A Twinkle in our Eyes

My earliest memory of our retirement journey (what we have called “Our Adventures” for lack of a better term) was in talking with a financial planner in Fort Collins, CO sometime in 2013. He asked us about our goals. I thought it was a strange question because doesn't everyone have the same goals? That would be to put away a bunch of money and retire one day! At 62, 65, 67, 70, I didn't know, but that's how it goes, right? I guess it isn't quite that simple, nor does everyone have the same goals or he wouldn't have asked us. That's when Deb said “I'd like to see Norm retire early”. I laughed out loud (I actually laughed, it wasn't just a cliche LOL) because I knew what our portfolio looked like and the nest egg wasn't ready to hatch!  The financial guy turned to me and asked, “Did you know about this?” and of course I did not! So I guess he's quite a good counselor as well as a financial guy. We didn't end up working with him, but his question started a long conversation that continues to this day.

Some time later, we met a great couple, Mark and Maureen, with whom we had a lot in common. They were planning their retirement to Hawaii, and everyone knew them as the Hawaii people. Right away, Mark started in with a question of his own: “So when are you guys going to retire?”. Another question. “I don't know, maybe 10 years” was my non-committal response. “But 10 years is a LONG time, Norm!” he asserted, and I couldn't argue. But again, the question kept the conversation going between Deb and I.

The next time we saw them, I had started to do some real research, and I was confident we could retire in only 8 years. Give or take. But Mark informed me that 8 years was still a long time. So back to the research – I was reading hundreds of pages of financial books at this point, and playing with personal planning software to help me understand the averages, the worst-case scenarios, and basically quantifying the risks. The next time I saw him, I confidently told Mark that we might be able to do it in 5 years. Maybe, if things went well. I was surprised to learn that 5 years is also a long time. So I went back to my spreadsheets, and Deb and I talked some more.

Dark night sky with stars
Twinkle, twinkle

The conversations continued over the coming months, most of them while sitting in the hot tub in our yard, staring up at the stars. Just think of it, those same stars were shining down over the Bahamas, Grand Cayman, Puerto Rico, Guadaloupe, Grenada, and other warm places we wanted to visit or re-visit! But to retire early, there just wasn't enough money, certainly not with the uncertainty of health insurance costs. No matter who was running Washington DC, your D's or your R's, there was great uncertainty in the cost, and that continues. So what to do, what to do? Turn off the hot tub jets and have another glass of wine, that's what we did. And we talked some more.

Eventually, we came to an epiphany which was this simple: we couldn't afford to stay in the U.S., but we didn't want to stay in the U.S. either! (Edit: of course we know Puerto Rico is in the U.S. but it doesn't have the ACA requirement affecting our health insurance cost) We wanted to live in the Caribbean  and we were starting to discover some places where the cost of living wasn't too bad. Cheaper in fact than in Colorado, cheaper than many places in the US. And being out of the country, the crooks in D.C. could play their political games all they wanted and it wouldn't affect our early retirement! It didn't just seem like it was meant to be, it was really meant to be! But we talked some more.

Satellite photo of the Caribbean Sea

We talked a lot about what we really needed, the very basics to see if we could afford that, and what we wanted. These were along the lines of a short walk or bike ride to the beach, AC in the bedroom, a decent bed, and a place to store a surfboard, a paddle board, and bikes. We discussed our perfect retirement days which, in our dreams, included a simple breakfast, a morning stroll on the beach, fishing, surfing, spear-fishing, afternoon beers, grilled fish for dinner, and a tiki bar thrown in for good measure. At one point, I came to the realization that this wasn't all just idle talk (although admittedly some of it certainly was). I asked Deb, “We're really doing this, aren't we?”. Deb said she was never so sure about anything in her life; she was surprised I even asked the question. From that point forward, there was no turning back. We were really doing this.

So in the next few months, 5 years became 3, 3 became 2 and then 1, and finally we were counting months. At some point it wasn't “a long time” any more, and I had full approval from Mark to keep calm and carry on. And we did.



  1. Kim on July 8, 2017 at 12:38 am

    You two are still the coolest parents of any student I have ever taught!!Teach us your ways Jedi Masters… we will be your padawans! We want to be like you in 10 years!

    • Deb on September 14, 2019 at 4:18 pm


  2. Zack Pyle on July 8, 2017 at 12:31 am

    Love this!

  3. Alouise Skehan Pyle on July 8, 2017 at 3:21 pm

    What a great idea!Loved reading your "A Twinkle in our Eyes."Alouise

  4. Suzanne Malm on July 8, 2017 at 8:33 pm

    Enjoying the blog and look forward to more. Love that you two are so happy.

  5. Norm Pyle on July 9, 2017 at 12:56 am

    Note to Kim: 10 years is a LONG time!

  6. Deb Perkins on July 13, 2017 at 12:00 am

    Wow! Great idea to make early retirement happen. Good for you! Wish I was that brave!

    • Norm Pyle on July 14, 2017 at 1:04 pm

      Brave? Or half-cracked? Time will tell! Thanks for following us Deb Perkins! 🙂

    • Deb Pyle on July 14, 2017 at 1:14 pm

      Thanks Deb, it should be fun!

  7. Matthew Dozier on July 13, 2017 at 4:02 pm

    Missing you two, but truly glad you are sharing your experiences in this way. Keep it up. Wishing you the best each and every day as you blissfully lie on the beach and sip some cold drink. 🙂 Enjoy your time together, each and every minute of every day!!!

    • Norm Pyle on July 14, 2017 at 1:06 pm

      Thanks a lot Matthew! We miss you and the rest of the gang too. I don’t think EVERY day will be blissfully lying on a beach. Actually, we’d rather walk, swim, body surf, anything but lying on a beach. But we will definitely enjoy each and every minute!

  8. Marla on March 20, 2018 at 7:40 am

    Starting to think about retiring and inspired to read about how you made your Island fantasy into a reality. Good for you!

    • Norm Pyle on March 20, 2018 at 12:41 pm

      Thanks for jumping in Marla, and welcome to the site! If you have specific questions send them along my way, I’ll be happy to tell you more than I know! 🙂

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