March 3, 2020

How Do I Know It Is Time To Retire?




This is one of the posts that continues to be read several years after first being published. Knowing when to retire is a key question we all must answer at some point.

For those of you not yet retired these points should help you determine how close you really are. If you are retired, please add your comments at the end, indicating which of these factors were most important to you when you moved into this new phase of life.

One of the questions I get asked most often is, " How do I know when it is time to retire?"  The answer is I don't know when you should retire, but I can give you some indicators to look for.  Then, you will have to decide if the time is right. 

With that disclaimer out of the way, when several of these indicators are present it may be time to retire.

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

Your are being asked to do a lot more work for no more money. This is the hidden message in that last productivity memo you received. To preserve your job you will have to accept the situation 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 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 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. Your health coverage through work will continue or your individual policy is still functioning. You may be able to find a policy, with a subsidy, that works. Over 65? Medicare and supplemental policies are your answer. 

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.


There you go: a checklist for retirement decisions. I encourage your comments and additions to this list.

22 comments:

  1. Bob, I can see why this remains a popular post. You make excellent points, and every single one of them deserves serious contemplation. One additional point comes to me because it's the main issue that prompted my escape from the workforce: Your job is impacting your health in a negative way on a regular basis. (You did address the health perspective, but in a slightly different way.) I loved my job, but the associated stresses led to higher blood pressure and me waking up in the middle of the night filled with angst about the upcoming day and unable to get back to sleep. Originally, I had planned to leave the workforce when our younger child graduated from high school, in effect, "graduating" with her. But I couldn't hold out, and escaped a full year before we had planned my departure. As you mentioned, I had been running the numbers for several years, and we were fortunate in knowing that we'd be on solid financial ground. I'm convinced that staying would have had dire consequences for my health, as within weeks the full nights of restorative sleep and a return to an active lifestyle had me back to my old, healthy (and, just as important, happy) self. Good health is such a blessing. I can't tell you how relieved I am that I didn't sacrifice mine for the job.

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    1. For many years I suffered from a purely imaginary problem, but it directly affected my stress levels and ability to enjoy what I was doing: Imposter Syndrome. I kept waiting for a client to realize I really didn't know what I was talking about and bring to light my lack of real expertise. When I was on a business trip, I'd wake up in the hotel room and dread going into the client's place of business, just knowing they would be ready to expose me.

      That scenario never happened, but the fear had a definite impact on me. Of course, as soon as I retired that particular stressor stopped. Nobody is an expert at retirement!

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  2. I started working for the company I retired from in 1987 and at the time they were owned privately. Eventually they sold to a foreign entity and then they sold it to a large US conglomerate and then they sold it to private equity and two years later we went public. The gentlemen I was working for when bought by private equity was forced out, he was the Business Manager and I was his “wing man”. The new boss had a super ego and pretended to value you to get information and then he would stab you in the back. I was demoted although they couched it as a bigger position and my bonus percentage was cut two years in a row. Before Mr. Ego, I had felt valued although overworked. There had always been a lot of stress and managing through 4 different owners was not easy. My plan when I entered the workforce was always to try and retire early, I knew I wanted to do other things. So I had prepared financially.

    I can identify with almost every indicator on your list except my health was excellent. Even though work was very stressful, I had no problems sleeping at night and often wondered why that was. I think I was good at compartmentalizing which was hard when you get work emails and phone calls after hours. Anyway, I pulled the plug from the career at 59 and stopped consulting a year after that. I love retirement.

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    1. Surviving four different owners at the same company is quite a trick. How did you even keep their names, positioning, and home office locations straight?

      I was not that good at compartmentalizing. To do so takes real mental discipline and having something that is very pleasurable or engaging that isn't work-related to occupy your mind.

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  3. thanks for the repost. this was the first time i read it. I am definitely the first one (dreading coming into work) and the complainer (i don't need to get fired).
    Now I just gotta get there. Just 6 months, 3 weeks and 5 days to go. but who's counting

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    1. Keep your head down and complain silently. Just think, by Halloween you will be done.

      Glad you found some points of reference in this post.

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  4. ALL TRUE! I resigned July 1 last year. Final work day, July 26. DONE! I'm feeling rested, healthy and joyous each day. For the first 10 weeks I slept 8-11 hours a day!!!! I've now settled out around 8h.

    More money was not worth the impact on my daily life.

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    1. Money is never a good trade for the priceless resource of time spent the way you choose.

