I Wish I Had…

I came across an article in MarketWatch that got me thinking, and then it got Deb and I talking. It is called "5 Things You'll Wish You Knew Before Retirement". They surveyed financial planners, asking about their clients biggest regrets in retirement. They start off with the throwaway sentence that "even those who saved plenty wished they'd done some things differently". I will mention that we are not immune to the economic impact that COVID-19 has had on the worldwide economy. But we put together a good plan some time ago, and now is not the time to abandon it. It's proving to be a good plan in spite of the times. So far so good, but wish us (all) luck!

I will also say that we have absolutely zero regrets at this point, but it's good to go through some of this and take account from time to time, especially now as we approach another (the third) anniversary of our retirement. The article I mentioned discussed five common regrets that retired couples have:

  • I Wish We Had Traveled More While We Could
  • I Wish I Had Something to Retire To
  • I Wish I Had More Friends
  • I Wish We Hadn't Bought That House
  • I Wish We'd Talked About Retirement Expectations

Let's see how we stack up to these issues, one by one.

Travel While We Can

We can't agree more with this. Whether you go on ocean cruises, cruise around in your motorhome or car, fly to exotic (or even not-so-exotic) places, Deb and I encourage travel for everyone. You'll find that everyone is different, yet they are also somehow the same. It's a beautiful dichotomy, and one that makes life much more interesting. Go with an open mind and talk with people you meet - you will all be richer for it. And the early part of retirement is the time to do this - don't wait until you're too old to travel!

Of course, you don't have to wait until retirement to travel, and you shouldn't. It's just a great time to do it when you are unencumbered by those pesky jobs and other responsibilities. The financial advisor in me says that early spending (like on travel) is worse than later spending because of those compounding effects. But retired people have the time to pick cheaper dates to travel, and if they are like us, they also don't have the need to live large while traveling - we meet more interesting people in "regular" places than in fancy ones.

We toured a bit of Florida right after leaving Colorado, and then went off to a couple of Caribbean islands in Honduras before going to Puerto Rico. If you've read much of this blog, you know we've spent most of our time on a little island called Vieques. Lately, we've been spending a bit more time on "La Isla" as our friends call it, the main island of PR. We'd also like to hop over to Culebra, another Puerto Rican island, as soon as the opportunity arises. Other travel is being discussed - hardly a week goes by that we don't talk about St. Maarten, Guadeloupe, or someplace else. Travel is a key part of a happy retirement in my opinion, and millions of people seem to agree. The key is to do it while you can still get around well enough to enjoy it.

Retire To Something

Retirement is defined as the act of withdrawing from your job/career, usually due to age, but that's been redefined in recent years to some extent. So it's about retiring from something, the job. And getting away from the stress and time constraints of a job is a great reason to retire. You can finally live life on your own terms, and do what you want, when you want. That's in contrast to work-life, doing what someone else wants you to do, on their schedule rather than your own. This would be your own boss and the company you work for, or if you are a business owner yourself, your customers are the boss and your job is to meet their needs. Either way, you can find your time isn't really yours, but that's also why you get paid!

As much as retirement is about leaving something behind, it should also be about moving toward something. What is that something? In previous posts, we discussed the Japanese concept of ikigai, a reason for living in retirement. Much has been written on this subject, but for us it has been, and continues to be about exploring new things. New places, new languages, new cultures. But there are many new things to explore right back in the States as well. It's such an enormous country, there is much to delve into, much to seek out. We're looking forward to more of our ikigai explorations in the future, wherever the wind might blow us.

Have More Friends

When we left Colorado for a warmer climate, we left many friends (and family members) behind. And that is not without its hardships; those emotional strings are strong. One friend there asked me specifically about this - what about all your friends here? I told him that we'd stay in touch with technology (this blog, Facetime, texts, emails), we'd come back to visit, and our CO friends can come visit us as well. I also told him we'd make new friends as well - this is so important that it is one of the questions asked when calculating life expectancy. That's one thing we've tried to do wherever we go - to make new friends. Some are closer than others, but if our stops were more than a couple of days, we've made friends in every waypoint.

I learned from my step-mother years ago that wait staff at restaurants and bars often have great stories, and great lives beyond the normal "What can I get you today?". You just have to be friendly and chat a little, people love to talk about themselves. You will be rewarded for simply being interested in them. It becomes less of a business transaction and more of a feeling of having a meal or a drink with a new friend. But don't be rude - only do this if they're not busy! But some of the people we've met this way read the blog and others we stay in touch with and visit when we return to their area.

For example, we met a fun young lady in a beachfront hotel bar in Melbourne Beach that we stay in touch with (Hi Jen!). We met quite a cast of characters in Utila, including the famous Mamita who inspired a blog post. We still keep in touch with a pet-loving friend we met in Roatán (Marti!). We have many friends in Vieques, some very close, and a few on the main island of Puerto Rico as well. We also have met some fun tourists - this summer I'm even going to be officiating the wedding of a great couple we've become close friends with!


I like to think of these friends as a trail of breadcrumbs leading back from where we came. So in our minds, the solution to having more friends is making more friends. Some will be close, some less so, but all of them enrich our lives. Our old friends remain locked in our hearts as well, we hope to see more of them as time goes by.

