You spent thirty or forty years saving for retirement. You did the work. So why do so many people get blindsided in the first few years of it?
Michael Euston and Jamie Olson counted down the five retirement surprises that come up most often in client conversations. None of them are exotic. All of them are plannable. And the number one surprise is probably not the one you are expecting.
5. Your Tax Bill May Not Shrink
The common assumption is that when the paycheck stops, the tax rate drops. That is not what we see.
Required minimum distributions from IRAs and other retirement accounts kick in during your seventies. Social Security turns on. Some people pick up part-time or consulting work. Add it together and it is not unusual for a household to report more taxable income in retirement than during their working years.
Medicare adds another layer. IRMAA, the income-related monthly adjustment amount, uses a two-year lookback on your income to set your Medicare premiums. Cross a threshold and your premium can rise by several hundred dollars a month. Most people find out after the fact.
The longer your runway, the more you can do about it. Roth conversions before Social Security starts, coordinating which accounts you draw from, and managing income against specific thresholds are all easier to execute when you are planning years ahead rather than reacting in April.
4. Health Care Costs Before Medicare
Retiring early sounds great until you price the gap. If you stop working at 60, you are covering your own health care for five years before Medicare eligibility at 65. On the exchange, or through an alternative like a health share program, that can run into the tens of thousands of dollars a year for a couple or a family.
The bigger issue is the trajectory. Health care costs have historically inflated faster than the broad consumer price index. When Heirloom builds a financial plan, we assume a compounding health care inflation rate above 5%. The only category we model higher is higher education. And that is before you get to long-term care, which is its own planning conversation.
A plan that uses general inflation for health care is understating the number.
3. Adult Children Moving Back Home
Most of the people we work with want to help their kids get started. That is a goal, not a problem. The surprise is how rarely it gets quantified.
Thrivent's fifth annual Boomerang Kids Survey, fielded by Ipsos in the spring of 2026 among 2,325 US adults, found that 44% of parents with adult children ages 18 to 35 have had a child move back home at some point. Among current boomerang parents, 47% say some area of their finances has been affected. Forty-three percent said they would cut their own spending to support an adult child, and nearly one in five said they would reduce their retirement savings to do it.
Reducing retirement contributions to help a kid is a real decision with real math behind it. It should be a decision, not a drift. Putting a dollar figure on what you want to give, and testing it against your own retirement goals, is what lets you be generous on purpose.
2. Purpose After Work
Retirement research keeps landing on the same point: you want to retire to something, not just from something.
Work provides more than income. It provides structure, colleagues, and a reason to be somewhere. When that disappears and nothing replaces it, quality of life tends to follow. When we ask pre-retirees what they plan to do and the answer is golf and sleeping in, we push harder. Roughly six weeks in, golf stops being the answer.
You are done working. You are not done contributing. Figuring out where the contribution comes from is part of the plan, and the people who do that work ahead of time tend to enjoy retirement more.
1. Spending Too Little
This is the one that comes up most, and it is the same number one we land on in a lot of our Top 5 conversations.
People who save diligently for forty years are very good at saving. Then we ask them to spend down the assets they spent a career accumulating, and it is genuinely uncomfortable. So they underspend. They skip the trip. They are less generous than they could afford to be.
There are two failure modes in retirement. One is running out of money. Everybody worries about that one. The other is reaching the end of the plan with unused capacity and a list of things you did not do while you were healthy enough to do them. Almost nobody plans for that one.
The fix is not a pep talk. It is math. When you can see every year of your retirement laid out, cash flows and all, you stop guessing. That is what gives lifelong savers permission to actually spend.
The Common Thread
Every one of these connects to the others. Health care costs, helping your kids, and the tax bill all shape how much you can comfortably spend. Which is exactly why we build a plan that maps every year rather than working from rules of thumb.
At Heirloom, wealth and tax sit under one roof, so both sides of the equation get planned together. If you are within ten years of retirement, or already in it, these five are worth a conversation.
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