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Start Here: Your First Year of Retirement

Follow these 6 steps to navigate retirement with confidence. Click any step to expand.

1

💵 Establish Your Withdrawal Strategy

Shift from accumulation to distribution mode

After decades of accumulating, you now need to shift to distribution mode. How you withdraw is just as important as how much—the wrong approach can cost you hundreds of thousands in taxes and longevity.

  • The 4% Rule: Withdraw 4% of your portfolio in year one, then adjust for inflation. A guideline, not a law.
  • Tax-Efficient Order: Generally taxable accounts first, then tax-deferred (401k/IRA), then Roth—but this varies.
  • Bucket Strategy: Keep 1-2 years of expenses in cash so you don't sell stocks in a down market.
  • Flexibility: Be willing to adjust spending based on market conditions.

✓ Your Action

Define your withdrawal strategy: which accounts to draw from, in what order, and how much. Set up your cash bucket.

🌿 Consider "dynamic spending" rules: cut spending by 10% if your portfolio drops 20%, increase if it grows significantly. Flexibility dramatically improves portfolio survival rates.

2

🏥 Enroll in Medicare (If 65+)

Don't miss your enrollment window

If you're 65 or older, Medicare is now your primary health insurance. Miss your enrollment window and you'll face permanent penalties and coverage gaps.

  • Initial Enrollment: 7 months centered on your 65th birthday
  • Part A: Hospital insurance (usually free)
  • Part B: Medical insurance (~$175/month in 2025)
  • Part D: Prescription drug coverage (separate plan)
  • Choice: Original Medicare + Medigap, OR Medicare Advantage

✓ Your Action

If 65+, enroll in Medicare Parts A, B, and D. Research Medigap vs. Medicare Advantage. If under 65, secure bridge coverage through COBRA, ACA, or spouse's plan.

🌿 Healthcare is your most valuable asset in retirement. Invest time in understanding your options—this decision affects decades of coverage.

3

📊 Execute Your Social Security Plan

Implement your claiming strategy

If you planned to delay Social Security, stick to the plan (assuming circumstances haven't changed). If claiming now, here's what to know:

  • Apply online at ssa.gov up to 4 months before you want benefits to start
  • You'll need: birth certificate, W-2s or tax return, bank info for direct deposit
  • Benefits are taxable if combined income exceeds certain thresholds
  • You can change your mind within 12 months (repay benefits and restart later)

✓ Your Action

If claiming now, apply at ssa.gov. If delaying, mark your calendar for when you plan to claim. Review strategy with your spouse if applicable.

🌿 Sign up for a my Social Security account even if you're not claiming yet. Verify your earnings history and track projected benefits.

4

⚖️ Rebalance to Your Retirement Allocation

Your portfolio's job has changed

Your asset allocation in retirement should balance three needs: current income, growth for longevity, and protection against sequence risk.

  • Traditional: 60% stocks / 40% bonds, or more conservative
  • Bucket Strategy: 1-2 years cash, 3-7 years bonds, remainder in stocks
  • Rising Equity Glidepath: Start conservative, gradually increase stocks over time

✓ Your Action

Review your current allocation across all accounts. Rebalance to your target retirement allocation. Ensure adequate cash reserves.

5

📝 Understand Required Minimum Distributions

Avoid the 25% penalty for missed RMDs

Once you reach age 73 (as of 2023), you must start taking Required Minimum Distributions from traditional 401(k)s and IRAs. Roth IRAs have no RMDs during your lifetime.

  • When: First RMD by April 1 of the year after you turn 73
  • How much: Based on account balance and IRS life expectancy tables
  • Tax impact: RMDs are taxable income—plan accordingly
  • QCD strategy: Qualified Charitable Distributions can satisfy RMDs tax-free

✓ Your Action

If 73+, calculate your RMD and set up a withdrawal plan. Consider Roth conversions before RMDs begin. Explore QCDs if you donate to charity.

6

🌟 Design Your Retirement Lifestyle

Create a fulfilling life with purpose and connection

The financial mechanics are important, but the happiest retirees are those who've thoughtfully designed how they'll spend their time.

  • Purpose: What will give your days meaning? Volunteering, mentoring, creative pursuits?
  • Connection: How will you maintain social bonds outside of work?
  • Structure: Some structure helps—what routines will you create?
  • Health: Physical and mental health are your most valuable assets
  • Legacy: What do you want to pass on—financially and otherwise?

✓ Your Action

Envision your ideal retirement. What does a perfect week look like? Start building the habits, connections, and activities that will make retirement fulfilling.

🌿 Consider a "practice retirement" before fully retiring—take an extended leave if possible to test your plans and assumptions.

Essential Reading

Deep dives into the topics that matter most in retirement.

01
Withdrawal Strategy

The 4% Rule: What It Gets Right and Wrong

Understanding the most famous retirement rule—and when to break it.

8 min
02
Social Security

When to Claim Social Security: A Framework

The decision that could mean $100,000+ difference in lifetime benefits.

10 min
03
Healthcare

Medicare Explained: Parts A, B, C, D, and Medigap

A clear guide to navigating the alphabet soup of Medicare.

12 min
04
Tax Planning

Roth Conversions in Retirement: The Tax Arbitrage Opportunity

How the "gap years" between retirement and RMDs create a tax planning window.

9 min
05
Longevity

Sequence of Returns Risk: The Retirement Danger You Must Understand

Why when matters as much as how much in early retirement.

7 min

Tools for Your Journey

Our top picks for managing retirement finances.

🎯

Boldin

Retirement Planning

Comprehensive retirement projections with withdrawal strategy modeling.

  • Withdrawal planning
  • Tax optimization
  • Scenario modeling
Start Planning →
📊

Empower

Net Worth Tracking

Free dashboard to track all accounts and monitor spending in retirement.

  • 100% free
  • Retirement planner
  • Fee analyzer
Track Net Worth →
🏥

Medicare.gov

Healthcare

Official Medicare plan finder to compare options in your area.

  • Plan comparison
  • Drug coverage check
  • Cost estimates
Compare Plans →
📈

Vanguard

Low-Cost Investing

The gold standard for low-cost index funds and retirement accounts.

  • Lowest expense ratios
  • Investor-owned
  • Excellent service
Open Account →

Disclosure: Some links are affiliate links. We may earn a commission at no extra cost to you. We only recommend products we genuinely believe in.

Essential Reading

Books that will shape how you think about retirement.

📘

Die With Zero

by Bill Perkins

Optimize your life, not just your wealth. A provocative look at spending down meaningfully.

View on Amazon →
📗

The Bogleheads' Guide to Retirement Planning

by Taylor Larimore et al.

Comprehensive guide covering tax strategies, asset allocation, and withdrawal planning.

View on Amazon →
📙

How Much Can I Spend in Retirement?

by Wade Pfau

Academic rigor meets practical advice on sustainable withdrawal rates.

View on Amazon →
📕

Your Money or Your Life

by Vicki Robin

Transform your relationship with money and align spending with your values.

View on Amazon →
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