A few weeks ago I emailed my readers asking for help saying: “Would please list the three most important things – be as specific as possible – you immediately think about when the phrase “my retirement years” pops into your head.”

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  1. Are you worried about being sick?
  2. Concerned about running out of money?
  3. Are you planning on moving abroad?
  4. Do you hate the ides of not working?
  5. Can’t bear the thought of growing old?
  6. The rising cost of living troubles you?
  7. Can’t bear the thought of being alone?
  8. The idea of dying one day has you flustered?
  9. What else? Please surprise me!

In looking through the comments, I’m thinking that these could be broken down into the following categories for the new book:

  • Health, Fitness, Sickness, Long-Term Care, Aging and Death
  • The Cost of Living, Social Security, Investing, Taxes and Legal Matters
  • Your Home, Buying or Renting, Your Safety & Security, Where To Live?
  • Family Matters – Parents, Children, Siblings & Friends.
  • Romance, Living Alone
  • Making Money, Working, Hobbies and Keeping the Brain Active
  • Global problems and How This Could Affect My Retirement.

I was pleasantly surprised to receive so many replies and have included them unedited here below for you to review.

  1. “Yes, I worry about being sick and not having any home-care either in home or placed somewhere.”
  2. “I fear being sick and being a burden to my family.”
  3. “Also, once you drop medicare: from what I’ve been told it is next to impossible to start it back up.”
  4. “I am never going to drop Medicare – ridiculous! that’s the annuity that I count on for my residence, and Medicare can always be used in the US, keeping the US address current.”
  5. “Happy people with positive conversation and lifestyle that is healthy mentally, physically, spiritually and for the Earth.”
  6. “Keeping healthy and learning more about what is important in maintaining ones health, keeping mentally active and positive in life, adjusting your lifestyle to a level that is required to keep happy.”
  7. “A lack of purpose.”
  8. “I’m paranoid about sudden disability.”
  9. “The thing that I feared most happened when my husband died. It re-framed all of my thoughts about worry…. worry kills joy which is a terrible waste of life’s great gift.”
  10. “Rising cost of health insurance.”
  11. “Health issues.”

  12. “Potential health issues seem more important, perhaps because there is no need to soldier on.”
  13. “Health insurance. Staying healthy!”
  14. “Well health care and insurance Is a main concern. Have it now but more worried about after my husband stops working.”
  15. “I am retired. I worry about health as I get older, my independence (mobility, driving,freedom) and just being content and happy.”
  16. “Quality medical care.”
  17. “Better health care coverage and of course better old age residents…”
  18. “I worry about my health.”
  19. “The first thing I do is think of the open-air farmers markets. I close my eyes and inhale deeply. I can smell the fruits and vegetable and flowers. I can hear the hustle and bustle of the vendors and shoppers alike and for that brief moment I am there. We want to be in a small town or village. I want to be where I can plant a garden and want to be where I can grow orchids under my mango trees.




    We are not sure to which country we want to move but have narrowed it down to three possibilities. One in South America and two in Central America. I speak just enough Spanish to insure that we won’t starve to death. The rest I am more that willing to learn as is my husband. We absolutely do not want to stay in the United States. Living in a country where GMO’s aren’t a priority will be heaven. I, for one, am tired of being afraid to eat the food we have here. I cook everything from scratch so that is not a problem. Processed foods and I do not get along.”
  20. “Affordability and access to healthcare.”
  21. “I wonder about establishing and maintaining health coverage for the rest of my life. I have dual US/Canadian citizenship, so the easy answer for me is to retire to Canada (probably Ontario or Nova Scotia), but the easy answer isn’t always the best answer. Especially since Canadian medicare requires me to be in the country for at least six months a year, and I want to live for extended periods in several different countries.”
  22. “How to stay healthy and keep up with the latest health related issues, cures, avoidances?”
  23. “How to plan for long term care?”
  24. “At my now age of 75 plus I am reminded that, at 55, I was able to “retire” since I had enough real estate rental income to do so. My plan was to manage my real estate rentals mornings and afternoon volunteer my time at her school. Move ahead 20 yrs and after we experienced a devastating economic downturn…6 of my mortgages were with two banks that were Federal and went belly up.

