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THE REAL VALUE OF PLANNING: REFLECTING ON A LIFETIME OF PURPOSEFUL FLIGHTS

  • hilton721
  • Jul 28
  • 4 min read

My wife and I have been savoring this New England summer, though like many of you, we can hardly believe we're already halfway to August. Up here, summer feels like a treasured break between demanding seasons – one we wish could last indefinitely, yet somehow always seems to pass by faster each year.


This weekend, as my wife and daughter sorted through hundreds of photos pulled from storage, I found myself drawn into their orbit of memories. Picture after picture told stories of birthdays celebrated, vacations taken, quiet moments captured, and milestones marked. Watching them laugh at forgotten moments and reminisce about people and places from years past, I was struck by a truth that's become increasingly clear in my 25 years of financial planning: Time is the most precious asset we'll ever manage.


THE PLANNING WE OFTEN OVERLOOK IN THE COCKPIT OF LIFE

As senior airline pilots, you understand the critical importance of preparation. You've meticulously checked weather conditions, calculated fuel requirements, reviewed alternate airports, and planned for contingencies countless times. Yet when it comes to life's most important decisions – how we invest our time and attention in this final leg of our career, and beyond – many of us operate on autopilot, assuming we'll have countless opportunities to course-correct later.


Here's what those old photographs reminded me: No matter your age or how full of life you feel, we're all approaching the end of some season. The senior captain nearing retirement knows this acutely. Some of the most meaningful people and experiences in your life are present only for a brief portion of your journey, and you'll see them no more once that chapter closes.


There will be a last time you read bedtime stories to your children before they outgrow that ritual. A final barbecue with siblings before life takes you to different cities. A last phone call with that friend from training who understood your career like no one else. A final beach walk with your faithful dog who's been your constant companion through good days and challenging ones. And yes, a last embrace from your parents.


THE DEEPER PURPOSE OF RETIREMENT PLANNING

This is where thoughtful financial planning reveals its true value. It's not merely about optimizing retirement accounts or achieving strong investment returns, though those matter tremendously for pilots navigating an industry known for volatility. The real value lies in how planning raises your awareness of life's finite nature and helps you make intentional choices about what matters most as you transition into your next chapter.


When we engage in comprehensive planning, we're creating a roadmap for your ideal retirement. We identify your true destinations – not just the financial milestones like RMDs or pension maximization, but the relationships you want to nurture, the adventures you want to share, and the legacy you want to leave. This process naturally directs your attention toward spending both your wealth and your time wisely in pursuit of experiences with those you love most.


YOUR ASSIGNMENT: THE MID-CAREER/PRE-RETIREMENT CHALLENGE

As you prepare for your next rotation, I want to challenge you with what I call "the midsummer assignment." It's simple in concept but profound in impact:


Take inventory of your "lasts" while they're still "nexts."


Consider the people and experiences that matter most to you as you contemplate retirement. That aging parent who lights up when you visit. The child who still wants to hear your stories from work. The spouse who deserves more than the tired version of you that often comes home after a long trip. The friends who knew you before you earned your stripes.


These relationships and experiences deserve the same careful attention you give to pre-flight checks and route planning. They require intentional investment, not just leftover time and energy.


BUILDING YOUR PERSONAL STRATEGY FOR YOUR NEXT CHAPTER

Here's what I've learned from helping pilots plan for their most important outcomes: The goal isn't to count how many meaningful experiences you have left – it's to ensure the ones you choose align with your definition of a life well-lived.


This summer, as you're enjoying those precious days off between trips, consider creating what I call your "Life Strategy." Just as you wouldn't depart on a significant flight without knowing your destination and fuel requirements, don't navigate through this pivotal season without clarity on:

  • What experiences matter most to you right now as you approach retirement?

  • Which relationships deserve more of your time and attention in this next phase?

  • How can your financial resources better support the life you actually want to live after the uniform comes off?

  • What would you regret not doing if this season ended sooner than expected?


THE PRACTICAL APPLICATION

As professional aviators, you understand that the most successful journeys are those planned with both precision and flexibility – detailed enough to handle the expected, adaptable enough to manage the unexpected. Your retirement deserves the same careful attention.


Financial planning, done right, becomes the tool that helps you answer these deeper questions. It's not just about having enough money to retire comfortably (though that's certainly important). It's about having the clarity and resources to make choices that align with your values while you're still vibrant and young enough to enjoy them.


DON'T FORGET TO DOCUMENT THE JOURNEY

Here's my final piece of advice, learned from sifting through decades of family photos: Take those pictures. Capture those ordinary moments that will become extraordinary memories. Future you will thank present you for creating that visual record of a life well-lived.


Time may be our most finite resource, but with thoughtful planning, we can ensure we're investing it in experiences and relationships that truly matter. After all, the richest retirement accounts can't buy back a single moment with someone you love.


Our family photos weren't just images – they were evidence of a life intentionally lived, of moments prioritized, of relationships invested in. They were the dividends of good planning, both financial and personal.

ree

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