Don't Buy the House

This is a trap we've avoided mostly by planning our next adventure, and the next one. It reminds us that owning a house doesn't make perfect sense right now. We may not avoid it forever, but at some point in the future, if we do decide to buy, we're hopeful that a good plan will make it work for us. The key is thinking ahead and not just buying another house because you've always had one.

Ask yourself if it serves your needs and wants for the near and mid-term (at some age, there is no long term!), or if renting might make more sense. It helps to not have a lot of STUFF though, to give yourself more flexibility. (sorry STUFF people, but you knew I was going to say it!). At our place, the bananas, starfruit, passionfruit, mangoes, and avocado all come free whether we own the house or not. So do the iguanas, cats, horses, giant centipedes, and huntsman spiders! So that doesn't sway things one way or the other.

Now if you think it always makes more financial sense to own a house, think twice. It can be a bit of a coin toss, whether you win or lose in owning real estate. We've been fortunate to make money in all the houses we've owned, but in one case, the Realtors made more than we did (and we did all the work!). I've known people who lost money because their situation changed and they found themselves in a bad spot having to sell right away. Others have invested too much money in a house and later had trouble selling it. That's a real financial trap for some people and we don't like the feeling of being trapped. Some of that risk, but not all, can be mitigated with extra planning, which may include renting.

As with most things in life, renting vs. buying is a series of trade-offs. Home ownership has its hassles, too numerous to mention. But so does renting, and that starts with the landlord. We have been very fortunate so far to have great landlords, but even with that, we can't modify the home to our liking - it's not our house! But if it gets to the point where we would like to settle down a bit more, we may want to do just that. We call it "gettin' broody", a term we learned from our son the chicken farmer. So I'm not really saying "Don't Buy the House". I'm saying think about it and plan it, don't just do it because you've always done it. One day, we may really want to modify our living arrangements to our specific wants and needs, but we also would rather do this only one more time. That makes the location even more critical, but when we find the perfect place to be, that's when we'll buy.

It's a cute little house

Talk About Expectations

This is one area that honestly, we've excelled in. We talked about this repeatedly in this blog, but it really has been a strength for us and I'm proud of ourselves! This continues almost daily as we think about what's next in our lives. The more we talk, the better we plan, and the conversations alone are worth it, even if those plans get scrapped and tossed off the boat. It keeps us close, it keeps us on the same page, and neither of us has expectations that diverge very far from the others'.

We might hear some Bahamian music on Pandora and start to think and talk about, going back there. "Didn't you love the people we met there?" "And the beaches were gorgeous, too!" "Remember getting directions? Turn right at the big tree. ALL the trees are big!". 🙂

Then, the conversation might start to wander a bit, "Can you even understand these lyrics?" "Nope. I understand the Puerto Rican Spanish lyrics better than that". "I like the beat though." 🙂 Then again, if we lived in the Bahamas, we'd come to understand before long, ya mon, for true brudda!

Eleuthera, Bahamas - years ago
Eleuthera, Bahamas - years ago

All of this is a way of bonding for us, planning for our future together and, this is important, seeing ourselves together in that future. We really love this. So as we've said many times before, talk to each other. And talk some more. And then a little more. It's worth it in so many ways.

Places where we've pondered the future

We may touch on some of these subjects in more detail in future posts; they are interesting and important to retirees who still have a lot of life to live. There's a point made by the old joke "If I'd known I was going to live this long, I'd have taken better care of myself" - this is worth coming back around to as well. In the meantime, get out there and live, while you still can!

TODAY'S SPECIAL: "Yayo", by Papayo, Pitbull, & Ky-Mani Marley. "This song is all about teaching the world that you have to live life. Don't let life live you. Dale (do it)"



  1. Paul B on April 16, 2020 at 9:49 am

    Excellent column, as always, good retrospective..thanks!

    • Norm Pyle on April 17, 2020 at 6:32 pm

      Thank you Paul! Dale! 🙂

  2. Anonymous on April 16, 2020 at 10:33 am


    • Norm Pyle on April 17, 2020 at 6:34 pm

      Thank you! “Every day above ground is a great day, remember that!” – Pitbull 🙂

  3. Matthew D on April 16, 2020 at 11:09 am

    Glad you to hear two are doing so well and faring through this pandemic. That was a great article. Thank you for sharing with us. I loved your perspective and resonated with the things you wrote. Have a great rest of your April. Stay safe and healthy.

    • Norm Pyle on April 17, 2020 at 6:37 pm

      Thank you Matthew – very kind words. So good to hear from you! Hope to see you soon.

  4. Kevlar on April 16, 2020 at 11:31 am

    So glad you’re doing well. This blog is a nice contrast to the fact that today’s snow took down half my crab apple tree!

    • Norm Pyle on April 17, 2020 at 6:38 pm

      Kevlar, sorry about the crab apple! I’ve been seeing lots of snow pictures from CO. It’s beautiful, but I don’t like the tree damage. Have a good spring!

  5. GRETCHEN MULDER on April 17, 2020 at 5:23 pm

    Looking out the window at 12″ of snow in Colorado and wishing I was in Vieques or Culebra. Love your blogs.

    • Norm Pyle on April 17, 2020 at 6:41 pm

      Hi Gretchen, see above – I’ve seen a lot of CO snow pix these days! Enjoy Springtime in the Rockies! Thanks for supporting us! 🙂

Leave a Comment