October 15, 2019

Reader's Questions: Time To Ask a Few

One of my favorite parts of the blogging process is reading comments left by readers, receiving emails asking for my advice, or getting notes from authors interested in my thoughts on their new book. That type of involvement makes everything else worthwhile. 

A file folder full of questions has been calling me, asking me to answer some of the thoughts and concerns that you have. Well, since I can no longer close the desk drawer if I don't tackle at least a few of the things in that file, here goes.

Staying in Touch

Several folks wondered about staying in touch with co-workers and friends who are still part of the working world.

Steve noted his problem "stems  from my decision to keep my distance from my old workplace (I was a teacher) because whenever I went back, the stressed-out looks on their faces almost made me feel guilty. All they could really say was how lucky I was (I learned early to stop talking about how great things were for me....). They were all gracious, but the envy was more than palpable - from both the older and younger friends. This was/is pretty frustrating because I had/have such a strong connection and network among still-working friends."

An e-mail said, "Sometimes I miss the everyday contact with my fellow worker bees and the conversation. I probably need to work on this area."

Health Care Issues

As you might imagine this was the subject of several comments.

A lady presented a common situation and a question: " I'm not yet retired. My husband and I are inching toward it; he's down to four days/week, and I'm down to three. The big glitch, from my perspective, is health insurance... He's already on Medicare, but I'm several years away from that. Otherwise, financially, I think we could make retirement work (in a frugal sort of way). But for me to buy an individual policy in New York would cost over $800/month, and that just feels prohibitive. Even though I'm pretty healthy, I'm uneasy about going without insurance. If you or anyone had any suggestions, I would welcome them."

Unease about the Future

One regular reader hit on some of the basic day-to-day problems I had never considered: "I am on countdown now to retirement next May. As it gets closer, all the emotions are being pushed to the side by practical issues. If I can't buy my work computer, I have to buy a new one and transfer everything. I use my work email as my personal (non-blog) email. I have to transfer to a new email account. I have to buy my own health care, and I can't get one of my kids insured. I have to clean out my office. I have to figure out how to do some things for myself that assistants do for me now (I know--I'm spoiled). And so on. Oh, yes, and I have to keep working until May 31! I know it will all get sorted out, but right now I feel a tad overwhelmed."

Trying Other Things

Retirement can be a time to try on a different lifestyle, or indulge your love of exploration.

Jan asked, " What is your opinion on doing Peace Corps work for a couple of years? My husband doesn't have a pension, and would like to get away from his stressful job. I think we could rent out our house and save money by teaching abroad or doing Peace Corps work, and that would be another wonderful adventure that would teach us to be happy with less, and give us fabulous memories."

William wanted to know when are we are too old to try something new. I gather he had read about my guitar and painting efforts and wondered if there comes a time when our mind and body don't respond well to "new."

Other comments and concerns

"Here's the question....when our dog goes to dog heaven, do we enjoy our less complicated life, or do we continue with the complications a pet brings, and continue to reap the rewards of having a true friend to share our lives? There is no right answer, but I'd like to hear what people say."

One fellow e-mailed: "I have been retired a little more than 4 years at 55. Once I retired it so happened that 2 of my kids became homeowners - which meant helping them get the houses in shape. Then one of my daughters was raising money for a charity so that she could run in a marathon on the west coast. That provided an opportunity for my wife and I to take a 3 week trip to see her running. We had a borrowed laptop from one of our kids and it prompted us to learn about the destinations and get a room where we were headed.

Since my wife still works, I am the appointed Travel Director. Since my retirement we have been on cruises to Panama and Alaska, with road trips to North Carolina and the Daytona 500 with several stops including New Orleans. This period of my life has been enjoyable with occasional jobs, some volunteer work, walking daily, watching grandkids and all of the other little things that come up."

Another comment noted: "the best gift of retirement has been the gift of time. However, I am learning that I need to use my time with a plan rather than floating through the days as I did in my 'flower child' time of life. I find that having some structure and some flexibility is the best approach. Of course, all of this works only if you have already identified your hopes and dreams and aspirations for retirement."

Finally, Susie was one of several that asked about budgeting. She knows I am a strong believer in their usefulness, but her question was simple: "I have maintained a budget all my life. Now that I am retired, do I still have to keep track of everything? I want to cut loose a bit."


