top of page

First Officer Recommendations

Jason's Financial Strategy Statement

"Creating stability within movement is our priority as we navigate Dallas career demands and Boston family ties.”

Jason’s Financial Action Plan - $4,000/Month Allocation Dashboard

1

Leg One (Months 1-8): Building Reserve and Airline Benefits Maximization

  •  HSA + supplemental insurance + legal plan: $450/month

  • Cash Reserves: $3,300/month (until $30K in the AACU)

  • Retirement: $250/month (working toward AA 401k matching minimum)

2

Leg Two (Months 9-48): Building Assets

  • Airline Benefits Maximization: $450/month (continued)

  • Home Down Payment Fund: $2,600/month (after confirming $30K Cash Res)

  • Retirement Acceleration: $950/month 

    • Roth IRA: $500/month

    • Additional AA 401(k): $450/month

Jason's Discovery: Their Financial Strategy Statement on Approach

As a pilot balancing the demands of a Dallas base and Boston roots, my financial strategy seeks to create stability within movement. I aim to build a life where geographic separation doesn't mean emotional distance, career advancement powers personal freedom rather than defining it, and my irregular schedule becomes an asset rather than an obstacle. My wife and I are building financial altitude that allows us to navigate toward our most meaningful destinations—a home that grounds us, a family that fulfills us, and a future where our contributions extend beyond the flight deck. We're charting a course where professional dedication fuels personal possibilities.

My strategy statement captures several key elements of my situation:

  1. The tension between current base and family connections

  2. The unique nature of my career and schedule

  3. The major life transitions ahead (home purchase, family)

  4. The desire to use financial planning as an enabler of life goals

  5. The implicit values of balance, purpose, and planning

My statement positions money as a tool rather than a goal—a means to create the life flexibility my wife and I need given our unique career circumstances. We acknowledge the geographic and scheduling challenges of a pilot’s life while framing them as manageable with proper planning.

Groundcrew (P4P’s Role) = Advisor + Educator + Guide

Our part is fun, and it’s staged around learning Jason’s unique story, considering his current situation, past choices, and future goals. We seek to define, over time, what Jason believes about money and begin to create a set of guiding principles for managing his family’s finances.

As Jason's advisor, we’ll revisit his strategy statement every few years, especially when making major decisions. The question becomes: "Does this financial move align with creating stability within movement? Does it enhance Jason’s ability to navigate toward our meaningful destinations?"

 

This strategic North Star will help Jason evaluate opportunities through a consistent lens, whether it's deciding on where to live, timing of family planning, or career advancement opportunities.

chris-leipelt-4UgUpo3YdKk-unsplash.jpg

The Details of Jason’s Financial Dashboard: Leveraging $4,000 Company Benefits

Jason’s position at his airline offers significant benefits that should be maximized before allocating his $4,000 monthly surplus. Here’s Jason’s employer-specific plan to maximize airline benefits first:

Insurance & Protection

  • Confirm Airline Provided Life Insurance: Company-paid 2x annual salary ($260K) basic life coverage

  • Add Supplemental Life Insurance: 7x additional coverage

  • Long-Term Disability Protection: Enroll with 50-60% income replacement

  • Add Loss of License Insurance

Legal & Estate Planning

  • Enroll in your Group Legal Services Plan ($20-30/month)

  • Getting a Will & Estate Documents with Aviation-Specific Provisions

Healthcare Optimization

  • Enroll High-Deductible Health Plan

  • HSA Maximization $4,150/yearly ($345/month)

  • Capture any Airline HSA Contribution

  • HAS Investment Strategy: Once HSA exceeds $5,000, invest the surplus for tax-free growth

Retirement Foundation

  • Contribute up to the airline's 401(k) Match

  • Add Profit Sharing to Cash Flow

Company Pilot-Specific Advantages

Flight Schedule Integration

  • Schedule larger 401(k) contributions during high-paying trips

  • Align HSA funding with trip pairing patterns

  • Use schedule bidding strategy to optimize income potential during key savings periods

Airline Career Path Planning

  • Structure home savings timeline around potential base transfers

  • Align major purchase decisions with anticipated upgrade timeline

  • Leverage Airline's geographic presence for housing decisions (Dallas offers excellent affordability and no state income tax)

Tax Efficiency Through Airline Benefits

  • Maximize pre-tax benefits to reduce taxable income

  • Utilize airline's commuter benefits program if commuting from Boston

  • Strategically time FSA vs. HSA elections based on anticipated medical needs

By fully leveraging the company's benefit package before allocating Jason’s surplus cash flow, we’re attempting to extend his effective income well beyond his $130K salary. This integrated approach ensures he’s not paying out-of-pocket for protections and services the company already provides or subsidizes.

The benefits dashboard becomes his preflight financial checklist - ensuring everything is properly configured before directing their hard-earned money toward longer-term goals.

Planning for Pilots gold and white logo

Subscribe to our newsletter!

Thank you!

No spam, just value. Your inbox and we respect it.

Advisory services offered through Capital Design Private Wealth, an investment adviser registered with the U.S. Securities and Exchange Commission. Registration as an investment adviser does not imply a
certain level of skill or training.
Planning for Pilots is not a DBA, or business name, of Capital Design Private Wealth.
The information presented on this website is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. This website, other websites belonging to Capital Design Private Wealth and any associated social media links offer news, commentary, and generalized research, not personalized investment advice.

bottom of page