Sherrill Wealth Management

Your Retirement Milestone Timeline

Key ages and planning opportunities on the path to — and through — retirement

Age-based rule or benefit

Planning conversation to consider

Ongoing Planning Conversations

Long-Term Care Planning (Ages 55–65) Social Security Earnings Test (Ages 62–FRA) Beneficiary & Estate Document Review Annual Medicare Plan Review

Sherrill Wealth Management

Your Clarity Timeline

The map — see what's coming and when

Let's personalize your timeline

Enter a name and date of birth to see upcoming milestones. Target retirement age is optional — add it to see how your dates line up.

Personal Details

First Name

Date of Birth

Target Retirement Age optional

Already receiving Social Security

Sherrill Wealth Management

The Retirement Action Checklist

Managing income · Optimizing healthcare costs · Making smart annual updates

Sherrill Wealth · 2026

AGE 65 Triggered by a specific age — applies regardless of when you retire

RETIREMENT DATE Triggered by your chosen retirement date — timing is within your control

6p 4s Linked Roadmap module(s) — see Our Approach tab for the full pillar map

Module legend — click to expand

Groundwork (Discovery)

1g · Priorities & Assumptions

2g · Expectations & Coverages

3g · Intent & Structure

4g · Life Priorities

5g · Tax Return Review

6g · Income Inventory

7g · Risk Boundaries

8g · Portfolio Assessment

9g · Personal Financial Statement

Protections (Onboarding · First 100 Days)

1p · Stress Testing

2p · Longevity Plan / LTC

3p · Decision Continuity

4p · Cash Flow Margin

5p · Tax Targets

6p · Income Floor

7p · Liquid Reserves (Shield)

8p · Diversified Growth (Sword)

9p · Strategic Capital (Dagger)

Strategies (Progress Meeting Rotation)

1s · Plan Adjustments

2s · Anticipated Pivots

3s · Legacy & Gifting

4s · Contributions & Distributions

5s · Proactive Tax Strategies

6s · Active Management

7s · Strategic Reallocation

8s · Strategic Rebalancing

9s · Balance Sheet Optimization

Sherrill Wealth Management

Our Approach

The whole system — three decisions, nine areas, and the deliverable behind every step. Click any decision, phase, or module to explore.

Open the roadmap full-screen ↗

Sherrill Wealth Management

Retirement Readiness Scorecard

Eighteen quick choices across the three pillars and nine areas — a clear picture of where you stand, in about five minutes.

Open the scorecard full-screen ↗

Your Retirement Milestone Timeline

Your Clarity Timeline

Personal Details

Spouse / Partner Details

The Retirement Action Checklist

Our Approach

Retirement Readiness Scorecard