Keith Hensley, CFP® | March 12, 2025
Retirement is something you’ve been working towards for decades, but now that it’s here, pulling the trigger feels... intimidating. One minute, you're dreaming of lazy beach days and golf rounds; the next, you're sweating over spreadsheets wondering, “Will my money last?”
Take a deep breath. Let’s tackle the biggest financial concerns folks face when stepping into retirement—and some tips to help you feel confident in your decisions.
Where’s My Paycheck Coming From?
For years, you’ve relied on your employer depositing a paycheck into your account like clockwork. Now, it’s up to you to replace that income. What might those sources be:
Social Security – Reliable, but probably not enough for all your needs (or golf habit).
Pensions – A rare commodity these days. If you’ve got one, congrats! But is it enough?
Savings & Investments – This is where smart withdrawals matter. More on that later.
Helpful Tips:
🟢 Map out your income sources. Make a list of how much will come from Social Security, pensions, and investments each month.
🟢 Create a withdrawal strategy. A mix of cash flow, dividends, and a dynamic withdrawal plan can help.
🟢 Build an emergency bucket. Keep six months to a years' worth of expenses in a liquid account to avoid selling investments at a bad time.
Will I Run Out of Money?
This is the big fear, and rightfully so. Here’s what could impact your nest egg:
Living too long – A good problem to have, but your money needs to keep up.
Inflation – The sneaky thief that makes everything more expensive.
Sequence of Returns Risk – Fancy term for “bad market timing can hurt your withdrawals.”
Spending too fast – Tempted to buy that dream beach condo? Make sure it fits the plan first.
Helpful Tips:
🟢 Run projections. Use a retirement calculator or work with a planner to see how long your money will last.
🟢 Adjust spending as needed. Consider a dynamic withdrawal strategy—spend less when markets are down.
🟢 Annuities could be an option. Some people like them for guaranteed income, but they aren’t for everyone.
What About Healthcare Costs?
Healthcare in retirement can be a budget buster. Here’s what to plan for:
Medicare gaps – Original Medicare doesn’t cover everything. Supplemental plans may be needed.
Long-term care – Assisted living and nursing homes are not cheap. Have a plan.
Unexpected medical expenses – Because life likes to throw curveballs.
Helpful Tips:
🟢 Compare Medicare plans. Traditional Medicare + Medigap vs. Medicare Advantage—pick what suits your health needs.
🟢 Look into long-term care insurance. It’s best to consider it in your 50s or early 60s while it’s still affordable. Self-insure, relying on your investment portfolio later in life - plan accordingly.
🟢 Set aside a healthcare fund. HSAs (if available before retirement) or other savings can help cover costs.
Am I Being Tax-Efficient?
Taxes don’t retire just because you do. Managing withdrawals wisely can save you big money:
Which accounts to pull from first? (Taxable? Tax-deferred? Roth?)
Social Security taxation – Yes, Uncle Sam still wants a cut.
Required Minimum Distributions (RMDs) – You can’t keep that IRA money forever.
Helpful Tips:
🟢 Consider Roth conversions. Converting some traditional IRA funds before social security and RMDs can lower taxes later.
🟢 Withdraw in a tax-efficient order. Usually: taxable accounts first, tax-deferred next, and Roth last. *everyone's situation is unique though*
🟢 Plan for tax brackets. Avoid jumping into a higher bracket by spreading withdrawals strategically.
When Should I Take Social Security?
This is a million-dollar question (literally, over time). Factors to consider:
Early (62)? More years of checks, but smaller amounts.
Full Retirement Age (66-67)? A balanced choice.
Wait until 70? Maximize those monthly benefits, but can you afford to wait?
Spousal benefits? Strategies can help couples optimize income.
Helpful Tips:
🟢 Use an SSA calculator. Check your estimated benefits at different ages.
🟢 Consider your health and longevity. If your family lives long, delaying might pay off.
🟢 Factor in spousal benefits. One spouse waiting longer can help maximize income.
Final Thoughts
Yes, retirement is a major life change. And yes, financial worries are totally normal and frankly healthy. But with a solid plan in place, you can turn those cold feet into a confident retirement you’ve always dreamed of.
My advice, find a fee-only financial advisor that fits your needs and lean on them to help guide you through these decisions!
Keith Hensley | Founder of Florida Financial Planning, a fee-only, advice-only fiduciary firm based in Orlando, FL, serving clients nationwide through virtual meetings. As a CERTIFIED FINANCIAL PLANNER™ professional, Keith tackles your most pressing questions with expert, conflict-free guidance and a transparent flat-fee model.
Schedule Complimentary Introduction Meeting