Jim and Carol felt they were doing everything right.
Jim was 63. Carol had just turned 61. They had been married for three years after both losing their spouses earlier in life. Retirement was finally on the horizon, and with their savings, pensions, Social Security, and investment accounts, they believed they had accumulated enough to stop working next year.
For more than a decade, they had faithfully worked with a well-known investment firm. Their portfolio had grown nicely. They met periodically with their advisor. Everything seemed to be in order.
Still, something didn’t feel settled.
“We think we’re okay,” Jim told us during our first meeting. “We just want someone to make sure we’re not missing anything.”
Honestly, I expected we’d simply confirm what their previous advisor had already done.
Instead, we found several important conversations that had never happened.
None of them involved picking better investments.
As retirement approaches, the biggest risks often have less to do with investment returns and more to do with planning decisions.
The most important questions are often not about which fund performed best last quarter. They are about whether the pieces of your financial life have been tested together.
Here are five areas we frequently find have either never been discussed or have simply been assumed.
One of the biggest mistakes we see is assuming retirement spending.
Many people estimate they’ll spend 70% or 80% of their current income because they’ve heard that rule somewhere. Others simply guess.
The problem is that retirement spending isn’t a percentage. It’s a lifestyle.
For many healthy retirees, the early years of retirement are often the most expensive. Travel, hobbies, helping children, home renovations, and simply having more free time often increase spending before it eventually declines later in life.
Rather than guessing, your advisor should help you develop a concrete retirement spending plan based on how you want to live.
Jim and Carol updated their
On paper, everything looked complete.
But when we modeled what would happen if Jim died first, we discovered something concerning.
Because both wanted their respective children to ultimately inherit their assets, the trust language unintentionally left the surviving spouse with significantly fewer financial resources than either had expected.
The legal documents weren’t necessarily wrong.
They simply hadn’t been tested against real-world financial outcomes.
A retirement plan shouldn’t stop at asking, “Do you have a will?”
It should answer, “What happens financially if that will is used tomorrow?”
Most retirement projections include inflation.
Many include taxes.
Surprisingly few include
Healthcare spending rarely follows a straight line. Some retirees have very few expenses for years, while others face surgeries, medications, or chronic conditions that significantly alter their financial picture.
Fidelity’s 2025 Retiree Health Care Cost Estimate projects that a 65-year-old retiring in 2025 may need $172,500 in after-tax savings to cover healthcare expenses in retirement.
Ignoring those possibilities doesn’t make them disappear.
A good retirement plan prepares for them.
Long-term care is one of the largest financial risks many retirees face.
According to Vanguard, about 14% of adults will need at least two years of paid long-term care, while another 6% will need five years or more.
That doesn’t automatically mean everyone needs long-term care insurance.
But it does mean everyone needs a strategy.
Will you self-insure?
Purchase insurance?
Use hybrid life insurance?
Rely on family?
There isn’t one right answer. But “we haven’t talked about it” isn’t a strategy.
Even financially successful retirees often enter retirement with mortgages, HELOCs, investment loans, or other debt.
Should those debts be paid off?
Refinanced?
Kept because the interest rate is attractive?
The answer depends on cash flow, taxes, investment assets, and retirement income — not just the interest rate.
Yet many retirement lans never address debt at all.
Investment management matters. But as retirement gets closer, it should not be the only topic of conversation.
| Investment Management May Ask | Retirement Planning Should Also Ask |
| How is your portfolio performing? | How much will your retirement lifestyle actually cost? |
| Are you allocated appropriately? | Where will retirement income come from, and in what order? |
| Are you taking enough risk? | What happens if one spouse dies earlier than expected? |
| Are fees and performance being reviewed? | How will healthcare and long-term care costs be handled? |
| Should the portfolio be rebalanced? | How do debt, taxes, estate planning, insurance, and investments fit together? |
Jim and Carol didn’t leave their previous advisor because of poor investment performance.
Their investments were fine.
They came seeking a clearer understanding of how the pieces fit together.
They wanted someone to connect every piece of their financial life — income, taxes, healthcare, estate planning, debt, insurance, and investments — into a single, coordinated retirement strategy.
That’s what comprehensive financial planning should do.
If your advisor reviews your portfolio only once or twice a year, you’re likely receiving investment management.
As retirement approaches, the discussion needs to be about more than “How are our investments doing?”
The better question is: “Have we looked at the planning decisions that could shape our retirement?”
As retirement approaches, it may be time to look beyond investment performance and ask whether your income, taxes, estate planning, healthcare, insurance, debt, and investments are working together.
At Spaugh Dameron Tenny, we help successful individuals and families navigate the planning decisions that can shape retirement. If you are approaching retirement and want a more coordinated view of your financial life, we invite you to start a conversation.
Investment management focuses primarily on how assets are invested, allocated, and monitored. Retirement planning looks more broadly at income, spending, taxes, healthcare, estate planning, debt, and insurance, and how those areas work together.
A good sign is that your advisor helps you answer questions beyond portfolio performance, such as how much retirement may cost, where income will come from, how taxes may affect withdrawals, and what happens if one spouse dies or needs care.
Yes. Healthcare and long-term care can significantly affect retirement spending. They need not dominate the plan, but they should be part of the conversation.
Not necessarily. Investment performance matters, but retirement also depends on spending, income timing, taxes, healthcare costs, estate planning, debt, and risk management.
This material is provided for general informational and educational purposes only and is not intended to provide individualized investment, tax, or legal advice. The information discussed may not be applicable to all individuals or situations.
The client scenario presented is hypothetical and provided for illustrative purposes only. It does not represent an actual client experience or guarantee future results.
CRN202907-11606822
Shane Tenny, CFP®, is Managing Partner of Spaugh Dameron Tenny, where he helps high-net-worth individuals and families navigate complex financial decisions with clarity, structure, and confidence. Since joining the firm in 2000, Shane has worked with clients through major financial transitions, including career changes, liquidity events, retirement, and multigenerational planning. His approach combines comprehensive financial planning with a focus on behavioral finance, including advanced studies in Behavioral Economics through the University of Chicago Booth School of Business. Shane is the author of Your Next Million, former host of the Prosperous Doc® Podcast, and a nationally recognized financial advisor, speaker, and educator.
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