You’ve made the decision to retire and are counting down the days. Ideally, you should be planning carefully for this day at least five to 10 years in advance of your desired retirement date. Here are some critical steps to consider as you prepare for this next chapter of your life:


Make sure you are prepared emotionally to step away from working and all the responsibilities that have, in many cases, consumed a good amount of your time and life over the last 40-plus years. Some individuals will look for a part-time second career that is less demanding but just as fulfilling after retiring.

Consider your personal goals and how you want to spend your time after you retire. You could volunteer, become a mentor to younger individuals, travel, or spend more time with family and friends. You could also pursue hobbies that you couldn’t enjoy because work got in the way.

If your career played a major role in your happiness, consider seeking the help of a counselor. Many business owners and employees in leadership find that having a “life coach” can assist them with the transition from working to retirement.


Going from a regular paycheck to retirement can be stressful if you don’t plan ahead. Consider this checklist to help you prepare:

  • Gather a complete list of all your accumulated assets. This includes 401(k) plans, IRAs, personal investment and bank accounts, and any other financial assets and accounts.
  • If you own a business, you will need a succession plan to help you transition your company and provide you with liquidity in retirement. You should start the succession process well in advance of retirement, since transitioning a closely held business can take many years. .
  • Know your income sources during retirement. This may include Social Security, retirement/pension payments, and other sources of income that may be available after you stop working full-time. And speaking of Social Security, you will need to decide when to start claiming your benefits. No standard answer exists because everyone’s situation is different.
  • Assess your spending, and don’t forget to include any special travel or unique spending goals for your retirement. Be realistic, and include items such as obligations to financially contribute for care of aging parents or other family members with special needs. If you are retiring young, you may have college education or responsibilities to care for children during your retirement years.


  • Do you qualify for Medicare coverage? Evaluate the options carefully. You may need a Medicare supplemental plan to cover expenses not allowed by Medicare. Medicare premiums are based on income from your tax return from two years prior, but you may qualify for a lower premium if you cite a “Life Changing Event” when filing for Medicare upon retirement and submitting a projected level of income.
  • If you do not qualify for Medicare, how long will you need coverage until you reach age 65? What are the choices and costs? Will taking COBRA from your former employer be part of the solution, or will buying a personal policy be better? Your answers depend on facts and circumstances related to your situation..
  • Consider long-term care needs. How will you pay for this should you or your spouse need care? What will it do to your retirement, and how can you protect against the risk?


Your taxes are an important part of your planning. It’s key to review how you will use your income stream, investment assets, and retirement accounts in retirement. A carefully thought out plan can mean you will keep more of your assets during your life or have more to leave to your heirs. Do not make the mistake of thinking you will only draw down your IRAs at the mandatory age of 72. In many cases, income tax rates go down in retirement and present an opportunity to start drawing IRA funds at these lower tax rates. Every case is different and should be reviewed annually. Your strategy may change from year to year throughout retirement, depending on income draws, tax rates, and other factors.

Wealth Planner and Advisor

There are many moving pieces to planning for a successful retirement. Align with a professional who can assist with all these decisions. Stock market returns, interest rates, income taxes (including law changes), and our own personal needs and goals fluctuate from year to year. Taking this journey with an advisor who has the depth and experience to help keep you on target can help provide you with peace of mind to enjoy retirement and help reduce the worry about how to adjust on an ongoing basis.

Congratulations on your decision to retire! You are finally able to enjoy the fruits of your labor. These are some of the important factors to consider as you approach retirement, but there are many more. Because you may live 30 years or more in retirement, it pays to plan ahead. Your future self will thank you.

This is intended for educational purposes only and should not be construed as personalized investment or financial advice. Please consult your investment and financial professional(s) regarding your unique situation.

Author Angie M. Stephenson Financial Advisor / Managing Director

Angie has been involved in the financial services industry since 1995. She earned a bachelor of science degree in accounting from Concord University.

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