Military Retirement Transitions

From Uniform to Civilian Life

The Mission’s Changed—Your Plan Should Too

Retiring from the military isn’t the end of your career—it’s the start of a new chapter. But while your mission may change, the complexity of your benefits, pensions, and financial decisions doesn’t go away. In fact, it often gets more complicated.


At Freedom Financial Planning Solutions, we help service members and veterans in Virginia, Michigan, and throughout the nation navigate the transition from military to civilian life with clarity, purpose, and a long-term plan. As a military retiree himself, Steve Underriter understands both the structure of military life—and the uncertainty that can follow.

Start with a Free Planning Call

What We Help You Figure Out:

  • How do I plan for retirement after the military?

    We help you organize your pension, TSP, and benefits—and build a long-term plan that supports your next phase, whether that’s work, rest, or something in between.

  • What should I do with my TSP when I leave the service?

    We walk you through your options—keeping it, rolling it over, or converting to Roth—based on your goals, tax situation, and future plans.

  • How does my pension fit into my full retirement plan?

    Your pension is a solid foundation, but not the whole picture. We show you how it works with Social Security, savings, and second-career income.

  • What if I’m starting a second career?

    We help you balance new income with long-term planning—so you can keep building without missing opportunities to reduce taxes or strengthen retirement savings.

  • Can I use VA or TRICARE benefits to reduce out-of-pocket costs?

    Yes—and we’ll help you factor them into your budget, healthcare planning, and broader financial strategy.

What Goes Into a Military Retirement Plan

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Military Pension Planning

We help you incorporate your pension into a sustainable, long-term income plan, including tax strategies.

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TSP Rollover Help

We walk through your options clearly so you can decide with confidence—not guesswork.

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Second-Career Strategy

We balance current earnings with future retirement planning so you can build for what’s next.

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Veteran-Focused Advice

Steve’s firsthand experience gives you access to a planner who’s been through it—and knows what matters.

our ongoing process

Helping Veterans Navigate Financial Life After Service

01

Review Your Benefits & Career Goals

We start with open-ended questions and real conversations about what you both want from retirement.

02

Map Out Your Next Phase

We build a step-by-step ongoing plan that ties together military benefits, new income, and long-term retirement goals.

03

Adjust for Civilian Life

We guide you through the financial decisions that come with a second career, new tax considerations, and lifestyle shifts.

04

Meet Regularly to Adapt the Plan

We revisit and revise the plan together—because retirement is a journey, not a deadline.

Financial Planning From Someone Who’s Been There

Steve brings 21 years of military service—and years of planning experience—to every conversation. You don’t need to explain the structure, the acronyms, or what PCS means. You just need someone who gets it, and who can help you move forward with a real plan.