Beyond the “Best Of” Lists: A New Blueprint for Choosing Your Perfect Place to Retire

The Spreadsheet of Anxiety

My name is Alex, and for the better part of a year, my partner and I lived in a state of quiet panic, governed by what we grimly called the “Spreadsheet of Anxiety.” We were in our late 50s, both with fulfilling careers, and the finish line—retirement—was finally in sight.

But instead of excitement, we felt a creeping dread.

The question “Where should we live?” had morphed from a happy daydream into a monumental, paralyzing task.

Our spreadsheet was a testament to our diligence, and our folly.

It had dozens of tabs, each one a different “Best Places to Retire” list from a reputable source.¹

We had data from Forbes, Kiplinger, U.S. News, and more, all cross-referenced and color-coded.

Yet, the more data we added, the more confused we became.

One list crowned a small city in Pennsylvania as the undisputed champion of retirement.³

Another insisted that New Hampshire, with its chilly winters and high taxes, was the true paradise.⁴

A third suggested we consider San Francisco, with a median home price of $1.29 million.⁵

The lists weren’t just disagreeing; they were presenting fundamentally different versions of reality.

This wasn’t an error.

It was a symptom of a deeply flawed process.

We realized these lists were answering the wrong question.

They were asking, “What is the best place?” based on their own internal, often hidden, priorities.

The real question we needed to answer was, “What is the best process for us to find our place?”

Trusting the standard advice, we decided to “test drive” a highly-ranked city in the sun belt, praised for its low taxes and glorious weather.

We followed the playbook, planning a week-long visit to “live like a local”.⁶

The reality was a crushing disappointment.

The promised “vibrant community” felt like a collection of disconnected subdivisions.

Life was impossible without a car, a constant cycle of driving from one strip mall to another.

The cultural scene, so lauded in the brochure, felt superficial.

We returned home not just disappointed, but defeated.

The standard advice wasn’t just unhelpful; it was actively leading us astray.⁷

We were meticulously analyzing the

what—the location—before we had even begun to understand our why.

It was in dissecting this failure that we uncovered the illusion of objectivity baked into these lists.

We saw that publications produce wildly different rankings using similar data points—cost of living, healthcare, crime rates.³

The difference wasn’t the data, but the

weighting.

U.S. News, for example, openly states that affordability is the most heavily weighted factor in its 2024 rankings.³

Another list might prioritize the number of golf courses or sunny days.

By trusting these lists, we were outsourcing the most critical part of our decision: defining our own values.

Our test visit failed because the list’s values were not our values.

The Epiphany: Your Retirement is a City, and You are the Urban Planner

The breakthrough came when I finally closed the spreadsheet.

I stopped thinking like a consumer picking a product off a shelf and started thinking like a designer creating a complex, integrated system.

The “aha” moment arrived from a field that seemed utterly unrelated to retirement: Urban Planning.⁹

A great city isn’t just a random collection of nice buildings and parks.

It’s a holistic system built on a master plan, with deliberate zoning for different activities, essential infrastructure to support its population, and a clear vision for its future.

It balances the needs of today with the demands of tomorrow.

Our retirement, we realized, deserved the same thoughtful design.

This insight gave birth to a new paradigm, a framework we called “Retirement Life-Design.” It replaces the chaotic, list-driven approach with a structured, four-pillar process modeled on the principles of urban planning.

• Pillar 1: Strategic Master Planning: Defining your high-level goals, values, and vision for your life. This is your “why.”
• Pillar 2: Land-Use & Zoning Analysis: Surveying the domestic and international landscape to find regions that align with your master plan.
• Pillar 3: Infrastructure & Connectivity Audit: Assessing the hidden systems—healthcare, social networks, financial plumbing—that make daily life possible and fulfilling.
• Pillar 4: Prototyping & Phased Development: Testing your chosen location like a pilot project before making a full-scale commitment.

The power of this framework can be understood through a simple physics analogy.

Trying to choose a location by scrolling through endless lists is like trying to push a massive, heavy wheel by shoving it at the axle—it’s exhausting, inefficient, and you barely move.

Using a proper framework is like applying force to the top of the wheel, using it as a lever.¹¹

It gives you mechanical advantage, transforming an overwhelming problem into a manageable one.

Pillar 1: Drafting Your Master Plan – The Non-Negotiable First Step

Before you look at a single map or real estate listing, you must draft the master plan for your life.

This is the most critical and meaningful part of the process, turning vague hopes into a defined, actionable vision.¹²

This is where you stop looking outward at places and start looking inward at yourself.

