals.


Exploring spirituality became a significant part of this journey. I delved into practices that connected me to something greater than myself, seeking solace and guidance in the midst of uncertainty. This exploration not only provided me with comfort but also opened up new avenues for personal growth and development.


One of the pivotal moments during this period was the founding of CLS (Cultivate Lasting Symphony) as a platform for coaching and speaking. It was born out of a deep desire to share my learnings, experiences, and insights with others who might be on a similar path of self-discovery and reinvention. CLS became a space where I could offer support, inspiration, and practical guidance to those seeking to navigate their own transformative journeys.


Reevaluating life priorities, exploring spirituality, and establishing CLS as a platform for coaching and speaking were transformative experiences that shaped my path forward. They allowed me to embrace change, find purpose, and connect with a community of like-minded individuals dedicated to personal growth and fulfillment.


Building CLS

Hey everyone, Craig Siegel here. Today, I want to take you through the journey of building CLS (Cultivate Lasting Symphony) from scratch, with no connections, to establishing a successful brand with a strong community. It's been a remarkable ride filled with challenges, growth, and incredible moments of connection.


Starting from Scratch with No Connections

When I first embarked on this journey, I had no followers, no famous friends, and no industry connections. It was just me, my vision, and a burning desire to make a difference in the world of personal development. I knew that building something meaningful required starting from the ground up, even if it meant facing uncertainty and doubt.


I began by putting out content that reflected my authentic self. It wasn't always perfect, but it was genuine. I shared my thoughts, experiences, and insights with the world, hoping to resonate with even just a few individuals who were seeking guidance and inspiration.


Consistent Content Creation and Growth

Consistency became my mantra. Day in and day out, I showed up, creating content, engaging with my audience, and refining my message. It was a gradual process, filled with ups and downs, but I remained steadfast in my commitment to growth and learning.


Through consistent content creation, I started to see small wins. A few followers turned into a community, speaking engagements started trickling in, and opportunities began to unfold. Each piece of content was a building block, shaping the identity of CLS and resonating with those who sought personal development and spiritual growth.


Establishing a Successful Brand with a Strong Community

As CLS continued to grow, I realized the power of community. It wasn't just about me anymore; it was about the individuals who believed in the message, the vision, and the journey we were on together. Building a successful brand wasn't just about numbers; it was about impact, connection, and transformation.


Today, CLS stands as a testament to the power of authenticity, consistency, and community. We have a top podcast sponsored by Mark Cuban, speaking engagements that span the globe, a bestselling book that resonates with readers, and a community that supports, uplifts, and inspires each other.


Building CLS from scratch wasn't easy, but it was worth every moment of doubt, fear, and uncertainty. It taught me the value of perseverance, authenticity, and the unwavering belief that with dedication and passion, anything is possible.


As I reflect on this journey, I am grateful for every challenge, every setback, and every triumph. They have shaped CLS into what it is today—a beacon of hope, inspiration, and growth for all those who seek a more fulfilling life.


Thank you for being a part of this incredible journey. Together, we will continue to cultivate lasting symphonies of change, growth, and transformation.


Spiritual Growth and Higher Thinking

As I reflect on my journey from Wall Street to personal development, I am reminded of the profound impact spirituality has had on my growth and mindset. Belief in soul growth and facing fears are pivotal aspects of this transformation, allowing me to turn stress into opportunities for personal and spiritual development.


Embracing spirituality as a guiding force has been instrumental in shaping my perspective and driving me towards a more fulfilling life. It's not just about overcoming challenges; it's about evolving and aligning with a higher purpose.


Belief in Soul Growth and Facing Fears

One of the core principles that have guided me through this journey is the belief in soul growth. I firmly believe that our souls are on a continuous journey of learning and evolving. By acknowledging this belief, I have been able to approach challenges with a growth mindset, viewing them as opportunities for spiritual advancement.


Facing fears has been a transformative practice for me. Instead of shying away from fear, I have learned to confront it head-on. By embracing my fears and understanding the lessons they hold, I have been able to transform stressful situations into catalysts for personal growth.


Turning Stress into Growth Opportunities

Stress is inevitable, especially in high-pressure environments like Wall Street. However, I have learned to reframe stress as a potential growth opportunity. By shifting my perspective, I can extract valuable lessons from stressful situations and use them as stepping stones towards personal and spiritual development.


Every challenge presents an opportunity for growth. By embracing stress as a natural part of life and viewing it as a chance to learn and evolve, I have been able to navigate difficult circumstances with resilience and grace.