Now, it is your turn to weigh in with thoughts, suggestions, or questions. In summary, here were the major issues raised and questions asked:

  • Once you leave work do you leave that work world behind? Should you? How do you deal with jealous friends? How do you simply walk away from what was a big part of your life?
  • With health insurance to the point of being unaffordable for many of those still working, what can someone do? If too young for Medicare do you risk everything going without insurance? Are there other  options?
  • Have you thought about all the little stuff, like changing e-mail address, getting all your files from one computer to another, or buying a home computer? What other parts of your life have run through your work place that now must be handled in a different way?
  • Volunteering can be a good use of your time. What what about something as radical as 2 years with the Peace Corps? What do you do with all your personal belongings? Can you be away from family and friends for that long? What other considerations are there?
  • How structured are your vacations and travel experiences? Do you just pick up and go, or do you prefer to have everything plotted out? How do you stay in touch, handle bills and mail?
  • Are budgets and keeping track of how your money is spent still worth the effort? After all, isn't it time to enjoy what we have and stop worrying about that $5 coffee?

Pick one (or more) or the areas above and share with us your thoughts, experiences, and suggestions. Or, feel free to take on a new issue and raise a fresh question about an area that particularly concerns you. I promise I won't stick it in my file drawer!


  1. Bob, I've mentioned before that you've built a great community through your blog, and this post is a perfect example. My two cents:

    Regarding former colleagues, rather than visiting at work, try reaching out on an individual basis to a few people you would especially like to stay in touch with. Offer to meet for pizza on a Friday night or breakfast on a Saturday morning. If your invitations are accepted, then you know that your colleagues are truly interested in staying in touch. If you receive no response or only excuses after a couple of tries, then you'll know where you stand. If that's the case, move on and develop new friendships with other retirees. Sometimes friendships develop due to circumstances, and last only for a particular stage of life. And it takes two to maintain one.

    Regarding health insurance: Life changes in an instant, and one major medical emergency and/or hospital stay can easily bankrupt some families. Before discounting health insurance offered by your state through the Affordable Care Act (ACA), meet with someone from the marketplace to determine whether or not you would be eligible for ACA tax credits that will offset the cost of the monthly premium. The tax credits are based on income so be sure to run your situation by your tax preparer or accountant, as well. Why? If you use the tax credits to lower your monthly premium and end up with a higher annual income than expected, you may have to repay all or a portion of the tax credits when you file your taxes. If you find you still can't afford the insurance, consider delaying your retirement until you are eligible for Medicare, or work part time to earn the income to pay for your health insurance premiums. If you work part time, have a backup plan since many people are forced to leave the workforce for unexpected reasons.

    Regarding replacing a pet who passes: Alan and I have had dogs since the third of our forty years of marriage. When Tanner, our beloved Alaskan Malamute passed three years ago, we decided no more dogs - for now. We're definitely enjoying the freedom to leave the house on full day adventures, and travel without the angst that always came with leaving him in a kennel. (Tanner loved the kennel and its staff; it was Alan who couldn't handle him being there.) The irony that we were paying more per night at the kennel than we were paying for our campsites was not lost on us. Eventually, we know we'll cut back on our travel and other activities, and will happily bring another dog into our family at that point. Until then, we are enjoying our adventures (big and little), and the freedom from worrying about our pet when we're on the go.

    Regarding budgeting in retirement: I still track all of our expenses and maintain a spreadsheet that allows me to see where we stand in relation to our annual budget at any time. I don't like surprises.

    Excellent post, Bob!

    1. And a solid response to several of the questions, Mary.

      It is rare to maintain work friendships for very long. Naturally, the connection of shared experiences and day-to-day context are gone. The few times I am aware of a friendship continuing after retirement is between two or more people who had built a solid bond outside of work, with shared experiences and interests.

      The dog situation is one Betty and I will face in the next 6 years or so. Our dog, Bailey, is closing in on 8 years old. She has joint and mobility problems that only partly respond to medication. I really don't know what we do when she dies. I think it depends on our housing and health situation at that time.

