top of page



All Posts


Most Employees Miss This 30% Tax Break: How a Flexible Spending Account Can Save You Nearly $900 in 2025
Healthcare costs are up. Inflation is up. Yet many employees leave money on the table because they skip a Flexible Spending Account. Many don’t understand what it is or are intimidated about how to use it. If you use an FSA the right way, you will lower taxable income and keep more cash in your pocket. What an FSA is A Flexible Spending Account lets you set aside pre-tax dollars for qualified expenses. There are two common types: Health FSA for medical, dental, and vision
Kirk Reagan
7 days ago4 min read


The 10-Year Rule: How Inherited IRAs Changed Forever After the SECURE Act
If you’ve recently inherited an IRA, the rules have changed—and the new landscape can create major tax surprises for families who aren’t prepared. Before 1 January 2020, heirs could “stretch” an inherited IRA over their lifetime. A child or grandchild could keep that account growing tax-free for decades, passing it down again and again. The SECURE Act ended that strategy. Now, most non-spouse heirs must empty inherited retirement accounts within ten years. That might sound ma
Kirk Reagan
7 days ago2 min read


How a $10k Car Can Fund Your Retirement
Your First Car Is Not Just a Car. It Is a Seven-Figure Decision. Most people remember their first car as freedom on four wheels. Few realize it may be the largest financial decision they make in their twenties. The choice between a pricey new ride and a reliable used one can swing retirement outcomes by millions! This is not hype. It is simple math of depreciation versus compounding interest working over time. Cars are depreciating assets in most cases. From the first day you
Kirk Reagan
7 days ago3 min read


How to Retire Early Without a Big Salary (It Starts with One Simple Step)
When you’re young, it’s easy to believe you’ll have plenty of time to build wealth later. But “later” has a way of arriving faster than you think. One of the most powerful financial habits you can need to adopt early is to pay yourself first . That means making your savings and investments your first expense—not what’s left after bills and lifestyle. This one difference is often the difference between retiring comfortably or not. In the U.S., the statistics are sobering. The
Kirk Reagan
7 days ago2 min read


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