Ask people in their 60s what they wish they had done differently at 50 and the answers are rarely about picking the wrong fund. They are about taxes and timing: contributions they could have made, low-income years they let slip by, and paperwork that quietly decided where their money went. Fifty is the age when the tax code starts offering extra room, and the decade when the decisions that shape your retirement tax bill get locked in. Here are the moves we see people wish they had made.
This is general information, not individual tax advice — the right treatment depends on your specific situation.
1. Use the Catch-Up Contributions You Just Unlocked
At 50 the contribution limits go up. For 2026, a 401(k), 403(b) or governmental 457(b) allows $24,500 plus an $8,000 catch-up, and IRAs allow $7,500 plus a $1,100 catch-up. Under SECURE 2.0, workplace plans may also offer a larger “super catch-up” of $11,250 in the years you turn 60 through 63, if the plan allows it.
One new wrinkle starts in 2026: if your FICA wages from that employer topped $150,000 last year, your catch-up contributions must go in as Roth (after-tax). Business owners have even more room. A Solo 401(k) or SEP can shelter far more than an employee plan — see our guide to small-business retirement plans.
2. Plan the “Gap Years” Before Required Distributions
For most people turning 50 today, required minimum distributions (RMDs) start at age 75 (73 for those born 1951–1959). That leaves a window — often from retirement until RMDs and Social Security kick in — when taxable income can be unusually low. Those years are ideal for converting slices of a traditional IRA to a Roth at modest brackets, so future RMDs are smaller and the money grows tax-free.
The regret we hear most is letting that window close by accident. Mapping it out at 50 tells you how much to put in pre-tax versus Roth now, and which accounts to draw from first. Our article on tax-efficient retirement withdrawals walks through the order.
3. Treat Your HSA as a Retirement Health Fund
If you have a qualifying high-deductible health plan, a Health Savings Account is one of the most tax-favored accounts available: deductible going in, tax-free growth, and tax-free coming out for medical costs. For 2026 the limits are $4,400 (self-only) and $8,750 (family), plus a $1,000 catch-up from age 55. Paying today's medical bills out of pocket and letting the HSA grow builds a fund for retirement health costs. Note that you can't contribute once you are enrolled in Medicare. More in our HSA strategy guide.
4. Know What Health Coverage Costs Before 65
Retiring at 60 means five years before Medicare. For many early retirees, ACA marketplace coverage is the bridge, and its premium credits depend on income. With the subsidy cliff back for 2026, earning even $1 over 400% of the poverty line can wipe out the credit — so a large IRA withdrawal or Roth conversion in those years can be surprisingly expensive. See the ACA subsidy cliff for the planning moves that work.
5. Watch the Two-Year Medicare Lookback
Medicare Part B and Part D premiums rise for higher-income retirees through IRMAA surcharges, and they are based on your tax return from two years earlier. 2026 premiums use 2024 income; the first surcharge tier starts above $109,000 of modified AGI for single filers and $218,000 for joint filers, and each tier is a cliff. In practice, that means income at 63 sets your premiums at 65. Selling a business, a big capital gain or an oversized Roth conversion in those years deserves a projection first.
6. Update Your Beneficiary Designations
Retirement accounts and HSAs pass by the beneficiary form on file, not by your will. Forms naming an ex-spouse, a deceased parent or “my estate” are common and costly. Most non-spouse heirs must now empty an inherited IRA within 10 years, which can push them into higher brackets — so who you name, and which accounts go to whom, is a tax decision too. Our guides to the inherited IRA 10-year rule and estate and gift tax basics cover the details.
The One Move to Make This Year
Build a 10-year tax projection. Lay out expected income, the year you plan to stop working, when Social Security and RMDs begin, and the ACA and Medicare thresholds you need to respect. It turns every item above from a vague intention into a specific number for a specific year — how much to contribute, how much to convert, and when.
How VarStan Helps
We prepare multi-year tax projections for owners and families in their 50s and 60s, coordinate catch-up and Roth strategy with your business's retirement plan, and time conversions and large sales around the ACA and Medicare cliffs. If you are 50-something and want to know what your next ten years of taxes look like, start with a conversation.
Related reading: Deducting Startup Costs: What New Businesses Can Write Off and The Self-Employed Health Insurance Deduction Explained.