    So today it seems too late to reinvent myself. But that is my desire. My wife of 52 yrs is content to remain fully attached to her business; I want to continue and increase my winter time in CR. I lived there for over 8 months a few yrs ago and know I would like to spend additional time this winter. Problem: financial. … and I do live a quite low key life.”

  25. “The age old issue of being in a wedded relationship for many decades and realizing we have different values/goals.”
  26. “Are you worried about being sick? No, better to plan well & deal with events as they happen.”
  27. “Can’t bear the thought of growing old? Getting old sucks, then you die.”
  28. “Dying. We all do it — right? I’m in my early 60’s and in good health. I’m hoping my the time I get to Costa Rica, at age 65, I will be able to have, I hope, another 10 good years ahead of me. My concerns are: putting my new family thru the challenge of taking care of me during the ‘hospice’ time. But, I know they will, and out of kindness, respect, and love. This has already been discussed.

    Another thing that really has me frightened, is that some countries do not believe in ‘Death-With-Dignity’, leaving me to be scared about dying naturally. But, Trust this: I will be finding out a way to take control of this issue — somehow. And once again, I am assured ‘my people’ WILL be there for me. I will be cremated and planted on my property! I will be there, in paradise, and with my loved ones forever!”

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  29. “Finding friends who don’t obsess about their health care. Have you ever listened to a group of retirees at the golf course clubhouse? Most conversations revolve around their prostate or cholesterol or some other medically related subject. As a fairly healthy person, I would rather not obsess with keeping myself from dying and rather focus on getting the most out of living.


    One of my fears about moving into a retirement community is being surrounded by people who behave like the elderly while trying to pretend that they are still young at heart.”
  30. “Health care & food supply.”
  31. “Avoid death. Like John Denver sang once, “I am going to really hate to see it end.”
  32. “Hopefully staying as healthy and energetic as I am now.”
  33. “Age-wise I am in my retirement years. I could be retired but prefer to stay semi-active in my profession while increasingly enjoying Hopefully staying as healthy and energetic as I am now.”
  34. “Hopefully staying as healthy and energetic as I am now * P.S. Age-wise I am in my retirement years. I could be retired but prefer to stay semi-active in my profession while increasingly enjoying Relaxation, enjoyment and More time to travel.”
  35. “Worried about being sick – Not wishing to grow old.”
  36. “Staying alive after “retiring” – I always hear the stories of people dropping dead 1-2 years into their retirement because they started sitting still. I need to make sure the wife & I stay active, involved and engaged with each other and the world around us.”
  37. “Concern about remaining healthy for as long as possible – This means living within reach of quality healthcare, having regular check ups, eating fresh and quality food and keeping active and fit.”
  38. “Cheap, comprehensive public transportation.”
  39. “I worry about outliving my savings.”
  40. “I am careful with my money and live modestly.”
  41. “Want to retire somewhere I can afford yet still have conveniences of modern living & access to excellent medical care.”
  42. “Three biggest retirement concerns? Okay, number one, paying for health care. Number two, not enough cash! Number three, housing. Wait a minute! That’s the same ones as the last fifty years!”
  43. “I want to live comfortably without having to worry about how to pay next month’s bills.”
  44. “How to finish paying for my college loans. how to support my own dreams.”
  45. “Money issues.”
  46. “Rising costs.”
  47. “Money and to be able to afford housing.”
  48. “I worry about having enough money to retire on without having to work, so I plan on working until I am 70.”
  49. “I worry about not having the money to pay for health care, medications, programs for the elderly (like pool exercise) and having the means to get there.”
  50. “Social security, food.”

  51. “Seniors need tax reductions.”
  52. “I worry about not having enough money for my retirement. I’m very concerned about not being able to retire at my appropriate age.”
  53. “Will I outlive my money? Concerned about the price of a car!”
  54. “Is the budget or lack thereof? As I said we are both on social security income and no retirement fund and our savings is gone. Such is life in the good old USA. If we cancel our Medicare Ins we have approximately $2,800 per month. Whoopee! I can hardly stand it. My biggest fear is that our Soc. Sec income will stop. I do not trust our government at all. So an alternate income is imperative.”
  55. “Having enough money to have a good standard of living.”
  56. “How not to lose your money from a scam, poor investment, lawsuit etc. (asset protection)?”
  57. “Falling value of the U.S. dollar!”
  58. “Worried about the idea of dying one day? No, it’s the price you pay for a life well-lived. Civilization is crumbling anyway, and it doesn’t bother me that I won’t see the final collapse [sorry for my grandkids sakes however].”
  59. “Concerned about running out of money. The running out of money is a big item. It isn’t because the retiree didn’t plan and save. They did. They did not plan for government’s fiscal irresponsibility, systematically guaranteeing that their fixed income buys less and less.

