30 Day Financial Transition Challenge Day 7: Job Risk Mindset

Welcome to Day Seven of the 30 Day Financial Transition Challenge.  Today’s article focuses on your Job Risk Mindset.

Bottom Line Up Front (BLUF) 

The ‘job risk mindset’ simply reflects the amount of uncertainty you’re willing to take to live the life you want.  Are you the kind of person who’s always wanted to start a business?  Are you more of a ‘work-to-live’ kind of person?  Either way, you should take some time to think about what you’d really like to do in your post-military life.


Your military transition represents one of the biggest opportunities of your life.  It’s worth taking some time to evaluate what kind of job risk you’re willing to take in support of your post-military career goals.

Do you have a dream job that you’ve always looked to explore?  Perhaps it requires a bit of risk, like starting a business or going into a different line of work that might not pay off immediately.  Perhaps you’ve supported your spouse through their career, and now it’s your turn.

Whatever the case may be, you probably need to decide how much uncertainty (job risk) you’re willing to tolerate in order to explore these options.  Doing so will help you evaluate your ‘left & right limits’ with regards to how much risk you’re willing to take in pursuing your ‘dream job.’


Your goal should be to figure out:

  1. Whether you want to do something non-traditional (like starting a business)
  2. What your risk tolerance is for that non-traditional venture
  3. What kind of trade-offs you’re willing to make (i.e. location vs pay, hours vs quality of life, etc.)

Relevant articles

What you need 

Nothing.  For some people, this will be a quick decision, especially if you’ve already got a job lined up and don’t have any entrepreneurial interests.  If that’s the case, feel free to review the past 6 days’ work to see what questions come to the top of your list.  For others, this will be a brainstorming exercise so you can figure out how far you’re willing to go.


This exercise consists of a simple checklist of questions to help frame your thoughts regarding your post-military employment.

  1. Am I going for a paycheck or something I want to do?  Or both?
  2. If I’m going for a paycheck, what happens if I get laid off?
  • Do I have a plan B?
  • Do I have savings? How much?
  1. If there’s something else I really wanted to do, what are the next steps?
  • Define what it is I really want to do (e.g. start a business, community involvement)
  • Can I start this while on active duty? How much does it cost?
  • Is it something I can start part-time, like a hobby, or volunteer effort?
  • Is it something that I can monetize? Is it something I want to monetize?
  • What do I have to give up in order to do this?
  • Do I have enough money to make it through to my end date?
  • Do I have a contingency plan?
  • Do I have access to liquidity if you run out of money for school or your business?
  • What tripwires will tell me that I need to change course?
  • Time-based (I’ll give this project one year, then get a job)
  • Investment-based (I’m willing to put XX dollars into this, then I’ll drop it).
  • What do I have to give up in order to do this?
  1. Establish a career checklist based on what you’ve done to this point.  Most of this work will have occurred in Day 5 (Invest in Your Career), Day 6 (5-Year Plan) and today.   This should include any business development, resume building, and other critical items that you need to execute to make this plan work.  We’ll revisit this checklist in a couple of weeks to see what adjustments you might need to make.


To wrap up, today you’re going to:

  • Determine how you’re willing to go to pursue your non-traditional ambitions.
  • Figure out how much tolerance you have for career-related risk.
  • Consider trade offs you may have to make, regardless of your choice (i.e. am I willing to give up family time to keep progressing in my career field, or would I rather ‘work to live?’)

Tomorrow, we’ll discuss your credit situation.  Specifically, we’ll discuss your ability to access capital (if needed), your credit scores, and lowering the cost of your long term debt, such as mortgages and student loans.




About Forrest Baumhover

Forrest Baumhover is a Certified Financial Planner™ and tax professional. His firm, Westchase Financial Planning, focuses on the unique financial planning needs of servicemembers and families looking to separate or retire from active duty.

If you’d like to learn more about Forrest or his services, please check out the About Forrest page at the top of this article.

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One Response to 30 Day Financial Transition Challenge Day 7: Job Risk Mindset

  1. Pingback: 30 Day Financial Transition Challenge Day 6: Five Year Plan

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