      We do have a "backup" dog. Our daughter's dog is four. She travels for work a lot so we care for Adler when our duaghter is out of town. Adler (Adi) is likely to live another 8-10 years so we will have a part time dog after Bailey is gone.

      I continue to keep a budget and use software to keep track of all expenses. I have done this for so long, I'd feel quite vulnerable without the information at my fingertips.

  2. When I was young I romanticized joining the Peace Corp but now I see all complications of doing so...what about my house and things inside? It would be a huge undertaking. Plus when I was younger with stars in my eyes I didn't see the world as a dangerous place like its become in recent years. So that's off my bucket list. So is joining the circus which I literally (sort of) came close to doing when I applied to and was accepted into the Ringling Brothers Art School in Florida.

    I did spend a year volunteering at a museum after my husband died but the job they gave me I was working all by myself and it was not fulfilling my needs, at the time, to make new friends.

    1. I never seriously considered the Perace Corps, though I was interested in the domestic version. But, it never really caught on and fell victim to politics and budget cuts.

      We owned a time share vacation rental for 20 years just south of Sarasota. I have seen the Ringling Art school and museum...a beautiful facility. Now that there is no more circus, you don't have worry about that unfulfilled dream!

  3. This is not exactly answering the email question. But I am convinced that people who have strong lives away from work (a seperate email, friends who are not work related o other kid's parents) hobbies and people that you socialize who are not work or family related. Do So very much better later on. As to another question I ahve considered long term volunteering and have a new retiee in my group who went overseas to teach english and stayed there for five years. I do consider volunteering a major point

    And while I am sure I would have more to say later. I have a dog, I travel with a dog and my dog loves his carers when we are not here so the travel thing is not an issue. I honestly believe as said above that for most people the boarding issue is about the people, not the dogs. Most dogs are flexible, and are happy to be with people who love and care for them (sometimes more than thei owners do) for a week or so if they have been properly adjusted. Obviously that doesnt address the boarding cost itself.

    1. Our dog is a very nervous animal. We had her in a well-respected kennel only once. She returned traumatized by the experience. Since then, either our daughter stays with her, or we hire a house/dog sitter. Actually, the sitter is less expensive than a kennel. Plus, we feel better about our home being occupied and cared for.

  4. In terms of health insurance-one thing to check out is whether or not your employer would allow you to stay on in a consulting role and continue you on the health plan. Some professional firms (mine included) will allow that. We have a friend who is a sales professional who was able to negotiate continued coverage because his employer valued his ability to stay in touch with long time customers and generate new business. The ACA impact for the employer would have to be analyzed, but it is worth looking into.
    One question that has been weighing on my mind is this: how do I make new friends in retirement? I am starting to experience what many others probably have experienced: the death of close friends or close friends moving out of the area. In past life transition periods (transitioning from public school to private high school, moving to a new area after remarriage), I have gone through bouts of loneliness that have brought me to tears. I've always done a good job of keeping in touch with friends both near and far. I also have a wonderful husband who is good company and makes me laugh. However, I have often been so snowed under by a more than full-time work schedule and a long commute that I can go for several weeks without an in-person lunch or afternoon with a friend. I am good at checking in by phone, but am not much of a texter. I've found myself wondering how to deepen in-person connections (and make new ones) once I am not spending 60 hours plus per week working and commuting. Any suggestions? Also, how do I get better at checking in with friends via text?

    1. Beth, it sounds like a trite suggestion but one option may be meetup I am the part coordinator of a meetup for women of a certain age called the divine divas. I think we are equally single and married. We mainly only do things in the day (not interrpupting family time). I know a city near me has what they call an emtpy nesters group.

    2. That's a great idea, Barb. I have recommended Meetup to my kids for professional networking, but it could work to meet friends with common interests as well. By the way, in addition to reading Bob's blog, I am a faithful reader of your retirement blog as well.

    3. BethC, my suggestions are to 1) seek out activities that appeal, ensuring you'll have at least one thing in common with anyone you meet there, 2) make up retiree contact cards and hand out to anyone you meet that you feel has the potential to become a friend, 3) follow up with an invite to a low key event like coffee, a walk, or lunch, and 4) say 'Yes!' to every invite received.