    They were screwed over by high withholding and quarterly ‘estimated’ taxes, making savings more and more difficult. Then, they were betrayed by government actions that continue to assure less and less buying power of the dollar assuring a lower and lower standard of living.”

  60. “The rising cost of living troubles you? Troubles me is far too soft a description. The ‘rising cost of living’ is too vague a term uses by some to deflect attention from the real culprit. Out of control government with the ‘inmates running the asylum’… printing ‘green papers,’ at will, just to cover interest on the debt that they created.”
  61. “Defacto exchange controls that will only get worse. These make it exceedingly difficult for the average US$ or EU holder to exchange a good part of their shrinking savings to a stable currency such as the Norwegian Krona, or NZ$.”
  62. “Rising costs of living.”
  63. “Everything legal! Medical, housing, banking, resident requirements (certificates needed, etc.).”
  64. “Will my money last/keep-up with inflation? Markets are fickle and it can all be gone in a heartbeat if some random country somewhere decides to bomb an oil refinery in another random country. A “guaranteed” pension would be nice, but I don’t have that option… it’s all in the market!”
  65. “Affordable and predictable cost of living – Retirees have only their investments and pensions for income. Issues include low taxes, low cost of services, cheap imports, low inflation and low cost of administration- Some of these are also true for Costa Rica but there is always fear for the future.”
  66. “Minimal admin and bureaucracy- This was not on any pre retirement list, but becomes increasingly important with aging. One starts to forget passwords and things. Costa Rica is both onerous and appalling in this area in both banking and all government services. Retirees need simplicity and helpful support.”
  67. “We can easily live in our now very large home within our SS income. Our family visits in person and on Skype. We have formed LASTING, HIGH QUALITY friendships, learned awesome building techniques, and continue in PURA VIDA thanks to the success of our retirement tour business we started those 12 years ago.”
  68. “Making sure my wife and I can find nice housing in a very safe and friendly environment and have a lot of support from other Expats close by.”
  69. “Settling in a community that shares my lifestyle, supports me and is community based. Don’t want to be somewhere that sees me as a tourist or a target to exploit.”
  70. “I want to be somewhere without temperature extremes. I want to have a variety of places to go/things to do within a short distance.”
  71. “Living safely down there without being able to defend myself.”
  72. “Affordable housing issues.”
  73. “Having a place to call home.”
  74. “I worry about mobility and having to give up my home to be closer to the required resources.”
  75. “Mobility, family, money.”

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  76. “Relative affordability of either owning or simply renting over the Canadian winter. We currently own a 3 bedroom condo in Playa Hermosa, Guanacaste. The last economic crash hit us like a lot of other people, so some hard decisions may need to be made in both Canada & Costa Rica.”
  77. “Find a suitable location where we have easy access to the beach for surfing, snorkeling, & ocean activities but living quarters in a comfortable, climate.”
  78. “Although we prefer modest accommodations, ideally 2 bdrms/2 bath, nice but only around 800-1,200 sq. ft., at a monthly cost in the $700-$800 dollar, or less.”
  79. “Since we have already made our decision, most of our concerns revolve around making it happen as seamlessly as possible. Our needs are few, but we would like a large porch, decent kitchen, close to facilities, public transport, etc. The goal is to give up having a car.”


