How High Achievers Can Successfully Navigate Career Transitions and Workplace Challenges

What if the biggest barrier to career advancement isn't your technical skills, it's how you navigate workplace transitions and speak up in rooms where you're "the only"?

In this episode of Engineer Your Success, Dr. James Bryant talks with Ashley Rudolph, performance coach and former tech VP, about the unique challenges high achievers face during career transitions. From leading through layoffs to overcoming "the only" syndrome, Ashley shares why execution matters more than planning when it comes to real career transformation.

You'll discover why "Ashley excels at excellence" became her defining moment, how to adapt when environments aren't built for you, and what it really takes to turn transitions into opportunities. Whether you're eyeing a promotion or navigating workplace challenges, this episode will help you lead with confidence through uncertainty.

Key Moments in the Episode

00:00 – Leadership Under Pressure: Ashley's critical decision-making moment during team layoffs and the type of leader she chose to become

01:32 – Defining High Performers: The "Ashley excels at excellence" origin story and what drives people to continuously push for better

02:57 – Tech Executive Journey: How Ashley grew from individual contributor to VP in 5 years and the mistakes she learned from

04:09 – Navigating Career Transitions: Leading through uncertainty and preparing your team for their next chapters

09:27 – "Being the Only" Concept: Why it's different from imposter syndrome and how to thrive in rooms not designed for you

10:33 – The Left-Handed Analogy: Adapting to environments built for others without giving up on your goals

11:51 – Three Dimensions of Transformation: Ashley's proven coaching methodology that focuses on real change, not just planning

16:29 – Role Reversal Interview: What high achievers really struggle with—worthiness and self-sabotage patterns

19:41 – Purpose and Calling: Why both coaches continue doing this work and the impact on their clients' lives

Key Insights & Takeaways

• High performers are driven by an internal need to continuously excel
• "Being the only" in a room creates unique challenges beyond typical imposter syndrome
• Most coaching fails at execution—focus on daily actions, not just strategies
• True leadership is revealed in how you handle crisis situations
• Even technical professionals with strong expertise struggle with feelings of worthiness

🧠 Notable Quotes

"I'm willing to do the hard things and I'm willing to have the hard conversations—I'm just not someone that runs away from the scary things." — Ashley Rudolph

"People pay me for the change. They don't pay me for presentation, they don't pay me for a plan." — Ashley Rudolph

👤 Guest Information

Ashley Rudolph – Performance Coach & Former Tech Executive
Founder of Work with Ashley R | Specializes in high achiever career transitions
🌐 workwithashleyr.com
📧 newsletter.workwithashleyr.com
💼 LinkedIn: Ashley Rudolph (with a pH - like Rudolph the Red Nose Reindeer)

About Engineer Your Success

Engineer Your Success equips technical professionals and business owners to become confident, purpose-driven leaders who thrive at work and at home.

Through executive coaching, business consulting, and strategic content solutions, we help you:

• Lead with clarity and communicate with impact
• Build aligned systems that support your values
• Avoid burnout while achieving professional success
• Transform from technical expert to influential leader

🔗 Connect With Us

Learn more at engineeryoursuccessnow.com
Follow Dr. James Bryant | https://sleek.bio/jbryant