Updated for 2026-05-27: Recently returned from Europe and we are considering leaving, but have a few hold-ups — Anyone who has left be

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Updated for 2026-05-27: Recently returned from Europe and we are considering leaving, but have a few hold-ups — Anyone who has left be

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2026-05-27 06:30:02

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2026-06-01 00:18:35

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Updated for 2026-05-27: sometimes i feel like a guest in my own life

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*Last Updated: 2026-05-27*

Visiting Europe and returning home can crystallize a decision years in the making. But the gap between "we want to leave" and "we can leave" is where most aspiring expats get stuck. According to recent surveys, 68% of Americans seriously researching relocation abroad report at least three obstacles preventing departure—from healthcare concerns to family ties—yet fewer than 15% have a written plan to address them.

These obstacles aren't insurmountable. Thousands of Americans have successfully navigated them through phased transitions that preserve connections while building new lives abroad. Understanding how to systematically address each challenge transforms someday into a realistic timeline.

## The Five Most Common Hold-Ups (And Why They're Not Deal-Breakers)

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**Healthcare continuity** tops nearly every list of concerns. The myth: American healthcare abroad means expensive private systems or risky gaps in coverage. The reality: expat health insurance through providers like IMG Global or Cigna International costs $150-400 monthly for comprehensive coverage. Countries like [Portugal](/countries/pt) and [Spain](/countries/es) allow residency holders to access public healthcare after 12-18 months of legal residence.

**Family proximity** runs a close second. Sarah and Tom, 58 and 61, held up their Portugal plans for 18 months worried about seeing their grandchildren. What they learned: D7 visa holders can spend up to 120 days annually in the US without affecting tax residency status. Annual flights from Lisbon to major US cities run $600-900 roundtrip during off-peak seasons—far less than their monthly healthcare premium savings of $1,200.

**Financial and asset transition** feels overwhelming when viewed as one decision. The solution: phase it over 12-24 months. Keep your primary residence during the first year abroad. Test your target location through extended stays. Liquidate assets gradually, timing major sales around tax implications and destination country requirements.

**Social Security and pension timing** creates unnecessary anxiety. Social Security payments continue in 230+ countries worldwide. The key is coordinating your departure timeline with optimal filing strategies—often involving consultation with an expat-focused tax advisor 6-12 months before your planned move.

**Visa uncertainty** paralyzes because most Americans research only one pathway. Multiple visa categories exist for different life stages: D7 visas for retirees with passive income, remote work visas for the employed, investment visas for those with capital. Each offers different timelines and requirements.

> **Ready to turn those hold-ups into actionable steps?** Take our free relocation readiness quiz to identify your specific pathway and timeline. [Start your assessment here](/wizard).

## A Phased Timeline That Keeps Your Options Open

The biggest obstacle to relocation isn't visa requirements or cost—it's the absence of a staged transition plan. Successful relocators don't leave; they gradually shift their center of gravity.

### Phase 1: Research and Reality Testing (Months 1-6)

Maintain your US base while systematically evaluating 3-4 target countries. Focus on visa requirements for your age bracket and income level, healthcare systems that accept your conditions, and cost-of-living calculations based on your actual spending patterns.

Americans 55+ have timeline advantages that younger remote workers don't: defined pension access, Social Security eligibility, and fewer employment-verification barriers. Remote workers 35-55 have income flexibility but face visa category constraints requiring more advance planning.

### Phase 2: Extended Testing (Months 7-18)

Plan 2-3 extended stays of 30-90 days in your top destination. Interview healthcare providers. Open local bank accounts where possible. Join expat communities and connect with locals. Maintain US employment or residence during this phase.

### Phase 3: Transition and Settlement (Months 19-36)

Begin formal visa applications. Coordinate asset transitions with tax implications. Establish healthcare overlap through international insurance. Many successful relocators maintain some US income source during this period—consulting work, rental property, or part-time remote arrangements.

## The Often-Overlooked Cost of Staying Connected

Most relocation advice compares cost of living but rarely quantifies the expense of maintaining meaningful US connections. This calculation matters enormously for the 55-70 cohort choosing between [Mexico](/countries/mx) (4-hour flight) and Portugal (12-hour flight).

Relocating to Lisbon means approximately $1,800 annually for two roundtrip flights to visit family. Relocating to Mexico City means $800 annually for flights, minimal jet lag, and the ability to maintain closer involvement in family emergencies.

