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You've reached the summit. Now navigate this new chapter with confidence—managing withdrawals, healthcare, and making your money last for decades to come.
Follow these 6 steps to navigate retirement with confidence. Click any step to expand.
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.
✓ 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.
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.
✓ 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.
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:
✓ 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.
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.
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.
✓ 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.
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.
✓ 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.
Deep dives into the topics that matter most in retirement.
Understanding the most famous retirement rule—and when to break it.
The decision that could mean $100,000+ difference in lifetime benefits.
A clear guide to navigating the alphabet soup of Medicare.
How the "gap years" between retirement and RMDs create a tax planning window.
Why when matters as much as how much in early retirement.
Our top picks for managing retirement finances.
Retirement Planning
Comprehensive retirement projections with withdrawal strategy modeling.
Net Worth Tracking
Free dashboard to track all accounts and monitor spending in retirement.
Healthcare
Official Medicare plan finder to compare options in your area.
Low-Cost Investing
The gold standard for low-cost index funds and retirement accounts.
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.
Books that will shape how you think about retirement.
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