How Do You Know When To Retire? by Bob Lowry Satisfying Retirement

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By Bob Lowry

“When should I retire” is a question I hear a lot. Comments left on the blog or e-mails filling my inbox ask for help in knowing when it is time to call it quits. The answer I give is usually the same: For your individual situation, I have no idea. Retiring from your present full-time job to begin your satisfying retirement is one of the more important decisions you will make during your lifetime. There are so many factors to consider that you must put in the time and effort to come to the best answer for you.

I wrote the  following post about 6 months ago. In looking it over I think the information is valuable enough to repeat now without many changes. I have a lot of new readers who may not have seen this the first time. If so, I urge you to add your comments at the end. Fresh input is very valuable to all of us. If you remember reading this post when first published, I hope a second time will spark your thinking about one or more of the points raised.

You know it is time to retire when….

You dread going to work everyday. You are tired and dispirited. Everyone has an off day or a few days every now and then. But, if that feeling is present pretty much all the time, you may have reached your limit.


You are being asked to do more work for a less money. This is the hidden message in that last productivity memo you received. To preserve your job you will have to accept a salary cut and pick up the slack of those unfortunate souls who got a pink slip. For the short term it may be in your best interest to accept this. But if the situation begins to look semi-permanent, you may have second thoughts.


You feel the essential “you” is slipping away. There isn’t enough time for you to do what satisfies you and makes you happy. You find yourself doing things that make you uncomfortable. Your world has shrunk to work-sleep-work.

You can’t wait to get home to work on a project or new passion. Closely tied to the “you” reference above. All your thoughts revolve around after work hours. There never is any time to do that thing you really love.

You complain to anyone who will listen (and even many who will not) about work. Spending your energy and life in a negative place increases your stress and shortens your life. It is also a quick way to get fired.

You have saved enough to live without a regular paycheck. You have run the numbers so often your calculator is melting. There are solid income streams that make you feel you can do this. You have thought through contingencies. You have thought about worst case scenarios. The numbers still work. You feel confident in your financial planning and long term situation.


A loved one is very sick and you’d rather spend your time with that person while you can. Whether a parent, child, relative, or best friend, there is no do-over if that person isn’t likely to be with you through your retirement. Do you feel strongly that person needs you right now? 


Your health is beginning to slip and you have things you want to accomplish while you still can. In this case you are on the other side of the fence. You are sure you will not be physically or mentally able to do what you’d like to do if you wait too long to retire. You decide it is more important to enjoy your freedom while you have it, even if it means a more limited lifestyle.


You have affordable alternatives for acceptable health insurance and care. This question is hard to answer at the moment. Everything seems to be in a state of flux. But, if your health coverage through work will continue, or your Medicare and supplemental policy are working well you are better off than many. Plan to spend much more than you think you will. If the budget still works you have dealt with one of the biggest hurdles to a satisfying retirement.



You are excited about making a major change in your life (where you live, how you spend your time) Change is life. A life without change is in a rut. Change can be stimulating, exciting, terrifying, and necessary. Sometimes you just have to shake it up and that thought gets your blood racing.


Your self-identity isn’t defined by your job. You have a life and and sense of self worth not dependent on work. This is important. There are few things sadder than someone who retires and discovers he has no life outside of work. If you have at least some friends who are not co-workers, enjoy hobbies or other activities you are much closer to being ready to leave the job.


What do you want to do with the rest of your life? When do you want to do it? Aren’t those the most important questions? When you can answer them you may be ready.



Which of these questions and statements fit your situation? If you are retired, which ones were most important to you when you made the decision? Retirement today is quite different from a retirement lifestyle of even 10-15 years ago. You may plan for more work. You may want to stay in your home as long as possible. Sun City holds little appeal. You may be chomping at the bit to spend a few years overseas on mission work. You are ready for a new phase of your life, not for your life to end in a whimper. Your thought: retirement  only the beginning of a new part of my life.


How do you know when to retire? You just do.

By Bob Lowry

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