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  5. Hi Bob. This post could not be more timely for me. I can identify with all of these reference points. I am so very tired to the bone, and I almost cry when I have to come in to work everyday. Now, granted, I am fortunate, because my husband and I are selling our own small business, and we are just in the beginning phases. But, I do think we waited about a year to long to pull the plug. Our health and mental stamina are deteriorating for both of us, and I've never been more sure that now is the time, for so many different reasons. It's funny, once you make the decision to go, it's like your body just can't wait another minute to leave. We are hoping to be done by end of summer, if we can last that long. I look forward to all the replies here, as I do all of your posts. Great work you do here, Bob. And thank you for this timely post which, to me, is the universe (and you) telling me it's ok to let go.

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    1. I am always pleased when a post just happens to appear at the right time for someone.

      That feeling you have when your body is almost operating on remote control once your mind has made the decision to go is a familiar one. I hung on for almost a year after I decided it was time to make the break.. But, those checks in the mail and the normal fear of making such a major shift in how your life is lived is not always easy to overcome.

      Best of luck to you and hubby. A wonderful world awaits!

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  6. Although I realize that not everyone has the option, I have always felt that one should retire to something (exciting plans, travel, etc.) rather than retire from something (a hateful job, boss, boredom, etc.). My husband and I were lucky in that we both liked our jobs and the easy social network they provided, we just felt that we wanted the freedom to do other things.

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    1. You are so right: it is always preferable to retire to something instead of just from work, but that isn't always possible. As the commenter just above notes, they are desperate to break free. The stress of hanging on makes leaving work imperative, even if they haven't figured out what lies ahead.

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  7. Bob I could feel my fear returning after reading the first couple of posts. Near the end the stress was getting to me, I didn't like some of the people that I was working with, and I didn't like what they were asking us to do. But my frustration was due to me doing "bad work.'I didn't really want to retire I wanted to make it to the proverbial finish line but thankfully they packaged me off and my life suddenly changed for the better. I realized that I wanted to keep working at something but it had to be great work what I call my art and thankfully I did find it. Why retire from something that you love to do?

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    1. It is usually a mistake to retire from a job/career that you enjoy. There is no doubt that the satisfaction from a job well done is good for our mental and physical health. It gets difficult, though, if you love your job but find the work environment poisonous. Then, switching place of employment or pulling the plug if you are able are the safest choices.

      Glad it worked out for you, Mike.

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  8. I voluntarily retired at 60. My employer exhibited all the signs of a coming buyout or merger. I left and the stuff started hitting the fan 4 months later. Unfortunately for those still employed there they suffered even more than I foresaw. I have not had a single day yet that I wish I was back at work. I don't advise people my age because their die has already been cast. For younger folks please remember there is massive age discrimination out there. Waiting till your fifties to ramp up your retirement savings may be too late. Health, economic or employer issues may prevent you from working as long as planned.

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    1. So true. I always shudder when someone says they plan on working into their 70's so they have plenty of time to save. The reality is actually you say: staying on the job past a certain age (and that depends on the industry) may not be your choice. Then, it is too late unless you figure you can live on Social Security or have a rich relative about to put you in the will.

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  9. I will retire at the end of April. Some of the points identified above are true - most of the time - for me. Although I planned all my working life to retire early, I have mixed feelings as the day draws nearer. We are financially prepared, but I worry about the lack of responsibility that having to work has meant in my life. I'm not one who embraces change, I guess.

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    1. Many of us define who and what we are by our job. It is quite normal to worry what you will do after leaving that life.

      Trust me, after a period of uncertainty you will find the freedom to mold your own schedule, spend time as you want, and discover new aspects of your personality to convince you the decision was the right one.

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  10. I retired a month ago, with a few of these. One thing about health, it doesn't have to be bad necessarily. We're all trending in a downward direction, so better to pick a point before it becomes a problem and have time to exercise & slow the trend.

    I didn't consider my job extremely stressful, but it must have had an effect that I didn't really understand - any time I ever dreamed, I had nightmares. Fortunately some nights I didn't dream (or wasn't startled awake by them). I thought it was normal (for me), but the nightmares just stopped when I retired.

    So far it just feels like Saturday - a REALLY long Saturday. And Saturdays are the best!

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    1. 19 years after retirement and I still have occasional nightmares that are related to my former career. I guess they never stop!

      You are enjoying the honeymoon period of retirement: every day is a blessing and seems like time stretches forward with no limitations.

      Enjoy!

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  11. This question was also posed recently by a reader on another forum that I frequent. My response was succinct. When the Sunday Blues that used to kick in at 4 pm on Sunday started to kick in at 4 pm on Saturday, I knew it was time to go. Two and a half years later I have not looked back.

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    1. I like that measure of when it is time to go.

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