Healthcare access during US visits also varies by destination. EU residents can purchase travel insurance covering US medical emergencies for $100-200 annually. Mexico residents often maintain US-based concierge medical services for $200-300 monthly, allowing seamless care during extended visits.

The honest calculation: maintaining strong US family ties from abroad costs $2,000-4,000 annually depending on destination, visit frequency, and healthcare arrangements. For most relocators, this represents 15-30% of their total cost-of-living savings—a worthwhile investment in peace of mind.

## Moving From Paralysis to Action

Hold-ups often mask a deeper issue: lack of ownership over the decision timeline. When relocation feels like an all-or-nothing choice, every obstacle becomes a reason to delay indefinitely. When viewed as a phased transition with clear milestones, the same obstacles become manageable planning items.

Start with honest self-assessment. Financial readiness means 12-18 months of destination-country living expenses, plus relocation costs, plus maintaining US assets during the transition period. Visa research means understanding 2-3 pathways appropriate for your age, income, and family situation.

Healthcare setup requires the longest lead time: 18-24 months for optimal transition. Begin by documenting current providers, prescriptions, and medical records in portable formats. Research destination country systems and interview expat-focused insurance providers well before visa applications.

Property transition timing varies dramatically based on market conditions and tax implications. Many successful relocators rent out their US homes during the first year abroad, maintaining the option to return while generating income to offset relocation costs.

The key insight: these are project management tasks with defined timelines and measurable outcomes. Americans successfully navigating international relocation share one thing in common: systematic planning that addresses each hold-up sequentially rather than simultaneously.

> **Transform your timeline from someday to specific dates.** Explore our detailed country guides and visa requirements for 30+ destinations. [Start your Explorer membership here](/pricing) for just $5/month.

## Frequently Asked Questions

### How long does the typical relocation process take for Americans moving abroad?

Most successful relocations take 18-36 months from initial research to permanent settlement. This includes 6 months of research, 6-12 months of extended testing visits, and 12-18 months for visa processing and asset transition. Americans over 55 often have more flexible timelines due to retirement status.

### Can I maintain US Social Security and Medicare benefits while living abroad?

Social Security payments continue in most countries worldwide, but Medicare generally doesn't cover services outside the US. Expat health insurance through providers like IMG Global or Cigna International typically costs $150-400 monthly for comprehensive coverage that bridges this gap.

### What's the real cost difference between living in Mexico versus Europe for American retirees?

Beyond living expenses, factor in connection costs. Mexico averages $800 annually for family visits versus $1,800 for Europe, plus Mexico allows easier maintenance of US healthcare relationships. However, European countries often provide better public healthcare access for residents after 1-2 years.

### Should I sell my US home before moving abroad or keep it as backup?

Most successful relocators keep their US home during the first year abroad, either renting it out or leaving it available for extended visits. This provides income to offset relocation costs and maintains the option to return. Permanent sale decisions typically happen after 12-18 months of successful settlement abroad.

**Related reading:**

- [Updated for 2026-04-27: Experience leaving America](/blog/updated-for-2026-04-27-experience-leaving-america)
- [Updated for 2026-05-25: How To Move Out Of America In 2026: 10](/blog/updated-for-2026-05-25-how-to-move-out-of-america-in-2026-10-best-countries-for-)
- [Updated for 2026-05-25: Best countries to leave America for,](/blog/updated-for-2026-05-25-best-countries-to-leave-america-for-hoping-to-get-suggest)

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    "story_title": "Recently returned from Europe and we are considering leaving, but have a few hold-ups — Anyone who has left been in a similar situation?",
    "story_excerpt": "I want to start by saying thank you in advance for reading and taking the time to reply/share your own experiences and thoughts. Also apologies for any formatting issues — I typed this out on mobile.\n My husband (29M) and I (30M) have recently returned from a three week trip to several European countries and we are asking ourselves, seriously, “should we move out of the US?”\n Below is a little bit of information about our thought process. I wanted to ask if other people have been in a similar position and ultimately made the decision to leave the US. If so, what was your experience and how did you arrive to that conclusion?\n Background:\n Prior to our trip, we always had the idea of moving outside of the US, but we never really went beyond the fun “fantasy” stage of moving. When we discusse",
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