Courageous Discussions – Judy Skilling

“It is okay to ask for help. It is not shameful, nor embarrassing. It’s very humble, and courageous to do so.” Judy Skilling

Regardless of the level of success attained while serving in the military, transitioning to civilian life is never easy. Finding people who have successfully gone through similar experience can make the process easier and less stressful. Our guest today, Judy Skilling, taps from her experience in the military and post military to help others who are transitioning and says that it all starts with asking for help.

Judy Skilling is a Certified High Performance Coach that works with veterans to help them re-claim and excel in their work, health, and relationships by tapping into their trained military behaviors and learning how to apply it in a civilian lifestyle. As a Navy veteran, Judy understood the struggles of adjusting to the civilian life post military and with using specific high-performance principles and techniques, she is able to successfully navigate the civilian sector without feeling lost or confused on her personal life path. She now focuses on working with veterans to help them accomplish similar results: gaining a clear direction on next steps in their life after service. 

Judy Skilling work has been featured in numerous publications such as Forbes, Entrepreneur, Thrive Global, Medium, and so forth. She has a book published titled, “Un-Hot The Mess You Are”, a co-author of a new release book called “Dare to be Authentic Volume 6: Finding Your Purpose” and a new published journal titled “The Transitioning Veteran Journal: A Self-Guided Journal to Discovering Who You Are Post Military,” which can all be found on Amazon. 

In today’s episode, Judy talks about her life in the military and the events that led her to pursue her current career. She will also highlight her current business and how she helps others have a smooth transition.

Listen in!

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  • I joined the navy in 2000 and a year later 911 happened and at that time, I was actually stationed in Puerto Rico which changed the whole dynamic of being in the military. [3:14}
  • I was deployed during Operation Iraqi Freedom and Enduring Freedom and so from 2002 to about 2005 I was on three different warships in the Middle East. [3:49]
  • I served seven years and got out and became a nurse working with emergency medicine which was a great experience. [4:35]
  • At that point I was about mid 20s already leaps and bounds ahead of my peers, just because of the military experience that I had. [5:17]
  • When you are in the military, it definitely broadens your life experience as you’ll see and do things, people half your age won’t even have the chance or opportunity to. [5:46]
  • I was married and in the year of 2013, unfortunately, my husband at the time who was also a veteran, had gotten diagnosed with cancer. [6:04]
  • I journeyed with my husband through that battle for five years almost. [7:03]
  • During that journey, it got me to think of trying some things to help supplement the income so I can be more at home. [7:09]
  • That’s where coaching actually came into the picture and I went through a coaching program as a client and loved my transition so much that I wanted to be a coach myself. [7:38]
  •  I realized how many veterans could use this type of guidance and their life to help them whether they’re leaving the military or transitioning. [8:51]
  • I became certified and it changed my life and now I try to get more of what I learnt in front of these veterans. [9:05]
  • When I served and I was in the military everything was routine and very predictable but we also had to be flexible to adapt to any unexpected changes. [11:56]
  • That skill set has served me many times after leaving the military, being in the emergency room and being an entrepreneur. [13:14]
  • Commercial break. [14:18]
  • For most of the veterans that I’ve worked with, they still feel like they’re in this funk of transitioning regardless of the period they have been out. [16:16]
  • They get to have a hard time getting acclimated into the civilian lifestyle because there’s something special unique about a bond they have when in service. [16:26
  • They struggle with identity of who they are supposed to be like in this next phase of life and so that’s one of the things that I help them with. [17:16]
  • We work on not only finding their purpose which is about what they are passionate about at that moment. [18:02]
  • When you are able to get clear on that, then that kind of opens up some other doors of opportunity and owning the new sense of independence which can feel a little foreign. [18:21]
  • I help people really embrace this new person of themselves post military and help them feel really good about who they are now. [20:10]
  • When I get to talk to somebody and have a conversation with them, my aim is to see if they’re fit for coaching. [25:13]
  • I also have to determine whether or not they need help outside of coaching, like psychological help, or therapy help because coaching is not therapy. [26:00]
  • I also have to distinguish when they’re ready and invested and need a little bit of more one on one personal guidance on how to handle some big responsibilities. [26:23]
  • One of the things that a lot of veterans struggle with, is confidence and so we talk about courage and not only speaking up for self but also having courageous discussions. [28:14]
  • One of the things that as a veteran I have seen and been involved in different veteran groups is we don’t ask for help and that we can figure it out on our own. [30:18]
  • One of my things I’d love to leave you with is it’s okay to ask for help. It is not shameful, nor embarrassing. It’s very humble, and courageous to do so. [30:33]
  • It’s always good to reach out for help whether it’s working with me or with any kind of coach, or just any kind of friend, it’s always okay to ask for help. [30:51]


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