The “To” Question: What Do You Want to Retire “To”?
One of the most powerful questions I ask clients is: What are you retiring “to”?
Rather than focusing solely on escaping work or daily responsibilities, this question helps paint a vivid, realistic picture of life in retirement. The more details we explore—daily routines, hobbies, social connections, and environment—the clearer the vision becomes. Many couples start with vague ideas like “I just want to retire,” but through meaningful conversations, they uncover new topics and gain clarity on ideas they hadn’t fully considered.
A big part of the “To” is where will you live. It used to be that Florida was the default retirement destination. Today, the discussion is far more nuanced, weighing factors like:
– Tax-friendly policies
– Cultural fit and community vibe
– Proximity to major airports or transportation hubs
– Access to high-quality healthcare
– Cost of living
– Family closeness
– Weather preferences
In 2023, nearly one million Americans aged 60 and older crossed state lines to relocate, according to U.S. Census Bureau data analyzed in recent studies (e.g., SmartAsset’s 2025 report). Florida led with a net gain of over 44,000 retirees aged 60+, followed by states like North Carolina and Arizona. However, this represents a small fraction of the overall picture.
The vast majority of older adults prefer to stay put. Recent AARP surveys (including the 2024 Home and Community Preferences Survey) show that 75% of adults aged 50+ want to remain in their current homes as long as possible, and 73% hope to stay in their current communities. This aligns with broader trends: about 6.2% of adults 65+ move in a typical year (per older Census reports from 2015–2019 data), and of those moves, roughly 58% stay within the same county.
In regions like the Northeast, the preference for aging in place is even stronger, often cited at 75–94% in various studies and regional surveys, driven by established roots, family ties, and community familiarity. Nationally, rising costs (housing, maintenance, taxes) pose challenges, but many retirees adapt by modifying homes—adding grab bars, ramps, or smart technology—or exploring home-sharing to offset expenses.
Ultimately, developing a clear vision of what you’re retiring “to” guides decisions about location and lifestyle. I’ve walked many clients through this process, helping them make informed choices. My wife Susan and I even used it ourselves. Growing up in western Pennsylvania, I favored certain seasons and activities, while she was born on the Island of St. Thomas and has a very different perspective on weather and pace of life. Those honest discussions revealed a lot about our shared (and differing) retirement dreams—and helped us find common ground on where we want to settle.
If you’re approaching retirement, start with the “To” question. It sparks the right conversations and leads to more fulfilling decisions.
Close your eyes and describe your perfect ordinary Tuesday in retirement. Where are you waking up. What do you see out the window. What activities are you looking forward to on this ordinary Tuesday in retirement? Write it all down, no filters.
What does your retirement vision look like? I’d love to hear in the comments.
Schedule an introductory phone call with John at this link: John Simkins – Introductory Phone Call
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