Five Star Logo
As seen in
Chicago Five Star award winner
Marketing partner logo

6 Questions to Ask Before You Retire

Selected content image

Retirement is one of life's biggest milestones, but deciding when you're ready involves much more than reaching a certain age or hitting a savings goal. The years leading up to retirement are an ideal time to evaluate your financial picture and make sure your plan reflects your goals, lifestyle, and long term needs.

Here are six important questions to consider before making the transition into retirement.

1. Have I Saved Enough?
This is often the first question people ask, but the answer depends on more than the size of your retirement accounts.

Your retirement savings need to support the lifestyle you envision, how long you may be retired, and your anticipated expenses. Factors such as healthcare costs, inflation, travel, home maintenance, and unexpected expenses should all be considered.

Rather than focusing on reaching a specific dollar amount, it's often more helpful to determine whether your savings can reasonably support your expected spending over time.

2. Where Will My Retirement Income Come From?
For many people, retirement means replacing a regular paycheck with income from several different sources.

These may include:

  • Social Security
  • Retirement accounts such as 401(k)s and IRAs
  • Pension benefits, if available
  • Taxable investment accounts
  • Part time employment or consulting income
  • Rental or other passive income
  • Understanding how these income sources work together can help create a more predictable retirement income strategy.

3. When Should I Claim Social Security?
For many retirees, Social Security represents an important source of guaranteed lifetime income. Deciding when to begin benefits is a personal decision that depends on many factors, including your financial needs, health, life expectancy, and overall retirement plan.

Claiming benefits earlier provides income sooner but generally results in smaller monthly payments. Waiting to claim may increase your monthly benefit, although delaying is not necessarily the right choice for everyone.

Evaluating Social Security within the context of your overall financial plan may help you make a more informed decision.

4. How Will Taxes Affect My Retirement?
Many people are surprised to learn that retirement does not necessarily mean paying less in taxes.

Withdrawals from traditional retirement accounts are generally taxable, Social Security benefits may be taxable depending on your income, and Required Minimum Distributions begin later in retirement for many account owners.

Thinking about taxes before retirement may provide opportunities to manage taxable income over time and help avoid unexpected surprises.

Because tax laws are subject to change and individual circumstances vary, it's important to evaluate tax decisions within the context of your personal financial situation.

5. Is My Investment Strategy Still Appropriate?
The investment strategy that helped you build your retirement savings may not be the same strategy that's appropriate once you begin relying on those assets for income.

As retirement approaches, it's often worthwhile to review your investment allocation, overall risk level, and liquidity needs. While every investor's circumstances are different, your portfolio should continue to align with your goals, time horizon, and comfort with market fluctuations.

Market volatility is a normal part of investing, and having a long term investment strategy can help provide perspective during periods of uncertainty.

All investing involves risk, including the possible loss of principal, and no investment strategy can guarantee positive results.

6. Do I Have a Plan for the Unexpected?
Retirement planning isn't only about preparing for your ideal future. It's also about preparing for the unexpected.

Consider questions such as:

  • How would I handle a significant healthcare expense?
  • Have I reviewed my insurance coverage?
  • Are my beneficiary designations up to date?
  • Do I have current estate planning documents?
  • Would my spouse or family know where to find important financial information?
  • Addressing these questions before retirement canĀ help you prepare for future financial decisionsĀ and help reduce stress for you and your loved ones.

Final Thoughts
There is no single checklist that guarantees a successful retirement, because every person's goals and circumstances are different. However, asking the right questions before you retire can help you identify planning considerations, prepare for potential challenges, and make informed financial decisions.

Retirement is more than reaching a destination. It's about creating a plan that supports the life you want to live, while remaining flexible enough to adapt as your needs evolve.

Important Disclosure: This article is provided for informational and educational purposes only and should not be construed as investment, legal, or tax advice. All investing involves risk, including the possible loss of principal. Past performance does not guarantee future results. Individuals should consult with qualified professionals regarding their specific financial circumstances before making financial decisions.

