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The 10 Worst Retirement Mistakes

Category: General Retirement Issues

August 6, 2011 — (Note: This is a 3 part series. See links to Parts 2 and 3 in the “Further Reading” section at end). The most beautiful thing about retirement is that is the perfect moment to reinvent yourself. The kids are grown, your mortgage might be paid, your fight up the career ladder is behind you. It’s a “do-over”, now you are free to do anything you want to, an amazing opportunity! You are only limited by your imagination and your resources (and the former can help with the latter).

To help you maximize this unique chance to start life all over again, here is our list of the 10 worst retirement mistakes you can make. We hope you will keep them in mind so that your reinvention comes off without a hitch. And if you have your own mistakes or success strategies to add, please let us know in the Comments section.

Worst Retirement Mistakes
1. Start planning your retirement the day after you retire.
That’s too late. Smart retirements have regular planning sessions where you think about the W questions – Where, When, Why, What (are you going to do) – and How you are going to afford it. Develop a plan and put it on paper… before you get that gold watch.

2. Retiring too soon. Some folks are so eager to get away from their jobs that they jump the gun. Premature retirement, either before you are ready emotionally, or before you can really afford it, can be disastrous. It’s hard to get back into the employment scene after you’ve left and your skills are rusty. Be sure before you pull the trigger.

3. Continue to live in the suburbs. Sure, you might want to retire in the same house you do now. But here are three reasons not to: Your maintenance, utility, and tax expenses will be much higher than many other alternatives. When you get to the point that you can’t drive anymore you will be trapped in your home, without any good mass transit options. And lastly, you will probably be more isolated socially than if you lived in more of a communal setting like a city, walkable town, active community, or independent/assisted living/CCRC facility.

4. Don’t visit enough places before you decide where you are going to live. You might think you have checked things out, but until you have seen a place you don’t really know much. Any one retiree might be happy in dozens of towns or communities. Explore a little and be sure.

5. Don’t rent before you buy. It is so tempting to visit a town or community and buy a brand new unit. But to figure out what it’s really like living there, it will take more than a brief visit. We have heard this refrain enough times to repeat it again – “if only I had rented first, I would have known…” Renting is easy, and in this unsettled environment, almost always a good idea.

6. Don’t do enough due diligence. We are always amazed at the otherwise careful people who brush over some of the most basic due diligence issues before they buy. The list of issues you need to check up on is long, and important. Those include reading the Home Owners Association rules, studying the most recent financial report, getting minutes from HOA meetings, finding out about foreclosures and dues arrears, finding out what your neighbors are like, getting a fix on maintenance sinking funds, etc. If it’s a new community there will be other questions – how likely is it the community will sell out, what happens when ownership is transferred, what kind of obligations and assets will be transferred to the Home Owners association. Your realtor and attorney should be able to help you with all of these. Too many communities are having too many issues for you not to investigate everything carefully.

7. Move too far from family & friends. In our experience the #1 reason for an unsuccessful retirement move is that the person moved too far from their families and/or friends. Your children and grandchildren exert a very powerful tug – so before you move too far away, carefully consider how you will compensate for that.

8. Assume your kids will take care of you in your old age. Your kids have their own lives. Even if they want to take care of you, they might not have the time, temperament, or resources. So plan out in advance where you will live and what you will do if you are fortunate enough to live a long time after retirement, when almost everybody needs some kind of assistance and companionship. Likewise, try to plan for 1 move rather than a couple of moves.

9. Move to an incompatible environment. Examples would be moving to an active adult community if you hate rules, moving to a rural environment and you crave activity, or moving to a liberal environment when you are a conservative person. Visit before you rent, rent before you buy, and there will be fewer surprises.

10. Move to a new community without a plan to meet people. If you move to an active adult community it is hard not to meet people. But folks who buy a home in a general neighborhood or suburban development need a plan to meet people and build a new social life – they need to join a church, club, volunteer, take part in activities, or get a job.