  80. “As we are older, death and being alone are things we have already looked at. This is one of the reasons I don’t want to purchase a residence. We don’t want to leave the problem of selling Costa Rican property to our kids in California.”
  81. “Finding the right tropical spot where I fit in with access to like-minded expats.”
  82. “Both in terms of “my retirement years” and in terms of the act of retiring itself, I wonder about home ownership. First, I wonder how long it will take me to sell my existing home in a tepid market. (Can’t really afford to carry the mortgage on reduced income.) Then, I wonder about my ability to rent an acceptable place for the rest of my life (don’t like large apartment complexes, don’t want to have to move at the whim of a landlord, want to have a home base (see #2)). Finally (for now), I wonder whether it will ever make sense for me to buy, given my planned (hoped for) lifestyle.”
  83. “In terms of living in different countries, a number of those are in Europe’s Schengen zone, and I’m not an EU citizen. Ideally, I’d like to live in Portugal, Spain, Italy, maybe France, maybe Croatia, each for 4-6 months in the off season. I understand that I’ll need long-stay visas in each country, and I wonder how difficult that’s going to be and how much it will interfere with my ability to lease housing in the various locations.”
  84. “If not in a gated community, do I have to have bars on the windows of a single story house? How about a wall around the property topped with broken glass or electrified barbed wire? If I go on vacation do I have to hire somebody to live in the house to guard it? As a confirmed cat person, will I need to buy a big, strong, barking dog?”
  85. “How to stay safe and be prepared, personally and environmentally?”
  86. “Live abroad in a safe peaceful environment, in a beautiful place, on or near the water. Need good reliable high speed internet and roads, close to a airport with international flights.”
  87. “Near an expat community. I do not speak Spanish, so I would want to live in a community where there are English speaking people. Need to know more about where to rent, how to rent, cost, legalities I would need to know more about the weather and the ‘cool’ places to live.”
  88. “I worry about “them” telling me I’m old. I’m 68 now and don’t plan on getting “old” til I’m at least 80!”
  89. “Being away from family.”
  90. “I worry about my family if I should retire outside the US. I would worry if I had to leave my friends to leave the US.”
  91. “Learning Spanish maybe. Making friends and finding a great solid Christian church to worship and church family.”
  92. “Getting both partners to agree on retirement plans! Where to stay, where to go, why go, when to go, …. if at all.”
  93. “I would like to have access to continuing education programs.”
  94. “Loss of identity (especially those that had high powered jobs and where what they did), difficulty in relationships due to the lifestyle change of retirement (sometimes too much time together is not such a good thing!), what to DO and how to make NEW friends…”
  95. “I worry about losing my friends, the safety of the world for my children and grandchildren and I worry about losing my dog.”

  96. “I worry for my children every day and grandchild – I hope that as I grow older it will be gracefully and I will try and work for as long as I can. I wish it was like the old days when parents were welcomed into their children’s homes for a while before going into a nursing home. I wish for health, happiness and of course money.”
  97. “I worry about my and my husbands health as we grow older.”
  98. “I worry about having to leave my home & burdening my family, also being alone.”
  99. “How to take care and be involved with aging parents in your home country (if you move out of the country)? Or kids-other family members that may need help or get in trouble?”
  100. “How to stay socially connected (new and old friends)?”
  101. “I worry about missing the kids and grandkids back in Ontario. Three months is OK.”
  102. “If we lived abroad, the cost of air flights is ok for us, but the kids can’t afford it.”
  103. “The concern of cutting off my family relationships to satisfy my wanderlust thoughts.”
  104. “Staying connected with family. We have 2 adult kids (19/23) and want/need to stay engaged in their lives even though we may retire 1000s of miles away.”
  105. “Being old and dying is where we are all headed when we take our last breath… nothing to fear.”
  106. “I worry about growing old. As my wife and I are childless, we won’t have any sort of support system as we get much older (which is many years away). So we will have to develop that support system in our new home, which we hope will remain Costa Rica… but you never know.”
  107. “I worry for my kids everyday as they have stepped out into their journey with the Navy…”
  108. “Can’t bear the thought of being alone? Not at all- I could go either way.”
  109. “I want to meet interesting women. After the age of 50, it seems that most single women are interested only in their financial security (usually through a partner) or trying to hang onto their youth through plastic surgery or sexual conquest of much younger men.

    Again, in a foreign country, the choices may be even more limited. While many single retired men dream of finding a young, beautiful woman who will be dependent on him, I much prefer independent, interested and curious women.”

  110. “Retirement is what you make it! Keep busy! Help someone every day! It has been our happiest time! Quit worrying and live!”
  111. “I think about being alone not having anyone to grow old with…”
  112. “I think about getting sick..and have to burden someone with illness…”
  113. “Best advice though is to NOT retire from life and to keep working at something you enjoy.”
  114. “I think about finances.. If I’ll be okay.”
  115. “Concerned about inability to generate income during retirement.”
  116. “Want to retire and be able to still follow my passion, where it is running a small business, consulting or volunteering in ways that help others.”
  117. “I worry about how I will spend my time during my retirement. Although I would again say that this is more of “anxiousness or excitement” over what I will choose to due during this next phase of my life. There are many options at this time and I feel that I will necessarily have to filter down to a controllable set.