This award was issued on 10/01/2026 by Five Star Professional (FSP) for the time period 02/18/2026 through 07/31/2026. Fee paid for use of marketing materials. Self-completed questionnaire was used for rating. This rating is not related to the quality of the investment advice and based solely on the disclosed criteria. 6433 Chicago-area wealth managers were considered for the award; 325 (5% of candidates) were named 2026 Five Star Wealth Managers. The following prior year statistics use this format: YEAR: # Considered, # Winners, % of candidates, Issued Date, Research Period. 2025: 6,399, 362, 6%, 10/1/25, 1/1/25 - 8/1/25; 2024: 6,273, 400, 6%, 10/1/24, 1/9/24 - 8/9/24; 2023: 5,549, 405, 7%, 10/1/23, 1/9/23 - 7/31/23; 2022: 4912, 384, 8%, 10/1/22, 1/24/22 - 7/29/22; 2021: 5635, 386, 7%, 10/1/21, 12/28/20 - 8/6/21; 2020: 4636, 356, 8%, 10/1/20, 1/6/20 - 8/7/20; 2019: 5430, 429, 8%, 10/1/19, 1/7/19 - 8/9/19; 2018: 5449, 435, 8%, 10/1/18, 1/12/18 - 8/17/18; 2017: 3781, 438, 12%, 10/1/17, 12/16/16 - 8/3/17; 2016: 3411, 726, 22%, 9/1/16, 2/26/16 - 8/19/16; 2015: 5833, 716, 12%, 10/1/15, 2/4/15 - 8/3/15; 2014: 8161, 744, 9%, 10/1/14, 2/4/13 - 8/3/13; 2013: 3998, 772, 19%, 10/1/13, 2/4/12 - 8/3/12; 2012: 2970, 780, 26%, 10/1/12, 2/4/11 - 8/3/11.
Click to access BrokerCheck

Investment Advisory Services are offered through K&H Wealth Partners Inc. (KHWP), a registered investment adviser. Insurance products and services are offered and sold through Karchmar Life Insurance and Legacy Planning Inc. and individually licensed and appointed agents in all appropriate jurisdictions.

*Winners appearing on this page do not pay a fee to be considered or to win the Five Star Award. Professionals with a digital profile have paid a promotional fee.
Wealth managers do not pay a fee to be considered or placed on the final list of Five Star Wealth Managers. The award is based on 10 objective criteria. Eligibility criteria - required: 1. Credentialed as a registered investment adviser (RIA) or a registered investment adviser representative; 2. Actively licensed as a RIA or as a principal of a registered investment adviser firm for a minimum of 5 years; 3. Favorable regulatory and complaint history review (As defined by FSP, the wealth manager has not; A. Been subject to a regulatory action that resulted in a license being suspended or revoked, or payment of a fine; B. Had more than a total of three settled or pending complaints filed against them and/or a total of five settled, pending, dismissed or denied complaints with any regulatory authority or FSP's consumer complaint process. Unfavorable feedback may have been discovered through a check of complaints registered with a regulatory authority or complaints registered through FSP's consumer complaint process; feedback may not be representative of any one client's experience; C. Individually contributed to a financial settlement of a customer complaint; D. Filed for personal bankruptcy within the past 11 years; E. Been terminated from a financial services firm within the past 11 years; F. Been convicted of a felony); 4. Fulfilled their firm review based on internal standards; 5. Accepting new clients. Evaluation criteria - considered: 6. One-year client retention rate; 7. Five-year client retention rate; 8. Non-institutional discretionary and/or non-discretionary client assets administered; 9. Number of client households served; 10. Education and professional designations. FSP does not evaluate quality of services provided to clients. The award is not indicative of the wealth manager's future performance. Wealth managers may or may not use discretion in their practice and therefore may not manage their clients' assets. The inclusion of a wealth manager on the Five Star Wealth Manager list should not be construed as an endorsement of the wealth manager by FSP or this publication. Working with a Five Star Wealth Manager or any wealth manager is no guarantee as to future investment success, nor is there any guarantee that the selected wealth managers will be awarded this accomplishment by FSP in the future. Visit www.fivestarprofessional.com.