Embracing Spirituality as a Guiding Force

Spirituality has become the compass that guides my decisions and actions. By embracing spirituality as a guiding force, I have found clarity, purpose, and inner peace. Practices like meditation, prayer, and self-reflection have deepened my connection to something greater than myself.


Through spirituality, I have discovered a profound sense of purpose that transcends material success. It has allowed me to align my actions with my values and aspirations, leading to a more meaningful and fulfilling existence.


Finding Purpose

As I reflect on my journey from Wall Street to personal development, I realize that finding purpose has been the cornerstone of my transformation. Discovering personal purpose and direction has not only given me clarity but also a sense of fulfillment that I never experienced in my previous career.


One of the key lessons I've learned is to see challenges as growth opportunities. Instead of shying away from obstacles, I now embrace them as chances to learn, evolve, and become a better version of myself. Every setback is now viewed as a stepping stone towards personal and professional growth.


Living a more fulfilling and meaningful life is not just a goal; it's a daily practice. By aligning my actions with my values and purpose, I have found a deep sense of contentment and joy that transcends material success.


Embracing Purpose Every Day

For me, finding purpose is not a one-time event but an ongoing journey. It's about waking up each day with intention, passion, and a commitment to making a positive impact on the world around me. Whether it's through coaching, speaking, writing, or simply being present for others, I strive to live each moment with purpose.


Transforming Challenges into Opportunities

Every challenge I face is an opportunity to grow and evolve. Instead of being daunted by adversity, I now welcome it as a chance to test my resilience, creativity, and determination. By reframing challenges as opportunities for personal development, I have unlocked new levels of potential within myself.


Cultivating Meaning in Everyday Life

Living a fulfilling life is not about grand gestures or momentous achievements; it's about finding meaning in the everyday moments. Whether it's a quiet moment of reflection, a heartfelt conversation with a friend, or a small act of kindness, I seek to infuse every aspect of my life with purpose and significance.


The Power of Purpose

As I conclude this journey from Wall Street to personal development, I am reminded of the transformative power of purpose. By discovering my personal mission, embracing challenges as opportunities, and living with intention, I have found a deeper sense of fulfillment and joy than I ever thought possible. My hope is that my story inspires you to embark on your own quest for purpose and meaning, knowing that the journey itself is as rewarding as the destination.


As I conclude my story of leaving Wall Street behind for a life of personal development and purpose, I invite you to reflect on your own journey. Embrace change, face your fears, and seek out your true calling. Remember, the path to fulfillment may not always be easy, but it is always worth it. Let's continue to grow, learn, and inspire each other on this remarkable journey of self-discovery and transformation.


Frequently Asked Questions


Q: How did you overcome the fear of leaving a stable job? 

A: Understanding that fear is a tool for growth was key. I viewed fear as a flashlight highlighting my next level of expansion. Embracing fear and stepping out of my comfort zone was daunting but essential for my growth.


Q: What role did spirituality play in your journey? 

A: Spirituality was central to my transformation. It helped me connect with a higher consciousness, receive divine guidance, and view challenges as opportunities for growth. The practice of Kabbalah and other spiritual teachings provided a blueprint for achieving lasting fulfillment.


Q: How do you stay motivated and consistent? 

A: Consistency is a superpower accessible to everyone. Building a routine, setting clear goals, and staying committed even when progress seems slow are crucial. Celebrating small victories and maintaining a strong connection to my purpose also keep me motivated.


Q: What advice do you have for someone looking to reinvent themselves? 

A: Give yourself permission to be less than perfect. Take messy action, be consistent, and build a community. Don't seek validation from others; instead, focus on your growth and authenticity. Embrace fear as a sign of where you need to go next and stay committed to your purpose.


Q: How do you balance practical actions with spiritual growth? 

A: I believe in marrying practical steps with spiritual practices. Setting clear goals, taking consistent action, and using spiritual tools like meditation, visualization, and affirmations create a powerful synergy that accelerates growth and fulfillment.