    As a note, I really feel that I could not retire if I were to stay in my current location/lifestyle. I think I would get bored. Moving to another country is part of a “rebirth” into a new phase of life.”

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  118. “I want to experience a sense of adventure and not just grow old and stale.”
  119. “Health, money, being able to do the things I want.”
  120. “Running out of money, and finding time to do the things I want to do. Working never seemed to eat as much time as not working.”
  121. “Being handicapped in some way, losing my mind.”
  122. “Keeping my mind active with spelling, math and every day events. I just retired after 40 some years where I worked daily with this, finding it hard to find something to full-fill the time using these.”
  123. “I worry about being able to keep up with our home and yard as I grow older as I do the majority if it now, because my husband is a disabled Veteran, he is not able to help much, but he does keep up on our laundry!”
  124. “Not enough time to have fun, not enough draft to fill me up and not enough dancing.”
  125. “I worry about dementia!”
  126. “I think about 1) Chillaxing 2) Sightseeing 3) Eating and Drinking
  127. “Maybe we should create a course called Retirement 101 since no one teaches us the art of retirement.”
  128. “I worry about my ability to learn at least some Spanish.”
  129. “Being able to wisely divest and to extract ourselves from our careers & possessions.”
  130. “Have worked since I was 12 and have been running both domestic and international businesses for years and (sit down for this) really enjoying life – the travel, the challenges, the stress? and the satisfaction of growing a business and the reward seeing my associates advance, raise families and prosper – retirement may not be too inviting.”
  131. “Tell me about retirement again! For an energetic, old Type A personality.’
  132. “How to generate income from your investments?”
  133. “How not to duplicate costs in both your home country and the new country you live in. Insurances, autos, places to live etc.”
  134. “How to reduce travel expenses?”
  135. “How to keep learning new things? Languages, instruments, chess, sports etc?”
  136. “How to have the best quality of life and stay active all the way to the end?”
  137. “How to be happy and fulfilled?”
  138. “How to help others if you want to?”
  139. “There seems to be so many things I want to accomplish … finish a book I’m writing, return to sailing/cruising which I have enjoyed at numerous times in my life, etc.. It seems to be a concern of mine that I have difficulty making a decision regarding the many things I enjoy and find satisfaction in within a now non- limitless life time. Fear of too many alternatives and the perception of too little time.”
  140. “Some people hate the idea of not working? No matter what, my mind and body will be kept busy.”
  141. “I worry about the lack of intellectual stimulation. After leaving the workplace, it becomes increasingly difficult to find people who want to discuss anything beyond their own simple wants. Perhaps retiring in a foreign country may actually make finding interesting people even more

    142. difficult…”

  142. “I am looking forward to relaxation and enjoyment and having more time to travel.”
  143. “I followed the golden rule, I worked hard and played hard and always put away for my retirement.”
  144. “1. I worry about running out of money before I run out of life. 2. Missing the enjoyment I got out of working (I know I may be odd in this respect).”
  145. “As I approach my 58th birthday I feel concerned that I will still be working 12-15 hour days in order to keep the money flowing. I have not seen much success with my stock market portfolio and doubt dividends from that source will afford me the life style I aspire towards in my retirement. to live out my retirement. I’ve always been heavily invested in real estate and am hoping that will still be my “go to” place for my retirement.”
  146. “I worry about living comfortably on our SS monthly income.”
  147. “I worry about living comfortably in my retirement, having retired in 2010 and realize I cannot do so in Australia; biting the bullet and making the move to become an expat; finding the country that is right for me.”

