top of page



All Posts


From E-1 to Millionaire: A Blueprint for Financial Success in the Military
When a young American raises their right hand and takes the oath of enlistment, they commit to a life of service, sacrifice, and discipline. Yet far too often, that same commitment does not extend to their personal finances. Many service members leave money on the table, underutilize their benefits, and miss out on the extraordinary wealth-building potential of compounding. The purpose of this article is to show how even an E-1, the lowest enlisted pay grade, can retire as a.
Kirk Reagan
Oct 164 min read


Traditional vs. Roth for TSP and 401(k): How to make the call
If you’ve ever stared at your enrollment screen wondering whether to check the Traditional box or the Roth box, you’re not alone. I get this question constantly from service members and professionals in their first or second career. The short answer is that the choice comes down to tax timing and a few real-life variables most people overlook. Watch the video: https://youtu.be/l-tpsTHI6hQ Work with us: https://highflightfinancial.biz First, what each option actually does Tra
Kirk Reagan
Oct 162 min read


Should I Leave the Air Force at 32 for the Airlines—or Stay Until Retirement?
One of the most common questions I hear from military aviators is this: At age 32, should I separate from the Air Force and head straight to the airlines, or stay in for a full 20-year career and then make the jump? It’s a decision with financial, personal, and professional dimensions. While lifestyle, mission, and family considerations all play a role, today I want to focus purely on the financial side of the equation. For fiscal year 2025, the aviation bonus stands at $35,0
Kirk Reagan
Oct 163 min read


Turning Deployment Into a Financial Advantage
If you just got word you’re deploying, you’re probably juggling a lot at once. While the news can be heavy, there are several concrete ways to turn this season into a financial win. Here is a clear, actionable guide to the benefits you can use and the moves that can put real money back in your pocket. 1) Combat Zone Tax Exclusion Income earned in a designated combat zone is tax-exempt for most service members. This typically covers: Base pay Incentive pays such as flight pay
Kirk Reagan
Oct 164 min read


Should I stay or Should I go?! Lieutenant Colonel or Stay for Colonel? The Real Value of the Pension
This is an analysis of the decision to stay in the military for Colonel or retire as a Lieutenant Colonel.
Kirk Reagan
Sep 283 min read
bottom of page