Join The Brotherhood
By Nick Dougherty December 29, 2025
The Inversion Framework That Will Dominate 2026 Marketing didn’t stop working. Humans adapted. That distinction matters more than any algorithm update, ad strategy, or funnel hack being sold right now. Most people believe marketing broke because platforms changed, attention spans dropped, or competition increased. Those are surface-level explanations. Convenient ones. They let marketers keep doing the same things while blaming external forces. The truth is more uncomfortable. Marketing broke because human decision-making evolved faster than marketing tactics did. The Real Collapse Was Psychological, Not Technical The modern consumer is not distracted, lazy, or cheap. They are pattern-aware. They have seen: the funnel the free offer the urgency the testimonials the countdown timer the “last chance” messaging And once the brain recognizes a pattern, persuasion loses its power. This isn’t a theory. It’s behavioral psychology. When the mind anticipates the move, it no longer reacts emotionally. It evaluates. And evaluation kills impulse-driven marketing. That’s what collapsed. Why Persuasion Stopped Working at Scale For decades, marketing leaned on principles popularized by thinkers like Robert Cialdini — reciprocity, social proof, scarcity, authority. Those principles are still valid. But only when trust exists first. What broke was not the principles. What broke was the mass exploitation of them. When: everything is urgent everyone is an authority everything is free everyone has testimonials The brain stops responding. Reciprocity requires perceived effort. Scarcity requires believability. Authority requires credibility. Modern marketing scaled these principles without integrity, stripping them of meaning. The result? Skepticism became the default emotional state. The Data Everyone Feels But Rarely Confronts Across industries — especially local services, fitness, and martial arts — the data tells a consistent story: Facebook and Instagram CPMs have increased 300–800% over the last several years Organic reach has declined, while watch time, saves, and retention matter more than ever Email deliverability has dropped 40–60% for cold or “free” opt-ins Funnel conversion rates continue to decline despite “better creatives” and “smarter targeting” Marketing didn’t become harder. Trust became more selective. Attention didn’t disappear. It learned how to filter. The Russell Brunson Problem (And Why Funnels Aren’t Dead) Funnels didn’t fail. They were put in the wrong order. Russell Brunson taught the world how to systemize conversion. Funnels still work — when used correctly. But funnels were designed for a world where: belief existed before exposure attention was cheaper skepticism was lower That world is gone. The Old Order: Traffic → Funnel → Trust → Conversion The New Order: Belief → Familiarity → Trust → Decision → Conversion Funnels still convert — after belief is established. Without belief, funnels don’t feel helpful. They feel manipulative. Where the Inversion Framework Was Born At Winterborne, we stopped asking: “How do we get more leads?” And started asking: “Why are people resisting before we even speak?” That question changes everything. Because resistance doesn’t come from lack of information. It comes from pattern recognition. The Inversion Framework (Winterborne Doctrine) Inversion marketing begins with a simple rule: Identify what everyone is doing — then reverse it with clarity. Everyone was: pushing offers stacking bonuses increasing urgency lowering commitment optimizing persuasion So we inverted. Inversion Rule #1: Invert the Offer Instead of leading with “Here’s what you get,” we start with “Here’s who this is for — and who it’s not.” This removes anxiety and activates self-selection. Inversion Rule #2: Invert the Message Instead of amplifying pain, we lead with alignment and truth. People don’t want to be reminded they’re broken. They want to feel understood. Inversion Rule #3: Invert the CTA Instead of “Buy Now,” we use decision-based calls to action. “Are we the right fit?” This preserves autonomy — and autonomy is the foundation of trust. Inversion Rule #4: Invert Proof Instead of hype-driven testimonials, we show process proof: how progress is measured why people stay what people notice first This feels real because it is real. Why Decision Pages Convert Better Than Sales Pages Sales pages assume: emotional fragility low awareness urgency as motivation Decision pages assume: intelligence discernment autonomy Sales pages push. Decision pages invite. And invitation is the only thing that works in a high-skepticism environment. This is why Winterborne no longer builds sales pages. We build Decision Architecture. The Psychology Behind the Shift When someone lands on a Decision Page, four things happen neurologically: Autonomy is preserved The brain stays open instead of defensive. Cognitive load drops No pressure, no countdowns, no urgency. Identity matching begins “Is this for someone like me?” Commitment quality increases Fewer leads — better decisions. This leads to: higher show-up rates stronger retention fewer refunds compounding trust Why Winterborne Exists Winterborne wasn’t built to optimize marketing tactics. It was built because the industry refused to accept reality. Marketing did not need: louder messaging smarter ads more automation It needed psychological alignment. Winterborne exists to help brands stop: chasing attention manipulating emotion begging for action And start building systems people choose to enter. The Truth Most Will Ignore This framework isn’t comfortable. Because it: filters people out slows vanity metrics requires conviction Most businesses will keep discounting, stacking offers, and chasing leads — wondering why nothing sticks. The future belongs to brands that are clear, calm, and selective. Final Thought The old marketing playbook didn’t fail because it was wrong. It failed because humans evolved. The brands that win in 2026 won’t persuade better. They’ll align better. If this resonated, follow Nick Dougherty on Instagram. Everything published there is the real-time application of this framework. Winterborne isn’t a tactic. It’s a response. And this is only the beginning.