Defining Your “Big Rocks” and Lifeview

A famous analogy illustrates the art of prioritization perfectly.¹³

Imagine a jar.

If you fill it with sand first, there’s no room for the pebbles or the big rocks.

But if you place the big rocks in first, then the pebbles, the sand can fill the empty spaces around them.

The jar is your life.

The sand is the small stuff.

The pebbles are the other things that matter, like work or hobbies.

The

“Big Rocks” are your non-negotiables: your health, your key relationships (partner, family, friends), and your sense of purpose.

To identify these, we borrowed from the “Designing Your Life” framework developed at Stanford.⁹

We created a simple dashboard to assess the four key domains of life:

Work, Play, Love, and Health.

What does a balanced, thriving life look like for you across these areas? This isn’t about finding a place that will give you these things; it’s about defining what you need before you even start your search.¹⁶

Planning for Evolving Timelines: The Three Stages of Retirement

A catastrophic mistake in retirement planning is designing for a single moment in time.

Retirement isn’t a permanent vacation; it’s a 20- to 30-year journey with distinct phases.

Most people go through three stages: the active “Exploring” (or “Go-Go”) years, the quieter “Nesting” (“Slow-Go”) years, and the later “Reflecting” (“No-Go”) years, where health and support become primary concerns.¹⁷

Your master plan must account for this evolution.

A remote mountain cabin that’s perfect for the “Go-Go” years could become a prison of isolation during the “No-Go” years, when walkability, community, and easy access to top-tier healthcare are no longer luxuries but necessities.

The location you choose must be resilient and adaptable enough to support you through all three stages.

The Personal Zoning Ordinance

To translate these abstract ideas into a practical tool, we created our “Personal Zoning Ordinance.” This simple worksheet became our compass, the tangible expression of our master plan.

It is the tool that allows you to build your own “best of” list, with weightings that reflect your unique life.

The Personal Zoning Ordinance Worksheet

Domain	My Non-Negotiable Minimum	My Ideal/Aspirational Goal	My Personal Weighting (1-5)
Financial	Monthly housing cost under $X. State does not tax Social Security.	Low overall tax burden. Low cost of living.
Healthcare	Within 45 minutes of a major, well-regarded hospital system.	Walkable to a GP. Abundant in-network specialists for my needs.
Social	Evidence of active community groups (clubs, volunteer orgs).	Walkable to a vibrant downtown with cafes, bookstores. Strong sense of local community.
Climate	No extreme heat (over 95°F for more than 30 days/year).	Four distinct, mild seasons.
Lifestyle	Access to nature/hiking trails within a 30-min drive.	A rich arts and culture scene (live music, theater). Lifelong learning opportunities.

Completing this worksheet is the single most important action you can take.

It forces you to define your “Big Rocks” and assign them a personal value, creating the unique lens through which you will evaluate every potential location.

Pillar 2: Land-Use Analysis – Surveying the Domestic & International Landscape

With your “Personal Zoning Ordinance” in hand, you can now begin to survey the “land” of potential retirement locations.

The goal is not to find a single “best” place, but to identify location archetypes that align with your master plan.

You are now matching the map to your blueprint, not the other way around.

The U.S. Landscape: A Nation of Diverse ‘Zones’

The United States offers a vast and varied landscape for retirees.

Instead of seeing it as 50 states, think of it as a collection of distinct retirement models, each with its own profile of pros and Cons.

• The College Town Model (e.g., Columbia, MO; Lawrence, KS): These locations offer a potent mix of excellent healthcare infrastructure (often tied to a university hospital), a vibrant cultural scene, lifelong learning opportunities, and a stable local economy.⁸ The trade-offs can include a more transient population and a social calendar that revolves around the academic year.¹⁹
• The Tax-Friendly Model (e.g., Mississippi, Wyoming): The appeal here is purely financial, with states offering no tax on Social Security and other retirement income.⁴ However, this can be a dangerous trap. A state like Mississippi, while ranked the most tax-friendly, consistently ranks near the bottom for healthcare access and outcomes.²⁰ This creates a critical trade-off: a low tax burden is meaningless if your healthcare costs skyrocket due to a lack of quality, accessible care. This highlights the necessity of a holistic framework over a single-metric analysis.
• The Four-Season/New England Model (e.g., New Hampshire, Maine): While often overlooked for their climate, these states are praised by some analysts for top-tier safety, excellent healthcare, and a strong sense of community.⁴ For a retiree whose “Zoning Ordinance” weights safety and community higher than sunshine, this model becomes a leading contender despite potentially higher taxes on some income.
• The Renter’s Model (e.g., Tallahassee, FL; Columbus, OH): For those who prioritize flexibility and low maintenance, certain cities offer a more affordable rental market. This provides access to community amenities like pools and fitness centers without the burdens of homeownership, and serves as an excellent strategy for prototyping a location long-term.¹⁹

The International Frontier: High Reward, High Complexity

Retiring abroad is not just a change of scenery; it’s an emigration into an entirely new legal, financial, and social ecosystem.

