Episode 34-The Path to Purpose Driven Work with Jamie Wheaton

Jamie Wheaton’s Journey: From HR to Kickboxing to Coaching 

Jamie’s path to career transformation wasn’t a straight line. His story is a testament to the fact that career reinvention is possible at any stage of life.

🔹 Early Career in HR – Jamie started his professional journey in human resources, helping companies implement programs that supported employees. While he enjoyed aspects of his work, he realized over time that he wanted to make a more direct impact on individuals.

🔹 Owning Kickboxing Studios – Looking for a change, Jamie made a bold move and opened kickboxing studios. He found immense satisfaction in helping clients push past their limits, both physically and mentally. However, after years of running the business, he decided to shift gears once again.

🔹 Becoming a Full-Time Coach – Reflecting on his experiences, Jamie recognized that coaching was where his true passion lay. Now, he helps professionals navigate their own career transitions with confidence and clarity.

His journey underscores a vital lesson: change is always possible, and the skills you’ve built in one career can serve you in the next.

Common Career Transition Struggles and How to Overcome Them 

Changing careers isn’t easy. Jamie highlights some of the most common roadblocks and how to overcome them.

1. Self-Doubt and Fear of Judgment 

One of the biggest challenges people face when making a career shift is self-doubt. Jamie shares how fear of judgment held him back when he first announced he was opening a kickboxing studio.

🔹 How to Overcome It: 

 • Recognize that self-doubt is natural but shouldn’t define your actions.

 • Surround yourself with supportive people who encourage your growth.

 • Focus on doing rather than overthinking—action builds confidence.

2. Fear of Financial Instability 

A major concern for career changers is financial uncertainty. Leaving a stable job can feel risky, especially if you have a family to support.

🔹 How to Overcome It: 

 • Plan ahead: Start saving before making the leap.

 • Consider side hustles to test the waters.

 • Seek mentorship from those who’ve successfully transitioned.

3. Resistance from Friends and Family 

Jamie emphasizes that when you start making career changes, not everyone will be on board. Your spouse, friends, or parents may express doubt or concern.

🔹 How to Overcome It: 

 • Communicate your vision clearly to loved ones.

 • Show them your plan rather than just talking about it.

 • Understand that resistance is often their fear, not yours.

The Power of Clarity: Understanding Your Values 

A major theme of Jamie’s coaching is gaining clarity on your values before making a career shift.

Why Values Matter 

Many people chase money or status without understanding what truly drives them. Jamie stresses that values—not just external goals—should shape your career decisions.

Exercise to Identify Your Core Values 

To help clients gain clarity, Jamie uses an exercise where he asks:

👉 “If money weren’t a concern, what kind of work would truly fulfill you?” 

Most people answer with something meaningful—helping others, creating, or leading a team. By identifying these underlying motivations, you can align your career with what truly matters to you.

Building Confidence Through Action 

A key insight from the episode is that confidence comes from action, not waiting to feel ready. 

The “Just Start” Principle 

Jamie shares a story about a client who was afraid to post videos online for her new business. She feared judgment and hesitated to take action. Jamie asked her:

“Do you worry about what people think when you walk into a store?” 

She realized that people don’t pay nearly as much attention as we think. After this mindset shift, she posted three videos the next day—and got 1,600 views!

🔹 Lesson: Stop waiting to feel “ready.” Taking action, even in small ways, builds confidence over time.

How to Stick with New Habits 

Career change isn’t just about big leaps—it’s about small, consistent actions. Jamie and Matt discuss the importance of forming sustainable habits.

1. Start Small 

Rather than setting overwhelming goals, start with one small, manageable step.

 • Want to get in shape? Start by eating one healthy meal a day.

 • Want to network more? Reach out to one person a week.

2. Make It a Routine 

High performers succeed because they build habits that become second nature.

 • Use a planner or journal to track progress.

 • Schedule time for important career-building activities.

3. Embrace Failure as Part of Growth 

Many people quit too soon because they expect instant success. Jamie emphasizes that failure is part of the journey. The most successful people have failed more times than most have even tried!

Jamie’s 3-Session Career Coaching Program 

If you’re considering a career change but feel overwhelmed, Jamie offers a three-session coaching program designed to provide clarity and direction.

🔹 Session 1: Identify your values and motivations.

🔹 Session 2: Define your ideal career path.

🔹 Session 3: Create a roadmap for success.

This short program helps clients gain clarity, overcome limiting beliefs, and take the first steps toward a career they love.

Want to Work with Jamie? 

🌐 Visit his website: jswinsights.com

📧 Book a free strategy session: Schedule Here