The Blog From Employee to Creative Entrepreneur with Clarissa Castillo-Ramsey (HHR EP44)

From Employee to Creative Entrepreneur with Clarissa Castillo-Ramsey (HHR EP44)


"You don't need to quit tomorrow. You don't need to quit in six months, but you do need to start before you're ready." -Clarissa Castillo-Ramsey



This episode delves into an inspiring journey of transformation—from employee to creative entrepreneur—with Dr. Clarissa Castillo-Ramsey, an abstract artist, leadership and life coach, author, podcaster, and organizational psychologist. Her passion for helping creatives design their lives on their terms sheds light on fostering empowerment, especially among women.

A life marked by two enduring themes shaped Dr. Clarissa's journey: creativity and a passion for helping others. Though her aspirations to be an artist weren't initially supported, her drive to honor her parents' sacrifices and make them proud ultimately influenced her chosen path. This tug-of-war between her creative passions and familial expectations ignited a quest filled with various job experiences, culminating in her dream role as an internal coach for a healthcare organization.

The onset of the COVID-19 pandemic brought about a paradigm shift for many, including Dr. Clarissa. It forced a slowdown, prompting reflection on life's true priorities. Vision board workshops she conducted revealed common themes: family and rekindling creative passions. The pandemic ushered in an era of reevaluating what truly matters and provided an opportunity for many to slow down and reassess their lives.

More than ever, there's a noticeable shift towards entrepreneurship. But transitioning from a 9-to-5 job to entrepreneurship can be daunting and full of uncertainty. Dr. Clarissa's advice is to prepare for this transition and start before feeling entirely ready. Key preparatory steps include taking inventory of one’s skills and interests, identifying the problems they can solve, and understanding the financial implications of their desired lifestyle. Crafting a corporate exit strategy is crucial in making a smooth transition without unnecessary risk.

If one isn't entirely ready to leave their current employment, Dr. Clarissa suggests exploring options like part-time roles or having a candid conversation with one's boss about future plans. Employers may be more supportive than anticipated, especially in today’s gig economy, where quality team members are invaluable.

For those struggling with self-doubt, Dr. Clarissa recommends reflecting on past achievements as evidence of their capabilities. Creating a "Hype file" of positive feedback, accolades, and personal successes can serve as a constant reminder of one’s worth and potential.

Central to Dr. Clarissa’s coaching methodology is her "Painting Your Path" framework, designed primarily for creatives looking to escape the corporate world. This five-step framework includes:

1. Dreaming: Visualizing life beyond corporate confines, using all senses to paint this desired future.

2. Deciding: Committing to the dream and believing in its worth.

3. Planning: Crafting a step-by-step strategy, including a corporate exit plan.

4. Taking Action: Bravely executing the plan, even if it involves uncomfortable steps.

5. Reflecting: Analyzing outcomes, learning from experiences, and refining approaches.

The foundational elements of this framework are cultivating a growth mindset—a belief in the limitless potential of one’s abilities—and maintaining robust self-care practices. Entrepreneurship has its challenges, and self-care ensures sustainability and resilience.

For those ready to embark on this transformative journey, Dr. Clarissa invites you to connect through her Facebook community, Create Your Abundant Life, or listen to her podcast, Painting Your Path. Here, she offers one-on-one and group coaching to guide aspiring creative entrepreneurs toward fulfilling lives designed on their terms.

Reflecting on Dr. Clarissa's insights, the takeaway is clear: give yourself permission to dream, believe in your worth, and approach the journey with a blend of structured planning and self-compassion. This episode encourages everyone to embrace the possibility of change, transforming dreams into reality with thoughtful preparation and unwavering belief in oneself.


Dr. Clarissa Castillo-Ramsey is an abstract artist, leadership + life coach, author, podcaster, and organizational psychologist with a passion for helping creatives start designing life on their terms. She empowers individuals to ‘paint their path’ using her 5-step framework. Clarissa describes her coaching and teaching style as the intersection of leadership development, creativity, and wellness. Her online summits, From Employee to Creative Entrepreneur and The Creative Abundant Leadership Summit have helped thousands of aspiring creative entrepreneurs. Her superpowers: being a relentless cheerleader for possibility, giving tough love, and holding space for people to show up as they are.


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#The Suzanne Show

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Suzanne Proksa, SHRM-SCP, SPHR, HHP

Hey there! I'm Suzanne, a SHRM-SCP and SPHR certified Human Resources and Business Strategist, IAWP Certified Wellness Coach, AADP certified Holistic Health Practitioner, and autoimmune educator with a passion for helping women navigate all things life and business. 

I've been in HR since 1999 and have run businesses since 2004 (unless you also count my adventures selling "all the things" as a kid - then we need to go WAY back. 

I thrive on supporting, coaching, and creating programs for women and people-focused organizations and online businesses so they can positively impact the lives of others.

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