Retirement Strategy Guide

The Biggest Mistakes People Make in Retirement Planning (And How to Avoid Them)

The most consequential retirement planning mistake is not a single bad decision. It is the absence of a coherent strategy before decisions are made. This guide covers eight of the most common errors professionals and executives make, and what a thoughtful planning process seeks to address at each step.

The Direct Answer

What Is the Biggest Mistake Most People Make Regarding Retirement?

The single most common retirement planning mistake is making major financial decisions, such as when to claim Social Security, when to retire, or how to draw from accounts, without a written, comprehensive strategy in place first. Without that foundation, each individual decision may seem reasonable but can work against the others in ways that are difficult to reverse. According to the Employee Benefit Research Institute, fewer than half of workers report having calculated how much they need to save for retirement. A strategy-first approach seeks to bring structure to those decisions before they are made, though outcomes always depend on individual circumstances.

Common Planning Errors

Mistakes 1 Through 4: Strategy and Income Decisions

The mistakes below tend to cluster around the most consequential decisions professionals face in the five to ten years before retirement. Each one is common, each one is avoidable, and each one is more manageable when addressed as part of a coordinated plan.

01

Claiming Social Security Without a Strategy

Social Security benefits can be claimed as early as age 62 or delayed up to age 70, with the monthly benefit increasing significantly for each year of delay. Many people claim early simply because the option is available, without modeling the long-term income implications for themselves or a surviving spouse. The difference between an early and a delayed claim can be substantial over a multi-decade retirement, and the decision cannot be reversed after the first 12 months.

What a Planning Process Seeks to Address

  • 1 Model break-even ages across multiple claiming scenarios
  • 2 Factor in spousal and survivor benefit implications
  • 3 Coordinate with other income sources to reduce tax exposure on benefits

Note: In Minnesota, Social Security benefits may be subject to state income tax for higher earners. See our Minnesota Retirement Tax Guide for details.

02

Ignoring the Tax Implications of Retirement Distributions

Traditional 401(k) and IRA withdrawals are taxed as ordinary income. For many professionals who have accumulated significant balances in pre-tax accounts, distributions in retirement can push them into higher federal tax brackets, trigger Medicare surcharges (IRMAA), and, in Minnesota, subject a larger portion of their Social Security benefits to state income tax. The order and timing of withdrawals from different account types has meaningful tax planning consequences that are often overlooked until distributions begin.

What a Planning Process Seeks to Address

  • 1 Map the tax character of every account (pre-tax, Roth, taxable)
  • 2 Identify Roth conversion opportunities before RMDs begin
  • 3 Sequence withdrawals to manage bracket exposure year by year

Minnesota taxes traditional 401(k) and IRA distributions at ordinary income rates, with no broad retirement income exclusion. Tax planning specific to MN is addressed in our state retirement tax guide.

03

Underestimating Healthcare Costs in Retirement

Healthcare is consistently one of the largest and least-planned expenses in retirement. Fidelity Investments estimates that a 65-year-old couple retiring today may need approximately $330,000 in after-tax savings to cover healthcare costs in retirement (as of 2024), and that figure does not include long-term care. Most employer health coverage ends at retirement, leaving a pre-Medicare coverage gap between early retirement and Medicare eligibility at age 65. That gap period can represent significant unplanned cost for professionals who retire before 65.

What a Planning Process Seeks to Address

  • 1 Identify and budget for the pre-Medicare coverage gap
  • 2 Evaluate long-term care risk and insurance options
  • 3 Factor Medicare Part B and D premium surcharges (IRMAA) into income planning
04

Failing to Plan for Sequence-of-Returns Risk

Sequence-of-returns risk is the danger that poor portfolio performance in the early years of retirement, combined with ongoing withdrawals, can permanently impair a portfolio even if long-term average returns recover. A portfolio that declines significantly in year one or two of distributions may not recover at the same rate as one where withdrawals have not yet begun. This risk is distinct from average return risk and is specific to the distribution phase, making it a unique challenge for retirees that does not apply in the same way during accumulation.

What a Planning Process Seeks to Address

  • 1 Structure a retirement income plan that reduces reliance on portfolio withdrawals in volatile markets
  • 2 Maintain appropriate cash reserves to avoid forced selling during downturns
  • 3 Coordinate multiple income sources to reduce early-retirement withdrawal pressure

By the Numbers

Why Retirement Planning Mistakes Are So Costly

62%

of Americans fear running out of money in retirement more than death, according to Allianz Life (as of 2023)

$330K

Estimated healthcare cost for a 65-year-old couple in retirement, per Fidelity Investments (as of 2024). Individual costs vary.

