It’s Here, Now What? What To Do 6 Months Before & After Retirement

You’ve spent decades building toward the retirement date circled on your calendar. At this point, you can almost taste the freedom (and the celebratory champagne). But as that date gets closer, you might find yourself asking: Am I really ready for this?

If there’s a little side of panic being served with your excitement, you’re not alone. Retirement isn’t just stepping away from work. It’s stepping into an entirely new way of living. Your paycheck changes. Your daily routine disappears. Even your sense of identity might wobble a bit.

The good news is, this transition doesn’t have to feel like a leap into the unknown. With some thoughtful financial moves in the months just before and after retirement, you can step confidently into your next chapter.

The Retirement Moment: Why This Window Matters

The six months before and after retirement act as a bridge between two very different worlds. On one side are the decades you have spent working, saving, and accumulating. On the other side is your new life of spending, distributing, and designing the life you actually want.

Two major shifts are happening at once during this time: 

The Financial Shift
The steady paycheck is gone. Instead, you’re coordinating withdrawals from multiple accounts. Your taxes look different. Your insurance needs evolve. It’s not about building wealth anymore. Now, it’s about managing and protecting it.

The Psychological Shift
You’re leaving behind the structure, the deadlines, and the daily interactions with colleagues. That can feel disorienting, even if you’ve been counting down the days. Many retirees describe the early months as “purpose whiplash.”

Taking meaningful action during this time can reduce your stress, add clarity, and set you up for a retirement that feels secure and purposeful.

7 Financial Moves To Make 6 Months Before & After Retirement

Here are seven practical steps you can take during this important window of time that will help your transition to retirement go more smoothly. 

1) Know Where Your Money Is Coming From

It may sound obvious, but plenty of people enter retirement without a clear income plan. Which accounts will you tap first? Taxable brokerage? IRA? Roth? 

The order matters more than you may have realized. When you get it right, you’ll keep more money in your pocket and less in Uncle Sam’s. 

Your retirement withdrawal strategy will depend on factors like:

• Current and future tax rates
  
• Whether you want to leave an inheritance
  
• Charitable giving goals
  
• Your actual spending needs

2) Secure a HELOC While You Qualify

One change many people don’t consider is that once your W-2 income stops, qualifying for credit becomes much harder. Even if you have substantial assets, lenders get nervous about retirement income.

Consider securing a HELOC (Home Equity Line of Credit) while you still have that steady paycheck. Even if you don’t think you’ll use it, think of it like a spare tire. You may never need it, but if you hit a bump, you’ll be glad it’s there.

3) File SSA-44 to Appeal IRMAA

Medicare premiums are based on your income from two years ago. When your income drops suddenly due to retirement, you may qualify to appeal those higher premiums using Form SSA-44. 

If you think you have a valid chance of lowering your premiums, you can always give this option a try. If everything you put on that form is correct, the worst they can do is not approve the appeal. 

Even if you’re not sure exactly how your income will shake out in your first year of retirement, you can start by paying the higher premiums and file the appeal later. If the Social Security Administration approves your adjustment, they’ll credit you retroactively for the overpayment.

4) Have a Healthcare Plan in Place If You Retire Early

If you’re retiring before 65, you’ll need to bridge the gap until Medicare. Options usually include COBRA, an ACA marketplace plan, or your spouse’s employer coverage.

Once you hit 65, you should enroll in Medicare as soon as possible. The timing is critical here, so set yourself up with several reminders leading up to your 65th birthday. 

Pro tip: Stop contributing to your HSA at least six months before you start Medicare or Social Security. Medicare coverage is retroactive, and extra HSA contributions in that window can trigger penalties.

5) Take Advantage of Roth Conversion Opportunities

Your income will likely be lower during the early years of retirement, which creates a perfect window for Roth conversions. By shifting some funds from tax-deferred accounts to tax-free Roth accounts, you reduce future Required Minimum Distributions and create more tax flexibility down the road.

This strategy works especially well if you retire before you start taking Social Security, creating a gap of lower-income years where conversions can be done at reduced tax rates.

6) Update Your Estate Plan and Beneficiaries

Your life has changed significantly, so your estate plan should reflect that. Review your will, power of attorney, healthcare proxy, and especially your beneficiary designations on all accounts.

Make sure these choices align with your new withdrawal strategy and any changes in your family dynamics. 

7) Align Your Spending Plan With Your Values

Take time to map out your expenses in three categories: 

• Essential (housing, healthcare, basic living costs)
• Discretionary (dining out, hobbies, regular travel)
• Aspirational (dream trips, major home projects, generous gifts to family)

Make sure your spending reflects what matters most to you. This is your chance to design a lifestyle that aligns with your values, not just your budget.

Quick Q&A

As financial advisors, we commonly get asked , “What’s the single most important thing to get right before the paycheck stops?”

Our answer: 

• Get your cash flow plan nailed down. Know exactly how much you’ll need each month and where every dollar is coming from.
• Automate those transfers whenever possible. 
• Test your plan with a “practice month.” Live as if you’re retired while you’re still working. If you think you need $10,000 to cover expenses, set aside that amount in a separate account and live off it for a month.

Your Next Chapter Starts Here

Retirement isn’t the end of your story. Rather, it’s the start of a new and exciting chapter. The right plan will help you focus less on what you’re leaving behind and more on what you’re building toward.

At SK Wealth, we’ve helped clients navigate this transition for 25 years through our Integrated Financial Advantage™ process. We’ll help you align your financial strategy with your vision for retirement so you can live intentionally for many years to come.

If you’re standing at the edge of retirement and want guidance tailored to your life, we’re here to help you step across that bridge with clarity and confidence.