By Nick Dougherty July 23, 2025
It’s that time of year again—back-to-school season is here, and it’s one of the biggest opportunities of the year to grow your school. But before we talk about flyers, graphics, or ads, let’s get real about one thing: Are you giving value —or just noise? “The whole key to your marketing is you have to provide value for people and expect nothing in return. ” That one line is everything. In this webinar, I walked our community through a complete back-to-school marketing campaign—graphics, emails, social posts, and strategy. Over 20 hours of work went into it, and we’re giving it away completely free. Why? Because that’s what real value looks like. Everyone Talks About Value… But What Are You Really Giving? Too many businesses are showing up online with the wrong energy. No value. No heart. Just random posts—and then wondering why nobody is engaging or buying. Here’s the truth: If your content isn’t connecting… If it’s not starting conversations… If it’s not making someone stop their scroll… Then it’s not working. Stop Waiting. Start Giving. Don’t wait for a perfect funnel or fancy design. Start by asking: What is anyone getting from you today? How are you helping people—right now? What makes you unforgettable in a crowded feed? That’s the foundation of this back-to-school campaign. Not ads. Not gimmicks. Just real help, delivered consistently. Marketing Is Magic… or It’s Invisible Your marketing either stops someone in their tracks—or it gets scrolled past and forgotten. And that’s the line in the sand today. This campaign isn’t about spending more money. It’s about making your message magnetic. Because when you show up with clarity, energy, and a genuine offer to help…  That’s when the magic happens.
By Nick Dougherty April 21, 2025
Let me tell you a truth bomb that might just change your entire business trajectory: “The wake-up slap algorithm is not your enemy. Your silence is.” That one line says it all. In an era where attention is currency, the speaker behind this game-changing insight—a marketing and media strategist who’s partnered with some of the most influential entrepreneurs in the world—reveals exactly what it takes to stand out, grow fast, and stay relevant. This isn’t theory. It’s war-tested strategy. The Game Has Changed. Here's How to Win It. 1. You’re not just a brand. You’re a media company . Let that sink in. Your job isn’t to run ads and hope for a few likes. Your job is to show up every damn day with content that: Builds trust Builds identity Builds community The speaker’s been through the grind. He didn’t “go viral”—he built value . He didn't chase trends—he created a movement by leveraging three weapons: Consistent content creation Strategic partnerships Relentless differentiation “You don’t want to look, sound, or feel like anyone else. That’s the brand.” Be Different, Or Be Forgotten The worst thing you can be in business today is forgettable. “If your heart were set on building a real vibe , you’d be sickened by looking like everyone else.” Too many entrepreneurs copy. They blend. They water down their message. And they wonder why they get ignored. This speaker flipped that script. He built something bold. Raw. Personal. Because that’s what connects. And connection = currency. Collaborate with Killers Want to shortcut success? “Collaborate with killers. I don’t know if anyone’s doing it at the level I am.” This isn’t just about who you know—it’s about who you create with . Strategic partnerships amplify your message, fast-track your reach, and embed your brand in new audiences. He’s done it with names like Tony Robbins, Dean Graziosi, George Bryant, and Randy Garn. Why? Because alignment matters more than algorithms. Content Is the Frontline of Your Brand “You are your own media company and it’s just the scale or the level of where it is right now.” So, what’s the level you’re playing at? This isn’t optional. This is your new job description: Wake up Document Publish Repeat And don’t rely on organic growth alone. That’s amateur hour. You have to invest in attention, in strategy, in systems that scale. Stuck in the Same Place? That’s a Choice. Here’s the slap: “If you're stuck in the same environment, you need to invest your time and energy and fly out and hang out with me for a day. If you're not willing to get out of that environment, you're going to stay in it.” Translation: if you want to grow, get uncomfortable. Get in the room. Get around people who stretch you. Final Takeaways (The "Kicker Quotes" You Need to Tattoo on Your Brain) “It's like we all know that. But they don’t have a solution. I do.” “The wake-up slap algorithm is not your enemy. Your silence is.” “Collaborate with killers. It’s not cocky—it’s the truth.” What to Ask Yourself Next: Are you creating consistent, high-impact content—or just blending in? Who are you collaborating with that elevates your brand? What do people feel when they interact with your business? What environment are you stuck in—and are you brave enough to leave it?
More Posts