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Your Retirement Stages

From Building Wealth to Enriching Your Legacy

Your retirement journey isn’t one-size-fits-all. Your needs evolve through distinct stages, each with its own financial priorities, health considerations and legacy goals. Whether you’re in your Earn, Enjoy or Enrich years, we guide you with strategies for where you are today and where you’re headed tomorrow.

Retirement Protectors Retirement

Earn · Ages 59–64

The Wealth-Building Decisions You Face in Your Earn Years

Your Earn years are a critical transition. You’re approaching retirement, maximizing your earning potential and making crucial decisions about Social Security, pension benefits and retirement timing: when to claim (as early as 62 or as late as 70), how to move from employer health coverage to Medicare, and how to build your retirement income strategy.

  • Social Security Claiming Strategy

    Analyze the right age to claim based on your health, longevity, spousal coordination and tax implications.

  • Retirement Transition Planning

    Coordinate the shift from employer benefits to retirement coverage, including bridging health insurance before Medicare at 65.

  • Wealth Accumulation

    Maximize retirement contributions, tax-advantaged savings and catch-up provisions before your retirement date.

  • Income-Generation Strategy

    Develop a sustainable withdrawal strategy from your retirement accounts, balancing tax efficiency with income needs.

Midwest Medigap Medicare

Enjoy · Ages 65–75

The Health & Lifestyle Decisions You Face in Your Enjoy Years

Your Enjoy years are often called the “go-go years”: the health, energy and freedom to travel, pursue hobbies and spend time with family. At 65 you face one of the most important enrollment decisions of your retirement, choosing the right Medicare coverage. It affects your costs, your access to providers and your prescription coverage, and we guide you through it with education and recommendations built around your health needs and budget.

  • Medicare Enrollment (Age 65)

    Navigate your seven-month initial enrollment period, understand Parts A, B, C and D and avoid lifetime penalties.

  • Part B Timing

    Coordinate with employer coverage if you’re still working, understand special enrollment periods and time your enrollment.

  • Coverage Type

    Choose between Medicare Advantage and Original Medicare with a Medigap plan, based on your health needs, provider preferences and budget.

  • Prescription Drug Coverage (Part D)

    Select the Part D plan that covers your medications while keeping out-of-pocket costs down.

  • Annual Review

    Reassess your coverage every year during the Annual Enrollment Period, October 15 to December 7.

Retirement Protectors Retirement

Enrich · Ages 75+

The Legacy Decisions You Face in Your Enrich Years

In your Enrich years, priorities shift from active pursuits to legacy: dignity in care, empowering the next generation and a lasting impact on the causes you care about. We help you handle these sensitive decisions with compassion and practical solutions.

Care: Protecting Your Dignity

  • Long-term care planning and funding strategies
  • End-of-life care directives and healthcare powers of attorney
  • In-home care vs. assisted living vs. skilled nursing decisions
  • Medicaid planning and asset protection strategies
  • Care coordination with family members

Children: Empowering the Next Generation

  • Wealth transfer strategies: gifting, trusts, beneficiary designations
  • Minimizing estate taxes and maximizing inheritance value
  • Equitable vs. equal distribution strategies
  • Family communication and passing on values
  • Protecting inheritances from creditors, divorce and mismanagement

Charity: Making a Lasting Impact

  • Charitable giving strategies: outright gifts, donor-advised funds, charitable trusts
  • Tax-efficient giving through Qualified Charitable Distributions (QCDs)
  • Legacy endowments and memorial gifts

Your Retirement Journey, Stage by Stage

StageAgesPrimary FocusKey DecisionsCoverage Lead
Earn59–64Building WealthSocial Security timing, retirement preparation, wealth accumulationProsper
Enjoy65–75Active LivingMedicare enrollment, healthcare decisions, active lifestyle fundingProtect
Enrich75+Legacy ImpactCare planning, wealth transfer, charitable givingPreserve

Your Journey. Our Expertise.

At every stage of your retirement, your TAG team is here to guide you with personalized strategies and proactive service.

One Team. One Contact. We’re Your People™