      We relocated two years ago. The first year was a little rough because while we were meeting people daily via the many activities we became involved in, we didn't yet have history with anyone. Now we do, plus we're continuing to meet and make plans with new people we encounter, to the point our social cup is now full to overflowing, both individually as well as a couple.

      You know the TV show, 'Say Yes To The Dress?' If you focus on saying 'Yes' in retirement the friendships should follow.

    4. Thanks Tamara- I plan on looking into the classes offered by our local Osher Living Learning Center, which I first learned about through reading your blog. We've been fortunate to live in a neighborhood we we were part of a close-knit group of friends-however, now we have had several friends pass away (way too young), and others are in the process of moving to warmer climates. The ideas that you and Barbara mentioned are very helpful, and I am glad that you're making new connections in your new hoe,

    5. Beth,

      I am a big believer in programs like the Osher Learning programs for adults. As Tamara notes, they are great places to meet others with similar interests, as well as first-rate ways to keep your mind stimulated and growing. We are lucky to have a very active program run through Arizona State University with multiple sites throughout the Phoenix area.

  5. Hi Bob! As a self-employed person I've had private health insurance (and paid for it!) my entire life. I have an HSA plan with a high deductible. Still, it is the single largest bill in our house. I won't go without insurance but I do get the cheapest high deductible I can and put away pre-tax dollars in the HSA. It works but I'm counting the months (6.5) to Medicare.

    As for a dog, I can't imagine life without one. My dog Kloe adds so much to my life that it's worth the hassles. Fortunately even though we love to travel we have used Trustedhousesitters for a couple of years and had very good results. Plus, the older I've gotten the smaller the dog. I want to be able to easily pick her up no matter what. ~Kathy

    1. Our daughter's dog weighs close to 40 pounds while ours is about 23 pounds. Guess which one is easier to get in and out if the car for a trip to the park!

      Medicare is great, but I am finding costs for the supplemental and drug coverage add-ons are rising well above any reasonable increase.

      I will resist Medicare Advantage for as long as I can, but at some point we may be forced to accept the uncertainty of a private company's restrictions and limited coverage due to cost.

    2. In Arizona the Advantage plans are great.Worth another look.We've been getting great benefits for this past 2 years. Emergencies out of town are covered. Meds covered (with some co pays of course, but my generic thyroid med is zero copay. That's the only med in our family. )-- We only pay the Medicare premium, no more. I have to get referrals to specialists but ave had no problem with that--have had to go to an ENT and a derm (repeatedly!) over the past 2 years.all covered.We love our Humana Gold!!

  6. We were fortunate enough to benefit greatly form the ACA (Obamacare) when we retired art age 60. WWe were able to keep our earned income, MAGI down low enough to receive a subsidy and get affordable plans till Medicare kicke din. Seeing old colleagues: I don’t like hearing working people go on and on about the stresses and details of their jobs,anymore! !! Sorry!! I do have coffee with one of our office assistants who is also retired and travels often.. she is like a sister to me! Other health insurance idea: There are “faith based” plans.. have to google that and get the info..we considered them but did not need to when ACA became available. Details:Well, I can’t imagine worrying about transferring files form one computer to another..especially wth the cloud where you can just put stuff and retrieve from any device. Money/budgets: We still have a monthly meeting to track our expenses. WE just naturally seem to stay in budget without a lot of difficulty. Travel: Some years more some years less. We really enjoy shorter trips around the Southwest and to states we have not been to.. TIme management: I like a lot of loose time, we volunteer some, not every week though. We both exercise almost every day and do a lot of spontaneous stuff like walks in the local parks when a whim hits, or a lunch date out with a coupon.. it all kinda flows.. and has gotten much more satisfying, after a few years of practice,lol!!

    1. Practice for a satisfying retirement. Sounds a little odd, but you are right. We try things, adjust things, and practice with different approaches until we find the right mix.

      You show greater trust in the cloud than many people, my wife included. She has three 1TB external hard drives for her computer. What if the cloud fails or is hacked, she wonders.

      Both those things could happen, but I don't have anything so critical stored on a cloud service or hard drive that such a loss would be any more than an inconvenience.