76%

of near-retirees do not have a written retirement income plan, according to the Alliance for Lifetime Income (as of 2023)

Common Planning Errors

Mistakes 5 Through 8: Plan Design and Local Factors

The second group of common mistakes tends to be structural, meaning they are embedded in how a retirement plan is built, or not built, rather than in a single decision. For professionals in Minnesota, some of these carry state-specific implications that a nationally focused plan may not account for.

05

Having No Written Retirement Plan

A retirement plan is not a single investment account or a savings target. It is a written, coordinated strategy that addresses income, spending, taxes, healthcare, estate, and contingencies in one place. Many professionals approach retirement with a general sense of readiness, a portfolio they have watched grow, a Social Security estimate, and a rough budget, but no documented comprehensive strategy that connects these elements. When one piece changes, whether that is a market downturn, a health event, or a tax law change, a plan that exists only in general terms cannot be stress-tested or updated. Ultimately, the goal is financial independence on your terms, and that requires a written framework to build toward.

What a Planning Process Seeks to Address

  • 1 Build a single, written strategy covering all financial dimensions
  • 2 Establish scenario plans for market, health, and life changes
  • 3 Review and update the plan at least annually with your advisor

At New Horizons Boutique Financial Services, every engagement begins with strategy development before any recommendations are made. Our approach is intentionally built for the long term, with quarterly reviews to adapt as circumstances change.

06

Overlooking Minnesota-Specific Retirement Rules

Many professionals in the Twin Cities metro area work with nationally focused planning resources that do not account for Minnesota's distinct retirement tax environment. Minnesota taxes Social Security benefits for higher-income earners, taxes traditional 401(k) and IRA distributions at ordinary income rates with no broad retirement income exclusion, and imposes an estate tax with a threshold of $3 million, which is significantly lower than the 2026 federal exemption of approximately $13.6 million. Professionals subject to public pension systems such as PERA or TRA should also understand the Rule of 90 eligibility and how pension income may be subtracted from Minnesota taxable income within applicable limits.

Key Minnesota-Specific Factors

  • 1 Social Security taxed at state level above income thresholds (approx. $105K single / $130K MFJ as of 2026)
  • 2 Minnesota estate tax threshold: $3 million (far below 2026 federal exemption)
  • 3 PERA/TRA Rule of 90: eligibility for unreduced pension at age + service years = 90

Full detail: Retirement Planning in Minnesota and Minnesota Taxes on Retirement Income.

07

Over-Relying on a Single Income Source

Relying on one primary source of retirement income, whether that is a pension, a 401(k), or Social Security alone, creates concentration risk in the income layer of a retirement plan. If that source is disrupted, reduced, or taxed more heavily than anticipated, there is no buffer. Retirement income strategies that seek to draw from multiple sources, such as pre-tax accounts, Roth accounts, taxable savings, and Social Security, may offer more flexibility to adapt to tax law changes, market conditions, or unexpected expenses. Outcomes, of course, depend on individual circumstances and market conditions.

What a Planning Process Seeks to Address

  • 1 Identify all available income sources and the tax character of each
  • 2 Design a withdrawal sequence that seeks to reduce tax exposure over time
  • 3 Build flexibility into the income plan to respond to life changes
08

Treating Retirement Planning as a One-Time Event

Retirement planning is not complete when you retire. Tax laws change. Healthcare costs shift. Portfolio values fluctuate. Family circumstances evolve. A plan built at age 58 and never revisited is unlikely to serve you well at 68 or 78. Many professionals make an initial plan, implement it, and then disengage from active management, assuming their original strategy remains optimal. Regular, structured quarterly reviews with an advisor are designed to catch what has changed before it becomes costly to correct.

What a Planning Process Seeks to Address

  • 1 Conduct quarterly reviews to adapt to changing circumstances
  • 2 Monitor tax law changes that may require plan adjustments
  • 3 Update beneficiary designations, estate documents, and insurance coverage over time

Planning Approach Comparison

Reactive vs. Strategy-First Retirement Planning

The table below illustrates the difference between a reactive approach, where decisions are made as circumstances arise, and a strategy-first approach, where a coordinated plan precedes any individual decision. Neither approach guarantees a specific outcome; individual results always depend on circumstances.

Planning Dimension Reactive Approach Strategy-First Approach
Social Security Timing Claim based on eligibility or immediate need Model break-even scenarios; coordinate with other income and tax strategy
Tax on Distributions Withdraw as needed; address tax at filing Map account types; sequence withdrawals; identify Roth conversion windows
Healthcare Planning Address coverage gap when it arrives Budget for pre-Medicare gap; evaluate long-term care risk proactively
Sequence-of-Returns Risk Unaddressed; market-dependent Structured income to reduce early-retirement withdrawal pressure
Minnesota Tax Rules Learned at tax filing; limited ability to adjust MN Social Security thresholds, estate tax, and PERA rules integrated from the start
Plan Maintenance Revisited only when a problem surfaces Quarterly structured reviews; updated for life and law changes
Written Plan General or informal Documented strategy covering income, tax, healthcare, estate, and contingencies

This table is illustrative only. A strategy-first approach does not guarantee any specific result. Individual circumstances vary.

