What Are Your Challenges in Retirement?

Retirement comes with its own set of challenges. Which ones are you (or a family member) experiencing? If looking ahead, do you foresee any challenges? Tell us what you’re doing to resolve them!

Read it, but I don’t have any of those problems.
I have all kinds of problems [boredom and others] but none of those listed.

I’ve only been retired 4 years, but I don’t have any of those problems either. I do read articles about people who feel that their life lacks purpose, but I never let my job define me, and my purpose in life was NOT my job.

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We’ve been retired almost 2 years. We don’t have those problems either.

Two problems I have are

  1. changing my mindset from save-save-save to spend-and-enjoy. Still not sure what to do about that.

  2. our bucket list is on hold due to covid…don’t want to fly somewhere, get sick and have to live in a hotel room for a week. Meanwhile, we’re riding our bikes to eventually do some touring or bikepacking. That also improves our health!

Me and my peeps on a New Years Eve ride


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I was given an early retirement (they called it a worldwide workforce reduction of 40,000 people or so) back in 2001 at the age of 51. We were encouraged to apply for un-employment and my state appointed a specific employee to handle our claims.

I took a part time job with a contractor to the same company while I sold my house and moved.

I started working in a tourist location while waiting for the closing on my farm. After a couple years I was let go when the manager decided to hire his friend. This was my 3rd manager in 2 years so I guess I was a pretty good employee to have lasted that long!

Starting life as a farmer was not easy, deciding how to plant, pick, process and sell items.

My farm cost $150,000 to which I put $50,000 down and got a 15 year mortgage at about 5%. I used some of the remainder on the sale of my previous house to fix up the farm and put some into retirement. As the farm progressed, I took advantage of a 72-T and then set up a Solo 401-K.

I began running websites for neighbors and others and help them to convert landlines to VOIP service. I also have unfortunately been the recipient of quite a number of calls like “My printer doesn’t work”,“Can you help me set up my new cell phone” and so on. I also am a Board Member of an organization which welcomes cruise ship visitors ang gives them cultural and logistical information about our destination.

At age 73 I am still cutting down trees, using the tractor and supporting customers and visitors.

A friend has recently decided that he cannot manage his farm and I have decided t ouse a chunk of my retirement funs to fix up his farm and profit from its eventual sale. Out here the prices for land and housing will contine to rise and I feel it is a good investment.

Certainly for some retirees, just sitting or traveling is just not in the cards. I am busier now than I was before retirement.

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So nice to see such a large group, and quite a few mature folks, too! Looks a little warm, for Kansas.

I rode thru the winter…didn’t have any snow or salt on the roads. My husband got a new used bike in Feb and he’s been steadily increasing his miles and strength. And we got a rack for the car. I get on the bike and feel like I’m 30 again. Love it!

In retirement, I’ve faced a few challenges, and one of them was managing healthcare costs. That’s when I turned to a Canadian pharmacy for affordable prescription medications. It’s been a game-changer, allowing me to save significantly on my prescriptions without compromising on quality. So, if you’re looking to tackle the rising costs of medications in retirement, considering a reputable Canadian Pharmacy could be a smart option to explore. Remember to verify their legitimacy and ensure they require a valid prescription for any medications you purchase.

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I won’t call this a challenge but often a dilemma. At my age and health, travel is out of the question. So, I’m financially comfortable and looking for worthy and valid ways to donate.

And it’s working well, but am annoyed after donating some place or some thing, I am DELUGED with calls and emails to donate.

That won’t stop me, but it’s a bit discouraging.

If you are lucky enough to have an extended family, it may be a good place to look for someone you might be able to help.

Very annoying. I avoid online donations as much as possible. Some years ago, my husband and I had special checks printed without our address on them, so we mail checks to charities and they can’t contact us back. Old school still works.

The fact those checks had your routing and account numbers could be even worse than a fraudster having your mailing address.

Duluged by the organization you donated to, or other organizations?

Since I don’t answer telemarketers, but do listen to their pitch on my VM, they are somebody else. Same with emails. Mystery people.

However, this is no different than after buying something online. I buy a widget online, and then get email ads for widgets. Never have figured that out.

My understanding (from reading the White Coat Investor) is that using a Donor Advised Fund avoids that deluge. I haven’t jumped in to DAFs yet myself, but probably will before I retire.

Where do I find that?

Vanguard, Fidelity, and I’m sure lots of other places. Here’s some info from WCI:


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These are the things we have done to try not to have our names circulated by charities. We used Donar Advised Funds for a number of years and did all our donations anonymously. We are now mid 70s and are doing Qualified Charitable Distributions. We first contact the charity by phone and have the appropriate individual agree to keep us anonymous. When we mail the QCD check, as a reminder, we write “Please keep our donation anonymous”. Our efforts have so far worked.

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I contribute annually to two or three charities directly on their website. That has never caused me to receive requests from other charities, but I do receive periodic requests from them throughout the year. (Which is annoying, but not nearly as much as it would be to receive solicitations from ones i did not contribute to.)