  7. Great responses here!

    Kind of related: The only problem traveling with my Golden Retriever was the lack of flexibility on the road. I couldn't go into a restaurant, museum, etc. and leave her in the car. Recently I borrowed a friend's pure electric Tesla, which has a "dog mode" that uses its enormous battery to cool the locked car's interior. An anxious dog might fret, but mine just slept. No internal-combustion engine running, so no pollution or over-heating! Some people even use this mode to "camp" overnight, as eight hours of use only drains about 10% of the battery.

    1. Well, that is an interesting solution. And you are right: a dog restricts meals out, or what you can visit and for how long. Motels discourage dogs left alone for obvious reasons.

  8. I retired at 58 to be a caregiver. Health Insurance has been my biggest expense higher than my mortgage. I thought I had a sizable emergency fund but due to dental/eye expenses which are not covered by my health insurance I spent 90% in my first 5 years of retirement and had to take social security at 62. I am finally eligible for medicare effective November 1st. My current health insurance converts to a medicare supplement but effective Jan 1st the cost will be $404.00 per month in addition to the cost of medicare at $135 or $140 per month. This only saves me a couple of hundred per month. I have not tried for any of the advantage plans due to a pre-existing condition which from what I have read will disqualify me. You can try the faith based plans but they are not considered insurance by hospitals and doctors and may require upfront payments. You can also try for a concierge plan but that would tie you to a local doctor and you would still need a policy for hospital care and prescriptions. In short, there is no cheap way to guarantee health care costs
    will be or remain affordable. In the years that I have been retired by insurance went up at least $50 dollars per month every single year. If that is a concern, then continue to work part time

    1. I am glad open enrollment just started. My Part D coverage is scheduled to more than double in cost next year. Maybe all companies are like that, but I am not willing to let Humana just hit me with that increase without due diligence.

      I am avoiding Medicare Advantage for many reason, but one of the biggest is coverage doesn't travel. If I leave my home service area, virtually everything will be out-of-network. With Medicare, it is good everywhere. Am I paying more right now? Yes, but that comes with much more peace of mind.

      Health care costs will continue to increase at rates that are unaffordable for many of us until politicians get the backbone needed to reign in the pharma and health insurance companies. Medicare, with supplemental, and Part D are not even close to being free or very affordable medical care.

    2. I was told by my insurance agent that when I hit 65 and enrolled in Medicare, I could get coverage without a medical exam, thus any pre-existing condition was a non-issue. This included any of the plans I chose, as I recall. I don't have any major health issues , but I know my DH wouldn't be eligible for some of my options because he's been on Medicare for 7 years, and he has a couple conditions that freak out insurance underwriters. This is all to say we found the help of an agent invaluable in sorting through our options. Health care is really complex, and Medicare adds to the complexity IMO.

    3. To be clear, the option of no medical exam was a six month window when I enrolled, not forever.

    4. Bob, I have looked carefully at my Humana Gold Advantage plan.. we ARE covered for emergencies out of town. Check it out--they have reps that can show you the details--they are not high pressure at all.. can just get some info and compare.. locally,Humana has a good network..out of town we are covered for emergencies..

    5. I tried to help a friend of mine with a Medicare Advantage program..and it looks like if you already have lots of conditions and meds it is more expensive.My husband and I have no pre existings and got on immediately when eligible.. so.. no extra expense..we pay our Medicare premium for great coverage. Good idea to sign up before any medical problems rear their head..??

  9. Hello, Bob,
    The topic that resonates most with me is the one about having structure once the time comes to retire. After spending a life in the construction business, which is a very busy occupation, I found myself feeling guilty when I had idle time. It took a while to find activities to fill my day and feel productive. Now, after spending time on church committees, exercise classes, blogging and travel, I don't know how I had time to work! The difference is that I choose to use my time and energy on things that give me pleasure. I continue to believe that retirement is the best gig out there.

    Gave up on pet ownership after we downsized and out 17 year-old big, fat, lovable cat died.

    When it comes to health care, I am one of the fortunate that benefits from a 24 year career in the Army Reserve. We couldn't handle the expense otherwise. Something has got to be done with health care in this country.

    Great post. I loved the comments above. Thanks for asking! Joe

    1. Finding the balance between open time and productive time is something everyone must figure out. You have. I hope the questioner above does, too.

