Retirement Planning Roadmap | Still Waters Investment Strategies

Still Waters Investment Strategies

Retirement Planning Roadmap

An 8-step checklist to help you move from retirement questions to a clear, actionable plan.

1

Clarify Your Retirement Vision

Before crunching numbers, start with the “what” and “where” of the life you want to live. Your preferred retirement timing, location, and lifestyle drive how much you need to save and invest.

Target Age Hard Stop vs. Phased 🎯
Lifestyle Travel | Family | Hobbies 🏖️
2

Know Your Numbers

Estimate annual spending by separating essential “Needs” from discretionary “Wants”. Map out all income sources like 401(k)s, IRAs, Social Security, and Pensions.

Typical Retiree Expense Breakdown

Illustration only. Your actual numbers will vary.

3

Optimize Savings & Investments

Use tax-advantaged accounts and maximize contributions (including catch-ups for those 50+). As retirement nears, gradually shift your portfolio toward stability to manage market volatility.

Investment Glide Path Strategy

Adjusting risk over time can help manage sequence of returns risk.

4

Plan Income & Withdrawals

Coordinate Social Security timing with pensions and portfolio withdrawals to create a sustainable income plan. Delaying SS benefits until 70 provides a permanent increase in monthly payments compared to early claiming.

Social Security Timing Scenarios

5

Plan for Healthcare & Coverage Gaps

Healthcare can be a major expense in retirement. Prepare for the gap between early retirement and Medicare eligibility at 65. Understand how Medicare, supplements, and long-term care fit your situation.

The Medicare Gap

Coverage options for retirees under 65:

  • • COBRA or employer coverage
  • • Marketplace or private plans
  • • Strategic HSA catch-up use

65+ Roadmap

Core components of Medicare:

  • • Part A & B Enrollment
  • • Medigap or Advantage
  • • Part D Prescription
6

Reduce Debt & Fixed Costs

Cutting fixed monthly costs takes some pressure off your investment portfolio and can give you breathing room in during market dips. Focus on paying off high-interest debt and potentially paying down your mortgage.

Monthly Income Need Comparison

7

Update Estate & Legal Docs

Make sure your legacy plan is up to date. That means reviewing your will, powers of attorney, and healthcare directives. Double‑check that your beneficiaries match your intentions.

📜 Wills & Trusts
⚖️ Power of Attorney
🏥 Healthcare Directives
8

Emotional & Lifestyle Readiness

Retirement is as much a mental shift as a financial one. Take time to picture what your days will look like—how you’ll spend your time, maintain routines, and nurture relationships. Talk with your partner about shared goals so your lifestyle and expectations stay in sync.

Relationships

  • 🫂 Family
  • 🏘️ Community
  • 🎉 Social Activities
  • 🔗 Staying Connected

Purpose

  • 🎁 Service
  • 🎨 Creativity
  • 💼 Work
  • 🔥 Meaningful Pursuits
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© 2026 Still Waters Investment Strategies LLC. All rights reserved.

This roadmap is for educational purposes only and is not individualized investment, tax, or legal advice. For guidance specific to your situation, consider working with a fiduciary financial advisor.