Our Approach

Strategy Before Decisions. Always.

At New Horizons Boutique Financial Services, our team, including Lars Engman, MBA and Alec Engman, B.S. Economics, University of Minnesota, holds FINRA Series 65 and Series 66 registrations and works with executives and professionals approaching retirement throughout the Twin Cities metro, including Lake Elmo, Woodbury, Stillwater, Arden Hills, and surrounding communities.

Every engagement begins with a comprehensive strategy that covers income, taxes, healthcare, estate planning, and cash flow, before any product or account recommendation is made. We intentionally limit the number of clients we serve so that every relationship receives the time and attention a complex financial transition requires.

There are no templates. Every plan is built around your situation, your goals, and your timeline.

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What We Cover in Every Retirement Strategy

  • 1

    Retirement Income Planning

    When and from where you draw income, and in what order

  • 2

    Tax Optimization Planning

    Distribution sequencing, Roth conversion analysis, and Minnesota-specific tax considerations

  • 3

    Social Security Strategy

    Claiming timing modeled against your full income picture

  • 4

    Healthcare and Long-Term Care Planning

    Pre-Medicare gap, IRMAA exposure, and insurance risk evaluation

  • 5

    Estate and Legacy Coordination

    Beneficiary designations, Minnesota estate tax threshold, and wealth transfer

Frequently Asked Questions

Common Questions About Retirement Planning Mistakes

What is the single biggest mistake most people make regarding retirement?

The single biggest mistake is making major retirement decisions, such as when to claim Social Security, how to draw from accounts, or when to retire, without a comprehensive written strategy in place first. Without that foundation, individual decisions can seem reasonable while working against each other in ways that are difficult to reverse. A strategy-first approach seeks to bring structure to those decisions before they are made.

What is the 4% rule for retirement and is it still relevant?

The 4% rule is a general guideline suggesting that withdrawing approximately 4% of your portfolio annually in retirement may allow the portfolio to last 30 years, based on historical market data from a 1994 study by William Bengen. It remains a widely referenced starting point, but it has limitations: it does not account for individual tax situations, healthcare costs, variable spending patterns, or the specific sequence-of-returns risk a person faces. For Minnesota residents, state income tax on distributions can meaningfully affect net withdrawal amounts. The 4% rule is best used as a rough benchmark, not as a substitute for a personalized retirement income plan.

When should I start planning for retirement?

The earlier planning begins, the more options are available. However, the decade immediately before retirement, typically ages 55 to 65, is when the most consequential decisions arise and when the value of a comprehensive strategy is highest. Decisions made during this window, including Social Security timing, account withdrawal sequencing, Roth conversions, and healthcare coverage, often cannot be undone. If you are within 10 years of retirement and do not have a written, strategy-first plan, starting now is appropriate.

Does Minnesota tax retirement income?

Yes. Minnesota taxes most retirement income at ordinary income tax rates. As of 2026, traditional 401(k) and IRA distributions are fully taxable, Social Security benefits are taxable for single filers with AGI above approximately $105,000 and married filers above approximately $130,000, and the state provides no broad retirement income exclusion. Minnesota also has an estate tax with a $3 million threshold, which is significantly lower than the 2026 federal exemption. See our full Minnesota Retirement Tax Guide for details.

Is $500,000 enough to retire in Minnesota?

Whether $500,000 is sufficient to retire in Minnesota depends on your annual spending, income from Social Security or a pension, healthcare costs, expected longevity, and tax situation. At Minnesota's income tax rates, which range from 5.35% to 9.85% (as of 2026, per the Minnesota Department of Revenue), gross portfolio distributions do not translate directly to net income. A comprehensive retirement income analysis, rather than a single savings number, is the appropriate way to answer this question for your specific situation.

What does a first conversation with a financial advisor look like?

At New Horizons Boutique Financial Services, the first conversation is designed to be straightforward, no-pressure, and focused on understanding where you are and what questions you have. There is no cost, no obligation, and no product pitch in that first meeting. The goal is to give you clarity about whether a formal planning engagement makes sense for your situation, and to answer your most pressing questions about retirement readiness, tax exposure, or financial independence.

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Avoid the Mistakes That Undermine Retirement Security

The first step is a conversation, not a commitment. Schedule a no-cost, no-obligation consultation with our team. We will listen, answer your questions, and give you a clearer picture of where you stand and what a strategy-first retirement plan could address for your situation.

New Horizons Boutique Financial Services | 8647 Eagle Point Blvd. Suite #1, Lake Elmo, MN | info@newhorizonsbfs.com

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