The fruit is ripening. This is the time to protect what you've cultivated while preparing for the transition ahead. Strategic moves now can add years of security to your retirement.
Follow these 7 steps to prepare for the transition ahead. Click any step to expand.
Know your number and whether you're on track
In your 50s and 60s, retirement planning moves from abstract to concrete. You need detailed projections that account for Social Security timing, healthcare costs, inflation, sequence of returns risk, and your desired lifestyle.
Your projections should answer: When can you afford to retire? How much can you safely spend each year? What's the optimal Social Security claiming strategy? How do different scenarios affect your plan?
✓ Your Action
Run comprehensive retirement projections using a quality planning tool. Test multiple scenarios and understand your range of outcomes.
🌿 The map is not the territory, but a good map helps you find your way. Model often, adjust wisely, and trust the journey.
A decision worth $100,000+ over your lifetime
Social Security is likely one of your largest retirement "assets." Claiming at 62 vs. 70 can mean a 77% difference in monthly benefits for life. For each year you delay past full retirement age, benefits increase by 8%.
Key factors: Break-even analysis, spousal coordination (who claims when?), health and longevity expectations, other income sources, and survivor benefit implications.
✓ Your Action
Create a my Social Security account to see your projected benefits. Use a planning tool to model different claiming ages and spousal strategies.
🌿 Patience is a virtue that pays 8% per year. Consider whether waiting brings more peace than claiming early.
The largest and most unpredictable retirement expense
If you retire before 65, you'll need to bridge the gap to Medicare. Even after Medicare, you'll have premiums, deductibles, and costs for things Medicare doesn't cover.
Before 65: COBRA, ACA marketplace, spouse's plan, or part-time work with benefits. At 65: Choose between Original Medicare + Medigap or Medicare Advantage. Don't forget: Part D prescription coverage and long-term care planning.
✓ Your Action
Estimate healthcare costs at different ages. If retiring before 65, research your bridge options. Start learning about Medicare well before you turn 65.
🌿 Your initial Medicare enrollment is 7 months centered around your 65th birthday. Mark your calendar. Missing it creates lasting penalties.
Extra contribution room after age 50
After 50, you can contribute extra to retirement accounts. For 2026: 401(k) catch-up is $8,000 (total $32,500 if 50+), IRA catch-up is $1,100 (total $8,600 if 50+), and HSA catch-up is $1,000 if 55+.
If you can max these out for your final 10-15 working years, that's potentially $300,000+ in additional tax-advantaged savings.
✓ Your Action
Review your current contribution rates. If not maxing out, calculate what you can afford to increase. Every extra dollar compounds tax-advantaged.
🌿 These extra contributions are a gift. Use them wisely in the final stretch before the harvest.
Protect against sequence of returns risk
A bear market early in retirement is far more damaging than one 20 years out. This "sequence of returns risk" means your portfolio's job changes from pure growth to providing reliable income while still growing.
Key shifts: Gradually reduce stock allocation (but don't go to zero), build a cash buffer of 1-2 years of expenses, consider a "bucket strategy," and review bond duration and quality.
✓ Your Action
Review your current asset allocation across all accounts. Develop a glide path to your target retirement allocation over the next several years.
🌿 The wise gardener protects the harvest from storms. Build your shelter before you need it.
Pay taxes now at lower rates for tax-free withdrawals later
If you have significant money in traditional 401(k)s and IRAs, you'll owe taxes on every withdrawal. Roth conversions let you pay taxes now to enjoy tax-free withdrawals later.
Best candidates: Years with lower-than-usual income, large traditional balances facing RMDs, those expecting higher future tax rates, and those wanting to leave tax-free inheritance. The "conversion window" between retirement and Social Security/RMDs is often optimal.
✓ Your Action
Model the tax impact of Roth conversions in different years. Consider a multi-year strategy rather than converting everything at once.
🌿 Consider the tax seasons ahead. Sometimes paying a smaller harvest tax now yields a greater bounty later.
Protect your family and ensure your wishes are followed
Now is the time to create or update your estate documents. Laws change, circumstances change, and documents more than 5 years old should be reviewed.
Critical documents: Will, revocable living trust (avoids probate), durable power of attorney, healthcare proxy/living will, and beneficiary designations on all accounts (these override your will).
✓ Your Action
If you don't have estate documents, create them with an estate attorney. If you do, schedule a review. Update all beneficiary designations.
🌿 The greatest gift you can leave is clarity. Make your wishes known, and spare your loved ones difficult decisions.
Deeper dives into topics that matter at this stage of life.
A comprehensive analysis of Social Security claiming strategies and how to maximize your lifetime benefits.
Options for healthcare coverage if you retire before Medicare eligibility and how to budget for this critical expense.
How maximizing catch-up contributions from 50-65 can add hundreds of thousands to your retirement.
Why the order of investment returns matters more than average returns as you approach retirement.
Our top picks for navigating the transition to retirement.
Retirement Planning
Comprehensive retirement planning with Social Security optimization and Roth conversion modeling.
Net Worth & Analysis
Free dashboard to track all accounts with retirement planning and fee analysis.
Social Security
Official SSA portal to view your earnings history and benefit estimates.
Investing
Low-cost index funds and target-date funds for retirement investing.
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Books to guide your transition to retirement.
Practical frameworks for determining your retirement number and building a sustainable withdrawal strategy.
View on Amazon →Rethinking retirement beyond finances. Finding purpose, meaning, and fulfillment in life's next chapter.
View on Amazon →The definitive guide to navigating the complexities of Social Security claiming strategies.
View on Amazon →Transform your relationship with money and align spending with your values.
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