Further Reading
Part 2: 10 More Retirement Mistakes You Don’t Want to Make
Part 3: Avoid These 6 Retirement-Wrecking Mistakes
Retirement Ranger
– Quiz: How Ready for Retirement Are You?
Countdown to Retirement Success

What do you think are the worst retirement mistakes? Have you made some yourself? Please share your ideas about retirement mistakes – and successes – in the Comments section below.

Posted by John Brady on August 6th, 2011


  1. I think that the most fatal mistake is to retire too soon. In the world we are living today, nothing can be guaranteed and economic recessions may happen at any time. Any economic crisis may be fatal for those who didn’t save too much.
    Thanks for this great post!

    by Janett Brown — August 7, 2011

  2. Whether you’re moving or plan to stay in your current residence when you retire, be sure your home has elements of universal design, such as higher cabinets, wider hallways, curbless showers, rocker switches, first floor master (or an elevator), “comfort height” toilets” – universl design will help you to stay there longer.

    by Jan Cullinane, co-author The New Retirement: The Ultimate Guide to the Rest of Your LIfe (Rodale 2007) — August 8, 2011

  3. Top of the list of mistakes was to purchase and not rent first. The community we moved to is extremely closed socially, meaning it operates within clique structure. This was very foreign to me and making friends here has been impeded because we are not from here and it is readily noticed by our lack of local accent. At first the encounters we had seemed to demonstrate interest in us but it became the routine these encounters were superficial and anything further was difficult or not available.
    Secondly I had the notion that I could find employment that would be somewhat commensurate with my work skills. That was also a large mistake. I am working part time for wages that I have not seen in over 30 years. Some of this was due to age (58) when the move occurred and perhaps more was not fitting in because of being self employed for 25 years prior.

    I am now looking for the next place to live.

    by Rob — August 10, 2011

  4. This “reverse” list is one of the best articles you’ve posted! I can go through it and find one or three things I have yet to consider. Thank you.

    by LuluM — August 10, 2011

  5. Dont put off hobbies and travel until you retire. you dont know if retirement will bring you all the things you havent been able to do.
    size down on your house, travel, put work second, you are first then your husband, then the kids (given that they are grown). Plan family vacations, even if its camping. They are most important

    by jean lac — August 10, 2011

  6. 11. Don’t move to Connecticut unless you enjoy being taxed at some of the highest rates in the country! If you make over $50,000 are single or 100,000 are married, your social security is taxed. Just one example. State motto should be “tax and spend”.

    by Elaine DeTulio — August 10, 2011

  7. Sandy at this end:
    After knowing we wanted and could retire in a warmer climate (retirement was fast approaching). We each made our own lists and then combined. (Once we wintered in a warmer location, we started looking for places to live year round if fits our combined lists.)

    Creating a:
    Yearly expense list compared to yearly revenue list. (you really will spend the same amount, because you will do ‘fun’ things, but living in a lower cost of living helps reduce living expenses.)
    BUCKET LIST – all the things we wanted to do
    Options of how we would live – 2 homes, wintering only in warm climate, RV, etc
    What is important to where we live
    Then we asked these questions:
    Do we want to move again
    De we want/can afford 2 homes
    What will we need in the future – even in the worst situation

    Once we realized we could retire and retire with warm winters, we started to list what our needs would be:
    Live in a location that has easy access to airports – for family visits
    Find an assisted living facility that was close or included in our living community
    Golf cart transportation or bus service when we could no longer drive

    To determine what we should look for, we each made a list of features that were important to us in a community and a second list for the house We ranked the importance of each feature. We used a 1-10 scale – 10 being the best. Then we combined our lists and put all of our 10s (can’t live without) together. We knew that we had to have these features in any community or house search we conducted.

