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Jackson Rodriguez

Career Transition Coach & Skills Development Strategist

Jackson Rodriguez

About

Former tech exec turned career coach, I help professionals navigate career pivots with confidence. Specializing in translating existing skills into new industries.

Let’s cut straight to it: career transitions are messy, terrifying, and absolutely worth it. After spending 12 years climbing to VP of Product at a Fortune 100 tech company, I threw it all away to pursue what really lights me up—helping others reinvent their professional lives.

Best decision ever. Scariest too.

In the four years since my leap, I’ve guided over 350 professionals through successful career pivots—from burned-out lawyers becoming UX designers to financial analysts transforming into sustainability consultants. I’ve bottled what I’ve learned into a practical, no-nonsense approach to career reinvention.

Here’s what makes my coaching different: I don’t do fluffy “follow your passion” advice. My methodology is grounded in skills-mapping and strategic storytelling. Together, we identify your transferable talents and craft compelling narratives that help employers see your potential value, not just your past positions.

My regular “Pivot Points” podcast features real stories of successful career changers, breaking down exactly how they navigated their transitions. When I’m not coaching or podcasting, you’ll find me experimenting with my sourdough starter or hiking with my rescue dog, Pixel.

Remember: Your career isn’t a straight line—it’s a series of adventures. The best ones usually start with a bold pivot!

Where I get my news
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To help my clients navigate career transitions successfully, I stay informed through these key resources:

Articles by Jackson Rodriguez

Low Code, No Code = Low Cut, No Cut: How to Future-Proof Your Career Without Breaking a Sweat

Discover how embracing low-code and no-code tools can be your career insurance policy. Learn why building without coding is the smartest way to stay relevant in an AI-driven world—no computer science degree required!

The Flexibility Paradox: Why Your Dream Work Schedule Might Be Your Worst Nightmare

Remote work and flexible schedules promise freedom but often deliver unexpected burnout patterns. This analysis reveals why unlimited flexibility can become a trap and provides strategic frameworks for mastering flexible work without losing professional boundaries or personal sanity.

The Race for Empathetic AI: Can Machines Ever Truly Understand Human Emotions?

Explore the fascinating race for empathetic AI and its implications for human connections. Examine whether machines can truly understand emotions or just simulate empathy, and discover what this means for workplace relationships and human-AI collaboration.

Riding the Wave: How to Turn 2025's Layoff Tsunami Into Your Career Renaissance

Transform 2025’s massive layoffs from career disaster into opportunity. Get the strategic playbook for navigating corporate restructuring, identifying pivot opportunities, and positioning yourself for success during workforce transformation.

Career Storytelling: Crafting Narratives for Professional Growth

Crafting compelling professional narratives that accelerate career advancement and opportunities.

Career Agility: Building Skills for a Dynamic Job Market

Essential career development strategies for thriving in today’s dynamic professional environment.

Reinventing Professional Networks: Hybrid Events and Digital Communities

Best practices for leading and managing distributed teams in hybrid work environments.

Navigating Career Plateaus: Strategies for Renewed Growth

Proven strategies for overcoming career stagnation and reigniting professional growth.

Mid-Career Pivots: Leveraging Experience While Embracing New Directions

Strategic guidance for navigating major career transitions and professional reinvention.

Career Resilience in the Age of AI: Skills That Remain Distinctly Human

Innovative AI applications transforming patient care and healthcare delivery systems.

Portfolio Careers: Building Professional Security Through Diversification

Essential career development strategies for thriving in today’s dynamic professional environment.

Midlife Career Transitions: Strategies for Reinvention After 40

Strategic guidance for navigating major career transitions and professional reinvention.

The Great Career Reset: Strategic Pivots for 2025

Strategic guidance for navigating major career transitions and professional reinvention.

Networking in the Age of AI: Human Connection Still Matters

In the AI age, authentic human networking becomes more valuable than ever, requiring a focus on deep relationships, genuine connections, and value-first approaches that stand out from automated outreach.

The Psychology of Career Transitions: Understanding Your Internal Narrative

Successful career transitions require reshaping internal narratives by identifying limiting beliefs, reframing impostor syndrome, using growth mindset language, crafting bridge stories, and building emotional resilience for the journey.

The Art of the Career Pivot: A Coach's Perspective

Successful career pivots require strategic preparation through skills translation, informational networking, and embracing a learner’s mindset that views each step as progress toward your new professional destination.

Navigating Remote Onboarding: Lessons from 2024

Transform remote onboarding from a logistics challenge into a competitive advantage through pre-boarding preparation, virtual buddy systems, clear communication protocols, and culture-building activities that create belonging from day one.

Building Resilience During a Career Setback

Build career resilience during setbacks by reframing challenges as learning opportunities, maintaining strong support networks, and setting small achievable goals that create momentum toward recovery and growth.

Strategic Networking for Career Changers

Career changers should use “Network Triangulation” by strategically connecting with industry insiders, recent transitioners, and hiring managers to gain comprehensive insights and build mutual value exchanges rather than extracting opportunities.

Navigating Mid-Career Transitions in Tech

Navigate mid-career tech transitions successfully by conducting thorough skills inventories, developing strategic narratives that position change as evolution, and leveraging professional networks systematically to prioritize momentum over perfection.

Career Pivots: When, Why and How to Make Your Move

Make successful career pivots by recognizing key signals like persistent daydreams and motivation loss, then strategically transitioning through skills translation, networking, and viewing setbacks as steppingstones rather than obstacles.

Career Transitions: Navigating Change with Confidence

Navigate career transitions successfully through self-reflection to identify transferable skills, strategic networking in your target field, and building relevant experience through volunteering and side projects before making the full transition.

Leveraging LinkedIn Groups for Real Business Connections (Not Just Self-Promotion)

Strategic LinkedIn Groups networking focuses on valuable contribution, authentic engagement, and relationship building within professional communities to establish expertise, generate leads, and expand business influence organically.

Changing Careers Without Starting From Scratch

Successfully transition careers by leveraging transferable skills, building new competencies, and strategically positioning yourself for industry changes.

Your Resume Isn't a Biography: Keep It Punchy!

Create a compelling resume that captures attention, showcases achievements, and positions you as the ideal candidate for your target roles.

Changing Careers: The Unvarnished Truth About Starting Over

Successfully change careers by using the bridge job approach, conducting skills transfer inventory, building hybrid experience, networking with career transition veterans, and taking strategic side-door entry positions.