The potential rewards are immense, but so is the complexity.

• The European Dream (e.g., Portugal, Spain, Greece): The allure is a blend of lower cost of living, access to high-quality public healthcare for legal residents, and an unparalleled richness of culture and history.²¹ In places like Lisbon, a couple can live comfortably for a fraction of the cost of a major U.S. city, with access to the national health service (SNS) once residency is established.²³
• The Latin American Haven (e.g., Ecuador, Costa Rica, Panama): These countries are famous for their extremely low cost of living, welcoming retirement visa programs, and established expatriate communities.¹ In a city like Cuenca, Ecuador, a couple can thrive on less than $2,000 a month, enjoying affordable private healthcare and a large, supportive network of fellow expats.²⁷

Living abroad, however, presents a critical strategic choice that goes beyond finances: the choice between the “expat bubble” and true integration.

Many popular destinations like Cuenca or Portugal’s Algarve region have large, vibrant English-speaking communities.²⁹

This provides a ready-made social safety net, which is a powerful draw for those seeking community.³²

Yet, this comfort can become a crutch, creating a bubble that insulates you from the local culture and prevents true integration.

Living in a foreign country where you don’t speak the language outside of a small circle of fellow foreigners can eventually feel less like living and more like being a permanent tourist.

A successful international plan must consciously address this: is the goal to find a home-away-from-home, or to truly build a new home in a new culture?

Retirement ‘City Model’	Approx. Monthly Cost (Couple)	Housing Model	Healthcare System	Tax Friendliness (US Retiree)	Community & Social Fabric
US College Town	$3,500 – $5,000	Buy/Rent	Medicare + Private	Varies by State	Integrated, Town/Gown Mix
US Tax-Friendly State	$3,000 – $4,500	Buy	Medicare + Private	High	Varies, can be isolating
European Capital (Lisbon)	$2,700 – $3,800 33	Rent/Buy	Public (SNS) + Private	Moderate (Treaty)	Expat groups & Local
LatAm Expat Haven (Cuenca)	$1,500 – $2,000 27	Rent/Buy	Private + Public (IESS)	High (Foreign income focus)	Strong Expat Bubble

This table allows you to hold your “Personal Zoning Ordinance” up against these distinct models of living to see which archetype is the best preliminary fit for your master plan.

Pillar 3: Infrastructure & Connectivity Audit – The Systems That Make Life Work

A beautiful city with crumbling roads and unreliable power is unlivable.

The same is true for your retirement location.

The most beautiful view in the world won’t make you happy if you can’t see a doctor or make friends.

This pillar audits the critical, often invisible, systems that are the primary source of relocation regret.³²

Healthcare Infrastructure: Beyond “Good Hospitals”

This is about the entire healthcare ecosystem, not just the ranking of the nearest hospital.

• In the US: You must understand the intricate and often costly reality of the American system. Medicare is your foundation, but it’s not all-encompassing.³⁷ You will need supplemental plans, and out-of-pocket costs can be staggering.¹⁷ A state with a low cost of living might have fewer in-network specialists for your specific condition, forcing you to travel and pay more, negating the initial savings.
• Abroad: This is a fundamental system change. Medicare will not cover you.³⁸ Your two paths are purchasing private international health insurance or qualifying for the national system of your new country.²¹ This requires a deep dive into the specifics. For example, an American retiree in Portugal must obtain a residency permit, register with their local
  Junta de Freguesia (parish council), and then apply for a health number (Número de Utente) to access the public SNS system.²⁵ This is a bureaucratic process that is a critical piece of infrastructure to audit before you move.

Social Infrastructure: The Number One Cause of Relocation Regret

This is the most important, and most tragically underestimated, piece of infrastructure.

Countless stories from forums and articles tell of people who moved to their financial or climatic “dream” location only to find themselves profoundly lonely and even clinically depressed.³²

The “Seattle Freeze,” a local term for the difficulty of making new friends in that city, shows that even in a beautiful, dynamic place, community is never guaranteed.³²

You cannot be passive about this.

You must have a deliberate plan to build your social infrastructure.

This audit begins before you move.

