The Military Money Manual Podcast Military to Civilian Transitions with Jesse Cramer, Personal Finance for Long-Term Investors #200
Spencer Reese, founder of the Military Money Manual, joins Jesse Kramer to discuss the unique financial landscape of military service and the critical transition to post-service life. Spencer separated from the US Air Force in 2022 after 12 years as a pilot and now helps military families reach financial independence through his book, podcast, course, and website.
Host: Jesse Kramer - Financial adviser and host of "Personal Finance for Long-Term Investors"
Guest: Spencer Reese - Former Air Force pilot (12 years active duty), founder of Military Money Manual, author, podcaster
Key Topics CoveredMilitary-Specific Financial Challenges:
- Lower enlisted income but essential expenses covered (housing, food, healthcare)
- The "lieutenant mobile" trap - buying too much car relative to rank/income
- Transparent pay structure creates unique comparison pressures
- Status games vs. wealth building: Why the cheapest car often belongs to the colonel
- Split around captain rank - some choose optimization, others choose lifestyle inflation
Creating Financial Systems:
- Spencer's personal story: Living paycheck to paycheck early in marriage with $20 every two weeks for discretionary spending
- How his wife forced financial discipline and communication
- The 30-day test: Could your finances run on autopilot for a month?
- Critical for deployments when internet access may be limited
- Automate everything: bills, investments, transfers
Deployment as Financial Opportunity:
- Tax-free pay in combat zones
- Zero housing/food expenses while deployed
- Spouse can potentially reduce expenses (move home, downsize)
- Real example: Service member paid off all auto and student loans in 3 months of deployment
- Life-changing potential of a single 9-12 month deployment if leveraged strategically
Common Behavioral Traps:
- Most military families are "avoiders" - have the will but lack the skills
- Money wasn't discussed at home growing up, never learned the basics
- Two avoiders marry each other and perpetuate the cycle
- The mistake: Thinking low income is the problem when it's actually overspending on cars
Free Military Resources Available:
- Military OneSource - Free financial counseling specific to your situation
- Airman and Family Readiness Center (each branch has equivalent)
- Face-to-face budget help and financial planning on every base
- No excuse not to use these resources
- Success stories: Enlisted millionaires before 20 years, airmen with $100K after 4-year enlistment
Military vs. Civilian Pay Reality:
- Officers hit six figures around captain rank
- Buying too much car is easily a 5-6 figure mistake over time
- When you're making five figures, you can't afford five-figure mistakes
- One good decision (avoiding expensive car) creates massive wealth-building opportunity
The Post-Service Transition Crisis:
- Spencer's story: Left active duty before 20-year retirement, thought side business would be enough
- Financially prepared (large nest egg, near financial independence)
- Completely unprepared for loss of purpose and meaning
- Got depressed for months after separation
- Taking airline job helped initially, but quit after 6 months - still wasn't fulfilling
- The money isn't the hard part - finding purpose is
Purpose and Meaning in Retirement:
- Pre-retirees rank finances as top priority
- 2-10 years into retirement, lifestyle issues become the top concern
- The workplace provided: paycheck (replaceable), purpose (harder to replace), socialization (often overlooked)
- "What's your job when every dollar has a job?"
