Does anyone ever say “Thank You for your service”  to you when they know you serve or previously served in the military? Ever hear a response like, “Thank You! You are worth it!” Well, you will hear it in this Life After the Military episode!

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This episode of Life After the Military, features Army Colonel (Retired) Jay Santiago – who represents three (3) generations of Army Officers (Jay, his father, and his two sons).

Jay provides his insights into the transition process, shares his lessons learned, and describes how he treated it as a “mission.” 

Unlike most transitioning senior officers and noncommissioned officers, Jay is still with the same company, Worldwide Technologies, that he joined over 11 years ago. Learn about the transition preparation and criteria Jay applied to make such a great choice!


Show notes

00:00 Lees introduces Jay Santiago, Jr.; Jay starts off the interview with very detailed advice for a smooth transition

08:37 Jay lists the things he did well during his transition, noting that the most important thing was to take the time to think, to understand the need, and to develop the right connections

13:20 Howie and Jay implore you to consider how important the transition will be for your family

18:00 Howie and Jay get specific; Howie drops a big tip about health insurance premiums for transitioning vets

20:48 Jay discusses how he carefully chose the company he transitioned into, World Wide Technology, and how he has been progressing with the company for the last 10 years

36:04 The extreme importance of community within and throughout any industry

40:55 Lee asks, “What advice do you have for the specific trajectory of government contracting?

44:26 Howie shares what went wrong during his experiences in contracting noting how a good mentor saved his career

51:35 The discussion shifts back into the need for developing relationships, asking for help, and becoming a lifelong learner

1:03:54 Personal mission and identity aren’t defined by military titles

1:08:43 Howie’s favorite part of the show

1:14:06 Jay details how following his faith and staying purposeful in a community adds significance to his life and aids with mental fitness  

1:21:09 Howie closes the show – “you reap what you sow”