Fistful of Dollars: How to Win the Transition Money Game

fist holds dollars against green and black background

Transitioning from active military service to your happy civilian life can feel like you are crossing a wide and perilous river. You can't quite see the other side, but it looks expensive over there. (Believe me, it is.)

Paying the Transition Ferryman

As the transition master coach for's Veteran Employment Project, I see transitioning service members do one of two things to cross over the transition river. You can either 1) build a bridge to the other side with your own savings, or 2) you pay the ferryman to row you across with his debt paddle.

Either way, one symbolic coin will not be enough. You are going to need a fistful of dollars -- and some really great strategies -- to take you to the other side, because transition is expensive.

Sign up for our FREE Fistful of Dollars: Financial Literacy for Transition Master Class.

Not only are there a lot of hidden costs and tricky changes, but it can take a significant amount of work, time (and a little luck) to find a job on the civilian side.

According to a 2019 Pew Research Center study, only one in four military members had a job waiting for them when they left the military. According to the study, another 32% of veterans landed a job within six months. It took 21% of veterans 6-12 months to land a job. For 22%, it took a year or more.

That is a long time to go without income. No wonder so many of you have told me that worries about your finances keep you up at night during transition.

Yet did you know transition finances can be gamed with a little knowledge and foresight? There are so many financial strategies to help you get from the active-duty side of the river to the civilian side with your fistful of dollars still intact.

FREE Transition Master Class for Financial Strategies

That's why I invited USAA certified financial planner J.J. Montanaro to join me for our upcoming FREE transition master class Fistful of Dollars: Financial Literacy for Military Transition on Aug. 4 at 4 p.m. EST.

In just 60 minutes, you will learn:

  • How to build your financial bridge over the transition river if you have time.
  • How to put together a clever financial raft if you have not been able to save.
  • How to avoid the five most dangerous financial whirlpools hidden in military transition.
  • How to stop agonizing over some of the most hotly debated financial decisions and start thinking of financial independence.

Sign up today for Fistful of Dollars: Financial Literacy for Military Transition TODAY. Or discover what's next in your career journey with our FREE transition master classes in our master class video library. Find out the secrets to getting a civilian hiring manager to see your true value. We teach you proven career-level strategies to help you obtain your next, high-impact job. Sign up today.

Jacey Eckhart is the transition master coach for's Veteran Talent Pool. She is a certified professional career coach and founder of who is known for her engaging workshops, insightful articles and her ability to pinpoint solutions for individuals in transition.

Learn More About the Veteran Employment Project

To get more tips on how to make a successful military transition, sign up for one of our FREE Military Transition Master Classes today. You can view previous classes in our video library. Questions for Jacey? Visit our Facebook page.

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