    Much of our knowledge came from talking to other snowbirds, and going to sessions where seniors talked about what they were doing or how they were doing such activities. I found that each snowbird location have some kind of sessions for the snowbirds and great information can be accessed at these expos. Lots of articles and of course, the internet is wonderful to read what other retirees are doing i.e. this great site!
    Hope this helps.

    by sandy — August 11, 2011

  8. To expand on Elaine DeTulio’s above depiction of Connecticut state taxes: go to for detailed information about each state’s tax burden (as well as many other retirement-specific indices) Social Security taxed? Military pensions? Private pension? IRA’s? Food? Real Estate?
    all itemized.

    by oldnassau'67 — August 12, 2011

  9. Oldnassau is right on, RL has great info on state taxes. Ct is right up there for high taxes. We are working to add more detailed tax details on our state guide pages –

    by Admin — August 12, 2011

  10. My biggest mistake has been moving close to my children in an environment, weather, politically, socially, environmentally, that I do not like. I like to be outdoors (from CA) and it’s impossible here when it’s 100 degrees. Also thinking they would have time for me and that we would really get along better or like each other better. My daughter’s house is such a mess she doesn’t want me there and I don’t want to be there, even though I love the house and her neighborhood. Go for what really matters to you as a person. For me, it’s nature and outdoors.

    by Sharon Roberts — August 12, 2011

  11. Interesting comment from Sharon. My plan has been to follow my daughter and son-in-law up to Maine, but try to stay out of the way; I’ve been living in Connecticut for the past 36 years, and although I have many memories, no one I really care about lives here anymore. I know my “kids” expect I’ll provide free grandchild (eventually) and pet sitting, and at the moment that’s fine with me. I’m not going to like the cold and dark, I know this already, so I hope to winter cheaply in Florida when I retire (currently 52). I don’t mind living in a low-income elderly box as long as there is someone who can get me from point A to point B. I love joining gardening and quilting clubs, and they are SUCH nice people, I know there will be things for me to do. Being single and not owning anything does have drawbacks, but the freedom is not something to be dismissed either. REALLY looking forward to retirement!!!

    by Drumlin — August 12, 2011

  12. hall thought are admirablettp:// all thoughts are admirable and need to be considered.but the worst thing is to not retire at all. do not over think it or you become paralyzed. run with it.before they the gov. take it all away.

    by lonnie mercurio — August 13, 2011

  13. I agree somewhat with Ionnie, although I’m not so worried about our government as much as the tendency of food prices, rents, condo fees, etc to continually go up and out of reach. I think retirement is the time to simplify, simplify, simplify. I’d rather live in a tent than work at a job I hate, put off retirement so I could get more money, only to get sick at 70 and have no retirement at all!

    by Drumlin — August 13, 2011

  14. Are there any people/retirees who reside in the state of FLA. year round.
    Specifically during the summer months. Kindly recommend positive ways on beating the heat, without residing indoors during July & Aug. We live in
    MA and spend a lot of time indoors, especially during Jan., Feb., March.
    This past year, we had the house heat on til almost June. I’m dreading what
    comes after September/October. In a couple of year we’re hoping to relocate
    to FLA. The insights the folks provide on this blog are beneficial. If anyone
    would like to recommend their favorite town/community in FLA., for us to
    consider, we’d greatly appreciate your suggestions. Your guidance and opinions will be scrutinized w/gratefulness. Thank you.

    by Judy — August 13, 2011

  15. Hi Judy,
    I live in Florida year-round. In the northeast. Yup, it’s hot in the summer, but I play tennis – outdoors – three or four times a week. If you live close to the ocean, you’ll see there is a breeze, and it feels ten degrees cooler than the interior of the state. I also golf, ride my bike, walk on the beach, swim, and do everything I did in the summers in the other states I lived – Maryland, Ohio, and New Jersey. You’ll need lots of sunblock, water, and yes, sometimes I don’t walk my dog except early morning and late evening – he is more susceptible to the heat than I am. As you know, this past year, a lot of other states had hotter days than we did in Florida.

