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April 8, 2024 29 mins

If you want to take more control of your career there’s no way around it: You are going to have some awkward conversations with your boss.

But what if having a few of these well-planned, uncomfortable conversations could get you everything you want out of your work (along with your boss’s stamp of approval)?

Well, it turns out, they can! Our guest today, Jason Bollman, is proof of that. He shared his initial career change story on the podcast a few years ago. If you haven’t listened to that, it’ll be helpful to fill in more of his story: listen here!

Jason attributes much of his success since his initial career change to continuing to have difficult conversations with leadership. He has created a new role in his organization, gotten himself onto numerous projects that interest him, and has continued to pivot his career to fit him better and better!

What you’ll learn

  • How to prepare effectively for uncomfortable conversations with leadership
  • How to build trust with your organization and foster an environment where you can grow
  • How to know if your company is taking advantage of you

Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit to order it now! Visit for more information or buy the print or ebook here!

Want to chat with someone on the team about your situation? Schedule a conversation


Free Resources

What career fits you? Join our free 8 Day Mini Course to figure it out!

Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.


Related Episodes

  1. Should I Quit My Job? How to Know It’s Time (Spotify / Apple Podcasts)
  2. Discover Your Strengths to Find Your Ideal Career (Spotify / Apple Podcasts)

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