5 Retirement Planning Mistakes I See in Initial Meetings

By Roger Bair, MSF, CFP®, CIMA®

“Can I actually retire?” It’s the question that keeps people up at night, even those with millions in the bank. You’ve built something valuable through hard work, and you don’t want to mess it up now. 

When we sit down for a Financial Physical®, we often find that the biggest risks to a comfortable retirement have nothing to do with how the S&P 500 performed last week. Instead, the risks live in outdated estate plans, misunderstood spending habits, and tax strategies that are stuck in the past. 

Here are five of the most common retirement planning mistakes I see in initial meetings, and how we help you look at your full financial picture before you make the leap.

Mistake 1: Their Advisor and CPA Aren’t Talking

One of the most common retirement planning mistakes isn’t related to investments at all—it comes down to coordination.

We often meet individuals who have:

• A financial advisor managing investments
• A CPA preparing tax returns

But those two professionals rarely, if ever, communicate.

In practice, that usually means tax planning isn’t really happening. The CPA is focused on reporting what already occurred, not helping shape what should happen next.

For example, someone might:

• Withdraw from the wrong accounts in retirement, increasing taxes.
• Miss opportunities for Roth conversions during lower-income years.
• Overlook strategies for managing capital gains or required minimum distributions.

When tax planning and investment decisions are disconnected, the results tend to be less efficient.

Mistake 2: Their Portfolio Looks the Same as It Did at Age 40

Another pattern we see is portfolios that haven’t evolved as retirement gets closer.

At age 40, a more growth-oriented allocation often makes sense. There’s time to recover from market downturns.

But the five years before and after retirement are different.

This period is particularly sensitive to what’s known as sequence-of-return risk—the order in which market returns occur.

Here’s a simplified example:

• Two retirees have the same average return over time.
• One experiences a market decline early in retirement.
• The other experiences it later.

The one who faces losses early, while also withdrawing income, may see a much different long-term outcome.

Mistake 3: Relying on a Rule of Thumb Instead of a Specific Plan

“I think we need about $1.5 million to retire.”

We hear versions of this often. The number may come from an article, a colleague, or a rough estimate.

The challenge is that a number by itself doesn’t answer the real question: 

How does that translate into income over time?

Two households with the same savings can have very different outcomes depending on:

• Spending patterns
• Tax exposure
• Investment structure
• Longevity

For example:

• One couple may comfortably retire with $1.5 million.
• Another may need significantly more due to higher spending or healthcare costs.

Having a target is helpful, but it needs context.

Mistake 4: Not Knowing What They Actually Spend

This is one of the most revealing retirement planning mistakes, and it usually shows up in a simple statement:

“We spend about $10,000 a month… I think.”

That uncertainty makes it difficult to answer almost every other planning question.

If spending isn’t clearly understood:

• Retirement income projections become less reliable.
• It’s harder to evaluate whether savings are on track.
• Decisions about timing become less grounded.

In one case, a couple estimated their monthly spending at $9,000. After reviewing their accounts, the actual number was closer to $12,500.

This scenario doesn’t require perfect tracking, but it does require a reasonable level of awareness.

Mistake 5: No Clear Vision Beyond “Not Working”

Finally, many people approach retirement with a financial plan, but no clear picture of how they’ll spend their time or money.

“Not working” is a starting point, not a plan. A more detailed vision might include:

• Travel plans in the first 5–10 years
• Part-time work or consulting
• Supporting family members
• Charitable giving
• Changes in housing

Each of these has financial implications. For example:

• Increased travel early in retirement may require higher withdrawals up front.
• Downsizing a home could free up capital or reduce expenses.
• Part-time income may create opportunities for tax planning.

Without this context, it’s difficult to align financial decisions with real-life goals.

Identify Retirement-Planning Mistakes Now

Identifying retirement planning mistakes doesn’t mean something is wrong. Rather, it’s a way to test whether your current plan reflects how you actually live, spend, and make decisions.

If you’re approaching retirement, this is a good time to pressure-test your plan. A second set of eyes can often uncover issues you didn’t know to look for. This is exactly the type of question we walk through during Financial Consulate’s Financial Physical® which is a structured review designed to help you evaluate where things stand today and what adjustments may be worth considering.

For many people, the goal isn’t to start over, it’s to refine what they’ve already built and move into retirement with a clearer understanding of how everything fits together.

To get in touch with me or our team, call (410) 823-7283, or you can schedule a time to talk at your convenience through our website.

Frequently Asked Questions

What are the most common retirement planning mistakes?

Some of the most common retirement planning mistakes include lack of coordination between advisors, outdated investment strategies, unclear spending habits, and relying on general rules of thumb instead of a personalized plan. These gaps can lead to inefficiencies and missed opportunities over time. A great way to avoid these mistakes is to partner with a financial professional. The team at The Financial Consulate is here to help.

When should I start reviewing my retirement plan for potential mistakes? 

Ideally, you should begin reviewing your retirement plan at least 5–10 years before your expected retirement date. This window allows time to adjust your investment strategy, refine income planning, and address tax considerations before decisions become more time sensitive.

How can I avoid retirement planning mistakes as I get closer to retirement?

A structured, comprehensive approach can help you avoid retirement planning mistakes. This often includes coordinating tax and investment strategies, understanding your spending, and aligning your financial plan with your long-term goals. Working with a fee-only financial advisor can provide a second layer of review and help your plan reflect your full financial picture. If you’re looking for personalized guidance, reach out to us at The Financial Consulate. 

About Roger

Roger Bair, MSF, CFP®, CIMA®, is a Senior Wealth Advisor at The Financial Consulate with more than 30 years of experience guiding individuals and families through major financial transitions. He advises on tax, estate, investment, and retirement planning, with a particular focus on helping clients align their financial decisions with what matters most to them.