    Jan Cullinane, The New Retirement: The Ultimate Guide to the Rest of Your Life (Rodale)

    by Jan Cullinane, co-author The New Retirement: The Ultimate Guide to the Rest of Your LIfe (Rodale 2007) — August 14, 2011

  16. I have lived in FLA Panhandle and now reside in central OK (due to job). I will say that after living in FL, CO, NJ, ASIA and ‘visiting’ the Middle East, you can adapt to any climate. It may take a few months to ‘align’ yourself with the different HOT temps; but after a little while you won’t notice the difference (except maybe when the humidity is 110% ~ which can be in any state in the South or Midwest for a short timespan then it is gone). However, I would add that the mild Winters, beautiful Springs and and gorgeous Falls will get you through the few hot weeks. I will be retiring soon and I am looking at different FL and TX communities….and as for the heat ~~ well, bring it on 😆

    by LT — August 14, 2011

  17. For Jan & LT: Thanks for the encouraging, delightful, uplifting remarks. I just read your comments to my husband, and we’re grinning from ear-to-ear. It’s funny, you should mention how adaptable one can become to weather conditions. After 5-6 weeks of summer weather, I’ve already begun to feel coolness in the air. This past Friday, my husband and I were on a beach in Orleans, MA (Cape Cod) and during the afternoon, I had to wear my emergency sweatshirt I keep in the car. What is your suggestion on recommending the different areas i.e. Sebring, FLA? The Ocala, FLA area sounds beautiful.

    by Judy — August 14, 2011

  18. Hi! Just read some of the commets of home owners living now full time in Florida. Thanks, we are planning a trip to see your state this fall, if anyone has more to add about the weather ” tropical storms” I would like to here what you may have to say. We are from Seattle and ony have the doom and gloom of damp and gray days to deal with. We are looking for a gated 55 home to enjoy,if you enjoy your area let us know the good and bad news. We would like to see a bit of what you call home. Thank You Brad

    by Brad — August 14, 2011

  19. All of the comments have been very helpful to my gf and I. Now we would like to know a few other things, what city/town to call home ( thinking Venice, Punta Gordan, Coral Springs etc.), crime levels in these areas as well as cost of living. I will also like to know what the employment situation is there. My gf is 7 years my junior and will not be able to retire yet.

    by Bill — August 15, 2011

  20. Brad, I would never say Fl is beautiful, unless you are right on the coasts; the interior is just typical Florida, but not subjected to the damage you get on the coasts. We don’t live in FL, but have wintered in Florida for 9 years. From my point of view the northern part of FL is more like the North with lots of oak trees plus the palms and evergreens and that where we are going to retire WHEN we sell our house. I really like the Ocala area it is called the horse country. I like everything above US highway 4. Below 4 doesn’t interest me. That has been our dividing line. If you can afford the coast, anywhere along the Gulf of Mexico is GREAT! I would consider the routes out of the coastal towns and how often you would have to ‘jump’ ship. As I’m getting older I don’t want to be uprooted, so the interior of the state suits me just fine. Good luck and the hot summers are still better than those cold sunless Michigan winters.

    by sandy — August 15, 2011

  21. sorry Brad, that message was for Judy!

    by sandy — August 15, 2011

  22. Re hurricanes…check out You’ll see a great little map – the chances of a hurricane striking northeast Florida (they show the city of Jacksonville) is 1 in 100, while the chances of one hitting the Florida Keys is 1 in 8, and Fort Myers 1 in 11. They show several other locations as well.

    by Jan Cullinane, co-author The New Retirement: The Ultimate Guide to the Rest of Your LIfe (Rodale 2007) — August 16, 2011

  23. […] 16, 2011 — As a followup to last week’s article on the “10 Worst Retirement Mistakes“, our faithful member OldNassau just brought an incredibly interesting article to our […]

    by » Why Toby Bought a Short Sale at Tidelands Topretirements — August 16, 2011

  24. […] References: ?How Ready for Retirement Are You? 10 Worst Retirement Mistakes […]

    by » Pre-Retirees Much More Optimistic About Retirement Than Those Already Retired Topretirements — October 10, 2011

  25. I would like to respond to judy- I realize that these posts are from over a year ago, but maybe others will read them as I have. I have lived in Central Florida for over 24 years. The summer months are indeed hot, however we still manage to do things, like swimming and parks with springs etc.
    Our summer months are like your winters, we turn on the AC and stay inside alot. We make up for it in the fall, winter and spring. I have only turned the heat on once this year. Our utilities are under a hundred dollars and it is a great savings. It all depends on what you get used to. Our weather can be severe, however you get plenty of warning to prepare.