- Reference to "The Second Mountain" by David Brooks - four callings: vocation, religion/philosophy, community, marriage
Practical Transition Advice:
- TAP (Transition Assistance Program) - Available starting one year before separation
- Spencer's mistake: Only went once, should have gone twice (at one year out AND closer to separation)
- Too much information to absorb in one session
- Free LinkedIn Premium for a year (included)
- Go early to start the mental transition process
- Guard/Reserve option as a "slow transition" - maintain community while easing into civilian life
The "Not Work" Trap:
- Like high school freshman saying "I'll just do not school this summer"
- Many retirees approach retirement as "I'll just do not work"
- Leads to undefined path and potential struggle
- Better to ease into it with preparation and exploration beforehand
- Parallel to being 17-18 and figuring out life path - retirement is another major transition
Key Mindset Shifts:
- The optimizer who runs 10,000 Monte Carlo simulations will be financially fine
- "As long as the US and capitalism exist, you'll be fine"
- Now what? That's the harder question
- It might take 2-3 years to figure out, and that's okay
- Some retirees find they're busier than ever (Mr. Money Mustache model)
- Others stare at the ceiling at 3 AM wondering what they're doing
- Both are normal - give yourself grace and time
Books Mentioned:
- "The Five Types of Wealth" by Sahil Bloom - Framework beyond just financial net worth
- "The Second Mountain" by David Brooks - Four callings: vocation, religion, community, marriage
Programs & Resources:
- Military OneSource - militaryonesource.com
- TAP (Transition Assistance Program) - Start attending one year before separation
- Airman and Family Readiness Center (or branch equivalent)
- Guard/Reserve transition option
Spencer's Work:
- Website: MilitaryMoneyManual.com (hub for all content)
- Podcast: Military Money Manual (Spotify, Apple Podcasts - nearly 200 episodes)
- Book: "The Military Money Manual" (Amazon and shop.militarymoneymanual.com)
- Co-hosted with Jamie (still active duty officer)
Jesse's Work:
- Blog: BestInterest.blog (hub, weekly newsletter signup)
- Podcast: Personal Finance for Long-Term Investors
- Episode 106: "Retirees, Mistakes, and Wakeup Calls: Expectations vs Reality"
- Shout out to Fritz Gilbert of The Retirement Manifesto
"Just wait till next paycheck." - Spencer's mantra when living paycheck to paycheck early in marriage
"Every dollar has a job, but what's your job?" - Jesse on finding purpose beyond financial optimization
"The numbers are going to work. You've run 10,000 Monte Carlo simulations. You're going to be fine. Now what are you going to do?"
"I don't have time to work. My life is so full." - Common sentiment from successful retirees/FIRE achievers
"You're going to be fine, but it's going to take some time. And that's okay."
Who This Episode Is For- Military service members at any stage (especially those 5-10 years from separation/retirement)
- Veterans who've already transitioned (validation that post-service struggles are normal)
- Civilians planning traditional retirement (lessons apply universally)
- Financial optimizers who need reminder that life is more than spreadsheets
- Anyone supporting military family members
- People struggling with purpose and meaning in life transitions
This episode provides a rare honest look at the emotional and psychological challenges of leaving military service, even when financially prepared. While focused on military transitions, the lessons about purpose, meaning, and life beyond work apply to anyone facing retirement or major life changes.
Originally aired as Episode 117 of Personal Finance for Long-Term Investors. Listen to the full episode on Jesse's podcast feed.
Spencer and Jamie offer one-on-one Military Money Mentor sessions. Get your personal military money and personal finance questions answered in a confidential coaching call. militarymoneymanual.com/mentor
Over 20,000 military servicemembers and military spouses have graduated from the 100% free course available at militarymoneymanual.com/umc3
In the Ultimate Military Credit Cards Course, you can learn how to apply for the most premium credit cards and get special military protections, including waived annual fees, on elite cards like the American Express Platinum Card® and the Chase Sapphire Reserve® Card.
Learn how active duty military, military spouses, and Guard and Reserves on 30+ day active orders can get your annual fees waived on premium credit cards in the Ultimate Military Credit Cards Course at militarymoneymanual.com/umc3
If you want to maximize your military paycheck, check out Spencer's 5 star rated book The Military Money Manual: A Practical Guide to Financial Freedom on Amazon or at shop.militarymoneymanual.com.
Want to be confident with your TSP investing? Check out the Confident TSP Investing course at militarymoneymanual.com/tsp to learn all about the Thrift Savings Plan and strategies for growing your wealth while in the military. Use promo code "podcast24" for $50 off. Plus, for every course sold, we'll donate one course to an E-4 or below- for FREE!
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