  148. “How to best manage your legal affairs when living out of the home country and how that impacts the new country (wills, trusts, banks, real estate, taxes, insurances etc.)”
  149. “How to avoid negative news, politics, people, topics, thoughts etc. and stay focussed on being a healthy, happy, fun person.”
  150. “I worry about government failure, escalating violence worldwide and growing poverty.”
  151. Living Abroad: “Have we waited too long? Will we be accepted in a foreign country and will we be able to obtain residency?”
  152. Living Abroad: “How best to manage shipping and receiving when living out of the country, especially for things you need for health, like medical supplements that may not be available overseas.”
  153. “The overall concern or theme for me when working on my retirement plan, is to design it to be as simple as possible, yet complete, robust, comprehensive and integrated. With all the players on my team working together or able to communicate with each other (lawyers, accountants, insurance agents, realtors, doctors, investment managers etc.)”
  154. “I want everything I can think of set up and done ahead of time and basically running in the background on autopilot. I want to spend my retirement living and not managing all of these aspects, especially during stressful/crises/health situations.”
  155. “I adore retirement. I know that all those naggy little things like sickness and death will come, but they are not here yet and so I refuse them mental energy. The only thing that has the power to worry me is the welfare of my children (adult) and once in a while a little “I’m happier than I deserve to be guilt”. And a certain generational angst-that I have not done enough to ensure such circumstances for the younger folks.

    Otherwise, every day, every moment, every palm, every bird, every roll of the surf, every bite of shrimp, every sweet dog, my old man, all of it is sheer joy.”

    156. Costa Rica Specific:

  156. “The CAJA health care that I was REQUIRED to purchase was scary, but CIMA Hospital is a wonderful facility and I was fortunate enough to have the funds to pay the costs out-of-pocket.”
  157. “Our Tico neighbors in our small town of San Ignacio de Acosta where we had bought a small home, essentially adopted us in the first day we were in the house. They introduced us to the incredibly good CAJA and private medical systems which erased our medical health care concerns. We have had major health challenges in the 12 years and all have been resolved to our satisfaction. We have found this to be the very best 12 years of our lives.”
  158. “We now live in Costa Rica, and are very happy by the way, money is not the problem it would be in the States. But our health becomes a problem. CAJA and the doctors in CR are the best that they can be. But, the funding from the government is not enough to bring the medical field in line with the States. We have kept our Medicare and part F which does add an unwanted expense but is a great safely net.”
  159. “I’m a US military vet and one huge factor for me is having a VA hospital there (I understand there is one). Making sure I have great health insurance for my wife and I if I decide to go outside the VA.”
  160. “Receiving my V.A. meds and medical care, or Medicare down there.”
  161. “We also see the prices going up and we not only wonder how this is going to effect us but our Tico friends.”
  162. “Laws, regulations, and enforcement. Generally speaking, there is not a lot of latitude for interpretation of basic laws or financial imperatives in Canada. In Costa Rica it frequently seems that what is right, wrong, or indifferent depends upon the lawyer/banker/bureaucrat one talks to.

    Sometimes it seems to vary with the time of day! Laws are made, appealed to higher courts, then quashed/stayed/amended, or even occasionally upheld. In the meantime it becomes very difficult to be compliant and not a sucker. Try getting your money back after paying a tax that is subsequently struck down… good luck to you.”

  163. “I was concerned about FATCA and its effects, but have been told that once we obtain residency, we will be able to open a bank account relatively easily.”
  164. “I am 3 weeks away from retiring from my current phase of life at the age of 55 and 3 months from moving to Ojochal, Costa Rica with my wife to begin the next phase of my life. I have planned accordingly (possibly over-planned) for the financial aspect of retirement, so that is not a huge worry, however, I would say that diligence to budget is certainly something we will be committed to. I would say that the (#1) worry would be the uncertainty of moving abroad. While we have planned, researched, investigated, and communicated diligently, the uncertainty/excitement is still there.”
  165. “Can I afford to rent in Escazu or Santa Ana? (where I think I’ll be most comfortable)”
  166. “We have three cars, but try to use the bus on longer trips when convenient. We pay our workers justly and always keep up their CAJA and vacation/christmas bonuses. We treat them with the respect they deserve. Life is great in Costa Rica!
  167. “I worry about ‘being alone’. Over the years I have built fabulous relationships with some families, and have been invited into to lives and hearts. Because of how the US views family and friends (the fact that family and friends really don’t even rate in the top #10 of priority). I feel more loved and cared from by people I have not known for more that 15 years here in Costa Rica, than by people here I have known for 35 – 43 years in the U.S.”
  168. “I expect family and friends will want to visi

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