      The number of folks who email me to let me know they continue to work for a government organization or spent years in the military like you for the health and retirement benefits, shouldn't surprise me anymore, but it does. When my career was going well, i don't remember having to worry about medical care and insurance. It was just the cost of living as an adult.

      Over the last 10-15 years all that has changed dramatically. Health care has become one of the primary factors in choosing where to work, or whether to retire. That is a blight on our country and the "leaders". How come other developed countries have figured it out and we can't?

  10. This is a great conversation starter, Bob. My thoughts and experiences on a few things:

    I have not always been great at keeping up with old friends, but I am doing fine with my work friends. We have a core group of 4 that worked together for about 25 years and became quite close in and outside of work. I was quite afraid of losing touch with them as I was the first to retire. However, we have started a dinner group that rotates between our homes four times a year and have a great time catching up. Texting has also been a big help for me as I've never been much good at calling to chat with people. It was a bit awkward when I was the only one that was retired, as they quite openly stated their envy, but I know they never resented me. It is a bit better now that the second one of the group has retired and I can openly talk to him about the joys of retired life. The other two will go in a couple of years and then we will really have some fun!

    I am very fortunate to never have to worry about a health care bill or insurance coverage as we live in Canada. I can't imagine going through what you folks do.

    The technological aspects have not been a problem. I did have a work laptop and phone that doubled as my personal computer and phone, so I did have to get my own when I retired, but it was not a big issue.

    Money matters continue to be interesting. Between my great work pension and my wife's small work pension and two government pensions we have been through almost two full years of retirement and have not had to dip into savings at all. We have pretty much spent what we want and enjoyed ourselves, though we don't live extravagantly. We do have a nice little nestegg available, but there is still that nagging voice that wonders whether we will need that someday. I often think of the stats another commenter has posted here about how a large percentage of retired people die with more money in the bank than they had when they retired and wonder if we should be spending more on enjoying life, fixing up the house etc. Maybe we'll get our brains wrapped around it someday.

    1. The fellow you mentioned regarding retirees being overly cautious in what we spend is a strong advocate for not letting opportunities pass us by. At some point our health will be the primary determining factor. He stresses that leaving money that can be spent because of the fear of running out is unfounded in most cases.

      After his comments, I have looked at my finances and done every projection possible and have become more comfortable in spending a bit more of our resources now. Next year we will take a few once=in-a-lifetime trips. They will exceed our normal vacation budget, but if not when we are still healthy enough, then when?

      Your responses to a few of the key concerns from above have added a lot to our discussion. In terms of health care costs, I just completed the annual gauntlet of picking supplemental and drug coverage plans to flesh out basic Medicare. Too bad you and all Canadians can't have such a thrill every fall!

  11. Another great post and discussion, Bob! I have only a couple friends from my work life that I still stay in touch with, although an unpopular CEO got walked out last week, and I did get a text from a fellow sufferer whose also left that company. There is some satisfaction in seeing people's bad act catch up with them, although I suppose that's not very charitable of me. :)

    I paid out of pocket for healthcare for about two years when I retired, and it was awful. $600-700/month for basically catastrophic coverage. I think my deductible was $7K or something equally ridiculous - I've tried to forget. The day I could sign up for Medicare was a big one at our house!

    As for free time, I'm still enjoying my hospice volunteer work, and I am enjoying learning the harp. I joined a harp circle in my area, and I've met some great people and am enjoying some low key, fun ensemble playing. We have all levels and everyone is encouraging and supportive even if you hit a few clunkers.

    As for the money aspect, I'm still pretty anxious about any major spending - like the new furnace we had to buy last week with no warning. :-( But that's personal conditioning more than reality. We're really fortunate to be where we are, especially when I see what else is going on in the world.

    1. Thank you for your last sentence. As real and upsetting as some of our problems are to us, think about world situations to keep all of it in perspective. The Kurdish nightmare is just the latest example of people behaving badly toward other people.

      Re: your CEO story. Too often it seems like too many people don't pay the price for their misdeeds or boorish behavior. I understand the desire to celebrate (quietly). In this case, not being entirely charitable is forgiven!

      The last two years Betty was on private insurance she was paying around $450 a month, with a $7,000 deductible and copays for all visits. Like you, Medicare day was a big day for us.


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