Join online forums and Facebook groups for your target locations to get a feel for the community.²⁹

Research local clubs, volunteer organizations, and lifelong learning programs like the Osher Lifelong Learning Institute (OLLI) network.³⁷

The goal is to arrive with a pre-researched list of potential connection points, turning the hope for community into an actionable strategy.

Financial & Legal Infrastructure: The Hidden Bureaucracy

This is the plumbing and wiring of your retirement life.

If it’s faulty, everything grinds to a halt.

• Abroad: This is where the international dream meets bureaucratic reality. The United States taxes its citizens regardless of where they live, meaning you will likely file taxes in two countries.³⁸ Complex tax treaties may not cover all your assets; retirement accounts like Roth IRAs and HSAs can be subject to foreign taxes.⁴¹ You will need to maintain both U.S. and local bank accounts, navigating regulations like the Foreign Account Tax Compliance Act (FATCA).³⁸ Most critically, your U.S.-based will, trust, and powers of attorney may be completely invalid abroad, requiring you to create new legal documents, such as a “situs” will, under the laws of your new country.³⁹
• At Home: Even a domestic move requires an audit. If considering a senior-only community, you must investigate the history of fee increases for things like HOAs, amenities, and meal plans, as these “quietly increasing” costs can wreck a fixed-income budget over time.⁴² If looking at a Continuing Care Retirement Community (CCRC), you must scrutinize the contract to understand the fee structure and what happens to your large entry fee if you move or need a higher level of care.³⁶

Pillar 4: Prototyping & Phased Development – Test Before You Invest

No urban planner would break ground on a new city without extensive modeling and pilot projects.

Likewise, you must “prototype” your retirement life before making an irreversible commitment.

This requires more than a simple vacation.

The “Worst Season” Visit

The standard advice is to visit your short-listed locations.

The expert advice is to visit during the absolute worst time of year.⁶

If you’re considering Phoenix, go in August.

If you’re drawn to Vermont, book a trip for February.

This strategy tests your tolerance for the location’s single biggest drawback.

It prevents you from being seduced by a perfect week in May and forces you to confront the reality of the other 11 months.

If you can still see yourself being happy during the worst season, you have a much more robust data point.

The Immersion Test: Live Like a Local

If a location passes the “Worst Season” test, the next step is a deep immersion prototype.

Rent an apartment or house for at least a month, not a hotel.⁷

Your mission during this time is to rigorously simulate your daily life, not to be a tourist.

• Shop at the local grocery stores and farmers’ markets.
• Navigate the city using only public transportation or by walking.
• Spend time at the public library or community center.
• Using the contacts you made in your Pillar 3 audit, schedule coffee with people from local expat or community forums. Ask them pointed questions about the pros and cons of daily life.
• Try to perform a simple bureaucratic task, like inquiring about a driver’s license or making a non-urgent doctor’s appointment, just to experience the process.

This prototype provides invaluable, real-world qualitative data that no spreadsheet can ever capture.

It is the ultimate test of the infrastructure you’ve audited, moving your plan from theory to practice.

Conclusion: Breaking Ground on Your New Life

After our disastrous first trip, my partner and I threw out the “Spreadsheet of Anxiety” and committed to our new “Urban Planning” framework.

The process was transformative.

Our “Personal Zoning Ordinance” revealed that our “Big Rocks” were a vibrant cultural life, walkability, and top-tier healthcare access, with a moderate weighting on four-season weather and a lower weighting on tax friendliness.

This led us to an unexpected conclusion.

We bypassed the sun belt and the big-name international hotspots.

Our framework pointed us toward a mid-sized, culturally rich university town in a region we had never seriously considered.

We did our “worst season” visit (in a damp, grey November) and followed it with a month-long immersion rental the next spring.

We walked everywhere, audited the healthcare system, and built fledgling connections through a local hiking club and the university’s lifelong learning program.

It felt right.

It felt like a city designed for us, because we had designed ourselves first.

We made the move two years ago, and it has been a resounding success.

The process worked.

The point of this journey is not to tell you where to retire.

It is to give you a better process for discovering that for yourself.

The endless “best of” lists make us passive consumers in the most important life design project we will ever undertake.

They encourage us to look for a pre-packaged solution instead of building a custom one.

The “Retirement Life-Design” framework changes that.

It puts the power and the responsibility back in your hands.

It transforms you from a confused consumer into the Chief Architect of your future.

The data is out there, the options are limitless, but without a blueprint, you’re just piling up bricks.

So, throw away the lists.

Pick up your tools.

It’s time to start designing.

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