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#3: From the front lines of Baghdad to Tech, Venture Capital, and VP at

advice anxiety interview mindset pivot storytelling Apr 25, 2021

Inside the Episode

In this episode, I introduce speaker Dan Savage, and we chat about his journey from joining the army to transitioning into tech at LinkedIn and the prestigious VC firm, Sequoia. Now he is a VP at, where he helps fellow veterans pivot into their new civilian careers.   

Dan gets real with us and talks about the anxiety of not knowing what is next. He walks us through how he figured out the next move at the multiple crossroads he found himself in. 

“Years ago, when I thought that I was broken because I didn't know what was next, I realized I was just a civilian. The inherent nature of civilian life is that there are no very clear answers” - Dan. 

Not going it alone - even as an introvert. 

On his journey, Dan relied heavily on others, from mentors to people who have walked the path before him. As a guy who grew up in a self-described blue-collar atmosphere, he never saw himself as someone who would ever end up at Havard, but thanks to one of his early mentor’s encouragement, he is now a Havard alum. 

“I think every step along the way. There's been a mentor or a coach or a teacher or somebody who's said, hey, there's a whole other thing on the other side of this hill that you can go pursue.” - Dan. 





  • 00:00 - Introducing Dan Savage
  • 03:35 - Dan’s background and current role at Shift
  • 04:51 - The identity challenge that comes from pivoting from the military back to a civilian life
  • 06:28 - Being purpose-driven and wanting to do good
  • 07:00 - Becoming Chief of Staff at Syracuse University
  • 08:28 - A new growth opportunity: Leading the military program at LinkedIn
  • 10:43 - The toughest part of transitioning: The ambiguous freedom of civilian life vs. the clear path in the military
  • 14:16 - The importance of having mentors, teachers and being curious
  • 20:16 - Learning a new skill as a civilian: Storytelling
  • 24:14 - Transferring a skill from the military: Assessing ambiguity and the bias for action
  • 30:19 - What makes a good leader - extreme ownership
  • 34:09 - Advice for people who want to pivot
  • 40:36 - Don’t keep your goals to yourself
  • 44:47 - Be a part of a community of people you admire
  • 50:15 - The Career Accelerator


Stuff from the episode

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