    by Sonjia — December 28, 2012

  26. Sonjia, I had the opposite experience although I didn’t live in FL (my parents did). I liked visiting in the summer because of less traffic and congestion and the “cooler” weather. They lived near Fort Laurderdale (Margate area) and the temp and humidity was less than my weather in Birmingham AL, VA and several place in central and coastal NC. In 2011 (or was it 2010) we in Virginia had over 90 days of over 90 degrees with high humidity and dew points. It was miserable and I was glad to get away to FL for a visit. As always do not judge a whole state by one place Check APALACHICOLA, FL.

    by elaine — December 29, 2012

  27. Going to Menifee, Lake Elsinore, Palm springs and Desert Springs, Calif to check it out. later in JAnuary.

    by Mark — December 30, 2012

  28. Have spent time in Biloxi, Miss. I love the coastal towns of Ocean Springs and Biloxi. Has anyone lived there, rented there, or bought property there? Comments, please, on the two areas. Are they inexpensive (except for casinos!!) and low crime? Is the airport large enough to travel other U.S.A. cities?

    Editor’s note: We notice that for a while this thread of posts has gotten off the track of “Worst Retirement Mistakes” and onto what different places are like to live (although the Florida discussion has been interesting). If your question or (preferably) comment concerns something about where to live, please use one of our other posts that are more germane to that subject, such as

    That way our members can use this thread to talk about retirement mistakes or successes without having to wade through unrelated posts. Thanks!

    by Barbara Stevens — December 30, 2012

  29. Barbara – was in Biloxi, Miaa in the military – many hurricanes. Some years ago the whole costal town was wiped out due to hurrican. We live in Florida and ready to leave because of the same potential problem. Think seriously about the potential danger.

    by Robert — December 31, 2012

  30. Nice try, John. 😀

    by Mad Monk — December 31, 2012

  31. My BIG MISTAKE – not renting in the area I’m living in first. No, I had to go out and buy – in 2006 of course, and I dislike my area tremendously AND am, for the second time, trying to sell my home w/o any luck. So all the advice you read on rent first before you buy is right on the money!!!!

    by Kay — December 31, 2012

  32. I am not yet retired, but we are looking for our “last” home. Living in GA now–dont much care for the humidity in summer. Originally from San Diego. We would love to go back there, but way too much money.

    We are looking at the Tennessee mountains or the pacific NW (we lived in Whidbey Island for a few years)

    We want rural–away from the city, with land and space for my rescue cats

    Any advice or insight?


    by Ruth — December 31, 2012

  33. A mistake to avoid: not checking to see if your insurance will be accepted where you plan to live (some doctors won’t accept Medicare from new patients; you have to have been be an existing patient under some other insurance first).
    Jan Cullinane,
    The Single Woman’s Guide to Retirement (John Wiley & Sons)
    The New Retirement: The Ultimate Guide to the Rest of Your Life (Rodale)

    by Jan Cullinane — January 1, 2013

  34. RUTH – Wow – you don’t want close to a big city and all the hub bub. Someone after my own heart. My husband and I built a house winter of 2012 in Creston, NC. Area of Northwestern NC, close to VA and TN. I love it here. Plenty of open land and rural, BUT 1/2 an hour from Walmart other supermarkets. The summers are gorgeous and coming from SC we know what you mean about humidity. This is our first winter and though we haven’t had any real snow we’ve had a few WINDY days since we’re at 3400 feet. I’ve gone to Boone for one doctor (45 min) and to Abingdon, VA (55 min) for another and have been very pleased. Small hospital in Jefferson (35 min.). Good Luck!

    by Anne MacKinney — January 1, 2013

  35. […] For further reading: Retirement Readiness Checklist Is This the Right Time for You to Retire 10 Worst Retirement Mistakes What You Think You Know About Social Security Might Hurt You The Best and Worst Things About […]

    by » 10 Things to Think About If You Are Retiring in 2013 Topretirements — June 12, 2014

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