The Best Time of Year to Retire

Author:  Don’t Just Retire — Live It, Love It!
All of us were meant to be happy and successful.  Life is more than a two-week vacation once a year.  It is, and can be, exactly what you want it to be.  There are no limits except those you put on yourself.
Thomas D. and Jane C. Willhite

Have you ever wondered, “When is the best time of year to retire?”  A simple question but one which has a number of factors to be considered.  Not only are there financial implications to think about but also consideration should be given to the season at the time of retirement.  Be sure to check the programs at your company before tendering your resignation.

A. Cost of Living

Some employer benefit programs state an employee must be retired on or before July 1st (meaning the last working day would be June 30) to receive any cost-of-living increase on a pension granted for July 1st.  This means your on-going pension will actually be less if you retired in July or August compared with retiring on or before July 1st.

B. Vacation Payoff

The first week of January may be appealing to begin your retirement especially if you are  carrying more than the maximum accrual for vacation.   You could get paid for the total as long as you retire before the end of the first pay period in January.  Retiring in January also gives you the entire year to absorb any lump-sum payoff.

C. Tax Considerations

Tax considerations and the best time to retire are different for each individual.  It’s worthwhile to estimate your taxes based on different dates throughout the year and I strongly recommend getting advice from a tax advisor a year or two before you plan to retire.

D. Season

Regardless of when you choose to retire, it is important to plan activities or events to counter or coincide with the season.  For example, if you retire in January, you may want to start with a trip to the sunny south or take a ski holiday.  However, if you choose to retire in the winter months (January — March), and happen to live in one of the Northern States or Canada, you may face many grey, cold, snowy days that can give the inaugural weeks of retirement a bleak feeling.


Retiring in the spring (April — June) and the prospect of gardening and being outdoors may be appealing.  Or perhaps you prefer the summer (July — September) and spending additional time at the cottage to officially launch your new life.  The fall months (October — December) may be ideal as this is a time of completion, celebration and planning for the New Year.

When planning for retirement, decide the time of year best suited for you and your spouse from a financial, seasonal and goal perspective.

Richard (Rick) Atkinson, author of Don’t Just Retire — Live It, Love It! is Founder & President of RA Retirement Advisors and an expert in holistic retirement planning.  Known for his practical, interactive and results oriented The First Step workshops, Rick has helped people throughout North America plan for a successful and fulfilling retirement.
Don’t Just Retire — Live It, Love It! is available at Chapters/Indigo stores and on-line.  The book can be ordered directly at
Looking for a guest speaker?  Thinking about providing holistic retirement planning sessions for your employees or clients?  Contact Rick at 416-282-7320.


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