Five Regrets of Retirement and How to Plan Better

Retirement is a milestone that many of us look forward to, envisioning days of relaxation and the freedom to pursue long-held dreams. However, retiring can also bring many unexpected feelings, including regret. Reflecting on the experiences of countless retirees, certain common regrets emerge. Below are the five most common ones:

  1. Not Saving Enough

One of the biggest regrets among retirees is not putting away enough money for their golden years. Many people find that their savings and pension don’t stretch as far as they’d hoped, as life expectancies increase, and retirement lasts longer. The regret is not just about not saving more but also about not investing wisely or starting to save early enough in life to benefit from the power of compound interest.


  • Start saving as early as possible.
  • Take advantage of employer retirement plans and matches.
  • Consult with a financial advisor to help make smart investment choices.
  1. Retiring Too Soon

Many retirees should consider the financial and emotional impacts fully. Some realize they underestimated how much they would need to live comfortably, while others miss the sense of purpose and community their job provided. This can lead to a desire to return to the workforce, sometimes in a more limited or different capacity.


  • Carefully plan your retirement age, factoring in financial needs and personal goals.
  • Consider part-time work or volunteering to maintain a sense of engagement.
  1. Overlooking Health Care Costs

Healthcare can be one of the most significant expenses in retirement, yet it’s often the most overlooked. Retirees sometimes regret not purchasing long-term care insurance or not factoring in the high cost of health and medical needs, which can consume a considerable portion of retirement savings.


  • Explore health insurance options that cover long-term care.
  • Set aside savings specifically for health-related expenses.
  1. Neglecting to Plan for a Purposeful Life

Retirees often envision retirement as a permanent vacation. However, without the structure of a job, days can feel empty. Regrets can include having yet to develop hobbies, social networks, or plans for how to spend all that free time. Retirement provides the opportunity to explore new interests, volunteer, or even pursue a second career.


  • Identify interests and hobbies before retirement.
  • Create a retirement lifestyle plan that includes activities and goals.
  1. Failing to Estate Plan

Estate planning is essential, yet it’s easy to put off. Retirees sometimes regret not organizing their financial affairs earlier, which can lead to family disputes or assets not being distributed as intended. Not having an updated will, beneficiaries, or a clear plan can create unnecessary stress and conflict for loved ones.


  • Start estate planning early and review your plan regularly.
  • Ensure all legal documents are in order and express your current wishes.


Retirement should be a rewarding phase of life, but it has potential pitfalls. The common thread among these regrets is a lack of planning. By recognizing and addressing these regrets now, no matter your age, you can take steps to mitigate them and work towards a retirement that is fulfilling and free of remorse. Remember, it’s never too late—or too early—to start preparing for your retirement years. To know more visit

This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, accounting, legal or tax advice.  The services of an appropriate professional should be sought regarding your individual situation.

*DISCLAIMER Executive Planning Group offers securities products through ValMark Securities, Inc., Member FINRA / SIPC. While ValMark Securities, Inc. is registered to sell securities products in all 50 United States and the District of Columbia, representatives of Executive Planning Group may only offer securities products in states where properly registered. Executive Planning Group also offers investment advisory products through ValMark Advisers, Inc., an SEC Registered Investment Advisor. The information contained herein should not be considered a solicitation or an offer to sell products or services in any state besides those in which Executive Planning Group is properly registered/licensed. Executive Planning Group, P.A. is a separate entity from Valmark Securities, Inc. and Valmark Advisers, Inc.

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