Recently, someone asked me how I envision my retirement lifestyle 20 years from now. And I realized something remarkable: it’s already exactly how I live today. The freedom to spend meaningful time with my family, pursue hobbies, travel, and explore new experiences — that lifestyle isn’t waiting for some future date. I’m already living it.
In Photo: David Wheatley's Tidewater Wealth Management Hat pictured with a part of the Grand Canyon in the background. Photo taken August 2025 at the Grand Canyon, Arizona, USA
I’ve been blessed to know early on what truly matters to me and, through careful planning and prioritization, have had the capacity to start living that life well before the traditional “retirement age.”
For me, that vision includes:
- Traveling with each of my kids when they turn 16 — creating unforgettable adventures and memories together.
- Skiing 20 days each year, soaking in the joy of fresh powder and the outdoors.
- Cooking and learning in Italy and France — immersing myself in local culture and culinary experiences.
These aren’t just bucket-list items; they’re intentional choices that reflect my priorities and values. And they serve as a reminder that retirement isn’t just about stopping work — it’s about shaping a life that aligns with your purpose and passions.
In Photo: David Wheatley with his kids in Grand Canyon, Arizona 2025
Of course, every individual’s vision is different. Some may want to pursue new careers, focus on philanthropy, live abroad, or enjoy quiet time with loved ones. The point is this: you don’t have to wait until retirement to start living the life you want. Knowing your “Why” — the guiding purpose behind your decisions — allows you to align your time, resources, and energy with what matters most.
When I work with clients, I encourage them to think beyond their financial statements. What does retirement really look like for them? What experiences, relationships, and milestones will define their future? Financial planning, in this sense, becomes a tool not just for security, but for freedom — the freedom to create the lifestyle you value.
For me, living my retirement lifestyle today gives me perspective and confidence when planning for the future. It reminds me that with clarity, intention, and proper guidance, we can all make choices that let us live fully — now and later.
So, whether it’s traveling with your family, pursuing a long-held passion, or simply having more time to be present with loved ones, the question to ask yourself is: what does your retirement really look like? And how can you start living it today?
About The Author
David Wheatley is a founding partner and senior wealth management advisor at Tidewater Wealth Management with more than 28 years of experience in financial planning and portfolio management. He holds multiple professional licenses and advanced designations, including Chartered Financial Consultant (ChFC) and Chartered Life Underwriter (CLU). Before Tidewater, he advised clients at TIAA Financial Services, where he managed portfolios totaling over $1 billion and developed deep expertise in tax-efficient income distribution strategies.
Outside of his career, David is a proud father of five and an active member of his community. He has coached local lacrosse and soccer, serves as a Connecticut State Certified First Responder with the Easton Volunteer Fire Company, and enjoys outdoor pursuits like boating, SCUBA diving, skiing, and staying active.