Let's say you're nearing retirement with about $1 million saved. Nice work. You've been disciplined, avoided the flashy stuff, and stuck with advice that emphasizes simplicity and safety.
That sounds exactly like what you're supposed to do. But here's the thing: retirement taxes don't reward good intentions. They respond to structure. And some of the most "responsible" moves people make in their late 50s and early 60s can reshape their tax situation in ways that are surprisingly hard to undo later.
The expensive decision is often no decision at all
The biggest tax blunders in retirement usually aren't aggressive gambles. They're the result of inertia.
Take defaulting to traditional retirement accounts without thinking through a long-term withdrawal strategy. Traditional IRAs and 401(k)s give you that nice tax deferral upfront, but every dollar you pull out later gets taxed as ordinary income. Over time, that income stacks on top of Social Security benefits and can shove you into higher tax brackets than you ever anticipated.
Another classic mistake is dodging Roth conversions because they generate a tax bill today. In reality, skipping conversions during years when your income is lower can mean paying much steeper taxes down the road, especially once required minimum distributions start. At that point, the IRS tells you exactly how much you have to withdraw, whether you actually need the cash or not.
Then there's the timing issue. Lots of retirees assume their taxes will naturally drop once they stop working. But the opposite often happens. Pension income, Social Security, and mandatory withdrawals compress your income into a tighter window, which means a bigger chunk disappears to taxes over the decades ahead.
Two paths, very different outcomes
Path one: Keep everything simple. Stick with traditional accounts, minimize changes, and worry about taxes when you start taking withdrawals. This approach feels safe because it avoids immediate pain, but it leaves you with less control once retirement income starts flowing.
Path two: Build in flexibility. Actively manage which account types you use, the order you withdraw from, and when you do conversions to spread your tax burden more evenly. This requires more thinking upfront, but it preserves your options and can meaningfully reduce what you pay in taxes over your lifetime.




